r/SissyConfessionBooth

It finally happened (Cuck, Chastity, Threesome)

TLDR; After years with my wife who doesn’t like to dom, one night of drinking with friends finally got her to finally cage me and even consider cucking

Im not sure how to start this but basically my partner \[26F\] has always been less adventurous in bed than me \[26M\]. She was a virgin until we got together and had never even watched porn because of strict parents. Meanwhile, I’ve been watching porn since a teen. This means I’m typically the one initiating sex with a higher sex drive and even when we do have sex it is very vanilla. However, since I obviously want open communication with my partner I have discussed with her years before we were married a few of my kinks in the past. This includes but is not limited to things like chastity, sissy porn, cucking, raceplay, etc. I also talked about bicurious tendencies I had like using a dildo every so often to suck and ride in the bathroom.
She is a sub in bed while I am more of a switch so she admitted it wasn’t really her cup of tea since she wasn’t used to being the dominant one but she was willing to try it anyways for me. We tried a few days having me in a chastity cage and she even watched me use a dildo and butt plugs on myself a few times but that was that. Again though that was before we were married. As years went on, the routine was the same, vanilla sex maybe once every few months.

That was until a few weeks ago.

For context of the rest of the story, she has 2 friends, let’s call them Amanda \[25F\] and Ashley \[27F\]. She’s known them since school and I’ve met them and we’ve all become close. I also have a best friend we’ll call Richard \[26M\].
We have an anniversary coming up so my partner decided to go out with Amanda and Ashley a few days before. She texted me while she was out saying that she was going clubbing and drinking. This was very unexpected as again she is usually a shy, vanilla person. In fact, not only is it not common for her, she’s even often expressed a STRONG DISLIKE for clubs and alcohol. For whatever reason though that night was different. She came home and was more energetic. She took a long shower that night which isn’t too out of the ordinary. Even when we don’t have sex, she takes longer showers when she uses her fingers on herself and masturbates. When she got out of the shower though, she told me she was in there using several toys on herself. This was also a surprise. I had gotten her dildos and a vibrator in the past put shes only used them a few times in the past year. I asked her what could have prompted her fucking herself with the dildo for the first time in years and that’s when things really got interesting.

“Well, you know how I got drinks with Amanda and Ashley? After a few drinks, somehow our sex lives came up.”
With a bit of nervousness but also curiosity I ask, “Ok….so what did you say?”
“Well I was honest with them….my husband likes when I put his tiny dick in a cage and make him my little bitch.”
If i had been drinking water I would have spit it out. I was shocked. Part of me should feel betrayed that my partner was revealing such private details of our intimacy. Especially since again we hadn’t used chastity in a year or longer. However the other part of me was taking over that sorta loved being exposed, it also loved the nature of dominance I hadnt gotten out of her in god knows how long. “Well how did they respond to that??” I asked. “They admitted that it’s kind of hot and they wish their partners were that submissive to be honest. They told me how lucky I was.” I was a bit relieved and again turned on by this. Not only was her exposing it not immediately making me the clown of the friend group, her friends are even kind of into it.

She continues, teasing me,
“I told them about how my husband likes having his masculinity humiliated, wearing feminine clothes while his little tiny penis is locked in a cage.” She pauses for a sec analyzing my reaction. “At least….that’s still true isn’t it?” she asks in a teasing tone, knowing the answer. I nod sheepishly and she giggles at me.

I wish she had kept degrading me but it stopped there for the night. The next morning she started talking about it again

“Hey, honey. I have more things to say about last night.” After a pause she goes, “Honey, be honest. I wont be jealous. Do you want to fuck Amanda?” I was stunned at the question, just as i had at the retelling of events from night before.
For context, Amanda has been in a relationship even longer than we have, however she is practically a model. She has all the best fashion for instagram and loves to cosplay anime characters too, sometimes in more seductive ways, meaning I’ve seen her on multiple occasions in fishnets, bunny suits or other TIGHT/risque clothing. So i had to be honest, “Well, if there’s no judgment then I’ve definitely pictured it, especially with what she wears. Both us and her are in committed relationships though.”
“Aw babe, thanks for being honest with me. I ask because Amanda was actually talking about a threesome…or possibly even switching partners for a night.”
I perked up even more immediately. She adds on, “I asked Ashley too butttt she said we weren’t really her type which is disappointing. I mean I cant blame you for wanting to fuck Amanda. Even I have thought about it.” I was shocked and rock hard. My wife had always been pansexual but hearing that she was considering giving me the chance to have a threesome, especially with her hottest friends was a fantasy I always had and so i couldn’t get it out of my head.
Then she hit me with an absolute truth bomb.
“But if we’re being honest, I need to tell YOU something as well too.” I pause nervously.
“If you are telling you want to fuck Amanda, I want to fuck Richard.” Just like how Amanda is basically a model and has been a good friend for years, Richard has been my best friend since high school and is 6 foot 3, with an amazing fashion sense as well. It honestly didn’t surprise me that she would want to fuck him, more than half the woman who have met him probably want to fuck him. I just was not expecting my partner to openly come out and say it.

Then came the best part. She finally asks me openly, “Soooo are you still kind of into cuck stuff as well?” I had a feeling I knew where this was heading but I still respond honestly, “Yes, I’ve thought about you cucking me a few times.” She asks me what is it that I like about it, why is it a kink. I admit here that I stole a line from another redditor ive seen having to describe it to their wife saying, “Well, in a way it’s like watching porn, except my partner is the pornstar, and I get to see your faces as you orgasm and are given extreme pleasure.” She accepts that answer but wants to dig deeper. “Do you like the humiliation aspect of it too? Knowing someone else can pleasure your partner better than you can?” I sheepishly nod.

Then she drops might be the hottest thing she’s ever suggested
“Well then I have an idea,” she says, “How about I fuck Amanda, then later I fuck Richard, and both times…you get to just watch in your little cage?”
I swear I couldve cum right there. Even if it made me a pathetic, sissy cuck I didn’t care I was ready to call Richard right then and there. I couldnt let this fantasy go to waste. She followed it up by “Or better yet, you suck Richards cock to get it ready for my pussy. Your best friend’s cock in your mouth and fucking in your wife, does that sound nice?” Even though Richard is my best friend and I never thought of him that way. This still got me insanely hard and close to climax. If it happened it would take my bicuriousity with a dildo and turn it into a real cock, as well as the full cuck experience. But I must have shown I was too eager, as she sorta backtracked a little and said, “Well we’ve only been married a few years, let’s give it a bit more time before I fuck someone else.”
I was slightly disappointed she would tease me so much with the idea and wave the carrot in my face only to say I have to wait for it longer, but this vibrant energy Ive only seen a handful of times in our relationship and it gives me hope maybe it WILL happen one day, and I was so excited I just had to share.

Since then we still have not done any cucking obviously but she has still stepped far behind her past vanilla self. She has sent me nudes for the first time, she has caged me far more often, with me currently being in chastity for a month which is the longest Ive been locked so far. She has pegged me. She has watched me use the dildo on myself. She has made me worship her pussy and eat it. She has used the vibrator while forcing me to only watch as she cums and Im denied. We bought a cock sleeve extender, something you put your dick in but the end is like a dildo to make it longer, and a few times she has only let me have sex if i wear it so she can “feel a real cock’s size.” Which makes me insanely hard.

So Here is to me hoping this all leads somewhere and my kinks are realized. I love my wife but seeing her in ecstasy and cumming while Im denied as a submissive sissy cuck or sucking cock with her is literally my dream. If anyone would like to talk more with me, my inbox is open, but I do not share pics as me and her have agreed our nudes are exclusive to only each other (her choice). She knows I have a Reddit account too but she doesn’t know it’s this specific one so idk what she would say reading this either.

Idk how to tell him, I know he’s straight, but he’s also sent me a insta profile that was a femboy and he said he’d do her if he could. How do I tell him without him thinking I’m weird?

I have a gf and very straight however I always had sissy desires to be dressed up and shown what it like to be treated like a woman and experience sex as a woman. when I was young and home alone I would wear my mothers underwear and dresses. now I own a couple pairs of my own panties. I wonder if these desires will ever leave. feel free to send dm if you want to chat

Well I did it again. I tried not to, but couldn't help it. I visited my older sister the other day, and ended up "borrowing " a couple pairs of panties. I tried to resist the urge, but I couldn't help it. I know I shouldn't, but its just so difficult not to.

Went to apartment store primark today. For the first time buying clothes I bought cute clothes. A bra and panty set, lacetop stockings, cute pj's, and a cute pair of shoes. Walked around for about an hour, looking at all the beautiful clothes. Then, I just filled my basket and went to the self-service . Nobody batted an eyelid. I've never been so nervous I was shaking. Young wo.an on the next check-out gave me a big smile and a wink when she saw what I was buying !!! I'm on a high the adrenaline 💖

Lately I’ve been communicating with a top with a bbc. And last night we finally met. In my barn he came in and pulled down his pants and revealed his beautiful dick . It was the biggest I’d ever seen personally. Long and thick . And when I dropped to my knees and sucked it grew even more. He grabbed my head and gently fucked my face , choking me just enough. Then told me to turn around and using just my spit he shoved it in me . Oh wow he kept shoving and twisting until he was balls deep taking my breath away. Then he started fucking me like I’d never been fucked. He twisted me every way but loose . I came twice. I never knew it could be that good. When he came he kissed me (another first). And all I could do was lay there. After he left I told him he could fuck me any time he wanted to and could I be his closet bitch. We’re supposed to get together tomorrow night and I can’t wait. Thanks I just had to tell someone

Just to paint a picture I’m a very muscled tanned male with no problems over my years getting women and pleasuring them BUT. Over the past 3 years my addiction to trans porn has grown excessively stronger over the years.
It started as only liking trans on girl but to where I couldn’t see a penis was visible , then to trans on trans and now even men absolutely ruining trans girls even when I can see there penis is visible. It’s bending my head. I had a trans baddie similar age she could say one thing to me and my cock would break out my pants harder than any girl could make me. I used to cum 8 times a day to her. Every day I chose to masturbate over trans porn but every single minute, day, month and year it turns me on so much more to the point I NEED to fuck a trans but I’m so scared il become addicted and not like
Pussy again. My man fear is am I straight?????
Help

I’ve been a little sissy for a while now, and I go back and forth it’s so hot, but sometimes I wish I just had some encouragement or help. I love bbc and worshipping cocks, but, no cocks to worship :( I’m all caged, censored porn only, I fuck myself with my dildo so frequently, but I just wish I had some hot cum in me like. Why is it so hard idk 😭

Anyone relate?

Been getting more and more adventurous lately and honestly it feels exciting finally letting this side of me out more. The other day I drove around my area wearing a full black lingerie set, heels, long nails and a wig. No makeup yet unfortunately — still pretty new to all this and building confidence step by step 😅

I’ve also started wearing lingerie under my normal clothes and even under my work clothes sometimes. And recently started plugging too. Feels like this side of me is slowly becoming part of my everyday life instead of something I only think about in private.

What have you started doing more or how adventurous how you gotten 😉 I’d love to know 😘 xoxox

Okay, here it is. Another confession.
This one is easy to make. I don't wash the bed sheets after every hookup. Even if there's a little cum splatter or sweaty wet stains. I love the smell of sex. And I like to savor that smell even after the guy runs away. Yeah, and most guys cumming to hookup run away. Blow n go guys included. Once they unload, they move on quick. Not many cuddles these days. It makes me realize now, especially since I'm older (58) the foreplay, kissing, cuddling, groping, sweet dirty chatting. All of it becomes more valuable than just, bang N leave! Or chew N screw! Just saying, I must be slowing down a bit. But, I still managed 4 hookup guys yesterday. Exhausted. But satisfied. Oh🤔 back to the story ( sheets)

Yeah they get dirty. I don't mind much. Unless there toast I wash about every 2-4 hookups. Does that make me a bad ( naughty) gurl🤔😋 I do more often after threesomes. Just got too. Lots of tasty sweaty men! Yay🥰