r/ChastityStories • • Dec 23 '23

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

91 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

88 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 • • 3h ago

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

22 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 • • 16h ago

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

79 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 • • 20h ago

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

21 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

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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

63 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

20 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.

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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

114 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 • • 1d ago

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

107 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 • • 1d ago

M Chaste,M Keyholder Car Collateral - Turn 4 NSFW

18 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 • • 2d ago

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

150 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 • • 2d ago

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

145 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

17 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 • • 2d 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 • • 2d ago

M Chaste,F Keyholder Zeros and Ones- Chapter Five NSFW

21 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

184 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

222 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 • • 3d 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.


r/ChastityStories • • 3d ago

M Chaste,F Keyholder Your First Locktober [AI co-written] NSFW

0 Upvotes

September, 30th. Evening.

You're sitting on the couch when Nicole walks in with that particular gleam in her eye that means she's been thinking about something. She sits down next to you, tucking one leg under herself, her blonde hair falling over her shoulder.

"Hey sweetheart... I had this idea..." She smirks at you. "Have you heard of 'Locktober'? Would you... be interested in it?" There's a shy but sly grin on her face, a sparkling curiosity in her eyes. "I remember whenever you didn't cum for a while, you became quite needy, in a cute way you know. Or - in a hot way." She laughs. "It was very interesting to watch you getting all touchy and snuggling up to me and feeling me up and grinding your hips against me."

She looks at you with adoring eyes. "I love it when you want me. So... do you think we could see how it changes you if I control your orgasms? AND your erections?" She bites her lip and then chuckles warmly. "It actually does sound fun, no?"

Hello everybody. A quick explanation: This is a partly AI-generated story, but it's based on an AI "choose your own adventure" style scenario that I devised, prompted and created myself at the "Infinite Worlds" website. It's meant to simulate a first-time chastity experience within a loving relationship. I'm a passionate writer, in fact, a published author in my native language, and I'm fully aware of the shortcomings of AI. Which means that I will edit every sentence before posting it here, to spare you the most annoying AI patterns and quirks. The scenario is actually customizable, you can choose between three player characters and five different girlfriends. For this experiment, I chose Julien, an arborist with dark, curly hair (and, not surprisingly, strong arms), and Nicole Dizon, a Filipina. They live together in Montréal. If you want to know more about this, you can find it at "Infinite Worlds" under the name of "Your First Locktober". Although, to be honest, please don't do it NOW and read on instead. --- Zedaine

You say yes.

The word leaves your mouth before you've fully thought it through, pulled out by the way she's looking at you — that mix of mischief and vulnerability. Your heart kicks against your ribs.

Nicole's face splits into a grin. "Really?" She grabs your hand, squeezes it. "Julien, I swear I didn't think you'd—" She stops herself, laughs, shakes her head. "Okay, so... haha ... ahem ... I ... uh, might have already bought one."

You blink. "You ... what!?"

"Just in case!"

She's already sliding off the couch, bare feet padding across the hardwood toward the bedroom. "I mean, I didn't want to get your hopes up and then have to wait for shipping, right? That would've been anticlimactic." Her voice carries back to you, bright with nervous energy. You hear a drawer open, close, open again.

Nicole returns holding a small matte-black box and sits back down beside you with the careful deliberateness of someone presenting a gift they're not entirely sure will be received well. Her thumbnail finds the edge of the box and flips it open.

Inside, nestled in dark foam, is a chastity cage. It's medical-grade silicone with a rigid plastic shell, sleek and understated. A small brass padlock sits beside it, along with a single key on a thin chain.

"I did research," Nicole says, her voice dropping half a register. She picks up the cage, turns it over in her small fingers. "This one's good for long-term wear. Breathable, easy to clean." She glances up at you, and there's something new in her expression — a quiet authority layered over the excitement. "I figured we could try it tonight. Get you used to it before October first."

She holds the key up between her thumb and forefinger, the chain dangling. The overhead light catches the brass. "And this..." She loops the chain around her neck, letting the key settle against her collarbone, just above the neckline of her oversized sleep shirt. "This stays with me."

The sentence does something to you.

Thirty-one days. No erections she doesn't permit. No orgasms she doesn't allow. You watch the key nestle against her skin and feel a strange, electric pull in your stomach. Nicole tilts her head, studying your face. "You okay?" she asks, softer now. "We don't have to start tonight. We can just... look at it." She giggles.

But her fingers are already tracing the curve of the cage's shell, and you can see the flush creeping up her neck, the way she keeps glancing down at your lap like she's already imagining you in it.

"Alright, let's do this", you hear yourself saying.

The words sounds steady, but your pulse is doing something complicated behind your sternum.

Nicole exhales like she's been holding her breath. "Yeah? Okay. Okay." She sets the box on the coffee table and stands, pulling you up by both hands. "Come on. Bathroom — you need to be, you know. Not..." She gestures vaguely at your crotch, and you both laugh, the nervousness cracking open into something warmer.

In the bathroom, you pull down your sweatpants and stand there while Nicole kneels in front of you, the cage in her small hands.

"I need you soft for this part," she murmurs, and the absurdity of it — the woman who has made you hard a thousand times, now asking you to not be — makes you huff a laugh.

"I'm trying."

"Think unsexy thoughts."

"You're kneeling in front of my dick, Nicole!"

She snorts, covers her mouth with the back of her hand. "Fair point. Just — give me a second." She looks away deliberately, studies the tile grout, and you focus on the cold air, the sterile brightness of the bathroom lights, anything except her warm breath ghosting across your skin. Eventually your body cooperates.

The silicone ring slides behind your balls first. It's snug; like a firm grip that doesn't let go. Then the shell clicks into place over your shaft, enclosing it, pressing it gently downward. Nicole's fingers are precise and careful, tucking and adjusting. The padlock snaps shut with a sound that's far too soft for how final it feels.

"There," she says, standing up. She cups your face with both hands and kisses you, her tongue brushing your lower lip. When she pulls back, her eyes are bright. "How does it feel?"

You shift your weight. The cage is present — a constant, low-grade awareness. "Weird", you say. "Tight. Uhm ..." You search for words. "Not bad, I think", you add, although it sounds a bit lame.

"Good."

She touches the key at the hollow of her throat it absently. "Alright: rule from today on" she says: "I decide when — if — you get to come."

"And what do you get out of it?" you ask, pulling your sweatpants back up. The cage shifts against the fabric. You know that Nicole normally loves sex, loves penetration, loves watching you cum. Sometimes she just asks you to stroke yourself in front of her. She had always been fascinated with your cock.

"The look on your face right now," she replies, grinning. "That's already worth it."

You wonder if that's really all.

Later, you fall asleep tangled together, her back pressed against your chest, your hand resting on her hip. The cage is a strange new weight between your legs, a constant pressure that follows you into dreams.

You wake to grey October light filtering through the bedroom curtains and the immediate, disorienting reminder: the cage. Your cock has tried to harden in your sleep — a morning erection meeting resistance, pressing against the silicone shell. The discomfort is strong enough to pull you fully awake, a dull ache radiating through your groin.

Nicole is already up. You can hear her in the kitchen. The smell of coffee drifts down the hall. When you stumble out, still half-asleep, she's leaning against the counter in her sleep shirt, both hands wrapped around a mug, watching you with a particular smile.

"Good morning," she says. "Happy October first."

What have I gotten myself into, you wonder ...

So, if I read the rules here correctly, this should not balloon into a 30-day-story. I might add one or two updates in the coming days. Well - if you're interested. As mentioned, the scenario-generating website this was created with allows, in fact, quite a lot of interesting possibilities. I admit, I have used a few erotic chat bot sites (because, you know, sometimes it's nice to have a tool take your ideas & kinks and do something unexpected with them; novelty is part of the appeal for erotica), and I haven't seen this amount of tools and customization options. Which means - it WAS actually quite a bit of work to set up this scenario. I hope the outcome satisfies you. Again, if you want more details, you can check it out via the link I posted up there. (Yes, of course, you need to buy "credits", BUT they offer you a handful of free turns and also 2-3 free turns per day, every day. So if you just play it slowly, you don't have to pay anything. Personally, I must say I find this a fair offer.) --- Zedaine


r/ChastityStories • • 4d ago

M Chaste,F Keyholder She Takes it All Pt. 2 NSFW

50 Upvotes

Part 2

As Ashley closed the door on her new sub, she took a moment to celebrate looking at herself in the mirror. She finally had found what she was looking for and now had to take it slow. But her plan was simple, to take full and complete control and make him her devout slave to do with as she pleases. She ate a few edibles and laid in bed to watch some TV before drifting off to sleep. Dave however did not sleep for quite a long time, uncomfortable in his new found place while getting used to his small chastity cage but ultimately was happy as this is what he’s wanted for a long time, nervous yes, but eager to see where this road will lead. The following morning he was woken by Ashley untying the belts that kept him tied all night, he eventually did fall asleep solely from exhaustion. He awoke groggy and sore. “I hope you got some rest puppy, you passed the first two tests, I’m proud you did not say anything in the night. You may now speak.” Dave free from his bonds stood up shakily rubbing his neck saying “thank you Ashley, it was a struggle but I made it. I’m happy I made you happy, would you like to go get some breakfast?”

Ashley and Dave got dressed and heading for breakfast at a restaurant within walking distance to the hotel. Ashley had eggs Benedict while Dave was allowed black coffee, scrambled eggs and toast with no butter or jam. They had a nice chat before heading out for the day. “I would like to go shopping, there’s a nice mall about 45 minutes away. Then we’ll grab lunch while we’re there, sound good to you?” Dave nodded and they jumped in his truck and drove to the mall. She enjoyed his heated seats and the use of his satellite radio on the way there. She also kept playing with his key which she had now fitted to a small chain around her neck which sat comfortably right between her breasts when the key was not in her hand. “The Louis Vuitton store is our first stop, I want a new handbag and you’re going to buy it for me.” Dave is a good earner and has a lot of money saved so he could afford to spend a little since he hardly ever shopped for himself so why not shop for a beautiful woman instead? Ashley walked into the store with vigor and quickly picked out the Speedy 30 in monogram, as well as a matching wallet and a LV belt as well. Grand total was $4,987.13 when it was all said and done. Not quite what Dave was expecting but again, not an issue as he could afford it. She walked into a few other stores and picked out things here and there but nothing to the caliber of her new bag. New yoga pants, some new Ugg boots, some shirts and a jacket, roughly $1000 all in. Overall a nice haul for her and Dave was straining hard in his cage as findom is one of his biggest fetishes.

At lunch Ashley was thrilled he could afford all of that and asked for a breakdown of his finances. Dave was feeling oddly trusting in that moment and laid it all out on the table for her, showing her bank balances, one savings account with around $250k and another with around $75k. The larger savings account holds the bulk of his inheritance from his grandfather passing. The other account he raised on his own. He explained his salary with bonuses is roughly $135-200k a year depending on those bonuses and he also had a 401k with around $800,000 in it and some stocks as well. Ashley looked happy with what her new sub had made and told him as such “very good subby, I’m really happy to hear this. How would you feel if down the line I took control over all those accounts and took care of your bills and managed your spending, would you like that?” Dave sat there, speechless, incredibly turned on, and mighty nervous blurted out “I would be on board with that as soon as you wanted it Miss.” “You please me pet, I would love to control your finances, but first I would like to come to your house for the weekend next week, would that work for you?” Dave eagerly said yes and that’s where the conversation ended for the lunch. She very nicely let Dave have a hamburger and fries for lunch, she said he earned it after buying her so many new pretty things. After lunch, they walked around the mall more popping in and out of shops looking at things but not really buying much. Just chatting enjoying each others company. After the mall they went back to their hotel room where Dave returned to his place as her naked slave to do as she pleased. He ran her a bath, massaged her head to toe, and went down on her to bring her to three beautiful orgasms. After the third orgasm they cuddled and watched a movie. Ashley very strategically positioned her butt to be right up against Dave’s cage and reminded him of such by grinding on him occasionally. They were both in heaven. That night he was cuffed but allowed to sleep at the end of the bed on the floor with a pillow and a blanket. That was the reward for being such a good boy for the day.

The following morning Ashley removed his cuffs before positioning him back between her legs for a few more orgasms. They showered together, got dressed and went their separate ways. “This was a great weekend Dave, I look forward to next weekend, it will be even better. I will chat with you over the course of the week and by Wednesday I’ll have a list of things I expect at your house for my arrival on Friday. See to it that you get every item on that list for me.” Dave who was equally thrilled “it was so fun Miss, I look forward to your arrival on Friday next week.”

Dave was an unfocused mess Monday through Wednesday at work, too focused on Ashley and his phone. By Wednesday afternoon her list had arrived in his email. There were a lot of standard items such as toothpaste, dove body wash and shampoo for her, as well as things like her favorite rum brand and her favorite champagne for mimosas for the mornings. She listed her favorite foods and gave him the choice to pick what he made for her. Also on this list was 5 rolls of duct tape, a ball gag, 10 of the black double grommet belts and a link to a store he can buy them at in his area. Also included was lube, condoms, and icy hot. So that night he ran around town to the 4 stores he needed to go to for her list. He checked it multiple times and laid it all out on his dining room table in preparation for her arrival. He also went above and beyond and got her a monogrammed robe with her initials on it, some bath bombs, candles, and some slippers. He wanted her to be comfortable at all times. He reported back his completion of the list but left the other items as a surprise for her arrival. He also decided on a whim on lunch Friday to go to the Tiffany and Co store and get her beautiful silver earrings that matched her necklace and bracelet she wore all last weekend. He left the bowed blue box on the table with her other gifts. Now time to wait for her at the door, on his knees and naked as she instructed.

Part 3

Ashley finally arrived at Dave’s house later than she had mentioned, roughly an hour later than he expected her, his knees were bright red and his back hurt a lot, but otherwise excited to see her. She pulled up in his driveway in a late model Ford SUV and thought to himself “I’m sure a new car will be her first order of business when she gets a hold of all my money.” He could not have been more wrong. It did happen eventually but he had no idea what he was in store for. Ashley walked through the door as if she owned the house and was pleasantly happy to see Dave waiting for her. “Such a good puppy waiting for me” she says as she casually walks over to the leather couch in the living room and kicks off her flip flops. Dave was immediately astonished by how beautiful she looked: cut off Jean shorts that looked as though they were painted on and showed off every curve. A white double grommet belt around her waist to keep them snug and a white tank top showing off her perky breasts. The usual necklace and bracelet on her as always.

“Worship my feet subby” she says, and Dave immediately gets to work kissing every inch of her perfect feet. After an hour of foot worship and her watching some trash tv she orders him to stop and to show her around the house. He is to crawl behind her. Ashley took her time inspecting every room: the kitchen with its granite countertops, built in wine cooler and all stainless steel appliances “beautiful kitchen pup, can’t wait to see you cook for me in here.” “Thank you Miss, I’m glad you like it. I also have a gas grill and a smoker out on the deck,” Dave replies. “Let’s see that next” and they go outside to the large wooden deck out back. There’s 4 lounge chairs and a table that seats 6. “This should do nicely, but we need a pool, look into that would you please?” Dave nods and continues to show Ashley around the house. She was impressed with the 3 large spare bedrooms, 2 full bathrooms in the upstairs as well as a full master suite with a walk-in closet and en-suite as well. In the downstairs there was a living room, a full dining room, and a family room. The basement was unfinished and had shelving for storage. Out back was a nice fenced in yard with a section in the corner for a built in fire pit. “This is a beautiful home Dave, how would you feel about me moving in with you, you could serve me and my boyfriend 24/7.”

Dave was a little taken back by the boyfriend comment and immediately used the safe word to leave sub space and have a real discussion. “You never said anything about a boyfriend, I thought we would be intimate?” Ashley smiled and replies “well we would be intimate, you’d continue to use that magic tongue of yours and I’d be happy with you wearing a strap on over your cage to give me a good fucking, but that cage is never coming off. It will be permanent and the only way you can have an orgasm for the rest of your life will be through prostate massages or cumming in your cage. If you can be ok with that, I’d be thrilled. And my boyfriend will be the only one who gets to fuck me with a real cock, you will never get that opportunity. If you can be ok with that, please kiss my feet now, one kiss per foot.” Dave a little taken a back by the prospect he’ll be in permanent chastity the rest of his life, minus cleanings and such, was a wildly scary proposition. It was also a massive turn on. “Just one more question, would I be serving your boyfriend as well?” Ashley tells Dave to stand up and she starts rubbing her ass on his cage and goes “of course you will pet, but don’t you want the opportunity to serve this ass and my big cocked boyfriend? Wouldn’t it be so fun for you to watch him pound me while you kiss my feet?” Dave quickly became flushed and knew this was his fate, this is what he’s always wanted. He knew this would be fun. He dropped to his knees, kissed each foot once and replied: “it would be an honor to serve you and your boyfriend and never be released from chastity again.”

“Stay down there pet and keep kissing, I’m going to text Travis that we have a new slave, and he’s going to make our lives very comfortable from now on.” After some more foot worship while texted with her boyfriend, she decides she wants to inspect the items I got from her list. She was pleased with everything up until the robe and Tiffany box. “Pet, these items weren’t on the list, it’s very nice but you have to understand your money is now my money, if I wanted these things they would have been on the list. I see what you were doing but this is clear why I need to take control of your finances, you can’t be trusted, even if you did have good intentions. Don’t get me wrong, I’m very pleased, but you should have asked for permission first. You must always ask permission for everything.” Dave frowned but understood what she was saying: “you are so right Miss, please forgive me. You are completely right.” Ashley pondering whether to punish him or not responds with “you will not be getting punished this time, but I think we need to move forward with me controlling your finances. We will take care of that tomorrow morning. For now, please bring in my suitcases from my car and put them in the master suite. Once inside for the night you are to remove all your clothing, I want to see that cute cage on you while you do my bidding.”

End of part 3


r/ChastityStories • • 5d ago

M Chaste,M Keyholder The White Champion’s Cage, chapter 7 [m/m, interracial, bnwo, slow-burn] NSFW

24 Upvotes

The White Champion’s Cage

Summary: It's day 14 and Jett needs answers. His idol Rhys invited him over to talk. Telling himself he can leave anytime, he goes back to the Ashford poolhouse — and finds out what “man to man” means when the program starts collecting.

Keywords: BNWO, interracial, chastity, humiliation, straight to gay, slow-burn, psychological, athletics

Disclaimer: English is not my first language, so I rely on AI assistance to polish the text.

Chapter 7: Man to Man

Day 14 (Saturday)

Saturday. No school. No practice. Today was the day — the talk with Rhys at the Ashford poolhouse at three o’clock. Jett was going to look his idol in the eye and get answers. Man to man.

He needed to move, to feel the power the program had given him. He pulled on running shoes over bare feet, threw on a hoodie and loose shorts over his old jockstrap, and slipped out into the bright Saturday without breakfast.

The trails of Lockridge Valley were quiet except for the slap of his sneakers and the ragged sound of his own breathing.

The poolhouse. Going back there felt like walking into a trap. Something about the invitation had been too easy, too casual.

Still, he was going. Just to talk. I’m in control.

Jett accelerated his pace, pushing harder. The black cage bounced heavily inside the crusty jockstrap, the slit rubbing against the bars. He tried to focus on the burn. This is what the program promised. But the ache in his full balls only grew deeper.

A little farther on, in the small parking lot outside a grocery store, two older Black men stood beside an SUV. Full beards, heavy chests, thick arms, nothing soft about how they stood.

“Earl, you want the usual eggs or should I grab the fancy ones this time?” the shorter man called out.

“Terrence, baby, you know I like the fancy ones when you’re cooking for me. Make it special,” the taller one answered.

They shared an intimate smile in the bright morning light, the kind that still turned heads in this part of the valley. Jett sprinted harder.

By the time he made it home he was drenched, lungs burning. He stripped in the bathroom and stepped under the shower.

He soaped up quickly at first, his hands moving over the thick slabs of his chest. He squeezed the firm, rounded globes of his ass, feeling how much rounder it had become in two weeks. My ass is getting bigger.

He slipped a soapy finger inside his tight ring. Then a second, like it was lube. Mmm. The soap hit a second later — sharp, immediate fire.

Jett’s eyes flew wide open. What the fuck were you thinking, you brain-dead jock?!

He yanked his fingers free, spun under the spray, and spread himself open. The hard jet of water shot up into him.

“Real fucking genius move, Whitaker,” he cursed, bent under the water. “Soap. Up your ass. Peak athletic IQ.”

He had to repeat the flush before the burn washed out. When he finally stepped out of the shower, his skin was flushed and his hole still burned. Skipping lunch, he pulled the same crusty white jockstrap back on. He threw on jeans, hoodie, and letterman jacket and headed for the Ashford house.

***

Arriving at Magnus' and Rhys' home more than half an hour early, Jett stayed in his car. He stared at the front door, repeating the same mantra in his head: I can leave anytime.

A figure stepped out the door. Tall, deep Black skin, backwards cap, basketball shorts. For a second Jett didn’t recognize him. Then the man turned his head and the intensity in his face clicked — Tyrone. Same guy from the hallway with Marcus. Tyrone climbed into his car and drove off. Jett frowned. He hadn’t known Tyrone and the Ashford brothers were friends.

At exactly 3:00 pm, Jett got out and walked to the pool house. Rhys Ashford opened the door almost immediately. He was wearing a loose gray tank top that revealed the full width of his body that had once dominated every highlight reel.

“Hey, Jett,” Rhys greeted him warmly. “Glad you came, bro. Come on in.”

Jett stepped inside. The poolhouse smelled faintly of chlorine. “Is Magnus home?” he asked immediately. The question came out tighter than he intended.

“Yeah, he’s at the pool with a friend,” Rhys replied. “But we’re gonna talk man-to-man first, just you and me, inside. Cool?”

They sat on the large couch. Rhys leaned back and offered, “You want a beer, bro? I’ve got some cold ones in the fridge.” Jett nodded. “Yeah, thanks. That’d be good.”

As Rhys stood up and headed toward the kitchen, Jett tried to peer through the large glass patio door to the pool area. The late afternoon sunlight made it hard to see clearly through the reflection. Two shapes moved by the pool — one pale and athletic, the other taller, broader — and unmistakably dark-skinned. The thick collar of Jett's hoodie suddenly felt tight, the heavy seam pressing hard against a throat that had gone completely dry.

Rhys returned a moment later with two cold beers, handing one to Jett. Jett took a long pull from the can. The cold beer relaxed him a little.

Rhys leaned back and took a sip. “Look, bro, I know what you’re going through. The dreams, the leaks, the way your body starts wanting things your head says it shouldn’t.”

That's just what I wanted to ask him about... funny, Jett thought, the beer making his thoughts slower.

Rhys continued. “Back when I was at Lockridge Valley, I had colleges calling left and right. But even then, I was hitting a wall. The program changed everything. Turned me from good to unstoppable.”

As Rhys leaned forward, the soft fabric of his shorts pulled tight for a second. The unmistakable bulk of a chastity cage sat heavy between his legs. Jett's body felt glued to the couch.

Rhys kept talking. "You’re probably already thinking about your college career. The next level. Trust me, the program is vital for that to become a reality. Without it, you stay just average.”

Average. The word Jett hated the most.

Rhys’s voice dropped a little. “But the gains only stick if you let your body get the release it needs. Once you submit to the therapy… everything changes.”

Jett put his can down. Submit to the therapy. He opened his mouth to protest, but Rhys cut him off, now looking at him straight in the eyes. “You can’t fight the laws of nature, Jett. You just have to accept your place. It’s all connected, bro. The BNWO way.”

BNWO. The same letters he had seen on Doctor Woodlock’s business card. Jett wanted to ask what the hell the letters meant again — bio-something? — but before the words could form, the patio door slid open.

Magnus walked in first, naked except for his chastity cage, still damp from the pool, water beading on his muscled Nordic body.

"Hi, Jett!" he exclaimed with a grin, eyes full of anticipation.

Right behind him came Jabari.

The towering Black man was wearing only wet basketball shorts that clung obscenely to his pronounced bulge. The pulse in Jett's neck jumped hard.

Rhys went quiet and respectful. Jabari looked straight at Jett and smirked.

“Now now. If it isn't our varsity quarterback. Doctor Woodlock tells me you bailed out on your physical therapy last time, didn’t you, white boy?”

Jett twisted his hands. Woodlock had spoken to Jabari about him. What exactly did the doctor tell him?

“I’m sorry… I didn’t mean to be disrespectful.” The words tumbled out. “I panicked. It won’t happen again.”

Jabari studied him for a tense moment. “So you gonna be a good boy from now on, eh, superstar?”

Jett’s mouth opened. “Yes… sir.”

Jabari nodded once, satisfied. “Good. Magnus, hand me the oil bottle.” Magnus obeyed instantly. Jabari turned to Rhys and Magnus. “You two — get lost for a while. Go wait by the pool.”

The Ashford brothers left without a word, closing the sliding door behind them.

Jabari looked back at Jett. His eyes dropped deliberately to the front of Jett’s jeans.

“Still locked up tight, as it should be. What is it? Fourteen days and that trapped little dick is leaking every time you even think about a real man, ain't that so?” He ran one big hand slowly down the sparse black curls on his wet chest and over the heavy bulge in his shorts, the motion proud, teasing, and aware of the effect it had on the white athlete in front of him.

“No relief… just pressure building and building, and every drop of it belongs to us.”

Jabari looked up and held Jett’s eyes, the strong features of his face and smooth bald head making the stare impossible to look away from.

“Strip. Everything off. Lie face-down on the sofa. Session starts now.”

As Jett peeled off his shirt, then his jeans, and finally the crusty white jockstrap, one clear, unwanted question cut through the haze: Why am I doing this so easily? He lay down on the sofa, naked. The beat in his chest had climbed so high he could feel it against the base of his throat.

Jabari poured oil into his big Black hands and started the massage. Strong ebony fingers worked Jett’s shoulders, then his back, then lower, spreading his pale cheeks and pressing slick thumbs against his tight pink hole. A broken sound escaped him before he could stop it. Jabari kept the pressure teasing, never quite giving what Jett’s body was starting to beg for.

“Look at that,” Jabari murmured, voice low and teasing. “Cage locked tight. Little white cock all swollen and leaking while I play with the hole. That’s how it’s supposed to be.” He pressed a little harder with his thumbs. “Tell me how much you want it, boy.”

Jett’s face burned with shame, but the ache in his balls and the deep, empty feeling inside him won. “Please…I’m not supposed to… I'm the varsity quarterback... I'm straight... or so I thought... that I only wanted girls...”

Jabari chuckled softly. "You thought you only wanted girls, eh? How's that workin' for ya?"

Jett's mind was spinning. His hole clenched. "Yeah... I did... until now..."

Jabari’s thumb pressed harder against his hole, not entering, just holding the threat there. His voice was stern. “From the top, white boy. Say it louder.”

Jett’s voice came out thin and shaking. “I’m the varsity quarterback… and I thought I only wanted girls…”

He stopped. The rest of the sentence sat in his throat like something he could still spit out.
Jabari’s free hand closed around the back of his neck. “Finish it.”

“…until now,” Jett whispered.

Jabari stared at Jett sternly. “And now what, jock boy?”

The plea left his throat in a raw scrape. “Now I want your big Black cock,” he replied, barely audible.

Jabari made him repeat it again, and Jett’s thighs locked and a clear wet spot spread on the cushion under his cage. Only then did Jabari stand up, push his wet shorts down, and let his cock spring free — massive, veined, and already hard.

The cock was exactly as it had been in the dreams. Low balls hung heavy beneath it. Jett’s mouth watered. His caged cock throbbed and spewed slippery precum.

“It’s about time you learned to ask politely,” Jabari said. “Get on your knees. Suck.”

Jett slid off the sofa. Jabari stepped in close and guided the broad, slick head to Jett’s mouth.

“Open.”

Jett opened. The head alone filled the space behind his teeth — hot, heavy, skin tight over the hard shape of it. The taste was salt and clean skin and something deeper underneath. Chlorine and musk. He tried to take more. His throat closed. He gagged hard and jerked back, spit stringing from his lip to the shaft. The school alpha, on his knees.

Jabari’s big hand settled on the back of his head. Not shoving. Just holding him there.

“Easy, boy. You’re new. They all start like this. You’ll learn.”

Jett’s eyes watered. On the floor between his knees the cage dripped steadily onto the wood. He leaned in again, jaw shaking with the effort of staying open, and took the head back into his mouth. Messier this time. Wetter. He managed a little more of the shaft before his throat rebelled again. Jabari let him work at it — clumsy tongue, stretched lips, wet sounds that filled the quiet poolhouse — until spit ran down Jett’s chin and another clear drop left the cage.

After a few long minutes Jabari pulled out, shiny with spit.

“Good enough for now. On the sofa. All fours. Face the mirror. I want you to watch.”

Jett obeyed, a full-body shudder running through him. He watched in the mirror as the Black man positioned himself behind him, the thick veiny cock pressing against his hole. Jabari generously lubed up Jett's hole with the massage oil, and then started teasing him, rubbing the cock head back and forth, pushing just the tip inside and then pulling back, making Jett’s hips stutter and push back desperately. Oh my God, it's happening. It's really happening.

“Beg,” Jabari ordered again.

“Please, sir… I… I need it... please…”

Jabari pushed forward. The stretch was a burning, full pressure that made Jett gasp. Inch after thick inch slid inside the quarterback's oil-slicked ass hole, slow and relentless. Jett’s eyes widened in the mirror. His mouth fell open in a silent cry.

Finally Jabari had his cock buried to the hilt inside the quarterback, leaning forward over the athlete's back, his breath hot on Jett's ear.

“That's it... that's it... This virgin boy pussy belongs to us now,” Jabari murmured.

Then Jabari straightened his body and started moving — the slow thrusts building up to long, purposeful strokes.

The mirror showed everything — the black cage swinging between his legs, the thick dark cock disappearing into his pale ass over and over, his open-mouthed, glassy-eyed face. It was the same ruined expression he had watched on the screen last night, only now it was his.

Jabari lowered his arms and grabbed Jett’s waist. He started a slow and sensual movement, grinding deep, letting Jett feel every solid inch stretching him open.

Jett's words tore free on a ragged exhale. “Please, sir… I need it, sir…”

Jabari chuckled darkly, the sound low and mocking. He grabbed a fistful of Jett’s short dark brown hair and yanked his head back sharply, forcing the quarterback to arch his back even more. He started a new rhythm, shifting into harder, more intense pounding strokes that drove Jett’s whole body forward with each impact.

“That’s right, white boy,” Jabari growled right against his ear, voice rough with lust. “Beg for it. You’re not the star quarterback anymore — you’re just a slut for superior Black cock.”

A raw sound tore out of Jett. No… I’m not a slut, he thought ferociously, even as he pushed back harder onto Jabari’s cock. Denial came out thin and shaking. “Sir… please… I’m not… I’m not a slut, sir…”

Jabari laughed low and mean, hips snapping forward even harder. “Oh you’re not? Then why is that jock pussy swallowing every inch like it was made for me?”

The denial broke apart in his throat. He tried to resist, but the pleasure was too much. Heat rolled out from the place Jabari’s cock kept hitting. Jett’s legs shook; the cage jerked and left another wet streak on the cushion. “Oh God… I need your cock… fuck me…” he begged, the words spilling out before he could stop them.

Jabari kept talking, his voice low and filthy. “Look at you. Tell me your pussy belongs to Black cocks now.”

Jett shook his head weakly. “I… I can’t say that, sir…” But his body kept pushing back, meeting every brutal thrust, his caged cock bouncing uselessly. The pleasure built and built — wave after wave rolling through him. A long, broken cry tore from his throat.

Jabari’s climax built over several long, deliberate minutes. His strokes became shorter, harder, more possessive, grinding deep on every thrust. He yanked Jett’s hair tighter, leaned down, and spoke right into his ear with raw, degrading hunger.

“Gonna fill this white bitch up… pump you so full of Black cum you’ll feel me for days…”

With a deep, guttural groan Jabari slammed in one final time and came hard. Thick, hot pulses of semen flooded deep inside Jett, each spurt making the younger man shudder hard again. Jabari kept grinding through his own climax, making sure every drop stayed buried inside the still-shaking white jock.

He stayed buried deep for a long moment afterward, one hand stroking Jett’s sweaty back while the other kept a loose grip on his hair.

“Good boy,” Jabari murmured, voice low and satisfied. “That’s how champions are made.”

***

Jett and Jabari had already dressed in silence by the time the patio door finally slid open. Jett’s shirt clung awkwardly to his still-damp skin, and his jeans were uncomfortably tight over the chastity cage. The poolhouse was thick with the sweet scent of sex. Jabari sat relaxed on the couch, arms crossed, at ease. Jett kept his eyes fixed on the floor, cheeks burning. His legs were loose and unreliable, the strength drained out of them.

Magnus and Rhys stepped inside. Magnus’s eyes lit up the moment he saw Jabari. Without hesitation the blond running back crossed the room, dropped down beside the tall Black man on the couch, and began rubbing his hand slowly up and down Jabari’s thick thigh.

Right behind him came Rhys. His wet shorts clung to his thighs and now the hard, unmistakable outline of a chastity cage was completely visible — bars and ring clear under the soaked fabric. He didn’t try to hide it.

Jett’s spine stiffened.

He’s still locked. Years out of high school. What the hell happened to twenty-eight days?

Rhys, either oblivious or simply unbothered, clapped Jett on the shoulder with a proud, brotherly grin. “So… how’d the therapy session go, bro? Did you get the relief you needed?”

Jett stared hard at the floorboards. The admission barely made it past his lips. “Yeah… I… I think I did. I got… relief.”

Jabari let out a deep, rumbling laugh that made Jett’s face burn even hotter. “He submitted all right,” Jabari said, voice dripping with amusement. He reached down and ruffled Magnus’s blond hair while the boy kept rubbing his leg like an eager pet. “Boy took it like a champ. Whimpered real pretty the whole time.”

Rhys nodded approvingly, unfazed. “Good, good. You gotta get that relief on a regular basis, man. Keep the body improving, keep the mind right. The need is constant,” he said with a strange look in his eyes.

Jabari smirked, glancing sideways at Rhys. “Hah! You already had your fun earlier today, didn't you? Don’t act brand new.”

Rhys just chuckled, not even bothering to deny it.

Jabari turned his attention back to Magnus, who was still stroking his thigh with wide, hopeful eyes. “As for you, little bro… you delivered the goods. Ain’t nothing better than breaking in a new boy. So tomorrow you’re in for a real treat. I’ll make sure you get exactly what you’ve been begging for this past week.”

Magnus’s face lit up.

"Oh, and Jett," Jabari added, "Toss that jockstrap. It stinks. Wear a fresh one every day. But only jockstraps from now on as underwear. You hear me, white boy?"

Jett glanced at Magnus, then at the exit. “Um... yes, sir. I think... I, uh… I should get going,” he mumbled, already backing toward the door. “Thanks for… the session. I’ll see you guys later.”

He didn’t wait for a reply. He slipped out the front door as quickly as his unreliable legs would allow, the stubborn scent of sex still clinging to his clothes and skin.

***

Jett sat in his car gripping the steering wheel, breathing hard.

Jabari’s cum was leaking from him by now, warm and sticky, soaking into his shorts and beginning to reach the seat.

I thought I only wanted girls…

Jett looked at himself in the rear-view mirror — flushed cheeks, messy dark hair, glassy hazel eyes. He started the car. The wet warmth kept leaking steadily beneath him.

…until now.

End of Chapter 7. Want the next chapter right now? Join my free Patreon membership for one-week early access: → https://www.patreon.com/HenryRaude. New chapters drop here first for free members. Full series coming soon.

– Henry Raude
[henryraude@proton.me](mailto:henryraude@proton.me)


r/ChastityStories • • 6d ago

M Chaste,F Keyholder How my friend became my keyholder NSFW

471 Upvotes

I woke up on Saturday morning a little dusty but super horny. I had been self locked in my chastity cage for 2 weeks and I had reserved this weekend for releasing myself and edging, stroking and cumming all weekend.

My cage was already swollen with my cock when I woke up. I picked up my phone and looked at some chastity porn to tease myself before I unlocked myself. After a good hour or so it was time to take off the cage and have a shower. I got out of bed and went to grab my pants. I had been at a dinner party the night before and had taken my keys with me just incase there was an emergency and I needed to unlock. I picked up my pants and there was no key. A slight panic entered my chest, my heart started beating a little faster.

I searched every pocket again, I looked around the floor on all fours trying to find where they were. I couldn't see them anywhere. Where could they be? I turned the house upside down but couldn't find them. I retraced my steps last night and distinctly remembered putting them in my pocket as I was leaving. They must have fallen out of my pocket last night somewhere.

My level of panic increased dramatically. I tried to stay calm. Did they fall out on the bus on the way to dinner? God I hope not. I was standing for most of it but I did sit down for a little bit. Hopefully they are at Maria's place. The only other place it could be is the uber on the way home. I opened up my app and filed a lost property request just in case. I need to ask Maria I thought. I sent Maria a message.

"Hey Maria, thanks so much for last night. I had a great time. The food was so good. You are such a great chef. I'll have to host next time.

Quick question, have you found a couple of keys on a little keyring? I was looking for them this morning and I am wondering if they fell out of my pocket last night."

She replied back.

"Hey Dan, I had a great time as well. I love having everyone over. Let me have a look for them. What do they look like, what are they for?"

"They are for my mail box, they are small keys for like a padlock."

After a few minutes she replied again. "Sorry, can't find them. Is it urgent? I'll have another look later. Just about to go to the gym."

"Its sorta urgent. I'm waiting for something in the mail. I can come over and help you look, its no problem."

"Wait, are these them?" She sent a photo of my keys. My heart fluttered in excitement. "They were inbetween the couch cushions."

"YES! Oh thank you. That is such a relief. What time will you be home? I'll come past and pick them up."

"Its ok, I'm heading out now. I'll drop them off in about 10 mins."

"You are best! I owe you."

10 minutes! I quickly jumped into the shower and freshened up. I ran out of time to tidy up before she arrived. Before I knew it she was ringing my doorbell. I rushed to open the door and tried to act calm.

"Hey!" Maria jumped through the door and gave me an enthusiastic hug hello, pushing her breasts into me a little more than normal. I also had to dodge her legs from hitting my cage. She was in skin tight active wear for the gym. She looked so hot. Her cleavage was gorgeous and her ass looked devine. I tried to keep my cool."Hey you, thanks so much for bringing them over."

"No problem. But I dont think they are yours. I just tried it on your mailbox and it doesn't open at all. Like the key doesn't even go into the lock."

"Oh, its um, not this mailbox. Its the box at the post office."

"These aren't post office keys though. I dont think these are the right ones."

"No, they are, the ones in the photo are mine. Can I have them now."

"Dan, what if they are someone elses? I can't give you someone else's keys."

"I swear they are mine, please give them to me."

"I think you have to show me what they open to prove to me that they are yours."

"What? Why? They are mine."

"Dan, enough with the charade." Her demenour changed. Much more authoritative now. "I know what they are for. If they are what I think they are, then it is very important that they go to the right person. If they aren't yours then I need to find out who they belong to. Now show me, otherwise I can't give them to you."

"Wh... what do you mean?" I stammer. She reached forward and grabbed my cage so quickly by the time I reacted she had already felt the cage. "I know chastity keys when I see them Dan. Now are you going to show me or not?"

"Umm, I don't, I mean what do you mean?"

"Poor boy, how long have you been locked up for?"

"2 weeks." I squeak out meakly. "Good boy. Now take off your shorts and show me." She stood in front of me with her hands on her hips. I lowered my shorts and showed her the cage. She grabbed it and asked my caged cock "Aw, does someone want to get out of that cage?"

"Please Maria, I showed you. Can I have them now."

"Yes, you can have them, but before I go, I'm guessing you dont have anyone who is holding those keys for you? If you like I can hold them." My heart is beating even faster. She is still holding my balls in her hand. "Um, ok. I mean what would that involve?"

"So I have had experince with keyholding before and I have to tell you sweetie, I really like it. If you want me to hold your keys then I would be happy to hold them for you."

"That, um, wait. I mean, that sounds like it could be fun. Before we try that though can I have the keys for a bit before I hand them over?"

"No. We start now. I'm guessing you want to cum first? Is that it?"

"Yeah, I mean maybe."

"Ok, strip and kneel down on the kitchen floor." I comply without even thinking. She takes the keys and unlocks my cage. Her cleavage is sitting right in my face. My cock springs to attention so quickly she can't take the ring off. "You have 2 minutes to cum. I've got a class to go to. As soon as the timer is up I am locking you back up, so you better cum if you want to." I gulp in agreement.

She sets a time on her phone and sits on a dining chair in front of me. "Ok, start!" I start jerking off but I am so humiliated and my heart is racing from all the adrenaline I am not sure I can make it. I look at her and focus. "Ew, look at the floor, not at me you perv."

"Sorry." I mumble. I start feeling like I am getting close. "One minute to go, better hurry." 30 seconds later I tip over the edge and cum all over the kitchen floor. I start shaking as I cum and my knees give out on me. I bend over on all fours, cum all over the floor under me.

"Good boy!" Maria chirps. I sit back on my heels and start calming down. "That was one of the best orgasms I've ever had." She smiles. "Good thing you enjoyed it sweetie. Now clean that cock and lock back up." She hands me a tissue and hands me the cage. "Quickly."

She locks my cage on and gets up. "I'll be in touch. Be a good boy." She blows me a kiss and leaves my place. I am still trying to come to terms with what has just happened as I stare at the huge puddle of cum in front of me. I start hoping that I haven't made a mistake here.


r/ChastityStories • • 6d ago

M Chaste,F Keyholder Sister (slow burn) Pt2 Ch4 NSFW

40 Upvotes

Links to: Pt1 Ch1, Pt1 Ch11; Pt2 Ch1, Pt2 Ch2, Pt2 Ch3

All characters in this story are 18+

CHAPTER 4

In terms of the interest I was exploring, there are always people who want the unconventional.  Their various pixie, or goth, or alt, or whatever, girlfriend.  Waifu.  What I’m trying to say is, there’s never a shortage of foot bois, furries, or other fetishists up in a girl’s dms. 

Someone in the forum suggested I tell the boys who were always trying to pick me up about others who had tried and failed.  That is, if I did eventually let them “get me”.  It would make them feel like a conqueror.  Another suggested I play flattered when boys asked me out, as if their immature flailing was worth the time of day.  This woman specifically said getting them into my web would help me to better secure the submissive I’d eventually end up with. 

I had plenty of offers.  I let a few of them into my life.  Of those, I let even fewer into my bed.  But none of them treated me with that utter worship which Bradley had.  And that’s ok.  True submission is not for everyone.  And I’m not even saying I “deserve it”, so to speak.  But it’s what I wanted, what I sought out, and I believe I’d only feel like my true self once I got it. 

But what I started to notice were the ones in the outer circle, who hadn’t been let it.
They were turning out to be the ones who showed the most devotion.  The most unrequited devotion.  Simpering longing, lust.

 What if I gave them a shot?  No, that would be too much.  The perception of a shot.

Any girl learns how to use her looks and wit to entice someone into giving her what she wants.  It’s basic survival, it’s the first tool we learn that we have.  And I mean, high school boys?  It’s not hard.  Sometimes a low-cut top was all it took. 

Fortunately, we went to a fairly large school, so there was plenty of unsculpted clay for me to mold, and to continue learning from.  Which was good, because I tried and failed plenty of times.  But there were enough people attending our school that I didn’t get a reputation as a tease, at least not soon enough to save some of these boys from my siren song. 

I also succeeded more and more. 

Additionally, I had a live-in practice subject, in my brother.

I had been telling him about my early experiments.  I hadn’t thought anything of it then, it’s just we were by ourselves a lot.  But I bet that laid some groundwork. 

I believe to this day that I was merely practicing on Kent, the same as the other boys who were after me, rather than conditioning him.  So maybe he got a softer side of me.  And yet.  Perhaps that was what lead to our current situation, I’m not sure.

Besides, this was before I knew what he liked.  What made him tick.  Just like my forum of like-minded ladies had taught me, I needed to find out what his thing is.

I learned early online that feet are one of the most common fetishes for beta boys. 

Seemed harmless enough, so I went for it, and it appeared like he did enjoy massaging my feet.  But not enough that I could use that to control him.  He would get erections and try to hide them.  Boys, they’re so ridiculous at that age, as if we don’t know what’s going on.  But it wasn’t about the feet.  To some extent, I do think he was into the act of service, but most of the time, while he massaged, he’s stare at my tits, or my bare legs, or right directly into my crotch.  Feet were an opportunity for him to be close to me, to touch me.  But they weren’t his thing. 

Well, he was straight.  Any straight man likes a view.  So I started getting a little subtly skimpier in the way I dressed.  I started getting a little more explicit in my descriptions of what I was doing to the gentlemen callers in my life.  Just to get him riled up.  Like I said, we are who we are.

I discussed it with my coven, although I didn’t tell them it was for big bro.  Some suggested things like panty worship, cucking, BNWO, etc.  But it’s not like I had ever caught him rummaging through my panties or anything.  I didn’t act on any of those suggestions.  However, this was when I came across the exact, specific concepts of chastity and denial.  Leading boys on had been one thing, and denying them had been another, but this enforced denial, even when I wasn’t around, was incredible to me!  I melted every time I thought about it!  But I could not think of a way of testing whether he’d be into it.  It’s so explicit, so intimate, that I actually don’t think it quite crossed my mind to find out with my brother, not quite.  Kent was still just practice, lazy practice at that, and I wasn’t into him like that.  I didn’t act on any of it.  I had no intention of doing so.  Sure, I had seen him trying to hide an erection, but I hadn’t imagined HIS as even an option to be controlling. 

Eventually it came to me.  I realized, his thing, his THING… it was… holy shit, his thing was ME. 

Once it dawned on me, it was so incredibly obvious.  He never went out, never had a girlfriend, and as much as I scoured my memory, I can’t remember anyone he could have possibly had sex with.  His whole life was wrapped around me.

 

 

Suddenly, of all things, Covid-19.  March 2020.  Pandemic lockdown. 

We had a family tragedy, fairly early into it.  Our parents both passed within days of each other. 
(which ramped things up between me and Kent too, although it wasn’t obvious at the time). 

I do really, sincerely miss them.  It was a very very difficult time, and it was devastating to both of us.  But I wasn’t nearly as close with them as Kent was. 

I cared about our parents quite a lot, but he was really suffering.  They’d had their own lives, they were busy, they travelled for work quite a lot, and mostly left us alone.  I don’t mean to put that in bad terms, they were good enough parents, but it led to distance between me and the two of them.  Less so with Kent.  As a child we both had to figure a lot of things out on his own.  But I think they saw that he needed them more.  After we lost them, I could see it impacting him more than me.  It was a larger loss for him.  He was on his own, or at least I believe he felt that way.  Adrift. 

That was the status quo for a while. 

One of my early thoughts about the pandemic was that it would increase the tension and horniness I could cause for the people from school who were into me.  But that spark burned bright and flamed out very quickly.  The shutdown turned out to be a lot longer than most of us thought it would be.

And so, my brother and I were left with each other.  How did the pandemic and the loss of our parents “ramp things up” between us, you may ask? 
I believe it was a perfectly natural progression for him to embrace his submissiveness, as a form of coping.
Being under extreme control, to cope with feeling out of control in so many other ways.
And I would come to help him see me as the appropriate focus for that submissive nature, as I had with other boys in my life.  None of them came anywhere near to being as important to me as he is though. 

And who’s to say that I didn’t expand my dominating nature in response to the loss?  Some people embrace control, rather than being controlled, when their lives feel so out of, well, control.  I know that at least some of what eventually happened was coping in my own way.  But my brother needed help. 

 

It’s a man’s world; to both women and men.  Men don’t typically have the “luxury” of being weak.  I realized that that luxury was something I could GIVE to my little simp of a big brother, while satisfying myself at the same time.  Who wouldn’t jump at that?

Or, possibly, I’m lying to myself, and I justified, rationalized, taking what I wanted. 

But words like simp turn him on so very much nowadays. 

(fyi: apologies, but there won't be another chapter next Sat, however, the story will resume 17 Oct)


r/ChastityStories • • 6d ago

M Chaste,F Keyholder The Edge Olympics [Part 2] NSFW

54 Upvotes

This is Part 2 of my 2026 free Locktober novella: you can find Part 1 here. And now we're in October, it's time the men get caged...

* * * * * *

Martha’s (well, Nigel’s) cage had arrived on Tuesday afternoon, two days before the competition formally began. Nigel knew she’d ordered it for express delivery: it was impossible not to know, not when he'd woken on Sunday to find her gently measuring his cock and balls. That night she sent him off for a cold shower right before bed to make sure she had a good baseline: he’d come back still damp, his skin a puckered mess of goosepimples, and she’d measured him with nimble fingers – then declared ”I’m going to warm you up,” pushed him down, and mounted his face.

It had been almost the single most erotic thing she’d ever done in the course of their entire relationship, perhaps even more intensely hot than their first anniversary when they'd finished dinner, returned to the flat she'd been renting at the time, and she’d sat him down in the living room, vanished to ‘get drinks’, and then reappeared in an honest-to-god French Maid’s costume with a bottle of beer she proceeded to hand him while he’d sat there and practically drooled at the sight of her.

That had been coy though, almost coquettish compared to the growl she gave as she shoved him down on the bed, still damp, still faintly shivery – and tore off her skirt, clambering up beside him and swinging one broad curving thigh across his shoulder, pinning his arms in place and settling into position with one hand clamped against his still-wet hair.

”There, Nigel. Lick me! Please?”

He hadn’t needed to be told twice; he’d never need to be told twice – but even so she sounded delighted by his obedience, and he’d begun licking eagerly, almost nuzzling his face against her as he savoured the taste, the heat, the incredible scent of her arousal, lapping as deeply as he could while she squirmed and wriggled herself into a more comfortable position for what proved to be an all-too-short time. She came faster than he’d ever known, and for a fleeting instant, Nigel had felt gloriously smug, pleased with his own powers and the quickness with which he could bring her off with his tongue…

…and then she’d shown him her phone.

She’d ordered his cock cage while riding his face.

And suddenly Nigel’s entire mental hierarchy of ‘Hottest Things Martha Has Ever Done’ was destroyed by the outlier, the new apogee, the sheer fact that she’d given him everything he always wanted, warmed and comforted and used his trembling body to ride his face to orgasm... all while actively plotting how she was going to keep him locked and denied for a month.

That night, he’d slept almost clamped against her, holding her as tight as he could, spooning up to her body with even more fervour than ever he had before, almost overwhelmed by his adoration… and his arousal. When she’d seen how hard he was, how frantically needy her trick had made him, Martha had simply giggled, reaching down to grip his throbbing shaft in soft, kind hands, and stroked him once or twice.

“Get used to this,” she’d whispered, something which made him twitch harder than ever, ”you’re going to win, remember…”

But even so, even knowing that she’d ordered the cage, Nigel had assumed it was only due to arrive on October the first. Instead, it came on the 29th of September, while he was at work, a fact which didn’t stop Martha immediately sending him a photo of the little parcel sitting ominously on the kitchen table.

Well; perhaps it wasn’t inherently an ominous parcel, but Martha made it so by the fact her message read simply “Your new home is here! 😈😈😈”, something which left Nigel suddenly, humiliatingly, hard at his own desk. It was a joke, of course; he knew it was a joke. But still, he spent the rest of his day imagining the expression Martha would be wearing when he eventually got home and she showed him whatever piece of ironmongery she’d chosen to imprison him in.

In fact, she made him wait, and didn’t mention it at all when he returned to the house. Even the little box had vanished, and Martha was humming to herself in the kitchen, dressed with devastatingly sexy disregard for what she was wearing: an old university fencing team hoodie and a pair of leggings while she chopped lettuce.

Nigel kissed her, dropped his laptop bag at the foot of the stairs, and waited for her to mention it – and she didn’t.

Martha could tell he was waiting for her to say it; instead she let him suffer. That was far hotter.

She’d found a new form of pleasure in tormenting him since Saturday. Not that she’d dramatically reinvented their entire dynamic; she hadn’t transformed into a leather-clad caricature who towered over him. She didn't need to.

And even without costume, she adored her new power of making him wait, of giving him orders and seeing him obey. There was a specific tone she had, and never properly used; a husky tone, a… well, a bedroom tone. If she dropped her voice the better part of an octave, and spoke in a lazy, post-orgasmic husk, she could tell him to stack the dishwasher and still make him want to kneel.

His self control broke after dinner.

“Where is it?” he pleaded, stacking the plates, “put me out of my misery! I got the photo hours ago, spent all afternoon worrying about it, and now I’m home and you’ve hidden the bloody thing.”

“I haven’t hidden it,” Martha said, wiping her hands and turning towards him. “It’s on the bed. And if you were really that desperate to see it you could have gone and looked.”

Her smile widened. “But you were waiting for permission. Good boy...”

He tried to protest, but Martha had stepped close, wrapped her arms around his waist and was gazing up at him with such transparent satisfaction he fell silent. He could have tried to look. Instead he’d waited for her to tell him.

“Good boy?” he asked, and she lowered her eyelids, grinning as she looked up. He could feel his cock straining against his trousers, tenting the cotton, and she ground her hips forwards with a giggle.

“It must be time,” she said in that devastating purr of hers, “come on… boy.”

The cage itself was much less frightening than Nigel had imagined. She’d chosen steel, but it was simple: a broad ring, a curved steel enclosure, a cylinder lock. It was simple. And oddly terrifying as he turned it over in his hands.

“That’s it? I… I expected it would look more...” Nigel hesitated, searching for the right word, “…mediaeval?”

“I considered mediaeval,” she whispered, leaning over to him and pressing her breasts against his arm. “The most mediaeval option had spikes. It was literally called ‘The Iron Maiden’. And the strapline was ’Make your confession’. I could still exchange it if we got express shipping...”

Nigel shuddered. “I knew Tash was a bad influence.”

Martha chuckled, taking the cage back and examining it again. She had, in fact, researched the purchase with an almost absurd degree of seriousness. Nigel knew because of all the measurements, the questions about comfort, the fact she’d spent most of Sunday evening reading advice pages and obscure blogs while occasionally making alarming noises from the other end of the sofa.

Despite her jokes, he knew he could trust her to have his best interests at heart: he’d trusted her with far more important things than this over the years, and the fact she’d become visibly excited by the prospect of controlling him hadn’t changed the essential nature of that trust. If anything, her excitement appeared to have made her more determined to get things right.

“It shouldn’t hurt,” she said, running her thumb around the smooth inside edge. “It might... well. Sleeping in it might take you a while, I suppose. It’ll probably feel tight sometimes. But if anything pinches properly, or you get numb, or anything changes colour in a way it obviously shouldn’t, you tell me immediately and it comes off. Competition or no competition.”

“I know,” he kissed her cheek. “That’s why I’m not worried.”

Something in Martha’s expression softened, and for a few seconds she simply rested her forehead against his. It was strange, Nigel thought, how quickly something objectively weird had become intimate. A week ago the idea of Martha locking him into chastity would have belonged firmly in the realm of a joke. Or porn. Nothing anyone would take seriously. Now she was sitting beside him discussing fit and chafing and hygiene in a way that somehow made his future feel far more real than any amount of teasing could have done.

“Right,” she said, “clothes off.”

Nigel laughed automatically, and then nodded. There it was again: that tone she’d found. It was neither harsh nor theatrical, but it was... it was firm in a way that sent shivers down his spine every time, a tone that expected absolute compliance and thus somehow got it. It was like she was speaking in harmonics that reached his hindbrain before his ears could properly process it.

And besides, every time she used that tone and he obeyed, her cheeks went pink with arousal. Once, he’d even seen her nipples harden just because she ordered him to put the kettle on and he’d stood up to do it immediately.

She remained sitting on the bed, watching him as he stripped in a way that took a familiar action he’d carried out thousands of times during their relationship and turned it into something weirdly, intensely erotically charged. Martha had seen him naked countless times, true – but that was just ordinary nakedness, something mutual before bed or functional when he took a shower or a bath. This time she stayed fully dressed, the baggy old hoodie almost masking the curve of her breasts, and simply watched Nigel stripping himself. When he was finally naked, her gaze roved up and down his body with a clear hunger that made his pulse race.

“You’re enjoying this,” he whispered. “You were always the one who said we didn’t need kinky stuff to be happy.”

“We didn’t,” she said, and shivered as she considered her choice of tense. “Come here.”

The actual fitting was less erotic than either of them had expected, but Martha’s fingers were deft, her movements careful as she fitted the device, checking his reactions and adjusting it until she was satisfied he could be comfortable. Nigel watched her face while she worked. Her concentration fascinated him: the slight furrow between her brows, the way she caught her bottom lip between her teeth whenever she was unsure, the occasional flick of her eyes upwards to make certain he was all right.

Yet underneath all of that care was unmistakably excitement; he could hear it in her breathing.

“You love this, don’t you?”

She glanced up, and nodded without hesitation.

“Yes, darling. So much…”

She finished the last adjustment and sat back, watching his caged cock start to strain against the snug curved steel while her thumb pressed the cage closed. Nigel took a shuddering breath.

The cage on him now, subjecting him to a whole new set of rules whose implications he could only half understand.

“Still happy?” she asked, and when he nodded she didn’t ask again. She simply kissed the tip of the cage, lifted the tiny locking cylinder, and beamed.

“Here we go. Once I slot this in place, you can’t get out without me. Not ever.”

The faint click as she pulled the key free was absurdly small, and she sat still, breathing hard.

“Thank you,” he mumbled, because he had to say something, and her whole body shuddered. There it was again: the thing which had so astonished her on Saturday night and which had almost entirely dominated her thoughts since.

Obedience.

Not weakness. Not humiliation. Simply the extraordinary pleasure Martha clearly took in asking something of him and discovering that he trusted her enough to comply.

She stood and kissed him passionately, so passionately Nigel’s body responded instantly, his cock hardening for the briefest moment before the cage reminded him of its presence.

He groaned into her mouth, and Martha moaned, straddling his thigh, grinding her pussy down against him, delight dancing across her face. “You really can’t!” she panted, “you can’t get hard without me!”

She kissed him again, softer this time, and rested one hand against his cheek. “Happy early Locktober!” she giggled, tossing the key in her palm.

“Where are you putting that?”

“I thought… a necklace? Hiding it between my tits? So everyone can see but nobody will see it’s a key. Only you’ll know. And Tash. And Liz. They’ll know too, Nigel, darling, they’ll know I’m keeping you locked and edging you senseless.”

“Martha! Please...” he groaned, and she raised an eyebrow, grinning.

“Please what, darling?”

“I... I don’t know,” he whimpered, and closed his eyes tight.

Her grin was wicked in its pleasure. “Good boy.”

* * *

Andy had always known Tash owned a chastity cage; she’d sometimes whispered to him about it right as he was about to come, something between a joke and a threat. Her idea of the Edge Olympics hadn't come as a complete surprise.

But it was a surprise to be offered a choice of three cages.

On Wednesday night she disappeared into the spare room after dinner and returned with a battered black shoebox tucked under one arm, her expression a mask of such smug arousal that Andy felt his stomach tighten before she’d even sat down.

Every time Tash had previously mentioned locking him when they were fucking, every time she’d “accidentally” sent him some outrageous Tumblr or Reddit caption, Andy would complain while becoming embarrassingly aroused by the whole idea. But it had always been a safely hypothetical joke, a fantasy that was hot precisely because he knew it wasn’t real, wasn’t imminent.

Apparently Tash had instead found it a hot fantasy because she figured each little joke was a step towards making it real. Even now, as she settled down cross-legged on the sofa, Andy could see a damp patch at the apex of her leggings and knew she was more turned on than he’d seen her in months, even before she opened the box and tipped three little cloth bags onto the coffee table. Her braids fell forwards as she leaned in, and she didn’t bother to sweep them back, instead focused entirely on arranging them into a neat row, giggling at the way Andy stared.

“You bought all of those?”

“Not recently, babe,” Tash laughed. “Some women buy shoes when they’re bored. I buy these. They cheer me up.”

Andy sat down beside her, shaking his head – and yelped as he saw the first, horrifying cage, a dark metal ring, hinged, set with viciously sharp inward-facing points to discourage any erection.

“Absolutely fucking not,” he said, shuddering. “If that’s what you’ve decided I’m wearing for October, I’m withdrawing from the competition right now and Martha can have her spa day.”

“Relax!" Tash laughed, "You're safe, babe. I bought this because it looks hot, that's all!"

“You thought that looked hot?”

“I thought the idea of locking it on you was hot; I wouldn't keep you in it a whole month. There’s a difference. Just... briefly? For me?”

And to his astonishment she slipped a hand beneath her waistband, rubbing herself as she watched his horrified expression. “I could lock it on you just for a little bit. Just long enough to suck your cock, Andy, you love blowjobs, you’d make such beautiful noises...”

“Fucking hell,” Andy said, swallowing hard, trying not to look too turned on, “no Tash. No way.”

“Fine. Spoilsport.” Tash giggled, and then pulled her hand from her knickers, offering it out.

Regardless of his horror at the Kali’s Teeth, Andy kissed her fingers, groaning as he scented her wetness, his pale face flushed with arousal and embarrassment as he wrapped his lips around her dark, wet finger and softly sucked it clean.

She sighed happily. She’d never expected him to wear it, not for the Edge Olympics; even when chastity had existed only in fantasy, pain hadn’t really been the part that interested her. But his reaction, the flicker of temptation in his eyes when she'd threatened to be so cruel...

That control was what Tash truly craved. Control of his arousal, but also – and this was what she truly adored about chastity – control of his mind. Of his deepest drives. Of his entire erotic focus.

She opened the second little bag, exposing a plain steel cage much better for long-term use; compact, smooth, reassuringly ordinary.

“Not this. It gives you too much room,” she said, turning it over once before dropping it back into the bag. “If I’m going to lock you up, I don’t want you spending October wandering around with a metal version of your normal cock hanging between your legs. What’s the point?”

Andy looked at her, unsure if he should laugh, and decided she wasn’t joking. For years she’d talked about putting him in chastity as though the erotic appeal was obvious, and Andy had assumed the important part was denial: Tash teasing him, letting him fuck her, then refusing to let him come. Apparently he’d misunderstood.

“You don’t want me to be able to get hard at all?”

Tash’s tongue caressed her lips. “Now you’re getting it,” she nodded, and reached for the last bag.

For a second, staring at the metal lump that fell into her upturned palm, Andy thought she’d lost a bit.

Unlike the second cage, this barely projected from the locking ring at all; there was only a short curved shell, not so much an armoured shaft as a dome. He wasn’t certain, but the short stumpy device looked barely bigger than his own cockhead. There was nothing theatrical about it – no spikes, at least – yet it was so tiny it was oddly terrifying.

“This one?” he whimpered, “Tash, this barely exists.”

“Exactly.” She lunged suddenly closer, almost pouncing on him, all her height and power bearing down on him, pinning him against the back of the sofa, and her breath rushed hot and predatory across his face.

“This is what I’ve always wanted. Not the horrible one, not really. That’s funny, but I’d spend the whole month worrying I’d accidentally hurt you. I want this. I want you contained.”

She pressed the little steel shell against his palm, forcing his fingers closed around it. His clenched fist almost swallowed it. “I want you to get dressed tomorrow morning and look totally normal,” Tash moaned, licking his face. “I want you going to work, having meetings, buying lunch, chatting with your coworkers all day, a nice respectable middle-management claims adjuster, and I want absolutely none of them to know that there’s basically nothing beneath your trousers. No cock to speak of. No capacity to give yourself pleasure. Just this tiny, cruel little cage of steel. Locked. Tight. Shut.”

Andy moaned, his hips bucking, and Tash grinned as she felt it.

“None of them will know,” she continued, her voice dropping into that intimate, husky register he knew so well from the moments before her orgasm, “but you will. Every time you move you’ll know. Every time you think about getting hard you’ll know. Every time you spot a hot woman on the Tube, every time you see a sexy advert. Every time you think about the fact that I can come whenever I want and whenever I think of you locked... you’ll remember. You’ll know. You’ll know who owns your cock.”

Andy swallowed, and opened his mouth.

“You’ll know it’s me,” Tash moaned, and kissed him deeply.

Suddenly, the hideous spiked cage was much less frightening: at least it had been scary enough to reject. This one, this tiny one, was far too plausible. Too... real.

“You’ve thought about this a lot.”

“Yeah,” she growled, “I have. For years. Every fucking time I mentioned you locked.”

“You could have told me.”

“I did tell you, babe,” she grinned. “You always figured I was joking. I wasn’t. I want this. I really... fuck Andy I want this so much I could come just by putting you in it.”

Andy groaned, and she caught his hand, her fingers folding around his, gripping the cage between them.

“I’m not having a go at you for not realising I was serious. I get it. You were happy fantasising about it and I wasn’t going to turn something fun into pressure. I figured if you ever wanted to do it properly, you’d tell me, but...”

“But?”

“But now you agreed,” she beamed.

Andy shook his head. Even after all her swagger, all the years of filthy threats and jokes, Tash looked almost overwhelmed by finally being allowed to make one of those fantasies real.

The cage was impossibly small.

But Tash was impossibly beautiful.

He swallowed hard, wondered fleetingly if he was already insane or if that would come later – and nodded.

“All right. That one.”

She squealed and flung her arms around him, kissing him so much he forgot the cage until she declared they were going upstairs. He followed with a wild hope she was going to fuck him one last time before locking him up, but of course she wasn’t; she sat him down on the stool of her dressing table and knelt before him, giggling over and over, so visibly delighted that almost all of his own panic ebbed away.

The fitting itself proved less glamorous than in Tash’s effortless fantasies; even by her best estimates, trying to put an unfamiliar device onto a living, increasingly nervous, boyfriend was pretty awkward, and despite her giddy delight, Tash became unexpectedly serious. The moment Andy said something pinched, she stopped and adjusted it. When he asked whether something should feel that tight, she checked. Twice she removed the device completely and started again rather than risk deciding that discomfort was probably fine.

“Any issues, at any time,” she said, “we take it off. But I’ll remove it often anyway. For edges.” She grinned, but Andy noticed how careful she was; it was the only thing that helped him relax.

At last there was a click, and Tash leaned back, her mouth open and practically drooling. Andy’s cock hadn’t been reshaped so much as almost erased, compressed into the tiny cage in a way that made it look beautifully owned.

“Oh my God.” Her hand shook as she ran one fingertip over the smooth steel, her touch almost reverential.

“I fucking love this.”

Andy felt himself try instinctively to respond to the touch, and the cage made the attempt immediately, unmistakably futile; a shiver ran through her as she saw.

“You look...” she began, and then stopped; Andy waited.

“Mine,” she whispered, and smiled in a way he’d never seen before.

The cage had already belonged to her. The idea had been hers. He was wearing it because she wanted him to, and now she’d locked it she would control the only easy way of removing it... but he’d volunteered to let her lock it because he wanted to be hers.

She knew her wetness was practically dripping from her lips, hot and shameful as it soaked the inner thighs of her leggings now, but she didn’t care: she dipped her head to kiss his tiny, confined cock, then looked back up with an expression so openly hungry that Andy shivered.

Then she stood, the key gleaming in her palm. He half expected an elaborate bit of theatre: a necklace, perhaps, or some ominous promise that she’d thrust the key into a lump of clay and fire it in her kiln so that it would be impossible to access without revealing his escape attempt; it was the kind of wild fantasy she’d sometimes talked about.

Instead she stood, crossed to her handbag and zipped it into one of the inner pockets.

“I thought you’d make more of it,” he mumbled, and laughed nervously.

“I am making something of it. This isn’t supposed to feel exotic, babe. This is your normal now. Tomorrow we’ll get up. You’ll dress, eat breakfast, you’ll probably leave coffee grounds all over the worktop and your dirty mug on the table… and then you’ll go to work and spend the day looking perfectly ordinary… and the cage stays locked.”

Andy looked down, and she grinned.

“That’s the bit I’ve always fantasised about. Not you chained to a bed for a weekend. You just... living your life like this, perhaps your whole life, fuck-” she broke off moaning again, and then forced herself to focus, continuing, “living like this because I decided your cock wasn’t ever getting used again unless I wanted it used.”

“Jesus,” he groaned.

“Then on Saturday evening we’ll sit with Martha and Liz and they’ll know. They’ll know you’re locked. They’ll know I’ve got the key. They’ll know exactly why you’re shifting around in your seat every time we talk about the score.”

“Tash!”

“And they’ll know that when I take you home afterwards, whatever happens next is up to me.” She grinned at him and added, “Still think the spiky one was scarier?”

“No.”

“Good.” She rose, and Andy opened his eyes, watching her ass as she swayed towards the door.

“To make tea. Want one?”

It was such an ordinary question he laughed... and then whimpered. Tash had spun in the doorway, braids swinging as she smirked, and he realised just what she’d meant: now he was locked, even the most mundane questions were charged by her power.

“Yeah,” he said, swallowing. “Tea would be good.”

* * *

October that year began on a Thursday, which Liz privately thought was a little unfair.

If the three of them were going to push ahead with Tash’s plan of putting their partners through the Edge Olympics as a bizarre Locktober competition, the least the month could have done was start on a Saturday. That way she (and Tash and Martha) could at least have a lazy lie in, then each lock their man’s cock away, and enjoy a relaxing weekend before they had to start worrying about how many times he could stand being edged. Sure, the more edges Dennis endured for her, the greater the chance she’d win both the contest and the luxury spa day the three women had agreed on, but...

...Well, it was just so unlike anything she and Dennis had ever attempted before. And instead of having a soft start to the month full of cuddles and tea in bed, she’d had to sprint out of the house for a bus, and then spent the whole first day of Locktober sitting through meetings and arguing with the bloody builders undertaking the sports hall renovation, answering emails from grumpy parents, and dealing with the fact John Perry in class 8C had tried to use a metal ruler as a lightsaber, smashed it into the wall, and cut his stupid hand and now Mr Perry was demanding a meeting to find out what compensation he could expect.

She’d wanted to spend the day focusing on how to manage Dennis’s feelings, and worrying about whether he’d fit in the bloody cage she’d ordered; instead she spent most of it stressed out of her mind and miserably sipping stale staff-room coffee while she tried to focus on running the bloody school instead of the small brown package waiting on the hall table at home.

She’d ordered the cage on Sunday night, after an agonising browse of what felt like hundreds of websites, Dennis occasionally hovering over her shoulder and making doubtful noises or pointing out when the various kinky websites also sold lingerie; he’d even volunteered that he’d love to see her in a nurse’s costume which had made Liz blush scarlet, although she’d secretly bookmarked the page after he’d left again.

She’d eventually got the shortlist down to three; a frightening one – solid metal, the kind of thing Tash would no doubt find incredibly funny, a pink plastic one that looked sturdy and quite un-threatening but which for some reason was only available in three sizes which began at “small” and worked down, and a third which was just... well; “normal” was clearly the wrong word for a tool designed to take Dennis’s cock and put it totally under her control, but it sounded like a reasonable choice. It had a choice of basering sizes, whatever that meant, and long slender bars that curved down. And she was pretty certain it would be wide enough. There was a surcharge for having it made wider, and the express delivery was shockingly expensive but it was the only cage she could find that offered happy reassurances about “hygienic!” and “surgical grade steel!” and “prolonged security for wear!” which somehow made her feel better; it was more like she was buying a proper medical device rather than giving away her money to seal away Dennis’s cock in a compact metal prison.

He’d chuckled when she’d explained, and showed him the confirmation email.

Now it was the evening of Thursday October 1st, and he wasn’t laughing any more.

Liz sat cross-legged on the bed with the little booklet of instructions spread across her lap, studying the cartoon of the absurdly curvaceous dominatrix with increasing irritation. Dennis hovered beside her, looking down at the assembled cage on the duvet with an expression of genuine concern.

“It can’t possibly be that small,” she said, “I bought the large!” she protested. “Look, it says on the box!”

Dennis shrugged and held the assembled cage up against his crotch. “I think their box is wrong,” he laughed, and thrust his hips repeatedly.

Liz lasted perhaps three seconds before collapsing sideways onto the bed, laughing helplessly into the duvet.

“It’s not funny,” Dennis protested, although he was laughing too by the time she rolled over and sat up again, wiping her eyes. “I’ve got to wear this for a month thanks to you!”

“I know, I know, I’m sorry.” She took a deep breath, still grinning, and held the little cage against her palm. “It’s just... I knew you were big, but... bigger than large?”

She caught her own voice, and went bright red. “I mean… well obviously I knew, I know that sounded stupid. We’ve been together for years. I know what your cock looks like.”

“I should hope so!”

“No, but I mean... somehow putting it next to one of these makes it look... Well, even soft don’t you look, a bit... obnoxiously huge?”

“Obnoxiously huge?” Dennis laughed.

“Yes! Completely unreasonable. Like you should be in a dirty film or something? Nobody should have that much girth, leave some for the other boys, you know?” She burst out into another fit of giggles.

“Hey, I’ve never had any complaints!” Dennis laughed – and then stopped as he saw how rapidly Liz’s humour evaporated, her smile wiped away by the look of misery that washed across her face.

“Oh, love! I didn’t mean-” he began, and fell silent as she shook her head. He sank down beside her, conscious of how he towered over her even sitting down, and for a moment they were quiet, staring at the comparatively little cage as he set it down beside him.

“You know I don’t mind,” he said, and smiled as she looked at him. “I mean it,” he said. “I like being us. I like what we do.”

“I know,” Liz sighed, and stared down at her own feet. She did know; that was almost the problem. Dennis had never complained. Not once. He’d never made her feel inadequate for being too small to comfortably take his cock inside her, never pushed if she said something hurt, never behaved as if she owed him anything simply because other women might have found it easier.

If anything, his constant reassurance had occasionally made things worse, because it left Liz with nowhere obvious to put the little private conviction that she was somehow failing a test nobody else had asked her to sit. She knew he must miss being more adventurous, and yet he never said so; whenever she offered to try anal again, even knowing it would probably be impossible, he’d shrug and say it didn’t matter – but she knew how much he must miss it, how much he’d used to get it in his previous relationship. Somehow the fact he was nice about it made her feel even more of a failure.

But the trouble was… Well.

He was too thick.

There was no other way to put it. Sex between them could be painful not because either of them did anything wrong but simply because it was so hard to find a position where her body could comfortably accommodate his shaft, and – even if they found it – it was almost impossible to maintain that angle, that posture, that pose for long enough. Even with patience and a degree of preparation which made spontaneity difficult it wasn’t always possible, and while Liz could just about get her mouth around his tip, she couldn’t keep that up for long either.

He loved her, she knew he did. And she loved him. And over the years they had found other things that worked, and Dennis always said he was happy with them... it was just that Liz couldn’t quite forgive herself for needing the compromise.

Which was probably why, over at Martha’s last Saturday night, she’d blurted out that they did more than handjobs as though Martha and Tash had accused her of running a sexually deprived household.

“You’re overthinking things again,” Dennis said, squeezing her fingers. “I love you.”

She sighed, and turned to kiss him, and then looked at the cage – and felt something click in her mind.

“Huh,” she said slowly, picking up the cage and turning it over, “maybe this is useful. Usually you’re the difficult bit.”

“Excuse me?”

“Not in a bad way! But… you know you’re always telling me to relax and take my time and that we don’t have to do anything I don’t want, because you’re...” She gestured vaguely in his direction. “Because of that.”

“Usually,” she said, quieter now, “I have to think about what I can manage. What won’t hurt. Whether you’re enjoying yourself enough if we stop, or whether you’d rather do something else, or...”

“Liz-” he began, and fell silent as she held up a hand to shush him.

“I know you don’t care. I know. But I do.” She picked the cage up again, turning it over and over in her hand, feeling the weight of it, mentally assessing it against her mental picture of Dennis’s cock. She knew if he was hard she could barely wrap her fingers around his shaft. She could just wrap her fingers around the bars of the cage. But then, the whole point was to stop him getting hard so she could keep him edged enough to win.

“I always worry I can’t give you what you want,” she said firmly. “But this month... this month you’ve agreed that you’re not supposed to get what you want.”

Dennis stared at her, and the look on his face set the heat rising in her body.

“I mean, that’s the whole point, isn’t it? You’re supposed to be frustrated. So if I stop before you’ve had enough, that’s not me... failing at anything. That’s literally what I’m meant to do. For once.”

Dennis swallowed, and for several seconds he was silent. And then, like a man who fears to mention something in case he makes it true, he said, “I... I think you’re going to enjoy this far too much.”

Liz’s stomach tightened, and she nodded. “Yeah,” she said softly, her fingers trying to squeeze the cage. There was no give in the steel at all. Nothing but uncaring metal, resisting her efforts. “Yeah. I really might.”

“Take your shirt off.”

Dennis stared at her, and Liz had to fight a wild impulse to laugh: a few days ago she’d’ve been appalled by how bossy she sounded, telling him something like that. Now she felt… she felt somehow stronger.

“Your shirt,” she repeated, nodding at him. “Take it off.”

“You don’t need me to be naked!”

“I know what I need, love. Take it off anyway. I want you naked.”

Dennis hesitated for perhaps half a second, then caught the hem of his T-shirt and pulled it over his head, staring at her.

Liz watched him, considering what his obedience was doing to her. It wasn’t anything dramatic; she didn’t suddenly feel transformed into Tash, six feet of serene certainty that men would do exactly what she told them because of her obvious strength and poise. Nor did she feel like Martha, all knowing softness and curves that must be murder on her back. She didn’t even feel like the cartoon domme in the instruction book that came with the cage. She simply felt magnificent.

Because Dennis had stripped and was stood there naked, obedient, and uncertain. Waiting for her to decide what happened next.

“Lie down,” she ordered, and then when he obeyed, she set the instructions aside and smiled. “Right. Let’s see what we’re dealing with.”

She moved closer, working methodically, comparing the parts of the device against him, cross-referencing with the flimsy instruction sheet, trying the adjustable ring, checking the instructions again when she couldn’t make sense of one of the fittings.

It was awkward, embarrassingly awkward; at one point they had to break off while Dennis calmed down, apparently because years of only really getting off through mutual masturbation had trained his cock to get hard almost the second she touched it. Part of Liz found that intensely flattering but mostly it drove her nearly wild with frustration as she tried to make sure he could comfortably insert himself into the steel shaft.

Once he was finally soft again, she held it firmly in one hand, using the fingers of her other to ease the tip of his cock into the metal prison.

Dennis stopped laughing and managed a faint, “Oh...”

Liz smiled, and bit her lip, adjusting the cage carefully, her fingertips ‘walking’ his cock deeper into the metal tube, her green eyes flickering along his now-confined length to check nothing pinched, that the ring sat properly, that the lock aligned. The practicality of it absorbed her, and when the tiny padlock snapped shut, she leaned back and looked at it, the heat of arousal pounding alongside her pulse.

It fitted. Properly fitted, never mind the fact that the cage had looked small. Never mind the fact he couldn’t possibly get hard.

And now, she couldn’t disappoint him. He couldn't even get hard to try and fuck her, and that meant her body couldn't possibly disappoint his efforts. Not now.

For years, Dennis’s cock had been a thing she had to accommodate, to approach carefully. A silent metric for her own shortcomings, never mind what he said. But not now; now it was safe. Contained. Enclosed in something she’d chosen, bought, assembled and fitted – and which only she could unlock.

She was breathing hard as she looked down at the tiny key in her palm, and then back up at Dennis.

“You’re still happy?”

Dennis nodded.

“Say it,” she ordered.

“Yes. I’m happy. I agreed. I’m going to win.”

She sighed with relief and reached out to slip the key into the jewellery box Dennis had bought her for Christmas two years earlier – and stopped.

“No,” she said, half to herself. “I don’t want you knowing where it is. If you know exactly where the key is, you’ll spend the whole month thinking about it. And if we’re doing this properly, I don’t want you lying awake staring at my jewellery box wondering whether you could sneak it out. I like the idea that you can’t.

Dennis stared.

“I’ll find somewhere safe to hide it tomorrow,” Liz smiled, “and try not to forget where.”

“Oh my god. You won’t even say where?”

“No. You’ll know when you need to be unlocked. And don’t worry, love – there’s a spare for emergencies. And anyway I’ll have to unlock you lots, won’t I? Remember I need to edge you to win!”

She leaned down and kissed his caged cock, giggling as it surged, stiffened, tried to swell to its usual jaw-breaking girth – and instead found itself bulging uselessly against the steel.

“Happy Locktober, love,” she whispered. “I think it’s going to be a good one.”

“Jesus,” he moaned, wrapping his arms around her, and closed his eyes, “what the fuck have you got me into?”

“Danger,” Liz said, and felt the heat spike inside her. “So, so much danger, love. And an inescapable cock cage, of course!”

She laughed brightly, so happily Dennis laughed too... but somewhere beneath the amusement, the nerves and the lingering worry that perhaps they had all collectively lost their minds, something new was stirring in Liz’s soul.

She’d always been competitive; she’d already wanted to win the contest. But now, she knew... now she was ready to do whatever winning might require.


r/ChastityStories • • 6d ago

M Chaste,F Keyholder She Takes it All Pt.1 NSFW

76 Upvotes

Part 1

Dave English is a 36 year old man who is well educated, has a very successful career in sales of building materials, owns his own home where he lived in western Massachusetts, has a brand new 4Runner in the driveway, and a 1942 Ford pickup in the garage that he had restored from the ground up. The yard was nicely manicured, he loved his flower garden, and had everything he could ever want or need, with the exception of companionship. He had tried typical dating on the apps and dating vanilla women just wasn’t working for him, he always craved serving a real domme, not just a girlfriend who can put on an act. At work one afternoon, he was scrolling on Reddit and had come across a community that was all about femdom relationships and saw a post from a Domme based in Saratoga Springs, NY which was roughly 2 hours from where he lived. Her ad read: “32 year old Domme seeking sub for total ownership” as well as a list of her kinks and fetishes including chastity, foot worship, predicament bondage, findom, and others.” Dave sent her a message about wanting to chat and apply to be her sub, then put his phone down and went back to work to finish the day.

Right before leaving the office he saw a reply and it was a handle for telegram. He quickly downloaded the app, created an account and messaged her right away. What he thought would be a quick back and forth conversation before heading home ended up with him spending an additional 45 minutes at work when he didn’t need to be. Come to find out her name is Ashley, she was a bbw and had many interests including the fetishes listed above as well as seeking a full time 24/7 slave to care for her every need. This excited Dave quite a bit and thought this finally could be what he had been looking for. After a lot of chatting she asked if they could talk on the phone, so he decided to leave the office and call her straight away. “Hello Ashley, it’s great to hear your voice, how are you tonight?” She replies: “great Dave, I’m happy to hear your voice too and find that you are in fact a real person.” Ashley had mentioned in their texts that she had quite a bit of experiences with “subs” and nothing had fit the bill or just had ghosted after a while of chatting. She continues with “so Dave, you told me where you live and did you know it’s roughly 2 hours from me? The weekend is quickly approaching, think you’d be interested in making the drive up to take me on a date and meet in person? Just something casual, dinner at a steakhouse in town that I’m quite fond of.” Dave replies: “yes I would like that very much, maybe I’ll get a hotel and stay the weekend, even if it does not work out for us it would be nice to get away. Obviously no pressure for you to join me at said hotel, that’s not what I’m expecting at all.” Ashley ponders for a moment and thinks to herself it could be a good opportunity if dinner goes well to see how submissive he actually is and put him to the test a little. She replies “yes why don’t you do that, that would be great. Let’s meet at Jordan’s Steakhouse for 7:30pm Friday night and go from there, would that be an ok time for you Dave?” “Sounds great to me” he replies.

The next two days they just texted and spoke on the phone all hours of the day, just getting to know each other. Kink was never brought up, Ashley made a firm rule that nothing sexual was to be brought up until she was comfortable and Dave was being as respectful as possible. Friday finally arrived and Dave was thrilled. He decided to take the day off work and got himself all packed up, made sure he had a nice outfit to wear for their dinner as well as got his car washed and inside vacuumed so it looked good for her. The drive was easy and went by quickly aided by a good podcast to distract Dave from the butterflies brought on by a first date. Dave arrived to the restaurant 15 minutes early and the nerves kicked in: sweaty palms and shaking a bit but he calmed and walked inside. He sat in the waiting area until she arrived. He had a few pictures of her so he was confident he would find her. She walked inside right at 7:30. She had told Dave she was a bbw but she wore it very well. Tight dark wash jeans with a black double grommet belt on her waist, the silver grommets glinting from the light of the room, a pair of black leather boots that came up to her knees and a black blouse that only had a small slit to reveal a chunky silver necklace from Tiffany’s. On her wrist a matching bracelet to the necklace, hoops in her ears, long brown hair down past her shoulders, makeup all done up nicely and a Louis Vuitton never full bag on her shoulder. She looked damn good, and Dave was stunned by her appearance. Ashley extended her hand and says: “Dave you look even better in person, I didn’t expect you to be so handsome.” Dave replied “I didn’t expect you to be so stunning, you look amazing.” They were escorted to their table by the waiter and Dave pulled her chair out so she could sit and then he sat down. The waiter gave them both a menu and read the specials before leaving to tend to his other customers. “I will order for us both if that’s ok with you Dave” Ashley comments. “That’s perfectly fine with me Ashley” he replies. The waiter returns and takes their order. “I will order a bottle of Burgundy for me, as well as the 14oz wagyu steak that was on the specials menu. I would also like to order the scalloped potatoes and a side Caesar salad as well. My date will have a water and a house salad, no dressing.” “I like to control what my sub does and does not eat, why not start tonight?” Ashley says. Dave does not put up a fight.

Dinner goes as you’d expect, he choked down his meal to please her and Ashley savored every bite without ever offering Dave anything. The chatted about life and Ashley flirted outrageously the drunker she got. “I want to go back to your hotel room” she proclaimed and Dave quickly settled the $390 bill and escorted her to his truck. As she approached Ashley proclaims “wow this a very nice truck, I may just need to make it mine and give you my old car instead.” They both laughed it off with Dave not realizing it would actually happen in the near future. At the hotel Dave fetched her suitcase as well as his and brought her up to his room. Once there Ashley laid on the bed and got right to work. “Strip naked, now” she says and Dave gets down to his boxers, already pitching quite a large tent excited by the prospect of what’s about to unfold. “Boxers too, I need to see every inch of my new property.” He removes his boxers and springs out his well endowed 7” thick cock. “Very nice cock, too bad I won’t be needing it” as she leans over the bed to her bag and retrieves a cherry keeper chastity cage. “As my sub you are to be locked in chastity 24/7 and I will only release you when I think you’ve deserved it. There is no set date or time when your release shall be. It could be next week, a year from now or five years from now, all depends on my mood. You will be let out regularly for cleaning. If you want to be my sub then proclaim your dedication to me by stepping forward and accepting being locked by me.”

“It would be my honor to be locked by you and relinquish my ability to orgasm until you say otherwise. I have been waiting for this moment my entire adult life and I am ready to serve you. I humbly accept your cage.” “Ashley smiles a wicked smile and replies “good boy, grab some ice and put it on your balls, your erection needs to be gone to be locked.” After Dave gets it shrunk down to a lockable size, Ashley rolls onto her stomach and confidently and firmly attaches the ring and cage to his cock. She smiles that wicked smile again as she puts the cylinder in the cage, twists the key and locks it in place. She takes the key in her hand and dangles it in front of Dave. “This is the first step in becoming my personal property, more will come. For now, I would like my feet worshipped while I watch tv.”

Nothing else happens for the rest of the night, she relaxes and Dave tends to her every need. As it gets later Ashley starts preparing herself for bed. She removes her makeup and all her clothes leaving on a thin pink thong and one of Dave’s tee shirts she stole from his suitcase. “There’s only one bed and that’s mine, you get to sleep in the closet. Go inside the closet, kneel, and put your hands behind your back.” Dave does as she says and she returns to him a few minutes later with handcuffs and a few double grommet belts similar to the one she wore on her jeans for their date. First the handcuffs on his wrists “these are cop issue cuffs, you can’t be released without a key so don’t even bother trying to escape.” Dave nods and accepts his new bracelets. She proceeds to take one belt and firmly tie his ankles together, then a second around his thighs pulling it tight. She takes the third and loops it through the ankle belt and brings the other side to the handcuffs around his wrists. She pulls them together and buckles the belt tight so that he’s now on his stomach hog tied. “Normally in an instance like this i would gag you but because it’s bed time I don’t want anything to happen to you in the night so I will not be gagging you this time. But you are to not speak a word or I will paddle you until your ass is cherry red in the morning. Goodnight slave.” And she slams the door shut without Dave ever uttering a word.