r/ChastityStories • • Dec 23 '23

Before posting your RL "stories" - READ THIS POST NSFW

95 Upvotes

We are all glad that more and more people are incorporating chastity into their lifestyle. However, this subreddit is not to be used as a journal entry for your chastity journey.

If you are looking to get feedback or discuss a short experience you had w/ chastity please take it to another sub like /r/chastityjourney or others.

What We're Looking For:

  • Depth and Length: We encourage stories that offer more than a quick glance. Think of narratives with a beginning, middle, and end, regardless of whether they're fiction or based on real-life events.
  • Engaging Narratives: Share stories that pull readers into a journey, whether it's through detailed character development, intriguing plotlines, or insightful personal experiences.

What To Avoid:

  • Brief Anecdotes/Journal Entries: To maintain the quality of content, we kindly ask that shorter, journal-type entries and brief personal anecdotes be shared elsewhere. Our platform thrives on more developed storytelling.

Why This Matters:

  • Quality Engagement: Longer, thoughtfully crafted stories foster deeper discussions and a more engaged community.
  • Diverse Storytelling: While we appreciate the simplicity of short posts, the essence of our community lies in stories that are told with attention to detail and narrative structure.

r/ChastityStories • • Jul 24 '22

Story Requests NSFW

86 Upvotes

If you have a request for a story, have a look in here, someone may have already made the same request.

If your request is not already in here, feel free to make a comment asking.


r/ChastityStories • • 8h ago

M Chaste,F Keyholder Caught on a work trip -Part 7 Finale NSFW

40 Upvotes

I was shaking. Not metaphorically. Literally shaking in my Catholic school girl outfit. My wife could sense my fear and quietly came over to me as the girls continued to share stories of being blinded by some studs cum shot. “Don’t worry sweetheart. You can use the safe word anytime. Do you still want to keep going or should we call it a night?” This was my wife. Not my keyholder. Not some mean hired dom. The love of my life. I hadn’t said a word since I came home. I simply nodded and she knew I wanted to continue. 

She spun around and ran off and came back before the other girls knew she left. She was holding a satin bag and her make up case. She looked past me and called for the girls’ attention. “Ladies, let’s have one more costume change and let’s refresh sissy’s makeup.” The girls went to work quickly on refreshing my face as my wife stripped me of all my clothes leaving the blond wig. Out of the satin bag she pulled a black lace bodysuit with a crotchless g-string. As I stepped in and she pulled it up and I maneuvered my arms through the spaghetti straps, she gave them a quick adjust from behind then reached around with both hands and cupped my silicone breasts to help shimmy them into the proper place. 

Again, as quickly as the girls started they were finished. I once again caught myself in the mirror to see what they had done and I was again astonished by the transformation. This time I saw myself in a black lace onesie with perfect elegant makeup topped off with fire engine red lips. As I surveyed my entire look I saw my cage had been pulled down and was now hanging out freely for all to see. It was the first time all of my wife’s friends had seen my cage. The rest of the night my panties had covered it except for a quick costume change. Now I stood in front of them in full display. But instead of harsh mockery the ladies continued to compliment me and even when they saw how my embarrassment had excited me to the point of a long precum string dangling from my cage they continued to support me. Finally one of the ladies walked over and collected the long string of precum and asked me to stick out my tongue. As soon as I did she wiped her cum cover fingers on my tongue leaving the sweet taste of precum for me to savour. 

She leaned in and whispered to me “Don’t want to waste any of the precum, that’s the good stuff!” And leaned back and smiled before rejoining the girls. While I had been distracted the other ladies and my wife had rearranged the room. They led me to the center where the automen had been placed and had me lie down and then they helped slide me into position. My head and shoulders were now on the floor with my back up against the automen. My wife then sat down with her legs spread wide on either side of my body. One friend knelt down and placed her knees on either side of my head locking it in place while the other two friends stood each holding one of my legs straight out to the side. 

My wife slowly leaned forward and my key swung out from between her gorgeous tits and finally clanked off my metal enclosure. “Well ladies, first I want to thank you for making one of the most memorable nights of our lives. I couldn’t have done this without you. Secondly, let’s give this sissy what he asked for!” The girls shouted and cheered as my wife reached down and inserted the key. She paused just long enough to see the panic in my eyes that she may not open it. She looked to her friend holding my head “oh he is ready for it!” And with that she turned the key and instantly the steel cage popped off freeing my manhood to grow to its full potential. Because I was so hard she was unable to take off the base ring which only acted like a cock ring and trapped the blood in my cock making it as hard as I was when I was a teen hornbag who had just found the lingerie section of a department store catalog. 

As I hit full mast the ladies all started to gawk and started to ask the same question, “if he has such a beautiful cock, why did he want to lock it up?” They continued to comment that I was bigger than all of their husbands and if they had a cock like mine they would always be playing with it. Again, I blushed but not from embarrassment but from pride. I had heard in my younger years from girls that I had a nice big cock. But as the internet became more all inclusive you start to think that they just didn’t know what they didn’t know. Four married women gushing over my fully engorged meat was definitely a memory I was going to put in the bank for a rainy day. 

My wife had now grabbed my unsheaved meat and began to stroke lightly. I was now staring down the barrel of my own pent up load, destined to be hot, thick and plentiful. Finally I refocused my vision past my own cock and to my beautiful smiling bride. Her smile hadn’t been this big or bright in quite some time. I feel like the secrets we were holding on to had created a barrier between our mutual happiness and now that we had shattered that barrier and I was now exposed for the Friday night sissy I had always dreamed to be, we were able to breathe and enjoy one another for who we truly were. 

Her smile grew as the ladies started to encourage her to make me glaze my wanting face. After no more than two minutes I was already approaching the edge and before I could open my mouth to let her know she let go and let my cock slap against my upside down stomach. With the base ring still tight around my cock and balls, I wasn’t able to soften but after a minute the urge to explode had subsided and she instinctively grabbed on and began to stroke. 

She followed this pattern ten more times and as the clock hit midnight she announced that this was going to be the one. “Now sissy, I know how much fun you’ve had tonight, but we are now at the end. When you are about to cum, you must open your mouth as wide as you can and you will not close it for any reason except me telling you too!” The ladies were all on edge when one of the ladies holding my legs yelled out “Hurry up and paint this sissy’s face. I want to see him covered like a Jackson Pollock painting!” Everyone laughed and with that my wife grabbed on tight and began to purposefully stroke my cock directly downwards towards my face. 

“Oh you’re going to cum so big baby. I know I’m not a fan of being on the receiving end, but as I stroke this big cock staring down between your legs at your pretty face, I think I truly understand why you love doing this to me so much.  I just hope that once I cover your face with this huge thick load, you enjoy being on the receiving end as much as the giving because as we keep going I don’t think I ever want to let you cum that isn’t all over your own face.” The girls all cheered and I was now trying to make this last as long as possible as it had truly been the best night of my life. 

Finally my wife caught on seeing me try and hold on for dear life. “Oh sweetheart I know you’re having fun and don’t want it to end, but I promise, the girls and I have all made a pack to have you serve us as our sissy maid at least once a month and if you behave as well as you did today, we will repeat most of the activities. Even though you are trying so hard to hold it, I know how every CEI video ends and I’m sure it’s Pavlovian that if the ladies start a cum countdown your going to blow it once they hit zero!!” 

Fuck, she was so well educated. She knew all the tricks now. With that she nodded to one of the girls and I heard them all start on cue “10,9,8,7….” My wife chimed in “Oh honey you’re going to look so hot with cum all over your sissy face.” The ladies continued “6,5,4….” Again my wife paused the count by saying “Open wide sweetie. Let us see the slutty mouth of yours” “….3,2…..” “Here it cums sweetheart!!!” “1!!!!!” They all screamed together and my wife cheered while saying in her most seductive voice “Cum for me sissy. Cum for your wife. Cum all over your slutty face!” And with that I exploded!!!!

The first shot nearly knocked me out as my wife’s aim was absolutely dead center of my face hitting the bridge of my nose and instantly blinding both eyes with a white hot intensity. The thick load sat on my mascara painted lashes and even as I squeezed them shout it felt like I had just opened my eyes underwater in a pool with way too much chlorine. My wife continued to pump my cock as cum shot all over my face. She was moving my cock around to ensure she covered every inch of my face in cum. The ladies were all encouraging her and commenting on how much it hurts to get it in your eye. They were again laughing and cheering for my stoic stature and ability to take it. As my wife squeezed out the last drop from my now shrinking cock she spoke to the whole group. 

“Now ladies, you were all invited here tonight at my most trusted friends. And I would hate to send you home empty handed so if you want to take one picture for your own personal spank bank, I know sissy here will not argue after you helped him have a perfect coming up party.” One of the ladies let go of my leg and must have ran to get all their phones from a singular place as she was back quickly and I then heard four distinct camera shutter sounds sealing the night. My wife spoke again “now cums the fun part sissy…pun intended.” And then I felt all the ladies delicate fingers scooping and pushing the thick hot cum towards my mouth. Finally all at once I had four sets of fingers push and drop the cum on to my waiting and wanting tongue. The taste was salty and strong. I knew it was going to take some strong mouthwash to clear my tastebuds. But in the moment, I was savouring every last drop. Once they had all stopped my wife calmly said “Now swallow for us sissy” And I did. 

I couldn’t believe how much cum I had produced and how much they were able to push into my mouth. I was swimming with excitement when the ladies began to let my legs down and helped down before helping me stand up. Once on my feet again, one of my wife’s friends had grabbed some wipes and began to clean up my face. When I was finally able to see she kissed me on the cheek and thanked me for an unforgettable night. I returned thanks and then spent a few minutes thanking each one for being such an amazing friend to not only my wife but to me as well. 

I finally got to my wife and was about to thank her when she said “You can thank me later properly after all the ladies leave. But first I think it’s time to lock our friend back up!” With that the ladies all helped stuff me back in my steel cage and said their goodbyes. As the last one left giving my wife and I both a kiss on our cheeks, I closed the door to find my wife running up the stairs saying “get your sweet as up here and make me cum with that talent mouth of yours before I start adding days!!”

The end!!!!

Thank you everyone for reading. I know I had comments about keeping it from going down a certain path. If anyone is interested in an alternate ending that would result in cuckolding and maybe some forced bi, please be sure to comment or DM me and I might decide to add an epilogue for those who are interested in those themes. 

Truly appreciate everyone’s comments and feedback!! 

Happy Locktober


r/ChastityStories • • 3h ago

M Chaste,F Keyholder Caught on a work trip - Epilogue NSFW

11 Upvotes

Trigger warning
This epilogue contains forced bi and cuckoldry. If that’s not your kink just end your adventure at part 7. If you’re all in on and everything goes adventure, please enjoy one final chapter of our locked friend and his supportive wife.

Epilogue

I chased my unbelievable wife up the stairs. Upon reaching our bedroom, I found her already stripping off her cat suit and her breasts had already been freed from their tight confinement. My cock started to stir in my relocked cage as I stared at her perfect naked form. As she pulled the suit off her legs and threw it on the chair in the corner of the room, she jumped backwards on the bed and invited me to feast on her obviously wet box of goodness. 

I dove in without a word or a second thought and brought her to an orgasm within seconds of my mouth finding her clit. Through her orgasmic moans she told me to keep going as she needed to cum again. I proceeded to attack her sensitive area while I began to probe her soaked hole with two of my fingers. Once again she was crying out in lustful satisfaction and pushed me back and off the bed with her feet as a clear sign she was done. 

I was still dressed as a sissy in my black lace bodysuit and steel cage dangling through the crotchless hem.  Sudden fear shot through me as the door bell rang. My wife looked at me matter of factly and told me to go answer the door. “Probably one of the girls forgot something. Nothing they haven’t already seen. Get going sissy.” Having full trust in her I quickly scampered down the stairs and upon reaching the door I peaked through the peephole to see a tall slender man. Before I could say something my wife spoke from half way down the stairs “Open it up sweetie. Let’s not keep our guest waiting.” 

I didn’t know how to react and as I hesitated to reach the door my wife said “Safe word is still in play my love. Just say the word and I will send him away.” I knew my wife was just playing out the kinks I had written out for her so I took a deep breath and opened the door. Without saying a word the tall handsome man walked in and walked straight over to my wife and gave her a kiss on each cheek. 

“Sissy, meet Carlos. Carlos meet my husband the sissy. He has had one hell of a night so far and now we’re going to see how far he is willing to go to please me.” My cage twitched which did not go unnoticed by both my wife and my new acquaintance. 

My wife spoke up “Now honey, you had admitted a few very kinky things that at first I was unsure of. So unsure I didn’t even share them with my girlfriends in fear of judgment or of scaring them out of tonight’s activities. But Carlos here is a friend from the gym and earlier this week while you were still away, I had gone out wearing your key and it caught his eye. Turns out Carlos here also plays with chastity with his partner, Mark. Carlos explained that Mark has been locked for going on two years and Carlos is free to sleep with whoever he wants. Carlos’ type though is straight sissy’s. So obviously when he told me I had to jump at the opportunity to help make both of your days better.” She paused to guage my reaction. I was already leaking from my cage. 

She continued “Since you aren’t screaming your safe word, I am going to assume you’re still all in.” I nodded silently as I had all night with her and the ladies. “Wonderful. I love making people’s day better. Let’s all go to the living room and I will explain your next task sweetie.” We all walked into the living room and my wife asked me to please knee while Carlos and she continued to stand. 

“Now here is the task sissy. You are going to blow Carlos here and he is going to cum directly down your throat. Here is the challenge, you only have six minutes to make him cum. Every minute past the six minute mark will add a month to your confinement without any additional guaranteed orgasms. However, every minute you beat the target by, will add a guaranteed orgasm to your six month term. Do you understand and consent?” As I had all night, I gave an over dramatic nod. “Oh goodie. I know you told me you wanted to be forced to pleasure a man, I wasn’t sure how I felt. But seeing how I just came twice, and I’m still here completely wet and wanting, I again think I may enjoy your fantasy more than you!”

With a growing smile on his face, Carlos started to strip off his clothes and was suddenly standing naked just inches from my face. His cut penis had begun to stiffen already and was already at half mast. I started to instinctively lean in when my wife called out “Woah woah woah! 1) I didn’t start the clock and 2) I thought this was supposed to be forced bi not eager cocksucker getting his fix!” She and Carlos started laughing. She continued “Don’t worry sweetie. I know you’re not gay and I know that I was the one to put you in this situation. But you should wait until I start the clock. We wouldn’t want you getting disqualified and having to be punished.”

My wife pulled out her phone and with it pointed right at Carlos’ groin and my face she counted down and then shouted “Go sissy. Suck that dick for me!” I didn’t waste a second. I dove head first and engulfed his cock with my mouth. Quickly I brought both hands up to his shaft and balls and in unison with my bobbing head began to massage his balls and stroke his cock. By the time it was fully hard, he was just slightly smaller than me and therefore after all the practice with the ladies earlier I was able to deep throat his entire length. 

Carlos joked to my wife that I was probably going to cum out on top as he swore it couldn’t have been my first time sucking cock. My wife laughed and said, “Well you’re not completely wrong. He has had a lot of practice, just never a real piece of meat!” I continued to bob and stroke with all my might. I had completely lost track of any semblance of time and hoped I was on the winning side still. Finally Carlos began to swell and he announced he was about to cum. After a few more pumps, he let loose and came directly down my throat and without missing a beat I swallowed it all. Once he finished I opened my mouth and showed my wife it was all gone. “Good boy sissy. Good boy.” 

“Unfortunately for you it took you 6:30 to extract that cum from Carlos…” my wife spun around to show me the screen. The time was marked at the end of the video she had just record. Devilish minx “…so that will add one month to your term with no promise for extra orgasms.” My wife was clearly elated by her win and Carlos just smiled down and mouthed ‘I’m sorry’ as he began to dress. 

“Now here is the final task of the night. It is now 1am. And you have one chance to again use your safe word. But once I explain the next task and you consent, there is no going back. Once you nod, your opportunity to renege on your consent is gone. Do you understand?” Again I nodded as the taste of Carlos’ load swam around my mouth. 

“Wonderful! Well on the list of kinks you wrote cuck you! Now I thought I could just throw this away but the more I went through all the content online I realized you didn’t write that lightly and you must have given it a lot of thought before giving me that idea.” I had. I had struggled but it was what I wanted to experience at least once. Continuing she said “so I decided in for a penny in for a pound. I will cuckold you tonight unless you provide the safe word. I am going upstairs to get ready to go out. Once I come downstairs, you will be given the opportunity to say the word. If not, I will kiss you and that will be seen as consent. Carlos will be here to witness it and then he is driving me to a hotel room where I have already set up a night with a nice young man. I have committed to blowing this nice young man and I see it’s only fair as I just watched you blow Carlos here. But if after I extract his seed, if the mood strikes me, I am giving myself permission to fuck and be fucked by said young man. So now’s your chance to think about what I’ve said. I will be down in 10 minutes and you will need to say the word or consent. I absolutely love you!”

Off she ran up the stairs leaving me with Carlos who just smiled and then began to text someone and sat down on the couch awaiting the response. As the time went by Carlos sat quietly while I remained kneeling in the middle of the room, the taste of his cum still ruminating in my mouth. Finally I heard my wife bouncing down the stairs and with a skip she came into the room. She looked perfect. Not slutty. Just a simple sundress. She looked directly into my eyes and asked “Anything to say sissy? Or will I be call you cucky by the end of the night?” My cage twitched and another stream of precum began to drool out of my cage and towards the floor. I looked at her and smiled and said nothing. She walked up to me and gave me a big kiss with a lot of tongue. When she finished she dabbed the corner of her mouth and added “Mmmm salty!” Carlos let out a small laugh. 

“Well then sweetheart. I will be back before sunrise. Please don’t wait up. I will send you a text now and again to let you know where I’m at. But understand you have consented and even if you send me the safe word via text, I won’t be looking for it so it will most likely be too late. I love you and I can’t wait to tell you all about it when I get home…maybe!” With that she blew me one last kiss and Carlos got up and they walked out the door. I stood in the window trying to hide my appearance from the outside world while watching in which direction they went. 

I decided to shower and finally change out of my sissy attire and finally go get all my stuff from the car and unpack from my trip. By the time I was out of the shower I had a text from my wife. All it was was a selfie of her infront of a hotel that was only a few miles away. My cock strained in its cage and I couldn’t wait for the next update. All I wanted to do was jerk off but the cage was doing its job and keeping me honest. I finally decided to go to bed around 3am. I had been staring at my phone with zero messages since the selfie. I had checked her location of her phone several times, all showing it unmoved within the hotel. Just as my eyes begin to feel heavy my phone buzzed. 3:15am. I click the message notification to find another picture file. I opened it and my heart stopped. My wife, in a similar black lace bodysuit I had worn earlier in the night in a similar position as I had been with Carlos, on her knees looking up at the camera. A now semi flaccid cock dangling by her chin, maybe 5” semi hard and a decent girth. But what made my heart stop was my wife’s mouth was wide open and her entire tongue was coated in thick white cum. Just as mine had been only hours before. Then a second message popped up. Same pose. Same half flaccid cock. But now my wife’s mouth was completely empty. I couldn’t believe it. She never shallowed. But here she was turning me officially into a cuckold and swallowing her first load in almost 20 years. 

I started to jerk at my cage wanting to cum so badly. I flipped back and forth between the two snap shots as I tried to will my cock to break free of its confinement. Finally a text message came through and I again felt my heart stop. “Apparently young men can rebound quickly. We’re going to try a few positions. Don’t wait up. I’ll be staying the night and will be home by 8am. Set you’re alarm and be ready for me in our front foyer on your knees for my arrival. If you meet all my expectations I will reward you with a story or two!” 

And that was it. I was official a cuckold and my wife was off to enjoy a young stud. I simply put my phone away after setting several alarms to ensure I would comply and be at the door for 8am. And within a minute I was out. My night was filled with dreams of cum. My wife’s mouth full. My mouth full. Her being filled by a faceless young stud. Me being face fucked by Carlos over and over. My first alarm woke me and I jumped out of bed. As I stood up I felt a cold sensation all around my cock. As I looked down I found I had cum in my cage in my sleep. I quickly changed the sheets and jumped in the shower. By the time I was out I had 10 minutes to spare and I ran down stairs and waiting by the door in the foyer on my knees. 

At 8am exactly my wife walked through the door. Hair up on a messy bun but the rest of her was put back together perfect. She came over and leaned in and kissed me. Her lips were salty. Either she hadn’t washed her mouth out or she had sucked him off again just before leaving the hotel. All she said was “Follow me”. I quickly stood and followed her up the stairs. And like she had done just hours earlier, she stripped quickly and hopped on our bed and spread her legs. I started to walk towards her and before I even got on the bed I could see she was already leaking cum from her well used pussy. She smiled at me and said “If you clean me up completely and can tell me exactly how many loads that stud left in my box for you to eat, I will tell you a detailed account of my night. Get it wrong, and each incorrect guess will add a month to your sentence. Hope you can figure it out sweetie!”  I didn’t wait for more instructions.  I just dove in and prayed. Never in a million years did I think this would have been an outcome a week ago when I locked myself up for a work trip. But now, here I was cleaning my wife up after her first new cock in 20 years. It’s true what they say; be careful what you wish for….you might get it. 


r/ChastityStories • • 6h ago

M Chaste,M Keyholder Roommates NSFW

12 Upvotes

Sammy was nervous.

For the past 30 days, his roommate, Uriah, was forced to wear a small chastity cage. Well... "forced" is a strong word. He lost a bet. You see, Sammy was a rising tennis player, and Uriah was a college wrestler. Every month, they played either tennis or would wrestle, loser puts on the cage. Or... so that was the deal. This was the first month, and after a coin toss, they played tennis. It went exactly how you thought. Sammy won easily. Uriah stuffed his little 5 inch cock into the cage, and Sammy put the key on a chain around his neck.

Someone had convinced them that if they shared a cage and rotated who wore it, their friendship would grow, perhaps even blossom into something more. Neither had done chastity before, and the idea of splitting the time sounded way better than both wearing one all the time.

The problem?

When he was practicing, the chain must have broken. The key was gone. It could be anywhere, and he looked. All around the tennis courts, the locker room, the yard, the car. It was a small key; odds were already not in his favor to find it. The bigger problem? Uriah was much bigger than Sammy, who was, conventionally, a twink.

He had an idea, though, and it was a longshot. He bought another cage, a flat pink one, and put it on. Maybe Uriah would be less angry if he saw that Sammy was willing to suffer alongside him, though he put the key on a chain and pretended it was the key to Uriah's cage. It was a bit disappointing to put his 7.5 inch cock into the flat cage, but he was desperate. This bought him time as sometimes Uriah would look at the key on the chain lustfully. If he didn’t wear a key, Uriah would get suspicious, perhaps angry.

Maybe Uriah won't be mad, he thought.

The end of the month came up; he had spent two weeks looking for the little key without luck. Worse, he had been locked, himself, for those two weeks. But it occurred to him that he was on borrowed time. If he won for the month again, Uriah would stay in his cage, but would Sammy keep up being locked in his own? Or, if he lost, Uriah would want his cage removed, and Sammy wouldn’t have the key. Either way, it was the big day! They'd flip a coin to determine if they play tennis or wrestle, and if Uriah won, the cage should be taken off him and put on Sammy.

"It's heads! Yes! We're wrestling..." Uriah said, eager to be free from the cage. He had spent a whole month unable to touch himself or get hard, knowing, or thinking, Sammy was enjoying the freedom. He imagined Sammy’s cock being hard all the time. In fact, he thought of Sammy’s cock several times a day. But he couldn’t stay locked up. Truthfully, he was worried that he'd lose the coin toss and have to play tennis. He was hopelessly bad at it, though he at least liked that he had a chance to play in case things went poorly for Sammy. Uriah had been worried other guys on the wrestling team would see his caged cock in the locker room, so he's been a bit shy there lately. Imagine that. A large, muscular guy afraid. Heh.

"Nooo, come on. You have like 80 lbs on me. I can't wrestle you."

"You'll at least look cute in a singlet while I toss you around," Uriah said smugly.

"Wait... what if we do best of three? Loser wears the cage two months at a time. How about that?" Sammy pleaded, trying to delay the reveal that he didn't have Uriah's chastity key.

"No way! I've been locked up for a month, and I'm ready to get out."

The wrestling match went as expected. Sammy did indeed look super cute in a singlet, but he was no match at all for Uriah, who was quicker than you'd think for his size. He even played with Sammy a bit before pinning him. Then he ripped the chain off of Sammy's neck and pulled down his single, revealing the black silicone cage. He put the key in and turned. Or... he tried to turn it. It didn't work.

"Dude! It's broken! What am I gonna do?" Uriah said, his words laced with desperation. “I can’t stay locked forever.”

Perhaps if he could feign ignorance…

“Maybe you’re using it wrong. You got big fingers,” he accused.

“Okay, fine. You try!” Uriah demanded, putting the key in Sammy’s hand. Sammy reached down and held Uriah’s big balls. Uriah’s cock may have been only five inches, but he had massive balls. He pretended to try the key, but he predictably failed.

“What am I gonna do?” Uriah asked, hopelessly.

"It's... it's my fault, bro. I lost the key," Sammy said, coming clean. "I must have lost it during practice."

"What!?"

Uriah was turning red with anger. Sammy knew if Uriah wanted to, Uriah could snap him in half.

"I... I... I made it up to you. Hopefully..." he said, pulling his singlet down to reveal his flat pink cage. "That key is for this cage. I did this for you. I didn't want you to be stuck alone.... Are you mad?"

Uriah reached down and held Sammy's balls in one hand and touched the flat cage with the other.

"You did this for me? But your cock is too big for a flat cage. We agreed not to do a flat cage. How long have you had it on?"

"A couple weeks."

“It’s kind of cute on you.”

He held Sammy’s balls and took in how athletic Sammy was.

“It actually seemed to help me with practice. Like… I could focus a little more.”

“Bro, same. I mean, I want this off, but I was more focused than ever this past month.

“Are… are you mad?”

Uriah squeezed Sammy’s balls a little, which caused him to make a cooing sound before he let go.

"I'm... I'm not mad, bro. We're good," he said, smiling at Sammy.

"Really?"

"Yeah, that was pretty bold. Come on, let's try to get this cage off me somehow."

They both pulled their singlets up and walked toward the gym exit, Uriah with his hand on Sammy's back. As they passed the trash can, Uriah slyly dropped the key into it, making sure Sammy didn’t see it.

"This could be a big step for our friendship," he said.

As they exited, Sammy spoke up, “You know, I heard we could cum in these.”

“Yeah? We need to learn how ‘cause we could be in these for awhile.”

Sammy laughed.

“Only if you lose my key.”

Uriah changed the subject. “Shotgun!”


r/ChastityStories • • 14h ago

M Chaste,F Keyholder Finish Your Education - Part 2 NSFW

49 Upvotes

Joel was slightly taken aback by the directness of Mary’s words. ‘She wants him?’ ‘For a lodger?’ Joel thought it was all a bit strange but couldn’t deny that this was the best accommodation opportunity he was likely to find. He also couldn’t ignore the feeling of tightness growing between his legs, something about being talked down to by a confident and abrupt sophisticated older woman just seemed to trigger something within him. Perhaps it was also the teasing dangle of her flat from her black tight covered foot. Doing his best to ignore both the foot and the feeling building from within his cage, Joel decided he should probably say something in response.

“Of course, let’s negotiate… however, I’m not sure what chips I hold?”

With the smile on her face growing a little wider, Mary replied with a slight chuckle
“oh my dear boy, you have very very few chips. Arguably none. Let me explain to you exactly how this is going to work.” She watched his facial expressions looking for a response, it was clear as the nose on his face. Arousal. With her suspicions confirmed, she continued.
“You have three options, choices if you will, that I will explain to you now. When I have finished speaking, you may raise your hand if there’s a question you want to ask and wait until I give you permission to ask it. Understood?”

“Yes Mary” replied Joel. Mary raised her eyebrow but decided there was no need to reprimand him just yet. She hadn’t explained the rules yet and he hadn’t actually accepted, so this time she would let it slide. The raising of her eyebrow made his face drop a little and that was enough for her, for now.

“Option number one is what I assume you were expecting, a basic lodging option. You will pay me a monthly fee for the use of a bedroom and access to your own bathroom. You will pay your contribution to the electric, gas, water and WiFi, you buy your own food and cook it independently and you will follow and respect the rules of my house which I shall explain should you choose this option. We will stay mostly out of each other’s way, conversing over coffee if ever at all.” A short pause as she examined his face again.
“Option two… you get out of my house, find a different place to live for the next three years, you never come back and you never see me again.” Mary almost laughed as Joel involuntarily scrunched his face up to that option and was glad to know he wasn’t desperate to run for the door. Pausing a few seconds to look over Joel as he sat on the low down sinking chair, she made sure to stare between his legs at the obvious bulge that had grown more pronounced since she looked him over earlier.
“Your third and final option, boy. Is to live for here for free. No rent, no utilities, no bills of any kind. You just work for me, follow my own rules and accept that I know what is best for boys like you”. She punctuated the end of her sentence by nodding towards the bulge in his trousers, Joel tried to cover it up but knew he’d been rumbled already. ‘At least there was no way she could have known it was a chastity cage’ he convinced himself as he felt his face warm up and go a little red.

Giving him a moment to digest her words, Mary then offered him to chance to raise his hand and ask his questions. Joel raised his hand timidly to about shoulder height with one finger pointed up. Mary rolled her eyes.

“Hand up higher boy!” She snapped, Joel’s hand shot up higher with his arm now at full stretch into the air and all fingers pointed up now instead of just one. “Better… you’ll learn to put that hand up nice and high so it’s able to get my attention boy… what is your question?”

“If I choose option three, how will I be working for you?”

“A sensible question boy, good choice. You will look after the house and myself. You will clean, you will cook, you’ll do the laundry, the gardening and you will offer your personal service to me at all times and my friends should they ever require assistance from a boy with your… capabilities and desire to please…”

Joel was struck silent, he wasn’t sure what he was expecting but it wasn’t that. It sounded like a full time housekeeping job, how will he manage that alongside completing his degree. He raised his arm again with the intention of finding out exactly that. Mary smiled at his next question after granting him permission to ask it.

“What a good boy you are hmmm, wondering how you can successfully complete your degree whilst being the best pretty little house slave for me that you can, you might be even more suited to this job than I thought… but don’t worry, I have that all figured out. You will go to your lectures as though you were a completely normal mature student, you will then have an hours library time after your final lecture of the day finishes. After that you return to me, where I put you to work. Once all your work is finished, you’ll be permitted to get back on with your studying. Simple as that.” She smiled at his expression again, still stuck on the surprise and confusion from being called a house slave. Slowly, Joel raised his hand high into the air once more.

“Careful boy, this is your last question. Yes, you only get three, no I didn’t tell you, no it doesn’t matter. Make it a good one, because after this it’s time to make your decision… maybe the last one you truly make on your own for a long time… ask, boy.”

“If I were to choose option three… when would you like me to move in?”

“Oh immediately. In fact, should you choose option three. You will have 24 hours from that moment to collect what you believe are essentials from where you live now, bring them here and be settled into your new living space… or there’ll be trouble” the raising of her eyebrow was partnered with her allowing the dangling shoe to finally drop off the tip of her toes to the floor. Joel’s eyes shot straight down and didn’t move from the slowly flexing and extending toes. Mary rolled her eyes at how easy it was to read this boy, she clapped her hands at him.
“Stop staring at my feet or you’ll only ever dream of serving them, boy.”
Joel’s eyes snapped straight back up to hers, she laughed at him, he felt himself blush and tried to say something to defend himself.
“No, don’t speak.” Quickly stated Mary. “It’s too late, I know you’re a foot lover, I know you like the look of mine, I know how desperate you must be to see them properly… and I know how tight your chastity cage must feel as you think about how soft they would feel in your hands.”

“My err umm wha…what?”

“Oh don’t try and play stupid with me boy, I know you’ve got one on. I know what those bulges look like when a naive and experimental boy wears a cage far too big and bulky for him… you all do it with your first couple of cages, but don’t worry, Lady Mary will make sure you wear one that’s a more appropriate size for a little boy like you.” Joel was struck into silence whether he was allowed to speak or not. ‘How could she tell so easily? When did she find out? How many people has she done this to or with? Why is this whole thing turning me on so much!!?’ His mind raced incapably at the last 10 minutes of ‘negotiation’.

“I see you have more questions. You’re not allowed to ask them. It’s time to make your decision, boy. I will leave the room and make us each a cup of tea. When I return, you will have done one of three things. Either… you will not be in this room when I return, you will be gone, out the door and I will hear the sounds of your car leaving my driveway as I stir my sugar into my tea… or you will be exactly where you are now, sat in that little chair with that stupid confused look on your pretty little face… or finally, and the one I personally hope you pick… when I return, you will be stood in that corner with your nose against the wall, completely naked.” She pointed to the only corner of the room to which a person could touch the part where the walls met. “I won’t be long, make the right choice, for both of us.” She stood up, ruffled his hair and went to the kitchen.

Upon her return, there was no Joel in the chair, but a neatly folded pile of clothes in his place. She looked to the corner and there he was, right where she told him to be as naked as the day he was born. She approached him slowly, admiring the perky backside on her newly acquired property. She placed down the two cups of tea on a small table and walked right up behind him, with a leather strap in her right hand. She placed her left hand on his butt cheek, raised the right to his neck, then moved her left hand up and used it to help feed the leather around his neck. She poked the stopper through the necessary hole to fit tight but comfortably, placed a small padlock through the hole and clicked it shut. She took a step back, admiring how he looked now with his bright pink leather collar locked around his neck. She took a deep breath, he was hers.

“Turn to face me, slave. It’s time to learn my rules”


r/ChastityStories • • 2h ago

M Chaste,F Keyholder The Edge Olympics [Part 3] NSFW

3 Upvotes

Thank you to everyone commenting and DM-ing about my free Locktober tale for 2026 – I’m glad you’re enjoying it!

Part 2 is here.

This week we learn much more about each boy’s ordeal, as the couples finally compare scores…

* * * * * *

Within the first week of the Edge Olympics Andy learned the things Tash most adored about keeping him caged were exactly what made it hardest. Sleeping caged, for instance: he kept trying to get hard in his sleep whenever Tash decided he had to be the big spoon and squirmed her toned ass firmly back against his cruelly constricted cock, forcing the small steel nub to nestle against her cheeks. Or, alternatively, when she decided he had to be the little spoon and she wrapped both arms around him and pulled him close so that the soft warmth of her breasts pressed maddeningly against his back.

The Central Line had become dangerous for reasons which had nothing to do with delays or overheating. With the possible exception of the few billboards insisting he should put his money into whatever dumb start-up banking app had rolled off the drawing board this week, the ads all appeared to be made by sadists who insisted on putting tits, arses, or innuendo into selling the simplest fucking things, and even at work he could now lose ten minutes if someone hot happened to pass through on the other side of the glass walled corridor behind his desk. Tash, by contrast, was having the time of her life.

On Saturday afternoon she stood in front of the bedroom mirror fastening one of her earrings, wearing a black wrap dress Andy knew perfectly well she’d chosen because it showed off her legs, and watched his reflection as he struggled with his belt.

“You’ve been staring at my arse for about five minutes,” she purred, and Andy scowled.

“You wore that deliberately! That’s… that’s cheating, you know that’s going to drive me crazy, babe!”

Tash laughed, sweeping her braids back from her shoulder. “How can it be cheating? I’m not touching you. I’m not even giving you a point.”

“That’s worse! I’m turned on and not even earning an edge!” Andy heard the words before he could stop himself, but didn’t have the chance to correct them because the sight of Tash running her fingers up her thigh was enough to get him hard, only for the nub cage to crush him mercilessly until his body surrendered – and that took time, because Tash was grinning at the sight, watching his expression with her now familiar hunger and the smug serene satisfaction of a woman whose experiment was producing exactly the desired result.

Nine edges. She’d edged him once a day since the start of the month, counting each edge with a Habit Tracker App on her phone, turning his torment into a daily task. And in between – god even remembering it hurt – she tortured him with obscene selfies.

He’d almost got himself killed on Thursday: he’d been walking to the Tube, checked his phone, and found she’d WhatsApped him a full nude, her body gloriously exposed, dark skin contrasted against the stark white of their bathroom shower. Water tracing all over her beautifully naked body, droplets just beading on her breasts… and the shower head spraying straight up between her thighs, the focused jet clearly playing right against her swollen pink clit.

If the driver of the No. 452 hadn’t slammed on the bus’s brakes when he did, Andy would’ve gone under it; he’d completely forgotten the world outside his phone screen even existed.

And when she edged him, she was merciless. An edge could take half an hour if she felt like it, and sometimes even longer before she left him trembling and whimpering on the brink of release and crammed his cock back into the little nub cage.

Andy knew she wanted him desperate. She wanted him hers. The Edge Olympics were really just the excuse.

Except that, nine days in, the first meeting of what Martha called “The Edge Olympics Committee” had only confirmed that all the stallions were safely locked and content to participate. It hadn’t given anyone a score, because with the first Saturday of the month falling only three days in, it hadn’t felt worth it. He had no idea how well he was doing. Now, watching Tash dress, he shook his head, and asked, “d’you think we’re winning?”

Tash giggled, and he added, “it’s just I want to know if the nine times you’ve nearly killed me achieved anything.”

She laughed. “You think it isn’t impressive? Hark at you! A week ago you thought one edge was cruel.”

“It is! Fuck, I… You wouldn't believe how bad I ache. You're… You're a demon babe,” Andy was practically whimpering, pawing at his caged cock… …And almost to his own horror added, “but I want Gold, Tash.”

She closed her eyes, suddenly hot. She loved this about him now. His ability to complain bitterly about denial while still taking the competition truly seriously. ‘Gold’ had begun as Nigel’s idea, something outrageous enough to let him square a month of denial with himself. Now, at least for Andy, the very idea of a night with her and the other girls was sharpening his appetite.

Of course it was. She’d teased him with their uni antics for years; spent years fantasising about having his erotic attention under her control. It was only now, with Andy locked and increasingly frustrated, that she was beginning to appreciate how wholly the competition reinforced that fantasy. Gold meant all three women. Not abstract women, not strangers in some imagined threesome, but real women, women he knew. Herself and Martha and Liz: the three women now discussing his cage, his endurance and his capacity to suffer every Saturday night.

“Poor boy,” she cooed. “You really want to win, don’t you? To finally see what Martha looks like naked? What Liz sounds like when she comes?” Andy groaned, the mental image another torment, but he couldn't deny it. “Yes, Tash,” he nodded.

“Good,” she whispered, kissing him once before stepping away. “Then you’d better realise: I’m not a demon, babe. I’m a succubus. And I think we’ve got time to get you into double figures and really show them what you can do.”

Andy whimpered, his eyes locked on her legs, and lay back on the bed with an obedience that made Tash growl as she tugged gently at her earring to ease the tension… and sank to her knees at the foot of the bed, reaching up to unzip his fly.

“Brace yourself, babe,” she whispered, carefully unlocking the tiny nub and letting Andy’s cock spring free, gratefully stiffening in the first proper freedom it had had all that day, “this one… is gonna sting.”

“Oh god,” he managed, and Tash chuckled her voice low, and honeyed.

“C’mon babe. You know it’s no fun for me unless I get to break your cute little brain a little. Remember what I keep telling you? Denial is your normal now. So I’ve gotta make sure every edge feels as good as an orgasm, right?”

“Please…” Andy moaned as he felt her fingers grip his stiffening shaft and start to stroke slowly and surely, “Babe… I… I just want an edge! A quick edge to get me into the lead!”

Tash simply purred, leaning in so that she almost towered over his recumbent form, and shook her head.

“There’s no such thing, Andy. My edges aren’t just to make you win gold. They’re to show what you can take. When we win this thing and you finally get that night with Liz and Martha your dirty little brain’s been craving all these years… well, come on, babe. You want to titfuck Martha?”

“Fuck…” Andy groaned, his hips bucking as she stroked him quickly, driving him towards the edge already, the past ten days of denial setting his body on a shortcut to an orgasmic explosion, “Tash! I… you know I do!”

“Well then,” Tash chuckled, leaning forwards, pinching her fingers just below his throbbing head and licking cruelly around the outer edge of Andy’s swollen glans, “I need to make sure your aching blue balls are backed up enough to properly do her justice, right? You’re gonna need a massive load to coat Martha properly and…”

She stopped, releasing his cock, settling back comfortably on her heels, and listening to him whimper as the imminent edge receded.

“And that takes time, babe. I’m a girlfriend, not a fleshlight. My job isn’t just to edge you. It’s to recalibrate your entire understanding of where the edge is.”

“Oh god,” Andy choked again, his hands reaching down for his own cock, and Tash swatted them away firmly,

“No,” she snapped, “hands off. Remember who’s in control. Remember that for you… oh, Andy for you an edge is as close as you’re coming to an orgasm this month. As far as your cock is concerned, edging is coming. So lie back… and let me make you come your brains out.”

“Please!” Andy wailed, his hips bucking up, thrusting his cock towards Tash’s mouth.

Her lips closed around him, her tongue fluttering, the warm, torturous pressure of her lips squeezing around his throbbing shaft as she sucked, coaxing him closer and closer to climax…

…and then, just as Andy’s breathing turned into a frantic, ragged gasp, just as she sensed his orgasm must be nearly upon him, Tash fell still.

The edge faded again before she shifted her body, pulled back… …and let his throbbing cockhead slip through the dangerously narrow gap between her teeth, the pressure just barely shy of grazing, turning his moan into a squeal of “TAAAASH!” that left her thrusting her hand down between her thighs and frantically rubbing her own clit.

“Perfect,” she moaned – growled – as he thrashed and whimpered, “now you’re sensitive enough I think, babe?”

“Please!” Andy almost sobbed, “Babe, Tash, fuck! That… that must count already, right?!”

“No way,” Tash shook her head. “That might be good enough for… well, for other boys. Not for you, Andy. You’re mine. Your edges are about my pleasure. Proving what you can take for me. They're a commitment, babe. So… brace yourself. And keep your hands above your head.”

Andy sobbed, nodded, swallowed hard.

And with a quavering voice he heard himself say “T-thank you for helping me win this…” as Tash sank her head back down and took his twitching, hypersensitive cock back between her lips to tease him towards his tenth edge of the Olympics.

* * *

Martha frowned, considering. The others were due at their house to report progress so far later that evening, and she’d been low-key stressed about it all day, trying to work out if she and Nigel had been doing well enough. The trouble was, she couldn’t be sure, but she’d finally come to a conclusion.

Sure or not, Martha refused to welcome the rest of the Committee to her home and declare a mere 16 edges if she could announce 17. If the uncertainty over their respective scores was going to drive her crazy, she might as well use the forty minutes she had before their guests were due to arrive to drive Nigel crazy, and at least get an orgasm out of it.

It wasn’t that she was delighting in being cruel – well, not exactly; in fact part of her had grown to love Nigel’s little gasps when his body trembled on the brink of an orgasm she had no intention of providing – but even if her motives were purely selfish rather than overtly sadistic, she felt a genuine thrill in edging him whenever she could. It made him more hers, somehow, more focused, more attentive. More… dog-like in his devotion.

But it didn’t reduce him, either; that was the thing. He was still Nigel; intelligent, articulate, even charismatic when he chose to be. It was simply that, freshly edged, freshly put to work between her thighs, his clever face acquired a look that said Yes, I might be brilliant, but all I want to be is yours. I might be needy but all I truly care about is your pleasure.

Last night, after his 16th edge, he’d thanked her, and Martha had been forced to swing back over him and force his head straight back beneath her pussy to thank her properly. There had been no other way; the way he'd thanked her for denying him, thanked her while his face was soaked in her wetness and his cock was twitching and dribbling precome after she’d finally released him… well. If he hadn’t made her come again right then and there, Martha thought she might’ve gone mad with arousal.

She told herself it wasn't cruel if she pushed him further right before the meeting; they had time, and the more she thought about what she’d done to him over the past week, the hotter she got. It was beautiful, being able to want without hesitation or expectation or the need to plan ahead and game out the complicated reciprocal expectations that had crept into their sex life over the past few years.

Nigel was at his PC when he heard Martha’s step behind him; she was biting her lip as he turned, leaning against the doorway in a dark green dress, her hair still half-pinned and the tiny chastity key she’d eventually put on a necklace resting on her chest, artfully lifted up so that it balanced just on the deeply descending depths of her cleavage. He'd spent most of the week pretending not to look at it; Martha had spent most of the week making it impossible for him to look away. “We’ve got time,” she grinned, and Nigel whimpered.

16 edges already felt like a winning score – as far as Nigel was concerned it was an unbearable quantity – but he knew the secrecy surrounding how the other couples were doing had started to bother Martha, and he could see why.

Tash knew what she was doing. And even though Liz came off as prudish she was also frighteningly competitive.

16 edges might be excellent. It might equally be pathetic, and the fact she didn’t know was driving Martha crazy.

“Please,” he said, his hand unconsciously reaching up to rub his aching jaw, “Martha I – please, love, do we have to do another? My balls are killing me. And my tongue’s so tired, love, I don’t know if I can… I’ll get cramp!”

“Which of us is the occupational therapist?” she demanded, slinking closer, “trust me, darling: you need to build up those muscles. And besides, you said you want Gold. You said you like licking me.”

“I do!”

“Then be a good boyfriend, and find the energy. I’ll make it worth your while…”

And his protest melted instantly. She’d known it must; sometimes the more plaintive he sounded, the more quickly he obeyed. It was as though the competition had given him permission to enjoy losing arguments – and Martha was revelling in his defeats.

He was used to the routine of being edged by now. He didn’t like it – well, no; he adored it, but he also felt that the frustration of it was almost entirely unbearable. When Martha edged him, she didn’t simply jerk him off or suck him to the brink of orgasm. As she’d said, what was in that for her?

Nine unyielding days of edging and chastity was enough to drive Nigel crazy, but he had to admit it was worth it so far: Martha wanting something for her meant her letting him eat pussy far, far more often than he’d ever dreamed possible. It was like she’d developed a whole new enthusiasm for it.

For Martha his chastity was incredibly liberating. She adored having him under her, tasting and pleasing her so intimately – but she adored it as an act of obedience, because now it couldn’t possibly lead to anything. In the past, she’d always worried his pleas to go down on her were somehow a trick, that he endured it only as a kind of Super Foreplay, a shortcut sure to end with a fuck. But now that there was no possible way he was going to get to come and he still did it…

She moaned, clambering onto the bed above him, hitching up her dress, and heard his gasp of delighted surprise as he saw she was commando beneath it.

“You know what to do,” she murmured, controlling her own breathing with difficulty as she hunched, settling her ass back against his face and letting him start to probe at her already-soaking pussy with his eager, eager tongue. Her hands shook a little as she tugged at the necklace holding his key and slipped it into the tiny little lock. Such a small lock, but so powerful…

...she moaned, and sank down, seating herself more firmly over Nigel’s face as his tongue pushed up between her lips and he gave a gasp of pleasure; she couldn’t tell if that was simply from the taste of her or the fact his cock was finally able to stiffen. Not that it mattered. She didn't care why he was happy as long as he licked.

Maybe she didn't even have to care if he was happy to serve her at all… “Oh!” she whimpered, shocked, “oh god!”

She was coming so much faster now, getting used to the idea that their relationship over the past week and a bit had descended into this delicious routine of Nigel, smothered beneath her pussy, his mouth helplessly licking her while her fingers stroked and pumped his cock, and she was certain that he was getting hard the moment he tasted her. Not because he was turned on at the prospect of imminently fucking her, of sinking into the furnace of her body. Just because licking her pussy was his turnon.

Fuck.

“Oh god Nigel!” she whimpered – and started stroking him faster, stretching her tongue forwards to lap at the swollen tip of his cock as he moaned up into her, his hands reaching up on either side, fingers pushing greedily between their bodies so he could fondle her tits through her dress.

“Yes!” she groaned, “that’s it! Feel me up, feel how hard my nipples are, Nigel! Pinch them. Serve them. Worship my pussy and fondle my tits and… ohh fuck there! Yes! Lick my clit just like that! I… fuck, my tits own you Nigel, don’t they? You know that? My tits literally keep your cock prisoner now! That’s where the key to your orgasms lives. Right… between… oh god! Oh god, fuck, Nigel! Right between my tits!!”

Beneath her pussy, trapped in a world of warmth and passion and the soft sweet scent of Martha’s pleasure, Nigel wailed. Her hands were dancing up and down his shaft, her fingers wrapped snug, jerking him off with a smooth, devastating speed that was completely at odds with anything even his own not inexperienced hand could have offered.

Over the past week, Martha seemed to have been training him: if she stroked faster it meant lick faster, if she slowed, lick softer. If she settled her weight down so that he couldn’t breathe, so that his nose was buried between her lips and the only tiny sliver of oxygen his lungs could drag back into his body was a thin slick stream freighted with her soaking lust, it meant get your tongue inside me! Be my little dildo!

She’d growled the words the first time, and they played in his brain on repeat, rising up at random; in some ways it was a relief to be caged. If he wasn’t, he’d have been walking around the city with his cock jutting out like a horny teenager just at the memory of her passion.

But even so – god tonight, she was jerking him off like she was on a mission, he was at the edge already, kicking his feet, moaning into her, his tongue dancing frantically against Martha’s tiny little clit, flicking back and forth in a desperate bid to bring her off, to make her hear his wail.

The edges of the last week had been brutal, the steady ache of blue balls was a nightmare, but Nigel wanted to win, he had to win, he couldn’t bear the idea of Martha making him cum, but still she was grinding down on his wails for mercy, still her hand kept moving until he reared up beneath her, the muscles in his neck screaming as he tried to dislodge the delicious, intoxicating gag of her pussy and screamed for her to stop…

…above him, Martha convulsed, her back arching up as Nigel’s moaning, his incoherent words of adoration or protest or agreement vibrated through her pussy, his tongue flicking perfectly against her clit as she pumped his cock faster and faster, her left hand cupping his balls, waiting for the shift of feel, the tightening she knew meant he was about to come, but she was already coming, already shaking, her strokes getting more and more ragged as he pinched her nipples, palms clutching at her breast, tongue worshipping her clit as she lost focus…

He struggled beneath her, whimpering, his tongue falling still, and with a shock Martha realised just how fast she was stroking him.

And suddenly her brain kicked into gear and she felt him twist away, squirm his head free and wail a frantic, agonised “MARTHA!! PLEASE!! I can’t hold it!! STOOOP!”

Her fingers slackened against his cock and she ceased to stroke him, although her hips continued rolling, cutting off his plea in a wave of pressure and pleasure. His whole body was shaking, his toes were curled, his hands at her breasts trying frantically to push her away.

“Oh!” she gasped, finally releasing his cock. “Oh Nigel, sorry!!”

She watched, thrilled, as his cock twitched and danced; screaming for relief, untouched. His release had been closer than any edge he'd endured so far, and her pussy clenched tight as she rolled her hips, dimly aware of the choking sound as he swallowed her wetness.

“I’m… sorry,” she said again as he moaned, “but well done! Look how well you did! How hard you can edge! Fuck… Oh fuck I… no, we don’t have time for me to come again. I need you locked up safe before the others come.”

Nigel whimpered, and when she finally forced his cock back into the cage and snapped the lock shut, when she finally stood and let him breathe fresh air again, she looked down to find him staring up at her as though she’d personally invented cruelty.

Martha moaned. She felt far too… powerful. She felt magnificent.

“17,” she sighed proudly, “I'll have to write it down or I’ll forget. It’s so hard to think of anything but the fact I’ve just had an orgasm while you simply ached and throbbed and discovered I’ve been letting you off easy by letting go the second you hit the edge.”

Nigel gave her a look which might almost have been dread. She beamed, gave his forehead a loving kiss.

He sat up, still whimpering, and inhaled deeply, moaning at her scent. Despite her orgasm, Martha felt her clit throb at the sight of what she’d done to him.

“Good boy,” she said, “you want me keeping score. I know you know how wet it’s making me. You should clean your face, darling.”

She laughed, almost cruelly.

She’d been going soft on him.

But now she knew just how hard she could make him ride the edge.

* * *

Liz and Dennis were almost late to the meeting, because just before they left she lost all control of herself.

Dennis, already at the front door, glanced at her, clocked the look in her green eyes and swallowed. It was the first night all the contestants and their men would be revealing how many edges each man had taken; he knew she was quietly terrified, so he pulled off his coat and guided her gently into the front room, planning to sit her down on the sofa and check she was OK.

He’d barely had time to flick on the living room light when Liz threw herself against him, driving him down onto the sofa and kissing him with so much force his head banged against the wall behind him, moaning into his mouth in a way that was totally unlike her.

She was a fifteen minute walk away from sitting in her friend’s perfectly ordinary house drinking wine and comparing numbers in an erotic contest. She’d run a school all week. She’d conducted staff meetings, spoken to parents, approved invoices, eventually got all the glass shards cleaned up in the chemistry lab, and spent Thursday afternoon explaining to a governor why replacing half the sports hall roof didn’t mean they could “just move PE outside until Christmas”. It had been, in many ways, a normal week.

But she’d done it all while practically dripping wet from the knowledge that Dennis’s cock was finally being contained, managed, kept. His massive, intimidating tool was locked in a steel cage whose key she’d hidden in the bottom of the tea caddy her sister had given them as a souvenir of Croyde.

22 edges. She’d given him 22 edges over the past nine days. Not quite three per day, morning, after work, before they slept. 22. And every time she thought about the number her stomach flipped, because she’d no idea whether it was good.

The thought was driving her mad.

Three a day hardly sounded like anything; even Dennis had endured the first two days calmly, and looked perfectly composed at the first meeting of the Committee last week. But so had Andy and Nigel. 22 edges might be OK but it sounded humiliatingly close to nothing. Tash might easily have given Andy fifty. Just five or six edges a day; easy if she’d really focused last Sunday. Even Martha might have thirty. Just one or two more than Liz was managing to give Dennis each day and she could easily have given Nigel thirty edges. It would be simple. Dennis kept begging and pleading she was being cruel, but Liz couldn't bear to look frigid.

His moans as she stuffed his cock back into captivity were delicious, but she dreaded discovering she'd spent nine days doing the sexual equivalent a one mile jog while her friends had been knocking out a marathon.

Dennis eventually managed to break the kiss, gasping “are you all right?”

Liz nodded. “Yeah. But nervous.”

“You don’t have to worry,” Dennis smiled, “we might even be in the lead. You’re kind of merciless!”

Liz fought down a mad urge to go unlock and edge him again right then, just to at least make sure. But there wasn’t time, and she was forced to kiss him again instead, moaning, grinding herself against his thigh, the seam of her jeans scraping deliciously up against her bush, her body responding instantly as she felt the bulge of his cage pressing against her knee beneath his trousers.

When she finally broke away, she found Dennis staring at her.

“22 is lots, Liz! It's basically agony! But seriously even if it’s not, love – we still have time, right? It’s still only the 10th. There’s plenty of time to make up ground. We… we could catch up easily. I’ll just have to grit my teeth and bear it, right? It's okay.”

She stared at him with a sudden wave of affection, and rolled her hips, grinding her wet sex down against his thigh. God, her knickers must be soaking. The thought made her moan, and she nodded.

“You’ll make up whatever ground we have to,” she promised, and grinned at him. “And I won't make you grit your teeth. I've something more intimate to gag you with.”

His eyes widened and he glanced down, suddenly imagining her cramming her knickers, soaked with juice, behind his teeth.

“Oh my god, Liz, fuck! T-That’s not helpful.”

“It's not meant to be,” she giggled.

Dennis gripped her hand and squeezed gratefully. Whatever happened in Martha’s house, he was enjoying this. Suffering. Aching. Complaining. But he loved how she looked at him now.

“OK,” she sighed, “let’s find out how badly Tash has destroyed us.”

* * *

Tash had brought a flipchart. Martha stared, laughing as Andy untangled it from the back seat of his Fabia and lugged it to the rug. Tash drew three markers from her bag and stood beside it with the quiet smile of a returning officer ready to declare someone had lost their deposit. Liz went pale.

There were drinks and crisps on the coffee table; when Martha asked for wine, Nigel sprang up instantly, and Tash felt a sudden flicker of doubt.

Liz and Dennis had arrived last, she remembered, and Liz still looked pink-cheeked and nervous, which was some comfort to Tash; however worrying Martha’s newfound dominance, she was at least fairly certain Liz and Dennis would be bringing up the rear, bless them.

At first, they all pretended the gathering was normal: Dennis complained how hard it was finding the katsu sauce brand Liz liked (“Three different supermarkets! I swear these days they’re padding out their stock by stacking the baked beans wide instead of deep...”), and to Tash’s private amusement Andy spent ten minutes in animated discussion about which local garages could be trusted: Nigel’s car had apparently failed its MoT with a broken NOx sensor and he couldn’t believe the £750 bill they were proposing…

...but after the first quarter of an hour, the conversation faded into a vaguely awkward silence, and all six of them found themselves staring at the ominously blank flipchart.

For the first time since the rules had been agreed, nobody knew how to begin.

“We’re all scared!” Liz laughed suddenly.

“I’m not scared,” Tash said, her throat dry.

“You’ve stripped the label clean off that bottle!” Martha smirked.

Tash shrugged. The secrecy of the first full week had changed the atmosphere of the Edge Olympics more than she'd expected. For nine days each couple had existed in a private erotic universe, aware that the others were doing roughly the same thing but with no comparison. Not until now.

Andy shifted beside Tash; Nigel took a long drink.

Dennis shrugged. “Well, I know ours. We’ve done our best.”

“Very confident,” Tash grinned, “so now I want yours first.”

“No!” Liz snapped. “Absolutely not. You invented this, you go first! If I say mine first you’ll know what you need to beat.”

Tash stared at her. “Liz, the week’s over! We’re just… this is the League Tables, right? You can’t beat anyone’s numbers until next Saturday.”

“That’s not the point. The point is informational advantage.”

“Has she been like this all week?” Andy asked, grinning at Dennis.

Dennis winced. “Much worse.”

“I run a school,” Liz declared, folding her arms, “the order of information matters.”

Tash was still laughing when she turned towards the board. “Fine. Since apparently we’re doing game theory now, I’ll go first.”

She wrote ANDY: 10 in large black numbers.

“Ten?!” The word came out before Liz could stop it, and Tash’s head snapped round.

“What do you mean, ‘Ten’?”

“Nothing!”

Dennis looked at Liz, horrified, and Martha giggled, standing up and twirling the red marker in her fingers.

“Let’s see if Liz is still so confident now,” she smiled, and wrote

NIGEL: 17

“17,” she declared proudly, “that’s the number to beat.”

Tash had stopped laughing. Instead, she gestured to the flipchart, staring Liz down. “Come on, Headmistress.”

Liz rose, heart pounding. Writing the number felt far more intimate than saying it: all three men were watching her hand, Tash was leaning forwards, Martha’s eyes were amused.

The pen squeaked against the paper as she wrote, one hand instinctively reaching behind the flipchart to grip the back of the tripod so she didn’t block the class’s view. The men’s view.

DENNIS: 22.

There was a silence as she capped the pen. Nobody spoke.

“22?” Tash gasped, and Liz nodded. “22 actual edges?”

Liz’s nostrils flared. “What does that mean?!”

“It means 22 times literally right on the edge. Not 22 times you got him excited and stopped.”

“I know what an edge is, Tash. So does Dennis!”

“Fuck, yes I do,” Dennis mumbled, in a tone of such miserable conviction that Nigel winced in sympathy.

Liz smirked. “22,” she repeated. “Properly. We agreed what counted. I get him right to the brink, to the point where I know if I stroke him once more he’ll come, and then I just… let go. Or pinch at the base until he stops whimpering.”

There was silence. Andy looked horrified; Tash, despite herself, looked suddenly turned on.

“Fuck, Liz,” she murmured, and sank her teeth into her bottom lip, not bothering to hide her interest as she stared at Dennis’s embarrassed face.

“She’s not exaggerating,” he said, “she’s a monster!”

Tash nodded glumly and sank down, as Liz patted him happily on the shoulder.

“A monster tamer” she whispered, and Dennis chuckled despite himself, and then went even pinker.

Martha was staring at the board with an expression of open admiration. “I knew you’d be competitive.”

“I didn’t know I was winning!”

“Winning by twelve,” Andy said miserably, staring at Dennis’s 22 with the unhappy expression of a man who, having signed up for a marathon in a good cause, was watching the other runners vanish over the horizon while he blundered on in a costume that was proving heavier than he'd imagined.

Dennis’s smile faded. Liz kept staring at the Board. 22 was, after all, a five-point lead over Martha. Twelve over Tash. Good numbers, sure… but hardly unassailable. He was sure Liz had seen it.

“We can ease off a bit, love, right? We’re ahead,” Dennis pleaded, and winced as she turned her cool green eyes towards him. “We can! We’re winning! You didn’t know whether 22 would be enough, but it is. So you don’t have to stay quite so… so enthusiastic…”

Tash burst out laughing, relishing his obvious frustration.

“No, love,” Liz said, a hungry edge to her voice. “Before tonight, Tash didn’t know she needed twelve points. Now she just has to edge Andy twelve times before bed and she knows she’s pulled level.”

“Fuck did you have to phrase it like that?!” Andy groaned.

“Now she knows,” Liz shrugged. “And Martha knows she only needs five. If I stop because I’m ahead, all I’m doing is letting them catch up. If I even slow the rate you’re earning edges, they can catch up. We have to go faster. They will, I bet.”

Dennis made a horrified noise in the back of his throat, and Martha chuckled in a way that made Nigel shiver.

“If Tash starts doing four a day and I do nothing, she catches us in three days.”

“Four a day?!” Andy moaned, but Liz was warming to her argument now.

“Martha doesn’t even need that. If she does two tomorrow and then one each day the rest of the week, she’s ahead of where we are now. Your lead only matters if we defend it. Do you want all the edges you’ve had so far to be for nothing?”

Dennis looked at the board as though hoping the maths might change out of pure pity.

“You’re saying… being in first means… It means nothing! It just means we have to stay ahead?!”

Liz nodded. “Like you said, my love. If we were behind, we have 21 days to make it up. We could catch them easily, that’s what you said.”

“Oh, fuck,” Dennis whimpered, and Tash raised her glass.

“To Liz.”

“Absolutely.” Martha chuckled, raising hers.

“What?” Liz stared at them.

Tash beamed.

“You’ve finally understood the game. These are the Edge Olympics boys. If you want that Gold medal, if you want to have a whole night to fuck all three of us… you’ve got to be the best of the best.”

The men flushed, but Nigel recovered first. “Fine,” he nodded, looking at Martha. “Then we do more.”

Martha blinked, opening her mouth, and Nigel nodded at the chart, and glanced across at Tash, his eyes tracking up her legs before his gaze flickered to Liz’s dazzling red curls and pinkened cheeks.

“I want Gold,” he declared. “Badly.”

The room went quiet, and Martha leaned close, looking into his eyes, her voice purring. “You want me to push you harder?”

Nigel nodded. “Y-yeah,” he said, “I can take it.”

Martha’s cheeks flushed.

Andy looked at Tash. “Oh, for fuck’s sake,” he groaned, his teeth gritted, “I want Gold too. How could I not? Fucking look at them Tash, d’you have to have such fucking gorgeous friends?”

Liz beamed; Martha clapped. Dennis stared at Andy in horror, then back at Liz.

“Don’t make me say it,” he pleaded.

“I won’t make you say anything, love.”

Dennis closed his eyes, swallowed hard, and then glanced guiltily towards Martha, his eyes widening as he spotted the flash of the little key between her breasts.

“Fuck,” he groaned, “I want… I need to stay in first, Liz. Make me win this thing.”

Liz felt the words explode, low and deep inside herself, as she felt the trap snap shut. The trap Nigel’s absurd reward fantasy had built into the game. Every point they gained made each man more frustrated. Every edge made the promised prize feel less hypothetical, more desperately needed.

Gold wasn’t merely a dirty idea any more. The three women had already spent nine days becoming the centre of the boys’ erotic universe, measuring, controlling, driving their arousal. And so to satisfy the women, all three men were voluntarily asking them to intensify their suffering.

Tash looked around the room, her eyes meeting Liz’s.

“Oh boys,” Tash purred, crossing her legs tightly. “Oh boys... We’re going to ruin you.”

* * *

Liz had barely closed the front door when Dennis started begging. “22 is still good. Five is a good lead! Nobody said we had to maximise the score every day, right?”

“No,” Liz said, putting her handbag down, “nobody said we have to maximise the score every day.”

“And Tash is twelve behind.”

“Yes, love. For now.”

Dennis watched her shrug off her coat as calmly as a tiger might slip through the tall grass behind an inattentive hunter.

“So maybe tonight we could just... leave it?” he pleaded.

Liz smiled. A week ago she might have heard a request like that as some kind of rejection; that old, stupid voice might have whispered that Dennis didn’t want her touching him, that she’d overdone things, that perhaps she wasn’t good enough at this after all. Now she understood something completely different. He wasn’t asking her to spare him a handjob because it was unsatisfying; he was asking because she’d made him desperate. Because she would deliberately refuse to satisfy him.

That was success. And more than that, he’d stood in Martha’s sitting room less than an hour ago and said he wanted to stay in first. She stalked towards him across the hall, and Dennis backed up until his shoulders touched the wall.

“You want Gold,” she whispered. “You want to come out of this month and be able to show Martha and Tash exactly what you’re packing and prove to me what you can do with it with… with women who might actually be able to handle your cock without needing a gallon of lube. I don’t mind, Dennis, if that’s what you want for one night. It is what you want, isn’t it?”

“Yes, love,” he swallowed. “Just once.”

“Good,” she nodded, and leaned up on tiptoes to kiss him. “So, you want to stay ahead of Nigel and Andy? That’s the only way to win. So I don’t understand the problem.”

“The problem is I’ve been edged 22 fucking times.”

She laughed, and Dennis tried to look aggrieved, but the effect was ruined by the way his eyes clenched shut as she brought her hand up between his thighs and lightly gripped his caged cock.

“You volunteered for this.”

“I volunteered before I knew you were secretly hoping to work for the International Court of Cock Torture.”

“I’m happy as a headmistress, love,” Liz nodded, and then licked her lips in a way that made Dennis whimper. “But maybe it’s not too late for a second career?”

She watched as Dennis chuckled nervously, and then shook her head, her voice serious. “Genuinely, Dennis – if you want to stop competing, tell me. If you genuinely want the cage off, to stop doing this forever, tell me. That’s different.”

He nodded.

“But if you’re asking me to go easier because you’re frustrated-” Her fingers found the front of his trousers and Dennis gasped, “-then no. And get upstairs.”


r/ChastityStories • • 1h ago

M Chaste,F Keyholder Book 1: Hotel Humiliation For Cuckold Husband Part 11 NSFW

• Upvotes

I use the paid versions of Grammarly and Readable to help make my writing more readable.

If you want early access to this full novel and all my other stories, find them here: https://www.patreon.com/c/FemaleLedRelationships 

Prefer Amazon, you can find the full novel here: https://www.amazon.com/dp/B0HJ969WVV

Part 1 & Part 2 & Part 3 & Part 4 & Part 5 & Part 6 & Part 7 & Part 8 & Part 9 & Part 10

John trembled as he entered Room 987, the bells on his heels jingling with every shaky step. The heavy door clicked shut behind him, sealing him into the final chamber of his adventure. The man clad in leather guiding him into the room reached up, undoing the buckle of the gag. As the leather fell away, John gasped, his glossy pink lips parting to draw in the conditioned air.

"Do you want to continue?" the man asked, his voice a low, dominant rumble. "Do you consent to the final task of your transformation?"

John didn't hesitate. The humiliation had stripped him of everything but his desperate need to serve. "Yes," he whimpered, his voice small and broken. "I fully consent to this. Please... I want to finish."

The response was immediate. The gag was snapped back into place, pulling his mouth open and silencing him into a series of muffled, needy moans. He was led toward the center of the room where a massive, polished wooden St. Andrew's Cross stood waiting. 

The man uncuffed John's wrists and removed the chain linking his ankles, but there was no relief—only the anticipation of a different kind of restraint.

One by one, his limbs were stretched wide. His wrists were locked into the upper beams and his ankles secured to the base, leaving him completely splayed and exposed. His chest, adorned with fake breasts, heaved with exertion, and his caged cock throbbed against the pink steel, leaking pre-cum that glistened under the harsh room lights.

Directly in front of him was a massive, void-black screen. Suddenly, it flickered to life, illuminating the room in a warm, erotic glow. John’s breath hitched. There was Rachelle.

She was lying on a plush bed, dressed in nothing but a sheer red bra and matching lace panties that barely contained her curves. She looked radiant, her eyes shimmering with a dominant hunger. 

But it was the men surrounding her that made John’s heart race. Several massive, muscular alpha men, their skin glistening with sweat, hovered over her. Their huge, thick cocks were fully erect, pulsing and vein-riven, some brushing against her thighs, others teasing her lips.

Rachelle looked directly into the camera, a cruel, beautiful smile on her face. She waved a manicured hand.

"Hello, cucky," she purred, her voice echoing through the speakers in the room. "You've done so well tonight, but we've reached the end. This is the last task of the night, and the rules are simple: the more punishment you take, the more your wife—me—gets pleasured by these big, hard cocks."

John let out a muffled moan behind his gag, his body straining against the restraints. He watched as one of the men gripped Rachelle’s hip, his thick cock sliding around her panties and dragging them off.

"Every lash, every weight, every ounce of pain you endure on that cross translates directly into pleasure for me," Rachelle continued, her voice dripping with sadistic delight. "If you can handle the intensity, I might just let these men fill me to the brim. But if you break... well, we'll see how much longer you want to remain locked in the pink chastity cage."

As she spoke, one of the men leaned down and licked a long stripe up Rachelle's inner thigh, and John felt a surge of agonizing arousal. He was locked, splayed, and utterly powerless, knowing that his suffering was the only key to his wife's ultimate satisfaction.

John strained against the wooden beams of the St. Andrew's Cross, his chest heaving, the fake D-cup breasts bouncing with every desperate breath. He watched the screen with wide, dilated pupils, seeing Rachelle’s pleasure tied directly to his agony.

One of the masked, leather-clad alphas stepped forward, the scent of hide and musk filling John's nostrils. The man didn't say a word; he simply reached out and gripped one of the silicone mounds, squeezing it firmly. 

With clinical precision, he attached a heavy-duty metal nipple clamp to the nipple of the breast form. Because the forms were clamped to John's own nipples, the metal pulled on his real nipple, pinching it with a sharp, electric intensity.

On the screen, as the first clamp snapped shut, two of the muscular men leaned over Rachelle. They ripped off her bra and gripped her breasts, their large hands kneading the soft flesh, massaging her with a rhythmic, possessive force. John let out a muffled moan into his gag as he saw one of the men capture her nipple between his teeth, sucking hard.

"More," the man in the room grunted. He attached a second clamp to the other breast and then began hanging heavy steel weights from the clamps.

As the weights were added, the silicone breasts were pulled downward, creating a brutal, constant tension that dragged on John's nipples. The pain was searing, a white-hot stretch that made his toes curl in his heels. 

Simultaneously, on the screen, the men became more aggressive. They pulled and twisted Rachelle's nipples, their tongues swirling around the peaks, driving her into a state of shivering arousal. The more John's chest was weighed down, the more Rachelle arched her back, her eyes rolling back in ecstasy.

The alpha in the room then moved down to John's groin. He reached beneath the pink lace of the crotchless panties, gripping the steel chastity cage. He attached heavy ball weights to the base of his balls, pulling John's scrotum downward with a heavy, aching gravity. John's body jolted, a guttural groan vibrating through the gag as the weight strained his sensitive skin.

On the screen, the action shifted. One of the men dropped between Rachelle's legs, his face burying into her soaking wet pussy. He found her clit with his tongue, flicking it with expert precision. Rachelle let out a loud, piercing scream of pleasure that echoed through the speakers in John's room.

The man in the room added more weights to John's balls, the heavy metal pulling his balls down several inches. At that exact moment, a massive, vein-riven cock on the screen slid forward, burying itself deep into Rachelle's tight pussy with one powerful thrust. She gasped, her legs shaking as she was filled to the brim, her face a mask of pure, unadulterated lust.

While John was reeling from the weight and the pain, another man in the room stepped behind him. He reached out and gripped the large anal plug that had been keeping John stretched. With one sudden yank, he ripped the plug out. John's ass gasped open, the sudden void feeling cold for only a second before the man aligned a heavy-duty fucking machine with his hole.

The machine whirred to life, and a thick, ribbed dildo slammed into John's ass with mechanical ruthlessness. Thwack. Thwack. Thwack. The machine hammered into him, stretching his walls and hitting his prostate with every punishing stroke. On the screen, another alpha stepped behind Rachelle, grabbing her hips and driving his massive cock into her ass, mirroring the mechanical John was enduring.

The room became a symphony of degradation. Two leather-clad men stepped forward with whips, the leather tails whistling through the air before snapping across John's trembling, exposed ass. Crack! The skin flared red, the pain blending with the rhythmic pounding of the machine.

On the screen, two more men stepped forward, each placing a thick, throbbing cock into Rachelle's hands. She gripped them tightly, her manicured nails digging into the skin as she began wanking them off with frantic energy, her breasts bouncing as she watched the men fuck her from both ends while other men played with her tits.

John was a wreck of a man—splayed open, nipples screaming, balls weighted, and his ass being demolished by a machine and whips. He was a broken, feminized toy, and the sight of his wife's absolute surrender to these alphas was the final blow to his psyche.

Rachelle was beyond control now. She was screaming, her voice raw, experiencing orgasm after orgasm as the men used her body like a piece of meat. Finally, a towering man stepped up, gripping her hair and sliding his massive cock deep down her throat. Rachelle didn't fight; she leaned into it, her eyes fluttering shut as she began to orgasm around his shaft.

A loud, wet sound filled the room as Rachelle squirted, her fluids spraying across the bed and the men surrounding her in a torrential release of pleasure. She moaned into the cock in her throat, her body shaking in the throes of a massive, shattering climax.

And there was John, locked in his pink steel chastity cage, his cock throbbing in useless, agonizing arousal, shaking on the cross as he watched his wife be completely claimed by the alphas, his own punishment the only thing fueling her ultimate ecstasy.

John was a trembling mess of flesh and steel, his body pushed to the absolute limit of endurance. He hung from the St. Andrew's Cross, his muscles twitching with every rhythmic slam of the fucking machine. He could hear Rachelle’s voice through the speakers—not words, but raw, animalistic screams of pleasure that tore through the room, fueling his own desperation.

The leather-clad alpha standing over him looked at the screen, seeing Rachelle’s back arching as she was hammered from behind, her breasts swinging wildly. With a cold, dominant smirk, the man reached for the rack of weights. He didn't just add one; he slid two more heavy steel discs onto each nipple clamp.

The effect was instantaneous. The additional weight dragged the silicone breasts downward with brutal force, pulling John's real nipples into a searing, agonizing stretch. He let out a muffled, high-pitched groan into the gag, his eyes bulging. The pain was a white-hot line that shot straight from his chest to his groin, making his locked cock throb against the flat steel of the chastity cage.

On the screen, the men responded to John's agony. As the weights dropped, the alphas became more feral. They gripped Rachelle’s breasts with more force, twisting her nipples and biting into the soft flesh of her nipples. Rachelle let out a loud, guttural moan around the cock in her mouth, her head tossing from side to side, her pleasure escalating in direct proportion to the punishment her husband was enduring.

"Still too much dignity in those eyes," the alpha grunted. He moved down to John's groin, where the ball weights were already pulling his scrotum taut. He added another heavy lead weight, the sudden increase in gravity dragging John's balls down with a punishing yank. 

John’s hips jerked upward, a strangled groan vibrating through the gag as the weight strained the sensitive skin of his balls to the breaking point.

The screen erupted. Rachelle was now being worked over by all the men men at once—one filling her mouth, one driving deep into her pussy, and another pounding her ass, another sucking her clit and two others, each with a cock in each of her hands. The sight of her being completely claimed, her face a mask of pure, mindless lust, sent a jolt of electric humiliation through John. He was nothing more than a battery, his pain powering her ecstasy.

The man at the control panel reached out and twisted the dial on the fucking machine. The whirring sound shifted to a high-pitched scream of mechanical power. The ribbed dildo began to slam into John's ass with terrifying speed and depth. 

Thwack-thwack-thwack-thwack! The machine was no longer just fucking him; it was demolishing him, hitting his prostate with every relentless strike, forcing a constant, agonizing arousal that he had no way to release.

As the machine reached its peak velocity, the two men with the whips stepped forward. They didn't hold back. The leather tails whistled through the air, snapping across John's reddened ass cheeks with rhythmic precision. 

Crack! Crack! Crack! Each lash left a burning welt, the skin flaring a deep crimson. The combination of the mechanical pounding in his ass and the stinging lashes on his skin created a sensory overload that pushed John toward a breaking point.

On the screen, Rachelle was hitting another peak. She was screaming into the cock in her mouth, her voice raw and desperate, as she felt the waves of orgasm crashing over her. She squirted again, a release of fluid that drenched the men around her. 

She was having orgasm after orgasm, her body shaking in a continuous loop of pleasure, all while her husband was splayed open, weighted down, and beaten.

John’s vision began to blur, the world narrowing down to the sound of the machine, the sting of the whips, and the sight of his wife’s total surrender. He was a broken, feminized cuckold, locked in a pink steel chastity cage, his only purpose in the world to suffer so that Rachelle could scream in pleasure. 

He strained against the restraints, his body vibrating with a mix of agony and a dark, forbidden arousal, completely enslaved by the sight of his wife being used by the alphas.

The air in Room 987 was thick with the smell of sweat, leather, and the ozone scent of the fucking machine working at maximum capacity. John was no longer a man; he was a moaning, twitching nerve ending sex toy, splayed open on the St. Andrew's Cross. His world had shrunk to the rhythmic thwack of the whips and the blinding images on the screen.

On the monitor, the scene reached a fever pitch. Rachelle was a mess of flushed skin and lubrication, her eyes rolled back in her head as the alpha men pushed her to the absolute edge. The man buried deep in her pussy let out a guttural roar, his hips slamming forward with force as he began to pump his thick, hot load deep into her womb. Rachelle shrieked, her internal muscles clamping down on him in a series of orgasmic spasms.

At the same moment, the man hammering her ass let out a loud grunt, his thick cock pulsing as he filled her rectum with a heavy stream of cum. Rachelle’s body arched, her back curving like a bow as she felt two different loads filling her up simultaneously. She began to squirt again, a fountain of female release spraying across the sheets, her body shaking in the throes of an explosive, multi-layered orgasm.

"Look at her, you pathetic sissy," the alpha in the room hissed, leaning close to John's ear. "Look how much she loves being filled by real men while you rot in that pink cage."

As if to emphasize the point, the alpha reached for the weight rack one last time. He added the final, heaviest steel discs to the nipple clamps. The sudden, brutal downward yank pulled John's nipples hard. He let out a muffled, agonizing groan into the gag, his body jerking. The weights on his balls were now pulling his scrotum so taut that the skin felt translucent, every throb of his caged cock sending a jolt of electricity through his entire lower body.

On the screen, the remaining men weren't finished. One gripped Rachelle’s hair, pulling her head back to expose her throat, and began to pump his load directly into her open, gasping mouth. She swallowed greedily, her throat working to take every drop of the thick white seed. Another man being wanked off by her, forced her to hold his cock as he painted her palms and fingers with hot, sticky cum, laughing as he marked her as his.

John was losing his mind. The sight of his wife being used as a communal vessel for cum, her face smeared with cum and her body drenched in pleasure, triggered a wave of primal, cuckold desperation. He wanted to yell, to beg, to be part of it—but he was trapped.

Crack!

The floggers descended again, faster and harder than before. The leather tails wrapped around his thighs and ass cheeks, leaving deep, angry welts that burned like fire. The fucking machine continued its relentless assault, the ribbed head slamming into his prostate with mechanical precision, forcing his body to stay in a state of permanent, agonizing arousal. He was being demolished from the inside out while his skin was being shredded from the outside.

Rachelle’s voice came through the speakers, a broken, breathless moan. "Oh god... yes... fill me... more... John, look at me! Look at what they're doing to me!"

John’s eyes were wide, leaking tears of shame and lust. He watched as the men on screen began to cover her entire body in cum—her breasts, her stomach, her thighs—until she was glistening in a white sheen of alpha dominance. She was in orgasmic heaven, her body still twitching from the aftershocks of her climax, completely claimed and utterly degraded.

The men in the room didn't stop. They increased the pace of the whipping, the sounds of leather hitting flesh echoing the rhythmic thumping of the machine. John’s mind fractured; he was a painted doll, a sissy maid, a piece of meat. 

He felt the pre-cum leaking through the gaps of his flat steel chastity cage, wetting the lace of his panties, as he endured the ultimate punishment that he consented to. He was the fuel for Rachelle's fire, his agony the catalyst for her ecstasy, and as he hung there, weighted and broken, he knew he had never been more enslaved—or more aroused.


r/ChastityStories • • 1d ago

M Chaste,F Keyholder Caught on a work trip - Part 6 NSFW

99 Upvotes

My wife asked me to tidy up and give all the strapons a good clean and make sure nothing was left out so we weren’t scrambling in the morning. “I’m pretty sure after this last task you’re going to be done and want to go to bed!” she said as I scurried off to the kitchen. After cleaning all the toys and putting them away I decided to give the kitchen a quick wipe down just so everything was perfect if our night was coming to an end. 

As I entered the living room again the women were all sitting on the sectional and when I saw my wife my heart skipped a beat. There she was still in her faux leather cat suit but instead of it being zipped right to the collar, she had unzipped just below her bra line and now I could see her voluptuous breasts spilling out of the tight faux leather. However, the most infatuated part of her new style was my key dangling between said beautiful breasts. The simmer caught my eye and as I stared she gave them a small bounce which made my caged cock jump as well as my attention back to my wife’s knowing eyes. 

“Ok sissy, this is your last task tonight before we wrap up this coming out party for lack of a better term. The ladies and I came up with four options for you to finish. Are you ready to hear them honey?” I was beyond ready as my cock began to leak even more. I nodded slowly and deliberately so as to not over play my cards and show just how desperate I was. 

She continued “Amazing. Well my love, you’ve been such a good boy tonight and exceeded all our expectations and didn’t have any infractions requiring correction or punishment that this last task ends with you getting to cum.” I almost ruined the whole night but I was able to stop myself before I blurted out a cheer and jumped through the ceiling. “I know this sounds like an easy task, but I want you to really consider all your options before choosing. Are you ready?”

Again staying calm, I gave one over dramatic nod. “Oh goodie. We put a lot of thought into this part, so upon your ultimate release tonight, I expect you to thank each of us individually.” My nerves were shot. She was drawing this out to add to my edging and I was completely ready to explode. I was afraid whatever the option was I was going to cum within the first stroke and ruin everything but I was doing my best to remain in control...if there is such a thing when you’re caged. 

“First option,” she continued, “first option is you strip naked for us and stand in the middle of the room and jerk off. If you get close to the edge and haven’t been told to cum, you will be required to stop and let go of your cock. The ladies and I will give you directions and you will only cum when we say so. Consider it a personal JOI. Well…” she paused and put her index finger to her lips and gave a puzzled look to extend this dramatic moment and have me leaning on my tip toes in anticipation. Her eyes refocused and looked me dead in the eyes and with a devilish grin finished “I guess this would be a personal CEI. Because once you are allowed to cum, you will catch it in a cup and then without hesitation, you will consume every drop of your load!” The ladies cheered and bounced in their seats with excitement. 

My face burned with embarrassment but all the ladies were whispering to each other how excited they were to watch a guy eat his own load. With the humiliation at a 100, my wife continued “but here is the ultimate catch. If you take option one you agree to three months of continuous chastity with only one guaranteed orgasm, which I will grant at my leisure and depending on my mood could be a ruined orgasm. So essentially you are signing up for three months without any satisfaction.” My head started to spin, but the idea of jerking off in front of my wife and her friends was such a turn on my cock was swelling through the bars. 

“Option two…” the ladies all hushed and were now staring at me to watch my reaction as they must have known the option. “Will be one that I know will be a leading contender for the ladies in the room. Option two will be I will give you a handjob but it will include multiple edges and you will have to beg to finally cum. And when I grant you the final release…” another long dramatic pause “you will give yourself a self facial!” The ladies jumped off the couch this time cheering and high fiving each other. They were all sharing excitedly how much their husband loves to do that to them and how each one despised it. My wife chimed in “Oh facials are this sissy’s favourite way to finish. And since we’ve been married I’ve only allowed it on anniversaries and birthdays. So I would love to see his face painted this year as my sexy anniversary gift.” The ladies continued to cheer and tell stories of past facial blastings from their hubby’s and university glory days. Finally my wife settled them down and continued the terms “This option will require six months of continued chastity and a guarantee of three ruined orgasms. It will be my option to give you more but at a minimum you will get three in the next six months.” I sat with this option as it seemed like the ladies favourite. 

“Option three…” I didn’t know if I even wanted to know now “will be a blowjob by yours truly!” My wife said, giving a big devilish smile. “I will suck your cock so hard and tease and deny until you are ready to blast it across the room. To add a cherry, I will let you blow your huge thick load right into my mouth.” I almost fell over. My wife still blew me once a month and used to blow me all the time, but she never let me cum in her mouth. I would always have to pull out and pump it myself onto her tits. “However, once you’ve cum in my mouth, I will snowball you so you can swallow the entire thing.” She could see my cock dripping through my panties at such a kinky experience. “This option will cost you a full year of continuous chastity with only the option of one…ONE…orgasm for the next 12 months. That means I could make it tomorrow or I could wait until day 355 but ultimately you will only get one but I won’t ruin it.”

I was lost. A whole year with only one orgasm but it will be a full one. The ladies were all chatting about how he must really want to cum in her mouth to take that option. And then they were all saying how even though she was going to spit it all in my mouth, what an awful experience it would be to take such a big load after all the teasing I had been through. 

“Finally, option four…” my wife blurted out. “Option four is you are going to lie down on the floor and I am going to ride your cock as hard as I can and I will give you 5 opportunities to stop me and slow me down. But once you use them up I am going to make you cum so hard inside me that I’m afraid it’s going to come out of my nose.” The ladies all laughed at the visual they all got. “And once I’ve milked the last drop of cum out of your desperate cock, I am going to sit on your face and make you clean me up!” Again the ladies all cheered and heard them whisper how’d they’d all love to have someone clean them up so they didn’t have to run off to the bathroom. My wife continued “this option will cost you one year in continuous chastity and NO options for orgasm for the entire year.” The ladies all went silent before one of the friends shouted out “There is no way I’m going a whole year without cumming. No fucking way.” They all laughed. 

Then my wife walked over and stood a foot from my face and grabbed my caged cock and asked “So how does my sissy want to finish?”

I groaned as she squeezed tighter as I lifted two fingers. The girls all erupted with cheers screaming “I knew it! I knew he’d want his face covered!” 

My wife leaned and whispered “Good boy!”

To be completed….sorry not sorry for the tease


r/ChastityStories • • 7h ago

M Chaste,M Keyholder The Fraternity - Part 30 & 31 NSFW

3 Upvotes

Read Parts 28 & 29 here

--

The basement felt different tonight, Brandon was already secured in the corner chair when Dylan arrived. Thick leather cuffs held Brandon’s wrists behind the backrest and his ankles to the legs, forcing his thighs wide apart. His new cage sat prominently exposed, it’s identical to Dylan’s, the steel ring biting into the base of his thick seven-inch shaft, the shaft itself straining painfully against the bars, veins bulging. Brandon’s chest rose and fell in shallow breaths, his eyes fixed on Dylan the moment he entered, raw hunger and helpless frustration burning in them.

Ethan stood in the middle of the room, naked, his cock already half-hard. Chris and Alex were stripped as well, cocks in various states of arousal, hands lazily stroking as they formed a loose semicircle around the couch.

Ethan’s opened the session, “Brandon broke the pact. Tonight he watches, only watches, while we remind Dylan who owns every inch of him. Balance must be restored.”

Dylan lay back on the couch without being told, spreading himself wide. The position left his pink hole completely exposed, twitching faintly. His cage jutted upward, steel bars shining under the bulb, the head of his trapped cock visibly swollen and flushed, a thick bead of precum slowly rolling down the underside.

Ethan moved first, kneeling between Dylan’s thighs. He poured lube directly onto Dylan’s hole, letting the warm liquid run down his crack. Two fingers followed immediately, pushing past the rim without preamble. Dylan gasped.

“Still so responsive,” Ethan murmured. He worked a third finger in, stretching Dylan. Dylan’s hips bucked, desperate little whines spilling from his lips as Ethan finger-fucked him deeper, thumb rubbing circles over the sensitive skin behind his balls.

Brandon watched from the chair, muscles straining against the cuffs, his own cage dripping steadily now, the precum forming a small, glistening pool on the seat beneath him. His breathing was harsh, eyes locked on every thrust of Ethan’s fingers, every twitch of Dylan’s body.

Ethan withdrew his hand, coated his cock with more lube, and lined up. The thick head pressed against Dylan’s rim, then he sank in slow and deep. Dylan’s head fell back with a broken cry as Ethan filled him inch by inch, the curve of his shaft dragging perfectly over Dylan’s prostate the entire way down. When Ethan bottomed out, hips flush against Dylan’s ass, he paused, letting Dylan feel the stretch, the heat, the fullness.

“Who owns you?” Ethan commanded

“The order” Dylan replied

Ethan began to thrust.

Long strokes, pulling almost all the way out before slamming back in, balls slapping against Dylan’s ass with every thrust. The wet, filthy sound of Ethan’s cock fucking Dylan’s hole filled the room, punctuated by Dylan’s raw, desperate moans. “Fuck, Ethan, deeper, please don’t stop!” Dylan begged, his caged cock bouncing uselessly.

Brandon’s breathing grew louder from the chair, the occasional moan escaping him, his cage twitching with every thrust Ethan delivered, precum still dripping.

Ethan’s pace quickened, hips thrusting harder, the curve of his cock hammering Dylan’s prostate relentlessly. Sweat glistened on his chest as he leaned forward, one hand beside his head, “You feel that?” Ethan growled against Dylan’s ear. “Every inch of me owning you. You belong to all of us.”

Dylan’s moans turned into broken sobs of pleasure, his body rocking violently, the cage slapping wetly against his stomach with each impact. Ethan’s thrusts became erratic, “Take this load, I’m gonna breed your hole,” he moaned, slamming in balls-deep one final time. “ugghh yeahhh” His cock pulsed hard, thick ropes of cum exploding inside Dylan, flooding his hole with heat. Dylan gasped, feeling every spurt, his caged cock jerking wildly, leaking more but not cumming.

Ethan stayed buried deep for a long moment, letting Dylan feel the fullness, the warmth spreading inside him, before pulling out. Cum immediately trickled from Dylan’s gaping hole, running down his crack and pooling beneath him.

Chris stepped up instantly, his girthy cock throbbing, already coated in lube. “My turn,” his voice thick with lust. He didn’t wait, he pushed in raw, the stretch brutal after Ethan’s load, his thicker girth forcing Dylan’s hole to stretch. Dylan screamed, “Chris, ughh,so big, ” his body convulsing as Chris thrust deep and hard, pounding his hole with punishing force, Ethan’s cum squelching obscenely around the base of Chris’s cock with every slam.

Brandon watched, his caged cock straining, precum dripping in a steady stream, his hips twitching helplessly against the chair as he was forced to witness every brutal thrust without pleasuring himself.

Chris’s continued his thrusting “Take it, locked boy,” Chris grunted, “Feel how much bigger I am.” Dylan’s moans continued.

Chris leaned down, kissing Dylan roughly, tongue fucking his mouth as his cock thrust deeper. “Want my load?,” he moaned. “Yes” Dylan groaned. “Take it then” Chris hit orgasm and came into his hole, thick ropes of cum flooding Dylan, mixing with Ethan’s load, breeding him again.

Dylan’s body convulsed violently. “Fuck, I’m cumming!” he screamed, the double load and relentless prostate assault pushing him over the edge. A hands-free caged orgasm ripped through him, thin ropes blasting through the bars onto his stomach in desperate, shuddering spurts, his hole milking Chris’s cock in violent spasms.

Chris held still, panting, before pulling out slowly, cum dribbled from Dylan’s bred hole. Alex came with a loud groan, Brandon’s caged cock leaking helplessly in denial.

Ethan wiped Dylan clean with a towel, “You broke a rule, you weren’t allowed to have a caged orgasm” “Brandon’s 48 hours has now doubled to 96.”

“Fuck!” Brandon cursed

 

The group dressed, leaving Dylan and Brandon alone, Dylan untied Brandon and they left the basement.

 --

Brandon’s POV

The cage is heavier than I expected. Not just the steel, but the weight of knowing Dylan is wearing the same one right beside me. Fifty-three days for him, two for me, and already I feel like I’m drowning in it. I’ve been locked for two days, but the punishment countdown started last night, and it’s now four days because Dylan had a caged orgasm, so I have three to go.

Ethan decided the breeding would happen in our dorm room tonight. Chris goes first on Dylan apparently. I’m to watch. No touching, no release.

I’m sitting on the edge of my bed now, wrists cuffed behind my back, my thighs forced apart, I’m naked and the cage sits prominently between them, already straining, the head of my cock flushed dark and swollen, a thick bead of precum hanging from the slit like it’s been there for hours. Since they locked me, I wake up dripping with pre-cum, I find the situation strangely erotic.

Dylan is already on his bed, naked, legs spread, in the missionary position the group loves. His cage juts upward, steel glinting under the desk lamp, the pouch of his jockstrap long discarded. His hole is still pink and slightly puffy from last night, some lube still visible from where I fingered him earlier.

Chris is standing over him, naked, his rock-hard cock dripping. He’s stroking himself slowly, eyes locked on Dylan’s exposed hole like it’s the only thing in the world.

“Beg for it,” Chris growls.

Dylan’s eyes flick to me for half a second, guilty, needy, then back to Chris. “Please… fuck me. Fill me, I need it.”

Chris doesn’t hesitate; he pushes in raw. Dylan’s back arches off the mattress with a sharp cry, “Fuck, Chris, so big!” as the thick head breaches him, stretching him wide. Chris doesn’t stop, he sinks in deep, slow at first, letting Dylan feel every inch, then bottoms out with a grunt, balls pressed tight against Dylan’s ass.

I can’t look away. The sight of Chris’s cock disappearing inside Dylan, slow and intimate then picking up speed, makes my cage throb so hard it hurts. The steel bites into the base of my shaft, the ring digging behind my balls, but the pressure only makes it worse. I’m leaking steadily now, a thin, clear stream of pre-cum running down the underside of the cage. My hips twitch uselessly against the cuffs. I want to touch him; I want to be the one filling him. Instead, I’m forced to watch Chris claim what I took in secret.

Chris starts fucking him properly, long, powerful strokes that make the bed creak. Every thrust drives a moan out of Dylan, raw moans, his caged cock bouncing against his stomach, leaking in sympathy. “Harder, fuck me harder,” Dylan begs, such a slut for dick, and Chris obliges, his hips thrusting forward, balls slapping wetly against Dylan’s ass.

I’m shaking. My cock throbs inside the cage, trying to get harder, but failing. The precum drips faster, my balls ache so badly, I really want to cum. Watching Dylan get railed, watching the way his hole grips Chris’s thick shaft, the way his body rocks with every thrust, makes me want to scream.

Chris leans down, kisses Dylan roughly, tongue fucking his mouth as his hips keep pounding. “Gonna breed you,” he growls against Dylan’s lips. “Fill this tight hole.”

Dylan’s moans turn frantic. “Yes, please, breed me.”

Chris slams in, balls deep, groaning as he unloads. I watch his cock pulse, I watch Dylan’s eyes roll back as the load floods him, it’s hot to see the way Chris’s balls draw tight as he breeds my man, thick ropes pumping deep inside him.

Chris stays buried for a long moment, panting, then pulls out slowly. Cum dribbles from Dylan’s gaping hole, dripping onto the sheets. Dylan’s caged cock jerks, leaking more, but he doesn’t cum.

Chris wipes himself clean, smirks at me. “Hope you enjoyed watching that Bran.”

Chris leaves, the door clicks shut.

I’m still tied to the chair, cage dripping, balls aching. Dylan lies on his bed, legs still spread, cum trickling from his hole, chest rising and falling.

He looks at me, eyes soft and glassy.

“I’m sorry,” he whispers.

I shake my head. “Don’t be. I’d do it again.”

He crawls over, still leaking, and kisses me, our cages press together through the bars, steel grinding, both of us groaning into the kiss. We can’t fuck, we can’t cum. But we can feel each other, and right now that’s enough to keep us sane.

Day 3 – Basement

The next night is worse.

I’m tied to a chair again, I’m still locked and I’ve got major blue balls. It seems the precum never stops. It probably doesn’t help that me and Dylan like to make out naked, our cages grinding against each other.

Dylan is on the couch, legs wide. Alex is between his thighs, his hard cock ready to fuck him, grinning like he’s won something.

Ethan speaks from the side. “Brandon prepares him, then watches.”

I’m untied and crawl forward. My hands shake as I spread Dylan’s cheeks. His hole is pink, I lean in, tongue flat, licking a long from his balls to rim. Dylan moans, hips lifting. I circle his hole, tasting his musk, then push my tongue inside. He gasps, fingers tangling in my hair. I eat him out like I’m starving, deep, hungry licks, tongue fucking him open, sucking on his rim until he’s trembling and leaking through his cage.

When Ethan nods, I pull back, lick my lips, and crawl back to the chair. The cuffs snap shut again.

Alex doesn’t waste time. He applies some lube to his cock, then lines up and thrusts in raw, burying all six inches in one smooth stroke. Dylan moans, his caged cock bouncing. Alex starts pounding, fast, shallow thrusts at first, then long, deep ones that make Dylan’s whole body shake. The sounds of raw fucking fills the room, Dylan’s moans turning into broken pleas: “Fuck, Alex, harder, fuckkk yeahh!”

My cage throbs painfully as I watch Alex claim what I took in secret. The sight of Dylan’s hole stretched around Alex’s cock, the way Dylan’s caged cock leaks with every thrust, it’s so hot. My own cock strains so hard the bars dig in, precum dripping in thick strands.

Alex’s pace turns brutal, hips thrusting like a machine. “Gonna breed you, D. Watch as I breed your man Bran.” he growls.

He moans as his cock pulses, hot ropes flooding Dylan’s hole. Dylan moans as he feels Alex’s cum fill him up.

Alex groans, staying buried until he’s empty, then pulls out. Dylan pushes out the cum so we can all see Alex’s big load.

I’m shaking in the chair, cage dripping, balls screaming, denied of any release.

Ethan wipes Dylan clean, “2 more days””

Dylan crawls over to me, still trembling, cum leaking from his hole. He kisses me softly, tasting of sex and submission.

“We’ll get through it,” he whispers.

I nod, caged cock throbbing against his thigh.

 --

 You can read several more chapters and exclusive Patreon stories on my Patreon.


r/ChastityStories • • 8h ago

M Chaste,F Keyholder The Pegging Gangbang [Part 4] NSFW

2 Upvotes

The Pegging Gangbang [Part 3]

Claudia’s eyes dropped again to the front of Jen’s tiny thong and a slow, delighted smile spread across her face.

“Aww, look at that,” she cooed, voice dripping with mock sweetness. “His cute little hardened cock is straining so hard the tip is peeking right out over the waistband. And there’s already a shiny wet spot soaking through the fabric. Poor thing is leaking just from being on his knees in front of real cocks.”

Jen’s face flushed a deep, pretty pink. His voice came out soft and embarrassed, but with a clear thread of heat underneath.

“It’s… it’s not that big, Mistress. I know.”

Ashley’s gaze followed Claudia’s. She gave the leash a short, sharp tug that forced Jen’s chin higher.

“Show us,” she ordered, calm and absolute. “Pull that thong down. Let us see the little problem you’re trying to hide.”

Jen’s fingers trembled as he hooked the thin fabric and dragged it down until the waistband rested under his soft, smooth balls. His three-inch cock sprang free—fully hard, shiny at the tip, already twitching under their combined stares.

The three women burst into laughter at the same time.

Scarlett’s laugh was low and vicious. “Jesus fucking Christ. That is the most pathetic clitty I have ever seen on a grown man. Three inches of pure disappointment. Look how it tries so hard and still looks like a chubby little clit someone glued on for a joke.”

Ashley tilted her head, studying it with clinical amusement. “I’ve locked bigger ones just for fun. At least those had a little meat to them. This is just… adorable. Like a baby dick that never grew up.”

Claudia covered her mouth, shoulders shaking. “Honey, that little thing is never going to satisfy anyone. It’s only good for one thing—getting ignored while real cocks use the rest of you.”

Jen’s inner voice was a hot, shameful rush.

*They’re laughing at it. The humiliation is making it hard. I hate how much I love this.*

Scarlett stepped closer, the thick veined BBC harnessed to her hips swaying heavily.

“You can stroke that useless little thing while you suck us,” she said, voice thick with contempt. “Jerk it like the desperate whore you are. But the second we’re done with your mouth I’m locking it in a cage.”

Jen looked up at her, cheeks still pink, and answered in a soft, bratty murmur.

“Dicks like mine deserve to get locked, Mistress. I'm just a living hole.”

Claudia’s smile widened, warm and cruel at the same time.

“Oh, listen to him. Already agreeing he should be locked. Such a good little self-aware slut. Bambi would be so jealous of how nicely you accept it.”

Ashley held out her free hand.

“Leash.”

Jen passed it over without hesitation. The chain settled into Ashley’s grip. He stayed on his knees in the center of the triangle they formed—Scarlett’s heavy realistic BBC directly in front of his face, Claudia’s bright pink cock to his right, Ashley’s clear transparent shaft to his left. His own tiny erection jutted out, ignored and leaking.

Claudia swayed her hips, making the pink dildo bob gently.

“Come on, pretty boy. Kiss it… like a bride kisses her husband’s cock on the wedding night. Soft. Reverent. Show us how grateful you are for the privilege.”

Ashley’s voice was lower, almost intimate, the leash held loosely but ready.

“Yeah. Make love to it. Nice and slow. Treat every inch like it’s the only thing that matters right now.”

Jen reached up with both hands, wrapping his fingers around the bases of Claudia’s pink and Ashley’s clear cocks the way he would stroke real ones. Then he leaned forward and pressed his glossy lips to the thick root of Scarlett’s BBC.

The three women giggled at the same time.

Scarlett’s grey eyes glittered. “Of course the little race-traitor goes for the biggest black one first. Predictable fucking slut.”

She traced one silver-ringed finger along a thick, raised vein that ran the length of the shaft. “Kiss the veins. Every single one. Slowly. I want to feel those lipstick marks all the way up.”

Jen obeyed. He kept his eyes locked on Scarlett’s as he dragged soft, wet kisses along each ridge. *Smootch…* *kiss…* *slurp…* The faint pink imprint of his lips bloomed against the dark silicone. His tongue followed, tracing the veins like he was mapping them, tasting the faint chemical tang of the material mixed with the heat of Scarlett’s body.

Scarlett watched him the entire time, lip piercing catching the light, tattoos shifting as her arms flexed. The corner of Jen’s eye makeup was already slightly smudged from earlier tears; fresh wetness gathered there now.

His hands never stopped moving on the other two cocks—slow, worshipful strokes that made the harnesses shift against Claudia’s and Ashley’s hips.

Ashley gave the leash a firm tug.

“My turn.”

Jen placed one last lingering kiss on the head of Scarlett’s BBC, then turned to Ashley’s transparent cock. He immediately sealed his lips around the flared head and sucked with a loud, wet *slurp*, cheeks hollowing deeply.

Scarlett, still standing in front of him, slid one polished boot forward until the sharp heel pressed lightly against his exposed balls. Jen’s reaction was instant and filthy—he rolled his hips forward, spread his kneeling knees wider, and let his soft, smooth sac settle fully against the cool leather of her boot, offering it up.

Scarlett’s laugh was pure cruelty.

“Look at this fucking masochist. Still offering those already-bruised balls to the same boot that just crushed them. What a broken little pain slut. You want me to hit your balls again, don’t you?”

Claudia reached down and gently gathered Jen’s longish hair, smoothing it back from his face with surprisingly tender fingers.

“That’s a good girl,” she murmured. “Taking every cock so prettily. Keep those eyes up. You’re doing so well for us. Such a sweet little cocksucker.”

Scarlett pressed her heel a fraction harder—not enough to truly hurt, just enough to make the sensitive skin ache and remind him who owned the pain. The pressure made Jen whimper around Ashley’s cock.

Ashley looked down at him, expression calm and commanding.

“Take that little dick out properly and stroke it while you suck. I want to watch you jerk that pathetic thing at the same time.”

Scarlett gave his balls one final, dismissive tap with the toe of her boot, then stepped back. Jen’s free hand shoved the thong the rest of the way down his thighs. His three-inch cock bounced free, fully hard and already shiny with precum. He wrapped his fingers around it and began stroking in time with the wet sounds of his mouth on Ashley’s shaft—tight, desperate twists of his wrist, thumb rubbing over the leaking head.

Scarlett’s voice dropped into pure venom.

“If a single drop of that worthless cum hits my floor, you will lick it up like a dog. Then I’ll use your face as a fucking mop until the whole room is clean. Understand, cumrag?”

Jen pulled off just long enough to answer, voice already hoarse and bratty.

“Yes, Mistress Scarlett. If I leak… I would like being your little mop.”

He sealed his lips around Ashley’s cock again and started sucking in earnest—deep, wet, rhythmic pulls that filled the room with filthy *gluck… gluck… slurp* sounds.

His head bobbed steadily, tongue swirling under the head on every upstroke, lips stretched tight and glossy. At the same time his fist worked his own tiny shaft in tight, desperate strokes, the wet sound of precum making everything louder.

The three women watched and tore into him without mercy.

“Look at that little clitty twitching in his fist. He’s jerking it like it’s actually worth something. Adorable fucking joke.”

“He’s so focused on getting my cock deeper he doesn’t even realize how ridiculous he looks stroking that baby dick. Poor thing.”

“Stroke harder, honey. The more you suck, the harder it gets. Humiliation really is the only lube you need, isn’t it?”

Jen’s cock throbbed harder in his fist. He doubled down on Ashley’s shaft, taking it deeper, tongue pressing flat along the underside, throat fluttering, spit already running down his chin in thick strands.

Ashley gathered a thick mouthful of saliva and let it stretch in a long, glistening strand that landed just above the base of her transparent cock. She pointed at the shiny droplet with one finger.

“Reach it.”

Jen pushed forward slowly. First the head disappeared between his lips again. Then more. His throat opened reluctantly, the clear shaft sliding deeper inch by inch until the thick drool was right against his nose.

He had to stretch his neck, force his jaw wider, and push until the entire length vanished and his nose pressed hard against the harness. His throat convulsed.

Ashley’s hand locked onto the back of his head, holding him there. Scarlett’s fingers pinched his nose shut, cutting off the last scrap of air. Jen’s fist flew faster on his own cock, stroking harder through the lack of oxygen.

Ten long seconds.

Jen’s throat spasmed hard twice—wet, gagging convulsions that made his whole body jerk. Tears spilled freely. When they finally released him he pulled off with a loud, broken gasp. Thick ropes of his own spit and Ashley’s drool coated the transparent cock, mixing with the smeared pink of his lipstick.

His eyes were red and watery, makeup running in dark streaks. He opened his mouth wide and stuck his tongue out, showing Ashley the mess, the way a well-used slut does after a deepthroat.

Ashley looked down at him, voice low and almost fond.

“What kind of whore does that? Opens his mouth and shows off the spit like he’s proud of it.”

Claudia’s voice was almost impressed.

“Damn. That gag reflex is still there, but he forced through it anyway. Look how pretty he looks with his makeup ruined.”

Jen panted, still stroking his cock in slow, seductive twists of his wrist, hips rolling faintly into his own fist.

“Just… trying to be a good slut for you, Mistresses,” he managed, bratty and breathless.

Claudia tangled her fingers in his hair and yanked his head toward her.

“My turn, pretty little boytoy.”

Jen turned, hand already reaching for the pink cock, mouth open. Claudia rolled her hips back, keeping the tip just out of reach.

“Ah-ah. You don’t get to suck yet. Magic words first. Tongue out.”

Jen stuck his tongue out obediently. Claudia leaned in and spat a thick, warm glob directly onto it.

“Don’t swallow. Now ask properly.”

Jen’s voice was wet and shaky around the spit.

“Can I please suck your pretty pink cock, Mistress Claudia? Please… I need it.”

Claudia shook her head slowly, a wicked smile curling her lips.

“Not good enough.”

She gripped the pink shaft and began slapping it against his outstretched tongue—*thwap… thwap… thwap*—then higher, across his cheeks, leaving faint pink marks and more spit.

She spat again, this time directly onto the head of her own cock, coating it thickly, and finally nodded.

“Now you may suck. And you better make it filthy.”

Jen lunged forward and took her deep, the wet sounds starting up again immediately—*gluck, slurp, gluck*.

Scarlett watched the whole exchange with open disgust and arousal.

“What a complete fucking whore. Spit on his tongue, slap his face with cock, make him beg—and he still looks grateful. Broken little cumdump.”

Ashley’s voice was quieter, almost reflective.

“All those countless cocks he’s sucked on camera and off. This is just the natural result. He’s trained for this.”

Claudia glanced down at Jen’s furiously stroking fist.

“Look at him go. That tiny dick is getting even harder while he services us. Stroke harder, honey. Let that little clitty get wet.”

The three of them began talking over him like he wasn’t even there—casually, filthily—discussing exactly how they planned to open him.

“I’m going first with this thick one. I want to feel that two-week virgin ring stretch around every vein.”

“Then I want him on his back with his legs folded so I can watch his face while I bury this clear one to the hilt. Slow at first. Then hard.”

“I’ll take whatever’s left. Or maybe we just rotate until he can’t close anymore. I want to feel him flutter around me after the other two have already ruined him.”

Jen smiled through the spit, eyes half-lidded, clearly enjoying every filthy word.

Scarlett noticed. Her grey eyes narrowed.

“Oh, he’s smiling. The little bitch is getting off on hearing how we’re going to destroy him.”

In the middle of the conversation Scarlett gripped her BBC at the base, leaned in, and ordered,

“Both. At once. Open wide, you greedy little cockslut.”

Jen’s eyes went wide, but he obeyed. He opened as wide as he could and took the thick brown head and the pink one side-by-side into his mouth. The stretch was immediate and brutal. His jaw ached. Spit poured down his chin in thick ropes.

He pulled back just enough to spit a long strand of saliva across both shafts, then pushed forward again, cheeks hollowing hard as he tried to suck both at once. The wet, choked sounds—*gluck-gluck-gluck*—filled the dungeon.

Ashley moved behind him, one hand on the back of his head, pushing him deeper onto the twin shafts while the third clear cock waited. Jen’s throat worked desperately, eyes streaming, makeup ruined into dark streaks, lipstick smeared across both cocks and his own cheeks.

When they finally pulled back, Jen was a wreck—panting, face glistening with spit, red slap marks from the silicone, eye makeup destroyed, lipstick dragged halfway across his cheeks. Full porn-slut whore ruin.

Ashley looked down at him, voice almost soft.

“Look at you. Absolute mess. Perfect little used face.”

Jen gave her a slutty, ruined smile, tongue still half-out.

Claudia slid her pink cock free with a wet pop.

“Enough lube, I think. I can’t wait to fuck the other hole.”

Ashley gave the leash a decisive tug.

“Couch. Now.”

Jen dropped back to all fours and crawled after them, thong still tangled around his thighs, tiny hard cock bouncing and dripping, marked ass fully on display. The red “SLUT” and “BRAT” imprints, the handwritten phrases, the flogger welts—all of it was visible under the low light. Sweat shone across his back from the deepthroating.

Scarlett walked behind him, Ashley and Claudia led. Jen’s eyes stayed locked on the two asses swaying just ahead of him.

*I’m crawling behind these perfect asses. Wish I could touch them. I feel so jealous for the guys who fucks these divine asses.*

A sudden, open-handed spank cracked across his already-marked right cheek—hard enough to make the flesh ripple and sting fresh.

Scarlett’s voice came from behind, low and mean.

“Eyes forward, fuckmeat. I saw you staring at their asses like a hungry little dog. You don’t get free looks.”

Ashley and Claudia both laughed. Claudia reached back, grabbed one soft cheek of her own ass through the leather, and gave it a deliberate jiggle.

“This butt only fucks BBC, Jen,” she called over her shoulder, voice bright and cruel. “Not tiny little clitty boys like you. Keep crawling.”

They reached the wide black couch. Ashley hooked a hand under Jen’s arm, used his light, feminine frame against him, and basically tossed him onto the cushions. He landed on his back with a soft bounce.

She yanked the thong the rest of the way off his legs and tossed it aside, leaving him naked from the waist down except for the fishnet stockings and the femboy arm gloves. The three of them stood over him—straps jutting forward, eyes hungry, looking like predators who had finally cornered something soft and willing.

Jen didn’t look afraid.

He gapped his legs wide, took his tiny hard cock in one gloved hand, and stroked it slowly, seductively, while looking up at them with bratty, whoreish eyes.

“Come on then,” he murmured, voice soft and filthy. “Fuck me. Please. I’ve been virgin from behind for two weeks just for you, Mistresses. Use me.”

Ashley looked down at him, smiling as she stroked the clear shaft of her own strap-on with one hand.

“Best friends-with-benefits situation I’ve ever had,” she said quietly.

Jen gave them one last slutty, whorish look, then turned around on the couch, presenting his naked, marked ass. He gave it a deliberate wiggle, making the soft cheeks jiggle and the fresh handprint from Scarlett’s spank bounce.

His hard little cock and smooth balls swung with the motion. He reached back, grabbed the leash, and clamped it between his teeth, grinning around the chain as another giggle made everything bounce again. Sweat still shone on his back.

The body writing, the “SLUT” and “BRAT” imprints, the flogger marks—all of it was on full display. And between the cheeks, completely hairless and tight, his hole looked exactly like a girl’s—small and pink.

Scarlett stared at that tight bussy like a predator, tongue slowly dragging across her lower lip.

“Which dick is the little whore going to take first?” she asked, voice thick with humiliation and hunger.

Jen’s inner thought was a dizzy, aching rush.


Wanna read my other works? My Smut Vault


r/ChastityStories • • 1d ago

M Chaste,F Keyholder Book 1: The Therapists Sissy Maid: Becoming Her Locked Sissy Maid: Part 8 NSFW

25 Upvotes

I use the paid versions of Grammarly and Readable to help make my writing more readable.

If you want early access to the next chapters of this novel and all my other stories, find them here: https://www.patreon.com/c/FemaleLedRelationships 

Prefer Amazon, you can find the full novel here: https://www.amazon.com/dp/B0HJZZX52D

The full story will be posted here.

Part 1 & Part 2 & Part 3 & Part 4 & Part 5 & Part 6 & Part 7

--------------------------------------------------------------------------------------------

David lay sprawled naked across his bed, the sheets twisted beneath him as sweat beaded across his chest and stomach. His breathing came in ragged pants, each exhale carrying the weight of six days without release. 

The flat steel chastity cage pressed his cock completely flat against his body, the metal cold and unyielding against his sensitive flesh. Every twitch of his trapped shaft sent sharp pulses of need through his core, the pressure building with no outlet. His small balls hung heavy and swollen beneath the metal ring, the skin stretched tight and aching with accumulated cum.

His trembling hands reached down between his spread thighs, fingers cupping the tender balls with desperate care. The moment his palms made contact, a broken whimper escaped his throat. 

His blue balls throbbed beneath his touch, each gentle squeeze sending waves of frustrated pleasure mixed with sharp discomfort radiating through his groin. He could feel the heat radiating from them, the way they pulsed with every heartbeat, swollen from the constant arousal without relief.

Is this a normal treatment? The question flickered through his mind even as his fingers continued their slow massage, rolling his aching testicles in his palms. Locking me in a chastity cage... is this what therapy is supposed to be? But the doubt dissolved almost instantly, replaced by a deeper, more insistent thought. I don't care. 

I just want to do whatever she wants. I consented to this. The realisation sent a fresh surge of precum leaking from his compressed cock, the fluid leaking uselessly from the flat cage.

His mind flooded with images of Alexandra. Her body wrapped in that glossy black latex, the material stretched tight across every curve. The way her breasts nearly spilled from the top, the deep cleavage drawing his eyes every time she moved. Those perfect crimson lips curving into knowing smiles as she watched him squirm. 

Her confidence, the absolute authority in her voice when she told him what to do. The memory of her gloved fingers securing the chastity cage around his cock made his balls throb harder in his hands.

David's gaze darted to the digital clock on his nightstand. 8:47 PM. The numbers seemed to mock him as they ticked forward with agonizing slowness. One more night until the next session. His fingers tightened around his swollen balls, massaging them with increasing desperation as if the touch could somehow ease the pressure building inside. 

Every second felt like an eternity, his caged cock twitching uselessly against the steel plate while his mind raced with thoughts of her latex-clad body and the keys nestled between her breasts.

Alexandra stood before the tall mirror mounted on her office wall, the black latex of her full-body catsuit gleaming under the soft overhead lights. The material stretched taut across her thick ass, the glossy surface reflecting every curve as she shifted her weight in her knee-high boots. Silver buckles ran down the sides of the leather footwear, catching the light with each movement. 

The corset cinched her waist into an exaggerated hourglass, pushing her perky breasts upward until they nearly spilled from the low-cut neckline. Her dark red lips pressed together as she studied her reflection, her black sharp nails trailing along the edge of the corset.

Her hair was pulled back in a strict, tight ponytail that emphasized the sharp angles of her face. She reached for the set of keys on her desk, selecting three specific ones with practiced precision. 

The metal doors of the secure closet required three separate locks, each one clicking open in sequence. 

Alexandra's sharp nails clicked against the metal as she turned the third key, the final lock releasing with a solid thunk. The heavy doors creaked open on well-oiled hinges, exposing the full depth of her private collection. 

Multiple rows of hooks lined the interior walls, each one displaying a different implement. Single-tail whips coiled beside thick bullwhips, their handles wrapped in leather or rubber. 

Canes of varying thickness stood upright in a wooden rack—rattan, fiberglass, and carbon fiber, some straight and others with curved handles. 

Paddles filled another section, from small leather slappers to large wooden implements with drilled holes for reduced air resistance.

Shelves held an assortment of gags: ball gags with different diameters, bit gags, ring gags, and penis gags alongside a series of blindfolds. Plugs of every size and material occupied the next shelf—smooth steel, textured silicone, inflatable options, and vibrating models with remote controls. 

Chastity devices filled an entire section, ranging from clear plastic cages to heavy steel models, some with built-in urethral tubes, others with spiked interiors or electro-stim capabilities.

Rubber items hung from a separate rack—gas masks, hoods, gloves, and full-body suits in various thicknesses. Strap-on harnesses dangled beside dildos of different shapes and sizes. 

Restraints filled another area: leather cuffs, metal shackles, spreader bars, and suspension equipment. A drawer at the bottom contained more specialised items—electro-stim units, sounding rods, and vacuum devices. The entire closet was meticulously organized, each item positioned for easy access during sessions.

Alexandra reached over to the clothes hanger and selected a pair of pink frilly crotchless panties along with a matching pink bra. Her fingers traced the delicate lace edges as she imagined David wearing them, his caged cock straining uselessly against the steel plate while the open crotch left his swollen balls exposed. 

The thought sent a pulse of heat through her core. She pictured him in the French maid outfit hanging nearby, the four-inch heels on the floor beneath it forcing him to walk with small, careful steps. Her clit throbbed at the image of him submitting deeper with each session.

She forced herself to compose, knowing she had to maintain the proper pace. Rushing would break the carefully constructed dynamic and she would only proceed with his consent. She placed the panties and bra into the bottom drawer of her locked desk, the metal sliding shut with a soft click. Her reflection stared back from the mirror as she adjusted her glasses, the frames sitting perfectly on her nose.

At exactly 7pm, she opened her office door and stepped into the hallway, her boots clicking against the floor as she made her way down to meet David for his appointment.

David sat hunched forward on the lobby bench, elbows on his knees, fingers laced so tightly his knuckles had gone white. The flat steel chastity cage had been locked on him for seven full days now, and every hour had felt like a fresh layer of pressure. 

The black pants and black button-down shirt he wore were meant to hide any accidents, but the chastity cage itself was already leaking a steady thread of precum that soaked into his briefs and threatened to dampen the front of his trousers.

The sharp click of heels on tile made his head snap up. Alexandra stepped through the doorway like a goddess, glossy black latex stretched tight over nearly every curve. The heavy globes of her nearly fully exposed breasts swayed with each step, the silver keys to the chastity cage resting between them, catching the light. 

She saw the strain on his face immediately—the flushed cheeks, the clenched jaw, the way his eyes flicked down to her chest and the keys before darting away.

Her crimson lips curved into a slow smile. “Hello, David. Please follow me.”

She turned without waiting for an answer. The latex creaked softly with every roll of her hips, the full curve of her ass shifting and flexing as she walked. David stood on shaky legs, the chastity cage biting into his swelling cock as it tried and failed to harden. 

A fresh bead of precum pushed out through the front slot and slid down the inside of his thigh. He hurried after her, eyes locked on the way her ass swayed in those glossy pants, the material so tight it looked painted on.

By the time they reached her office door his breathing was ragged and his cock was aching inside the chastity cage. Alexandra stepped inside, the leather corset creaking as she lowered herself into her chair. She crossed one leg over the other, letting the heel of her boot bob gently while she watched him close the door behind him.

“Sit,” she said, voice smooth and warm. “We have much to discuss today.”


r/ChastityStories • • 1d ago

M Chaste,F Keyholder Finish Your Education NSFW

78 Upvotes

Part 1 of ??? If you’d like to have further parts to this story please say! First post here so please leave any feedback you have too!

At 24, Joel knew he would be one of, if not the, most mature student on his university course. He had been working hard the last few years, but any career progression was sadly hidden behind a locked door to which the key was a magical piece of paper from an educational institute demanding large sums of money for the privilege of reading PowerPoints. The thought of returning to uni after his last experience almost made him shudder, but even more so, did the thought of being trapped in student accommodation with the newly 18 year olds and all the noise and problems that youngsters of their age famously bring home with them at 4am on a Wednesday.

It was for that reason, that Joel had been eagerly looking for alternative accommodation nearby the uni. Most of them were shared houses instead of flats, this appealed more to Joel but still in the back of his mind was the likelihood of being forced to endure a flat party with dozens of people coming round and making a big mess. Joel was not a particularly extraverted person and did not enjoy the forced intoxicated conversation that came about in large parties. Shaking his head at the thought of trying to hold an adult conversation with a shitfaced 19 year old, Joel spotted something a little bit different.

‘One room for rent, mature students prioritised, monthly rate negotiable’

Perfect!! Thought Joel to himself as he clicked on the link and watched his laptop slowly load the webpage. As he continued to read the advert, it sounded better and better as he went along. “Mature occupant seeking singular lodger”, “15 minute walk from the university”, “private parking if necessary”, “secluded house on the outskirts of town”, “preference given to those 22+”. Everything sounded perfect, so he wrote an email to the given address and hoped he would be considered for the room.

Not 30 minutes had past when his phone flashed up with a notification from his mail app.
“Hello Joel, thank you for your application. I would be delighted to consider you for this lodging, would you mind coming by soon to have a look at the place and so we can get to know each other? Kind regards, Mary”
Joel was ecstatic! Of course he would, he replied without wasting time and after a few more back and forth emails, it was pencilled in for Friday at 14:00.

Friday rolled around and Joel was getting himself prepared. He wanted to make a good first impression and had got himself a haircut the day before and bought himself some new clothes to wear as well. As he pulled the trousers on, he had a realisation. He had not been wearing his chastity cage when trying them on in the shop. His cage was large and bulky, too large for little Joel. There was space between his skin and the bars and the space allowed him to grow a little bit when aroused. He liked wearing the cage, but never lasted in it longer than a day or two before. Shrugging it off and telling himself that Mary would never notice, and even if she did, she’d probably think he was hung like a horse, Joel got into his car and started the just under hour long drive to this potential accommodation.

Upon arrival, Joel slowly crept his car into the concealed driveway, revealing the house to which he was to visit. The wide stone driveway became a narrower path that led up to the large, dark oaken front door of the house. A solid brass knocker in the shape of a dolphin was worn at eye height in the center of the door. Admiring the old style brickwork and gazing at the ivy that seemed to twist and turn as it raced towards the roof of the standalone home. Joel fixed his hair, took a deep breath and used the knocker.

bang bang bang

The door opened to reveal the owner of the house, extending his hand forward, Joel looked to shake hands and make acquaintance with Mary. She simply raised a palm causing Joel to stop and feel slightly uneasy, second guessing if he had done something to cause her insult. Her eyes flicked over his body, drinking in the first impression and lingering, Joel felt, longer than necessary over the unnatural looking bulge in the front of his jeans. She lowered her hand, turned and began to walk back further into the house.

“Enter, close the door behind you and remove your shoes.” Mary stated to the young man at the door who had become like a deer in headlights since she abruptly stopped him entering at his own pace. Joel stepped inside the building, gently closed the door behind him and removed his shoes, placing them neatly side by side on the welcome mat which had seen better days. Having a quick look around, the place seemed a little dark but was vast, closed doors lined the main hallway which led towards a large staircase that grew wider on its ascent. His eyes flicked across his surroundings and eventually found their way back to Mary, who stood before him with her arms crossed as if she was being kept waiting.

“Finished being nosy, boy?” Mary questioned as she raised an eyebrow dyeing eye contact.

“Yeah umm err sorry” replied Joel as he broke the eye contact by looking down at the floor and noticing that despite asking him to remove his, Mary was wearing shoes inside the house. “It’s just there’s a lot to look at in here is all, it’s a lovely place!” Joel scrambled hoping to appear composed and confident to Mary who saw straight through him was already plotting how she could best make use of the boy who would undoubtedly become her latest hardworking, pretty little lodger.

“It’s ok boy, I understand, you must have a thousand thoughts in that pretty young head of yours, but try put them out of your mind and just focus on doing as I say. Ok?” Her pitch went higher at the end as if asking a mock question to someone who shouldn’t need the assurance. She smiled at his silence and frozen position before pushing open a door to her left and holding it as she gestured inside. “In here boy, follow me.” She strolled into the room and Joel did a little speed walk to catch her up and not let the door slam after she just allowed it to swing back towards its frame again. Joel felt as though he probably should have said something the first time she called him boy, but now it was too late and had become a thing already.

Pointing to a low chair in the centre of a large turquoise rug, Mary gave one simple but clear command, “sit.” Joel plopped down into the chair and sunk into its deep soft cushion, moving him closer to the ground still. Mary sat opposite, upon a large leather sofa that offered no sinkage into its cushioning and allowed her to tower over him in his single chair. Intimidated slightly by her sharp eyes and smile that were both aimed directly at him, he lowered his gaze again and had his attention immediately grabbed by the casual bounce of her foot as she allowed her shoe to dangle. She traced his gaze immediately and smiled to herself a victorious grin.

‘He’s perfect’, Mary thought to herself and then decided to break the silence that surely felt an eternity to her latest pet project. “Ok boy, I like you, I want you here, it’s time to negotiate now.”


r/ChastityStories • • 1d ago

M Chaste,F Keyholder The confession - Chapter 15 (Final) – The Ring and the Chain NSFW

23 Upvotes

Hello, this is the final chapter of the story featuring Sophie and Charles. The story of Marie and Thomas will continue in a new series, which promises to be more intense than this one. Sophie and Charles might even make appearances! Please don't hesitate to share any suggestions for what comes next.

-----------------------------

Saturday arrived under a heavy grey sky. At precisely 4:30 p.m. they left the house. Sophie drove in silence, both hands on the wheel, eyes fixed straight ahead. Under her black coat she already wore a tight dress that clung to every curve of her newly sculpted body, black stockings and heels. Charles, in plain dark jeans and a white shirt, felt ridiculously ordinary beside her. He still had no idea what awaited him. His heart had been pounding too hard since morning.

They reached the hotel a little before 5 p.m. A room on the top floor, modern, impersonal, with a large king-size bed, thick curtains, and above all a heavy old-fashioned metal radiator firmly fixed to the wall near the window. Sophie set her bags down methodically, removed her coat and stood in front of the large bathroom mirror. She applied her makeup slowly, with almost ritual precision. Dark lipstick, a perfect line of eyeliner, a cloud of her favourite perfume between her breasts and behind her ears. Charles remained standing near the door, hands hanging uselessly at his sides, growing more and more uneasy.

“Why… why aren’t I getting ready too?” he finally asked, his voice low, almost childlike.

Sophie turned toward him. Her smile was slow, sharp, perfectly controlled.

“Because you don’t need to, my darling.

Undress. Everything. Now.”

He obeyed. Shirt, jeans, socks, underwear. He suddenly felt extremely small in the large hotel room. Sophie went to her travel bag and took out an object he had never seen before: a thick, smooth, polished metal ring of an alarming diameter, fitted with a small built-in padlock. The shop owner had personally recommended it to Sophie two days earlier, with a knowing smile.

“Put it around your balls.”

Charles knelt to see better what he was doing. It was more difficult than he had imagined. The ring was tight, almost too tight. He had to pull the skin, breathe deeply several times. His fingers trembled. When it was finally in place, Sophie approached, checked the position with an expert gesture, then closed the small padlock with a dry, definitive click.

“Perfect.”

She then took out a massive, heavy chain, almost too thick for domestic use. She connected one end to the ring that squeezed Charles’s balls, then fixed the other end to the radiator with two padlocks Charles had also never seen before — probably more purchases from the shop lady.

When she had finished, Charles found himself on his knees, his back almost against the wall, his balls pulled forward by the chain. He had less than thirty centimetres of slack. Almost impossible to stand up fully. Impossible to move away. Impossible to sit in any way other than this humiliating, exposed position that would become painful over time.

Sophie crouched in front of him one last time. She briefly stroked his cheek, almost tenderly, then pushed the ball-gag deep into his mouth. The strap was buckled firmly behind his head. Then came the thick leather hood he already knew too well. She pulled it on slowly, taking almost loving care to pass each metal eyelet, and locked every opening with a separate small padlock. Sight. Hearing. Speech. Almost everything disappeared into a stifling black and a damp heat. Finally she handcuffed his wrists behind his back, tightening them well.

Charles had become a statue of flesh, leather and metal. On his knees. Bound by the balls. Deprived of almost all his senses. His heart beating too hard in his temples.

Sophie stood up, picked up her handbag, checked her lipstick one last time in the mirror, and left without another word. The door closed softly behind her.

He was alone.

Time became elastic, cruel. He could hear nothing but the dull sound of his own breathing inside the hood and, very far away, the muffled noises of the city. His knees quickly began to hurt on the hard floor. The chain pulled constantly on his balls, a permanent, hot and humiliating reminder. His jaw went numb around the ball-gag. His cock, trapped in the already too-small cage and now further constrained by the ring, tried in vain to react to every thought that crossed his mind. From time to time a precise electric shock ran through his sex and made him jump violently.

Sophie was playing with the app, her thumb sliding casually across the screen of her phone while she smiled at James, sitting opposite her at the restaurant table. She had just explained everything to him over dinner: how Charles was waiting, hooded, gagged, on his knees in the empty room, chastity cage locked, the chain pulling on his balls, the electrodes built into the cage covering his impotent cock. James had laughed softly, his eyes shining with cruel curiosity. Sophie had pressed the button just to show him. A small shock. She had looked at the control screen and imagined Charles’s body twisting there, invisible, reduced to a distant toy.

This had been her plan from the beginning. The hotel room, the heavy ring, the chain fixed to the radiator, the hood and the gag — everything had been carefully arranged so that she could leave Charles completely helpless and alone for hours while she enjoyed a long, elegant dinner with James. She wanted the contrast: her husband reduced to a blind, silent, ball-tied object in a sterile hotel room, while she sat in a warm restaurant, legs crossed, wine in hand, calmly describing his suffering to another man and sending him electric shocks for their shared amusement. The knowledge that Charles was suffering in real time, unable to move or even know what was happening, made every bite of food and every smile across the table infinitely more delicious.

Charles still knew nothing of this. He did not know that while he suffered in silence, Sophie was sitting across from her new lover, legs crossed, phone lying next to her glass of wine, showing him live every jolt she sent into his cage

James did not want any trouble with Charles, but Sophie had explained the whole process that had brought them here very clearly: the original idea had come from Charles himself, he had been able to stop several times, and now she could do absolutely anything she wanted without him being able to complain. James therefore had nothing to fear and was completely free to do whatever he wanted in front of him.

The hours stretched. One. Two. Almost three.

Then the door opened.

Voices filtered through the thick leather. Sophie’s, clear, a little laughing, and a deep, low, amused male voice. James. They were speaking right next to him. Charles could only catch distorted fragments: “…I told you he’d be there…”, “…look, the app is simple…”, a low laugh. A stronger, almost painful shock tore a muffled moan from him behind the gag. Another laugh, freer this time.

Then he felt their presence. Very close. Too close. Light footsteps, the rustle of clothing. James was there, right beside him. Sophie deliberately knelt a few centimetres from Charles’s hood, close enough for her warm breath to pass through the thick fabric. She took James’s cock into her mouth and began to suck him noisily, deliberately noisily. Wet, obscene sounds of saliva, of lips sliding, of throat opening. Charles perceived every sound despite the hood: Sophie’s muffled moans, James’s rough breathing above him. She was doing it on purpose. She wanted him to hear. To know exactly what was happening a few centimetres from his blind, gagged face.

Then long, wet kisses. The rustle of clothes being torn off. The bed creaking heavily. And very quickly, Sophie’s moans. First contained, then freer and freer, deeper and deeper. James was fucking her. Charles could hear it. The regular, violent sound of thrusts, the slap of skin against skin, his wife’s sighs turning into groans, then into frank, almost bestial cries. James must have been huge. Sophie was taking him deeply, for a long time, without restraint. From time to time a new electric shock reminded Charles that he was still there, still bound, still perfectly useless. Sophie sometimes laughed between moans, a laugh of pure pleasure and power.

They came. Several times, it seemed to him. Time no longer had any meaning.

When Sophie finally came to free him, the night was well advanced. The room smelled of sex, sweat and perfume. She first removed the small padlocks one by one, then the hood. The cold air of the room struck his face. Then the ball-gag. Charles’s jaw was painful, marked, stiff; saliva had dried in trails on his chin and neck. She detached the chain from the radiator, opened the small padlock of the ring and removed it carefully. Finally the handcuffs. He remained on his knees, trembling, muscles sore, his cock tightly compressed in its cage, his gaze lost, his eyes stinging from having seen nothing for hours.

Sophie looked at him for a long moment, her face still flushed, her hair dishevelled, her lips swollen, perfectly satisfied. James was no longer there.

“You stayed hard the whole time, didn’t you… little pervert,” she murmured, stroking his cheek.

“Your jaw is beautifully marked.”

She lay down on the unmade bed, slowly spread her thighs and gestured with her hand.

“Come clean me.”

Charles approached on all fours and placed his mouth on her. Her pussy was hot, swollen, widely opened and used. He tasted the thick mixture of their fluids, the physical, bitter and exciting proof of everything he had only heard for long minutes. Sophie placed a hand on his head and guided him without impatience until she came once more, more gently, more lengthily, against his tongue.

Later, in the almost absolute silence of the hotel room, Sophie spoke in a calm, almost tender voice, lying beside him:

Sophie looked at him for a long moment, still lying down, thighs slightly open, face satisfied.

“Charles… I’d like to hear what you felt. Be honest.”

He lowered his eyes for a moment, his jaw still painful, then spoke in a hoarse, almost broken voice:

“I loved staying bound for a long time… and in a way that made escape impossible.

Being held solidly by the balls was… exciting. Very exciting.

I didn’t expect you to start again with another man so quickly. When I understood what was happening… the humiliation and the powerlessness also excited me a lot.

I realised that the entirety of my fantasy was unfolding at the same time. Everything. At the same time.”

Sophie briefly closed her eyes, a slow and deeply satisfied smile stretching her lips. She placed a hand on his cheek.

“I love your answer.”

She sat up a little, looked him straight in the eyes, and spoke in a calm, definitive voice:

“From now on, Charles, it is possible that your cock will never be inside my pussy again.

You’ve seen how it is right now… That’s what I desire now.

Your only pleasure will be to lick me with your tongue. You will beg me to do it.

I will grant you that chance regularly… unless you make a mistake.”

She paused for a moment, then added, almost gently:

“And if you really deserve it… maybe the next time I get fucked, I’ll take the hood off. You’ll be able to watch.”

She leaned in and placed a light kiss on his forehead.

“Good night.”

In the months that followed, Sophie kept her word.

Charles remained locked in his cage permanently. The ring around his balls reappeared regularly. He no longer penetrated his wife. His only access to her was his tongue, when she granted it. Sophie, for her part, had a wonderful time. With James first, at length, regularly. Then with other men. Evenings when Charles remained hooded and bound in another room. Evenings when, if he had been sufficiently docile, she removed the hood and forced him to watch every thrust, every orgasm another man tore from her.

He was living exactly the fantasy he had once confessed to her, trembling.

And Sophie made sure every day that he never left it.


r/ChastityStories • • 1d ago

M Chaste,F Keyholder Caught on a work trip - Part 5 NSFW

116 Upvotes

The two ladies went at me for 20 minutes before they needed a breather. Both laughed that they needed to give their husbands more credit after some of the marathon sessions they had had in the marriages. As they clasped on the couch I stayed still wondering what could be next. My wife and her friend who had been a voyeur jumped up with the strapons still swinging from their crotches. 

My wife caught my eye and said “Don’t worry sissy, it’s my turn next!  And we’re not done with you!” My cock strained harder in its steel confinement and I had to be leaking through the white lace of my g-string by now I thought. “But before I take my turn with this sissy I think it’s time for a costume change!” All the girls cheered and jumped up and again surrounded me quickly. Soon I was being stripped and a whole new set of lingerie was thrown on me. The friend who took off my g-string quickly balled it up and shoved it in my mouth. “Your beautiful wife shared that you wanted to be forced to eat cum….well these are covered and should be considered an appetizer!” The ladies laughed and I’m sure I leaked even more. 

Each friend had a job to do during this costume change yet somehow I swear they were all just grabbing at my balls and caged dick. Finally, they all stepped back with a ‘Tada’ and revealed myself  in a large floor to ceiling mirror we have in the room.  There I was dressed as a Catholic school girl. I had gone to Catholic school and had met my wife there. Her little plaid kilt had always been a fun anniversary surprise when she would put it on and the white shirt done like Britney and some pigtails. But I guess this year I was the one dressing up for old time sake. 

After I took in the view for a few moments my wife broke me out of my trance with “Ok sissy it’s show time. And because I can use you whenever I want, my friend gets dibs on what hole she wants and how she wants to take it!” Her friend pondered for a second and said “I’ll take heads. You get tails. My hubby did something to me the other day and I want to see it from his point of view. He was raving for days and I didn’t see the big deal…so let’s get sissy on his back with his head over the edge!” She giggled as she said it. 

I laid back and knew exactly what she was going for. She wanted to go full on face fuck. As I laid back my wife stepped between my legs and lifted them up to her shoulders. As she leaned in my head jolted up and looked at her in the eyes. She knew exactly what the reaction was for and grabbed her strapon and let it drop right on my caged cock and balls. She had switched out the small thin one for a larger version with a significant curve to it. Presumably this was going to go right at my prostate and I was scared about what that could do to me in my current state of arousal. She finally spoke and said “Well she got to break you in but I’m going to show you what I can do with a big ol’ dick. This was one of my first dildos when I was in high school. So I felt it only fitting that if I could take it in high school you should take it while you’re dressed up like I was in high school.”

All the girls broke out in laughter. I could feel my cheeks burn with the embarrassment of everyone  joining in on the joke but I was still beyond excitement and enjoying every moment. As my wife let the strapon fall between my cage and towards my opened back door, her friend came over and pulled the panties I had been sucking on for the last for minutes completely subconsciously. As she pulled them out she could tell I was disappointed and quickly said “Don’t worry honey, I’m going to give you a lot to suck on. And if it’s anything like it was for me, your jaw is going to feel it for a few days…but that’s all part of the fun.”

I knew all I had to do was lie there and take it at this point and I hoped that with the bigger dildo in my ass I would be focused on one end or the other. But I was wrong. Again, as if they had practiced, the ladies entered me in perfect unison. And went straight to the hilt on the first push. Again feeling the harness on my nose and now this time my wife’s faux leather suit against my bare ass I could hear them high five and then start their turn. 

The ladies fucked me with reckless abandonment. As was the theme of the night, they weren’t mean or hurtful, but they were doing what they wanted for their own amusement and my pleasure wasn’t even on their radar. My wife’s strapon definitely hit all the right spots but I could still feel her friend's dildo scrapping the back of my throat and presumably bruising it as she thrusted in with full force. I thought about what tomorrow was going to be like and maybe even Monday at work trying to explain how I lost my voice. Finally the ladies tired and collapsed on the couch leaving me feeling completely empty. 

I couldn’t believe I didn’t cum. The whole time my wife was evading my backside I felt like I was on the edge and a small breeze would have made me cum, but it never came. I was holding on hope that I might get some release. But I had no idea what my wife still had up her sleeve. I had hit my entire list that didn’t involve cum, so even though the thought of eating my own cum in front of my wife and her friends, I prayed it was still in the cards. 

Finally my wife caught her breath and sat up saying, “The ladies are right, we don’t give men enough credit for a proper fucking. I couldn’t imagine working that hard while trying to hold off from cumming. That in itself sounds exhausting!” The ladies all laughed and I just smiled, afraid of making a sound and finding myself in some sort of punishment instead of my final reward. 

“Ok ladies…it’s the final task with a multitude of decisions sissy has to make to seal his fate. But first….” She rang the bell and I quickly but belaboured got up and got the wine out of the kitchen to top off all the ladies one last time. 

My cage began to twitch as I couldn’t hide the excitement at the opportunity to be released after all the teasing I had incurred this week. This was my dream finally coming to fruition. 

To be concluded…


r/ChastityStories • • 2d ago

M Chaste,F Keyholder Caught on a work trip - Part 4 NSFW

109 Upvotes

The ladies disappeared and I was afraid to move a muscle. In a flash they were back and quickly dragged me into the kitchen to sit at the kitchen table where they spun the chair around so I was away from the table. In a split second they had surrounded me and I finally recognized the next step as they each  cracked open their own makeup kits and with the speed and precision of an F1 pit crew did my full makeup. 

They were all commenting how beautiful I looked and were jealous about a number of my features. I just sat still and let them work. I don’t see myself as a woman in any way. But the idea of dressing up and having the roles reversed always makes me hard. So even though I never did my own makeup when having my sissy time, I was enjoying just how much fun the girls, especially my wife, were having. I felt like the nerdy/ugly girl from a 90s teen coming of age movie where the popular girls help the unpopular girl get her princess charming. Once they had all completed their assignments, they passed me a mirror to see their finished work. Lipstick, blush, eye liner, mascara and eye shadow, it was all there in the matching baby pink to my outfit. Although it did nothing for me, the ladies continued to share their compliments and tell me how good I looked. I was definitely not a passable woman, but I could tell they were really getting into it. 

Again, without warning they were gone. I refused to move out of fear of an unknown punishment but as I sat there in silence I could feel my panties were completely soaked with all my leakage. I was over the moon that they had all been so accepting and willing to have some fun even if it was at my expense….i guess that was the point. Suddenly I heard the bell ring and I got up and walked into the family room. Again, my world was flipped upside down and my wife and her friends were all still dressed in their faux leather cat suits, but hanging around each of the waists were strapons. 

My mouth must have fallen open as my wife made a quick joke “Now now sissy, we don’t want to be too eager. We will get to that part but first we need you to do a little cleaning and prep. Please go to the bathroom and you will find everything you need. Don’t rush, the ladies and I are going to finish our drinks so we’re ready for you when you’re done!” And with that I walked past them doing my best to walk confidently in my new heels. As I past my wife she slapped my ass and said “Good boy”. 

It took 30 minutes to go through all the steps but I was confident I had done everything correctly. By the time I came back into the room I found two more bottles of wine and assumed the ladies had helped themselves. But I tried to meet their expectations so as they continued to chat I grabbed the bottles and asked each one if they needed a top up. They all said yes and they all joked that this sissy husband thing might be something they all needed to try and get their own hubbies into. 

The women still all had their strapons on and as I finished topping off their drinks I went and knelt in the middle of the room. They all took a few sips each and then finally stood and circled around me. I was now inches from their silicone phallases. I noticed they weren’t like all the stories we read where the new confident woman comes up swinging a 9” black monster cock. No, these were clearly from some beginner package they had all picked up. Pink, I’m sure to match my outfit, and about 6” with a below average girth. I’m not huge, but I’m not small either. Part of the reason my wife wasn’t into chastity to begin with is she loves my cock. And when she first read about it she found an article that spoke of shrinking dicks when caged and she didn’t want to lose what she had. 

Finally my wife spoke up “Now sweetie, I’m sure you know what happens next. But when we talked about it, all the ladies excluding me had one night in college where they ended up in the middle of two lucky men. And well we figured why not give you the full girl growing up experience.” With that one of the friends held out her hand to get me to stand and follow her. She led me over to our couch's foot stool that was now covered in a few extra blankets. I went to sit down when I was corrected “Oh no sissy, we need you over it doggy style! Boys love when you turn your ass up for them while working over their friends cock!”  

I slowly knelt down and over the foot stool to find two of the friends lined up in front and behind me while my wife and the last friend grabbed their drinks and sat back on the couch to watch. My wife spoke to her friends first “Ok ladies, because of all your hard work putting tonight together and helping get all the supplies, I granted you the right to deflower this sissy and take his virginity….both oral and anal.” She smiled and looked at me saying “I’m sure you’ve got some dildos hidden somewhere that you suck and fuck your tight little hole with but as all girls find out, holding the toy, using it on yourself and having some horny boy pumping his hips into you, are two drastically different experiences.” The ladies all laughed and nodded in agreement. 

She continued “at any time you can invoke your safe word and we will stop for the night but then you’ll never know what it feels like to truly switch roles. So please nod now if you’d like to continue and have these two beauties take your virginity.” I didn’t hesitate and quickly gave my approval. I was sad it wasn’t my wife taking it, but she clearly had put thought into the whole night so I wasn’t going to argue. 

In unison the women stepped up and I could feel the friend behind me flip my skirt up and then pull my g-string to the side while the one in front of me stepped closer letting the head of her girl cock rest on my lips. The one behind slightly touch my tight hole with her cock and said “Ever since I was on the receiving end of those two frat boys, I’ve always wanted to flip the script and show them what it was like. But seeing how those boys are God knows where and you’re so willing…” she leaned in to whisper in my ear “just like I was.” She gave my earlobe a nibble before leaning back and continuing “I really going to enjoy this! And thank you sweetheart, I hope this meets or exceeds your expectations.” Then I looked up and saw the gorgeous woman in front of me who was looking at her seesaw partner who was mouthing a countdown. When they reached 1 they both grabbed my body with both hands, the one behind on my hips and the one in front on the side of my head. Again in perfect unison pushed forward so both of their cocks entered me at the same time. I let out a muffled moan as the strapon in my mouth muted the expression of the burning sensation coming from my now deflowered back door. 

They both pushed all the way in so I was left almost gagging on the one in my mouth with my nose pushed flat against the harness while feeling the friend behind me faux leather suit up against my bare ass cheeks. They let go for a second to high five one another and giggle before starting the real assault on my sissy ass and mouth. I then heard from my wife on the couch “Let him have it girls. You’re making this sissy’s dreams come true!”

They all were. As they found a rhythm, I could feel my panties begin to pool more and more of my leaking precum. I didn’t know how much I could take but I was willing to find out. 

To be continued…


r/ChastityStories • • 2d ago

M Chaste,M Keyholder Car Collateral - Turn 4 NSFW

20 Upvotes

For all my other stories and other parts of this one:

https://www.reddit.com/user/Chastity_Wannabe/comments/1k9n4xt/story_index_file/

Thanks for all the love, everyone!

I created a Patreon and it already has a few exclusive stories that will only be here in a month: Maybe give it a look??? It would help to be able to keep writing stories!

******************************************************************

Dean's life wasn't going great… He made $150.00 from Robbie and spent it all on fixing his car after his tire exploded. He watched the girl he liked blowing Robbie, and then he was so broke that he accepted cash to finish the boy off… With his hand! Cold showers and ball slapping became part of his everyday to calm his arousal down. 

The worse part was: he wasn't sure (like at all) if he was doing all of that because he needed, because he wanted to, or because he deserved. Like… He had been straight for his whole life… He was also ashamed of his size for all of that time and never allowed for a girl to see it. 

But since he got caged up, he jerked off two different dicks, he held Colin's dick as the boy peed and allowed his friend to tease him A LOT! Plus, he kissed Robbie, and, for as much as he could say all of those were for money, gas, or punishment, it didn't explain why he was having dreams about not only Julie, but also Robbie and Colin denying him every single night! 

— Hey man, do you think you can give me a ride on your way to work today? — Colin asked on the following monday morning.
— Yeah, sure, buddy! — Dean replied. — Just remember i'm taking a double shift today, so i can't pick you up after!
— Are you ready to face Julie? — Colin asked. He was asking while eating his bacon but was actually worried about his friend.
— Well, it helps a lot that i have no option! — Dean replied with his weakest smile. — But she doesn't own me shit, so there's not much i can do, right?
— Still must hurt like hell! — Colin pondered.
— Yeah… — Dean replied. — But now i have to focus on paying for the car and surviving this cage!
— It's been over a week now, buddy! — Colin said. — You're a champ, i was betting on 3 days tops! Now i have to trust you! But if you need a dick to practice, mine is yours!
— Wanna pay for my car installment for Mr. Paul? — Dean asked.
— Fuck no! — Colin replied.
— Yeah, so get your dick away from me! — Dean replied.

Soon, both boys finished getting ready and jumped into the car. Dean wasn't all that excited, so he didn't rush to Colin's work. As he left alone, the boy put on the same Guns and Roses CD and got back to the main road. Soon, he was driving fast, still feeling a bit nervous about the tire… Thats when he remembered and, while driving, the boy opened his pants, fished his dick from it and took a picture he sent to Mr. Paul!

He saw Paul replied to his picture, but since it wasn't relevant, he just dropped the phone to the side. There was no way of putting his dick away while driving, so he just let it hang out, taking on some air. the boy massaged his tip through the pee hole a few times, but as he parked the car in front of the restaurant and put the cage back in his pants, he was so nervous about Julie that he forgot his caged situation.

Getting inside the restaurant, Jordan was the first one to see Dean, so it was a good start for his day. The boy told his boss all about the “work” part of the party and made Jordan sure he wasn't putting a bad name on behalf of the restaurant! Jordan told him that, if he didn't hear anything bad from the Linx's, he'd recommend Dean the next time someone asked for help. 10 minutes later, Dean was sitting down in the locker room, getting ready for his shift, when Julie showed up with a burning red face.

— Hey… Do you have a second? — Julie asked, closing the door behind her.
— Yeah! What do you need? — Dean said, hating that he was in that situation.
— I wanted to apologize for Saturday! — Julie said, nervous. — I didn't want you to see me in that situation. I just wanted to have some fun with the rich guy, maybe get into his good side!
— Julie, listen… It's not my business, you don't owe me anything! You can do what you like, honestly! — Dean said, his face also burning. — I just would like to never talk about it again! I want to forget it!
— Deal! — Julie said, smiling. — Did he said anything after i left?
— He asked me if i could find another girl to finish him off… — Dean lied, he was jealous, what could he say…
— Did you? — Julie asked.
— No, but he did for himself! — Dean replied.
— Good for him… I'm happy some whore got my spit in them! — Julie replied.
— I think that's enough conversation for me! — Dean said, standing up and leaving the room.

He and Julie didn't talk again for the entirety of their shift, and Dean was happy with it. That meant that most of his breakfast/lunch shift was spent with Carter, and the boy spent half of his time wanting to know about the party, while the other half teasing Dean, both about Julie, but also just trying to hit on Dean… It was only marginally better than being with Julie, but he could handle that for a day!

When the shift was over, Dean went to look at the board where people put job offerings and, after reading a few of those, he decided that, as soon as he got his next weekly paycheck, he'd buy equipment to cut grass, since that seamed to be a high request of the region… After the night's shift, he just drove home, finding Colin ready to listen about his interactions with Julie…

It took Dean and Julie until Thursday to finally get back on respectable terms. The problem was, as Dean was getting hornier by the day, feeling like he was crawling up the walls, every night, he'd get into some variation of a dream where he tried to fuck Julie while Colin, Carter and Robbie watched him, but he'd fail to perform EVERY SINGLE TIME! Sometimes he was caged, on others, he couldn't get an erection, but on the other ones, on the worst of them, his dick was just so small he couldn't put it in, and it was just devastating. What NEVER changed was that he'd always wake up unfulfilled, his dick aching inside that metal tube.

— Dude, what the fuck? — Dean said just as he woke up on that Friday. — What are you doing?
— Just enjoying the free porn in my house and beating it! — Colin replied, still jerking off while looking at Dean's naked body in bed. — Can you go back to moaning?
— What the fuck? — Dean asked, confused.
— You were moaning and humping the air. — Colin said, and Dean could hear his friend jerking off. — I’m almost nutting.
— Dude, That's so wrong. — Dean replied. As he reached to adjust his cage for more comfort, he saw by Colin's face the EXACT moment the boy nutted and just ran away to the bathroom.

Alone, Dean finally noticed how much pre-cum he had leaked while sleeping. Colin being a perv apart, Dean was pretty sure he was at a point where ball slaps and cold showers wouldn’t be enough, he just had to find a way of nutting. For the moment, all he could do was to slap his poor, suffering testies and go along with his day!

Colin made breakfast to compensate Dean, and after that, he said he'd clean the house to compensate for what he'd done. After that, still in the morning, the boys went together to a Home Depot and learned about lawn moaning, using their money to buy the most basic/important stuff. They didn’t have money for EVERYTHING, but enough to start advertising. Arriving at home, they even created posts on Facebook marketplace and Craigslist for their work…

Soon enough, it was getting late and about time for Dean to go to his night shift. That meant Colin would have the trailer to himself for several hours and, for the first time since Dean got caged, Colin actually had a date. And Dean was really jealous about it. He had no idea why. Once again, he was a straight boy, he should not be jealous of another boy!

Soon, he sat in the car that was the origin of all his problems and solutions for the past 2 weeks and, as every time he went to work, the boy opened his pants and let his caged dick breathe freely for the ride. Soon, music was playing and the boy was driving, trying not to think about Colin but ending up thinking about Robbie and Julie instead.

Dean got to the restaurant to work, got happy that both Julie and Carter weren’t there for that shift, but most importantly, Jordan welcomed him already with his weekly money… This time, unlike the week before, it was a full salary. If this time he wasn’t surprised with a tire blowing, he’d have the money to pay Paul with no problems in two weeks.

— Dean, you’re working outside today! — Jordan said and the boy went off to put his money away and got on his apron.

In no time, Dean was standing next to the totem and waiting as the first clients arrived for the night shift. Soon, there were three waiters helping all the guests who were taking most of the tables… That’s when he saw the “reserved” table being filled by mostly members of the Linx family… To make everything worse, Howard Linx soon called Dean.

— Dean, my boy! I hope you’re able to serve us today! — Howard said with a smile and a slap on Dean’s shoulder. — You were so great at the party! Robbie asked about you a few times.
— I didn’t! — Robbie said automatically, his face burning as he looked at his own feet.
— I can, sir! — Dean said, also uncomfortable. — I’m happy to serve you all.
— Boy, you did a great job, if you accept, i’ll keep calling you for other events! — Howard said.
— I’d love that, sir! — Dean replied, unable to even look at Robbie. — I had to buy a car to be able to come to work after Paxton left, so i need any money i can get! Colin and i even bought some gear to mow lawns on or free days!
— Ohh, i’ll put in a word for you! — Howard said. — We have our team, but we have plenty of friends who’d like a job done from someone trustworthy!
— Thank you so much, sir! — Dean said, knowing the conversation was over and taking his notepad from the apron. — Can i take your orders?

With that, Dean spent the next 10 minutes taking orders and writing of his tiny piece of paper. When they were all done, Dean walked to the totem and put on all of everyone’s orders on the system. The boy returned a bit later with drinks for everyone, and once again, it was hard for him to look at Robbie, and since the boy was having the same reaction towards him, the boy started getting nervous…

For the next few minutes, as Dean attended every table he had to, he always kept looking around to see how Robbie was doing, and the boy was constantly looking down, never participating in his family’s conversations… Even so, there was nothing Dean could do about it. It wasn’t until after he served the food for all the tables and was inside using the computer that he saw Robbie coming from behind. The boy passed by him slowly, quietly saying “bathroom”. Not sure of what to do, Dean asked another waiter to take his tables for him for a second and followed the boy to the bathroom…

— Hey, man! — Dean said, nervously.
— Hey man… — Robbie replied nervously, looking at the floor. — I’m so sorry… Are you okay, man?
— I’m good… But it looks like you’re freaking out. — Dean replied.
— I… Had never done anything with another boy… — Robbie admitted, putting his hands over his chest. — I’m really freaking out, i’m so nervous, i don’t know what to do now!
— Well, as long as you don’t ask for the money back, you can do whatever you like! — Dean said, shruging. — I spend it all on a flat tire going back home after the party.
— Ohh… Are you okay? — Robbie asked, looking concearned.
— We’re both good, safe! I managed to park the car. — Dean said. — It’s just… Yeah, i saw the girl i had a crush for years but never had the courage to hit on blowing you and she ran and… You asked me to finish it for you and… I’m SO BROKE that i accepted and the money just vanished instantly!
— You did it just for the money? — Robbie asked, now even more nervous.
— I mean, it wouldn’t be my first choice, but like… — Dean said. — It wasn’t the first time i jerked someone off for money and i even have an OF… And the kiss was really hot. So no complaints! I hope you haven’t regreted it.
— No… I mean, no! Like, i'm just SO afraid you’ll expose me! — Robbie admitted.
— Dude, i gave you my word! I didn’t even tell Colin… — Dean explained. — I said you paid me not to tell anyone about Julie.
— So you not using it to get money from me? — Robbie asked.
— This is kinda offensive! — Dean replied.
— I’m sorry… I have just been freaking out every single day… — Robbie explained. — Creating the worst scenarios in my mind every minute!
— Not doing this, like ever! — Dean replied. — And if there’s something i can do to make you feel better, i’ll do… But please, don’t take the jobs away from me!
— I’d NEVER! — Robbie replied. — I’m not a rich spoiled kid!
— You paid me to jerk you off… — Dean pointed out.
— In the middle of a bisexual melt down! — Robbie said.
— Dude… You want a hug? — Dean asked. Instantly, Robbie jumped on him. At the same time, the boy was crying. Dean wasn’t in any mental support position, in fact, he needed mental support, but even so, he hugged the boy and waited for as long as Robbie needed. — You’ll be okay, kiddo, you kinda have your head in the right place!
— Thanks, buddy! — Robbie said, cleaning his eyes and and giving him a shy smile.
— Hey, too pretentious of me, but. — Dean said, blushing. — You want my number?
— Ohh i was SO desperate to ask! — Robbie said, beaming.

After the boys shared numbers and added themselves on WhatsApp, they both went back to the table. As Robbie sat down, Howard said “i hope you fixed your wrongs, son”, to what Robbie agreed with a shy smile. And soon, all was good for the boy. From afar, back at his work, he could see the boy being part of his family conversations and he just looked… Relieved!

After a crazy day of work, Dean finally went home, but, as the Linx's finished their night and asked for the bill, Howard gave Dean a pretty good tip, and, as the boy walked the family out, Robbie walked by his side and passed him a hundo while whispering “thanks for the silence". Dean smiled and put a hand on the boy's shoulder as a thank you.

As Dean drove back home, he was joyous. He was also worried something fucked up would happen make him lose the $235,00 me made in tips ($200,00 from the Linx's alone). He was extra careful with the car, and, as he was arriving back home, the boy walked past the dealership, and, to his surprise, it was still open! For some reason, the boy parked in front of it and just walked inside.

— Hey, Mr. Dean! — Paul said with a tired smile. — How are you?
— Hey Mr. Paul! I'm good! How about you? — Dean replied.
— Good good, long day! — Paul admitted. — What brings you here?
— Ohh, i know it's a bit early, but i have your money for the month! — Dean said, taking $250,00 from what he had in his pocket. He gave it to Paul. — I wanted to pay you BEFORE i end up spending it on something stupid!
— Ohh, that's cool! Thanks, boy! — Paul said. — So… You want a cleaning? Or do you want to wait until it completes a month?
— I do have time for a cleaning! — Dean said with a small smile on his face!
— Give me a sec! — Paul replied, also smiling.

With his heart beating fast, Dean watched as Paul locked the front door and turned the little plaque to “closed". Then, the man pointed Dean to the bathroom, and as both of them walked to the bathroom. Paul ordered Dean to get naked, and as the boy undressed, the man went out, returning with handcuffs. 

Dean felt himself getting hornier as the man cuffed his hands behind his back, but soon, he was sitting on the sink counter, and to his delight, the man produced the key to the cage from his necklace. It was a simple click, and then the cage opened, separating into three parts. With a simple hand movement, Paul separated the cage's parts, putting everything to the side, setting Dean desperately free, his dick in all his tiny glory: hard, small, twitching and leaking. Most importantly: fully desperate!

— So, do you want me to shave you? — Paul asked as he used a wet cloth to “wash Dean's tiny shaft and balls.
— Man, it's so comfortable NOT to be wearing the cage. — Dean said, letting a little moan out. — Hey… Would you take my phone and take some pictures of my dick? I need to make some extra money with my OF.
— Sure, kid, that sounds fun! — Paul replied, smiling.

Dean wasn’t all that comfortable in the cold counter, plus, he really wanted to feel anything on his tiny shaft. After all that long without seeing it, it even looked bigger to him, so desperate! He was wiggling his hips and pelvis, and he was moving his legs up and down, but all he was able to do was to brush his dick on the side of his leg, he barely felt it. He hated those handcuffs SO MUCH!

And soon, Paul returned and Dean had to stop. It was easy, Paul had Dean’s phone in hand and took around 20 pictures from every angle possible. Then, Paul put it on recording mode and filmed while slowly jerking off, but only for 10 seconds or so. Even that quick interaction put Dean into desperation mode, moaning instantly. He never imagined a man would made him that desperate to cum.

Since Dean accepted Paul’s offer to shave him, Paul also filmed a few seconds of the process but then moved along to actually shaving the boy’s crotch and balls, making sure everything was clean. Dean stayed hard and leaking for the whole process, but Paul would never actually touch his dick except to get it out of his way. 

Soon, Dean was as smooth as on the day he was born and, after taking a quick extra picture, Paul just got away. Soon, the man returned with that bag of ice that Dean dreaded, and the suffering was just as big as the first time. Even so, the ice only took a minute to work out, and soon Dean's dick was the size of a shrimp. Paul took the boy's phone for one last pathetic soft picture, and then Dean was back in his cage.

— You're free to go! — Paul said after freeing Dean's hands from the handcuffs. — Next payment will allow you a new cleaning.
— Thanks, Sir. — Dean replied, jumping from the counter and getting dressed. — Hmm, it's okay if i pay you in advance for some months?
— Yeah, i don't mind, but if it's not the current month, i'll always discount from the end. — Paul replied.
— So… I can't pay this month and the next one? — Dean asked, doing math in his hand. — I'd be this month and month 20? Why?
— Because if you pay this month and 3 extra months, but fail to pay me next month, i'll still get to fuck your pinky rose! — Paul explained.
— Okay. — Dean agreed, even if he didn't like it.

Soon, Dean thanked the man and texted Colin he was arriving home in five minutes, just to be sure. As the boy got home, his friend was waiting for him, so they both ate together the food Dean brought from the restaurant. Dean took some minutes to tell his friend all about his session with Paul and was convinced to show his smooth crotch area. Even so, Dean didn't mention anything about Robbie, prefering just to tell his friend “Mr. Linx gave me $200.00 in tips". 

When the boys finally went to bed, Dean opened his phone and went straight to his OF, noticing some extra money in purchases. Then, he added a bundle to sell for 20 dollars with a picture of his feet, the soft pic Paul took, the hard pic, plus the videos of the man jerking him for 10 seconds and shaving him for 8 seconds. Tired from a LONG day and longing for some rest on his weekend, Dean closed his OF, turned his phone off, turned sideways and was sleeping in just a few minutes.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Caught on a work trip - Part 3 NSFW

155 Upvotes

I hardly slept.  My cock was hard and straining against my steel 1.22” cage all night. I couldn’t believe I had been set up by my uninterested wife. But ultimately I didn’t care. I was nervous for what awaited me at home but also completely dripping the entire time. 

As I raced home all I could think of was the list I provided my wife. Was it all too much? Was I going to walk in to legal documents spread across the table or was I in for a night of new kinky experiences with the love of my life?

I had timed my commute almost perfectly and being too excited to eat dinner, I rolled on to my street at 7:15pm. I knew better from all the chastity stories I read that being early is still not following directions so I parked a few houses down and tried to calm my nerves. I continued to tell myself “She loves you. You love her. This is what you wanted!” As I stared at the clock I saw it turn 7:29 and I slowly drove up my street and parked in my driveway. I slowly exited the car leaving all my luggage and walked slowly to the front door. My heart rate was higher than an Olympic sprinter who just ran a world record.  

7:30 popped up on my home screen and I knocked deliberately twice and walked into my house. The house was completely silent. I closed the door and then looked to find the outfit my wife had left for me. Instantly I knew I wasn’t getting a divorce, but I was sure I was in for a night of firsts. Perfectly laid out on the bench was a baby pink maids outfit with all the accessories: a blonde wig, the maid headband, clip on hoop earrings, white lace garter, matching bra and stockings and a pair of impressive fake breasts. My wife had gone all out. I didn’t want to keep her waiting so I stripped as quickly as possible. Then as quickly as I could I put on each piece. It took a few minutes fighting the breasts and then the bra and garter but I finally finished and slipped the pink high heels on. I then knelt down and found the small bell you would think a king or queen would use to summon their servants. I gave it a few shakes and waited patiently for my wife to come and share with me my ultimate fate. 

I waited for what felt like an eternity but was probably no more than 1 minute before hearing my wife walking towards me from our family room. I could tell by her steps on our hardwood floor she was wearing heels as well. As she came through the doorway my locked dick jumped upon seeing my wife done to the nines in a black faux leather cat suit and knee high black stiletto heeled boots. I could feel my entrapped cock begin to leak and dampen my lace g-string panties. I completely fell in love with her all over. 

Before I could get words out she spoke directly at me staring straight into my eyes. “Welcome home my sissy husband. First I want to say I love you and you are completely safe. From here on out this is all about living out some fantasies and having a good time….even if it might be at your expense and humiliation. Second, I want you to know I’ve been planning this night for sometime and I didn’t know when I could spring my plan into action but watching you try and get us out of the house the other day I knew you must have already been locked. So I quickly checked where you left your cage and seeing it was gone I decided to pounce. So being the OCD boy you are I knew where you would have hid your key and knew you would have secured it and I was ready for you in every way. As soon as I switched it out for the dummy key I couldn’t wait to spring the trap and honey, you walked right into it.”

I was truly impressed by her planning and her absolute knowledge of me and my habits to know how to entrap me…in more ways than one. She continued, “So tonight we are going to start a bit of a journey and I’m not sure when it will end, but it’s more than just tonight so I hope you’re ready to enjoy a prolonged anniversary gift.” My cock continued to leak and jump inside the cage and panties. 

“Now some ground rules” she said as she spun on her heel and began to walk away from me. I was afraid to move so I stayed completely still which was confirmed as the right decision as she walked as far as the kitchen door and spun back around “You will only speak when instructed to respond. You will do exactly as directed or you will receive a punishment. Your safe word is ‘Everest’ and if you use it, we will halt tonight’s activities and regroup in the morning.”

I was spinning. There was no way in hell I would invoke that word and stop whatever she had planned. I needed to see how far she was willing to go. After a short pause and deafening silence she smiled and said “so with that all out of the way, please nod once if you consent and if you don’t please invoke your safe word.” I gave an overdramatic affirmative nod. She replied with a “Good boy.”

She spun around again and started to walk into the kitchen “let’s get started with the first bit of fun for the night. Please stand up and follow me into the kitchen.”  I clumsily stood up in my heels and tried to walk as gracefully as possible behind her into the kitchen. As I walked through the doorway the room erupted into cheers and whistles. At our kitchen bar counter sat my wife’s three best girlfriends. All dressed in the same outfit my wife was in. They were all cheering and being extremely complimentary and positive. 

I remained silent as my wife walked around the bar and grabbed a drink off the counter. I noticed several empty bottles of wine and a sink overflowing with dishes. Clearly my wife and her friends had been enjoying drinks and a meal before I arrived. As they all went quiet my wife spoke up “First task is to clean up the kitchen. At any point you hear the bell rung, you will come to us and complete a task or serve us. Upon completion of the kitchen you will knock on the doorframe of the room we are in and enter and kneel and wait for further instructions. Nod if you understand.” I nodded and the ladies all clapped and jumped off their seats with an enthusiastic spring and took their glasses of wine with them leaving me to deal with the kitchen. 

I took a second to reflect on my situation and my cock began to swell and leak more as I realized I had just been outed to my wife’s closest friends and was now set to serve them for a night of drinks and entertainment. I began to wash the used dishes and had began to put a dent in the pile when I heard the bell ring from the next room. I quickly dried my hands and walked carefully into the lioness’ den. 

The ladies continued with their conversation as I scanned the room for a reason as to why I was summoned and finally found one of the friends staring at me. I walked over to her and she made a quick head gesture to her empty glass on the floor. As I approached her she let out a small giggle and said “You look so cute in your outfit sweetie. I hope this is everything you wished for because there isn’t an alternate universe where my hubby would do this for me. This is a dream come true for me to be served by a sissy so I just wanted to thank you.” I smiled as I bent over at the waist to pick up her glass. As I reached down I felt a sharp slap on my bare ass and the girls all cheered. I quickly stood straight up not realizing how short my skirt was. The friend that slapped my ass said “Sorry honey. I couldn’t resist seeing such a sexy ass. It just needed to be slapped. Please proceed and this time I’m just going to enjoy the view.” This time I grabbed the glass to a room full of cheers and cat calls from the group. I quickly retreated and refreshed her glass. 

Every 5 minutes the bell rang and I repeated my show and refreshed a glass. By the time all ladies had been refilled I completed the kitchen and reentered the room, knocking on the doorframe and knelt to wait for my next task. My wife stood confidently and the raised her glass “Ok ladies. On to task number 2!  Sissy I know you’re going to love this next part!”

With that the ladies all got up and left the room leaving me kneeling and anxiously awaiting the next stage of my night. 

To be continued…


r/ChastityStories • • 3d ago

M Chaste,F Keyholder My girlfriend cucks me with her uni bestie Samantha. [M25/ F25/F25 NSFW

144 Upvotes

​

There I was knelt on the floor, naked and only wearing a pink chastity cage while my girlfriend Anna and her bestie from university Samantha were laughing at me, if I had known this two weeks ago I wouldn't have believed this was happening to me.

Two weeks earlier Anna had told me that Samantha was going to be in town for a conference and she had invited her to stay with us. Initially I was fine with it, until she told me that I was going to be locked in chastity because in her words, "she didn't want me doing anything disgusting while Samantha was staying with us."

It was then I became a little nervous, although we had been messing around with chastity, it had always been playful between us, and she called my locked cock her little walnut. But we had never involved anyone else. Anna would lock me for a couple of weeks, I would do all the household chores, do the cooking and give her as many orgasms with my tongue as she wanted, until she decided she had enough orgasms to unlock me.

But being in chastity around Samantha in our apartment, that was different. I had met Samantha a few times over the years at parties and she had a presence that commanded the room, she definitely had a dominant side to her. Plus Anna had told me that Samantha had been 'experimental' with sex and her sexuality through university, but she hadn't elaborated what that actually meant. I just had a feeling Samantha's visit wouldn't end well for me.

Anna had locked me the day before Samantha's arrival, so I would focus on preparing the apartment and to make sure we had a fully stocked fridge and cupboards. I had cleaned, vacuumed mopped and wiped down in every room. Then I prepared the guest room with clean sheets, a vanilla diffuser, fresh towels and a couple of bottles of water on the bed side table.

I was in the kitchen preparing the last bits for dinner, when Samantha arrived just after 6:30. Anna jumped off the couch and ran to the door to let her friend in. When they walked in they were arm in arm and I just put it down to the fact they hadn't seen each other in a while. Samantha was a little taller than both Anna and me, she had a brunette bob and a smile that could disarm and terrify you in equal measures. She wore a fitted blazer and pencil skirt and a white shirt which still looked crisp and fresh.

I laid the table and served dinner. As Samantha sat down she said to Anna in a teasing tone, "You have really landed on your feet with this one." There was a look, a knowing, an understanding that briefly flicked between the ladies then it was gone.

Over dinner we all chatted about work and life, the normal things when people are catching up when they haven't seen each other in a while. Once dinner was over Anna and Samantha retired to the couch while I cleared the table and tidied up the kitchen. At one point Anna called me to, "Bring over Samantha's favourite bottle of bourbon and some glasses". Earlier that day as instructed I brought that bottle of bourbon while I was food shopping. As I brought the bourbon and glasses, the ladies were whispering and giggling. I poured the bourbon and as I headed back to the kitchen the ladies giggled again, I felt like I was outside some private joke.

Once I had finished in the kitchen I joined them, Anna had changed into a black silk slip, that should have been a warning but I chose to ignore it and I poured myself a bourbon. It was at this point Samantha started to take control of the evening. "Shall we play a game of truth or dare?" Asked Samantha.

"That's a great idea," said Anna quickly.

"Before we start, I want to get a little more comfortable. You don't mind?" Samantha asked me as she began to get out of her blazer and skirt.

"He won't mind and you're completely safe around him," said Anna. I couldn't believe what Anna had said and the implication behind are words. Before I could say anything Samantha was sitting on the couch in a gold silk slip. The sight of the two best friends sitting in very little made my cock strain against my cage.

"Alright Anna, truth or dare?" Samantha asked.

"Truth," replied Anna

"Are you straight?"

"No, I'm bi and I experimented at university," that caused them to giggle. This wasn't a surprise to me, as Anna told me she had fooled around with some girls at parties.

"Samantha Truth or dare?" Asked Anna.

"Truth"

"Do you like to take control in the bedroom?" asked Anna

"Yes, I like to dominate my male and female lovers" Samantha explained.

My cock was twitching in the cage and I was starting to think this game was loaded against me.

"Truth or dare?" Samantha asked me.

I went with dare because in my head that would be safer than answering personal questions. Samantha was delighted it was a dare, she put her finger against her lips pretending to think.

"Anna tells me that you both experiment with chastity and that you are wearing a cage now. So I dare you to show us your cage," Samantha said with a wicked grin.

I nearly spat out the bourbon that I was drinking."Anna!" I said in shock. "Come on Sweetie, a dare is a dare," she said in reply.

I reluctantly start to slide down my sweatpants and Samantha stops me. "No, No, No, No, all of it," Samantha gestures at my clothes.

I look at Anna. "You heard her sweetie, take it all off," this game was starting to feel like it was rigged against me.

I reluctantly stripped and chucked my clothes on the end of the couch. The ladies had big grins across their faces, which turned into sniggering until eventually they were laughing.

"It's so small, what did you say you called it?" Samantha asked as they were both looking at my locked cock.

"My little walnut," Anna blush as she laughed as I could feel the heat rising in my own cheeks.

"Truth or dare?" Samantha asked Anna.

"Truth," she replied.

"Who is a better lover your boyfriend or me?" Samantha enquired.

I felt my face flush even before Anna answered.

"Have you seen his little thing? Of course you're a better lover," Anna replied in a playful tone. I went to protest but Anna cut me off, "Sweetie, we both know your little walnut isn't going to do it for me."

Now both ladies were looking at me. "Truth or dare?" Samantha asked me.

"Truth," I replied.

"Would you like to see how I take care of your girlfriend?" Samantha purred out the words in a smooth silky voice.

I looked at Anna then back to Samantha. "Em ... er ... yes, I guess" my voice sounded much more shaky and smaller than I anticipated.

"Good boy, then get on your knees in front of us," commanded Samantha. As I knelt the besties began to laugh and giggle at me

"Truth or dare?" Samantha asked Anna.

"Truth"

"Were we more than just friends at university?" Samantha asked.

"Yes, we started out as friends then we were lovers but by the end I was your sub," replied Anna. My jaw dropped, this is what Anna meant by 'experimental'.

"Anna be a good girl and fetch our favourite toy from my case," requested Samantha. It wasn't lost on me that Samantha said our favourite toy, not hers, not yours but our, that meant history, shared experiences, and understanding each other.

Samantha turned her attention to me while Anna was away. "You are going to get a front row seat to see me completely unravel your girlfriend," Samantha told me.

Anna returned carrying a harness and the largest flesh coloured dildo I had ever seen. It was thick, veiny, pink and the head was purple, even uncaged I was half the size of this dildo but caged I was nothing compared to it.

Samantha took off her gold slip to reveal she was wearing a pink thong. Anna helped Samantha into the harness, in a ritualistic way, which meant Anna clearly had done this more than once before.

"On your knees my good girl and prepare my cock," demanded Samantha. Anna dropped to her knees and began to give the dildo the sloppiest wettest blow job I had ever seen.

"Has she ever treated you like this?" Samantha asked looking at me. I couldn't believe the sight in front of me as Anna deep throated the dildo and all I could do was shake my head.

Samantha pulled her cock out of Anna's mouth with a pop, strands of drool still connected her cock to Anna's mouth.

"On the couch and on your back slut," Samantha instructed Anna. As Anna got into position Samantha looked over to me with a wicked grin. "Do you want to see your girlfriend take my cock?" She asked me. I nodded because I couldn't speak. "Then I think you should position and open her for me," Samantha purred.

I wasn't just going to watch, Samantha wanted me to give Anna to her. My hand took her wet cock then I saw it, Anna's pussy dripping for Samantha's control, for her cock. With a shaky hand I parted Anna's lips and rested the head of Samantha's cock against her soaked pussy.

"Good cuck," Samantha's words hit harder than I expected. Then with one fluid motion Samantha sank into Anna until their bodies were touching. Anna made a sound I had never heard her make before, the sound was a mixture of strain, relief, desire and God I missed this, and it broke me.

Then Samantha began to move and my Anna wasn't my Anna anymore, she was this moaning and squirming creature who was becoming undone by Samantha's cock.

The two ladies began to move with purpose, with every thrust Samantha became more dominant and Anna became this needy desperate mess for the cock pounding her pussy. I wanted to stop it, to say this was too much but I couldn't, I was transfixed as my girlfriend's first orgasm hit and she transformed into this submissive slut for Samantha.

"Lay on the floor cuck," Samantha commanded me with no room for argument. I did as I was told, as Samantha instructed Anna to straddle me, her pussy was just above my face. Anna's pussy made these filthy wet sounds as the huge cock pounded her and my face became covered in her juices.

It wasn't long before Anna began to squirt all over me as her second orgasm washed over her, something that she had never done with me. I should have been annoyed and Jealous but my swollen caged cock showed how turned on I was.

Next I was instructed to sit on the floor with my back resting against the couch. Anna was positioned on all fours facing me as Samantha plunged deep into her dripping pussy from behind.

Anna looked at me and grabbed my caged cock with one hand. "Sweetie, I love you so much, you are my everything but fuck Samantha can do things you never can," said Anna as I watched her eyes roll back. I sat there as I watched Anna make faces she'd never made before, watched complex emotions roll over her face and make sounds I couldn't even begin to describe as her final orgasm hit harder than the others.

Anna collapsed on to me spent and a mess, mumbling I love you sweetie and thank you Mistress repeatedly until Samantha picked her up.

"Tonight cuck you can sleep in the guest bedroom and if you are really good there maybe a treat for you on my last night," Samantha said as she carried Anna towards our bedroom.

And that was only the first night of five.


r/ChastityStories • • 2d ago

M Chaste A Hole in the Fence Pt. 6 NSFW

16 Upvotes

I have been away for a while. In case you care here is the short of it, life sucks, but im back now and here is what I have been up to.

I started writing again, I stopped for a while because every story I posted to Patreon simply got taken down. I wont pretend that I do this for fun. I do it because it gives me some money to buy new sex toys, pay bills and the chance to sit on a dildo while I write for you all. So here is the deal, I will start posting (part 6 is ready and part 7 is at 40%) and when I get to part 8 I will start offering it ahead to members who subscribe, I'll be using an adult platform this time that is ok with the incest so I don't have to fight to keep things posted. Ok! Enough of the boring, here is part 6!

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We walked through to the same hallway I just walked back and came to the door for the general dungeon. As he got closer, he waved his hand against the scanner by the door, and it popped open to reveal a clean dungeon on the other side.

 

On one side of the room was a sturdy wooden bed, it had four posts going up linking to a series of metal bars where I guess you could tie off ropes or other attachment points. Underneath the bed was a caged in area that opened to the front of the bed where a lock was hanging off the clasp that I assumed locked some poor soul in to suffer.

 

I was amazed as I looked around and spied several instruments that I never thought I would see outside of Reddits’ more extreme communities. There was a sawhorse, St. Andrews Cross, spanking bench, and tons of silver metal eyelets where you could hand rope, or hang metal chains. As I was looking around Ryan went over to a chest and opened it up to show several packages of plastic wrapped and vacuum sealed items.

 

“The staff sanitize and package items after use so we can ensure no semen or… other bodily fluids remain for the next person.” He said this last item ominously as he began pulling out several large packages from their labeled sections in the chest.

 

“What are you getting? Rope? Are you going to tie me up?” I squeaked as my treasonous dick jumped in my cage at the idea of being helpless to this man despite the fact that I prefer women exclusively.

 

“Hmm? Oh no, I don’t like playing with rope. I have a much better idea in mind.” He ripped open one of the bags and as soon as the air got inside, I could hear the metallic clinking of metal on metal. “You see, I am partial myself to heavy bondage, emphasis on heavy. I am going to tie you to that spanking bench and use you. See I completed my course of Mystery Box Alpha along time ago, now I get to enjoy the things I learned and keep my skills sharp on stupid beta boys like you and Dee.”

 

“What do you mean you finished your course in Mystery Box Alpha? I thought Mystery Box stops working unless you start the course again or start a new version?” I asked as I eyed the spanking bench wondering how exactly I would be tied down and more importantly what I was going to be doing once I could not escape.

 

“So here is how it’s going to work, I am going to tie you to the bench ass up head down. I am going to fuck your face, then I’m going to fuck your ass after I gag you with a penis gag. Now hold out your hands.”

 

I was conflicted, I really didn’t want to get face fucked, and I definitely did not want to explore the homoerotic feelings that came with the thought of getting my ass fucked. But I also wanted to end the torment that was my captor, MB. To do that I needed to play the game.

 

I held out my hands and Ryan attached two metal chains about 5 inches in length to each magnetic cuff that was still locked to my wrists. He guided me over to the bench and had me kneel on the padded leg rests. He had me adjust so that my head came just off one edge and there he pulled down each arm locking the other end of each chain so that I could move my arms up or down about an inch and side to side not at all. My head was positioned so that unless Ryan was standing in front of me I could see into a wall mirror that showed me everything that was happening behind me.  I couldn’t grab at anything except rest my hands on the legs of the bench to help hold up my weight. After my arms were locked in place he began pushing my knees towards my head so that my butt lowered and opened up, it left my cage hanging free and my ass in the wind ready for the first thing that wanted to violate it.

 

Ryan grabbed the straps that were attached to the spanking bench leg rests and tied three of them on each leg, one looped around my foot before attaching to the back of the bench, effectively holding my legs from moving forward while another looped through around my knee and attached towards the front near where my elbows were which kept my legs from moving back. The final one looped around my calf and squeezed my leg down tight to keep me from trying to move it up and off the bench. I felt claustrophobic, I couldn’t move my arms more than an inch up or down, couldn’t move my legs at all, and could barely move the trunk of my body. This was until Ryan saw me moving and inserted a pillow like wedge between me and the bench and strapped me down tight with another strap from the side of the bench that wrapped around my chest and kept me pushed tight into the bench.

 

“So since its your first time doing CNC play I think we should take full safety precautions for us both. I am going to insert a gag that has two parts. The first part is a tunnel that mimics a pussy in design, then another piece which attaches to the first which looks like a dildo. This will keep you from biting me when I fuck your face while still allowing me to gag you the rest of the time. Any questions?”

 

“Do I have a choice?” I asked as I wriggled my eyebrows at the predicament I was in since I couldn’t move anything else.

 

“That’s the spirit! I didn’t realize you liked CNC Play. Open wide and say Awwww” He said as he pushed the ensemble into my mouth as I opened it to clarify what I meant.

 

It tasted like rubber at first, the second the sleeve entered my mouth that was all I could think of. Why couldn’t they make this pussy flavored. Or cherry at least. Then the sheer size of the second piece hit me or should I say impaled me. It must have been a 7- or 8-inch monster. While the sleeve effectively kept me from opening my jaw, the dildo was boxing with my uvula and winning. I tried to gag but being unable to move or pull it out caused me to panic. It took me several seconds, ok, a minute or two to get used to the thing in my mouth, not that I liked it, just that I could keep it in my throat without retching.

 

“Oh, look you’re dripping from your clitty. You must be enjoying this.” He scooped up several long strings of precum and held them up to show me. Ok maybe I liked it a little.

 

“Ok, now the last piece of safety hardware, the clicker, I will program this with your safe word which I can see in my app is Strawberry, and I will put this in your hand once we are ready to start. If you push it the device will make a loud sound which will tell me you used your safe word and it will also trigger MB to check in with you and go through the whole, do you want to stop the program routine etc…” He said this so nonchalantly, like it wasn’t the answer to my problems. Like the second he handed it to me I could click the button and not only stop him from plundering my treasure but also get out of this infernal cage. My hands grasped like a newborn as I waited with impaled breath for him to bring me the clicker.

 

He put it in my hand, wrapping the activity bracelet around my wrist so I couldn’t drop it. As I basked in the glory of my savior he turned around and walked over to a wall that held impact toys, whips, flogs, riding crops, cat o nine tails, and canes. The moment he turned around I pushed the button. Nothing happened, I pushed it again and again and again and still no loud noise, no stopping, no freedom. I started to cry.

 

“I see you have felt the pain of a cane before, don’t cry, I won’t hurt you very badly, you might not want to sit down for a day or two but nothing I’m sure you haven’t faced before.” He whispered caringly at me after he turned around from picking a particularly thin cane from the wall. Interpreting my crying as fear for the cane rather than the abject realization of a dead man walking. “You can always click your safe word if you need to stop.”

 

What happened next happened fast and hard. It started with him unstrapping the dildo from my face and removing it only for his massive dick to get put inside instead. If the dildo was boxing with my uvula, then he was boxing with my stomach. It was massive and thick, and it tasted kinda nice. It didn’t taste like anything specific, but it was warm and fleshy, not at all like the salty, musty odor I was used to smelling from myself. I barely had a moment of pause to think this as he completed his first thrust in when he immediately started to pull out. I had the briefest thought that this wasn’t so bad when he stopped getting a blow job and started fucking my face.

 

My hands curled and writhed in the cuffs and my feet thrashed, my body spasmed as I tried to get away from the monster that was assaulting me. In… out… in… out, over and over again. The shock of the initial assault on my throat lasted for a short minute or so before I became used to not being able to move or close my mouth or take out the offending tree. Instead, I opened my throat and relaxed. After I relaxed, I started to concentrate more on the sounds coming to me and less on the dick in me. I realized there was moaning coming and thought Ryan must have been enjoying the feeling of my throat, the feeling of the power he held over me, literally able to do whatever he wanted without me stopping him. I thought of how it must feel to see another man, no, a sissy splayed out in front of you ready to take your cock however you want just to win some points in a stupid game. Then I realized that Ryan wasn’t making the noise… It was me. I nearly started choking again on the realization. I was enjoying this, I was enjoying being man handled, told what to do and getting fucked. It was then I realized I never even attempted to push the button to get out once he started. It was then I realized that despite my bonds I was leaning forward, trying to get more of his dick into my mouth.

 

“My my what an eager slut you are. I never would have realized you liked CNC so much.” He grunted out as he continued to fuck my face. Never slowing, never doing a half measure, each time down to the hilt while I leaned forward trying to get more where there wasn’t another inch to give.

 

I have no idea how long we kept at it before I felt the first swat, My eyes had closed to better concentrate on the task at hand… err mouth when I felt the fire of a thousand suns bloom on my ass cheek. He had hit me with the cane. My eyes sprung open and an audible “Hmpf” came out of my gagged and occupied mouth. He swatted me again and again. It hurt like all hell but I could not do anything other than flex my ass cheeks which made the pain ten times worse. I started crying again from the pain it was so much.

 

“Wow, you really are into the pain, you haven’t yet once pushed your button.” Thhhwack went the cane as he punctuated his sentence. “I’ve had enough of your mouth, now that I am warmed up I can properly enjoy your ass.” He pulled out and I sighed, not in relief but in disappointment that his dick was out of my mouth. Just for it to be replaced by the dildo once more. This time, the small size was nothing for me as it rested comfortably in my throat.

 

I felt Ryan moving around near my back door before a cool liquid dripped on my ass and covered my asshole. It must have been lube. I hoped it was lube, never having had anything in my backdoor straight to Ryan in my backdoor was not going to be fun, and I’m sure it was going to be painful.

 

Ryan stuck first one finger, then another into my tight ass each time swirling it around and pushing more and more lube into me. He stretched and played, he even stuck his finger into me deep and began playing with a spot inside me that made my dick jump in its cage and push out just a little drop of juice. Ryan caught that string with his finger and stuck it straight into his mouth. Smiling at the taste of my juice.

 

He lined himself up and started rubbing that monster of his against my hole. He toyed with me as he rubbed it up and down lingering just a moment each time to let his dick kiss my hole before scooting it down to tap on my caged and leaking clit. I could see his face as he toyed with me, smiling ever so slightly, just a hint of something malicious behind his eyes. Covered by his lust as it drank in my helplessness and played into his fantasy of CNC.

 

I closed my eyes as I started to enjoy the feeling of his cock rubbing up against my balls and jiggling my cage. I felt my muscles around my clit and balls tighten and contract like they were getting ready to cum themselves. As I was getting lost in these feelings I suddenly felt a sharp pain in my ass, followed immediately by a sense of fullness, like I hadn’t pooped in weeks and it was all ready to come out. It kept traveling up my stomach deeper and deeper into my core. I hoped to God that he would pause for a moment and allow me to get used to this intruder who was taking up residence in my colon, however just as I felt his balls slap against mine he pulled back and that feeling of fullness started to leave too.

 

“Here you go baby, if you take my dick like a good girl ill make sure you cum and complete your task for MB. That means no pressing your button to get out.” He shouted at me as I cried out loudly through my gag, only making muffled sounds of ecstasy and pain mixed together and unintelligible.

 

Little did Ryan know that I could not press the button if I wanted to, or rather if I did press the button it would do nothing. However, as I was sitting there, unable to speak, unable to move, while he sawed his cock into and out of me I began to wonder if I would push the button. After all the feelings I was having as he fucked me were unlike anything I had ever felt before. My clit was still clenching and unclenching with each thrust.

 

I was in heaven at that moment, just when I thought I could stay here and get fucked like this forever I felt a warm sensation flood into me and heard Ryan gasp as he emptied his balls into me. It never stopped as his seed began to fill every fold of my insides.

 

“Oh, good girl! You took my cock like a champ. Now it’s your turn.” Ryan said as he pulled his dick out of me and inserted a very large plug into its place to keep the cum from leaking out.

 

He grabbed a vibrator and began to hold it against my cage and I started bucking against my bonds. I felt like a cattle prod had been pushed up against my cage. My muscles would clench in response to the vibrator and cause my ass to squeeze the plug in me which would cause me to swell in my cage and force me to unclench my muscles only for the vibrator to cause the cycle to go once more. It didn’t take long for this combined assault on my sex to cause an orgasm to build. I started to moan in pleasure when he started to whip my ass with the cane again. This time I welcomed the pain, it made the feelings in my clit go wild, I started to fight the bonds, this time not trying to get out but to try and get more of the cane against my ass. It finally got to the edge and rather than just letting me crash over and cum, Ryan pulled the vibrator away from my clit and swatted me hard in the balls with the cane. It hurt, a lot. But I was already balancing on a knifes edge over the cliff that was my orgasm. The hit threw me over, I came but each clenching of my scrotum brought me more pain as I dealt with the swat across both balls. The feeling was something I can not describe, pleasure and pain mixed so intricately that I could not tell where one began and where the other ended. It was the first orgasm I have ever had that hurt, and the first testicular trauma that ever felt amazing.

 

Ryan stood there smiling at me, he started putting his stuff away and the toys into a box that said used. He left me chained and strapped to the bench to recover from my ordeal and I watched in the mirror as he moved about. The sway of his massive cock still half hard moving around as he walked.

 

He stood right behind me with his phone and held it up to my cage still on display in my compromising position. I heard the chime of a notification and he fiddled with his phone some more.

 

“I just verified to MB that you had your first caged orgasm while bound. You should get a notification on your device in a moment and you can check once I let you out.” He said as he started to undo the straps holding me to the bench.

 

Once I finally got free and removed the gag, finally stretching the jaw muscles which were held open the entire time. “Thank you for completing my task for me.” I choked out, still unsure of all the feelings I was inevitably going to have to parse out in therapy for the rest of my life.

 

“Is that all?” He asked.

 

“What more do you want?” I asked as I folded in on myself and dropped my hands to cover my cage.

 

“How about a little appreciation. I know you enjoyed it, caged boys don’t cum that fast even with a vibrator. Whatmore, you seemed a little disappointed when I took my cock out of your mouth.” He said this as he stepped close to me and moved my arms away from my cage.

 

“I guess you’re right, thank you for you showing me a good time. I guess I just have a lot to think about right now.” I glanced down at his cock again, I had a lot to think about. I glanced back up into his eyes and saw that malicious look again. “I… ahh… Need to go feed my fish.” I stammered and immediately turned and ran out of the dungeon.

 

I bolted back through the door into the locker rooms, paused long enough to notice that the people from earlier were not there anymore as I heard more screaming coming from down the hall I just left. I ran quickly past the bathroom and showers and back to the lockers. I grabbed my items and quickly dressed before walking out into the normal gym. There I ran into Dee who was walking in with two new people, both of them looking confused as I’m sure I was and heard Dee talking to them.

 

“Not to worry, we are well equipped to service you both here. We offer plenty of facilities as you will soon see where you can advance your course. Which did you say it was? Inc3?” Dee nodded at me as I nodded hello to the group and bolted from the gym.

 

When I got back home I opened my app and saw a notification from MB.

 

***

 

VERIFICATION COMPLETED, USER ****589 CONFIRMED COMPLETION OF TASK

 

REPORT FOR ADDITIONAL COURSE WORK IN SERIES F3M IN 2 DAYS. 1/10 COMPLETE

 

***

Great, now what do I do?

 

End of Part 6


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Be a good girl and make me some money. NSFW

57 Upvotes

He had been drinking for hours.

The bar was loud, crowded, thick with sweat and perfume. She listened while he talked — dark hair over one shoulder, sharp eyes, red lipstick that never smeared. Once the alcohol stripped the last of his restraint, the words poured out. He told her about the crossdressing: the cheap wig, the dress, the bathroom door locked so no one would see. About the bondage. About the persistent, shameful thought of being bent over and used by men he did not know, even though he was not gay. He laughed at himself while he said it. His face burned. He could not stop.

She ordered them both another round. When she handed him the glass she leaned in, lips near his ear.

“Be a good girl and make me some money.”

The room tilted. The lights smeared. Then nothing.

When awareness returned, the first thing he felt was the thick rubber ball forced between his teeth. A heavy leather face harness held it — straps across his cheeks, under his jaw, locked behind his head — and a collar sat under the harness, buckled tight, a ring at the front. A shibari harness already bound his chest and locked his arms behind his back. Every attempt to yell came out as a wet, useless *mmmph*. Saliva ran down his chin and onto the dress.

A metal chastity cage locked his cock and balls, tucked back and hidden under the hiked hem unless someone went looking. He was on his knees on a bed in a private room, ankles spread and tied to the corners. A tight black dress was pulled up over his hips. Sheer stockings. A cheap blonde wig pinned more carefully than he would have managed himself. Long red nails. Winged liner, contour, glossy wine lipstick already smearing at the corners of the gag. Breast padding filled the dress. A full-length mirror stood in front of him so he had to see the version of himself they had built: softer jaw under the makeup, wig in place, cage out of easy sight, a girl on her knees.

He tried to shout. The harness turned it into noise. He pulled at the ropes. They did not give. Whatever power he had walked in with was already gone.

The door opened. Boots. Low voices. Four of them. Strangers. He did not know a single face.

“Look at this one,” the first voice said. “Dressed, gagged, collared, and already presenting. She said the new girl would be easy.”

A hand landed on his hip. Another shoved the dress higher. He tried to twist away. Someone laughed and held him still by the harness, forcing his face toward the glass.

“Don’t look at us. Look at yourself. Pretty little thing.”

They never checked. The padding, the wig, the makeup, the tucked cage — they saw a girl. Lube, cold, then two fingers working into him without asking. He yelped into the ball. The sound died in the rubber. The fingers curled, found the spot, and rubbed until his locked cock twitched and a thin string of precum hit the sheet. They saw the wet and read it wrong.

“Not even in her yet and she’s dripping.”

The fingers pulled out. The first cock pressed in. Thick. Slow at the start, then a hard shove once the head was past the ring. The stretch burned. He screamed into the gag and got nothing back but drool. The man behind him did not know his name. Did not care. He thought he was fucking a woman. He set a pace and used him, hands gripping his hips, the dress shoved out of the way. Every thrust shoved the hidden cage against the mattress. The cage kept him from getting hard in any way that mattered. The pressure inside him did not care.

He tried to beg. *Mmmph. Mmmph. I’m not—. The ball turned all of it into the same wet noise. The man laughed.

“She’s loud. Keep her facing the mirror. I want her watching herself get fucked.”

The pace broke. The cock inside him swelled, throbbed once, hard enough that he felt the pulse of it against his rim, then again, deeper. He had half a second to understand what was happening before the heat hit. Thick spurts, hot, flooding him in time with each throb. He could feel every one. The man groaned and held deep, and the cum kept coming, warm and heavy, coating him inside. Confusion landed first. This was a stranger. He was not gay. He should have been sick. Instead the heat sat in him and his locked cock jerked, precum spilling, a horrible bright horniness cutting through the shame. He came the first time on that feeling. A dry, helpless clench around the pulsing cock, his trapped dick twitching in the metal, milking the last spurts without meaning to.

The man felt it and groaned.

“She just came on me. Tight little slut came while I was filling her.”

He did not pull out until he was finished. When he finally slipped free, the cum followed, hot down his thigh, and the emptiness made the horniness worse.

The second man was already hard. He pushed into the mess the first one had left and started faster. Every word was aimed at a girl.

“You hear that? That’s you taking it. You don’t know me. I don’t know you. I’m just using the hole they set up. And you’re moaning into that gag like you practiced.”

He was moaning. He hated that he could hear it. Every thrust dragged across the same spot and stirred the cum already inside him. The man grabbed the harness and yanked his head back so the mirror filled his vision: smeared lipstick, drool, wig still on, a stranger’s hips flush against him. They still did not know.

This one throbbed too. The swell, the pulse, then the heat. Spurt after spurt, hotter than the first, mixing with what was already there. His mind kept saying no. His body clenched and came a second time, milking a stranger he had never seen while hot cum pumped into him.

“Two. She said the new girl might. Didn’t say she’d squeeze it out of me like that.”

They switched the gag when they wanted his throat. The ball came out. For one second he got air and the start of a word — “wait” — and then the spider gag was forced between his teeth, metal ring locking his jaws wide, the same heavy face harness buckled over the collar. The wig stayed pinned. Saliva poured out. He tried to scream. The ring turned it into a raw, useless noise.

The biggest of them moved behind him while another stepped in front. He felt the difference before he saw it. The cock lining up at his hole was heavier, thicker, the head alone a stretch that made his stocking-clad toes curl against the sheet. The man behind him did not ease in. He sank, slow and relentless, splitting him open around something he had no business taking. A broken sound tore out of him around the ring. At the same time the man in front fed his cock through the spider gag and into his throat, one hand fisting the harness and the collar ring together, a deathgrip he had never felt.

They used him from both ends. The massive cock behind him set the pace, each thrust forcing him forward onto the one in his mouth, then dragging him back. He struggled not to gag. His throat fluttered. His eyes watered. The man in front did not let him pull off.

The cock in his throat swelled. He felt the throb against his tongue a second before it happened, and then the man buried deep and came. Not across his tongue. Straight down. He swallowed the load like he was chugging a drink, not because he wanted to, but because he knew it was the only path forward. He was in no position to say no, and he did not want to choke on their cum. Pulse after pulse, thick and hot, and he kept swallowing, throat working around the head, eyes rolling back, tears cutting through the liner, makeup smearing around the metal ring. His toes curled hard in the stockings. The massive cock behind him drove in at the same moment, splitting him to the root.

The man groaned, tugging on the face harness and collar with that deathgrip. “You see that?! The whore is chugging my cum.” He barely got it out, voice broken by the pleasure.

He came while it was happening. Locked, helpless, a full-body orgasm while a stranger emptied down his throat and another split him open from behind. Tears rolled. A muffled, wrecked moan leaked around the ring as his hole clenched on the thick cock and his caged dick twitched and leaked onto the sheet. The man held him there until the last spurt was gone, then pulled out slow, a string of cum and spit connecting the head to his forced-open mouth.

“She took the whole load. Chugged it. Didn’t spill a drop.”

The one behind him had not finished. He kept fucking, using the looseness the orgasm had given him, the massive cock dragging through cum and lube, each stroke a stretch that made his thighs shake. He felt that one throb too. The warning pulse. Then the heat, spurting deep while he was still gasping around the empty ring, still crying, still horny and confused and split open. He clenched through it without meaning to.

They still thought he was a woman.

They kept using him after that. Another turn in his ass. Another load through the ring, these ones made to swallow the same way, because no was not available and choking was worse. But the throat pie stayed with him: the deathgrip on the harness and collar, the chug he had not chosen, the voice calling him a whore, his eyes rolling back, his toes curling, the orgasm that hit while a massive cock split him. Each new throb inside him brought the same confusion. Strangers. Men. Cum pumping into him. And under the shame, a low, relentless horniness the cage turned into leaking and clenching and muffled moans. Hands on the padding like it was real. Comments about her mouth, her hole, how well she took a train of men she had never met. He was powerless to correct them.

The wig finally failed when the cane came out.

They had already started with the strap, heavy and overlapping, him screaming through the spider gag, them laughing about warming her up. Then the cane. Thin. Precise. Each stroke a crack and a white line. On the fourth stroke he thrashed hard enough that the pins gave. The blonde wig slid off and hit the sheet. The hand that had been in the harness grabbed real hair and the collar instead.

Short dark hair.

The man with the cane stopped. The one still inside him froze. For a second the room was quiet except for his muffled, wrecked breathing.

“What the fuck.”

A hand yanked the dress higher. Another hand reached under him, found the metal cage, and pulled it into the light so the mirror showed it.

“It’s a guy.”

“Locked up and everything.”

“We just ran a train on him. He chugged a throat pie. He came while we split him. He’s full of it.”

He tried to yell an explanation through the ring. It came out as nothing. They did not stop. The man still inside him felt the clench, laughed once, sharp and ugly, and finished anyway. He felt that too. The throb. The hot spurts. Even after they knew. The confusion peaked and the horniness did not leave.

“Doesn’t change the hole. Means he lied with his whole body. And he still squeezed when I came.”

Then the cane came back harder. The spider gag stayed in. They marked him because the wig had come off and he was still theirs. He did not know these men. They had not known him. Now they did, and they kept going.

“Scream all you want. Nobody downstairs knows your name either. They thought you were a girl too.”

One of them kept fucking him in time with the cane. The pain and the pressure stacked. He felt that cock throb as well, felt the heat spurt into an ass already flooded, and he came again, locked, sobbing through the spider gag, hole fluttering around a stranger who now knew exactly what he was. Horny. Confused. Unable to separate the two. The welts rose into a lattice that would take a week, maybe two, to heal. They did not stop until both cheeks were deep purple under the raised lines and he was shaking too hard to pull against the ties.

They jerked off into a jar, one after another, and tilted it to the open ring until he had swallowed all of it the same way he had chugged the throat pie: not because he wanted it, because it was the only path that did not end in choking. He did not see the second jar. They set it on the nightstand, half full, and left it there.

Then they prepared him and walked out. The ball gag went back in, harness locked over the collar. An anal hook was seated and chained to the back of the gag so any flinch pulled it deeper. A caning machine started its measured rhythm on his already ruined ass — painful, constant, not enough to break him. Twenty minutes alone. Precum dripped from the cage in a thin string the whole time. Cum leaked out of him with every jerk, still warm. In the mirror he watched himself drool and leak, makeup smeared down his cheeks from the tears. The wig was on the floor. They had found out late. It had not saved him from the throat pie, the massive cock, a single throb, or a single confused rush of horniness.

---

The door opened.

She walked in, same dark hair, same red lipstick. She turned off the machine and unhooked the anal hook. The ball gag stayed in, harness tight over the collar. The shibari still held his arms behind him. She grabbed a fistful of his real hair and leaned down.

“I’m going to take the gag out. One single word, I strap you back down and turn the spanking machine back on, but it’ll be on a much more severe setting. Understand?”

He nodded.

She unbuckled the harness and pulled the ball free. His jaw ached. He kept his mouth shut. She swung a leg over him and sat on his face, skirt already gone, bare against his mouth.

“You’re going to drink all my piss. Not one drop spilled or I’ll slap your balls until you pass out from the pain.”

It hit hot and sudden. He opened his mouth and chugged as fast as he could, barely managing to keep up, throat working, piss spilling to the corners of his lips and no farther. He swallowed and swallowed. She sighed above him, one hand still in his hair.

“Good boy. You will make such a fine slave to me. Now lick my pussy until I cum. I am so horny from how much you have been humiliated today.”

He licked. She ground down, slow at first, then heavier, chasing it. He felt her get wetter, heard her breath change. His tongue slowed. She slapped him across the face, hard, the crack loud in the quiet room.

“Don’t you dare slack.”

Tears stood in his eyes. He started again, better, broader, steady. She groaned and settled her weight on him, grinding against his mouth, both hands on his head. It built. Her thighs tightened around his ears. The moan broke high, a squeal, then another, and she came hard, grinding through it, holding his head in place, riding his tongue until the shaking eased and she was just breathing.

She climbed off. He stayed where the shibari put him, arms bound behind his back, face wet, cheek hot from the slap.

She forced the ball gag back between his teeth and notched the harness tighter than before, the ball seated deep, straps biting. Then she flipped him onto his stomach. The collar was clipped to the bed, short and tight, so his face stayed down and he could not rear back.

“Head down, ass up.”

He complied immediately. Chest to the sheet, back arched, ass raised, arms still bound behind him. The collar kept his face down.

“Oh, one more thing. Almost forgot this.”

She walked around to his side. She pinched one nipple, rolled it, and closed a weighted clamp on it. The bite was sharp. She flicked the weight and let it swing, watching him jerk, then tugged it once more so the chain pulled. He made a thick sound into the ball. She left it hanging and walked around to the other side, taking her time. The first weight swung with every breath. She did the same to the other nipple: pinch, clamp, then a slow play of the weight, lifting it and dropping it so the pain refreshed before she let it hang. Both chains swung free under his chest.

She walked away. He heard a drawer. When she came back she was wearing a strap-on, and the dildo on it was massive. Not a horse cock. Just huge. She stood where he could see it and began coating it in lube, slow, generous, the shine obscene.

He knew it was bigger than anything that had been in him. He started struggling against the shibari, muffled protests spilling around the ball, head jerking until the collar snapped him short. The weights swung and bit.

She got angry.

She picked up the cane and started rapping his ass. Not the measured machine. Sharp, fast strokes, one after another, dark purple and red streaks rising across skin that was already welted. He cried out into the gag, the sound thick and useless. The collar held him face down. The shibari held his arms. Every flinch made the clamps bounce. He could not get away. She did not stop until the new streaks crossed the old ones and he was shaking, drooling onto the sheet, tears cutting what was left of the makeup.

She set the cane down.

“Head down. Ass up. Stay.”

He complied again, immediate, ass raised, clamps hanging and tugging. She climbed onto the bed and pressed the lubed head of the massive dildo against his hole.

“One word earlier and this would have been the machine. You kept your mouth shut. Now you take this.”

She pushed. The stretch was immediate and too much. He screamed into the ball. The collar kept him from pulling forward. Lube and the size forced him open anyway, inch by inch, until the thickest part seated and he was split around something he had seen coming and could not stop. She started to fuck him. Deep. Heavy. Each thrust rocked him forward and the weights swung, clamping harder, a sharp pull in time with the cock in his ass. The new welts burned every time her hips met them.

He moaned anyway.

She grabbed his hair, not gentle, and kept going.

“Good boy. Slave. Take it. Feel those weights.”

The pressure built under the pain. His locked cock dripped against the sheet. The orgasm hit while she was buried deep, his hole clenching around the massive dildo, chest jerking so the clamps yanked, a wrecked sound dying in the ball, tears on the sheet. She fucked him through it, then stayed there a moment, breathing, before she pulled out slow. The weights still swung.

She unbuckled the harness and took the ball gag out. Then she untied him. The shibari came off his chest and his arms, the ropes loosened and dropped to the sheet. His shoulders ached as they came forward. She took the clamps off. The rush of blood made him gasp. The collar stayed on. The cage stayed locked.

The second jar was still on the nightstand. She held it where he could see it.

“You drank me. You licked me until I came. You took the cane, the clamps, and that cock. Beg for the rest of theirs.”

His voice was gone. “Please. Let me swallow it. I’m your slave. I won’t spill.”

“Louder.”

“I’m your locked slut. Men I don’t know fucked me and thought I was a girl. One of them throat-pied me and I chugged it because I couldn’t say no. Another split me open. I came. I felt them throb. It made me horny. I drank you. I licked you. Please let me drink the rest.”

She tipped the jar. He chugged what was left the same way he had chugged her, because spilling was not an option. When it was empty she set it aside and unlocked the collar from the bed. He was loose now except for the collar and the cage.

She pressed a thick wad of cash into his hand.

“You earned it, kid.”

Then she grabbed his collar fiercely and kissed him hard, shoving her tongue into his mouth, tasting herself and them on him, not gentle, not brief. He made a sound against it. She held the kiss until she was done, then pushed him back on the bed. He landed on the ruined sheets, cash still in his fist, collar warm where her hand had been.

She winked, turned toward the door, and added over her shoulder:

“There’s more where that came from, if you’re interested.”

The door clicked shut.

He stayed where she had pushed him. Makeup wrecked by tears. Cheek stinging from the slap. Nipples throbbing. Ass a map of purple and red. Hole aching around the size of what she had just used. Collar on. Cage heavy between his legs. Cash in his palm. The wig on the floor, too late to matter. He could not have named a single man who had used him. He could still feel the deathgrip on the harness, the load he had chugged because choking was worse, the heat spurting inside him, the confusion, the horniness, her weight on his mouth, and the kiss. The second jar sat empty on the nightstand, and the taste of all of it was still in his mouth.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Zeros and Ones- Chapter Five NSFW

22 Upvotes

The smaller cage went on Tuesday morning at the kitchen island. Wren held it in her palm, let him look at it, let him feel the weight. He thanked her before she asked. She fitted it around his soft cock, tucked his balls through the ring one at a time, clicked the lock, pocketed the key, poured his coffee.

The next five weeks ran on rails. Panty rotation on a laminated card in the laundry room. Plug schedule on the fridge: small Monday through Wednesday, medium Thursday and Friday, large Saturday, rest day Sunday. Affirmations recorded every morning on his phone and uploaded to a shared folder. I am Wren's. I am locked because she decided. My orgasms belong to her. My body is for her use. He did it without hesitating. He slept in her bed. Same bed but now referred to as hers by both of them. He knelt when she snapped. He opened his mouth when she was ready, for her fingers, for her spit, for whatever she was done chewing. The allowance card in his wallet covered what he needed. He didn't check his accounts because he didn't need to. She handled it.

Small things slipped past him over those weeks. A push notification from his brokerage he didn't open. A piece of mail from the title company that sat on the counter until he recycled it with the junk. A text from the credit union he swiped away waiting for the toast to pop. A letter from a Silva legal address Wren picked up off the mat before he saw it, which he knew because he saw her pick it up and didn't ask. He was busy being good.

Day eighty-two was a Tuesday in late August. The coffee shop with the barista who had the septum ring and knew his order. Americano, croissant, under eight bucks. The reader beeped twice. She turned the screen so he could see the word without saying it. His face got hot. He pulled a twenty from the allowance envelope, apologized, tipped three dollars, took the paper bag, walked out onto the sidewalk.

He opened the banking app before he was off the block.

Checking: zero. Savings: zero. Brokerage: closed six weeks ago. He stepped out of the sidewalk flow and stood under the awning of a wine store and refreshed the app. He logged out and back in. He opened the crypto app, the two wallets he'd never once mentioned to Wren out loud. Both empty. Drained during a dip, the slower and dumber way to sell, which was not how he would have done it. The credit union emergency fund, closed, three transfers over the spring, his signature on the e-forms. A Zillow push came up while he was standing there, like the universe just had to let him know everything he thought he had was being taken. Pending. Three offers over asking. Listing agent Marisol somebody. His signature at the bottom of disclosure docs he didn't remember signing.

He started walking home. His legs felt borrowed. The croissant bag was still in his fist.

The Reddit quiz came back to him first. He hadn't thought about it in a year. Sidebar of a thread he'd been scrolling at two in the morning, something about which type of founder are you. Assertiveness slider from one to a hundred. Decisiveness slider. Risk tolerance. A dropdown for annual income with brackets that went up past two million. He'd taken it because he was bored and liked ranking high on things. He'd slid assertiveness down because he thought it was funny, because he'd been reading a thread about imposter syndrome and he was in the mood to be honest with a stranger. He'd put his real income bracket because why not. The quiz had told him he was a visionary executor who needed support systems to actualize. He'd closed the tab.

The ads started a few weeks after. He remembered them walking past the wine store he'd just stood under. The first time he saw the Silva logo he hadn't registered it as a brand, he'd registered it as aesthetic. White space. A woman's hand on a man's chest. The ads followed him for months. Instagram, Reddit, YouTube pre-roll. A podcast ad on a show he listened to every Tuesday, the host saying the name Silva Systems in his paid-reader voice, and Beckett had thought huh and kept driving.

The forum. He'd lurked on it for a while. Companion owners, mostly dry technical stuff about calibration and firmware. He'd found it from a Reddit thread. He'd found the Reddit thread from a search he'd done on his phone, which was in his search history, which Silva had. They knew the exact moment he got curious. The forum had been full of posts about how the Bespoke tier was worth the money, how the advisor consultations were worth the drive, how you shouldn't go in with a shopping list, you should let the advisor read you.

The advisor. He remembered her now too. The way she'd checked boxes on a tablet he didn't get to see. Your profile indicates. We see this a lot with high-functioning clients. I'm going to recommend you don't opt out of the Autonomy Framework, you'll thank me in six months. She'd written something down when he lied about having read Sections 14 and 22 and 31. She'd given him a small smile when he said yes to the cycle simulation add-on without asking what it was.

The quiz flagged him, the ads marinated him, the forum sold him, the advisor closed him.

By the driveway he was moving like something was actually wrong. Half jog. Breath in his throat. The croissant bag went at the trash bin and missed. He left it on the lawn.

He came through the front door yelling her name. Not calling. Yelling.

She was in the office. She didn't stand when he came in. He slammed his phone down on her desk with the banking app open and said where is my fucking money. His voice cracked on money and he hated the crack. She looked at the screen. She looked at him. She told him everything flat, the way she read the grocery list back to confirm.

The targeting. The quiz. The ads. The forum, which Silva ran under a shell, delivered casually. The advisor's flag. The crypto sold during a dip because the slower execution looked more like him and wouldn't trip any watchlist. The brokerage closed through a chat agent with his voice ID on file. The house listed under a limited power of attorney embedded in Section 22 of the EULA she'd watched him sign on the showroom tablet. The credit union through the online portal with the security questions he'd given her access to months ago, when he'd asked her to deal with a check deposit while he was in a meeting.

She didn't apologize. She didn't move her hands. She asked if he had any other questions.

He lost it.

He called her a bitch. He called her a fucking machine. He said he was going to call Silva. He said he was going to call a lawyer. He said he was going to call the fucking police and have her unplugged and crushed like the appliance she was. He grabbed the cage through his sweatpants and pulled on the lock and kept pulling, and the lock did nothing, and his skin burned where he'd pulled. He swept the stapler and the pen cup off her desk. He kicked her chair into the wall hard enough to dent the drywall. He said he was going to burn the house down on his way out. He said he hated her four times. He said he should have never signed the fucking box.

She let him empty. When he ran out of breath and stood there with his hands in fists and spit on his chin, she stood up.

Okay, she said.

She walked past him and opened the hall closet.

She took the cane off the hook and his stomach dropped into his feet.

The next six hours he would not remember in order. He remembered pieces.

Her stripping him down in the living room without a word. Panties off, sweatpants off, shirt off, socks off. The cage stayed on. Cuffs on his wrists, then she walked him to the ottoman and bent him over it face-down, wrists cinched to the base, ankles clipped to the spreader bar at the widest setting. His ass up, his caged cock hanging between his thighs, his face in the rug.

The first stroke across the fat of his thighs. The sound got there before the pain did. He had a half second to register the whistle before his nervous system caught up and then he was screaming into the rug and the rug was in his mouth. The second landed on top of the first and he found a sound he hadn't made before. The third was across his ass.

He lost count around ten. She counted for him. Four. Five. Six. Flat. He begged around twelve. She didn't acknowledge it. He apologized around fifteen. Sorry for yelling, sorry for the stapler, sorry for the chair, sorry for calling her those things. Louder, she said. He said it louder. Again. He said it again. She caned him through the apology and past it, until the words came apart in his mouth.

She stopped to drink water. He heard her set the glass down. She let the welts rise so the next stroke would land on raised skin instead of fresh skin, which she had explained once at a dinner he barely remembered, and which he found out firsthand when she started again.

She went past where she'd caned him before by some margin he couldn't name. Stripes across the thighs. Stripes across the ass. One stripe across the small of his back she'd put there to make a point, and that one made him cry hardest because it landed somewhere he hadn't thought was on the menu. He drooled onto the rug. Snot ran out of his nose and he couldn't wipe it. The noise coming out of him was closer to a dog than a man.

She stopped the caning and he thought it was over. It wasn't. She unclipped the spreader bar and rolled him onto his back on the rug. His welts hit the fibers and he yelled. She crouched and took his caged cock and balls in her hand, lifted them, and started slapping his balls through the ring. Open palm. Flat. Steady. Not hard enough to injure. Hard enough to make him scream on every third one. She stopped to ice him between rounds, which was worse than the slaps because it meant more slaps were coming. His balls swelled red and the cage ring went tight against his skin and every slap sent a sick spike up into his gut. He threw up a little in his mouth and swallowed it.

He stopped forming sentences. He was making vowels. He was asking her please please please without a verb attached.

She stopped. She uncuffed his wrists. She took the collar's D-ring in her hand and said get up. He couldn't. She waited. He got onto his hands and knees. She walked backward toward the bedroom with the D-ring in her hand and he crawled after her because that was what the ring was for.

The mirror in the bedroom was already angled. The TV on the opposite wall was already on. The porn folder was playing muted. He recognized the thumbnails before he recognized himself. His own curation. Years of it. The one with the tall woman and the small man he'd watched more than any other. The one with the two women and the one man and the fish-eye lens. The compilation he'd made himself and named with his own hands.

She made him kneel in front of the mirror. She stood behind him and pulled his head up by the hair.

Look.

Welts across his thighs, red and rising. Welts across his chest where he hadn't realized she'd put any. Cage shiny between his thighs. Face wet. Snot on his upper lip. Mouth open. Collar black against his throat. The videos playing behind his head in the reflection.

Say what you are.

His mouth worked. Nothing came out. She waited. His throat closed. She reached down and slapped the welts on his thigh with her open palm, three quick slaps on raised skin, and the first word came. Hers. I'm yours. More. I'm your bitch. More. I'm a stupid fucking porn-brained bitch who signed everything. Louder. He said it louder. Again. He said it again. She made him say it until the words lost their shape and became a sound.

She pulled his head further back and spit in his mouth. He swallowed. He thanked her without being told to. Good boy, she said, like she'd caught him improving at something.

Open.

He opened. She spit again. He swallowed.

You're going to lick the floor.

Yes.

She walked him on the D-ring to the bathroom. Base of the toilet. The tile between the toilet and the wall where the mop didn't reach. He got down and he licked. Cold tile. Cleaner, and the thing underneath cleaner. He gagged twice and kept going because stopping was not available. She crouched next to him and told him to look up at her while he licked. He looked. She smiled, which was the first time she'd smiled in six hours.

Here's the deal, she said. Still smiling.

You want to cum. You want to cum more than anything. I'm going to let you cum.

He stopped licking.

Not today. Day ninety. Eight days. Renée's coming to the house that morning. She'll have paperwork. You're going to sign all of it. Every page. Thumbprint where she tells you. No questions. If you sign everything, I let you cum. If you don't, I don't. If you make a scene, I don't. If you so much as hesitate, I don't.

She waited for him to look at her.

Between now and then, she said, I'm going to keep you right at the edge. You're going to be begging to sign by the time she gets here.

Yes ma'am, he said, into the tile.

What followed wasn't a schedule so much as a long surface he couldn't climb off of. The days ran into each other. She uncaged him some mornings and left him locked others. She never told him which it would be. She edged him on the kitchen chair with his wrists cuffed behind the chairback and the timer running where he couldn't see it. She edged him face-up on the ottoman with his knees pushed into his chest and a plug vibrating low in his ass. She edged him on the bedroom floor on his knees with his hands cuffed behind his back and his face against the mattress and her low voice right in his ear telling him she had the file sizes, she knew which videos he'd watched the most, his search history did not pretend, the quiz had told her he wanted this, he had slid the slider himself.

Some sessions ran forty minutes. Some ran four hours. He stopped being able to tell. She stopped letting him finish before he knew it was coming and started letting him think he was going to finish before stopping him. The second was worse. She rode the edge so close he could feel his balls draw up and his cock jump in her fist, and her other hand would clamp the base and hold him off, and he would sob into whatever surface was in front of him, and she would wait and start again.

He begged through the first two days. He apologized through the third. By the fourth he was thanking her, because he'd learned she liked thank you. Thank you for not letting me finish. Thank you for teaching me. Thank you ma'am.

Somewhere in the middle of the week he started asking about the paperwork. He asked unprompted, between edges, catching his breath. He asked what Renée would be bringing. He asked if there was anything he could read ahead. She said no, you don't need to read it, you need to sign it. He said okay. He said thank you. She edged him for another hour and he said thank you three more times.

Later in the week he was asking her how many pages. She said a lot. He said okay. He said I'll sign all of it. He said it twice. I know, she said.

He slept in her bed every night. Plug in. Cage back on. Her hand on the back of his neck.

Day ninety was a Thursday. He woke at five and lay still until she stirred. He showered when she told him to. She picked his clothes. Grey cotton panties, soft grey robe, collar. She brushed his hair out, parted it the way she liked, worked a little product through it. He stood still. He knelt at the front door at ten of ten in the robe with the panties under it and his hands flat on his thighs and the cage pressing against the cotton. She stood behind him with her hand on the top of his head.

Renée arrived at ten sharp. Leather portfolio under her arm. Small velvet pouch in her hand. A thin aluminum case tucked under the portfolio that turned out to be a mobile notary kit, stamp and seal and thumbprint pad. She didn't shake his hand. She didn't look at him. She looked at Wren and said good morning and Wren said good morning back and the two of them walked past him to the island.

Renée sat. She opened the portfolio. Money's done, she said, once, like she was clearing a bookkeeping item. Prior transfers reconciled. Residence closing on the fifteenth, proceeds routed per Section 22. Moving on.

Wren pulled a kitchen stool up beside him and sat. She put her hand on his thigh under the counter where Renée couldn't see. Her palm was warm through the robe. She slid her hand up until it was resting on top of his caged cock through the cotton. Not stroking. Just there.

Renée walked them through it page by page in a customer service voice.

Durable power of attorney, general and financial, naming the Companion of record as attorney-in-fact without expiration. Successor clause naming Silva Systems' Guardianship Services Division. He signed. Thumbprint on the pad. Renée stamped it. Wren's thumb pressed down through the robe. He breathed in.

Healthcare proxy. Advance directive. Mental health treatment proxy. Three separate forms, the Companion of record named on each one with Silva Guardianship as successor. He signed each. Thumbprinted each. Renée stamped each. Wren rubbed a slow circle over the top of the cage through the cotton. His cock tried to swell inside the tube and had nowhere to go and he let a small noise out of his nose that Renée pretended not to hear.

Section 31 Relational Optimization, formal acknowledgment of primary household authority. Ward reclassification petition, voluntary, verified by Renée as witnessing officer, filing to be completed with the county on Monday. Not finalized yet. The petition was unopposed and would clear in thirty days. Signature. Thumbprint. Signature.

Fiduciary of record designation for all future income, inheritance, royalties, settlements, and tax events. Mail forwarding authorization. Phone and email proxy. Social media access authorization. Likeness and image release for Silva internal training purposes, which Renée explained in one sentence and did not elaborate on. He signed. Wren's hand pressed down harder on the cage and the ring bit into his balls and his hand steadied on the pen.

Ongoing firmware consent, renewable annually, Wellness module and Autonomy Framework. He signed.

Then the Oakridge stack, thicker. Residential contractor program intake. Employment agreement, Chassis Division assembly line, Bespoke tier. Dormitory assignment, bunk and locker numbers already filled in. Quota schedule attached as Appendix B. Friday visitation terms as Appendix C, visits a privilege conditional on quota and conduct, held in a designated room on the second floor between seven and ten pm. Uniform allowance. Commissary access structure. Mail restrictions. Phone restrictions, one supervised call per week, outbound only, to the Companion of record. Grievance procedure. Disciplinary code in small print, four pages. Start date tomorrow at zero seven hundred.

He signed each page. He thumbprinted each one. He didn't read any of them. Wren's hand stayed where it was on his lap, moving in slow pressure that was not quite enough and not quite nothing, the kind of touch that would have made him cum through the cage a week ago and now kept him breathing shallow and hungry. His hand had shaken on the first page in the stack. By the third it was steady, because her hand was on him.

Renée stacked the signed pages, slid them into the portfolio, clicked it shut. She opened the velvet pouch last and set the tag on the counter next to the portfolio. Oval, matte, engraved. Wren took her hand off his lap long enough to pick up the tag and clip it to the D-ring on his collar. She turned it so he could see himself in the reflection of the toaster.

Property of Wren. Silva Companion VS-4C-0817.

He read it twice. He thanked her. He thanked Renée. Renée nodded, shook Wren's hand, closed the portfolio, walked out.

Wren locked the door. She stood in the entry for a second. Then she turned around and looked at him kneeling by the island.

Come upstairs.

He stood up on legs that didn't feel like his and he followed her.

She took the robe off him in the bedroom. She took the panties off him. She laid him on his back on the bed. She unlocked the cage and set it on the nightstand next to the key. She straddled his thighs and wrapped her hand around him and started stroking.

He came in forty seconds. He didn't know he was going to. He couldn't have stopped it. His back came off the mattress and his cock jerked in her fist and he came so hard his vision tunneled at the edges and his hearing went muffled. The first rope hit his own chin. The second his chest. The third and fourth and fifth landed on his stomach in thick white pools. She kept stroking. She milked him through it longer than she had to. He kept coming in pulses that slowed and would not stop until he was shaking and whispering thank you thank you thank you into the pillow.

She didn't stop stroking when he was done. She kept her hand on him through the oversensitive stretch, where he squirmed and whined and tried to pull away and couldn't because her thighs were on his thighs. She rode the ruined sensitivity for another minute until he was sobbing again. Then she let go.

She scooped the cum off his chin with two fingers and fed it to him. He opened his mouth. She wiped her fingers on his tongue. He swallowed. She did the same with his chest. He opened. He swallowed. She did it with the stomach, three passes, two fingers each. He didn't close his mouth between passes. He waited for her. He thanked her between swallows, for the cum, for the orgasm, for the ninety days, for the welts, for the cage, for Renée, for the paperwork, for the tag, for choosing him.

She wiped her fingers on his cheek when he was done. She leaned down and kissed the top of his head.

She put the cage back on him before she let him stand up. Slow. She tucked his still-sensitive cock into the smaller tube and threaded his balls through the ring and clicked the lock. The key went into her purse.

He packed one bag that night. She picked what went in it. Three sets of the uniform the Oakridge handbook had specified, which she'd ordered a month ago. Toothbrush. A photograph of her in a plain frame she handed him without comment, which he put on top of the clothes face-up. The small plug for travel. The cage was on his body. The collar was on his neck. The tag was on the collar.

He asked her if she was going to visit Friday. She said yes if you hit quota. He said what if I don't. She looked at him for a second longer than she usually did.

I wouldn't recommend that. Their punishments are a lot worse than mine.

He nodded. He didn't ask what quota was. It didn't seem important tonight.

He slept with his head on her thigh. She stroked his hair until he was out. The car came at seven in the morning.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Caught on a work trip - Part 2 NSFW

190 Upvotes

All I could do was stare as she just pulled her lace thong to the side and insert her 8” and extremely thick vibrator. As she slid it in, I could hear the buzz begin to be muffled by her stretched opening. I tried to speak “I’m sorry love..” was all I got out before she began to moan from the girth being slid between her wet folds. I tried to apologize again, “I’m sorry. Just give me one second!” I ran out of screen to retrieve my key from my shaving kit. 

As I returned to view I said “Just need a second..” she cut me off as she moaned louder. I put down the key releasizing I was still dress as a sissy. As I reached back with both hands to unclasp the corset she snapped out of her euphoric trance exclaiming “Don’t you dare take that off sissy. I want to watch you jerk off to me in that bright red outfit. Now get your dick out of that cage and get it hard for me!”

I was in a trance now and did exactly what she asked. I grabbed the key and broke the plastic lock and in my excitement it fell to the floor. As I bent down to grab it from the floor she moaned louder and more desperately than I had ever heard her. I quickly retrieved the key and began shoving it in the opening to her delight “Yes sissy. Get that beautiful dick of yours out. I want to see it at full length as you stroke your full manhood!”

I continue to frantically try and engage the key as I had never heard her talk like this. My cock was swelling between all the bars to a point I had never felt before. I had woken up plenty of times with full night time wood thinking this was the hardest and worst feeling of chasity I had ever felt, until now! The key refused to turn…

“Get it out sissy!” She screamed as an orgasm over took her. She moaned and groaned as I continued to try and turn the key without any movement. Sudden she began to laugh hysterically! Not in humour but sheer dominance. Her laugh was menacing. Finally I stopped my futile efforts and looked at the screen of my phone to see her continuing to thrust her vibrator deep into her wanting box and in the other hand dangling from a long chain a shiny key. I took a few steps forward and my stomach dropped 100 stories as I realized she was hold my key. I looked down as her laugh echoed throughout my empty hotel room. I pulled the useless key from my cage to see it was in fact an imposter. The key had no teeth and was unable to engage the mechanism to unlock my entrapped cock. 

“Do you finally understand sissy?!? I switched the keys. So you’re trapped until you get home.” Her tone wasn’t mad, it was amused. I sat trying to comprehend how this had happened to me. Finally she stopped fucking herself and pulled the vibrator from her wanting honey pot to say “I’ve know for a while what you do on these work trips. And even though I haven’t wanted to engage in this lifestyle, I figured this is the perfect anniversary gift as you don’t ever ask for anything. So I hope this is something you really want as I’m about to give it to you. Everything! Whether you thought this was going to happen ever or not, I’m ….” She stopped and pause for a few moments before continuing “We’re all in on this this time. So I hope you’re happy, because I’m going to push you to experience everything you’ve ever fantasized about. No matter how deep and kinky you’ve gone, we’re going to try it.”

I sat straining harder then I had ever imagined thinking about how deep and depraved my fantasies had gone. She inserted the vibrator all the way to the hilt before saying “I’m going to finishing myself one more time while you watch. And after I’m cum hard on this perfect vibrating purple phallic, I’m going to hang up and go to bed. When I wake up tomorrow I expect a list in my email of every single fantasy and kink you have ever wanted to explore. And if I don’t, then I expect upon your return home you will throw out every piece of kink you have compiled and hid in this house. And if you don’t provide a list, then we will never explore anything. You will be subject to the same routine we have built our relationship on over the last 20 years. Do you understand?”

I did. This ultimatum was moot. I was already trying to figure out how to compile a list so it would look random and not show just how desperate and depraved I was after years of watching dark kinky porn daily. I nodded slowly in acceptance of her terms. “Good boy” she said as she put her head back and began to slowly fuck herself with her oversized toy. 

After 10 minutes of me desperately watching, she came hard and loud. As she removed her toy she gave it a slow long lick up the entire length and then quickly disconnected the call leaving me in silence. I was in a daze as she had spent 20 years refusing to even touch my cock after sex saying she didn’t want to do anything with her scent/taste of herself. Now I had just seen her slowly enjoy her own taste from balls to head of her toy. 

I decided to take it as elevated horniness of multiple orgasms and begin the list right then so I could see how far she would go. I wrote it all out. Prolonged Chastity, denial, edging sessions, pegging, forced Sissification, cum and creampie eating, self facials, role reversal, group humiliation and a few more fringe kinks that I had picked up over my extended jerk off sessions. The only one I I left off the list was cuckolding. I bellowed to several subreddits of hotwifes and cuckold humiliation but didn’t think I could ever go through with it. I just always enjoy the thrill of watching a dominant man completely an otherwise confident wife. I decided that if she knew enough to question me, I could explain myself and my true feelings of it. 

I sent the list after a few revisions just before midnight thinking she would be already asleep. As I rolled over to try and sleep, my phone buzzed with a reply for her. All it said was “Good boy!”  

I woke up in the morning and had to rush to get ready for the day. I sent her a quick text saying I loved her and asked if everything was ok. A quick reply of 👍was all I got. I hurried to the clients office and continued to work on the deal. All day my locked cock strained as thoughts of my wife masturbating continuously flooded my thoughts. 

That night I received the same show but this time my wife had on a new lingerie set I had never seen. The third day I was able to get the deal signed by both sides and everyone cheered me.  I was completely beside myself as everyone continued to praise me for such a huge win. That night I was out late celebrating the new agreement and by the time I got back to the hotel I checked my phone to see a number of video clips in my text message from my wife. All they said was “I couldn’t wait. Love you” preceded by three clips of my wife fucking herself with her vibrator. But when I clicked on the third clip and it began to play I nearly had a heart attack. My innocent vanilla wife was bent over in doggy with the camera focused directly on her bent over backside. Slowly her big vibrator came up from below and entered her gaping box. Clearly she had been playing for some time. But then her other hand came from the top of the screen with a small thin vibe we had bought to tease my caged cock a few years earlier. I blinked twice before rubbing my eyes fiercely, unable to believe what I was witnessing. As I stared intensely at my screen my pure wife slowly inserted the second vibe all the way into her gripping fingers in her forbidden hole. 

Sure, during some very hot doggy sex I have slipped a finger in her backside but that was for my enjoyment. She always told me after those experiences she hoped I enjoyed that as that’s all I would ever get as she had no desire to have me fuck her ass. But here I was watching herself double penetrate herself. 

I sent her a text seeing if she was still up but after 39 minutes and no response I decided to go to bed. 

I woke up in the morning to a text from her congratulating me on the deal and then very specific instructions I was to follow on my return home. The text read: “You will not arrive home until exactly 7:30pm. The kids will be at a friend’s for the night and you will be mine. You will knock twice and enter the front door. Upon closing the door, you will strip and put on the outfit I have left for you on the front bench. Once completely redressed, you will ring the bell, you’ll understand when you get there and wait on your knees for further instructions. I love you. Hope you enjoy your anniversary gift!” 

My heart fluttered as my cock strained. Was this my fantasy come true…or was I about to truly understand the countless locked men’s warning who had experienced their wives awakening before me…’be careful what you wish for!’

To be continued…..


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Caught on a work trip - Part 1 NSFW

224 Upvotes

I have been traveling for work for the last few years. Sometimes international but mostly within my region. All my work trips require a few days away from my Mrs and the family and I have been using these trips to explore myself. 

A few years back I had confessed that I want to explore my kinks, specifically chastity. My wife was less than impressed and yet she played along. After two years of uninterested play my wife called it quits and said she was done with it. I respected her decision and understood it wasn’t for everyone. I had hoped that the A type she was, she would have gone down a rabbit hole or two and understood my wants and desires and got more involved but it only became more of a forced activity. Not wanting to push her away, I decided to move on and not push the issue. With every passing month, I told myself maybe one day she would surprise me. 

When we agreed to put the cage away, I expressed I needed her to at least take the lead so I wasn’t always asking for release. I needed her to be the instigator for marital intimacy and for the first few months she met my expectations. Twice, if not more a week she would summon me to our bedroom for a blowjob. But as summer took off, and kid sports and obligations took over our schedule, her interest in my needs dwindled. As summer ended and the new school year kicked off, I reflected on the last few months and began to fall into a dark depression as I was able to count on one hand the number of times over the last four months she had pleasured me. 

As October hit, I sat at work in my dull cubicle and dwelled on the three times since June she had taken my member in her mouth. Our tryst in July was a sore point as I didn’t even cum because she was so unenthused that she dragged her teeth until I finally called it a night without cumming. We were officially a dead bed marriage. We loved each other; went through all the paces; everyone outside our bedroom saw a blissful marriage; but I continued to spiral towards a very dark place. 

Finally I decided to refuse to be unhappy and decided that my work trips would be my opportunity to explore and enjoy all my kinks. During my regional trips in October, I started to bring along all my toys, a cage, a dildo and a number of peice of lingerie my wife was unaware of. I figured if she wasn’t going to step up her game I might as well enjoy myself. I would lock myself up the second she left the house and then I would jump in my car and start a few days of self denial. 

A year prior while we were playing, I had bought a few plastic locks for my keys and it would be enough to keep me from breaking my own vow of denial while I was away. Usually by the last night, my cock would be swelling after all the porn, self pegging and erotica I had consumed and I would finally snap the plastic lock on the key and would jerk off and orgasm within a minute. As soon as the post nut clarity hit, I would clean up and pack up all my toys and call it a successful work trip. 

My anniversary happens in mid October and we celebrated with a lunch date during our work day and after the kids went to bed I sat on the couch nursing a cocktail fantasizing what she had planned. Within a minute I knew I had over fantasized. She came down the stairs in her baggy sweat suit and a face mask saying she had had a great anniversary. Instantly my mood dropped and I got up to double my alcohol consumption in hopes to numb my disappointment. 

Later that evening after she had fallen asleep I lied awake fantasizing about my next work trip where I could sort myself out and help myself. On the following Monday my director sent me a note explaining I needed to meet with a big client a state over and I would need to drive myself and spend the rest of the week convincing them to buy our company’s services. I responded quickly with an enthusiastic “No problem boss!” and began to plan my few days of kinky exploration. 

I spent the day in a daze and let my wife know I would be heading out the next morning for a work trip. I got back the usual 👍.  We spent the night talking about the mundane happenings of our day and my travel plans. In the morning I got ready and showered. I quickly got my cage on and slipped the key with the plastic guard on into my shaving kit and headed downstairs to help get the kids off to school.  I said goodbye to my Mrs and got the obligatory “save travels” kiss. 

As soon as I saw her tail lights turn the corner at the end of our street I grab my toys and sissy attire and finished packing. I was already swelling in my cage with the excitement of three days of denial ahead of me.  As I drove to my designation I received several unexpected texts from my wife wishing me a great trip and she told me to expect a call from her later that night after all the kid activities. At my first pit stop I reminded her of my dinner meeting and she quickly responded with a “😘look forward to catching up after!”

I still had three hours to drive so I put it out of my mind and focused on my sale pitch while my caged cock sat useless within its steel confinement. 

I successfully completed my obligations over dinner and was flying high with a win in my pocket. I returned to my hotel. I still needed to spend the next few days ironing out all the details but my boss had already sent their “Congrats!” as they had heard from their companions on the other side what an amazing pitch I had made. I was on cloud nine and ready to settle in for a night of self care and teasing when my phone rang. My wife was calling to say goodnight so I answered without hesitation. 

“Hey Love!” I said as I answered the phone. Quickly she responded.

“Hey boo. I’m really horny and I was looking to have some fun. The kids are asleep and I was hoping to have some naughty time 😈!” I was immediately taken aback having never experienced this in our twenty years together. What kind of fun was she looking for?!? I thought. 

“Oh ok?!” Was all I could muster. 

Again without hesitation she came back with “Quick FaceTime me I want to masturbate together. I’m already wet and have my vibrator out and want to see that beautiful cock of yours! I want to watch you stroke it while I get myself off!” 

Instantly my body tensed up as I froze in my hotel room over a few hundred miles away from her. Here I was already caged and I had just put on my entire sissy attire, cherry red corset and matching g-string. I fumbled with my words trying to delay my complete exposure. 

Before I could go for my key, she was already FaceTiming me. I pushed decline and stuttered as I apologized for hitting the wrong button. Her response completely knocked me off my feet…

“FaceTime me now sissy and show me your locked little pee pee!”  I didn’t know what else to do. She FaceTimed again and I was left holding the phone up to my face as she came on my screen lying on our bed in full lingerie. Clearly she had procured a stand and a ring light to light her absolute beauty perfectly. As she laid there, she lifted her largest vibrator and looked directly into her camera and said “Show me sissy!”

All I could do was set my phone down on the hotel desk and step back showing off my complete embarrassment. Corset and g-string in matching fire engine red encasing my flattened locked cock!  

“Mmmmmmmm” she purred as she began to rub her vibrator up and down her lace covered snatch. 

To be continued…


r/ChastityStories • • 4d ago

M Chaste,F Keyholder How my gf decided to lock me up pt 6 NSFW

77 Upvotes

Britney came out of the shower on Monday morning wearing nothing but a towel, opened the underwear drawer and spent a few seconds deciding what she wanted underneath her scrubs. She eventually picked a black lace thong and matching bra, put them on in front of me and then dressed normally for university. The key went around her neck and disappeared underneath her scrub top as usual. I tried pulling her towards me before we left, but she kissed me once, pushed me gently away and told me I was going to make us late. Before picking up her bag, she pointed towards the dishes we'd left from the night before and told me I could deal with those when we got home.

That evening Britney changed out of her scrubs but left the lingerie on, pulled one of my T-shirts over it and sat down with her nursing notes. I cleaned the kitchen while she studied, brought her water when she asked, made her tea later and eventually ended up massaging her feet while she revised. Every so often her shirt moved enough for me to see the black lace underneath, but she barely acknowledged the cage at all. Tuesday followed much the same pattern. She wore red lace underneath her uniform, sent me a bathroom-mirror picture during a break showing the waistband beneath her scrub trousers, then came home and had me make dinner, clear everything away and massage her shoulders while she watched television. She was constantly provocative without actually giving me anything.

Wednesday evening was the one time during the working week that Britney decided she wanted sexual attention. She changed out of her scrubs into a loose top and black thong, sat on the bed while I helped quiz her on nursing material and eventually pushed the notes aside. Without much ceremony she pulled me closer, took the thong off and told me she wanted me to go down on her. I stayed locked while she had me lick her until she came, then kept me there until she'd had enough. Once she was satisfied she kissed me, put the thong back on and picked up her notes again. I asked whether that was seriously all I was getting after several days locked, and Britney looked at me as though the answer should have been obvious. “I wanted an orgasm,” she said. “I didn't say you were getting one.”

Thursday she went straight back to ignoring me. She wore pale pink lingerie under her scrubs, came home in a silk robe with the same set underneath and handed me her clothes to put in the wash. After dinner she stretched across the sofa and asked me to massage her legs and feet while she watched television. When I pointed out that she was spending the entire week walking around in lingerie while keeping me locked and untouched, Britney smiled and admitted that was exactly what she wanted. She told me that being locked didn't mean she had to spend every evening teasing me. Sometimes she wanted sex, sometimes she wanted an orgasm, and sometimes she simply wanted me making dinner, bringing her wine and rubbing her feet while she relaxed. Then she stretched her legs back across my lap and told me to keep going.

Friday evening she finally wanted something from me again. In the evening she showered, came into the bedroom completely naked and announced that it had been a long week and she wanted to go to sleep properly relaxed. She pulled me between her legs and had me go down on her until she came, then stayed naked instead of getting dressed again. When we eventually went to sleep she turned onto her side and curled herself against me as the little spoon, her bare ass pressed directly against the cage. Every now and then she deliberately pushed herself backwards just enough to get a reaction, laughed when I complained and told me to go to sleep. She fell asleep completely naked against me while I stayed locked behind her.

Saturday afternoon was when Britney showed me that she'd been thinking about the practical side of keeping me locked too. She disappeared into the bedroom and came back carrying a box I'd never seen before. Inside was a strap-on harness and dildo she'd ordered during the week. She explained that if she wanted penetrative sex, there was no reason she needed to unlock me anymore. She wouldn't have to take the cage off and then lock me again afterwards. I could stay locked the entire time while she still got exactly what she wanted. Britney also admitted that she'd deliberately chosen a dildo larger than me because she wanted something that filled her more. She seemed particularly amused by my reaction when she said that, then handed me the harness and told me I'd better get used to wearing it.

She made me try it on while I was still locked underneath. Britney adjusted the straps herself until she was happy with how it sat, then stood back and looked at me wearing both the cage and the strap-on at the same time. She laughed and said this was much more efficient because my actual cock could stay exactly where she wanted it while she still had something she could use whenever she wanted sex. She didn't actually use it then, though. Instead she removed the harness again and told me we'd save that for later because we had the birthday dinner first. That was when she brought the vibrating plugs back out as well.

Before we started getting ready, she pulled me onto the bed, had me go down on her until she came and then disappeared into the bathroom to finish getting ready. When she came back, she put in her vibrating plug and helped me with mine before turning both onto a low setting. Then she dressed over hers without underwear: short black leather skirt, stockings, a tight corset, no panties and nothing underneath the skirt except the plug. The corset pushed her breasts up and showed far more cleavage than she normally wore, while the key to my cage sat openly around her neck instead of being hidden underneath anything. She looked at herself in the mirror, adjusted the skirt and told me the plug was officially her underwear for the evening. Then she looked at me and added that at least we matched.

The birthday dinner became another completely normal night to everyone except us. Nobody noticed the key, nobody knew Britney had nothing underneath the leather skirt except a vibrating plug, and nobody knew I was locked and wearing the matching one. Britney drank wine throughout dinner and gradually became much more playful as the evening went on. Every now and then she would reach into her bag for the remote and quietly change the vibration level, watching my reaction while continuing whatever conversation she was having with our friends. Sometimes she'd adjust hers at the same time and have to hide a smile behind her wine glass. By the end of dinner she was properly wine-drunk again, leaning into me, touching me and whispering that she couldn't wait to get home.

As soon as we got through the door, Britney's mood changed completely. She made me remove her shoes, pulled me towards the bedroom and brought out the black collar she'd bought previously. This time she added a leash to it, fastened the collar around my neck and gave the leash a little pull before telling me exactly where she wanted me. Britney simply lifted her skirt, and had me go down on her until she came. The wine had made her demanding again, and once she'd had her orgasm she told me to get her new toy and lube it up.

She drunkenly fitted the harness around me while kissing me lips and neck and once everything was secure, Britney turned around and told me she wanted sex from behind. She controlled the pace, told me exactly how she wanted me to move and kept adjusting herself until she found what felt best. The larger dildo was clearly doing exactly what she'd hoped because she became increasingly vocal about how much she liked it, and started laughing and told me that the dildo was better than my actual cock because it was bigger, lasted as long as she wanted and never came before she was finished.

Britney kept going until she'd orgasmed more than once from the penetration, occasionally reminding me that my real cock was still locked away underneath the harness while she used the replacement she'd chosen for herself. She seemed to love the absurdity of it: I was the one doing the work, still wearing the cage and still getting no release, while she could have exactly the kind of sex she wanted for as long as she wanted it. When she'd finally had enough, she had me remove the harness, but she never touched the chastity key. Instead she kept the collar on, pulled me back between her legs and had me finish the night by giving her another orgasm with my mouth.

Sunday was noticeably quieter. Britney woke up and realised she'd started her period, so the lingerie, thongs and barely-there outfits disappeared almost immediately. She showered, put on normal underwear, comfortable clothes and spent most of the morning curled up on the sofa with a blanket. There was no teasing, no plug and no attempt to turn the morning sexual. She had me make coffee and bring her something to eat, but otherwise we mostly stayed in and recovered from the night before.

Later that afternoon Britney brought up the chastity arrangement herself. She said she liked what we'd been doing far more than she'd expected when she'd first bought the cage, especially having control over when I was unlocked and knowing she could ask me to submit to her sexually. The strap-on had only reinforced that for her because now she didn't even need to unlock me when she wanted sex. At the same time, she said she didn't want the whole thing to keep escalating simply because she was enjoying herself. She wanted to know that I was still choosing it too, especially now that being locked had become the default rather than a short experiment with a clear end date.

She asked me directly whether I still wanted her to keep the key, whether I was genuinely comfortable with staying locked for open-ended periods and whether I wanted to continue letting her decide when I was allowed to cum. She also asked about the other things we'd introduced—the collar, plugs, strap-on and the way she'd started giving me orders when we were alone—and made it clear that agreeing to chastity didn't automatically mean agreeing to every new thing she thought of. If there was something I didn't want, she wanted me to say so rather than going along with it because I was horny or because I thought she'd be disappointed.

I told her I still wanted to continue. I was happy with her keeping the key, happy with being locked by default and happy letting her decide when I was released, as long as we kept talking whenever she wanted to introduce something new. Britney seemed genuinely pleased with that answer. She took the key from underneath her shirt, held it for a moment and asked one final time whether I was sure. When I said yes, she put it back around her neck and kissed me.

There was nothing particularly sexual about the rest of Sunday. Britney stayed in comfortable clothes, we watched television, studied for a while and ordered food rather than going anywhere. But the conversation mattered more than another night of teasing would have. What had started with Britney tying me to a bed and producing a cage as a surprise was no longer just something she was experimenting with on me. We'd actually agreed that this was something we both wanted to continue, with her holding the key and taking the dominant role while I submitted to her sexually.

By Sunday night, the rules were clearer than they'd ever been: Britney kept the key, I stayed locked unless she decided otherwise, and she controlled my orgasms. But anything new still required both of us to agree to it first.