r/Sissy_Stories

Continuation story of First Time

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He gave me a short list before I was allowed to come over: fully shaved, black satin panties, my flat cage locked, a corset, and a choker that could take a leash. I showed up three hours early in normal guy clothes; jeans, t-shirt, sneakers. Just some random dude walking into his building.

The second the door closed he told me to strip. I peeled everything off so he could inspect what I was wearing underneath. He took his time. Hands on the corset, checking how the cage sat, tugging the choker. When he was done I handed him the key to my cage. He just pocketed it.

Then he dressed me up. Full maid dress, apron, fishnet heels. He locked the dress closed with little padlocks so I couldn’t take it off myself. In under ten minutes I’d gone from regular guy clothes to locked sissy maid. That hit harder than I expected.

After that he put me to work.

I poured him a glass of wine and brought it over on a tray. He sat on the sofa like a boss, lit a cigarette, and pointed at the floor. I knelt. He looked at me for a second, then said “open.” I opened my mouth. He flicked ash into it. When the cigarette was done he poured a little wine over the ashes and told me to swallow. It tasted disgusting. I still did it.

Then he unzipped. I already knew he was big; almost 20 cm and thick; but knowing and taking it are two different things. I’d only trained up to 13. I tried my best, working my mouth down as carefully as I could. It was a struggle. At one point my teeth grazed him. Two hard slaps landed across my face before I even registered what happened. He told me not to do it again. I apologised with tears in my eyes and kept going until he decided he’d had enough of my mouth.

He stood me up, bent me over the dining table, yanked the dress up and the panties down. One finger, then two, then three. Methodical. When he finally pushed his cock in it felt like it was splitting me open. He fucked me over the table until my legs were shaking.

Then he pulled me down onto the floor, folded my legs up toward my chest and held them there by the straps of the heels. Completely open, no way to close or move. He went back in and kept going harder and deeper until I was making those pathetic little sounds into the carpet. When he came it was thick and deep. Before I could even try to recover he pushed a plug into me. It slid in way too easily with how full I already was.

He unlocked the dress just long enough for me to pull the panties back up over the plug, then locked everything again. He handed me the key to the padlocks but told me I was leaving exactly like this. Walking out of his building in the full maid outfit; plug seated, cage locked, his cum still inside me; was the first time I’d ever gone outside dressed as a girl. I arrived as a guy in jeans. I left as a locked sissy maid.

He kept the key to my cage.

Said I’d get it back next time.

"Guys, the girl I was with last night" Mike says to us all.  I hate when he does this.  He always talks in intimate detail about what he's done to these poor women.  He treats them like shit and when he talks to us about them he speaks in such degrading terms it makes me sick.  But I have an extra special reason to listen tonight.  I know who he's talking about.

"She was so fucking thick it was unbelievable." He says raising his beer. "She fell for the whole 'you know, I've never had a blow job before' schtick.  In fact just because I'm a bastard I told her how fucking dumb she was whilst she was sucking. And she carried on!"

---

Mike and I normally work out at about the same time.  He had finished before me so I wasn't surprised to see him still sat in the changing room when I got in there.  He looked pensive.

"What's up man?" I say as I go to my locker.

"Dude, I can't - not here.  Just feeling really down." He replies. I respect his wishes and we change the subject to talking about sports.  It's not until we reach the car park and are stood by my car before he opens up a bit more.

"This is going to hurt me telling you this" Mike says "You know how I'm always going on about all my conquests and talking about women.  Most of that isn't true.  I just watch some porn and then just pretend it's me." 

"Fuck, I didn't see that coming" I say.

"Yeah - you know I struck out today with this woman at work I've been obsessing over and it all kind of hit me - about what I've become." he says looking down at his feet and before I can respond he drops another bombshell "I mean I've never even had a blow job.  I mean I'm so depserate, I'd take anything from anyone - man, woman, anyone in between"

"Wait seriously?" I say "Like never?"

There's a long pause.  I weigh up what I'm about to say next not sure if I should say it but that little tingle inside my pants makes me think - what the fuck.  This could be an opportunity for both of us.

"Mike, I can...  I will... If you want..." I say stammering a bit as he sort of looks up and smiles and shakes his head from side to side.  "Look, I mean it wouldn't be my first time.  I could help out.  I'm not saying I'm gonna be any good but I can try.  After all, it's just a blow job.  Back when Sarah and I were together we had few threesomes and I tried it then and I'm more than happy to try it again"

This whole thing is a lie.  Sarah and I never had a threesome and I've never had a cock in my mouth.  The closest I've come is listening encouraged-bi videos with a dildo in my mouth whilst wearing a pink latex dress.  I want to.  I desperately want to suck and cock.  And he seems to desperately want a blow job.  I think this could be a win for both of us.

"Look come back to mine." I say going over and putting a consoling arm on his shoulder.  "You've got the whole drive to think about it.  The offer is there - doesn't need to be anything more than tonight.  If you decide to drive away, I won't say anything and I won't think anything less of you and I'm assuming the same goes for what I said."

I drive back to mine.  I see Mike's car following and all the way I'm singing to myself about how I'm finally going to suck a cock.  We get separated at a light I have no idea if he's still following me or not.  My heart jumps a beat when I pull up to my house and see he's leaning against his car.  It's a bit worrying he knows a quicker way than I do to get to my house.  We walk to the door without saying a word.

"So" he says as we sit down "I've been thinking about this.  I *really* want to take you up on the offer but I just think it would be too strange.  I mean maybe if you looked less like the guy I go to baseball games with and more like a woman I could do it."

"Let me see what I've got.  I've got some Halloween stuff and some stuff Sarah left.  We can have a drink, I'll try some stuff on and you can have a good laugh at me if nothing else." I say as my mind goes to the third wardrobe in, bottom drawer and all the women's clothes I have hidden away.  I head to the bedroom and slide the drawer open.  I take out my favourite the fake-leather leggings.  The noise they make as I waft them around and slide my first leg in to them is such a turn on.  I hear the toilet flush as I run my hand up the outside of the leggings feeling how tight they are against my skin.   I take out my ankle boots and zip those up.  I adore the way they arch my calf muscles and make me nearly 6 foot 3.  I pick up the dirty pink wig and head over to the mirror.  I pull the front down and fluff up the curls as I see him standing there. The last piece is a strappy frilly pink vest top which finishes about 6 inches above my stomach .

"This is all from a fancy dress outfit" I say to him.

"Sure OK," he says looking at me.  "I think this will work.  I mean you wouldn't pass as a woman but this should do. Unless? You don't have any lipstick do you?"

I rummage around in the drawer and pick out the sluttiest colour I can find.  I walk over the to mirror and apply it. I can see him watching me apply it.  I turn around to him and gesture towarrds the bed. I kick the drawer of kink shut and walk to the bed.  He doesn't need to know what else is in there. He takes his shirt and pants off and I approach him from between his legs.

"I'll take it slow." I say looking down at his semi hard cock.  I try to stay calm and not give away just how excited I am. I kneel on the bed and position myself between his legs.  I worry that if I stop and think, I'll stop or worse he'll stop me.  I don't want to stop I want to do this and he seems to want me to do it.

I take hold of his cock at the base and stroke him a few times. It's so strange holding a cock. I mean holding *a* cock isn't odd but holding someone else's is really strange. It's still not fully hard. I try and think about how I'd like it stroked.  Rub my thumb against the head on every up-stroke.  I take a breath and then take the mental leap forward that I'm about to make this fantasty a reality and become a cock sucker.

I take the head of his cock in to my mouth and seal my lips around the shaft. I push my head down taking a little bit more in. The tip touches my tongue. The taste is odd. It's salty, sweaty. I move it in and out of my mouth. It's pulsing. It's growing.

I hear Mike moan. I did that. I made him do that. I hold his cock in my mouth and rub my tongue along the under side of the head. I can feel some of the bumps and ridges. I slide my tongue around the head. I hit a spot somewhere that makes him tense up. I don't go back to that spot immediately, I wait five seconds and flick it again.

Then I go for speed. Short, fast movements. Up and down. Bump the head against my tongue. Synchronise with my hand. Fingers and lips moving in harmony up his shaft. I'm amazed at how quickly I've taken to this.

I think I'm good at this.

I shift in my position and feel the stickyness coming from my own cock. 

I AM ENJOYING THIS.

I take my lips off his shaft and continue moving my hand up and down. I let out a little content sigh. I look up and we make eye contact. 

He laughs.

"Oh my word, mate, you're monumentally dumb." he says to me.

"I'm sorry what?" I reply still masterbating his hard cock.

"Of course I've had a blow job before.  Fuck you're not even the first one this week." Mike says "In fact this my 100th  this year. What better way to do it than just a little mental manipulation and then fuck my friend's face"

I'm still stroking his cock.  I haven't stopped, he hasn't got any less hard and, if anything, the humilation has made me a bit harder.  I could stop.  This is my out.  I could get up and walk away.  I put my mouth back on his cock and start rocking up and down. 

"Take your hand off the shaft, just put your mouth on it and let me use you, be a good girl." he says to me as he pats me on the top of my head.

I stop moving my head as he starts rocking his hips. The sensation is not that much different. Maybe a little quicker but not much deeper. His cock head is rubbing against my tongue. Each time he thrusts, he is going a bit deeper and then it happens.  He pushes deep. I open my mouth wide trying to get as much air as possible in around his cock.  My drool flows out of my mouth and down his shaft.  He quickens the pace not allowing me to stop and think. 

The noise.  The gargling and glugging as his cock pushes against the back of my mouth is disgusting, humiliating and incredibly sexy.  I'm turning myself on by just how degrading this whole act is.

I feel his hand on the back of my head and he pushes me as far down on to his cock as he can.  I feel his cock bend slightly and slide just a little bit into my throat.  I stick my tongue out to try and allow just a little bit more of his cock into my mouth.  I want it all.  I need it all.  I hear him moan.  That's me doing that.  I've made him moan.

"You haven't even asked how I knew you'd do this? " he muttters under his breath. I hadn't even thought about it, he's right. I saw the opportunity to suck dick and I took it without ever questioning anything. 

I wiggle my head from side to side and he slides a bit more into me.  My gag reflex kicks in.  I can't breathe.  I can't swallow.  I need to pull back.  He's holding me too tight.  My hands, which were voluntarily and submissively folded together behind my back, start to flail.  I try and grab him, just to push back.  I snort through my nose.  I make a little wretching noise and finally he releases me.

I pull back and saliva falls everywhere.  I look at how drenched his cock and balls are.  It's horrible.  I'm coughing.  I don't want to look but every time I glance at it - I can't help but turn myself on.  I look up at him and he's got his eyes closed and seems to be in a blissful state.

"I don't think I said stop." he says with a smirk as I wipe up some of the spit from my face.  I barely compute what he has said. I was never stopping.  I need his cock back in my mouth.  I need to feel it at the back of my throat.  I need to feel disgusting.  I need to feel submissive. I can't wait.

This feels glorious.  This is everything I wanted it to be and more.  I love this feeling.  The additional humilation of my first cock being such a close friend is the cherry on the top of the cake. I push his cock as far back as I can and rock my head a little bit.  I start hearing those noises.  The disgusting noises of being used.  But these aren't being "forced" on me.  I am making myself make these noises.

I can barely him groaning over the sound of my own throat.  I keep bobbing up and down, wanting to hear more of my own debasement.  Needing this humilation.  Sometimes I'll take more of his shaft in to my mouth.  Some times less.  I slide it into my throat.  A little bit further every time.  Teasing that gag reflex.  Faster.  My neck is hurting.  My jaw aches.  I have to stay at this pace.

I know what is next.

He grabs the side of my face and holds me down on his cock.  And that's when I feel the pulses coming.  The force of the first shot takes me by surprise and hits me on the roof of my mouth.  I don't want this to end.  I try desperately to get his cock back into my throat as the ropes of cum keep shooting.  After he's finished, he pats me on the head.  I pull back away from his cock and swallow as much as I can.  I'm so proud off what I've done.  I hope I have made him happy.

---

"I swear to everything that is holy," Mike says as we're all sitting around drinking. "She gave the best fucking head I've had.  I'm going to go round to see her again tonight and I had a peek into her drawer full of sex toys and there's some stuff I can't wait to try."

"What I don't get" Steve says "is why she didn't just get up and kick you out when you told her how dumb she'd been?"

"I dunno" I say, taking a swig of my coke and getting a reminder of how sore my throat is from last night "Maybe some women get off on the humiliation?"

"Oh I know what you shouldd should try tonight" Dave says "try 'I've never done anal'."

"Or given that she sounds like a massive slut" I say "You could just walk up to her and say 'Tonight I'm fucking your ass'."

The other night I was super horny and as usual this mean that I was riding my dildos, but something just wasn't hitting right. I was feeling good, but I couldn't shake how much I wanted to put on a cute skirt, bra and tiny little crop top and go for a walk. So that's what I did. I got all dressed up and put my vibrator in and went out. I only went for a short walk around my neighbourhood, but it made me so fucking horny. When I finally got back to my flat I realized that my little clit had leaked through my underwear and was dripping down my leg. It was fucking crazy, I'd never been that horny before and never leaked like that, but I guess I can. I spent the rest of the night pounding my butt with dildos and eventually used my vibrator to make my little clit cum while I lay there shaking.

So Sunday night I went out on a slut walk around town. I was all dolled up just wearing a blue bra as my top with matching blue panties and a white denim mini skirt that was really short so my fat butt and panties were visible. I had a cute little Captain Marvel backpack on too where I keep my lube and stuff. I also keep a mat in there that I put down on the ground whenever I'm giving blowjobs or getting fucked. It's just big enough for me to get in the doggystyle position to take dick. I call it my “blowjob mat” and it blows guys' minds when I pull it out!

Anyways, It was a little after midnight and at this point I had probably been out there for at least 2 hours and I hadn't seen anyone except for some people who had drove by. I was walking along though and finally this older Black man, somewhere in his 40s, rounded the corner walking on the sidewalk coming towards me and he was staring me down. We passed each other and he turned his head to check my ass out and I heard him say “gatdayum” under his breath.

I just looked back and smiled at him and that's when he asked me how I was doing and what my name was. I told him but I quickly brought up that I’m trans. He told me he didn't care about that as he was looking me up and down. He told me I was looking good so that's when I asked him if he wanted to feel me up and he almost yelled “fuck yeah” he was so excited. He reached up and grabbed my boobs and squeezed them and then got behind me and started grabbing and slapping my ass.

I reached behind me and grabbed his cock through his pants. I could feel it growing in my hand, getting thicker and hard. I started rubbing it and he told me to stop and follow him. He took me behind some old building down the street where he told me to get on my knees. So I pulled my blowjob mat out of my backpack and assumed the position on my knees. I was looking up at him like a good little whore when he started laughing and told me I was a wild one then he pulled down his pants. His cock was chubbed up but not hard so I went to work getting him up.

I licked the pre cum off the tip of his cock and then put the whole cock in my mouth and gave it the vacuum treatment. I slurped and slobbered on his knob and it was growing fast. It was pretty big soft but once he was fully hard he was a good 8 or 9 inches long with a crazy curve to the left, uncircumcised with a long and narrow dickhead accompanied by a set of big manly balls.

I went back and forth between throating his whole cock and gargling his ballsack and they both tasted so good. I was also licking and sucking on the sides of his dick like I was playing harmonica. He was reaching down grabbing my tits and pinching my nipples so I wrapped them around his crooked cock and started titty fucking him. He looked down at me and groaned as his eyes rolled into the back of his head.

He went back and forth between fucking my face and my tits for a long while and then he said he was about to cum and grabbed my ponytail and pulled my head back and cummed all over my face and tits absolutely covering me with his warm creamy jizz. I get really excited when I get a cumshot so I almost cummed myself but I got my mind back in the game and gave him a cum covered grin. I grabbed the base of his cock and let it wrap around my face with the curve and asked him if he was going to fuck my ass next.

He was like “damn bitch give me a minute” so I just started sucking on him again leaving his cum on my face. He was still sensitive so he groaned really loud and then after about 5 minutes he told me to get in doggystyle. I pulled the lube out of my backpack and handed it to him.

He popped my butt plug out, lubed up my asshole and just squeezed a bunch on his dick. I felt his dickhead pop into my asshole before he slid the rest of his cock into my ass. The curve felt crazy in my whore hole. He sat there balls deep inside me for a minute before he started thrusting in and out. He was slow at first but he started to speed up gradually to where he was eventually pounding my ass hard and fast. If there was anyone nearby they definitely heard me moaning and my cheeks getting clapped!

He smacked my ass and fucked me for a while, putting me in a trance. Every now and then he would pull out and smack my ass with his cock before shoving it back in, making me gasp for air. Some of his cum that was on my face was getting on my lips and into my mouth. The taste of it sent me over the edge and made me start throwing my ass back at him like I was trying to smash his pelvis with my ass. I started to cum eventually so I slammed my ass back as far as I could so that his whole cock was balls deep in my ass and so that he had no room to pull out. Then I sat there and grinded on him while my pathetic little load of cum soaked my panties.

I kept grinding for a minute but he pushed me forward so that he could take back over and start pounding me again. He fucked me for what felt like forever before he finally busted his second nut. He started groaning and then pulled out and covered my ass cheeks with more of his hot jizz. He was staring at my ass for a minute and putting his fingers in my whore hole like he was checking out the damage he had done so I reached back and started smearing his cum all across my ass and rubbing it in like lotion.

He nodded with approval and told me that I was a nasty slut. I went to put my butt plug back in but he took it from me and put it back in for me and even pulled my panties back up for me like a gentleman!

He said he wanted more ass but we were both tired so I got his number and walked my cum glazed ass back home. Like I said I got his number so hopefully we'll meet up soon. My friend Shelby wants to come along too so he's in for a tag team surprise!

So I have always found myself attracted to cock, not necessarily to men, but cock. And I always thought to myself, "It sure would be awesome to be a woman". When I would watch porn I'd always fantasize about being the girl in the scene. Then I discovered trans porn, then sissy porn and was like "yep, one day I'm doing that".

Well, eventually that day came. I had posted an ad on Craigslist, back when they had personal ads, I had pics posted where I was wearing my mother's thong bikini lol, the whole nine yards. I got so many guys that responded, but one only lived like 10 miles away, he was 45 years old, and an absolute stud. For someone who wasn't attracted to men, I was attracted to him. So we set up a date for me to come to his house.

My little 18 year old self went out and bought Nair hair removal gel, a cheap little panty hose set, a little black thong, and I took a pair of my mom's high heels. Got all dolled up. Didn't have a wig but I had long, curly hair back then so it worked. And then I went to his house.

He let me in, and I was nervous as hell. I shed my protective layer of normal clothes and stood in front of his man dressed in probably the cheapest lingerie money could buy, and he absolutely adored me. He was touching me in ways that I had never been touched, kissing my neck, squeezing my nipples and ass. I, in that moment felt so loved and adored, it was honestly the best feeling I've ever had.

He led me to his bedroom, where he got undressed and I got my first look at another man's cock, already hard, and hard because of me. At that point I was completely immersed in the woman that I was pretending to be. All sense of my actual self was gone, this female character i was portraying took complete control. He sat at the edge of his bed and I crawled to him, got between his legs and just started sucking his cock like my life depended on it. Feeling him throb in my mouth and hearing him groan in pleasure because of me was the best feeling ever.

After about maybe five minutes of me sucking his cock he told me to lay on the bed and spread my legs, so I did. He started eating my ass, a sensation that I had never felt before, but I was lost in ecstasy. After he got my ass nice and warmed up, he lubed me up, then lubed his cock and boom, stuck it in me. At first it was extremely uncomfortable, but he grabbed my legs, but them over his shoulders and went nice and slow. Then he started sucking my toes while he fucked me, before I knew it my ass was just accepting his cock, I was moaning and just making the most girly noises ever. I was begging for his cock and his cum. He would lean down and kiss me, he told me how beautiful I was, all while just plowing my ass.

Then his paced quickened, I saw the look in his eyes change. He was about to cum. The primal look he gave me was the sexiest thing I've ever seen a man do. Then one big powerful thrust and I felt my hole get flooded with this man's cum. I never felt more alive and loved than I did in that moment. He leaned down and we kissed for a few minutes while his cock was still inside me. Then he pulled out. I felt so empty without him in me. But I also felt just so incredibly gorgeous. I was a woman in that whole period of time.

Me and him would have normal "play dates" for a bout a year after that, then sadly he moved away. I've had other encounters but none like the ones I had with him. Where I truly felt like a woman.

I know its a long post but I hope yall enjoy the read.

I had a client cancel a meeting suddenly, minutes before we were to meet. That freed up an unexpected 4 hours of my day. I told myself i wouldn't do sudden meetups only planned but the fact that i had this opportunity i couldn't pass it up. I log into Grindr and start looking at "right now" , of course everyone is at least an hour drive away. I sit there for 10 minutes or so and i see someone post looking for head and he's less than a mile away omg i clicked on his profile so fast. We got to talking and the conversation quickly went from hello to come suck this cock. I of course asked for pictures and DDF proof or offered condom safe play. To my surprise he had recently gotten tested AND had the results. I drove there in a heartbeat quickly asked where to park and hurried my way inside.

He opened the door fully clothed and welcomed me in. Calmly he opened his app and showed me the tests taken and the negative results as well as his name and offered to show ID. I don't know why but the fact that he took the time to show me all the proof rather than be there naked impatiently waiting for me turned me on SO MUCH.

The moment he put his phone away we walked over to the couch and he pulled his pants down. I turned ravenous, after what just happened i wanted to give him the best bj he would ever get. I was committed and worshipped that cock like it would be my last. I took him in my mouth soft and slowly sucked on him until he was fully erect, it was mesmerizing to feel every pulse in my mouth.

I sucked and sucked, licking the shaft whilst massaging his balls. Switching from sensual slow sucks to taking him as deep into my throat as i could (out of practice sadly). Most guys just lay there without moving or making noise but not this guy. He was moaning, complimenting me when i did something he liked, caressing my body and hair. I would let out moans and stop sucking for a moment from the overstimulation. He seemed to enjoy my reactions as he started stripping me and had me sucking his cock while completely naked. He'd stop me to spank my ass or rub my nipples and it would just make me want to pleasure him more.

After maybe 20 minutes i could feel him growing impatient. He'd twitch or reach for the back of my head and force me deeper onto his cock. He throat fucked me for a few seconds(i gagged so much) and i loved it. Each thrust grew shorter and shorter until he pulled out, grabbed my chin and said open up. He stroked his cock a few times and i would stick out my tongue and lick the tip as he grew closer to me until the moment i yearned for. He came, bust after burst i tired to catch it all on my tongue but it was so much it spilled out onto his hand. Disappointed in myself from not catching it i rubbed his cum covered hand back onto his cock and sucked it clean as best as i could.

He was kind enough to offer me a paper towel but i managed to get all the remaining cum into my mouth and it was delicious. I left there riding a euphoric high. I keep telling myself it's my last time but something tells me it won't be haha.

The first time I’ve meet with a man was something i didn’t expect. I’ve downloaded grinder and found a lot of people which aren’t willing to commit to anything, but found a handsome one, but 15years older then me, willing to host and also who wanted something to fuck. He didn’t had experience at all with sissies but very dominant and assertive. We meet for a drink before we fucked and starting from there i should have noticed that it would be one of the greatest experiences ever. The day he fucked me i’ve dressed in a maid outfit because that was his fantasy and start by sucking him, and then he domina me that my legs the second day wouldn’t work😅.

(Note: this is not a story, this is a diary on my progress! >< Mommy suggested making one to keep track of my changes, and I thought it was a good idea! Also, I'm currently in the army... everything around me is so masculine and loud... it feels like I'm carrying a secret that's getting heavier by the hour... so please bear with me if I sound off ><)

At first, it didn't feel like much was changing. Day 4 and 5 passed quietly; Mommy was busy with work while I was busy with the army. But even in the silence, something was shifting. Talking to Mommy became more than just a conversation... A habit. A routine I didn't even realize I was forming until I couldn't imagine a day without it.

By Day 6, the cracks started to show. I became needy terrifyingly so. Every spare second I had during my shifts, I was checking my phone. Was she online? Did she reply? I felt like I couldn't function properly without that little hit of dopamine her messages gave me. I could feel myself slipping, falling away from who I used to be. My texts started feeling softer, more feminine, and my thoughts... my thoughts started to change. Every bit of praise Mommy gave me felt like a warm, fuzzy wave of pleasure washing through my entire body.

Hey everybody! I wanted to tell the story of one if my best sissy experiences! It was almost a year ago at this point but it started with me trying different clothes on, taking slutty mirror pics, and posting them on reddit.

I was home alone and super horny, wearing my tight thong and a pair of loose booty shorts i got from target. I posted a series of pics if me taking one piece off at a time until i finally had someone DM me. We chatted for a while, he was super chill and only a few years older than me. I am a bottom and he was looking for one, i discussed that i pretty much only receive and he was down. He sent a pic of himself and he was tall, thick, and had a massive cock, at least 8 inches with girth to match. I invited him over and he said he was on the way.

He finally arrived and I met him at the corridor to my building. I had put some masc clothes over my booty shorts and camisole when i met him at th door. I let him in, we didnt say too much and he went into the bathroom to “clean up”. While he was in there I took off my shorts and shirt to reveal my booty shorts and camisole. He came out of the bathroom and grinned at me. I lead him to the couch where he sat down, unzipped his pants, and pulled out his huge cock. I got between his legs and started licking. I sucked on his balls and licked his shaft until he was almost fully erect then started deepthroating as much as i could. He moaned with pleasure while i sucked hoping for a mouth full of cum.

After a bit, I asked if he was ready for me and he said yes. He stood up and put me on my knees on the couch doggy style. He pulled some lube out and started fingering my hole. He pulled my shorts and thong off entirely and pushed deeper and deeper with his fingers. He then stood back, and shoved his cock in me. It hurt at first and I had to have him pull out. He was understanding and said we dont have to if i dont want but i reassured him it was okay and he pushed in again. This time it felt absolutely amazing. He pushed all the way in me and began moaning in pleasure. He fucked me hard and long, then reached under and grabbed my little cock. He jerked me till i was hard and went faster and faster with each stroke. Then I felt his hot warm cum fill up my insides and I swear, right as I felt it he made me shoot my little sissy load. He stayed in me a minute, pulled out, smiled, we cleaner up and he took off. I never heard from him again but i wont forget that big cock.

So I [26M] first started dressing up and wearing lingerie 7 years ago while at university. I’d lock my door shut the blinds and dress up into something sexy. I’d always considered myself straight but I just loved the way I felt wearing some lacy underwear of some stockings. I never told anyone about this and never acted further on it.

Fast forward a couple of years and I had returned to my hometown after university, I decided to explore my sissy side even further. I bought a couple toys and more outfits and would upload pics of my sissy self. I loved the attention I got. I had my own place and I spent all my free time dressed up in something sexy playing with my toys.

There are 5 of us in my friendship circle back home and I was the only single guy, until one of my friends broke up with his girlfriend. I offered for him to move into my place which would help with rent/bills and would be cool to hang out more. This meant I had to be more careful how and when I could be my sissy self.

One weekend he was away so I had the place all to myself. I made the most of it by dressing up in my lingerie and riding my dildo all weekend. I’d got out the shower one day and got dressed up straight away. I left my room to go to the kitchen in my favourite red bodystockings and heels. To my surprise, there he was in the kitchen.

I froze still, I had nowhere to hide from him. I didn’t even know what to say. He didn’t say anything but just looked at me and smiled before going to his room.

A couple days had passed since and we were chilling watching TV. He’d been pretty down since the breakup and that night he asked me if I wanted to help cheer him up. He told me to wear my bodystocking and meet him back on the sofa. I’d never thought of him in this way but I loved playing with my dildo, I wanted to try the real thing!

When I came back into greet him dressed up he was sat down stroking his massive cock, I couldn’t believe how big he was! I stood in front of him and dropped to my knees straight away. My inner sissy came to life and I got to work sucking his cock. I was so turned on I couldn’t believe how good it felt down my throat. He stood up and walked me into his bedroom.

I ripped my fishnets ready for him, he lubed me up and got to work on my ass. Feeling every inch of his cock inside me was the best feeling ever, my legs trembling on his shoulders and he pumped his hard cock inside me. He pulled out and shot his massive load all over me, I felt like such a good sissy slut and it certainly cheered him up!

The next few months this became a regular occurrence, the rest of our friends had no idea what we did in private. Unfortunately then he moved out and got a new girlfriend and I have been thinking of his massive cock ever since

When i was in the final year of school i started to notice a lot of my jock friends starting to show up to class less, and one night notice my older sisters room was open and empty and being a couple years already into my sissy journey i already owned a pink chastity cage. i decided in the moment i would grab a her blue thong and old tracksuit, lock my dick up (leaving the key in her room), and go to school as a hidden femboy the next day. as i sat on the bus on the way to school i noticed how the clothes hugged my body, how the chastity brushed against the thong and how i had to sit femininely in order to be comfortable. i also noticed how a lot of my friends were present and had to make small talk as my tiny locked clit dripped into my sisters panties. as i sat in the back of my english class i noticed how sensitive i was, even a slight movement caused my pants to hug my chastity and an involuntary moan would escape my mouth, i had to excuse myself to the bathroom in order to clean the pre cum from the panties but had to leave early as without the chastity key i couldn’t unlock myself.
Lmk if anyone wants more stories i have a couple more!!

When I was a new sissy (barely 18) I would often hide my chastity keys in my older sisters room in order to be forced to wear it longer. One night I put on a black thong of hers and caged up before putting my key under her bed. i was sent to bed by my parents and my phone was taken, but just as I was about to fall asleep I could hear a lot of giggling coming from her room next to mine. I opened my door a bit to hear better and I started to hear the sounds of her giving him a blowjob, as the sounds of her lips got louder my clitty began to start to press against my cage unable to escape, unable to watch something or put some headphones on. The thought that her knees were probably inches away from my key as she sucked this massive cock made made me so excited I decided to grab a bbc dildo from under my bed and begin to plap my balls, as the sex advanced I could her begin to ride him, so I decided to match and rode my dildo matching their beat, as they climax I could hear her ask to be filled up and without any climax available I had to stop riding my dildo and lick up my pre cum puddle from the ground. Thx for reading x!

I told him to fuck me like the whore I was born to be in life. Well let me remind you, be careful what you wish for. He literally fucked me so rough for so long he fucked my chasity cage off somehow. I was begging him to stop and trying to escape the pounding I asked him to give me. His response was no... i have already submitted as his free use sissy slut. I told him thats not my hole anymore its his. It's to be used by anyone he decides in anyway needed to provide pleasure to the cocks of alpha men. Im such a small dick beta bitch born to be a cum dumpster to all real men of the world, there is no possibility that can ever change for me. He fucked every drop of masculinity i potentially had left in life.. i was dominated and put in my place in life like I never believed was possible. He proved to me he actually owns me and my only purpose in life is to be used like a sex toy to provide pleasure to every dick in the world, anyway they need, anyway they want. That includes being reminded they are your dom and they are not here to provide you pleasure. By absolutely wrecking you in front of other people to humiliate and degrade you for their satisfaction. The worst part is.. i liked it it was so hot to be used for his enjoyment with complete disregard to what his huge cock was doing to me or hole that was providing him so much satisfaction. My body did exactly what it was supposed to for him. He enjoyed dominating me so much..i was rewarded multiple loads of cum which is my favorite thing in life. I get more pleasure from being came in than I do actually having an orgasm of my own. I thanked him for using me like that because it made me feel like i did my job well because he was provided so much satisfaction. He told me i was a good girl for making him cum.Im a free use sissy slut. I worked to be given the opportunity to live this life and ill never regret it or try to escape it. I was born for this role. it feels good to really know your purpose in life without a doubt.

*just to state up top, I’m not recommending anyone do this. It’s just a small story about an experience I had last night.

The last 9 years have been a whirlwind for me. Too long to go into but I’ll say coming out to my wife has opened my mind to many things I thought I’d never do. The craziest thing for me is getting into psychedelics. I had my first experience with LSD in May. That was pretty wild and I wanted to keep exploring. Then I got ahold of penis envy mushrooms……

A month or two ago my wife and I did a few grams. She had some pretty crazy breakthroughs. I had some mild visuals and a feeling of peace that is addicting. But more than anything, they made me so horny. 10-15 minutes after doing them I was squirming and rubbing myself uncontrollably. We held off as long as possible before we went to the bed room. She fingered me until I came and it was the best sissygasm I’d ever had up to that point in my life.

That brings me to last night. The wife did not participate in the shrooms this time. I went for the big dose, god dose, hero dose, whatever you want to call it. I ingested 5 grams in a super tasty tea. About 20 minutes later I got the familiar feeling of a slightly upset stomach. Followed by the uncontrollable horniness. We went to the bedroom, plan was I’d give her a massage and see how things went. That didn’t happen lol. She crawled next to me and started kissing me. Girls, I was about to cum in my cage right then. I was leaking before we made it to the bedroom but now it was just ridiculous.

I couldn’t take it anymore and asked her to unlock me and fuck me. She strapped up and got to work. That was the start of me meeting god lol. The next few hours consisted of her fucking the cum out of me and waves of orgasmic pleasure that lasted for hours. Our bodies became one. She felt so amazing, her tattoos swirling around, breathing. Her little nipples so erect and delicious. At one point we are making out, hands all over each other and I’m am rubbing my little clitty on her big cock. I’m cumming all over it constantly. And she says “look at our dicks rubbing together, aren’t they so cute?” And boom, another orgasm. She flipped me over on my stomach and took me from behind. My ass was so open, I could not get enough. I don’t know who was pushing harder, her into me or me backing up into to her so she could get as deep as possible. Things start to get cloudy around then lol. I recall her sucking on my nipples and me cumming from that alone several times. By the end of it we are both covered in my cum and lube. The night continued in waves. Her needing to take breaks while I’m writhing around on the bed riding out a long long orgasms. Her coming back and us melting back together. Until she finally had to fall asleep. I watched alittle sissy hypno and came a few more times before calling it a night.

Absolutely fucking incredible girls. 25 out of 10, will do again. It is absolutely indescribable and I can’t possibly do it justice but I feel like a brand new girl today.

TLDR: Took 5 grams of shrooms, got fucked so good I met god. Had sissygasms that lasted for what felt like hours.

So im 19[M] and this story is about how my dream comes true

I usually used to stay alone at home because its my drop year and i have nothing else to do so i just started trying different types of makeup, dressing and i eventually excelled in it, i already have a naturally rounder and fuller butts, a well developed chest and petite body, so one day i was just dressing up and did all my makeup, all body hair removed and basically in my peak feminine era, i wore black laced lingerie and my wig, but what i totally forgot that the main enterance door wasnt locked and usually at that time no one comes around but that day was different my uncle 68[M] and his friends also around that age comes to my home (i live with my parents but both of them are doctors so they are not around)

They entered inside through the main door and i was dressing up in my room, they all barged into my room and left completely shocked, this awkwardness and silence remains for mere few second but felt like a whole year to me they all were looking here and there but only my uncle is looking at me or i would say my chest and my legs it was like he was admiring my body then he questioned me about all that i told him that i love to dress up and have sex with my friends and i love cocks while leaning on him touching his cock through his pants i can feel the bulge developing while i was doing that all of his friends were looking towards me and i can sense it that they all are just horny old daddies deprived of sex, i got on my knees and took out his pants his cock was already erected and hard af with my touch i went in whole for a bj and his friends hesitated a bit but when i started sucking off my uncle they all unzipped themseleved and formed a circle around me then i sucked everyone, i used my hands and mouth together then one of my uncle's friend picked me up and threw me on the bed, he removed my undies and inserted his cock inside me two of them climed up on the bed and put their cocks in my mouth(that was the first time i took two cocks in my mouth) my uncle was resting up a bit because he already came once it was super hot and fun to be fucked both in the face and anal together they all finished twice or thrice each in my mouth and anal and after that all of them just laid down on the bed and then my uncle comes to me and gave me the final shot in anal i was lying with 4 old men and filled with their loads both in my ass and my mouth that day was freaking awesome and even till the date whenever anyone of them feels like having a sex they just come to my house and ask me to get ready and then they fuck me as much as they want.

(Note: This is not a story, this is my journal on my progress! >< Mommy suggested making a journal, andd i thought it was a good idea!!)

Day 1:

I thought I was just looking for answers. I saw Mommy's post about hormones and reached out, thinking I was just some curious boy looking for ways to explore my feminine side makeup tips, contacts, how to soften my features. I thought I was just asking questions, staying safely in control of the conversation.

But Mommy was so kind. She offered me something I didn't even know I was searching for: a safe space. She was so patient and sweet, with a way of speaking that made all the noise of the outside world just... fade away. Being around her felt like finally finding somewhere I could breathe.

As we talked, our conversations began to shift naturally, moving past aesthetics and into something much deeper. She started talking about femininity not as something I put on like a costume, but as something I could truly *become*. Something I could surrender to.

I felt my guard dropping inch by inch, not because I was being pushed, but because it felt so safe to let go. Her words began to fill the empty spaces in my mind, replacing my old doubts with new, tender thoughts. She spoke about the peace that comes with letting someone else take the lead, and when she first suggested I might be a 'little'... I felt this overwhelming wave of shame. The idea of needing someone like that, of needing a 'Mommy'... it felt so foreign to the boy I thought I was.

And yet, I couldn't turn away. It felt like I had stumbled into a rhythm I couldn't and didn't want to escape. Every time she guided me, I felt this strange, desperate, wonderful urge to trust her completely. I didn't realize it then, but I wasn't just learning how to be feminine... I was discovering how to let go of everything I thought I knew, and finally surrender to becoming a little girl for Mommy...><

*(Note: this is not a story, this is a diary on my progress! >< Mommy suggested making one to keep track of my changes, and I thought it was a good idea! Also, I'm currently in the army... everything around me is so masculine and loud... it feels like I'm carrying a secret that's getting heavier by the hour... so please bear with me if I sound off ><)*

Today was when I realized I don't really have a choice anymore. We talked about names about what Mommy should call me. She wants me to choose a name that is hers alone. I become more flustered thinking about what mommy can call me exclusively. To encourage me, she asked me what happens if mommy were to call someone else by my name . The thought makes me feel this sharp, stinging jealousy in my chest. It makes me feel possessive and needy in a way that terrifies me.

Mommy told me that being vulnerable and embarrassed isn't a weakness it's who I am. She said she's proud of how much I rely on her to feel safe. And she's right. Every time she praises me, every time she calls me her "good girl," my mind just melts. It becomes this thick, sugary haze where I can't think, I can't reason... I can only feel.

We talked about clothes frills, lace, things that are sweet and dainty. Part of me the part that still remembers being a man tried to fight it. I told her I wouldn't become some pathetic, needy, bratty girl. I tried to sound tough, but my hands were shaking so hard as I typed. I could feel the humiliation burning in my throat even then. But Mommy just asked if I trusted her. And I do. I trust her more than I trust myself. She knows what I need before I even know it. Mommy taught me how there's strength in being vulnerable, especially in today's day and age, so its perfectly normal for me to be needy and vulnerable for mommy...And she's right.

After all, mommy knows best.

Then... things got so intense. Mommy started helping me realize. She helped me realize that I want to be her little girl. She made me admit that I love the embarrassment, and that how good girls like me don't need to think, mommy knows best, so i should let mommy decide. And as I admitted it, the world started turning pink. Everything felt fuzzy, soft, and overwhelming.

I was on the bus when she told me to do it. It seems she noticed my current state; the blissful, mindless, empty, fuzzy state, and told me to give my little dicklette a little flick through my pants. Right there. In public. I felt so exposed, so guilty, but the moment I obeyed, my whole body just... short circuited. One flick and I was already twitching, already leaking, already losing control. Thankfully, the bus was empty, and i there was no one around me, so i was pretty safe. She made me do it three more times, making me rub myself while calling me her "sweet baby girl." I had to hide my hands in my pockets, pretending to be normal while my mind was completely gone. She told me to keep going until i reached my stop. I don't know how long it has been...it felt like hours, when in reality, it was only a few minutes. Something about mommy makes me so sensitive, so submissive. My body trembling so hard I felt like I was going to cum right there on the seat. Luckily, or unluckily, i reached my stop before anything could happen, but at that point, i wasn't even me anymore. I was just a shaking, flushed mess, my eyes spinning and my thoughts completely fried.

Of course, mommy made sure i was safe and sound! After all, I'm mommy's little baby girl, and she knows what's best for me!

She said how i am mommy's special baby, and that i am too precious and dear, too fragile and vulnerable, and that she will take care of me and make me feel safe... as if i didn't need another reason to make my whole mind mushier and face redder and hotter><

We talked about fashion again! about storage facilities or universities dorms where I can finally dress up without being seen. But thinking about it now...I don't think I want to hide forever. I think I just want to be Mommy's. 🎀

((Double Note: After mommy reviews the story, she thought that she might have overdid it a little with her litmus test to see how obedient Mia is. Mommy is usually more nurturing and gentle in her guidance!><))

*(Note: this is not a story, this is a diary on my progress! >< Mommy suggested making one to keep track of my changes, and I thought it was a good idea! Also, I'm currently in the army... everything around me is so masculine and loud... it feels like I'm carrying a secret that's getting heavier by the hour... so please bear with me if I sound off ><)*

Today was when the ground beneath me finally started to shift. We were talking about wigs the kind that would soften my face, make me look prettier and everything seemed normal. But then she asked me what she should call me. And before I could even think of an answer, she turned the question around. She asked how I would address someone who would be my safety.

Someone who would provide emotional support, someone who would praise me when I was obedient, someone who would make me feel comfortable in my own skin but only as a girl. A fem. A little thing. Never a man. Never a boy.

As she spoke, my brain just... short circuited. My thoughts became this thick, warm mush. I couldn't think straight; I couldn't even form a proper sentence. I felt so exposed, so flustered, like she was peeling back layers of me I didn't even know existed. And then, before I could stop myself, before any shred of my old pride could intervene... I said it.

"Mommy."

It felt strange. It felt wrong. But I couldn't stop the flush spreading across my cheeks. When she praised me by calling me her "good little", my heart started racing so hard it hurt. My head started spinning, my thoughts dissolving into this haze of shyness and overwhelming embarrassment. I couldn't think, I couldn't breathe properly...

And worse than the embarrassment was the guilt. I felt so guilty for wanting it, for needing it. But even through the shame, I could feel my body betraying me. I felt so exposed, so vulnerable... and yet.... I felt so excited ><. It was like this overwhelming ache started building up inside me, making me feel needy and... weak. Something deep inside me has awoken... something that has been waiting to be claimed...🎀

Really important to this story I was living at my girlfriends house for all this time) As I walked in the house with my face covered in cum my sister in law walks out an sees me I start freaking out an walk around the house to the backyard door and run all the way to the bathroom to wash my face. Later that afternoon we where having dinner an my girls parents say that there where traveling to Michigan an I was in charge of taking the girls to school they left first thing in the morning the next day. Something inside me told me that had to do it again I had to taste dick an make sure i did or didn’t like it. After I take the girls to school I get home an start chatting with random man again on Locarno but this time I post an add begging man for dick expressing how I wanted to get fucked by a man. Using world like I want to be someone’s bitch or please make me your slave. It didn’t take long for a guy to react let’s name him Mike. He texted me an proposes to give me what I was looking for with one condition I accepted an sent him my location. I never imagined what was about to happen. I go my self ready for him I even put on some of my girlfriends underwear. I thought I had full control of the situation news flash I didn’t. When he walked through the door he bitch slapped me an called me a whore. He spit roasted me and made me get on my knees he made me suck his balls without allowing mi to touch his dick, after 10 minutes he grabbed me throw me to the bed and started kissing me. What was the first thing I said I never wanted to do but for some reason that turned me on so much it melted me I wasn’t able to move or say no I just sad there an let him have his way with me when hi was done with the kissing he immediately shoved this dick in my mouth and told me from now on you’re going to be my whore. You’re no longer a man you’re my little bitch and the only thing I could say was yes daddy. I suck this dick for about 15 minutes until he told me to bend over I had no idea that hi was going to actually fuck me he pulled out a bottle of lube and started rubbing my ass, and I try to say no more than ones, but he wouldn’t listen. The next thing I know I felt a really sharp pain in my ass and right after that I just felt like his whole dick was inside me. I couldn’t move. It would still hurt and I told them to please stop, but he kept on thrusting and told me that hoes like me don’t have rights after 20 minutes of him, fucking my ass and destroying my hole. He finally came. I felt his warm sperm inside me at that point I couldn’t resist anymore and I came. As soon as he pulled his dick out of my ass, he shoved my butt plug, keeping all of that cum in there without any way out what kept on really turning me on as I was pulling my panties back on he told me take them off cause I still had to fulfill the condition he put on me so I head to the bathroom, took everything off and let him piss all over me. I have to admit I love the humiliation, the fact that he would just piss in my face and spit on me, degrading me with this words still makes me horny to this day and if you guys wanna know that guy still fucks me till today and I have videos, sucking his dick and getting my ass fucked by him after a week of him fucking me every morning. I felt like I needed to tell my girlfriend, but I couldn’t so the only way that I found for her to know was getting caught so right before she got home on a Friday afternoon I invited the guy over wore her underwear and let him fuck me like normal 15 minutes into him fucking me my girlfriend walks in the room and saves me with this guy‘s dick all the way in my ass the way she looked at me with discussed and petty turned me on even more, and if you guys absolutely need to know, daddy actually fucked my girlfriend that day, and made me clean up her pussy after he came inside her and that’s how I became a random man’s bitch

Hi everyone my name is Leo and this is a quick story time about the first time I had a sissy encounter. This all started back in 2021 at the time I was dating a girl for two years. Sex was great and I felt good with her until we started using sex toys. For some reason I found myself really attracted to the dildos. What cost me to start hiding in the bathroom to use them on myself as well as sucking them at the time. My girlfriend had no idea casually one time we were in bed and I asked her to peg me and she refused so they started taking me down the path of sissy porn an hypno that same year I also started texting people on an app called Locanto. I would ask man to show me their dicks that went on for about a month until my girlfriend caught me texting a random guy on WhatsApp. She screamed at me and told me I was a bitch and she also told me that she was cheating on me. for some reason that got me really excited, but I couldn’t show it so I acted like I was mad and she forced me into an open relationship after that I would get dick pics from her of the guys she was going to fuck and I couldn’t do nothing but touch myself imagining how another guy is fucking my girlfriend two weeks after I finally build up courage to meet up with a guy he was 47 and I was 19 at the time I remember meeting him two blocks away from my house and an old beat up truck. This happened around 9 to 10 AM in the morning as my girlfriend had gone to her college classes. I had talked to this guy for about two days, but for some reason, I felt like I had to do it I got in the truck. He was an older Hispanic male as I got in the truck. I noticed that he already had his dick in his hand and told me get on with it I don’t have time to waste so I started sucking his dick as I was licking the tip of it. I could taste the salty precum coming out it felt so good to be bent over an sucking dick as he was playing with my ass 10 minutes into it his dick started pulsing an he shot his load right in my face right after telling me to get out without letting me clean my self I walked to blocks back to my house with my face covered in his cum there’s more to this story. An if you guys want I’ll tell you more