r/transstoriesgonewild

Back when we started chatting she mentioned both her inexperience sexually and hinted that she has a fairly high sex drive. She's had 1 boyfriend before me, he didnt like giving her a bj, shes to big to give anal so in the end he just wanked her off every now and again. Mostly their sexual relationship was her sucking him and him fucking her. I have always loved being the main pleasure giver but have never been with anyone other than cis women and she seemed kinda sad when talking about how he couldn't be bothered so as we started approaching the subject I said I would give everything she wanted a go at least once. Shes blonde, petite build and gorgeous face, fake D tits and a huge girlcock. Like this thing is at least 9/10 inchs long and thickkk, pretty much her forearm. We tried anal, no.. Just no, not happening. Then we tried me giving her a bj and she loved it. Turns out i have an almost non existent gag reflex (I did watch some tutorial videos and learned the breathing technique and a few good positions for angle and we added a little lube. The first 3 times I gave her a bj we sort of agreed it was practice, she'd give me hints and tips on how to make it feel better and I got my muscle memory accustomed to the rhythm. She became this completely different women, confidence over flowing, gradually becoming more assertive and dominant. The time between her initiating for it started to become less and the bj was becoming more intense. One day a couple of weeks later I came home from work, her full dressed up for me in the sexiest/slutiest outfit and asked me if we could take it up a level, shes been researching a few things she'd really wants to try and asked if I would indulge her request but most importantly give 110% effort. I raised an eyebrow and said yes but little did i know what I was in for. She had bought some throat anesthetic/numbing spray, bed restraints and a mouth guard that holds my mouth open. Yes, she wanted to try proper deepthroat training me with the intention of not only getting her full massive cock down my throat but finish by facefucking me in the 69er position. It was brutal, nice, but brutal. However after a slow start to help me get used to it a little and some positive encouragement followed by... well I was restrained to the bed, mouth completly numb and held open and the more I struggled but saying I was ok to continue the more confident she became. She just kind of let loose in the end and I held on to my life with everything I had untill she orgasumed. She loved the experience, said it was the best experience shes ever had and well now shes addicted. For the last almost 4 weeks every day she initiates with the sole intention of me sucking her, no hands allowed and to completion, this is the minimum. Some days its facefucking, some days she wants it slow and to last, some days im to make her cum more than once in that single session and some days I sucked her more than once. Its crazy, I love it but at the same time its exhausting! Its not that shes long, although bringing it down to 8inchs would help its the thickness thats hard to deal with. Ive said its a struggle and see can see it but her eyes light eye and the look on her face when I give the nod of approval is amazing that I cant help but want to do it. The times we've done a 69er with bed restraints and mouth guard is where she really goes for it, after the warm up she goes from hard and fast to all the way in and stops, holding it there and towards the end its hard fast and all the way. Its brutal but then for the rest of the night shes in the best ever mood, cant stop going on about it and being loving. Like I said, I like it but its brutal.

That is the first thing he said after he found out. His hands were still on my waist, our lips were still wet from kissing each other, and he was looking up at me from between my legs where he had just been kissing his way down my stomach. His fingers had just gotten to my underwear for the first time and that is when he felt it. Usually I am a little more proactive, but this time I guess I just got carried away a bit.

"Yeah," I said. "Seriously."

His name was Adrian. Met him at a rooftop party I went to with my friends. It was honestly kinda off the chains so far as parties go. There was a lot of degenerate behavior going on. We hit it off pretty quickly at the party and he is the one who approached me in the first place. I wasn't sure if he could tell that I was trans or not, but I guess I need to accept at this point that people can not in fact tell.

I mean I know what I look like. Long hair, short dress, slim waist and legs, small boobs. I look like I was born as a girl.

He came up to me and said "I was trying to think of something smooth to say, but I couldn't so I am just going to tell you you're beautiful and hope that works."

"It works," I said. I actually appreciate that kind of approach. It feels honest.

We talked for an hour or two. He was funny. A little nervous, but authentic. Which I liked.

When he kissed me at the end of the night as we were leaving, his hands went to my waist and he pulled me in and I felt everything. He felt fit. I could tell he had more muscle than it looked like. He wasn't bulky, just lean.

"Come back to mine?" he asked.

So I did. That easy. I'm not the hardest girl to get into bed with I won't lie.

This tends to be the part where things always get… Potentially messy. I have been kicked out of people's apartments before. It sucks, but I deal with it. I'm not gonna play victim.

We were on his bed. He took my dress off, slowly and sensually. He was kissing my neck, my cheeks, the tops of my small boobs. His mouth finally found my nipple and they are super sensitive so it made me press into him and I was already getting hard at this point. He was working his way down slowly. Kissing my stomach. Getting ready to take everything off.

I put my hand on his. I needed to tell him. I could feel in my chest that he didn't already know, and it would be wrong of me to not disclose.

"I need to tell you something first." I told him.

He stopped. Looked up at me. "What is it?"

"I'm trans," I said. "I have a cock."

That's when he said it. "What the fuck are you serious!"

He seemed shocked enough that I kind of felt bad for him.

I nodded. I always get this weird feeling in this moment. Shame mixed with nervousness mixed with anticipation. It is hard to explain if you haven't experienced it. I never know which way it is gonna go. Sometimes it blows up.

He sat back stunned. He looked at me. All of me, lying on his bed in just my underwear now. I could see the shape of my cock through the fabric. It is honestly crazy we went this long without him knowing.

"You're so pretty though" he said. He seemed sorta disappointed.

And then he pulled my underwear down.

I was fully hard now. Pressed up against my stomach. He stared at me for a second, and then he wrapped his hand around me and I stopped breathing.

"Is this okay?" he asked.

"Very okay."

I'm happy this one worked out. I think a lot of you guys would be surprised how often guys don't care. Ask them in public and you get a different answer, but in private? Whole new world.

He stroked my cock, slow, looking at my face while he did it. I could feel his hand shaking a little. Nervous. Maybe even confused. I think he was surprised by how much he wanted this.

"Can I suck on you?" he asked. Straight guys always ask. I'm not sure why.

I nodded yes and he lowered his mouth on to my cock and started to bob up and down. It was clearly his first time with a cock. I felt his teeth and then he overcorrected and went too wide. I didn't mind. I love being a guy's first. He just wanted me to feel good and he was doing his best and figuring it out as we went.

I put my hand in his hair. "Use your tongue more. Yeah. Like that." I said to him.

He moaned around me and the vibration felt good.

I was close to cumming embarrassingly fast. I think the situation kinda turned me on extra. I pulled him off and he looked up at me.

"I want you to fuck me now" I told him.

He stood up and took his clothes off and he was hard. Really hard. He put on a condom and I told him where the lube was in my purse and got on my stomach.

He was really slow at first. Almost too careful. I had to push back against him before he got the signal that I could take it.

"God, you're tight," he said as he slid the tip of his cock into my ass.

"And you're going slow" I giggled.

That is when he stopped going slow.

He fucked me face down on his bed. With one hand flat on my back holding me down. I reached around under myself while he fucked me and stroked my cock in time with his thrusting.

When I came, it was all over his sheets. I moaned loudly. He felt me tense up and squeeze his cock tightly with my ass and I think that is what set him over the edge. He started cumming and he thrust all the way into my ass and unloaded while inside of me.

We lay there for a while. Sticky. Breathing hard.

"I've never done that before," he said.

"Done what?"

"Any of it. All of it." He paused. "You're really hot. I just want you to know that." he told me.

I rolled over and kissed him. That was sweet of him to say. I slept over that night.

The next morning, his roommate saw me coming out of the bathroom in his shirt and he just nodded at me, completely unsurprised, and went back to eating cereal. Adrian turned bright red. He may have done something new last night, doesn't mean he is fully comfortable with it yet. I'm not judging. It takes time.

I still have his shirt. He hasn't asked for it back. I honestly don't think he will.

Hey there, me, Jake (28) needs to talk about this.... I met Hayley (26) on a dating site a few weeks back, and we seemed to really hit it off... I asked her out on a date and she wanted to do something casual like drinks and dancing, so we went to pub style restaurant and then dancing.... we had a few and ended up kissing pretty good in the dance floor... around midnight we went outside and we just started making out away from everyone and felt some hard press against me and I just kind of ignored it.

She asked if I wanted to come back to her apartment, so I happily did..... we took a cab back and she said "before you come up, I want you to know I am trans, I still have yenno" and I don't know if it was the drinks, or curiousity, but I just kissed her and went upstairs.

We got up to the apartment and she grabbed me a drink, and we just sat and chatted for a bit, till she sat on my lap and we started making out.

*i WANNA MAKE CLEAR SHE WAS SUPER UNDERSTANDING AND DIDNT EXPECT ANYTHING*

She took off my shirt, she took off hers and I was loving up on her... and then she went down on me, and it probably was the best blow job I have ever had in my life... I stopped her right before finishing and she asked me if I wanted to shower as we were all sweaty from the bar and dancing..

So we got to her bathroom, I get undressed and she slowly did and then her cock came out, and holy fuck... I loved it... it was a good 7-8 inches, good curve, clean, good girth ... and she says all shy "I hope you like it"

We get into the shower and clean off quick with lots of kissing etc.... and we get into bed... I was still really nervous about everything. We just started cuddling to a movie, her cock rubbing on my leg and I was loving it... then she starts kissing me neck which is getting me going..

she gets on me and were kissing and I feel our cocks rubbing together and feeling the precum drip on me and I was getting so horny wondering who it was ... she goes down on me for a bit and then she lays back and I put my hand around her hard cock and she smiles and says "you don't have to do anything you don't want to" and I said "I want to, I am just nervous, teach me" so I stroked her shaft for a bit and said, fuck it, now is the time if I am ever going to do it.

So I started kissing her neck, down her body, her tits... and I get down and I am nervous as all can be... and she reminds me if I dont want to, I dont have to.... but I was so horny, and wanted it so bad... I couldnt stop thinking about her cock... I said "i got this" and I kissed all down there,.. Doing exactly what I would want when someones down there... I started licking and sucking the balls, then licked all up and down the shaft, slapping the head on my tongue and tasting the precum.... she was telling me to touch myself while I did it... which was getting her going more... I went up and played with the head for a while because I was nervous .. and she was loving it, then I said "no or never" and put that cock in my mouth while I was stroking it... and I kept going and kept going... then decided I wanted to try to deep throat, and I did... it was hard but I loved feeling full. I kept going and she said "im going to cum" and tried pulling out and I just drowned myself in her cock... I was so "cock drunk" and loved her busting in my mouth... I swallowed it all and cleaned her all up...

She then bent over and said it was my turn, got ready and fucked her from behind, and I enjoyed every second of it... then I came in her at her request.

We got in the shower to wash off and she asked me what I thought of my first time, and I said I loved it, and she asked me what my favorite part was, and I was honest when I told her, it was sucking her dick. Anyone who knows me, knows eating pussy is my favourite thing, and I was just so full of adrenaline and loving the taste of her cock... so she said "I don't believe you" and I just dropped to my knees and put her cock back in my mouth, feeling it grow hard again in my mouth was so satisfying... then I stood up and she said "Okay i believe you"

We then got into bed, still naked... cuddling and fell asleep, I woke up around 4am to her spooing me and her cock was rubbing on my ass, and I never expected to enjoy it, but I was hard immediately, so I started grinding back on it and felt it get hard and press against my ass... she clearly woke up during it as she started kissing me and grabbing me from behind... and I siad "I want you", she said "what do you mean?" I said "I want you to fuck me" and she was very reassuring.... and said "you've never done this before.. etc"

I was so horny, and I told her to put it in me... and she said "ok, let me know if its too much" ... I bent over, she slowly started putting it, it hurt at first, but then I started relaxing, and it felt so good.. I loved feeling full. She was probably only in about 3/4 of the way, but even with the slight hurt, I felt so good, and I told her to fuck me... and she did, to the point I had my first "hands free cum" then flipped me over into my own mess, and fucked me more.. and as she was about to cum I told her to unload in me and god it felt so good.....

then we went to bed and I felt so good with it leaking out of me... we fell asleep, I went home and we have another date in the next few days.... any advice on how to give better head? I've never done it till tonight.... but I fucking loved it...

He didn't mention it at all until we were already in his apartment. We had been on a date. A real one. Dinner at a Thai place. A fancy one. I can tell a lot about a guy honestly by if he is willing to be seen with me at a public place. A lot of guys are down to hook up, but they get embaressed being out in public with me cause i'm trans, and I guess there is a weird perception that threatens their masculinity or something.

We were sitting on his couch after our date and he was kissing me. Well we were kissing each other. His hand was under my shirt on my waist, and I was thinking about how the normal progression of things goes when suddenly he pulled back and looked at me.

"Can I ask you something?"

"You just did." I joked.

"I want you to fuck me."

I looked at him. He was serious about it. His eyes were steady and his hand was still on my waist and I could tell he was both nervous and excited to have asked me.

"You ever been fucked before?" I asked.

"No you would be my first." he replied.

I appreciated t his honesty. He just said it. I liked that.

"Have you done anything like this before?" I asked.

"With a toy. Never with a real person."

"And you are sure you want me to be the first?"

"I've wanted you to be the first since I read your bio." he confessed.

That was honestly all I needed to hear from him. I love being a guy's first. They always like it so much more than they expect.

I pushed him back against the couch and straddled his lap and kissed him again. Wetter this time than the first. His hands went to my ass and he squeezed and I was grinding against him and felt his cock already hard through his pants and I was getting fully hard too now.

"Take your clothes off," I said. "All of them." I ordered. I have found that guys often like when I am bossy. That is part of the fantasy for them. They secretly want to submit.

He stripped fast. He had a good body. Lean and fit, darker skin, a trail of hair down his stomach that I touched with my finger while he just watched me. I took my time getting undressed for him because I liked the way he was looking at me. When I finally pulled my underwear off and he saw my cock for the first time I could see it had quite an effect on him.

"Can I touch you?" he asked.

"You better." I giggled.

He wrapped his hand around my cock and stroked me so I closed my eyes and let him do his thing. He was curious. I could tell. Precum started leaking from me and he touched it with his finger before putting it into his mouth.

I pushed his hand away and kissed my way down his body. His cock was hard as fuck and I took it into my mouth and sucked on him until his hips were lifting off the couch and thrusting forward. Then I went lower. He spread his legs for me and I used my tongue on his asshole to get him wet and he grabbed my and said "Fuck" like it surprised him. I don't think he expected it.

I got him ready. Slow. Careful. Gentle. I know how to be a guy's first. I used the lube I always carry with me and my fingers at first, one and then two. He was breathing hard and his cock was leaking onto his stomach. A lot.

"Ready?" I asked.

"If you don't fuck me right now I'm going to lose my mind." he basically begged me.

I positioned myself against his tight virgin ass and pressed against him and pushed in slow. His hand grabbed my wrist and I stopped.

"Keep going," he said through his teeth. "Just. Slow."

I went slow. Inch by inch until finally I was all the way inside his ass and his eyes opened and he looked at me with this happy expression on his face. The face someone makes when they finally do something they've been fantasizing about for a long time. I know that face.

"You okay?" I asked.

"I'm so much better than okay. It feels so good" he replied.

I started to fuck him. Gentle short strokes that gradually got longer and longer as he started to relax around me. His hand reached down to his own cock and he started stroking himself while I fucked his ass and the sight of him touching himself while my cock was deep inside him was one of the hottest things I've seen. I love that sight.

"Harder," he said. "Please fuck me harder" he begged.

I put my hands on the armrest behind his head and started fucking into him deeper and deeper and he just moaned loud and his hand grabbed the back of my neck and pulled my face down and he kissed me deeply while I fucked him.

"Say something," he breathed.

"You feel incredible. I love fucking your ass" I told him.

"More."

"Your ass is so tight around my cock and you take it so well i'm gonna fill you tight ass with my cum" I whispered in his ear.

He came. His cock was between us and he shot it up on to his stomach and even his chest and his whole body squeezed around me and I felt him grip my cock so I just thrust harder through his orgasm.

"Don't stop," he begged. "Please don't stop. I want to feel you cum in me."

I couldn't hold back after that. I pushed deep and came inside him and he held me tight against him and kissed me and I felt myself empty into his hole as he whispered "yes" over and over and we stayed like that, connected, both of us breathing hard.

I pulled out after a while and he lay there looking wrecked. Cum on his stomach. My cum inside him dripping out of his asshole. We were all sweaty. He had a blissful smile on his face.

"As good as you expected?" I asked.

"Even better" he replied.

I got him a towel. We cleaned up and took a shower together where we washed each other with soapy water until we were finally clean again.

He ordered ice cream on his phone without looking away from me. I sat on his couch wearing his shirt eating ice cream and thinking about how his face looked while I was fucking him and honestly it was a really good night. I ended up sleeping over.

I can't decide if I wanna see him again or not, but he has been hitting me up nonstop since it happened. What do you guys think? Should I add him to the roster?

Okay so you guys have been asking me a lot about my experience with "submissive" guys so to say. I have honestly been surprised by how many "straight" seeming men have an interest in getting fucked by a girl like me. It is way more common than you would imagine.

I met the guy in this story at a house party a little while ago. I almost didn't actually go to the party, but my friend kept texting me. "Please come." "It'll be fun." "There's a guy I want you to meet." and I must admit that kind of captured my curiosity.

The guy she wanted me to meet was not the guy this story is about. The guy she wanted me to meet was some finance bro named Tyler who talked about his apartment renovation for twelve straight minutes and I was honestly bored out of my mind from him.

A guy named Soren is who this post is about. He was leaning against the kitchen counter with a drink, watching me talk to boring Tyler, and when Tyler finally went to get a drink, Soren leaned over and said, "That was painful to witness". I guess it was obvious I wasn't interested.

"It was worse to experience." I told him.

He laughed. He had a good laugh. It was deep and authentic feeling. He was maybe mid twenties, had broad shoulders, a mess of curly hair that looked like he just got out of bed. He was wearing a flannel that was unbuttoned a few buttons too far, and I noticed it and he noticed me noticing it. Then the flirting started.

We talked. He asked me what I did for work, and I just said "oh nothing interesting", which is usually what I tell people who I just met instead of being honest and saying right away that I do porn lol. He said good, he was "sick of interesting people". He asked me what I was drinking and I said "everything and anything" and he handed me his drink and got himself another one.

He kept finding ways to be close to me. Not aggressive or creepy or anything. Just being present. Standing next to me while we talked to other people and stuff like that. His hand ended up on the small of my back when he reached past me for something, and he kept finding little excuses to touch me. I think he still thought I was a fully natural girl at this point, and I figures I should probably let him know that I was trans before we took things too much further.

Around midnight the party got a little more quiet and he said, "There's a balcony upstairs. Quieter. Coming?"

It was actually a bedroom. There was a balcony attached to it, small, barely enough room for two people. We stood out there and the air was fresh and I leaned on the railing and he stood close enough that our arms were touching each other.

"Can I be honest with you?" I said.

"Always." he replied

"I'm actually trans. I just thought you should know" I confessed to him.

"Don't worry. I had my suspicions. I actually was kind of hoping you are" he replied.

I turned to face him. He was looking at me with this open, vulnerable expression. No game. No smooth mooves. No calculation. It was weirdly intimate.

I kissed him. He kissed me back immediately, one hand on my cheek, the other on my hip pulling me against him. His mouth was warm and our tongues pressed against each other and things moved quickly from there.

We went back into the bedroom. He pushed the door shut. I pushed him onto the bed and climbed on top of him and his hands went everywhere on my body, my waist, my thighs, up under my shirt to my chest. He cupped my breasts, barely a handful, and rubbed his thumbs over my nipples and I felt myself starting to get hard.

"God, you're gorgeous," he said.

I pulled my shirt off. He sat up and kissed my neck, then the flat spot between my small little boobs. His hands slid down my sides and he started pulling off my skirt. He pulled it down and I helped, kicking it off, and then I was in his lap in just my underwear and his hands were on my ass and I could feel his cock hard underneath me.

His fingers slipped under the edge of my panties. Then moved to the front.

He found me soon after.

His hand paused. Not a flinch. Not a jerk away. Just a slight pause. I could tell it was his first time doing this.

He looked at me. I looked at him.

Then he asked "Can I touch you?"

"You're already touching me." I giggled.

He smiled. He wrapped his hand around me and I was already hard and the feeling of his fingers tightening made my cock drip with precum.

He stroked me slow at first, then faster. I rocked against him and his other hand gripped my ass cheek and he was watching me, looking right into my eyes.

"I want you to fuck me," he said.

I stopped. "What?"

"I want you inside me." His voice was steady. No hesitation. I was really surprised honestly because usually guys want to fuck ME. Not that I minded. I always bring lube with me to these types of things so its not like I wasn't ready.

"You're serious." I confimed.

"Completely."

I took the lube from my purse and pushed him back on the bed and he went willingly, almost gratefully, pulling off his jeans. I think a lot of masculine supposedly straight guys secretly fantasize about what it would be like to fully submit. To give in and let someone else lead them.

I was gentle. At first. I started with just my fingers and he kept making these sounds, low and encouraging. When I finally pushed my cock inside him he grabbed the sheets and arched his back and said my name softly.

"Arya. Fuck."

I set a steady pace. Not slow but not rushed. Deep. Deliberate. Smooth. He wrapped his legs around me, and I held his hips in place while every thrust into his ass caused him to moan again and again. I reached between us and started to stroke him, and I watched his face build up with pleasure and felt powerful in a way I don't usually get to feel.

Eventually at one point i had him pushed up against the headboard of the bed and I could just tell he was close. It was the way his breathing went gasping, the way he whispered "harder. Fuck me harder".

He came first and I felt it all over my hand. I reached up and licked a little bit of his cum off my fingers and moments later I came inside his ass and collapsed onto his chest and we lay there breathing heavily. The party was still going on downstairs but we were in our own world

"That was… Insane" he said to me.

"Yeah? You liked it?"

"I've never done that before."

I propped myself up on one elbow. "Really?" as though I didn't already know.

"Never wanted to. Until this very moment."

We ended up showering together in the bathroom before finally going back down to the party to socialize again. I ended up getting his info and we promised to keep in touch. I haven't seen him again since, but I plan to soon.

So there you guys go. The story many of you have been asking for. I hope it lived up to your expectations, and I promise i'll keep you posted on any new developments!

its been days now and that night will not leave my head. every time i walk or sit the cage shifts and reminds me all over again. i still cant get over the fact that my first kiss was with her sweaty foot. that keeps looping in my head more than anything else. i kept replaying her foot on my face and that thick cock stretching me out until i finally snapped and started searching online
took forever but i found her instagram. messaged her right away. “hey its me from the other night… the short guy. i cant stop thinking about what happened. can i see you again?”
she left me on read for hours. eventually just replied “what do you want”
i typed so fast my fingers were shaking. told her i needed to come over. begged a little. said the cage was driving me crazy and i had to see her. she made me wait even longer then finally said “fine. come over. dont be weird about it”
showed up in shorts and a singlet. she opened the door wearing this simple casual dress and still looked unreal. the second i saw her my stomach dropped. all i could think about was how her sweaty foot was the first thing my lips ever touched and how she completely dominated me that night. how she took control so easily and left me locked and used. the shame of how far she pushed me sits in my chest like a stone. i still get hard in the cage thinking about it and that makes me hate myself even more
we sat on the couch. i tried filling the silence because she barely said anything. asked how her week was. asked if she went out again. told her i hadnt been able to focus at all because of the cage. kept talking about how weird it felt walking around locked up and how i kept checking if anyone could notice the outline. she just nodded or gave one word answers. after a few minutes of me rambling she smirked and cut me off
“so how’s your butt feeling”
i looked away. the question alone made my face burn. “still sore”
i swallowed and asked about the key. she tilted her head and said she lost it. that little smirk on her face made it obvious she was lying and that she didnt care enough to even pretend properly.
said i needed the bathroom then snuck into her bedroom instead. started pulling open drawers. found a whole collection of toys. different sized butt plugs, dildos, cuffs, more cages, weird stuff. my hands were shaking. every toy made the shame worse because i knew what they were for and that she probably used them on guys like me without thinking twice. still couldnt find the key
i was about to leave when she walked in
“what the fuck are you doing in here”
i tried saying i got lost looking for the bathroom. she didnt buy it for a second. grabbed me by the throat so hard i choked. shes so much stronger than me it wasnt even a contest. threw me onto the bed and pinned me down while i tried to squirm. snapped the handcuffs around my wrists in front of me. i kept struggling for a bit then just stopped. no chance of getting free. the whole time her face stayed bored, like catching me was nothing special
she opened a different drawer and held up the key between two fingers. “looking for this?”
dragged me into the bathroom by the cuffs. stood me in front of the toilet. held the key over the bowl and looked me right in the eyes. “say goodbye”
dropped it. the little metal key hit the water with a tiny splash. she flushed. i watched it spin around and disappear down the drain. something in my chest just sank. like the last tiny bit of hope i had left got flushed with it. my stomach felt hollow. i just stood there staring at the empty toilet knowing that cage was permanent now and that she had done it without a second thought. she didnt even watch my reaction. just turned and walked back to the bedroom like it was nothing
she pulled me after her. “youre getting punished for snooping”
ripped my clothes off. singlet shorts underwear gone. left me there naked except for the pink cage. My fat ass on full display. the shame of standing there like that in front of her made my face hot and kinda turned me on. I was nervous what she was going to do but also excited. she pushed me down onto the bed then climbed on top of me. yanked her cock out from under the dress and slapped it across my face a few times. spit straight into my mouth, then forced it past my lips
face fucked me rough for a few minutes. then shoved me so my head hung off the side of the bed and started using my throat properly. could barely get any air. kept trying to push at her hips but she held me there like i was nothing until she felt like stopping
then she easily moved me around and picked me up (im only about 50kg) and folded me into a full nelson. legs behind my head, arms locked, body completely folded up. she lowered me onto her cock and started fucking me hard. every thrust made me feel how small i was. a girl stronger than me, holding me cuffed and caged, forcing her cock that was many times bigger than my locked little dick deep into me in a position i couldnt even move from. the humiliation burned worse than the stretch. i could feel every inch of her sliding in while i just hung there helpless, my own tiny locked cock useless and trapped. she kept going, adjusting her grip when she needed to, using my light body like it was nothing. my face was red from the shame of it, knowing she could hold me like this for as long as she wanted and there was nothing i could do about it
after a couple minutes her arms got tired so she dropped me into doggy and kept going longer. deep heavy thrusts. after that she flipped me onto my back stacked my legs high and fucked down into me. the pressure built so fast i came hard inside the cage. cum leaked out through the hole and onto my stomach while i just throbbed uselessly against the plastic
she pulled out and told me to stroke her. i used both hands. she held her phone up and recorded the whole time. she came all over my face. thick ropes everywhere. she scooped some up with her finger and pushed it into my mouth, making me swallow, then made me clean the rest off her with my tongue
this time she let me put my clothes back on. then she looked at me like i was nothing special and said “get used to living without a cock. youre never getting that key back”
and “get used to this. ill be seeing you again soon”
walked home in a daze. when i finally got inside i didnt even look at the cage. just accepted it. that little pink lock is staying on forever and im not gonna try to get it off.

P.s. I asked her for the facial / cum swallow video and she told me to fuck off so I don’t think she wants to send it to me

ok so this happened last friday and im still thinking about it every few minutes
im 5’4 skinny as hell always been the short quiet guy. no muscle just this plump ass people used to slap and laugh at my whole life. and between my legs i got a micropenis. barely an inch soft maybe a bit more hard. never kissed anyone never even held a girls hand proper. just years of feeling like a joke
finally forced myself to go to this club downtown. put on tight jeans that made my ass stick out more and tried. talked to like five or six girls and every one either ignored me or looked at me like i was gross. one group literally laughed when i walked up
then i saw her at the bar. tall like 5’11 long dark hair tight black dress really pretty but in that scary confident way. i walked over because i had nothing left to lose
tried talking and she just stared down at me with this half disgusted smile. after a minute she cut me off
“have you ever even been with a woman? does this whole nervous short guy thing ever work for you?”
my face went hot. looked at the floor and mumbled that ive never even had my first kiss. she kinda laughed under her breath
“yeah being shorter and skinnier with a bigger ass than most of the girls in here probably doesnt help your chances”
i just stood there feeling like shit. then she leaned in a little and said “look im ready to leave this place. you wanna come back to mine?”
i said yes so fast it was embarrassing
her apartment was only a few blocks away. door closes and she doesnt waste any time. no soft talk or anything. just looks at me and says “ok. take your clothes off”
i froze for a second then did it. shirt jeans underwear everything on the floor. stood there naked skinny body plump ass and my tiny soft dick just hanging there. she stared for a second then straight up started laughing. not a cute laugh either
“oh my god. that is not going to be needed tonight”
she walks to a drawer pulls out this small pink chastity cage and comes back. my heart was hammering but i let her put it on. she clicked it locked and said “much better. there only needs to be one dick tonight”
i didnt fully get what that meant yet
she pointed at the floor. “on your knees. take my shoes off”
i dropped down. she lifts one foot right up to my face and the smell of sweat and leather hits me. “kiss it”
so i did. pressed my lips to the bottom of her smelly foot. that was my first kiss. not some soft romantic thing just the sole of a tall girls sweaty shoe. my caged dick leaked a little the second my lips touched her skin. i started kissing more making out with her foot tongue and everything. she watched me for a bit looking shocked but turned on
after a while she pulls her foot away. “alright. youre going to give me head now”
i got excited. first real sexual thing ever. tugged her pants and underwear down fast and this thick hairy nine inch cock flops out right in my face
i jerked back. “i… i didnt know you were trans”
she just smirked. “surprise”
my cage was leaking even more. i hated that it turned me on but it did. a lot. put the tip in my mouth and started sucking. salty and heavy and way too big. she put a hand on my head and pushed a little. i only managed about half before gagging but kept going drooling all over it
after a bit she pulls out. “turn around. im going to fuck you”
i got on all fours on her bed. felt her spit on my hole then the fat head of her cock pressing against my virgin ass. she pushed in slow at first then just forced it. the stretch burned and felt full and wrong and somehow really good all at once. she started thrusting hard her heavy balls slapping against my locked little ones over and over
i came in the cage within a couple minutes. just leaked and pulsed with nowhere to go. best orgasm of my life even though it was trapped and pathetic
she kept fucking me through it then pulled out and laid on her back. “ride me. like a good little slut”
i climbed on and sank down on that thick cock again. bounced on it hands on her stomach completely letting go making these dumb little sounds. she just watched me with that same half disgusted half amused face
eventually she tells me to get off and finish her. i stroked her cock with both hands while she held my head. she came hard thick ropes shooting into my mouth and across my face. made me swallow what i could and lick the rest off her shaft
then she sits up stretches and says “thanks for the night”
basically kicks me out right after. kept all my clothes. just opened the door and pointed. so i had to walk home naked still caged with cum drying on my face and my ass sore and leaking a little. lucky she only lived a few blocks and the streets were empty
got home and just sat on the edge of the bed staring at the pink cage. first kiss was a trans girls smelly foot. lost my virginity to her big hairy cock. and she still has the key
part of me hopes she never messages me so i can pretend it was a one time thing. bigger part already wants to feel that full and used again

Yes, it sounds bad. But hear me out…

They’ve been divorced for 4 years. I’ve had the hots for him for like 10+ years and never did anything past flirting. I was out with some girlfriends in downtown Atlanta and we ran into each other, he was out with some of his friends. He texted me at like midnight telling me I looked good and he wanted to get a drink with me. I had told him to come to this bar with live music. He came alone.

We had about 4 drinks and started making out on the dance floor. I whispered in his hear “you’re getting ass tonight.” “He said really? Do I get this too?” And he grabbed my cock. I said, let’s go, now. Got an uber back to his place and after a decade of sexual tension, it finally went down.

He stripped me naked and ate my ass. I then got him naked and gave him head. He then fucked me from behind while he was standing up as I was hunched over his couch. I let him go inside me.

We made out for about half an hour and then went again missionary.

We went to bed. Showered together in the morning and went doggy style in his bed afterwards. We got Chick-fil-A for breakfast and then I gave him road head back to his place.

He’s coming over to my place tomorrow night and I can’t wait!!

I've been hooking up with this guy Felix on and off for a couple months now. Casual, nothing serious. Mostly just fun. He knows I'm trans obviously, and he's so into it. What we have is honestly great. It's easy. Good sex, low drama, and minimal time investment required. The only unusual thing about it is that Felix has a girlfriend, and he hasn't told her about me.

To be honest that actually isn't all that unusual. It is shockingly common for many straight guys with girlfriends or wives try to hook up with me. I deal with it all the time, and I must admit a part of me loves being their secret fantasy. I play into a lot too. Anyways.

Last week he texted me something different.

"My girlfriend wants to meet you."

I didn't know until now that his girlfriend knew about me. Which, fine, maybe I should've asked more questions. I assumed I was more of a secret thing. But he explained. I guess recently he and his gf Tessa have been talking about adding other people into their relationship, and sort of opening things up. Apparently they have been talking about me during sex, which honestly was hot to think about.

He ended up telling me that Tessa was "curious" he said.

"Curious about what?" I asked.

"About you. About your situation."

My "situation." Sure. I knew what that meant.

"She wants me to fuck her?"

"Yes. And so do I. I actually want to see you cum in her" he replied.

I stared at my phone for a solid minute before I responded.

"Like. Inside her?"

"Yeah. We have been talking about it. The idea of a girl like you cumming in her is the hottest thing ever honestly".

I'm not going to pretend I hadn't thought about it before. I have a cock. I cum. I know what that means. The idea of being inside a girl, bare, and finishing deep, I think about it a lot. I've done it a few times too but it has been a while since i've been with another girl.

"When?" I texted back.

Tonight. Their apartment. Tessa opened the door and she was stunning. Shorter than me, dark curly hair, this soft curvy yet petite body in a sundress. She smiled at me with a naughty little smile that I really enjoyed.

"Hi. You're even prettier than the pictures."

"You too."

Felix was on the couch. He waved. Casual. Like I was coming over for dinner, which technically I was. We ate Thai food and drank wine and Tessa kept finding reasons to touch me. By the second glass, her hand was on my thigh.

"Can I ask you something personal?" she said.

"You're about to let me fuck you. I think personal is fine."

She laughed. "How big are you?"

"Come find out."

That's how we ended up in their bedroom.

Felix sat in the chair by the window. He wanted to watch. Tessa and I stood next to the bed and she kissed me, soft at first, then harder. She tasted like the wine. Her hands went to my shirt and she pulled it off and looked at my small tits, my flat stomach, and then down.

"Can I?" she asked, fingers on my zipper.

"Yeah."

She undid my jeans and pulled them down and I was already hard, straining against my underwear. She cupped me through the fabric and her eyes went wide.

"Oh my god," she whispered.

She pulled my underwear down and my cock sprang free and she just stared.

"You're a girl with a dick," she said. Not mean. Amazed. Like it was the most exciting thing she'd ever seen.

"That's me."

She stroked me, slow. I was already leaking. "And do you think you could get me pregnant?"

"If you let me cum inside you, yeah."

"I want you to."

I pushed her back onto the bed. She pulled her sundress off and she wasn't wearing anything underneath, and she was already wet. I could see it. I could smell it. She spread her legs and I got between them and the head of my cock pressed against her and she gasped.

"Go slow," she said.

I pushed inside her. No condom. Bare. And the feeling of her around me, tight and wet and warm, I almost came right then. I had to stop and breathe.

"You okay?" Felix asked from the chair.

"She feels incredible," I said.

Tessa pulled me down and kissed me while I started to move. Slow at first. Feeling every inch of her. She was making these soft sounds against my mouth and her legs wrapped around my waist.

"Harder," she said.

I gave her harder. My hips snapping forward, pushing deep, and she was moaning now, loud, gripping my shoulders. I could feel her getting wetter around me with every thrust.

"I want you to cum in me," she said. "I want you to fill me up."

I looked at Felix. He was watching, hard, his hand on himself through his pants.

"Do it," he said. "She wants it. Fuck my girlfriend full of your girl cum"

I started fucking her faster. The headboard was hitting the wall and I could feel that pressure building at the base of my cock, that tight hot tensing feeling. Tessa was moaning and had her legs wrapped around me.

"I'm close," I said.

"Inside me. Please. Don't pull out." she begged me.

I pushed in as deep as I could go and came. Hard. I felt myself pulsing inside her, filling her, and she made this broken sound and tightened around me so hard I couldn't move. I just stayed there, buried, emptying into her while she shook and her boyfriend watched.

I stayed inside her for a long time after. Neither of us moved. Just cuddling. I could feel myself softening inside her, my cum warm between us.

"Thank you," she whispered. That was so hot.

Felix came over and kissed us both. Tessa was lying there with this happy look on her face, her legs still open, and I could see the mess I'd made starting to leak out of her.

That is when Felix surprised me. He had Tessa lay on her back and he made her spread her legs. He started rubbing his gfs clit using my cum as lube. Tessa started moaning softly again at his touch. A moment later Felix had his tongue on his girlfriend's pussy, and he was licking and tongue fucking my cum out of her. I hadn't expected something so dirty from him honestly.

Tessa was moaning and I started to get hard again just from watching. I started stroking myself and I just watched as Felix tongue fucked his girlfriend's cum filled pussy to orgasm. It didn't take long, just a few minutes.

"Oh my god. That was so hot!" Tessa said when Felix was finally done. She looked thrilled about her bf doing what he did.

Then I got dressed and got ready to leave. I sorta got the feeling that the two of them wanted some couple time. They thanked me as I left and each of them gave me a deep kiss as I walked out. I must admit I felt the love from them. It felt like they really appreciated and enjoyed me. I hope we take things ever further.

Tessa texted me the next morning. "When can we do that again?". Not gonna lie I was pretty happy to hear that she still felt happy about it. I have had people regret hooking up with me before, but the fact that the next day she still felt good about it was a great sign to me.

I'm going back this weekend. Can't wait!

Ive been meeting with trans escorts since I was 18, the first time I met up with one, she was very polite and I was clearly unsure about what I wanted. At that point in my life, I had only been sexually active with cis women, but I was curious after discovering trans porn. So meeting up the first time, I was nervous, but luckily she took charge and took me through a little of everything. She let me suck her cock and get comfortable around her, and then gave me a massage. About 25 minutes of a massage, she climbed on my back and slid her cock into me. That was thr first time ive ever had anyone other than me insert something there. She took her time and let me get used to the feeling, then she started going faster and harder. All in all, it was an amazing experience for my first time. I visited her several times throughout the years and became a sort of regular of hers. Once or twice she filmed our sessions for her onlyfans, and that was a big excitement for me.

I travel a lot for work, so I am always in a new city, and o occasionally look through the classifieds for another trans escort. Ive hooked up with several, but it was never as good as it was with my first.

Last week, after not bottoming or seeing an escort for 3 years, I decided to browse the classifieds, and I found a girl that checked all the boxes.

It was a quick session and right to the point, but she was fun and easy to talk to.

All in all, it was a great experience, but it didnt come close to my first time

I want to share with you guys how I prepare for a solo anal night.

I really take my time preparing for the evening/night with myself. I usually begin by taking a shower and shaving my legs, dick, and butt. It’s such a good feeling when everything is shaved and fresh, especially when I use massage oil. After cleaning the outside, I use a shower douche to thoroughly clean back there.

After my hygiene session, I rub organic coconut butter all over my body and insert my medium pink SquarePeg egg buttplug. With the plug inside, I slowly get more excited and horny. To build on that feeling, I don’t put on any clothes and walk around naked in my apartment. I love taking a look in the mirror from every possible angle and enjoying the view. The way the pink egg plug looks on me turns me on so much.

After stretching my butt with my buttplug for a while, I set up all of my toys on my nightstand and decide which one I’ll try first. I then lay a towel over my bed, along with paper towels and wet wipes.

Sometimes I like finding a couple of porn videos
of other sissies using a dildo in the same position. I will then cast it on my tv I have mounted on my wall directly in front of my bed and slowly stroking my butt along with the rhythm. I have this dildo that I love to use. It’s not too big, but it has a bulky base that feels so good in my hand.

Other times, I like to just turn off the lights and TV and get under the blanket. I love fucking my butt in complete darkness for hours.

Most of the time, while pleasing my butt, my dick isn’t hard but is still very sensitive. While fucking my butt, I reach down with my other hand and tickle my balls, slap them softly, or grab them and pull a little.

When I get tired I’ll I take a little break, put in a bigger SquarePeg egg buttplug, lie down, close my eyes, listen to my favorite sensual music, and just feel my body and fantasize about the things I could do to please myself even more.

I will also walk over to the kitchen to grab a glass of water. The penetrating feeling of my plug and the thought of my butthole being filled up is just awesome.

After a while, when my energy has recovered a little, I love to put in my other, slightly bigger dildo.

As you can probably tell from my post, I’m doing very long sessions, sometimes even more than 12 hours. I mostly listen to sensual music or watch my favorite porn videos usually of other sissies using their dildos or a fuck machine.

I really enjoy showing myself in front of my camera. I don’t share anything yet, but I love looking at my pictures and videos afterward ;)

What does your solo anal night look like?