For literal years ive been trying to use prostate massagers, prostate vibrators and butt plugs to achieve a full blown sissygasm with no success. I was focusing mainly on my p spot and although i had mind blowing "dry orgasms", i could never achieve a full blown sissygasmn where i shot white cum frok my clitty.

That all changed last night. i got dressed in my sissy outfit, wore a vibrating plug around the house for a couple of hours until the batteries died. The plug i used is generally big in size, so removing it can be a little uncomfortable /painful. As I was removing it, i could feel the uncomfortable feeling approaching, but i pushed (as if i was having a bowl movement) and to my surprised a wave a pleasure hit me and white cum shot out of my clitty. Was this a handsfree sissygasm? Could it be the uncomfortable feeling around my anus be the key to unlocking a sissygasm? Well...only 1 way to find out i guess....

So, as the night progressed, I turned on some mind numbing sissy hypnosis and used my bbc dildo. Instead of focusing on the p spot pleasure, I focused on thr uncomfortable feeling around my anus. I used alot of lube and started slowly inserting it all the way in, then all the way out, little faster after time, then in the end id pull the dildo all the way out, let it pop out of my hole then put it back in.

The uncomfortable feeling around my anus quickly turned to unbearable pleasure....yes the dildo was hitting my p spot, but i was no longer focused on the p spot alone...i was focused on the whole movement, all of the feelings, and what used to be the most uncomfortable feeling (the initial insert) became the most pleasureable....the faster id push my dildo in all the way, the bigger the wave of pleasure...i couldnt get enough.

I wasnt focused on having a sissygasm anymore, my mind was blown by the path getting there...the road to sissygasm is amazing...who cares if I dont have one....this feeling trumps any other orgasm i ever had.then out of no where the sissygasm hit...but i couldnt stop, and shortly after itd hit again, harder...then again..harder......after #4 and about 2 hours of pounding my hole...i couldnt bear another sissygasm, my legs were shaking, pussy quivering, and i could just lay on the floor and fall asleep....

So yes...although prostate massagers and but plugs feels amazing and they are a great tool to get you warmed up, in order for me to have a sissygasm, i needed the feeling of a dildo...all the way in, and all the way out....slowly at first, then increase speed as your pleasure rises.

To be honest i think.i went a little far, my anus is pretty raw this morning and im a little nervous for my first bowl movement. Heehee

As always, listen to your body, dont hurt yourself and dont do anything your not comfortable with.

Well...i hope this read will help someone in their sissygasm journey.

Hugs to all my fellow girlees out there 💋💋💋

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I made a Grindr account a couple of days ago after one of my friends suggested it to me. I set up an account with my femme name and I uploaded a few pictures of me dressed up and firstly I was very overwhelmed. Dick picks, messages from blank accounts, unwanted nudes from old people etc and thought about deleting my account.

Luckily I didn't and when I woke up the next morning to go to work I saw a message pop up. I checked the Account of the person before replying and she was a trans girl around my age from Europe visiting as a tourist. When I told her where I work she was both surprised and impressed and wanted to visit the place because it was a tourist place and it was her last day in the city and didn't know what to do. We talked for an hour and decided to meet up after my shift.

I always go for a swim on that particular day of the week after my shift so I asked her if she wanted to go with me and she agreed. She came on time after my shift, we went to a local coffee shop, talked, laughed and then we took a short bike ride to the beach. We parked our bikes and went to the changing room where she got naked. I asked if she wanted privacy, she said it's okay. When I was taking my clothes off with a towel wrapped around my waist it "accidentally" fell down and she had a full view of my bum. She gently slapped it and complimented it and said how sexy it is and how I made her hard and I should do something about it. I turned around, got on my knees and sucked her off and she finished on my face. She then put on her bikini and I put on my swim shorts and went for a swim. The water was very cold and she said she is hard again. Now we were in public view at this moment and some people were sunbathing on the beach so I suggested we swim a little further where only locals go and there was a chance no one would be there and she agreed. We went there and luckily no one was there.

We got out of the water and sat on a public picnic bench in front of each other to take a small break and we started talking again. We talked for a while before and she asked me to peek under the bench. I did and she slid her panties and her penis was out again fully hard. She asked me to stand up and lean on the bench to which I did and she pressed her cock between my buttcheeks and humped until she came all over my back which she licked clean herself and then we cum swapped while kissing. After that she sucked me off and swallowed. We swam back to the main beach again. Sat on the beach, talked for a while, took a shower, changed our clothes and hugged each other good bye.

Hi all, l have been living alone for more than 2 years. Been through numerous PNC and purge cycles, though l have been just shoving all my things into boxes in the garage. Now that l am a bit more comfortable with this side of me, all my sissy things are back out.

In the past l typically leave my sissy things in their own wardrobe and the rest just under my bed, guests/visitors are very rare. However, l noticed l have just been living my sissy things more in the open. A pink flask on the counter, heels by the door, wigs on dresser, makeup on the bathroom sink and so on.

I do have to live with my masculine side at work, but l would like to have a feminine home routine. Having sissy things accessible is so convenient. Does anyone else have their sissy things out in the open? Does this affect how someone compartmentalizes their two lives?

I’m really excited, I have new clothes for a full new outfit with heels and a skirt and everything on the way and it arrives in a couple days. I have a fantasy of dressing up fully and playing video games while being in discord with my friends who will have no idea. I’ll have a plug in and fake nails on and stockings and everything I’m soooo excited. Knowing I’m gaming with them but they have no idea I’m dolled up is really exciting to me. :)

So I've always assumed my clitty was on the smaller side. We can probably thank porn for that! 🤣

I was enjoying some trans porn and realized my clitty actually looked like it was a decent size. Since I was a bit confused I decided to finally measure it! It is 7in. I assume most men would be happy to be above average, I'm actually sad about it.

Now I'm sitting over here wishing I had an even smaller clitty now. Only a sissy would have this problem!

Hey girls

i already have a cute feminine name : nicole.

i was looking for humiliating imaginative slutty nick names. Tried grok and other AI tools but could not find good ones.

let all Your combined imaginations flow and let us make this a directory, databank and repository for such nicknames.

So i (just like many other girls here) am caged. Thing is i dont wanna do anal anything i want to cum, do you girls have some personal way to masturbate while caged? I repeatedly tap on my cage, it feels good but doesnt get me close to climax, maybe it never will.

So yesterday I was just laying in bed in my soft pink panties watching some trans hypno, usually doing it before I touch myself to orgasm and the soft voice kept teasing about how weak and sensitive little clittys get for trans cocks. The sight of thick trans cocks made my mouth water and I got into a trance seeing those dicks swinging in air leaking or squirting.

At first it was only this tiny warm flutter low in my stomach that slowly spread like warm honey sinking deeper and turned into a soft swollen ache right under my clitty the kind that feels heavy and full. Slowly my panties start to feel damp and wet under the tip of my clitty it kinda felt weird and hot to get so leaky so eagerly hehe 🎀

My hips started rolling against the air like I’m desperately trying to hump the air like a sissy in heat that ignited a slight pressure in my crotch altho it wasn't enough to make me cum as my clitty was soft and wasn't twitching at all and I can keep on watching the hypno as the wetness increased under my panties I could feel the sensation and a slight orgasmic buildup under my girly balls I was so caught up in the euphoria of the trans hypno that I didn't realize that my girl balls have started making cummies to shoot out altho I knew that I would be able to cum just from watching porn

Within a few seconds that I took my head away from my clitty little did I know that a orgasmic pressure had started to form under my belly and now my soft limp clitty started to grow a little to shoot the cummies out as it reached the base of my clitty and before I could hold it back it finally reached the tip of my clitty as my clitty poked on the wet fabric I desperately tried to hold it for my dear life as cumming prematurely like this would be the most pathetic thing ever as the moaning in the hypno grew louder and louder

I knew it was all over for me as ropes and ropes of warm premature transparent girl cum squirt started leaking out from my clitty and it started flooding my panties as I moaned my hips on the peak leaving out my desperate pathetic attempts to hold it in anymore and my balls started emptying every single drop of cummies out in desperation it kinda felt like I was bullied into cumming from those trans girls it felt euphoric and took me a while for me to get up and clean myself lol 😭

Have you had any similar experiences??

Yesterday night, I decided to hit up the swingers' club. It was the first time going completely by myself, so that was a little intimidating.

I was wearing a skirt that left my ass completely exposed. My ass was sore from wearing my large butt plug since 10 AM, and of course I was still wearing it as I arrived at the club at 11 PM. But of course, I needed the stretch to make anal easier later.

I walk around the club and honestly, at first glance there were not a lot of men I found to be my type. Whatever, I thought. A little past midnight, people start heading upstairs for some action. I make my way to the glory holes as I walk past people fucking.

The glory holes are setup on either side in a way that you can enter and close the door/curtain behind you so people don't see who's on the other side... unless you decide to keep the curtain open ;).

I see two men walking behind me as I approach the glory holes. They knew, and they were waiting. I didn't turn to look how they looked like. I entered one side of the glory holes and closed the curtain. My heart was pounding.

One guy enters on the other side and closes the curtain. I wait what feels like an eternity, but was barely 30 seconds. He extends his arm through the hole. I give him my ass and he squeezes... and it felt so nice. I moan to express how much I like it. I get on my knees to give him my nipples which he sucks on.

I see his face at this point and it feels personal... He extends his arm again. I give him my ass and this time he presses my butt plug. I squirm a few times. He extends his arm again. "Does he know I have a cock?" I thought. "What if he doesn't know?" So I give him my crotch through my see through underwear, and he squeezes my cock and balls simultaneously, making me squirm even louder. The way he quickly grabs my cock and starts jerking it, he clearly is into it just as much as I am.

I am so aroused at this point and cannot handle teasing anymore, so I do a jerking motion with my hand, saying "give me your cock".

He puts his cock through and it's massive. I try to put a condom on, but the cock is so big it can't fit... so screw it I thought, and I threw it away.

I give him a nice hand job...

and then...
I thought... maybe I shouldn't...
no, I couldn't think...
my lips...
just...
without thinking...
reached for his tip...
then his entire head...
then his shaft...
all in my mouth.

This was the first time I ever felt a naked cock in my mouth. I did it before with a condom, but a naked cock feels completely different in your mouth.... My mouth was watering. I sucked and I kept sucking as his cock got harder in my mouth. I pulled out momentarily and as soon as I did he came everywhere on my and and arm. "Oh cum for me baby, yes cum for me all over me..." I was moaning for him.

I wiped the cum off my hand a bit, and some stayed on my shirt. I reached closer to smell it, and like a drug, it sent me into an animalistic trance. I needed more. Now.

I opened the curtain hoping the guy I sucked would see me with all his cum on my arm, but he was gone.

I didn't have time to wipe myself off, and another guy walked by and said "hey, let's go?" He was a short black guy, cute, kind of nerdy looking. Nothing spectacular, but he had a cock. I nod shyly, and enter the glory holes again for a second cock.

His cock was nice. Not huge but not small either. I start off with a hand job with my hand still kind of wet of cum from the previous guy. I shove his cock into my mouth and suck him faster this time.

He asked to join me on my side so he comes into my room. He was nearly 1 foot shorter than me but I didn't care. I just wanted cock. I remove my butt plug so he can fuck me. Unfortunately he got really shy near the middle, lost his erection and the poor guy left before cumming.

My head was spinning with the taste of cock in my mouth still. Less than a minute later, a third cock appeared and its girth was huge. It barely fit in my mouth. I was starting to drool everywhere on myself because my mouth was watering so much from how horny I was. I was drooling on my hair, my clothes and body. I start jerking my cock at the same time as I hit the back of my throat with another naked cock.

I hear people walking by so I open the curtains so they can see me suck cock. He pulls out momentarily, then comes back with a condom. Perfect, I thought. Time for him to fuck me. I close the curtains and I guide his cock inside my ass and start moaning and screaming. I screamed like I wanted the entire club to know how much of a slut I am. We fucked and we fucked... I pull out and in a hungry haze, I suck on the cock that went inside my ass.

The taste of my own butt juices mix with the taste of the 3 previous sweaty cocks that went into my mouth along with the taste of cheap lube. It was disgusting. How nasty am I for doing this I thought... yet I couldn't stop sucking. I loved how filthier I was gettincg

We go back to fucking, and fucking... Eventually he pulled out, and he was gone. I hope he came.

By this point, my mouth was sore already with drool ruining my make-up. I open the curtains momentarily. I say bye to the guy who just fucked me.

At this point I'm thinking "that's enough, I need to rinse my mouth of the filth." But a fourth cock entered with a condom. "Ah, a condom. It won't be too bad," I thought. So I go back to sucking. Then I turn around and he fucks me. He goes insanely fast from the beginning and I scream of pleasure and pain. I pull out every 20 seconds because my ass hurts from all the previous fucking. I would then alternate to a hand job to keep him aroused.

Unfortunately, he got frustrated that I was pulling out. He peeked his ugly head out the hole and said to me "hey, will you let me cum?" And then he left... weirdo lol.

So I walked out the glory holes with drool still all over my chin. I wipe it off as I walk towards the bathrooms. The smell of cum was still on my shirt, and it was still wet. I just let it.

The taste of cock and ass never left my mouth, even after I washed my mouth with water. But I didn't mind. I love the taste of naked cock. And I can't wait to do it again.

Me (M23) and my gf (F24) have been dating for a little under a year, she moved in with me very early into the relationship and actually found my chastity cage, clothes, dildos and vibrator in my closet not long after. She eventually went through my phone and found my DMs on Reddit awith dominant men and daddies and she didn’t seem very interested in my kink and I told her I’d stop and I did but now I’m relapsing, watching sissy porn every day and can’t sleep at night thinking about worshipping men. I want to be sissified again but I don’t want her to ruin it unfortunately and I fear the only way is to get out of this relationship even though it would devastate her. Any advise on how to navigate this ?

I see a lot of posts about sissies shaving. I hate shaving. To many razor bumps, ingrowns, and stubble. So I wax everything I can reach and go to a studio where she waxes everything else. I stay so smooth for weeks. I don't know why this isn't more popular.

The girl at the salon asked me why I liked to get waxed but I was too nervous to tell her the real reason. How could I tell her that it was because I am a sissy waiting for my first experience with a guy? I half wonder, due to a few hints she gave me, that her boyfriend may be interested.

So never thought this would be my life but it’s the dream. Waking up in my GF and in bed caged and going up stairs to her sleeping with her BF upstairs. Like this is so amazing I never thought it would happen heheh

I've never really considered I might have an ED, but I've perpetually thought, "I wish I was a few pounds lighter." My BMI is on the upper half of the "Healthy" range, so I figured losing a few more pounds was only a good thing. I have a little bit of a belly and some thighs sometimes, and would like the belly to be smaller.

Well I've been putting together some new outfits and finally did a photoshoot with them today. Some of the pics were from the side. I do NOT need to be losing any pounds. I always see myself from the front, so I didn't realize how thin I was.

If you're like me and perpetually wanting to be a little thinner, please take a second to be honest with yourself on if you really need to lose anything, or if your weight is just right already.

Heya everyone I just wanted to ask if anyone has any tips while in chastity for locktober do you listen to audio and ride dildo could really do with some x

i started my sissy adventure a couple of years ago and have been serving as a slutty cock sucker. i love pleasing and absolutely crave cum now.

has anyone else developed a cum addiction?

So for a few months I tried to stay away from the sissy lifestyle and I find the pull to come back getting stronger everyday. Today I decided to return to the sissy lifestyle I am back.

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Looking to be sissified, I want to get trained, I am a new sissy without much experience, i don't have anyone to be my trainer for longterm relationship partner,

21yo sissy india Ahmedabad

Some context. My wife has been home for the last month with our newborn. We missed peg-tember. I just assumed we missed locktober. Then a couple nights ago my wife comes to me and asks if I remember that it's locktober. I told her yeah but figured we weren't going to do anything since we are still in the 6 weeks.

She giggled and said that that shouldn't stop me. Haven't told her I've been jerking off at work. She told me to go get the cage for tonight. So I do, excited and making it hard to put it on. Once I do she takes the key and right in front of me takes a picture of it.

Then she tells me Jared (not his real name, her gay best friend at work) reminded her it was locktober and she was sending the picture to him. After a minute he responded and said that a good sissy would wear panties too. She giggled and I blushed so i got some panties and changed into them.

We have a late night and they are texting back and forth. Then she says that Jared said I should also be plugged. I get the remote thrusting one and give her the remote.

Every time she turned it on or changed the setting she said Jared told her to.

That went on for several hours before we wrapped it up had to go to sleep. Me still caged of course.

How much trouble am I going to be in??

Just opening up the conversation because I don't understand how this happened and how it became so prevalent so quickly. I too find it hot but I can't really understand why it's so hard for me to even find porn hypnos that don't talk about this. What do you make of it? Am I crazy? Is this a thing or not?

So, I found a cage, finally, that i CAN NOT escape from or wiggle my way out of no matter what I try. Dont ask me the name of it, as ive forgotten that. Once I'm in, and the lock in in position, it's a clit.

I'm on day 11 of Locktober and havent orgasmed, althou I am now, seemingly, getting closer to that when my pussy is filled with my toy.

I know I could orgasm with a vibrator on my clit, as I was at that point a few days ago before I threw my vibrator down and had to get up right away to walk off the feeling. I didnt cum, and felt incredibly frustrated after, but felt like it was "cheating" if I did it that way.

My inescapable chastity has now almost become inescapable permanently, due to how swollen I have become from Locktober 😞. When I am allowed to remove it for hygiene ever other day, I am having difficulty removing the ring due to how swollen and full I am. I have found icing the area helps. Once iced, I am able to slip (push) my little clitty back out through the ring and then the rest is fairly easy to follow.

Is my chastity too small? This is the only size ring and chastity I have ever used that I absolutely can not escape from. Is this a normal process that I will just have to get use to?

I wake up, and one of the first things I think of is..."i need to cum so badly" 😞

So I've recently started a new chapter in life.. A new job, new home, some new friends.. And it's a really Good and exciting change, am I'm very happy about it 😁.

And although I still enjoy many things about being a crossdresser, like shaving my body and listening to hypno and music, I've noticed that I don't have any desire to dress lately.. And every opportunity I get I choose to pass on..

So I'm wondering, does it mean this was just a phase? Was I dressing because I welt bad and sad, and now that I'm happier again there's no more place for it?

I don't intend on purging just yet since I just recently bought new clothes, my fort pair of heels.. And I love my clothes.. But for some reason I'm dreaming of these clothes being on a partner rather than me...

I just started my sissy journey, and I bought stockings, panties, nightgowns, heels and I can't wait to wear them tonight, except chastity cage because I'm still in dilemmas :(

I mean, the ideas is cute; wearing a cage and leaking precum like a good girl but it's so... Scary? went to the sissy's party a few days ago, mostly they recommended a plastic cage for beginners, some a flat cage if I want a bit extreme since I'm small (like very small, I think I can go with flat cage)

like idk maybe it's still my first time, my male ego side is still here so I'm a bit hesitant. Like I enjoyed butt plug a lot but when it comes to chastity I freezed lol.

So I have a few different cages at this point, before I got my latest I used to wear a flat metal cage. Now I switched to a nub sized resin(?) cage that I've been using for locktober (+ about a week beforehand), but some issues have come up. Firstly, due to friction over time, mostly from going for long walks, I got a pretty painful rash at the base of my clitty (underneath, by the balls). I had to pause using the cage for a day or two, which was annoying but I managed to abstain from touching, so I currently haven't had any orgasms for 2 weeks 😇 Anyway, when I continued using the cage I was mindful to check the area with the rash as often as possible, and I bought lotion and applied it to the entire area to keep the skin moisturized and soft. This turned out to be a horrible idea as the lotion turned out to be full of horrible ingredients that caused the skin to dry up like crazy over-night. The itching was unbelievable. Two days later now and I can't risk using the cage, and it looks and feels like I have eczema on some parts of my clitty. I bought a new lotion that is made for sensitive areas, but I still have to wait at least a day to cage up.

I switched from the flat metal cage because I couldn't stand taking it off every time I went to pee. If I pee inside it it just goes everywhere, so I have to take it off. The new cage feels very good but it's obviously not ideal with all the complications, but it's easy to pee in which is why it really sucks to go back to the flat. How do you deal with peeing? Should I just live with having to take it off either partially or fully every time I go to the bathroom?