Just found this sub and thought I should give you my story!
I discovered I love trap and sissy things. I discovered Hypnos early on and I would steal dirty panties from my female friends and wear them like that. Well I started seeing one of those girls I stole panties from, and not long after we started dating, she told me she know what I had done.
Well I froze up and didn’t really know what to do or say. Well she took that as me admitting to it. Well I was pretty skinny at this point, 140lbs and I was 5’8. That meant she could dress me in her clothes, which is what she did. Day after day she did this. I would go over, strip down, and she would always have an outfit waiting. Well it wasn’t too long, maybe a week or so of this and she ordered what looked like a small c cup set of fake boobs for me to wear to fill out her bra. That then led to the long red haired wig she got for me.
Finally she decided that it was time for me to shave my legs, and learn how to do make up. Just simple make up, but she wanted to make sure I could do it. Well this whole time we never went out in public. Well that changed about a month in of doing everything she asked.
Well, it wasn’t enough to just go out, she locked me in chastity, because she said I earned it. I was so excited, like I could believe I was actually getting to experience this. Well that then went to shock we she told me I would have to earn getting released now.
She told me before we left that she had a surprise for me. I was curious because I didn’t know what to expect. Well, she told me to sit on the bed and close my eyes and wait. I did that, for what seems like 10 minutes? She finally told me to open my eyes, and there she was, in a bra and her panties, wearing a strap on.
She told me to open my mouth and suck her cock. She said I needed to practice for the real thing. My heart raced as I opened my mouth and sucked her 6 inch rubber cock. She gave me some moans of encouragement and I finally felt her hand on the back of my head. She told me to get ready and then slowly pushed my head down on her until I took the whole thing. She held me there for a bit and I could hear myself gagging. Finally she let me go, and then did the same thing a few seconds later. This went on for what felt like a lifetime. All the while I can feel my cock straining against the cage and leaking cum all over my panties.
Well now here is the fun part. I have never, never had anything bigger than a finger in my ass. She knew this, and never really pushed the subject. Well after me sucked on her strap on for almost half an hour, she tell me to get up and pull my panties down. I was usually in a thong (she loved that, and would make me sniff mine and hers and lick them both), so I bent over and she told me finally that I was going to be plugged while we went out. She knew this excited me because I could feel my cock jump in its cage. She lubed up my ass and the plug and told me to get ready. I felt the pressure of the plug opening my ass slowly. It wasn’t huge, it was actually pretty smallish, made of silicon. After a few minutes, she finally pushed it all the way in.
We then went out to the mall for a hour and she introduced me as her “girlfriend” that just moved to town.
I couldn’t stop. I was being “forced” to practice sucking cock on my girlfriends strap on. It was a daily occurrence. 15 minute sessions quickly became 2-3 hours. Not only that, but the plugs got bigger and bigger too. Bigger plugs, longer times inside my ass, I was honestly beginning to question it all.
I wasn’t in a chastity cage too often, as sex was still something my girlfriend wanted from me often. As the time went on though, there was more talk between us on her getting a boyfriend. Well I mentioned I was her boyfriend, to which she responded, “no sweetie, you are my sissy boyfriend, there is a “big” difference”. She went on to tell me she wanted a big cock inside, you know, something I didn’t have.
Well that’s when I really went into question overdrive. I told her my feelings, on everything. And while she understood, she asked me to try one more think before I gave it all up. She wanted to fuck me. Now my fantasy was really coming true, why not try it? So I told her okay, I’ll let her fuck me.
It was a week or so later, I showed up, all dressed as usually at this point, that she answered the door and was ready, strap on right there. Something was different, she was very much in a dominate mindset. The told me to get inside, go to her room, and wait. I didn’t dare question it at all. I did was I was told. She came in a bit later, and handed me a blind fold. She to me to do as she said and not to hesitate. I wasn’t really even thinking and I just did want she said.
Soon after I felt her undress me, and the chastity cage click around my cock. She leaned in to me and whispered for me to open my mouth. Right as I did, it was stuffed with what I found out were her panties, but they were so wet. Then she told me to bend over the bed. She helped me get in position, but then it happened. Click. Handcuff. I was to excited about what was happening to realize it, but there I was, at her control.
The lube hit my ass, and I jumped, I knew it was coming. I couldn’t stop it. I didn’t want to stop it. That familiar pressure hit my ass again, only this time I felt something different. Her hands around my hips, pushing. I could feel every little millimeter of her rubber cock enter me. It wasn’t the thickest thing I had in my ass at this point, but it reached deeper than anything. I felt it fit, right on my prostate, and glide over it until finally, her skin was against mine, and the rubber balls from her cock met my caged balls.
I enjoyed it. I won’t lie at all, but the next part is where everything really changed. She told me she was going to start slow, and work her way up. Well it didn’t take long to get to that point. The panties didn’t last too long in my mouth either. I was moaning like a girl, getting fucked by her boyfriend. Only this was different, this rubber cock wasn’t going to cum, and it wasn’t going to get soft.
I heard her say finally, “since you like this so much, I should tell you, I’m not going to unlock you, I want you to be my sissy”. I don’t know what is was, but those words hit me hard. I could feel the building of something inside me the hard she fucked me, the faster she fucked me. Yet when she said those words, it really happened, I came. I came from being fucked in the ass. Not just that, I came from being a sissy, in a chastity cage. I was a sissy.
Once I came she slowed down and after a while, I felt the cock pop out of my ass. “Clean up your mess” I heard her say as she removed the blindfold. I put my head down to the floor, and locked up my cum. I saw her smile, and I knew I wanted her to be happy, I wanted to make her happy. Then I got the real test.
“I hope you don’t mind, but I invited a guy over that I have been talking to, and told him about me and my girlfriend.”
Well honestly from the last point in my journey, things actually died down. There was no guy that ever came over, and my girlfriend never did go find anyone else to fuck. I even encouraged her to look, and told her I was fine with it, so long as things were still communicated. It didn’t happen, at least not for a while.
Actually the opposite happened first, she wanted to take a break. She said of course that she had fun, but just wanted to focus on her. Now keep in mind this was…about 3 months after her fucking me for the first time, and overall is having been together for about a year.
As much as I wanted to fight, I didn’t. I knew she needed a break, and then again maybe deep down I wanted on too. So we took a break (don’t worry, spoiler we get back together)
She gave me all of the clothes that I had been wearing, and she told me she honestly hoped I didn’t throw them out and go back to just being the guy that stole panties. I didn’t tell her, but I didn’t think I could go back. I always have a little nagging in my head telling me to abandon the sissy ways, but I never did.
So I continued to dress as a girl, I continued to wear buttplugs out from time to time, and even slept in them a few times. I found chastity was my friend. I locked myself up, and really made a game of it. I would start with a week, and if I didn’t cum in my cage, well I would let myself out. Well I got my own dildo, nothing special, just one I found online. It was about 8 inches, and I just wanted to work my way to bigger things.
Well I rode this dildo every single day. Sometimes for 30 minutes, the longest was an hour and a half. I didn’t cum every time, but I did cum more than once a week. I knew I found a way to keep myself locked up.
Well since I left off, I was now in a somewhat single state. So I just kept up my game of self chastity. It was fun, but I felt the itch for something more. Something real. So I started searching, and I just happened to find a guy who wanted to play with a sissy. I didn’t know what to expect but I decided to take a chance.
A few days went by before I got a response. We talked back and forth and I didn’t really think, but I just straight up asked about meeting up after the following few days. Just like that, he said how about tonight? Again, my heart raced. Was this it? Was this my point of no return? I was excited and even more nervous. We set a time and I started to get ready.
I mentioned to him that I had locked my cock up in a cage (and at this point it had been about a month straight).
“Good, you won’t need the key”
Again my heart went crazy.
I put on my bra and thong, just as he asked, and wore a skirt. I push my biggest plug in my ass, a large silicon Doc Johnson plug, and did my make up to the best I could. He asked for a lot of eye make up, and I knew what that meant. I did it. I did it all, and I got to his apartment. And he answered the door. Naked. With easily the biggest dick I have ever seen in person. True that wasn’t hard to do since I hadn’t seen many at that point. But of course my eyes fixated on it. It was around the 7 inch mark, but it was thick. Like wrist thick.
“Well I see I don’t need to tell you want to do”
I walked in, and he shut the door. He push down on my head a little and I dropped to my knees. I was at a loss of what to do. It’s like everything escaped me.
“Well?”
At those words my hand wondered up and I started touching and stroking his huge cock. As I did this, he inches it forward, little by little. I could smell it, it wasn’t the best smell, but it kind of called to me. I licked the tip of his cock and after a few minutes of this, it was in my mouth. His fleshy, hot cock was in my mouth, and I could feel my cock leaking at just this.
Then it happened. His hand on the back of my hand, and he pushed, and pushed, and pushed. I gagged and I could feel the tears, and along with it my make up run. It didn’t take long and his hot balls were on my chin. He went through this over and over, and I could tell my throat was loosing up, but also become of raw.
“I’m going to fuck your mouth now, okay”
All I could manage was a moan. Then he begin. In and out, pumping away at my mouth. The moan and gags filling his apartment with sound.
Without warning, he pulled away after some time and exploded in my mouth. My first cumshot that wasn’t my own. It was thick, and there was a lot of it. Finally he grunted one last time and his cock fell from my mouth.
“Be a good girl and swallow”
I did. I swallowed it all and it was like I wanted more. I wanted more cum. It wasn’t exactly the best taste, but something about it just made me want more.
“Have a good night”
That’s all he said, opened the door, and I got up and left.
So I got my first taste of a real mans cock. Well I couldn’t stop think about, both good and bad. I mean I was so proud of myself for going through with it, but I still had a girlfriend, didn’t I? I mean we were just on a break. Well it turns out I never heard from that guy again. I was bummed out, but it wasn’t long I had another guy wanting to meet. Well of course the first meet went great, so I decided to go through with this.
Well the difference is, he showed me his cock before I went, and i could feel my cock tingle and drip. I actually caught myself staring at it in my down time and daydreaming. Well he then ask before if I had ever been fucked by a real man. I told home no, at least not with a real cock. The last message I got before we met was simple.
“You are never going back after I’m done”
For some reason it freaked me out. I ghosted him. And I just stopped looking for a while. Something about that made me think twice about it all. I did the only think I could think of… I went back to the girl who I was on a break with. I told ember everything, including my then current doubts about everything.
Her response was definitely not something I was ready for.
“Well I have been talking to a few guys, I told them about you, and a couple wanted to play with us if I ever wanted…. well they wanted to play with you while I got to watch”
I froze. Other guys, play with me, you watch? Really? The words “am I just a slut to you” came out of my mouth. Then her response really shocked me.
“Isn’t that want you want to be? A sissy slut?”
She hit the nail on the head. Damn, it was exactly what I wanted. The best part was she knew from my silence that it was what I wanted. I wanted to be that sissy slut I knew I was in my head. I knew deep down I was meant to serve real men and women.
She reached down and shoved her hand under my skirt and grabbed my cock. My cock that was still in the cage.
“You never gave this up for a minute, did you?”
Of course I didn’t. I couldn’t. I wanted to be a girl. I wanted to be a sissy slut. All I could do was nod or shake me head. I was speechless. I wanted to taste as many cocks as I could handle. I wanted to be fucked like a sissy. Most of all I wanted to cum like a girl.
She grabbed her phone, and opened the photos. She held it up in front of me, and look me to look. The first cock belonged to a ripped stud of a guy. I mean just powerful looking. His cock was a beefy looking monster, long and thick, and so veiny. Then she swiped over and I felt my mouth fall open. The one cock I had always dreamed about having. It belonged to another ripped stud, and it was the biggest cock I had ever seen outside of porn. It was thick and long, and made the other guy look tiny by comparison. This was the much wanted (for me) BBC of my dreams.
“They both want to cuckold you. They want you to watch as they take me make me feel amazing. They want you to suck there cock, and just watch. They want to cum inside me, and have it drip into your mouth, and on your face so I can tease you with my pussy. Plus it just so happens they both want to stuff your ass full of cock. Their cock, while I watch and enjoy.”
She knew before I could even say anything that I wanted that. My cock was leaking. It was poring precum onto her finger and into my panties. I heard her giggle and stuff her finger in my mouth.
“Clean it. I know you want this. If you don’t, and your really don’t, say so now, or this is happening.”
I was silent.
So the next couple of weeks following were really what cemented my life as a sissy. I turned over the key to my girlfriend, and that was that, she was in control again. It wasn’t the same though. No she found out that being mean to me set us both off. She would show my pictures of the guys she was talking to. Show me there cocks. Tell me how much better they were than mine.
I started getting those texts from her while I was working. You know, teasing me that she might be with another guy, and how badly I wanted to know if it was the truth. Honestly, I loved it. It really did keep me on edge constantly.
Finally she had enough of the teasing. She invited the guy over, let’s just call him the alpha, because he was. She set up a little place on the floor at the edge of the bed, attached a 10 inch black dildo to the mirror, and called me over.
“Strip sissy”
I did, complete down to nothing. As she smiled she looked over to the dildo and nodded towards it. I didn’t need to be told, I knew what she meant. I walked over and hovered above it, and she lubed both it and me up.
“Sit, all the down, and don’t you dare move”
Well that was the problem. That was longer than anything I had inside me at the moment. I hesitated, but I started to lower myself. I felt the head pop around my ass as I slowly made the decent. It took me much longer than expected, but to my surprise, I was now sitting, balls deep on a huge rubber cock. My cage had sprung a leak, and it was obvious thanks to the mirror under me now.
She wrapped the blindfold around me again, pulled one arm to one side of the bed and a click, followed by the same with the other arm. I was stuck here.
“Now you get to wait, and if you are good, you’ll get rewarded”
I have no idea how long I was there, but I finally heard the doorbell. Walking down the hall. The door opens on me it my position. I heard her say…
“Open your mouth, and do a sissy’s job”
I opened without thinking what this meant. My mouth was full. It was hot, fleshy, musky cock in my mouth. I suck it. I wrapped my tongue around it. I gagged on it to the point I almost threw up. Gagging on this cock hurt. Then, nothing.
“Put that big black cock inside me”
Those words hit me like a train. I had almost no time to process before the loud moans of my girlfriend filled the room.
“Please. Fuck me like a real man!”
“I’m yours now!”
“My pussy belongs to you”
“Don’t stop daddy”
I could hear everything. I could hear every single time she came. I could hear how wet she was. Then my mouth was pushed open again. This time it was a finger, but then it was something different. It took me a minute to realize, but he’s balls now filled my mouth to the brim.
“I want him to feel you full my pussy up”
I moaned at this. I actually moaned.
“See, my sissy loves to please me!”
She said this between moans. It wasn’t long after I felt it. The constriction. His guttural moan, and her finally words of the session.
“Fill my pussy up daddy”
Soon after, it was quiet again. A deafening silence. I was processing everything now. She fucked a guy, I sucked his cock, I sucked his balls, she called him daddy, he came inside her!!
I was a rush, and thanks to my body betraying me, I was rocking on this cock inside of me. I was fucking myself trying to get off to what just happened.
Click
“I hope you are ready, its your turn next sissy.”
It was my turn. It really was my point of no return. Both cuffs were removed, as well as the dildo. I was moved around and bent over the bed, and recuffed in that position. I was scared. I was excited. Honestly it was so much. I felt the lube being pour over my already gaping ass.
“Ask for it sissy. Ask daddy to fuck you like a girl”
I froze. The only word I could manage was a soft “please”. His cock was so close I could feel the heat coming from it. I could only imagine my locked away cock just turning into a fountain of precum.
“You better ask right my little slut”
I managed a “please, fuck me” this time. The head of his cock, that huge beast that was going to take my real virginity was not even seconds away.
Slap, Slap, Slap.
His huge hands landing and making contact with my bare ass made jump, as much as I could in my state.
“Ask properly sissy!”
She yelled this time. I broke. I couldn’t get around this. “Please fuck me daddy”. I felt my voice actual crack at saying this.
My embarrassment for saying these word left instantly. It was hot. It felt like a burn hot rod was entering me slowly. I could feel my ass stretch around his cock as it slowly made its way deeper and deeper into me. After what felt like a lifetime, his massive balls met my swollen one. I sighed, the worst was over.
I was wrong. Not that it was the worst, but I was so unprepared for this moment. He slide out, and with it what felt like my insides. Then back in, and out, and in. It was an experience that was other worldly.
I could hear myself moaning. Louder and louder. My girlfriend taking this time to really take advantage.
“You love this don’t you? You love pleasing a real man with your little ass? Tell him. Go on, I think he should know”
It didn’t take long. “God I love your cock daddy. Give to me more. Fuck me harder daddy.” I remember these because I repeated them often. Others I forgot. I could feel myself building to my now only means of orgasm, the sissygasm.
Then something I didn’t expect. The blindfold was removed. In front of me, my girlfriend, pussy gaped open slightly, and pushing out his cum into a glass. My mind went into overdrive. He hammered away at me, grunting louder and louder.
Bam
I felt it. His hot cum filling me. I lost it, everything combined hit me. I started to shake, everything started to go hazy, and my legs gave out.
I felt him pull away, and my girlfriend went around and collected his cum that dripped from my ass. Meanwhile, he walked around to my face and stuffed his cock in my mouth. I mindlessly licked it and halfheartedly sucked every once in a while.
The clicks of the restraints meant I was free. Then I felt hands roll me over.
“Open your mouth whore”
I felt her hands push my mouth open as all the cum was pored I to my mouth. It was strong. The mix of all three of us was intense.
“Swallow it all”
I did, but I left it in my mouth for a bit to take it all in.
This continued for a while. Not just with him, but her seeing other guys. Not only was I a sissy, but a cuckold as well. I would get messages about what she was doing, her teasing and humiliating me, and I love it. I would ride my dildo and read though everything she sent over and over until I came.
Well nothing good ever lasts. She kind of moved on. I say kind of because I still get those messages every once in a while from here. Luckily she is in an open relationship, but still uses it to tease and humiliate me when she can.
Source: reddit.com/r/gonewildstories/comments/gsbko9/how_i_became_a_sissy_mfm