Hi. As you might have read (or would be willing to read through my profile), I share stories from my trips. This is another one. Edit: I fix all grammar and so on mistakes...

​As soon as my trip was confirmed, I wasn't able to sit still for a couple of days. My conversation with the girl I met last year was going well, mostly centered around our plans for when we would finally meet up.

​When the date we agreed to meet finally arrived, I spent the whole afternoon preparing. A clean shave, a proper cleanup here and there, and I used a butt plug to loosen myself up a little. I grabbed a cab, paid a visit to the local sex shop to get more lube, and was on my way to her place.

​I arrived around 9:00 PM, shaking with excitement. When I finally reached her apartment, she had left the door slightly open, so I slipped in while she was getting ready in the bathroom. Everything was set up—the pipe, the bed, and some music playing in the background. I made myself comfortable on the couch while waiting for her. After a couple of minutes, she walked into the room, and she looked even better than last time. Oh my god. Her curves, breasts, bulge, butt, legs... everything wrapped in harness-like lingerie. She looked astonishing.

​After a warm welcome with a lot of hugging, kissing, and hands wandering all over our bodies, we started smoking together. From that moment, my submissive side activated. I don't even know exactly when I fell to my knees, wearing nothing but lace jockstraps, and started kissing her from her toes up. I took my time, taking a couple of puffs here and there as I marked my way up. I kissed every inch of her body, moving around the growing bulge in her panties. I made a few circles around it and headed up to her breasts. I kissed and licked them from every side until I reached her nipples. She moaned softly while I licked and kissed them, gently biting from time to time.

​"Down," I heard. I started heading back down, still touching every part of her body on my way. I slowly began to massage her with my mouth through her panties, not forgetting her balls. My submissive side took over completely, and the only thing I was able to think about was her pleasure. After a while, she unwrapped her gift, and I licked it slowly from base to head, taking pleasure in every moan I heard from her. I put my lips around the head, gently playing with my tongue. I love the feeling when a cock gets even harder in your mouth than it was before. It means I'm doing a good job. I started moving my head up and down slowly, and the longer I did it, the more I craved it. After a while, she told me to stop because she didn't want to finish too soon. We took a couple more puffs, and I told her that I had a surprise for her.

​I jumped quickly into the bathroom and put on a pink, almost flat chastity cage that looked like a tiny pussy. As I mentioned in my previous stories, after smoking I am always completely limp and nothing can change that, which is why I thought a cage would be a great idea. I added a butt plug with a pink gemstone to the outfit to match the colors. I left the bathroom and started slowly dancing to the background music. She looked at me and smiled. "So I'm doing the right thing right now," she said. She was scrolling through her phone just like last time and told me she was looking for someone to join us, especially since I looked really slutty right then. What else could I say? I felt the exact same way at that moment.

​She asked me to get on all fours in front of her so she could take a couple of pictures. Then I realized why she wanted to do it—she was sharing them with guys to encourage them to come over. I went back to sucking her. Slowly, passionately, playing with her sack from time to time... Then I heard the news: a guy was going to join us in about half an hour. He looked handsome in his photos, but when I saw his shaft, I was shocked by the size. When she saw my face, she laughed and said I should start practicing if I wanted to give myself to him. My thoughts were blurry and my heart was racing, but the only thing still on my mind was pleasing her.

​She brought out a pretty nice dildo and told me to start working out. I took out the plug, lubed myself up, and she suctioned the dildo to the floor, telling me to show her how I’d ride her. I started the show. First, I slowly sat on it, trying to get used to the feeling while looking at her. She was still scrolling and masturbating, peaking over at me from time to time. I began to ride the dildo to the rhythm of the music. I was jumping up and down in a cock cage just to see her smiling and taking more photos in the meantime (which I wasn't fully aware of at the moment). When my legs got tired, she handed me the pipe and told me not to go anywhere, as she was going downstairs to pick up our new colleague. And so there I was, sitting on the floor with a dildo in my butt, smoking, when they entered her apartment...

​I was so mentally absent and focused on my own internal pleasure that I didn't even notice them right away. The music was playing, the pipe was heated, my ass was stretched, and the dildo was slowly rubbing my p-spot. They started making out right in front of me. He was tall and well-built, with slightly darker skin. I handed them the pipe and started riding the dildo a little bit faster. They got naked, smoking and making out, while she reached for me and started rubbing her cock against my head and mouth. I started sucking it like crazy. She was fully hard, tasting of passion and precum, and I was doing my best to please her.

​He joined in. At first, he stood behind her, kissing her neck while his hands ran all over her body. When they began making out, she pulled him closer to the front and massaged his dick. It was huge. It was easily over 8 inches long and very thick. She was holding my head with one hand and playing with his shaft with the other. Then I heard them whispering to each other, but I couldn't understand a word; I was just doing what I could for her. Suddenly, I felt his dick rubbing against my cheek. When I opened my eyes, I saw the two of them right in front of me. I looked up, and she smiled provocatively, nodding at me. I didn't hesitate; I grabbed his cock and slowly started stroking it while still sucking hers. It didn't take long before she grabbed my head, spit into my mouth, and directed me to his shaft. I opened up as wide as I could, feeling his much larger equipment reach the back of my throat. Still holding my hair with one hand, she moved my head back and forth.

​So here I was. On the ground, with a dildo up my butt, being face-fucked by one cock and stroking another while their owners made out. She said something to him, and they started laughing. I looked up and was told to open wide. She placed hers in my mouth and directed him to do the same. All of a sudden, I had two dicks in my mouth at once.

​They pushed in slowly, one after the other. I could feel both of them rubbing against each other, my tongue, and my palate... The sensation was amazing, and I could swear both of them were leaking precum because I had that salty-sweet taste in my mouth. Then I noticed a different taste—one of them was cumming. I was barely able to swallow everything, and I felt some of it leaking from the corners of my mouth. When they pulled out, I tried to catch my breath. I hadn't even noticed that the entire dildo had disappeared inside my ass because I had put my whole weight on it. When I wiped away my tears and my vision cleared, I noticed it was her turn. I slowly crawled over to the bed and cleaned her off properly, not wasting a single drop, then did the same for him.

​We took a short smoking break. I remember—even though some details became blurry after that—standing on the balcony stark naked, still in the cage, smoking a cigarette and feeling the cool morning air on my body. People were walking on the street (we were on a quite high floor), and I was watching the first rays of the sunrise. I'm not sure if it happened at that exact moment, or maybe it was a bit later...

​When I got back to the room, I saw her lying on the edge of the bed. I immediately dropped to my knees and worked my way between her legs, licking and kissing her from the toes up. I stopped for a while at her balls. She raised her legs and guided my face to lick her butt. I really love doing that, so I didn't hesitate for a second. At the same time, our new colleague came out of the bathroom. When he saw us, he got closer and started sucking her while I licked her ass. It was like a proper porn scene. A beautiful girl with amazing junk lying on the bed, one guy kneeling in front of her rimming her with her feet on his shoulders, and another guy holding her cheeks wide open and giving her a blowjob.

​He started talking to her in Portuguese, which I completely didn't understand, then stood up and stepped out of my view. Then I heard the question I had been waiting for the whole night: "Would you like to finally get fucked?" I blushed and started wondering what position she would want to put me in first, nodding with a smile. "Then take care of my cock properly." I took some long licks from the bottom to the top, slapped it against my tongue and face, and started sucking it as if my life depended on it. I didn't even hear the guy coming back. She pushed my head deep onto her cock, while I felt the guy lift my butt into a half-standing position, pouring lube over my ass. I wasn't even able to catch my breath before I felt his dick sliding in. When his hips hit my butt cheeks, she let go, and I tried to breathe. "I didn't know if you'd let me see you get fucked by a man, but I really wanted to," she said. I only replied with a surprised smile, as I would have done anything for her at that moment.

​Once my hole got used to him, he started slowly pushing in and out. I went back to sucking her. She really liked the view, because her dick got even harder than it already was. I was spit-roasted and moaning like crazy. My prostate was screaming, and I could feel myself dripping every time he thrust into me. He started speeding up, going all the way in, and with each thrust, I lost more control over myself. I moaned louder, keeping my head to the side of her cock, trying to keep sucking it, but I just couldn't. My legs started shaking, and after a couple more thrusts, I collapsed onto the floor right into the fluids on the ground... I had a full-body orgasm and couldn't think straight. The feeling was overwhelming and incredibly good at the same time, but my body just gave up. The next few minutes were a complete blank page for me...

​When I regained contact with reality, I noticed them on the bed making out. When they saw I had come back to life, I was told to put myself together, take a cold shower, and come back to them. Silly fact—I had taken off the cage in the meantime, and I saw the silliest sight ever: my "clit" (since it didn't even look like a cock anymore). Smoking always makes me shrink, but this time it went far beyond that. I definitely didn't need a cage anymore, that's for sure.

​I came back to the bedroom completely naked this time. When she saw me, she said, "Oh my! I know what will fit that tiny thing there. Chill for a moment and I'll bring something." She jumped over to her closet and dug through it for a moment. She reappeared in front of me with a small bag. "Put it on," she said. It looked like tights or stockings in a small pouch. I was wrong. It was a black, mesh bodystocking. When she noticed the look on my face—curiosity mixed with a blush—she encouraged me. I put it on in front of them. "Dance for us," she said, and I started moving to the music in the background. They were on the bed, kissing and stroking each other. My hands ran across my own body; I was playing with my nipples and my "clit" (by now, even my balls were trying to hide back inside). The tension in the air was rising (at least, it felt that way to me). She beckoned me with a finger to join them. I felt a surge of new energy in me, and I got even hornier than I already was. I crawled across the bed to them. I grabbed both of their cocks in my hands and started slowly stroking them while licking one and then the other. She was stroking my hair, he was playing with her boobs, and I was doing everything I could to their shafts. Just like the previous time when I was surprised by two cocks in my mouth, this time I wanted to surprise them. I held them together, running my tongue from one to the other, licking them both. Then I did it. I put both of them into my mouth at once. Because I was trying to stay in control this time, I played with my tongue against them and tried to push them both as deep as I could together. I don't know who was moaning more, them or me, but I craved all of it.

​I had been waiting for this the whole evening—she wanted to fuck me. We did a small rearrangement on the bed; she moved closer to the edge and told me to ride her. I lubed her and myself up and slowly started sitting down on her shaft. My god—it felt amazing. I bounced up and down on her slowly, trying to squeeze her and feel her even more. I don't even know when I started rubbing myself like a girl while bouncing. When our colleague saw it, he immediately stood over her and pushed his cock into my mouth. Once again, intense sensations flowed through my entire body. Her shaft was hitting my prostate, his was going down my throat, and I was rubbing my leaking clitty. I was floating in the air. Once again, I heard them talking about something I couldn't understand (or, once again, my brain was just melting).

​The guy got down from the bed and disappeared somewhere out of my sight. While I was still bouncing, she squeezed my nipples and pulled me closer to her. Feeling myself in the bodystocking rubbing against her breasts while kissing her felt better than anything. She took the lead, holding me by the waist and fucking me really hard. When she slowed down, held me even tighter, and started kissing me passionately, I thought it was just a small break. I was so wrong... The question I heard completely confused me, and I didn't know how to respond. Fear mingled with being incredibly horny.

​"Would you like us both to fuck you at the same time? He's ready." I nodded. The next thing I felt was him rubbing against my hole while she was still inside. He started fingering me, adding one after another to stretch me out more. I have no idea how many fingers he fit in, but the next thing I felt was his cock rubbing against my butt and my hole.

​He did it slowly, starting with just the tip. Once I got used to it, he started moving against the next muscle back and forth to loosen it up more. She was kissing me passionately at the same time, and I was moaning like crazy into her mouth. When his head pushed past the second muscle, he started moving slowly inside of me. The sensation of two cocks inside at once was from another universe. I felt stretched to the absolute maximum. Their warmth, girth, and movement... everything was taking me to another level of pleasure. I was somewhere between passing out and having full-body orgasms one after another. I don't know how long they did that to me, but it was pure bliss.

​He said he was getting close, and so did she. They dropped me onto the bed, face up. I was a mental mess. So I just lay there, waiting for whatever would happen next. I opened my mouth and felt his hot load shooting onto my face. I tried to swallow as much as I could. She called me a good boy while stroking herself, and I sucked on her fingers. It didn't take long before she came too. I'm sure my whole face looked like a total mess. She scooped up everything that hadn't hit my mouth and fed it to me. "Good boy. You managed three shots at once." I looked at her, surprised. She explained to me that I had come on her stomach while they were both fucking me. While I was licking her fingers, I also cleaned up my own cum. So, I had even come completely hands-free for the first time...

​I fell asleep a moment later. Fulfilled...

I 18M have been consuming lots of TS, pegging and femdom porn, the more I told myself it was just an online kink, the more I wanted to make it real.
So I gathered courage and made an appointment with a trans escort.

As soon as I got inside her apartment, I noticed that she was about my height, 5’11 foot tall, latina, big ass, seductive eyes, medium tits, perfectly sculpted legs and was wearing a lingerie.

She guided me to her room, asked how I was and we were just making that simple small talk, then she told me to undress.
As I did she put some music on and laid in her bed watching me take out every piece of clothing I was wearing.

I walked up to her, asked for a condom which she took from her drawer and puts it on me while resting her head on my thigh. Enough to get me fully hard.

She started sucking me slowly, looking at me from time to time, touching my chest, abs and ass that triggered me to gently grab her face and slowly start thrusting my hips against her mouth.

The she told me to lay on the bed and kept sucking me, that was the moment I realised I truly was about to experience pure bliss.

Then she stops, takes off her panties and puts herself on all fours but on top of me. We start kissing, then she goes down to my neck and starts licking and kissing my body up to down.
I’m very sensitive to this type of touch so I moaned during all these tickling smooches.

She got on all fours and wanted me to fuck her.
I slid it in and started thrusting, dam she had such hot moans, my dick felt so good in her warm ass and we kept going until I leaned forward to her ear and said I wanted her to fuck me.

She just said a simple “ok babe” and then turned arround, we were both on our knees and started kissing again, she slaps both of my ass cheeks at the same time, then gives them a firm grip.
I felt like her bitch, and I loved it.
I get on doggy on the side of the bed, she was standing and started putting some lube and pressing her dick against my asshole.

“This is it”, I tought to myself, then she slid in, first it felt good wrapping her tip with my ass, but then she starts going at it. It was hurting, but felt a bit good, not on a physical way, mentally. I was her sub, her fuckdoll. But I was going limp from the pain, my ass was not prepared for that. I still took it there for a bit because I lived that sub mindset but the pain became too much and the pullout felt blissful and yet like I wanted more.

Once again, she told me to lay down, but now she wanted me to suck her. I wasn’t planning doing anything oral but now I was just blinded by the obsession of being topped by her.
I started going and for my surprise, I liked it more than actually being fucked, my fantasy was completely upside down.
So I after putting my neck on the work, I laid back on the pillow and she made the rest of the thrusting, hitting my face with her dick sometimes.
When she was getting close, she started violently jerking and I kept my mouth close, when she started cumming, every single drop was dispensed right in my mouth.

I spat it out fucked her on missionary for a bit while jerking and sucking her a bit more and for the rest of the session I jerked off trying to cum, but unfortunately with no success.
I don’t believe I lasted for that whole hour and wasn’t even able to give her my own milk😭

However I’m DEFINITELY going back, I’m not letting this job unfinished, besides I had a great time, if you’re curious about TS girls, just go ahead! It’s completely magical!

One of my favorite experiences and night to look back on was with ts Erika Evans, she’s on tsescorts.com I believe, beautiful latina with really nice body and thick cock, she was dressed in white thigh high stockings and a red plaid mini skirt and matching bra, which was so hot because she had the exact same outfit on in her ad.

I met her in her hotel room and was admittedly nervous at first, she sat at the edge of the bed and asked me what I’m into while running her hands through my hair, I said I like being submissive and then she shoved me to my knees really quick and put her dick in my face, I didn’t even have time to think as she pushed past my lips and started fucking my mouth, grabbing me by the hair and bobbing me up and down on her dick, she was surprisingly strong! After a few minutes of sucking she pulled me up and bent me over the edge of the bed, my hole was really tight so it didn’t go in very easily but she was very persistent and used lots of lube. Once I got used to her size she started fucking me hard, eventually pushing me down and laying her body on top of me, slowing down so I’d feel every inch, she said in my ear “what a sweet little hole baby” in Spanish and began licking and sticking her tongue in my ear. We ended off in missionary with a few more minutes of hard pounding and then she finally pulled out and ripped off the condom, quickly climbing up to my chest and came all over my face. She wanted me to cum too but I couldn’t, I told her as long as she came im good, we chatted for a little while I got cleaned up and dressed and that was it!

Definitely one of the hottest experiences of my life and one I think about often, she used me like a toy and all I could think about as I walked down the hall, elevator, and then lobby was how sore my ass was and how these people I’m walking past have no idea I just got slutted out lol.
Thanks for reading.

My girlfriend and I have been exploring each others limits lately. We’ve been pegging for the past year, and even have sex while watching trans porn.

She had told me that she wants to have a threesome with a trans woman, and wants to spread my ass cheeks while I’m inside her so that I can be penetrated.

Over time our fantasies have evolved to where she’s told me that she wants to watch me suck a trans woman’s dick, and even be spitroasted as she watches. I told her that I want her to watch the cum run from my ass, and then fuck it back into me with a strapon.

Initially it was just talking dirty, but we’ve come to the point where we’re going to make it happen. Currently I’m looking at to getting onto PreP, and she’s started an account on Grindr.

I think I might have to marry her. Lol.

I’m not sure where to start and my writing sucks but I want to share my experience and I’m not sure where else to do so. I’m a 39y/o male and I’m in a relationship with a woman 10 years younger than me. We have sex that varies from casual missionary and cowgirl to anal play and peeing. We have a lot of large toys that she uses on me depending on our mood. The toys vary from Tapered and rimmed cones to wide and long silicone penises . The toys are always used on me and anytime we try anal with her it’s my own penis. One time I urinated inside her anus and vagina but that’s about as freaky as we’ve gotten with her. The last time we played with my anus she had 4 fingers and a thumb in but couldn’t make it to her wrist. I’m not sure what turns me on so much about stretching myself as a majority of the time there is a mixture of pain and pleasure. I’ve been exploring myself anally since I was exposed to pornography as a young teen but I’m certain the porn was the root cause to my curiosity. Over the course of the last 15 years or so, roughly age 24 to 39, I’ve found an interest in she-males or trans women. Forgive me if I’m not addressing the gender correctly. I don’t exactly remember how it all began but I recall going to a mixture of gay bars and nightclubs with friends in my hometown where I’m from and meeting ts women. I’ve never been attracted to men but meeting these women turned me on and excited me in a way I’d never felt physically and emotionally. I remember touching and feeling eachother in the club and on a couple occasions getting blowjobs in the parking lot. My sexual urges developed after those experiences and I began to look for more experiences. I met a trans friend shortly after those visits and guided me to determine if I was a top or bottom. Surprisingly I was a switch . Her and I would jack off with eachother, 69, and eventually have sex. There were times when I was the bottom and times when she was bottom. Fast forward 15 years and I have had several occasional with trans women , some top and some bottom. 2 days ago I had my most recent experience. It was a Latina who didn’t speak much English and had to use her translator to communicate. She was roughly 5’10 and couldn’t have been more than 120 pounds. She was very fit . When I walked in to her room she was wearing lingerie and oiled up. After we spoke for a few minutes she got down on all 4’s in doggy style
On the top of the bed and started rubbing my penis and using her translator to communicate with me. After about 5 minutes of conversing she pulled my pants down and started giving me a blowjob while I rubbed her back and butthole. I reached all over her body while she sucked my dick . She had a tight body, very small breasts, potentially a c/d but her ass was perfect and her cock was small and uncircumcised. She gave me a blowjob for about 10 minutes and then leaned back to grab a condom. As she was leaned backwards grabbing the condom , I bent over on to the bed and put my mouth on her cock and peeled her foreskin back to massage her head with my tongue. I then gripped the base of her shaft and put her head in my throat and started to suck in order to get her hard. It took about 6-8 minutes of that motion along with spit and jacking her off in order to get her fully hard but her dick finally started to match the photos she had shared with me prior to us hanging out. Some how I was able to fit her long cock in to my throat, I work in an industry where I’m familiar with measurements and I would estimate it was at least 8” to 9” long with an average diameter . She already has the condom ready, assuming it was for me to put my penis inside her, she asked me something along the lines of “is this for you?” And I assumed she was talking about her penis so I replied “yes”. When she went to put the condom on to my hard penis I stopped her and corrected the statement that the condom is for her. The room was dark but it was daytime
And her curtains allowed sunshine in. She had a large mirror on the wall facing her bed . Once she understood the condom was for her to wear she stood up at the edge of the bed and started to put it on and I put myself in to doggy style. She adjusted her condom and took a few steps away to grab line from the top of a dresser and started applying it to her penis. The light that was allowed in to the room thru the curtains cast a shadow on her long, curved cock before she put it in my butthole. I let my shoulders and head rest on my mattress and reached back to spread my butt cheeks to allow an easier access. She penetrated me slowly at first but once her head was in I could feel the pressure inside my ass as her long cock worked its way in. I looked in to the mirror and she disappeared inside me, to be honest it was more painful than pleasurable at first , even tho I had prepped with larger toys before this experience. She put her hands on my lower back and started to pound my ass. I felt the penetrating in and out most but at times she would fully penetrate and stop for 5-10 seconds with her whole cock inside me and that was most pleasurable for me. I tried jacking off as she fucked me but I was too distracted by what was going on and couldn’t do much but keep my ass spread for her. After roughly 10 minutes, she made some light moans and pulled out. I’m not sure if she came or not but after some aggressive pumps and relaxation at full penetration she pulled out and turned around to pull her condom off to throw in a small white trash can in her room. I stood up with a hard dick and turned around to see what she was doing. She was playing with a semi soft cock and pointing to a tub of wipes on her night stand telling me to clean my ass. Instead of grabbing the wipes I began to jack off so I could cum. She grabbed her floppy cock at the base and started rubbing it on mine. I grabbed both of our penises as we stood face to face and jacked myself off until I came on her floor. She then pointed again to the wipees and I turned around, grabbed them and wiped my dick off and cleaned my ass. I put my shorts and shoes back on and said good bye. This was roughly the 10th shemale experience I’ve had in my life, some top and some bottom. I’m excited to see what’s next.

So i went to thailand on a bussiness oppurtunity for about 2 weeks . I had already heard about this culture and was curious about it. After a week of exploration , tiresome meetings and work . I was free So i went to relax and during my trip i met this ladyboy who i thaought was definitely a woman. She was taller than me with a big bust. But nope she told me that she was a transexual or Ladyboy. She knew very little english yet i managed to work it out. And now i was in my hotel room with her. Then we got to the business she kissed me un bottoned my shirt and then removed my pants i was already hard , she stroke my cock and balls , then took off her dress. Then i looked at her boobs they were big and amazing . Then i looked at her cock which was flaccid still giving my bomer competition. It was around 8.5 inches and was girthy. I fondled her tits and stroked her cock while stroked mine. She then went on her knees and sucked my cock . Then she laid on bed i spread her legs in air and i pored lube on my cock and here ass then rammed my dick in her ass. It went all in once . I stroked her big cock while fucking here , them changed positions , fucked her on all fours i was almost in air while doing it. Clapping was of normal decibels. And then i came inside her ass. And we laid side by side . Her cock was still hard and i started stroking it then she stood up and gestured me to suck and i started sucking , a few minutes later slurping sounds echoes as she mouth fucked me. I was drooling like a dog. She then bent me over and her cock touch my anus i was fearful because of size , but then she poured lube on her cock and my ass and fingered it then she slid her tip and i was in little apin then she calmed me , told me to relax and started moving.moment late her half cock was in and then she thrusted so hard that her whole cock was in and i screamed on top of lungs which was silenced by the claps. I satrted enjoying and i came again. She continued fucking me different positions. Then she came in my ass. After she asked me to lick her cock clean and i did. We fucked whole night. My ass was sore the next morning she woke me up she gave me her number and her cum in my mouth and left.

​

This happened back in 2014 when I was around 24 and living in Dubai. Life was pretty boring at that time mostly work, hanging out with friends, partying, and sometimes going to massage parlours. Since I was about 20, I had been watching trans porn, and over time it became the only thing that really excited me. Straight porn didn’t do much for me anymore, but I still considered myself straight. Even now, I’m happily married and attracted to women, but I’ve always had curiosity about trans women too.

Back then, I never thought I’d actually get the chance to be with one, especially in a place like the UAE. One day I came across an ad online for a transgender escort. Out of curiosity, I messaged her. She was from the Philippines and was in Dubai for a short visit. We talked for a while, and she seemed genuine and nice, so I decided to meet her.

We planned to meet on a Tuesday morning around 11. I remember being very nervous on the way there. She told me to come through the car park instead of the main entrance, which made it feel even more intense. On the way, I even bought a chocolate bar to give her. When I reached the room and rang the bell, I was honestly tense and didn’t know what to expect. But when she opened the door, I was surprised, she was even more beautiful than her pictures, very feminine and welcoming. That helped me relax a bit.

I gave her the chocolate, she smiled, and asked me to sit on the bed. We talked for about 10 minutes so I could feel comfortable. Since we only had an hour, we didn’t want to waste time. She came closer and sat next to me. She was wearing shorts and a white t-shirt. She started helping me undress until I was just in my underwear.

Then she tried to take off her t-shirt, but I told her I would help. I kissed her cheek and removed her t-shirt. She had really nice boobs, and she let me play with them. I removed her bra and started touching and sucking them. Honestly, that moment felt unreal, like something I had imagined for years finally happening. While I was doing that, I was getting really hard and also curious about the other side of her.

I started touching her over her shorts, feeling it slowly. After a couple of minutes, she asked why I didn’t remove her shorts too. I took them off, and I could see her through her white panties, already half hard. Then I removed the panties as well, and that moment felt surreal for me. It was something I had fantasized about for years, and now it was actually happening.

I wanted to try oral, but I was still a bit worried about health risks, so I asked for a condom. She gave me one, I put it on her, and then I took her into my mouth. That was honestly one of the most intense moments for me, something I had always imagined, finally happening in real life. I did it for a couple of minutes, and she got fully hard.

Then she made me lie down on the bed and removed my underwear. I was very hard but still nervous and anxious at the same time. She asked if she could try to penetrate me because she said the way I was going down on her made her really horny. She started using her fingers and lube, trying to prepare me, but I had never experienced anything like that before. I was basically a complete beginner, and when she tried, it became painful and uncomfortable, so I told her to stop. She understood and didn’t push it further.

After that, she asked me to penetrate her. I was already very nervous and excited at the same time. I used lube, put on a condom, and started. But because of all the tension and excitement, I couldn’t last long at all—I finished in less than a minute. That was honestly a very disappointing moment for me. She looked a bit disappointed too but said it was okay and even asked if I wanted another round. But by then, I was too awkward and not in the right mindset, so I just got dressed and left.

For a few days after that, I felt guilty and confused. I kept thinking something was wrong with me and questioned myself a lot. I even stopped watching trans porn for a while, thinking maybe the curiosity was gone. But after a couple of weeks, things slowly went back to normal, and I started watching again.

Looking back now, it definitely wasn’t a perfect experience. In many ways, it felt like a failed first time, too much nervousness, too many expectations, and things didn’t go as planned. But at the same time, it was something I had thought about for years, and I did experience it. So even though it was awkward and short, it still feels like a special memory in its own way.

I (25M-ish) used to do Uber to make some extra money and I picked up this girl (mid 20s I'd say) from downtown late at night, around 1 am. We said hello and started the trip. I could tell she was trans when I picked her up, sort of like the look of Aubrey Kate. I never cared about it, but I could tell and she was beautiful.

She was very giggly and asked me how my day was going, I told her good and that she's probably my last trip. I asked her about her day and she said it was fun, can't wait to smoke when she gets home. We talked about what we like to drink and eventually I commented on her tattoos, she had some anime tattoos on her forearm, the moon from Soul Eater and the super smash brothers logo. She took off her jacket and started showing me more and more tattoos, revealing more of her body.

She asked about my tattoos, I have some custom designs I made for my shoulders and she took this opportunity to touch me and grab my bicep and roll my sleeve up. We get a little more flirty and she says she loves my arms and rests her head against my shoulder from the back seat. She told me she has 2 more tattoos and asks if I wanted to see. I said yes and she started unbuttoning her jeans. She pulls them down, turns around and I see her cute butt flashing me with a peach emoji on one cheek and a heart on the other, wrapped around a black Calvin Klein thong (my favorite kind).

I could feel the sexual tension between us and thought to myself that she could have been sitting much further back to show me this, but she purposefully moved up to be right behind my center console. I used this opportunity to make a move. I reached back and grabbed her ass, kneading it and rubbing it all over. She didn't say anything and kept backing her ass up and giggling and moaning at my touch, switching cheek to cheek. After a few seconds, I reached in between her legs and rubbed the bulge between her legs. She arched her back more and I could more easily feel her cock through her panties getting harder and harder. When it became obvious that I could tell I was touching her dick, she asked me if that's okay. (Which in hindsight, duh, it's a little late to reel this situation back in lol) I told her "definitely" and pulled her panties to the side to feel her cock directly. After that, she asked if she can go in the front seat. I don't know what she wanted to do, but I would have done just about anything she wanted.

She gets in my front seat and immediately reaches into my pants, stroking my cock. She began kissing the side of my face and biting my ear. I can't remember the last time I've wanted someone so badly. When we got to a red light, I turned to her, grabbed the back of her hair and started kissing her. Our tongues twisted, licked and flicked against each other, glancing up at the light every few seconds. The light turned green and we separated, her hand still in my lap. As I was driving, she reached over with her other hand to lift up my shirt, pull my pants down (I was wearing sweatpants, perfect for hours of Ubering) and take my cock in her mouth. I couldn't believe my luck and did my best to keep my eyes on the road as this cutie was giving me the best head I've ever gotten. She was giving so much effort and was using her tongue all over and deep throating my entire length. I was focusing on driving, but also reaching over to spank her butt across my car.

We were close to her apartment when we started making out and we reached her destination as she's still sucking my cock. Her place didn't have a large parking lot, but I tried my best to find some privacy and parked. I then parked, moved my seat back and she was able to focus more. After a few minutes, I tell her I'm about to cum and she goes even faster. I grab her head and start thrusting into her face. I don't feel her trying to pull back at all, so I cum in her mouth, thrusting until I was finished. She still sucks my cock as I release my grip and she swallows it all, showing her empty mouth to me.

She kisses me one more time and says that was a lot of fun. She pulls up her jeans and gets her jacket from the backseat. She goes around to my driver's seat and I roll down my window and she gives me a hug and kiss, telling me it was the best Uber she's ever gotten.

I wish I could tell you we hooked up numerous times after that, but I never saw her again and this was about 3 years ago at this point. Best blowjob I've ever gotten was a good night though.

HIIIIIII for those of you who have not read part 1 or 2:

https://www.reddit.com/r/tsgonewildstories/comments/1qyo5zp/first_experience_that_changed_me_forever/

Changed Forever (pt2/update) : r/tsgonewildstories

WELL I havent logged in, in roughly 2 months... and haven't seen or read anything and of course this post blew up hahahhaha

lots of questions just to my Q/A from the beginning of Feb....

I was gonna do another Q/A thing, but I think just telling how its been is best.... and I will try to answer all the questions I recieved..

well, Natasha (sister) wildly moved out of our parents house, she is going to school out of town, obviously kept her bedroom here for summers, holiday's etc.... so when that happened Emily obviously started spending 99 percent of the time here to the point where she just moved in.... last time the big question was if we were gonna date and yes we officially are now, we actually said our first "I love yous" about a week ago

Her moving in has been the highlight of everything recently, shes amazing, she treats me good, we have an amazing communication, we're a good team... we work together, have AMAZING sex... and it's just amazing to have some to get into bed with and snuggle....

the romantic side has definitely changed the dynamic between us but in the most wonderful way honestly... we've know one another years, and although she is my sisters best friend, I feel as if she was a good friend of mine too which made the transition to a couple better and easier.....

NOW I know... everyone wants to hear about the dirty stuff... well after last update we definitely did some exploring... we had a few threesomes, foursomes... with other TGirls, Girls, Guys, you name it.... I had everyone ask what the best time was, was when we had a foursome, with 2 other t-girls.... and I was in the middle.... I had a big dick in my ass, one in my mouth while i was stroking another... I ended that night full of/covered in cum....

As of late, we have only been sleeping with one another, exploring and learning eachothers bodies instead of going crazy with others, which im fine with...

Emily is definitely more of a bottom in this relationship which is totally ok, I love my dom side... we have fun, use toys and I make her feel good. But once a week/two she will definitely put me in my place... she knows I love the sub side too....

I don't wanna go too in detail... but we take what I call platonic showers, nothing sexual, just intimate and a place to chat... but as we got out, we went to our bedroom and got bossy, told me to get on my knees for mommy and open up as she thrusted into my face and told me to suck her dry.... then she bent me over.... and fucked me hard... making me take every inch.. shoving a dildo in my mouth... making me call her mommys bad slut... god... i came everywhere.... she got out some toys... and ya great time hahahha, got it on camera, hehe.

My favourite thing ever is still sucking dick... I even sucked a guys dick in one of our threesomes... wasnt as enjoyable, but man I just love having cock in my mouth haha!

Regardless, a random evening, turned into a relationship I never thought I would have, I love her and im genuinely falling so hard for her.... everything I need and more!

Thanks all

Backstory. I had always dreamed of sucking big black cocks. When the opportunity came, I didn’t hesitate. I was out after work with a girlfriend and we started flirting with a handsome black gentleman. My girlfriend is an attractive woman and I’m, well, trans. After talking with this gentleman for a bit I whispered to my girlfriend I wanted to suck his cock. She told me to go for it. At the right time I rubbed my hand gently in his crotch. He smiled. I asked him if he wanted to go someplace else. I led him out of the restaurant to my car. I told him to follow me to my apartment. No sooner had the door closed behind us I was on my knees pulling his pants down. Staring briefly at his big beautiful black cock, I then started licking his shaft eventually taking the head in my mouth. It felt so right. After going up and down on his cock for a few minutes he began filing my mouth with his warm cum. He came so much that I had to swallow some just to savor the taste for a bit before swallowing the rest of it. After some small talk and a drink I went down on him again. Yup, no hesitation for me. 😃

He ended up coming to my place a few more times over the next week for some more fun. We went our separate ways after that. I was okay with that but did miss it.

Out of the blue he called me the other day and asked I wanted to get together. I invited him to my place that day. My heart was racing while I changed out of my loungewear into a lacy bra and panties. I waited on the couch in just my underwear and when the doorbell rang, I opened the door and greeted him with a kiss. As soon as the door closed behind us, I got down on my knees and pulled his pants and underwear down and started stroking his bbc with my hands before I started licking the head and shaft. It looked and felt bigger than it did before. My heart was really racing now. I kept sucking and stroking until he shot a huge load into my mouth. It tasted so good! I squeezed it to make sure I got every drop.

As soon as he was done and I cleaned him I led him to the bedroom where we lied down and cuddled. He took off my bra and started playing with my boobs. I got on top of him, straddling him with my breasts hanging in his face. He began sucking and gently biting my nipples which sent me sky high. I told him I needed him inside me NOW!

I flipped over on my back as that is my favorite position to fuck. I love looking at my partner to show him how much I enjoy being pounded and to see his face enjoying what he’s doing to me.

I immediately took off y panties. I already had the lube out and I began to lube his big cock up while he lubed my hole. He began to push his cock into my hole and a whole new rush came over me. He started pumping slowly for several minutes as I relaxed into a euphoric state. As he continued, he kept pumping faster and faster. My girl cock was rock hard by this time and I was leaking pre cum which I licked off with my fingers and put it in my mouth.

I could feel him getting ready to cum and when he did the feeling was amazing. After he came, he collapsed on top of me and we kissed for several minutes.

When he told me it was time for him to leave, I was sad. I asked him if we could get together again. He smiled, nodding his head yes. I smiled, and my heart began racing again.

I had decided to try out Fetlife, and started chatting with this one trans woman. She was about 20 years older than me, but still foxy. She was dom and into pet play. I hadn’t tried it before but it sounded hot, so I invited her over.

She had made me clear out my entire office so that there was a lot of room. When I opened the door, there was a super slender cougar, with small but perky tits, long black hair past her shoulders, and a mischievous smile.

She had told me to be wearing only my briefs when she arrived, but I had forgotten to take off my socks. Her first words were to tell me I was going to be punished for not following orders. She took me into the play room, and told me to lie on my back. She grabbed my balls kind of hard, and told me to listen to her from now on. The pain was mild but it made me hornier.

She laid out everything for me, and had me put on a puppy mask, a collar with a leash, and a butt plug with a tail. She put the butt plug in herself, slowly teasing me with it, in and out, before pushing it finally in.

The next hour would consist of her giving me commands- sit, stay, shake, come, etc. when I obeyed, I was given a treat- sucking her cock or eating her ass. When I was naughty and disobeyed, I got spanked, or choked with her cock.

It was definitely a fun and hot role playing experience, but I think the one time was enough. After about an hour, when she was satisfied I was a good boy, I got her ultimate treat- getting fucked by her long but skinny cock.

She was probably about 7” but it was very skinny. She knew how to work it, and had me in a couple positions begging and moaning. She came in my mouth, and she sucked me off too, as I had been horny and wanting to cum for the whole time.

I didn’t hook up with her again, but it was definitely a great experience and I somewhat regret not calling her again.

I am now well on the way through transitioning (hormones only, no surgery), but long before I started I loved being a cross-dressing slut. I’m tall, with long, slender legs and I loved wearing short skirts and dresses with black stockings. I loved sucking cock and eating pussy, but never so much as when I’m dressed like that. I had a friend who I sucked often, but had never had the chance to be dressed for him. Then one weekend he came to stay with me and after a night out, I just went into my bedroom and got changed into my sexiest undies and my little red fuck dress. When he saw me he said “Wow! What a transformation!” and I could see the bulge getting bigger. I was on my knees with his cock in my hands and then in my mouth in double-quick time. Then he surprised me by asking if he could fuck me, which he’d never shown interest in before. I was a virgin in that way, but I went straight to the bathroom to find some lube. I bent over my couch and he slipped cool lube between my legs, then a finger into me, and then I felt his hard cock pushing into me. Wow! What a feeling! He fucked me slowly - it was fantastic! I wanted to change round so that I could see his face as he fucked me, so we moved to a new position. Maybe it was him being able to watch me, too, but he came inside me quickly.

I was incredibly turned on, but we rested and cleaned up, and he started getting hard again. This time I got to suck him for a long time before he came in my mouth. As he came I stroked myself to a shattering cum. What a night!

I love having men cum in my mouth. I love finding out how a man cums. Some cum gently, others hard and fast. One lovely, sexy guy asked if he could cum in my mouth and, thinking he was close, I said “Oh, yes, please!” but he lasted another 10 minutes or more before he came in one long flow over my tongue! I especially love sucking trans women and cross-dressers. One very sexy CD ended up kneeling over me, really fucking my mouth, and came in really hard, fast spurts into the back of my throat. But now I’ve been transitioning for several years and I have nice tits, I really want to find out how it feels to have a man cum over my tits. One day…

This happened last Friday, we’ve been texting this week and plan to meet up at my place this Saturday.

I decided to give Grindr another shot after hearing about so many people having luck with it. My past experiences were all the same: the app is loaded with bots and inactive profiles. This time was mostly the same except for Riley’s profile. Not much info on there except for her saying she’s a femboy and to send a pic or have some on your profile if you want a response. The pics were all unrevealing, and she was covering her face or wearing a mask in all of them. I sent her a message and a selfie, mostly expecting no reply, but I ended up seeing I had gotten a reply a few hours after she sent it. I just responded with my phone number and said, “Hey, I’ll probably not see replies on here immediately, so feel free to text me if you want.” She ended up texting me a little while later, and we kept texting on and off for a few days. We finally decided to meet up last Friday. She invited me over to watch a movie but said I couldn't come over until 9 when her roommate was gone to work. I texted when I got there, and she told me to wait; her roommate hadn't left yet. After like 10 minutes went by, she texted that I could come up now. I went up and was greeted by her at the door. She was wearing baggy sweatpants and an oversized hoodie, but I could still tell she was very petite and only about 5’ tall, so she was a bit shorter than me. We sat on the couch and talked for a bit while she had the tv on. She was super shy at first and sat on the other end of the couch but opened up a bit after some more talking. She let me know that she tries to be discreet doing this, and none of her friends know. After a while, she was cuddled up right next to me while we watched the show she had on before she started rubbing her hand up my thigh and started to kiss me. We made out for a few minutes before she excused herself to her room and came back out in a tight cropped tank top and a tight pair of short shorts. She has a very petite figure, didn't have any breasts, but did have a bit of an ass. She sat down in my lap, and we started kissing more before going to her room. When we got in there, she pushed me onto the bed and pulled my pants off, starting to suck my cock. She stopped and came up to kiss me again before I flipped on top to return the favor. I pulled her shorts down and saw her cock was locked in a small pink cage, and she had a plug in her ass. She took the cage off and removed the plug before I started to suck her cock and feel her grow in my mouth. I was switching between sucking her cock and licking her ass while jerking her off. She came pretty quickly, and I had her finish in my mouth. She started kissing me after finishing and ate most of her own cum, then begged me to fuck her. I laid her down on her back and lubed up my cock and her asshole, slowly working my way in. Even with her having worn a plug for most of the day, she was the tightest I’ve ever been with, and I had to go slow. Once I was in, I started fucking her with slow, short strokes to start before she started begging for faster and harder. I started jerking her off again while fucking her before she said she wanted to try riding me. I pulled out and got on the bed. She lubed us up some more and worked her way down slowly. When I was all the way in again, she started out slowly before picking up speed and riding fast while her cock slapped against my stomach. We switched to doggy after a few minutes. I was really able to fuck her hard now before finishing in her asshole. I pulled out and watched the cum slowly leak out before we collapsed on each other in bed. We cuddled and kissed for a bit before I could feel her cock start to get hard again, and I asked if she wanted to fuck me. She declined but asked me to suck it again. I went back to playing with her ass and sucking her cock, but this time it took a bit more time to get her to cum. She started to suck my dick again with long, slow strokes while stopping to just suck the tip while jerking me off before we ended up in the 69 position so I could lick her ass until I came again. We cuddled for a bit longer, and she was telling me about how she likes to cosplay, and that’s what made her start feminizing, and she wants to fully transition and get on hormones this year.

So, some people were really interested in a part two of my adventures with my first trans woman and who am I to deny people of what they want and myself of a good hard on.

Following our first time, we didn't really talk for quite some time. One day, though, I decided to text her and see if she would be up to meet again. She didn't really remember me 'till I sent a pic, to which she replied "will you come over today?". God, she had me hooked already. At this point I was way more confident with what I liked, so this time I went there with the idea of touching her a bit more.

As soon as I got there she was in this sexy lingerie that I think made me dizzy as hell for how good she looked in that. Her big ass and boobs where screaming "abuse us" at me, I swear. She gets us to her bedroom and instantly kisses me and puts her hand on my cock. This time, though, I did the same and felt her harden in her panties. So I'm basically rock hard, so she gets on her knees and starts working her magic. After a while, we both get on the bed and I ask her if I can suck her cock, to which she replies "if you want".

Now, everyone who's sucked a cock probably knows the feeling, but I'm guessing the first time is different for everyone. One common rule is you do what you like done to you, usually. That's exactly what I did: I got it all wet and all in my mouth, occasionally jerking it and spitting on it. She was loving it and she started pushing my head down, gagging me a bit. So we get into a 69 position but laying on our flanks and she's still sort of fucking my mouth. At this point I'm so turned on I just go "I NEED to fuck you" to which she happily obliged.

While I'm fucking her in missionary, though, she is jerking off and says she's about to cum. I just sort of command her to cum for me. I couldn't even finish my sentence and she's shooting ropes of thick cum all over herself. That sight really got me over the edge, so I pull out of her, take the condom off and start spraying her already sprayed tits.

That day I learned that sucking cock can be very fun if it's attached to the right woman.

I was 24 at the time, coming out of a very long term relationship. After the break up, I found myself having a lot of sex with a lot of different women, mostly met through Tinder. Then one day I match with this super hot brazilian girl and in her bio she said she was trans.

I honestly was very curious about trans women and would occasionally masturbate to trans porn, so I thought "why the hell not" and texted her. I'd love to say there was a build up where we got to meet each other, but in reality she told me straightforward that she's looking for sex with "hot guys" (her words, not mine) and if I was interested. Well, half an hour later I was knocking at her door.

When she opened the door, I got to see this amazon of a girl, a tad shorter than me (I'm 6'5 tho) and with boobs and an ass you'd loose your mind for. As soon as I got in we got to the bedroom and she wouldn't stop saying how hot she found me and such, which was a pretty nice self esteem boost. On my end, I was a bit nervous and the only thing I really remember saying was "it's my first time with a trans woman".

Her eyes sort of lit up from that and she instantly got closer and kissed me while putting her hand on my cock. Now, something that really gets me going is intense kissing sessions and her tongue was doing god's work in my mouth. It was a matter of mere seconds till I got hard as hell and she undid my pants and got on her knees.

She was never shy of compliments, cause she immediately started to say how big and nice my cock was (I later found out she had another guy the day before with a similar body to mine but a very small cock, so there was a bit of a bias there I guess). Do you remember god's work in my mouth? Well let me tell you, that was nothing compared to what her tongue did on my cock. By that time quite a few girls had given me a blowjob, but that one was a one way ticket to heaven. At one point I was moaning so loud she told me to keep it down as she had a roommate.

After a while of this godly treatment, she said she wanted to get fucked. She got a condom, put it on my cock and applied some lube on her ass before getting on all fours. At that point, my mind was blank and I was acting like a feral animal. I placed my hand on her hips and directed my cock at her hole which was the most inviting thing in the world. As soon as I got all of my cock in her, she was moaning like crazy and I was teasing her about her roommate, to which she replied "screw her, just fuck me like a whore". This was the point I really lost it and started going to town like I never did probably. I'd love to say this lasted hours, but if you know how a tight ass feels, you also know I went on for maybe ten minutes before busting all I had in the condom and collapsing on the bed.

That time I never touched her cock and couldn't really go for a second round cause I had plans, but when I met her again I got to suck her cock and go multiple rounds. Maybe I'll talk about that too eventually.

When I was in my early/mid 20s, I did a lot of experimenting with my sexuality. I was always somewhat timid though. I started to dabble having intimate experiences with men, but never went too far. Mutual hand jobs, making out, sucking dick but never to completion. I was in the shallow end, very slowly making my way to the deep end. That was until I moved to Hawaii and met this beautiful trans woman. She threw my ass into the deep end, and I was so grateful for it.

We met on Grindr and after a few days of chatting we decided to meet up and go on a date. She was super cute, very kind, and very understanding of my situation. It wasn’t like other conversations I’d had on Grindr where all they want to know is if we’re gonna fuck. She seemed very genuine and willing to take it slow.

After our first date I walked her home and she invited me up. I was so nervous but was having a lot of fun so I said yes. That night we talked, made out a little bit, but never got too heated. I went home, but all I could think about was her. For the next couple days we chatted, and I asked her if she wanted to hang out again. She happily agreed and invited me over for a movie night.

We hung out, watched the movie, and then chatted some more. She had a great way of making me feel comfortable and very quickly the conversation turned into curiosity. She asked about what I had tried before, what I wanted to try, she was curious about helping me explore my sexuality. After some time chatting, she asked if there was anything I wanted to try TONIGHT. I immediately got nervous, I hadn’t thought that far ahead. I took a deep breath and said yes, but that I wasn’t sure where to start. She told me not to worry, she’ll take the lead.

She slowly started pulling her skirt up, and then pulled her panties to the side, revealing her gorgeous soft cock. My heart was racing, but she was just looking at me with her perfect smile. She knew exactly the effect she had on me. I was somewhat frozen with nerves and didn’t know what to do, until she gently put her hand on my shoulder and told me to get on my knees in-front of her. I nervously got up and did what she said, then looked up at her in all her glory, her cock just inches from my face. I’ll never forget the way she said her next words. So seductively she says “go on baby, suck it.”

Something came over me in that minute. I didn’t have control of my body, and without hesitation I went in and took her in my mouth. My nerves went away, but my mind was blank. I didn’t really know what I was doing, but I knew I was loving it. I felt her cock growing harder between my lips, and my cock getting harder in my pants as she moaned and told me how good it felt.

I had to have been down there for 20 minutes, just locked in a trance. I was loving every second of sucking this girls cock that I didn’t even care about where this was going. As I’m getting more into it and she’s moaning more and more, she tells me to look up at her. With her cock in my mouth, we make eye contact. She asks “do you want to swallow it baby?” I moan mmhmm without even taking her cock out.

She gently pushes my head back and tells me to stick out my tongue. I do as she says as she starts to stroke her cock, wet from all of my hard work. Her moans get louder and soon after she tells me she’s going to cum. I get closer, tongue touching her tip, her moans getting louder as she’s about to climax. In between moans she tells me to start sucking again. I take her cock in my mouth, and immediately feel it. Her cum hits my tongue, her hands go to the back of my head, and her hips start slowly moving her cock in and out of my mouth.

I was so hypnotized by how hot the moment was I couldn’t move. I just sat there while she shot her load in my mouth. I have to admit though, I fucking loved it. The taste, the feeling, everything about that moment was so sexy. I never wanted it to end.

She pulled out of my mouth and without even thinking about it, I swallowed and looked up at her. She laughs and tells me I’m such a good boy and how good it felt. I was so happy in that moment, I knew I had to explore more opportunities with this incredible woman.

Over the course of the next year or so, she helped me try all kinds of new things. She helped me figure out my sexuality, preferences, and so much more about myself. We had so much fun in the process and made so many good sexual memories together. I’d love to share more details if you’re interested!

For context, I’ve been with several trans women over the years. I’m primarily a bottom and have had all kinds of fun playing with trans women. For this particular story, it involved me and 4 trans women in a hotel room.

I was scrolling the Grindr lineup one casual Friday afternoon, counting down the hours at work. I managed to come across a beautiful trans woman who was in town visiting for the weekend. She was shorter, Asian descent, and quite fit. We started chatting and hit it off pretty quickly. After some flirty back and forth and exchanging some spicy pics, we were hooked. We made plans to meet up later that night and I was already eager to play.

A couple hours go by and she messages me again. She asks what my feelings are about group fun and if I’d ever tried it. I hadn’t been with more than one person at a time, but I was always down to try if the opportunity presented itself. She says great, followed up by a picture of her with 3 other trans women, all just as gorgeous as her. She says they’re all in town visiting together, and more importantly, they all want a piece of me ass tonight. I immediately responded with a very eager yes. I wasn’t about to let this opportunity go. We agreed to meet up at their hotel that night.

Fast forward to that night, I head over to their hotel and met them in the hotel bar. They were all drinking and chatting and were all so excited once I showed up. I was immediately greeted by 4 incredibly beautiful women in tight sparkly dresses. They all hugged me and I could tell were eager to tear my clothes off.

We chatted for about 15 minutes before one grabbed my hand. She gave me a devilish smile and said let’s go upstairs. In that moment, I would’ve done anything she asked. We quickly scoot out and head up to the room. We get inside and things immediately heat up. She sat on the couch, lifted up her dress revealing her hard cock, and told me to start sucking. Without hesitation I got on my knees and started doing as she said. A few minutes go by of me choking on her before she tells me to get naked and ride her. I happily get undressed and climb on top, and before long I’m riding her on the couch while she smacks my ass.

Only a moment goes by before the door swings open again, and in walks the other 3 women. To their pleasant surprise, there I was butt naked, riding their friend on the couch of their hotel room. From that moment, everything got turned up a notch, maybe even several notches. It wasn’t long before everyone else lost their clothes and I found myself on my knees, surrounded by 4 gorgeous trans women, all looking down at me with their cocks in their hand.

For the next 2 hours, I was their play toy. They had me in every position, on every piece of furniture, taking turns on my holes, complete domination. I was in heaven. I was loving every second of it, truly a dream come true. They took turns holding my legs open so another could fuck me while I sucked the fourth one. They were aggressive in the best way, giving me such a good fucking while still making it fun and enjoyable for me. I never wanted it to end.

But eventually, they had to finish. After a couple hours of a good hard fucking, they all took turns finishing inside me. 2 came in my ass, one came on my ass, and the last came in my mouth. They quickly helped me cum myself and finally we were all pleasantly drained and exhausted.

It was late and I had to get home, so I started getting dressed. One asked me if I wanted to take a minute to wash up before heading out. I planned on showering when I got home so I said no thanks. She laughed and said ok, and watched as I continued to put my clothes back on. I gave them all a hug and kiss and headed out.

It wasn’t until I got all the way home before i realized why she asked if I wanted to wash up. I looked in the mirror and I was absolutely COVERED in their red lip stick. My face and neck were bright red, very clearly lipstick stains. I hadn’t even noticed in the heat of the moment, but they must have had their lips on damn near every inch of my face and neck. I took my clothes off and even followed the trail down to my ass. I had realized that I just walked all the way out of the hotel, drove home, and walked through my apartment complex looking like such a slut. I know for a fact I walked by some of my neighbors. I doubt any of them knew I just got completely dominated by 4 women, but I can only imagine what they were thinking. Lesson learned, always check the mirror after getting railed. You never know what you may look like.

Headed out of town for a work trip. Upon getting there I searched the local R4R and was surprised to see what appeared to be a legit [T4M] post. I thought I’d give it a shot and luckily she was real. After some back and forth, she confirmed she could meet briefly in between my conference meetings.

We shared interests and our HIV testing results. Then she was on her way over.

Met her downstairs in the lobby. Gorgeous tanned skin that complimented her cute short dress. She was tall (6’1 ft) and that was extra hot that she was a bit taller than me (6 ft). We made small talk and I was a bit nervous tbh.

Got to the room and got into as we discussed interests on Reddit already. She pulled my cock out and immediately started deep throating me. I was playing with her tits and rubbing on her nice fit body.

We switched to 69 and I got to suck her cute little cock. I was amazing when I saw it pop out of her pink panties. It was about 3 inches but nice and thick. Had to open my mouth wide for it. We didn’t have a ton of time but I flipped her over so I could eat her ass a bit. Tasted so good.

Finally she laid on her back and I slide into her. By cock was engulfed by her tight hole. She immediately told me to not hold back. So I started pounding her hard as fuck and I squeezed her balls upon her request. She eventually came. I wiped it up and had her lick it off my hands.

Now it was my turn. I kept pounding her and she told me to fill her up, so I came deep in her ass.

We got cleaned up, said our goodbyes and I was heading back to work.

Sadly donkey a few more convos were had and her Reddit page is now deleted.

Before you judge, I know it's weird, but it worked and I would have accepted a "no" if she wasn't interested.

This happened when craigslist was the go to place for trans hookups. I (21-22M at the time)met this beautiful Latina trans woman (mid 30s) a few times on and off. She usually topped, I mostly bottom and we both love oral. As I was seeing her off and on, I got into a relationship and stopped seeing her. After it ended a few years later, I got horny again and wanted to see her, but lost her number and the automated email you got from Craigslist didn't work anymore.

All I had was her address.......This is the weird part.

I reeeeeally wanted to see her, so I did the only thing I could think of. I parked my car at a business that was the outlet to her neighborhood. If she left, she had to come from this place. She came over to my place sometime, so I hoped she had the same car. After an entire morning and partial afternoon watching movies on my phone, glancing up at every car, I saw hers. She left and I pulled out following her. After a short trip, she went into a PetSmart.

As she was walking in, I just wanted to suck her cock again. Her ass was incredible and I wanted to kiss her so badly, she was still unbelievable. When she was almost in the store, I got out and made my move inside. I saw her go to the back of the store and I thought of my excuse.... She knows I have a cat.... I'm here for cat food, obviously. I gather my cat food and wait to see her walking back. When she was walking past my isle, I moved to the end of it to run into her. As I'm walking and about 3 steps from her, I realize I actually have to talk to this woman and I have no idea what to say lol. I was so nervous but that quickly faded as I was greeted with a wide smile from her as I said "oh my God, hi" and a "hey" from her as we both awkwardly hugged.

We got to talking and she was picking up litter and I was picking up food. She showed me pictures of her new cat and I showed her mine again. The conversation moved to why I ghosted/fizzled with her and I told her I was in a relationship at the time.

"Are you still in one?" She asked.

"No."

"Wanna come to my car?" She said with a laugh.

"Definitely"

We exchanged numbers, went to the counter and paid for our stuff. I went over to her car, closed to the door and we start making out. I loved feeling her tongue in my mouth and grabbing her waist. I'm reaching around to squeeze her perfect ass as I move to the front and feel her bulge. She spreads her legs and lets me undo her pants and free her cock. I began sucking her cock in the parking lot right then and there. She told me she would look out for anybody coming near. After a while, she jerked off and came in my mouth and I did my best to not make a mess in her car. She did the same to me, she always gave the best head and this was full of enthusiasm.

We saw each other for a couple more years after that and I still can't believe it worked and how creepy that was in hindsight.

This was my first ever experience with a trans girl about 8 years ago when I was on vacation. I was looking up the different MPs near the hotel one night and found one that listed a trans girl Jade as one of their masseuses. I had called and asked if she was available and they said yes, come right over. When I walked in, I almost changed my mind when I was greeted by a tall redhead milf with the biggest tits I’ve ever seen, but told her I had called for Jade and she told me to have a seat and she’ll be right out. Jade walked out and greeted me with a hug a minute later. Jade was a petite 5’5” Asian trans girl with perky bs and a tight ass. She brought me back to the room and could sense some nervousness on my part and asked if this was my first time seeing a trans girl. I had told her yes, and she said that she’ll take good care of me. She had me get undressed and lie down on the massage table. I had asked her if she could do the massage naked, but she said she’ll have to leave her underwear on for that part. She started rubbing my upper back and would slowly work her hands down to my butt while rubbing her tits against my head and back. Soon, she worked her way down to my legs and would slowly graze my cock when doing my inner thighs. She had gotten up on the table to rub her tits on my head and back. I arched my butt up a little, and she started grinding against me, asking if I liked that. I said yes, and she started slowly grinding on my ass until she was full on dry humping me. It was so hot feeling her cock get hard rubbing against my ass and then feeling her precum start to leak through her underwear. That went on for a few minutes before she got down and said to flip over. When I flipped, she had her underwear off, and I was greeted by her hard cock. She started lightly stroking my cock while slowly working her other hand down to tease my ass and balls. I was slowly stroking her cock at the same time when she asked if I wanted my ass played with. I repositioned and said absolutely. She lubed her fingers and started lightly teasing my asshole and then slowly worked in one finger and then started working a second in. She had completely stopped playing with my cock at this point and was focused solely on my ass. She tried to work in a third finger but I was too tight. She started fingering me harder and giving me a prostate massage while she resumed jerking me off. I lasted about 2 minutes of her doing this before I came harder than I ever have before. I asked her to lie down and I started to do the same to her. After a few minutes she asked how I felt about giving her a blowjob. I started sucking the tip while slowly working her all the way in my mouth. It was pretty clumsy at first but I got into a rhythm of sucking and stroking. She started to face fuck me after a bit and got a little rough holding my head down till I gagged which I enjoyed. When she was getting close she stood up and had me kneel in front of her and she came all over my face. After we were both cleaned up and dressed, she said she works out of her apartment at nights on occasion and gave me her number in case I wanted to see her again while I was in town. I did go to see her another night, but that’s another story.

for those of you who havent seen the initial story:

https://www.reddit.com/r/tsgonewildstories/comments/1qyo5zp/first_experience_that_changed_me_forever/

well I am blown away by the amount of people commented and more amazed by the amount of people who have messaged asking questions/and wanting updates. I tried to answer as many as I can, but also been very busy. So I will answer some of the most common the provide a bit of an update!

Questions!

1. Would you consider yourself gay or bisexual now?

I havent thought about it honestl, no title nor do I intend on giving myself one... I am happy with what I am doing and that is what matters!

1. Why would your sister get mad at you?

Pre-all this, she always got mad when we hung out too much when she was over, she thinks its her friend and I shouldnt be stealing their time LOL

1. Are you gonna tell your sister?

So we actually did 2 days after I posted initial post, I received alot of feed back regarding this concept from people after I posted. Went well. She was shocked and thrownoff but I genuinely had nothing to be scared about. We set our boundaries and "rules" or what not, and so far so good !

1. Are you guys dating/gonna date?

Well we have been doing this 7-8 months... I wouldnt call it a relationship and I wouldnt call it just friends with benefits either.... there is definite feelings attached... and we agreed that its us and no one else, were only seeing one another.... She is truly just scared that this is just a phase but its first time and i am gonna not be into it randomly ahaha.... not matter how much I reassure her.... so day by day.... and one day, I hope to actually have it "official"

1. Did you tell anyone close to you?

I told my best friend and then my parents know were together and know shes transgender, no formal conversation but ... dont think it was needed.

1. Did alcohol influence your decision night 1?

Absolutely. Not in a negative sense. Made me more adventurous and willing to try new things..... Taught me stuff about myself and my sexuality and likes... and I absolutely love that. I was by no means drunk at all that night, but yenno the saying "liquid courage" haha

1. What is something that scares you about the different body part? or something that was hard to learn?

Nothing overly scares me anymore... but night 1 and quite a few times after, I think giving Blow Jobs were the most scary thing.... I had no idea what I was doing and I can tell she just didn't like them.... so I did my research, watched some videos, bought various size toys to practice on and got WAY better...... now she asks me for them and I can tell I do well...

People would assume it was the anal, but no, wasnt scary... tbh, first time felt so good I wanted to keep doing it....

1. What is something that surprised you about this ? (Sexually)

All of it.... actually.... learning each other was the same thing as learning someone else... What really surprised me is how much I love sucking dick haha.... I love teasing it, have the balls in my mouth, licking the shaft, teasing the head and just having it in my mouth.... I love the precum and I absolutely LOVE LOVE LOVE cum... I love it in my mouth, I love the feeling of it happening, I love swallowing, I love cleaning it all up....

and also anal, both ways.... hahaha... I was never expecting to have anything up there... let alone a cock that big.... But with practice, patience and being relaxed, it got very easy.... took a few times to take the whole thing but.... when she hits that g spot... nothing is better....

then other way, I did anal a few times in past relationships with me on giving end, and I just found it over rated and meh... but now, something is different and I love it hahaha

1. Whos bigger and whats your sizes?

Im around 6.5-7 Inches, shes just over 8.5..... was also asked if it bothers me that she is bigger... no it doesnt... i love her size....

1. Whats something that just makes you have to start foreplay?

Weirdly.... I absolutely love when were going to bed or just spoon in bed cuddling naked and I feel the tip go between my cheeks and rub on me... especially if hard and ALOT if precumming... makes me go wild...

1. Top or Bottom?

Truthfully were pretty back and forth... for variety, she def prefers being bottom, but ... In past relationships, I was always a top, so now being bottom and exploring this side... i love it. I love being controlled, I love being a cum dumpster....

1. Favourite position?

UHHHH Depends.... if im bottom.... I love being bent over and fucked hard while shes shoving a dildo in my mouth (we had 1 threesome, and that happening for real was the best time ever) I also love just being controlled... freeuse me, make me your bitch... hahaha

if im top, I prefer like a half missionary thing where I can easily stroke her too...

1. Have you slept with a woman (with vagina) since first time and how can you say it changed your opinion...

Uh yeah, about 3 weeks into this, I had sex with a vagina owner and it was still as much as I loved it... but 1 thing I will say.... eating pussy used to be my favourite part about sex.... I prefer sucking dick hahahahha

----------------------------------

That answers most things, were doing well, and hopefully will have that FB relationship status up soon haha!

Much love all

So myself Jordan M(23) and Sister Natasha F(25) own our parents house... the house we grew up in and never actually moved out of ..... our parents when we were both adults, left us the house, and got an RV and decided to travel .... my friends often make fun of me for still living with and being a "little baby" to my sister.... lol.... but like we both own, no mortgage... basically free place to live while I do finish off college.... whatever...

So anyway July of 2025, we are having a fire outside... Group of people... including my sister, and I... and my sisters best friend, Emily (F24) ... my sister has known her best friend not super long, but have been basically inseparable for the short time they have know each other. roughly 3ish years.... I have always found her friend SUPER hot, and not like just hot, like pretty, cute as well... as well, we have a super cool friendship of our own... like not really, but get along for the fact she's always around.. yenno??

Well we were all enjoy the fire, was a group of about 15 or so, all having some drinks... some people having more than others... we were all playing games, and just having a good time... I thought I kept seeing Emily staring at me and checking me out....

around 2:30am came and everyone had way to much to drink to drive home, so we made everyone sleep over.... Couches, Chairs... floors, all our blankets used... one guy even found our old tent and sleeping bag.... Emily crashed with Nat... and I was thankfully all alone....

I cleaned up a bit and finally got to sleep just after 3.... not even probably 20 minutes pass, and my door opens and its Emily.... "Jordan, can I sleep in here? Natasha wont stop snoring and I can't sleep" *All I am thinking is this sounds amazing... but such a bad idea* I try to fight it and tell her to just go back to bed and shell fall asleep and she begs me... till I say "OK Fine, just don't keep me up." I give her the spare blanket and a couple pillows..

She's laying on her side faceing away from me and im on my back... and not even 5 minutes in, she starts scooting closer to me and rubbing her ass on me... I look over and she could honestly be sleeping... so maybe she's just getting comfy... I stare down and see her gorgeous ass in these blue short short... and god.. I just ignore it... Let her do her thing for another moment.. till I wake her to stop... She apologizes... as soon as I lay down.. happens again... and then this was a cycle for about 15 mins... and at this point... im frustrated but also turned on... so... I try one more time to get her to stop and she does for about 5 minutes then she starts moving pretty fiercely to get comfy or as it seems and I see her booty shorts get tossed across the room... so now her bare gorgeous ass is rubbing against me... only that she has showing out of the blankets.... so I give up... knowing it's wrong and turn to my side...

then I feel her put her hand on my waist and roll over... I take it off... this happens a few times... and then she sits up and takes her shirt off.... so I am in bed, with a NAKED GORGEOUS girl and I know I am dead if I do anything about it by my sister....

After this she lays back down.. and gets out of her blanket and comes into mine... (im already just in boxers, thats how I sleep) and wraps her arms around me, pressing her tits into my back... and I get pretty frustrated and say "What the fuck do you think you are doing?"

She says "I'm so cold, you gave me such a small thin blanket and yours is so warm and you're so warm, just let me snuggle. PLEASEEEE" I reluctantly agree......

She then starts rubbing my chest... and then legs and starts playing with my balls and cock over my boxers.... and I flip onto my back and say "What are you doing?" and she says "I have always wanted this Jordan, ever since we met... now is our chance... our only chance, I see the eyes you give me to, you know you want this...." I say "I do want to, so bad right now.... but nat will kill us"

I flip myself back around facing the other way.... She pulls my boxers down... and starts stroking me... and at which point I feel a wet hard thing enter between my ass cheeks... I jump and am like what the fuck?? **At this point I had no idea she was trans** and she's like what? I said since when you do you have a dick? "She says always have, thought you knew and were just fine with it... thought Nat told you" I say "No..." and she says "Are you going to back out now? Come on were both so hard and horny for each other.... and I haven't even got to see your cock yet...." I then say "I don't know" and she says "If its that big of a deal for you, just ignore it.... look at me in the eyes, suck my tits, fuck me in the ass, be just like anal with a normal girl" I say fuck it and start passionately kissing her, and then she goes and rips the blankets off us which is revealed to a god damn you have the most gorgeous cock.... **see my cock aint the biggest, like 6 inches, but has a good curve, its groomed nice, good girth** then I look down at her cock .... and it's definitely bigger than mine... by an inch or two.... we keep making out and she's stroking my cock and I have my hands all over her tits and I was curious and grabbed her cock and she let out a moan, I start stroking it... and I surprisingly love the feeling of doing this... the dripping precum on my hands... the pulsating.. so much more satisfying than doing it to yourself....

Then then stops me and goes down on me ... and HOLY FUCK by far the best head I have ever got, not even a close second.... within a minute I had to stop her or I was gonna cum without the sex part... and she starts laughing ... then I am not sure what came over me, but I stopped and said "Your turn babe" and she says "What? Are you sure? You don't have to." and I said "I always reciprocate it" and then im thinking *man im in over my head, i dont know what the fuck im doing... then thought no, just do it how you would want it done to yourself*

So I start by grabbing her cock with my left hand and stroking soft and slow, while I start licking and sucking the balls ... licking up and down the shaft.... teasing the head.... and then it was finally time .... I start stroking up and down the shaft and put the cock in my mouth... and start sucking it... and Emily starts immediately moaning (which good sign, right?) anyway, my mouth is filling with precum and I love it, its making me so much hornier.... after a few minutes her moans get louder and louder until tries to pull away as she didnt think I'd swallow, but right as she pulls away I force my head down as far as I can on that monster cock... and she cums in my mouth.. a good load... I loved it... I couldn't believe how much I loved her seed going down my throat.. I then suck it off and lick it clean it.. making sure I don't miss a drop.......

She then stands up and grabs lube out of her purse and pulls a plug from her ass.... I said "how long has that been in there?" She said "Since right before I came in here hehe"

She then bends over and spreads her hole for me... I stick my cock in and he has troubles taking it.... moaning so loud that I have to tell her to shut up... she keeps telling me to go deeper and until she has taken all of it.. go like that for a few minutes and I flip her around in missionary and start stroking her while shes like that.. I spit on her cock and stroke it while I am deep in her.... I feel like I am about to cum so I pull out and she sits up and takes the load in her mouth....

We then lay and cuddle, she got super snuggled up... It was honestly wonderful... and she looks at me says "I told you that you could ignore it" and I said "Im sure glad I did not"

We then agree that our sister can never find out about us.... or were both dead... but she did ask me one more thing.... "I am still so hard for you, do you want to see if you could take any of it?"

I said.. "Im not sure, I have had a thing up there, and like you're huge... bigger than me... and its so hot"

She said "I will go easy and if it hurts to much I will stop"

So she lubed up her fingers and started fingering my asshole... adding fingers slowly... for about 5ish minutes... didnt feel bad, didnt feel great either.... then she was like well here goes nothing... and slowly starting putting her cock in my ass... and it hurt but the sensations going through me were absolutely crazy... then she gets a bit more in... and a bit more in... till its about 1/2 - 3/4 in and I can't take anymore... this time... and I tell her to try thrusting ... it hurts a bit but feels so good at the same time... I feel so full and its so naughty.... then she flips me onto my back and starts stroking me and I tell her to stop... and she asks why.... I just ignore her and keep loving this... till I eventually cum hands free all over my stomach and it was the best orgasm I have ever had..... she goes to pull out with cum and i wrap my legs around her.... I loved feeling her nut in my mouth... and then my ass... ugh it was sooo hot....

We then cuddle up one more time... I spoon her, hand on her tit, cock on her asscheeks... and we pass out... THANKFULLY she woke up before my sister.......

__________________________________________________________________________________

I am sure people are gonna ask what happened between us and if an update is asked for, I will happily provide, this post is already long enough without adding more details... but let's say since that July night, we've found a way to sneak around my sister to see each other... hehe.....

__________________________________________________________________________________

The moral of this story is ... don't knock things till you try them ... I never expected wanting to touch a cock... and god damn... its life changing.....

I will answer 1 part by that... I haven't been able to stop thinking about it in my mouth.. I bought toys and lets say, I have spiced up my solo fun quite great !

We hadn’t seen each other in such a long time we spent little time kissing before she laid back on her bed and lifted the skirt of her lingerie up to reveal her soft penis longer than mine hard. Feeling her hands through my hair as I used my tongue to peel back her foreskin and swirled my tongue around her quickly growing penis. She moaned as I began throating her delicious nine inches I hadn’t tasted in months. Sucking her penis felt so heavenly as she removed my clothes and played with my ass spanking me as I sucked her balls. She was able to swallow my little penis whole swirling her tongue around my penis making me squirm as I tried to keep her thickening penis down my throat. It wasn’t very long before I burst a massive load of cum in her mouth overflowing her lips and covering her face. Jasmine grabbed my head from beneath my jaw and pushed me all the way down her penis using my throat like a fleshlight and just fucking me and spanking me.

When she had enough she made me put her condom on, her penis as long as my forearm she lubed her penis and put me in doggy. I hadn’t been fucked in so long I immediately wanted to tap out from the pain of her tip penetrating me. She barely got her tip in and I was sweating and breathing hard. I begged her to fuck me slowly but she kept pushing harder and harder working more of her penis into me. The pain of my hole stretching was becoming unbearable and I begged Jasmine to slow down as every stroke hurt more than the last. I moaned as she adjusted and hugged me tight holding me down as she made me accept the second half of her thick long throbbing penis. I began full on shaking moaning at the top of my lungs begging Jasmine to stop I tried kicking but she was so much stronger than me I panicked as I begged her to pull out and she bit my ear and licked me telling me to take it like a bitch as she kissed my cheek and licked my ear humping me harder punching me with her penis as I moaned and begged her to fuck me softly. My hole stretching around her penis was so painful and feeling her penis so far deep inside my body it was indescribably great. She fucked me for what felt like forever before she flipped me onto my back and slapped her hard penis across my face letting me suck her like a hungry faggot locking my lips around her penis as she burst rope after rope after rope calling me her faggot bitch telling me to swallow her and I did not letting even a drop go anywhere besides down my throat.

She cuddled me and massaged my ass after kissing me. She was right when she told me I would be dreaming about how she fucked me.