r/SissyConfessionBooth

So this happened when I was 24. By this time I was already well versed in sissyhood.

I had a collection of outfits, lingerie, wigs. I kept my body shaved when I was able to (mainly in the colder months since I would wear pants more often in my day to day).

While my normal weekdays didn't deviate from my life too bad (mainly some minor dressing and teasing online). The weekends were my playtime.

Normally Friday after work I would go home, get changed into a cute outfit I picked out the night before and spend time solo.

Saturdays were the days I went out. Sometimes it was to a CD friendly gay bar. Those nights normally ended in me blowing a guy in his car or being bent over his truck. Sometimes I went to an ABS after hours. More than a few times I would spend the day on Grindr to arrange some nighttime fun.

There I was still sitting in my boy clothes at like 2pm. Just checking out my profile, seeing who was looking good. Eventually I get chatting with a nice looking guy. Early 40s, BWC (least 7 inches), hairy and tall (I average around 5 '7 in flats, 5' 10 in heels) he was at least 6 '2. (He will be referred to as James going forward)

We start chatting, im being playful by sending him photos and a little teasing. He responds by saying he wants to meet at his place later that night. I agree and show him a few outfits and ask what he wants me to wear. I believe it was between a school girl outfit (blouse, skirt, stockings,heels) a housewife getup ( 50s style dress, leggings, a little more makeup) or a “slut” outfit (miniskirt, fishnets, pumps). He ask for the housewife (my personal favorite). He send me his address (about 15 min away) and we set the arrival for a little after dark around 830.

I start getting everything ready around 6pm. Gives me 2 hours to get decent. I just hop out of the bath when I see a message from James. Asking me if I mind a change. He was going to have a buddy stop by for a bit tonight. His buddy, and him, are on the DL ( I learned after arriving that he was MARRIED with KIDS). He said we can reschedule OR when he arrives I can sneak off to another room since it will only be a few minutes. At this point Im already prepping and horny that I dont want cancel. I agree to hide, IF he knows what time he was going to arrive. He said he was going to arrive around 9 so we will pause then.

Perfect!

By the time I finish everything, I am sliding on my black heels and fixed a perfect red head wig (think a MUCH SMALLER version of PAM from Married with Children). Even added a little bandana to complete the illusion. I wrap a coat around myself and get into my car.

I arrive at a nice little suburban house and I see porch lights. It's 8: 30 and I text him saying I'm outside. He said the door is unlocked to just come in. So after taking a deep breath I walk up and open the door.

THE FUN:

I get there and he greets me at the door. He says I look lovely and I do a little spin and a curtsey.

I put my purse down (filled with lube and condoms in case he wasn't clean) and came over to him. I put my arms around him. Telling him it feels good to come home to a big strong man.

He offers me some wine and I sit on the couch in my best “knees together good girl” position. After taking a few sips I ask him what he wants to do?

He leans over and starts making out on top of me and I am just going with it. I feel him grope my breast (padding) as my hands slowly make thier way down his pants.

Eventually I get to the bulge and it feels so HUGE!. I ask if he wants me to take care of this? He backs off a bit and undoes his belt. I slide to my knees and fish out one of the biggest WHITE dicks ive seen. I make sure my hair isnt in the way. Give it few tugs and a lick for good measure. I do my best to take it as deep as possible and I see his head lean back and his hand goes on my head. I take that as my sign he likes it.

I am about 10 min in and was gonna end it soon (i came for this in my ass) then…We both shoot up as we hear the door. We lost track of time and when we looked at the clock it was 9:10. In walks his buddy (“Mark)”. About as tall as him, little darker skin, not bad looking.

He came in saying “Hey man, sorry im late, I just wanted to see if you had…” There was at leas 15 seconds of silence as I sit there with James’ cock in my hand. He starts laughing asking if he was interrupting. James plays it off saying that I was just a sissy (clearly not his first). Then he does something that would normally be a turn off, but I went with it.

“ You want a go at her?”

There he was, a man I just met offering me up. I should of been mad…but I was just turned on. I let go of James and put my knees together and in my best femme voice “Id be happy to help you”

Mark gets over to me and slides his pants down. His cock is roughly the same size of James and,unlike him, not as gentle. As soon as the pants are off he guides me to his cock and I swallow it like I'm expected to. I spend a good 5 mins getting throat fucked, All while James is jacking off.

James gets up and starts pawing my ass a bit. I extend it out to let him and he ask if im ok with sharing. I nod and Mark lets me breath.

I get my arms up on the couch and extend my ass. I tell them there is lube in my purse. Before I know it, the shirts are off and I have 2 naked men in front of me. James lubes himself and is generous. I slide off my black thong and he applies it to me. At this point I'm all in “Yes daddy, I need your married cock inside me!”

Suddenly he enters me and after a few seconds to adjust, starts going hard. I start moaning, all while my cage is clicking against me. Mark gets on the couch and places his dick right in front of me. I go off instinct and take it.

“Let me see those titties!” He undoes the buttons on the top of my dress to expose my bra, rips of my bandana on my hair, all while I'm getting railed.

I'm lost the moment I don't look at his face. I did not see him take his phone out. He starts recording it.

They are both laughing, im getting some light smacks on my ass and face and start talking dirty.

“Whos our good little girl?” “I am! I am daddy, fuck your little girl!!!”

They both pull out and guide me back on my knees. THey start jerking it in front of me and I know what to do. I open my mouth and start begging for it. Before I know it 2 hot loads of thick cum are draping down my face and clothes.

When they finish I jerk them both a bit for good measure as they sit on the couch. After a little rest, I get my shoes, bandana and purse. I tell them I need my beauty sleep and I had a lot of fun. James gets up and walks me to the door. He said he feels stupid for not checking the time. I tell him it was fine and I had fun. Mark ask if he can have my number for the future. I agree and sign it Jenny with a little heart.

I tell them both I had fun and would love to repeat this.

I button my top up a bit and walk to my car.

When I get home I basically pass out as soon I get to my bed, still in my dress covered in cum.

Only after did I remember the video. I decide its not worth making a snuff over since no one knows who I am. But its probably still out there. Maybe online? Shared between his friends? I never did see them again so who knows.

Fun to think one day my wife (married years later) may find it lol

Im returning after having purged some time ago. For context fell victim to a scammer and in the resulting mayham purged everything with the exception of my panties and 2 plugs. Am being cautious and trying slowly get comfortable with things again. Looking at some dildos at the moment to get to replace my lost one. Any got any suggestions for someone who is on a restart? Any suggestions from lingerie to toys to things to do would be appreciated. Unfortunately i wasnt able to get that far into it before so knowledge is limited.

I was dating a sissy a few months ago. She was locked and loved dressing in a wedding dress. I was at the start thinking this is odd but I fell in love with sissy wife's it's so hot. A sexy sissy locked and horny is so sexy

I was a completely straight guy in my teen years, but around 16 I started watching porn more often then not and for some reason I always watched the guy and the cock instead of the girl, and I always timed my ejaculations to when the guy on screen would cum.

Skip ahead about a year later and I downloaded grindr (I know I was young but who hasn't downloaded a dating site at around that age) anywho I found a guy and talked to him for abit, he sent me some dick pics and he was abit small but hey this was the first guy to give me attention, I wanted to meet up with him but got scared (to young, might be trouble, could be dangerous) so I backed out.

About a year later when I was 18 I decided to try again, this time I wanted to be a top, I was very back and forth on what I liked and at that time I wanted a top, me and the same guy still talked so I told him to go down to the park and I'll meet him.

About 20 mins later I walk down there and he says "you can jump in if you want then you can fuck me" I said "um actually if it's okay I won't jump In your car, for safety" he didn't mind so I pulled my cock out and he sucked my cock through the car window...in pure daylight...midday haha, and there were a bunch of houses who could have seen me.

Edit: it's wrong but I was 18 he was 64

After that first time I liked it, but then the thought of having cock turned me on more, I got more and more adventurous, looking for cocks to suck and take till eventually I found someone who was nearby, I couldn't host and neither could he, we thought we were at a block, then he told me to meet him down the end of my road, I did and he picked me up.

I thought fuck he is hot and started sliding my hand up and down his cock while he drove, we didn't drive far, we found this open but in night private spot at a tree next to the highway, we kissed and made out for abit then he said "drop to your knees slut" fuck I was weak and did as he said, he pulled his cock out and holy FUUUCK, about 7.5 inches and girthy as fuck, I could barely take it but I told him to force it in me, he grabbed the back of my head and rammed his cock down mu throat, eyes went into the back of my head and I was slobbering, I loved the taste I love the sound I loved every inch of it in my mouth.

After about 10 mins (felt like an hour) of throat fucking he told me to stand up and take my pants off, again I did as he said, now I had played with my toy but I had never taken actual cock in my ass so I was tight, he spit on his cock and then rimmed my ass, I came a little on the tree, then he stood back up and I felt the head go in and I screamed, he grabbed my mouth and told me to be quite, as he said that though he pushed his cock in deeper and omg I just melted.

I pushed back on his cock like I automatically knew what I was doing, he grabbed my waist and pounded my asshole till I couldn't take it anymore, which was about 45 mins of straight doggystyle, I whimpered and groaned, but I loved every minute of it, he grabbed my throat and said he was about to cum, with a raspy voice I said "cum in me daddy, cum in your little slut" and boom I felt every rope of cum full my insides, he pulled out and ahoved 2 fingers in me pulled them out and showed me his cum covered finger "oh wow daddy that was a big load" I said as I licked it off

He dropped me back home and said "see you in a few weeks baby" now whenever I can I try to take his cock and be his slut, but nothing will ever beat that first time at the tree with him and that's when I decided to become a sissy

I’ve been doing this for a few months now whenever I’m horny: I worship men through a homemade gloryhole setup at my place.
And the demand has honestly been insane.

I attached a curtain in the doorway between my hallway and kitchen. The guy comes in, gets his privacy, takes his time getting undressed, sits down, and slides the chair through the curtain so that his lower body is on my side.

They’re allowed to be demanding, bratty, selfish - to just indulge themselves. Like it’s their birthday, but completely sexual.

I put a lot of effort into the whole setting too: the bathroom is fully available, showering or bathing, both are an option, and if he wants, I’ll even run a bath beforehand. I set up drinks and snacks in the hallway, keep the lighting dim, use incense, and play music that fits his taste. I want him to feel welcome, relaxed, and cared for from the very first second.

And when he’s finished, it doesn’t just abruptly end there. I clean him up with a warm towel, let him come down, and he can relax for as long as he wants before getting dressed and leaving.

That’s exactly what I’m into: I want to be a safe space for men where they can completely let go and just be serviced.

The feedback so far has been extremely good, but it still doesn’t feel like enough to me. I want to make the experience even more intense, hotter, more indulgent, and more unforgettable for the men who come over.

What details would take an experience like this to a completely different level? Service, experience, atmosphere, anything.

What are men really into when it comes to an anonymous worship/service setup like this?
What makes it hotter, more luxurious, more memorable?

I’d really love to hear your ideas.🩷🩷

About 5 years ago, I was taking a work trip and driving to another state. It was around 1pm, and I needed to go to the bathroom and noticed there was a rest stop on the next exit. I exited and parked, but before heading out I was cautious of who might be outside due to the fact that it was late and dark. I noticed the only cars there were the 16 wheeler trailers. As I got out to go use the restroom I noticed that a guy was looking at me from his truck but I didn't think anything of it. I used one of the stalls instead of a urinal and about 30 seconds later I heard a knock on my door. I was so scared that I froze but the knock got louder. Shaking I opened the door and the man that was staring at me was standing there with his cock out. He pushed me onto the toilet seat and stepped into the stall with me and closed the stall. He said we were only going to leave once he came so I better start sucking. I was so nervous and scared that I began to suck his cock. After a while he put his hands behind my head and began to fuck my face. I felt his cock being to throb as he took it out of my mouth and came all over my face. He slapped me hard and said thanks. I stayed in the stall for about 5 more minutes frozen and in disbelief of what just happened. I ran out of the restroom and got in my car and drove off. I was so shaken but noticed that I was rock hard and was having thoughts of me sucking his cock. I pulled over and began to clean my face but something about him and his cum on my face turned me on and I began to eat the cum. I pulled my cock out and began jacking off and came so hard just thinking of him fucking my mouth. After that night something else happend that I was not expecting but that's for another time...

Late night thoughts here from a 32 male dom/ sissy trainer! I feel like sissy task can become unoriginal and over used sometimes. I’m looking to freshen up my “tool box” of task and would love some help from doms, dommes, or sissies!

What are the best task you’ve seen recently? What is the key to making a creative task that’s more in depth and thought provoking? Is this even something sissies are looking for or do yall like the simple, run of the mill task doms give out?

Happy to hear any and all thoughts!

I’m submissive dirty guy who likes degradation, wife dominant loves to humiliate. This past weekend we had sex a lot, she’s always on top. She said she couldn’t feel me inside of her and told me she needed to lock my dick and find someone else, Only action I would see is her pegging me, (all normal for us). She called me a faggot for the first time and I came right away.

We are planning another romp during the week, where I will be cross dressed and pegged.

I do need to confess that even though, I was pretty sexed out as of yesterday. Today I was prepping my ass for this week and it snowballed into fucking myself with the dildo to be used, crossdressed, chastity, and downloading Grindr to talk to strange. I’m sure PNC will hit when I cum today or this week, but the fact that I’m such a sissy today after all weekend, is a little scary and fun.

So I was home alone one day and felt a tiny bit horny, decided to shave myself grab my 10inch dildo and bounce on it for abit, unfortunately it wasn't doing much for me, so I downloaded grindr again to see what's out there.

After about 10 minutes I got a message, "heyy baby, I love the way your body curves, think you could curve it on this" and then sends 5 pics of his bbc. I promise you girls I was drooling, but at the same time was abit sceptical, so I gave him my addy and said "see for yourself 😏"

7 mins later I hear a knock on my door and check grindr, it's him he told me he was here and I texted him, "walk in and find me" I was on the couch bent over face down into the couch, he grabbed my ass and I could feel his huge hands on it, (idk if anyone else can tell but I notice the difference between black men and white men when they grab my ass) but I could tell he was black and fuck it made me twitch.

I felt his breath close to my bussy and he said "fuck it looks tight, ever been stretched by a bbc before?" I went to reply but just as I said "ye-" his tounge was in my ass and I let out the most feminine moan I ever have. I felt his tounge deep in my ass and I loved it. After about 10 mins of him eating my bussy he grabbed my throat and said "mmm now your ready".

I was scared, I've had bbc before but if his pics where real then this would have been the biggest, and thank God they were real cause he put the tip in and I was ready to tap out, he hushed me and said "you told me you could now take it" and slowly pushed deeper, I was crying and moaning but I loved every minute, I thought he was balls deep cause he stopped pushing and I heard a groan, but he just said "this bussy is tight as fuck baby, I'm only halfway" my eyes shot open and I looked back and sure enough he was only halfway in my bussy

I was scared, about 5 mins later he was balls deep and I was pushing back on it loving every inch, I put my hand on my stomach and felt his bulge, that alone made me leak onto the couch, he treated me like a slut and told me to clean up my mess, while i was literally getting dig out by this monster I was also licking up the precum I had dripped all over the couch.

After about 30 mins of him pounding my bussy, pulling my hair, choking me, slapping me, calling me all sorts of names, he told me he was about to cum. And like a good slut I begged him to cum inside me, breed me, get me FUCKEN pregnant, and he was about to pull out but I pushed back and that pushed him over the edge, he grabbed my waist and shivered and jolted as I felt the biggest load ever explode inside me, I started cumming through my cage and i was sure I was having a sissygasm.

After he was done cumming he pulled out, grabbed my chin to look at him, as I did I got a glimpse of his limp cock, (still 7 inches soft🤤) glistening in my juice and his cum then I look at his face and he kissed me, told me to be ready tomorrow for round 2, this has been happening for about a month now, atleast once a day I get creampied and he says I'm the only slut he fucks, I wanna believe him but fuck idc if he shares his monster cock with others as long as I get that juicy load at the end of the day.....this sissy is happy

Love you babe's 😘😘🥰🥰❤️❤️

I sniffed my dad's (51) dirty undies from the washing bin and let me tell that made me the hornyest I've ever been

I am what I would define as a straight man but having discovered transgirls/femboys/sissies a desire has awoken in me . The thought of being a bottom for a transgirl/femboy and letting them use me as their sissy feels so hot to me. Doubt it'll ever happen for me but I needed to get that off my chest . Anyone else ?

​

About me-

I'm M19, (5'3 skiny) in role of sissy/femboy(open to share pics and roleplays)

On my recent post about by roommate fantasy, i got tons of DM from many BULLS literally more than i expected... Most of them were normal but some DMs were too rough like HELLL...Literal r\*pe threats, abusive ,soo darkkkkk daammnn!!..

Although they were scary for me but at the same time they madee me leak literaallly from my soft clittty...

I was leaking reading all those dms and tbh it was embarrassing for mee, i think i have loosen my masculinity that i leaked just reading themmm😭 making me weak further but i fuckin love thisssss.

Those BULLS are literally kicking my fantasies for my roommate.... Please hope my dreamm come truee ❤love y'all

I’m an in experienced 20 year old sissy and my big time fantasy is having an online daddy maybe in real life to but it find it hard to find people close by. Being send toys and clothes and having to do tasks with them is my biggest fantasy. I have pics in dm are there people interested in this?

Long post warning

I think perhaps it's a pretty common rabbit hole, but that's how it started for me.

once upon a time when I was a 22 year old young man a bit drunk and plenty horny, I knew a thing or two about crossdressers and sissies from porno and figured "what the hell, lets give her a go"

I downloaded Grindr met a beauty (at this time I was fit, 5 mile runs and all so it was real easy to find sissies I had a crop so to say anyway ) after this 1st time I was hooked, the next 3 years that was my only source of sex sissies all the time most every night

Till one fateful day I had a thought "she looks like she's having fun, what's so good about it"

That was the hook line and sinker ultimately, I went home with some panties I had collected and threw them on (I had tried them on before the classic stole from my mom/sister schtick so I guess it was in there at a much earlier age but buried)

It felt as all of you know amazing, I then started masturbating and gently pushing on my ass hole that's when things turned, next it was a toothbrush handle, brush handle, then on and on and the usual

Flash forward 27 I had a collection upgraded to plugs and a few toys nothing major and I eventually got the courage to ask a friend of mine about it, she is a trans woman that I had known from highschool we had a occasional hookup but good friend ultimately, I know she had a liking to top guys but always made it clear I wasn't interested.

When I finally brought it up, we had something like a 5 hour conversation she was really excited, she introduced me to maaany things, hypnos, poppers, makeup, heels, Reddit. ECT.

After the first meet she just showed me all the possibilities in the rabbit hole we did a little poppers and watch hypno, the 2nd time was a bit more, we did the same hypno pops. but this time she did none but caressed my thighs and neck while whispering sweet stuff in my ears and gently rubbing my now caged dick with some toys.

The 3rd was the whopper, we did the same, but then she asked if I wanted to suck her off, of course I agreed, after awhile of some unrefined skills, She told me to get on the bed and on all fours (more poppers 😅) and then she began to eat my ass and finger me, water a while the big show happened and I realized

"Oh wow, I just got fucked" she stayed inside my while wanding my cage, I had a very intense orgasm

On the drive home that's when I realized I just made a complete 180, I thought of all the sissies I fucked and if they thought the same thing as I'm thinking now.

The next day i was ashamed and beginning to want to throw everything out, the next week I was riding a dildo again watching hypnotube futa dildo hero 😅

I got a bit carried away on this post telling this story but I guess ultimately what I'm curious about is how many of us did this happen to or similarly I'm now 28 and yep this is something I very much love doing?

Met up with a black guy on Grindr a few days back. He didn't ask much about me. Not even for a pic. He was more interested that I was close can could meet now. We meet, we park and I start sucking this BBC. A few minutes into it I look up and he's got his phone out. I ask if he's filming and he says yes. I never agreed to this. It was never brought up before. Instead of stopping and saying no. I looked at him and asked if he was gonna jerk off watching this fag suck his cock.

I cum so hard now thinking there's a video of me out there being a fag. I don't like that I like it.

I can’t believe I’m actually typing this. After months of chatting, sending pics, and following his rules, I’m packing my bags (mostly lingerie, heels, and a few “boy” clothes for the drive) to spend a full week as his live-in owned sissy. He’s 40, very dominant, and lives in this adorable but extremely small lakeside town of maybe 300 people. With quiet roads, everyone knows everyone, mostly older folks living there.

I’ve been an online sissy for about a decade now, chastity 24/7, plugs on command, full makeup and outfits during video calls, the whole thing. He’s strict but caring, and the way he talks about “breaking me in properly” once I’m under his roof makes my clitty leak every time. This week is the trial: I show up Friday night, and for the next seven days I’m 100% his. No guy mode. Full sissy protocol the entire time. He’s already picked out my daily outfits and has a list of chores, training sessions, and “public practice” tasks that have me blushing so hard.

The small-town part is what’s really messing with my head (in the hottest way possible). His house is right by the lake, super private backyard, but the grocery store, the one coffee spot, the dock… it’s all a five-minute walk. He’s warned me I might be going out dressed appropriately “for a good girl” at least a couple times. The idea of being seen by locals who have no clue what’s happening behind his doors is equal parts panic and arousal.

I’m nervous as hell, what if I’m not sissy enough for him in person? What if the isolation makes it too intense? What if I never want to leave after the week is up (ideally)?

Has anyone here done a similar trial run, especially in a super small or conservative area? How did it go? Any advice for a scared but eager little sissy who’s about to hand over the keys ?

P.s. I'm in canada

— soon-to-be collared sissy