r/tsgonewildstories

A couple of months ago, I unexpectedly received a proposal for a work trip to Bangkok. I pretended to be hesitant, but at the same time, I was already thinking about how amazing the trip would be.

​The first two days were spent checking apps, talking with a couple of ladyboys, and working full-time. But then, it clicked. I came back from work feeling drained. One girl was very good-looking, but it was already around midnight. She wasn't too far away, so I proposed that I could jump over to give her a blowjob, as I was already very tired. She promised to help me get back on my feet, which sounded promising.

​After getting myself ready, I ordered an Uber scooter and went to her. We met in front of her building. She was very tall—around my height, close to 6 feet—and in a really casual outfit. She hugged me, and we entered the building and headed up to her apartment. The lights were dimmed, and some dance music was playing in the background. She jumped onto the bed instantly and invited me over by tapping the spot next to her. We started kissing and touching each other slowly, still fully dressed. Soon enough, she told me to undress while she prepared a pipe for us. In no time, I was kneeling in just a pair of lacy jockstraps, massaging her feet while taking a smoke from time to time. When she finally started undressing herself, I ran my mouth and tongue over every revealed part of her body.

​We got back onto the bed, and she turned on some porn on the TV while I finally reached my destination. I started slowly kissing her inner thighs, the area around her very nice, almost straight, uncut cock, and moved slowly toward her balls. I gave each one a kiss, licked them, and successfully fit both into my mouth, playing with them a little inside. She was moaning softly while holding my head and stroking my hair. Then, she grabbed my head, pulled me closer, and started kissing me again. Our tongues gently fought as our mouths locked together. While still holding my head, she pushed me back down again and directed me to her shaft. I licked it slowly from bottom to top, swirling my tongue around the head, but her firm grip directed me to take it fully into my mouth. Gladly, she wasn't too big—around 6.5 inches, I think—so I was able to take it deep. She held me like that for a moment, moaning like crazy, then started moving my head up and down. When she let go, I caught my breath while stroking her shaft, but the mood had kicked in and I didn't want to make her wait too long. I put her back in, sucking firmly but gently at the same time, as I didn't want it to end too soon. Then, she asked me to change positions so she could play with my butt at the same time.

​I turned around into a half-doggy position and got back to work. She rubbed my cheeks, played with my butt a little, and gave me a couple of spanks. Whenever I smoke anything, I stay completely limp, so she started rubbing my dick and balls with her open hand while her thumb made circles around my hole. The feeling was amazing, and it became hard to fully focus on my only job. When she pressed her thumb deeper, I let out a long moan and kept stroking her while breathing heavily against her sack. She stopped rubbing me and slid a middle finger in. When it worked perfectly loose, she added a second. And a third. I was blissful and incredibly close to orgasm, still catching my breath at her crotch, trying to at least give the head a lick from time to time.

​"Can I fuck you?" she asked. I was only able to nod with a soft, "Yes." ​"Make it wet." She pulled her fingers out and led me back to sucking and deep-throating her. A moment later, she pushed me further onto the bed, kneeled right behind me, and started rimming me. Her tongue felt amazing—from long licks and circles to pushing as deep as possible inside me. Then, I felt it coming. She straightened up and rubbed her cock around my hole. I was on the edge. I wanted to feel her inside me so badly that I started pushing myself toward her, trying to make it slip in. I even started rubbing myself to bring myself even deeper into a slutty, submissive mode.

Then, she aimed and, without any hesitation, pushed herself all the way in. I was blissful. The warmth that rushed through my body was so intense that I spurted a little. She found her pace and rammed me rhythmically. I was moaning like crazy, trying to force myself into the sheets so I wouldn't make too much noise. She held me firmly, pressing into me one thrust after another. I completely lost myself in it as she pushed harder and harder.

​She told me to turn around into missionary so she could continue. I bit my lips to stay as silent as possible, covering my mouth with one hand while still rubbing myself with the other. She was like a machine, pressing my P-spot with every thrust until I almost passed out, cumming just from her work and from rubbing my junk like a clit. She slapped me softly so I regained contact with reality while she was still pounding me hard. I was completely melted. She started collecting all my cum, feeding it to me and saying, "You'll get a reward soon." In no time, after I cleaned her fingers perfectly, she sat on my chest and came all over my mouth and face. She lay down by my side, catching her breath, then reached over to me and started scooping everything into my mouth. When I swallowed, she kissed me passionately one more time.

​We lay there for quite some time, trying to pull ourselves together. Both of us took a shower, I gave her and her cock a kiss, and I went back to my hotel. It was already after sunrise, but I had no idea what time it was...

ok so i did a thing at a party this weekend and i kind of need to tell someone or it's just gonna live in my head forever

there was this guy, friend of a friend, we'd been doing the thing all night where you keep ending up in the same three feet of kitchen. eventually he asked if i wanted to help him find his jacket, which is the worst line ever and i said yes immediately because apparently i have no standards when someone's mouth looks like that.

so we're in the back bedroom, coats piled up on the bed like a mountain, and he's got me against the door kissing me before i even pretend to look for a jacket. then his hand goes down and he stops. that little pause. i felt him figure it out. i pulled back to watch his face do the whole thing, the surprise, the recalculating, and then he ju

i was not ready for how fast he went from confused to enthusiastic. hand over my mouth the whole time because people kept opening the door looking for their stuff and i had to act normal with a stranger's mouth on me.

someone literally asked if we'd seen a green tote bag. i said no. i was lying. i could not have located a tote bag to save my life right then.

anyway i finished embarrassingly quick and we never did find his jacket.

I had an experience with a TS escort that went totally unexpected and awakened something in me.

She's a well reviewed mixed Asian TS in Canada. She's Korean, Filipina and Spanish mix, with that smoking hot exotic look that some JAV stars have. Extremely feminine, a thicc body, skinny waist, long dark hair down the length of her back, a few tattoos. Total Asian baddy and exactly my type.

Typically with girls like her, I'd be be 100% top. I like to go with the flow, so didn't communicate any expectations with her, just a couple of flirty texts and some pics, which she seemed enthusiastic about by fit and well groomed body.

I went to see her expecting to top, but as I'd soon find out she had her own idea for the session. As soon as I got through the door, she had her hands squeezing my ass and even running a finger between my cheeks to feel around the rim of my ass while we made out. Even in the shower, she snuck in to get a few more peeks at my ass and give me a few playful smacks.

I must have been the first fuck of the day, because this girl was HORNY. We got to the bed and she straddled my face, making me deep throat her cock and suck her balls, while she rubbed around my ass with spit lubed fingers. Having me gag on her balls made her go feral, she was leaking pre-cum and whispering in my ear to let her fuck me. She never put on a condom as she got into the spooning position behind me, I was panicking a bit as I had never been barebacked before. She reassured me "relax baby, let me tease your ass first". I was unsure what she had planned for me as she pulled my head back for a deep kiss while I felt her rock hard cock rubbing around my ass. She was thigh fucking me, getting extremely turned on and breathing into my mouth with her tongue stuck into my mouth; my cheeks were getting slick with precum. She was desperate for something more and I could feel her shift to thrust directly against my hole, and after a few prods her uncut cock was starting to slip inside me. Her foreskin and precut just allowing just allowing the head to slip inside my ass and not much of he shaft.

After a few minutes of this, she seemed to gain some self composure, gritted her teeth and grabbed a condom, ripped the wrapper with her teeth and quickly rolled it onto he rock hard cock. I felt a rush of relief that I wasn't gonna get fucked bare, but also a bit of disappointment as she urgently put me on my back, lubed up my ass and pinned my knees up, thrusting balls deep in a single stroke. she was jack hammering my ass, but anyone who's fucked bareback before knows it feels night and day to fuck with a condom. I could tell she was just not feeling it with the cover and after switching a few positions between frustrated thrusting, she couldn't take it anymore. She pulled out, and while staring into my eyes without a word pulled the condom off by the tip making a crisp snap.

She leaned in, kissed me deeply and me "put it inside baby", I couldn't say no at this point and I grabbed hold of her hard cock and guided it inside my ass. It felt like a dam burst inside her and she started talking really dirty to me, like "I love feeling you skin to skin"and "I'm going to breed you baby". She ended up on top of my in prone bone, alternating between deeply french kissing me and licking inside my ear, which felt extremely erotic and over stimulating. I could tell her orgasm was building as she was pressing into me as hard as she could and I could feel her pulse and throb for almost a minute as she came hard inside me. She came so hard she actually fell asleep while on top of me, I laid there in a stunned state in disbelief of what just happened, feeling our sweaty bodies pressed together and her tits my back, her cock slowly losing hardness inside me while she quietly snored with her head next to mine. After she woke up, she let me fuck her bareback and I came inside her ass even though she told me not. She was a bit mad but said it was fair for me to get my payback, but she had to wash my cum out of her ass before seeing the next client. We had gone over time so much that her phone was blowing up, so I didn't have time to shower after. During the whole drive home, I could feel how slick my ass was with her cum leaking out.

I had a had a handful of other TS escort encounters that ended in bareback, both topping and bottoming.

Since 2014 I have had multiple experiences with TS girls (+25), solely as a top. In both 2016 & 2022 I had the opportunity to try being bottom when I was with two versatile girls but passed as I did not like the idea at the time.

After the 2022 experience was passed up, I have probably thought about it every week and have grown to love TS porn (thanks Reddit!). Unfortunately in the experiences I have had since then, all the women have been complete bottoms or have not been able to maintain an erection.

Until last week.

I matched with a Cuban lady on a swingers site, who was Trans and through the communication I believed she was only a bottom. Needing some action badly due to multiple days of hangover horn, we agreed to meet and within 90 minutes of matching I was at her door.

After a glass of wine and some hand action in which she placed a cock ring on both of us, she ushered me to the bedroom before saying in broken English “Me first. Stamina. Si?” Shocked as I was expecting only to top I stammered and agreed to “try” as it was my first time outside of pegging and asked her to please be gentle.

With some slow very lubricated fingering and passionate kissing I was in ecstasy as I could feel her rock hard cock digging into my balls. She repositioned and started to enter me once she decided I was open enough, and slowly inch by inch she slid in. Taking what felt like an eternity I was in a trance and breathing deep, only to snap out of both when I finally felt her balls pressing against my own.

No thrusting to begin with only grinding and more passionate kissing, I felt incredible inside but noticed I had gone totally soft even though I was incredibly aroused and even with the cock ring. When she noticed this she changed position lifting my legs and began to thrust, slowly and only half way in and out. After about 5x mins I began to get an erection again and she stood me up off the bed, standing side on against her dresser so we could both watch in the mirror.

My erection was now fully throbbing as she spread my cheeks and slid back into me. I was so horny at this moment I could feel an orgasm building even though she hadn’t touched my cock since the foreplay before sex. She stood there speaking in Spanish in my ear as she thrust into me, getting harder with each one. Pulling out almost all the way slowly, then thrusting her full length hard then holding it for 3-5 seconds. On the hold I could feel her pulsing against my prostate and started to leak a little pre-cum.

A couple of minutes of this and I knew I was about to burst, and having had hands free orgasms during pegging I knew the sensation. I asked her to stop as I was about to cum… which had the opposite effect. She made a guttural noise as she started to fuck me harder and faster… I don’t even think I lasted 90 seconds.

I could see in the mirror my rock hard cock spurting like a burst fire hose, cum spraying everywhere as she had an almost evil grin whilst still pumping away. When I started to recover from the brain melting orgasm I pulled away and told her I needed a break then would fuck her as soon as I was ready.

“No. No finish. Stamina, si?” And pushed me face first onto the bed. Quick as a flash she mounted me and I can’t describe fully how hard she fucked me on all fours. She fucked me like how I like to fuck… so that was an eye opener.

10 minutes of doggy style and 5 minutes of ploughing me into the mattress lying prone, I was just enduring it and mentally realising she’s was treating me like how I’ve treated some people during sex, just something to cum in.

This realisation weirdly got me hornier again and my half flaccid cock began to rise again. As her breathing began to labour, she pulled out and lay on her back, quickly pulling my into position to straddle her.

“You work. Sit”

I was so embarrassed as I had never imagined being on top, but found myself squatting on her dick and attempting to ride (very poorly). Thinking this may also be a good time to recover as I could be in control was absolutely not the case. From this position, she grabbed my hips and thrust up into me with great vigour hitting what felt like even deeper than before.

I seen the clock and realised she had been fucking me relentlessly for 40 minutes at this point which again strangely got me even more aroused as I was trying to bounce on her her dick and watching my own erection get back to full mast.

When she seen I was fully erect again, with sweat pouring from her brow and body, she flipped me over without even removing herself an inch from my ass. With one swift motion she held one leg over her shoulder and finally grabbed my dick, starting to stroke furiously as she pumped into me.

Looking me in the eye she said “Si, Si, now!”

Knowing exactly what was happening as her thrusts became harder and more erratic, her jerking sent me over the edge into a 2nd orgasm as she started buck and push even deeper into me, unloading her cum all the way inside as she let out a squeal/scream of passionate delight.

I could not believe it at the time and also retelling it now, still cannot believe it. Lying there giggling together, she got back up and brought through the wine. We waited about 30 mins and she began to finger and stroke herself, showing me everything along the way.

As I regained an erection she bent over in front of me and spread her ass exposing her open hole, glistening with lube from her fingering. I took this as the invitation to enter and knowing fine well that after 2x orgasms I would need to really work hard to get over the line. Plus, I wanted to give some payback for the drilling she gave me and didn’t want to be outdone!

I really went to town on her, pumping fully stroke basically right from the beginning, hammering her soaking hole which felt amazingly both a snug fit but loose enough to really get into. She leaned back on her knees and turned her head to kiss me as we watched in the mirror. I started to jerk her and she asked me to slower… I remembered she did not offer me the same kindness so timed my thrusting in with the down stroke of the jerk and kept up a fast pace. Within about a minute she started to buck again and pushing back onto me she started to cum.

As I was thrusting into her I could feel her cum start to leak from my ass down the back of my balls and this sent my caveman horn brain into overdrive, releasing her cock and grabbing both hips really driving my length into her balls deep. Pushing her down in the mattress I held her firmly in position and told her I would not stop until I cum. Pounding and pounding, hearing her whimper i eventually felt the sweet release of orgasm and emptied myself into her ass.

This was 11x days ago… and I haven’t stopped masturbating or thinking about it since.

I (MtF 23) started E about 6 months ago. I knew going into it that there were going to be changes to the way my mind and body function sexually. But weirdly enough, i haven't experienced the decreased libido. What I have experienced is the shorter erections, which have resulted in me being able to edge for hours at a time for weeks without cumming and it has been really really intoxicating.

But last night i was scrolling reddit on my main, and I see a post in a local NSFW subreddit of this cis guy and his dick. And I could not scroll away. It was so long and hard and it had cum dripping from the tip and my mind went blank. And i scrolled through the other photos and i felt my entire body need it. I had been edging for so long and suddenly I could feel my girldick getting hard. Like hard hard. Like after some teasing it started drooling hard. When I saw my finger I thought of his cock and instantly sucked the cum from it. I thought about how i wanted it in my mouth, in my ass, in my pussy I didn't even have. I want it to release inside of me and fill me up. I thought about how badly I wanted to be bred.

After my girldick settled back down enough for me to type, I commented underneath about what had happened and how badly I wanted his dick.

He messages me.

I get ready.

But on cute dress.

Underwear.

Take off underwear.

I get onto the bus, my bare ass essentially in the seat with my lap decently covered. And this older woman sits next to me and tells me how cute my makeup and outfit are. And I had to like hold my composure, because between being stuck in horny brain, in public, this gorgeous woman was telling me how cute I was and my new hormones make me way way more sensitive to validation like that and I just felt so girly and slutty and when my stop came I got off, walked a few blocks with absolutely no thoughts in my head. It wasn't until I got in that i really thought about the math here.

I am walking into a strange cis mans house.

I have never hooked up with a cis man before.

I do not know if he looked at my profile to see i was trans.

I could seriously be in danger.

I have never been so horny. Not even hard just, HORNY.

I text him that i am here and he lets me in. He tells me how much he likes my makeup and dress. And as he is leading me in i go, "hey, i should be up front and tell you I'm trans"

"I don't care"

He says it so dismissively putting his hand on my back and guiding me in. He leads me into his livingroom and sits down on his couch, takes his pants off, and I see it in person.

Its soft, but still as big and thick. I collapsed to my knees and started kissing and licking it. It started to get harder and harder, which excited me more and more. And i kept trying to suck it but I wasn't really good. I tried stroking and licking and kissing for a while more but he finally asked me if he could fuck me.

I explain that I haven't done a lot of anal stuff, mostly with my dildos which i have one about his size i almost never use. He asks me if I have ever tried poppers. And I shake my head. I know what they are but never tried them before. He offered me one and I inhaled it and my head was spinning immediately. He lead me to his room and everything along the way felt so wobbly and high. I knew it was used to make your muscles relax, but i didn't realize how intense and high it would make me feel. When we get to the room he offers it to me again and i take another hit and hold it longer. This time i fall onto his bed and start laughing uncontrollably for a bit. He flipped me on my back and lubed my hole and his dick. When it went in I came out of the high. He was slow, pressing a little deeper each time. It would hurt at first, but then finally he worked the entire thing in. Another hit from the bottle. He starts actually thrusting into me harder and more rythmicly. My body was on fire, and all i could think about was being full of cum. How i wanted my fantasy womb dripping with cum. I wanted it to breed me.

When he finally came inside me, i felt it as he pulled himself out. He gave me a second to calm down. He called me a lyft, I have him send it to an address that I don't live at anymore (because NOW in being safe) and take the bus home from there.

Its been a few days. My body isn't as sore as it was after that. My girlfriend and her boyfriend have been teasing me relentlessly for being so "I hate cis men" "they are useless. I don't even want to sleep with them". Though, last night me and her were out drinking and she told me that she wants me to fuck her boyfriend with her. I haven't ever really hung out with him that much, but the idea of us doing it together to him. Just cute girlfriends sharing. Normal partner stuff right? I will let you all know what (if anything) happens

Hey all thought I'd share a fun story with you all!

I was in my early 20's and had just moved to Texas for work - lonely, overworked and very horny. Tinder was proving to be fun, and I'd been hooking up here and there

One day in the middle of work I matched with B! Cute black girl, didn't have too many photos though. After some light chatting and flirting she told me she was trans. I was curious at the time, had seen some porn and well, I was horny. The next bit that came out though was she preferred to top! My ex had pegged me a few times before - I had enjoyed it a lot. When I told her that I had some experience it went from super flirty to borderline sexually aggressive - now she was super into me, and excited that I'd never had a real dick before

As the day went on she messaged me several times, asking when I'd be free. I was tired after a day of work, but this aggressive interest along with my curiosity got the better of me - I finally said I'd head over to her place that night. I didn't even have any toys to warm up with, my ex having used some plugs before she'd peg me so I just showered and got as ready as I could

She sent me the address to her place - a dorm at a nearby college. I was told that I'd have to climb through a window and sneak in, both security and having roommates meant that we'd have to keep things quiet. As I was getting closer and sneaking in I felt super aroused and nervous - what if this was some fucked up prank?

Luckily B met me at the window and let me in - she had the lights low, whispered as I came in. She was wearing the same dress as one of her pictures. I smiled and kissed her, we shared a little cute moment

However after that, she grabbed my head and pushed me down to my knees. She pulled her cock out from under her dress and I saw why she was so excited to find someone who was experienced - her cock was _fucking_ massive. At least 8/9 inches, and thick. Having never seen a hard cock at this angle and this close up too, I wasn't sure I could handle it

I sucked her a bit, taking her whispered coaching. I tried copying what I'd seen in porn, but it felt like I couldn't fit it as easily as those girls fit those massive porn cocks down their throats. Teasing her massive head, tasting her sweet precum though, I got through that first wave of nervousness. After a few minutes she pulled me back and onto the bed, pulling my shorts down. We 69'd a bit, I felt her heavy balls on my nose while she easily sucked my cock.

First her finger rubbed my asshole, then her tongue went down. I moaned through her cock. Suddenly her tongue moved down and she was eating me out, faster and deeper. I'd never had someone eat me out as eagerly before and I was moaning, muffled by her fat cock down my throat

She flipped me over, I was putty in her hands at this point as she spread my cheeks and tongue fucked me. "Can I fuck you baby?" she asked, suddenly I was back to reality. Thinking of that massive cock, there was no way it was going in me. "I'm not sure.... it's too much...." "Can I just rub the tip on your hole? It'll feel so good for me?" I was torn between letting her but my cock was still throbbing

"Ok, just...be gentle please..." Her thick cockhead was such a change from her tongue, warm but I realized how fucking hard she was, how desperate to be in me. She lay on top of me, her warmth pressing down. One hand snaked around and covered my mouth. Fuck, I knew what was going to happen I fell for the oldest trick in the book 'just the tip'

Her cock pressed into me more, I felt like I was getting split in half - her hand clamped around my mouth, the other around my throat as my ass got violated

"Shhhh baby you're doing so good it's in doesn't it feel good" While her cock felt like it was tearing me open it did feel so fucking great, my own cock rubbing against the sheets. She started fucking me then, nice and gentle but I felt her cock moving in and out, hitting my spot

Between the ass eating, the pressure on my cock and hers in my ass I came in like two minutes. Now for those not as familiar with butt stuff, sometimes that post nut clarity hits _hard_ and in this case it was a bitch - here I was pinned down with a huge cock in my ass. She took this moment, feeling my ass clench and quiver painting her sheets with cum to speed up. "Fuck fuck fuck please please stop" i tried to say through her hands but she just whispered "I'm so close baby just let me finish" - for a second I thought about her cumming raw in my ass and wanted to let her but I thought of an alternative 'just cum in my mouth, please give my ass a break'

After a few more pumps I felt her hand grab my hair and a sense of relief and emptyness as her cock pulled out - only to be replaced by her pulling me back onto my knees, her cock pressed against my lips. I started sucking it, warm from my ass tasting the lube, humiliated to be doing ass to mouth when she came, filling my mouth with her cum

I swallowed it all gagging on the taste. Thankfully she handed me some water, giving me a second to regain my composure

"Soo baby I have class tomorrow, I need you to head out" barely after I recovered and I was getting kicked out, fuck. "You did so good baby, we'll have to meet again..." as I climbed out the window she grabbed my ass feeling me up

We'd hook up many times that summer, but that first encounter set the tone for what was to follow.....

So on my last post, I mentioned that during my time in Thailand, I also hooked up with a 50 year old ladyboy. Some people messaged asking for the story, so here it goes.

After a boozey 4 weeks across the party islands in south Thailand, I decided to head east. I arrived on a smaller island, much more chilled than the others, planning on a break from the drink, sex and partying. Going with the flow, I didn’t book anywhere to stay, and after two hostels told me they were fully booked for the week, I headed to a guest house on the beach. This is where I met Noi, a 50 year old woman who rented out a room in her small house.

After speaking with her, we agreed a price for the week, considerably cheaper than where I’d recently been staying. She quickly showed me around the place before showing me my room, surprisingly nice, especially for the price. It was late so we said good night as I headed for a shower and then bed.

Waking up late, clearly needing to catch up on sleep, I made my way to the kitchen. Noi wasn’t around, so I helped myself to coffee and bread, taking it out to beach. Still half asleep, I had my breakfast out in the sun, looking out at the waves in the distance. It wasn’t long until Noi came back, carrying two shopping bags. It was the first time I’d fully checked her out, she was small, a little bit curvy, short jet black hair, with piercings in both ears. She was wearing sunglasses and a sundress, showing off her great figure. It was impossible to believe she was 50, looking 35 at the most. Topless and in my swimming shorts I greeted her, helping her with the shopping.

In the kitchen we talked for hours, she’d told me about her life, that her ex husband moved back to Bangkok years ago. Although she was comfortable telling me, I decided not to ask any more questions about him. I told her all about my travels, and all the places I’d been to in Thailand. I’d explained that I wanted a chilled week, she told me I’d come to the right place for that. The more we chatted, the more comfortable we were with eachtother, even having conversations about my ex relationships. She asked if I wanted to anything the next day, and that she could take me round the island on her moped, which I agreed to.

The next day came, Noi woke me up, saying she’d made breakfast. After eating together, I climbed on the back of her moped, my arms around her, holding on for my life as she sped around. 15 minutes passed before she parked up on the side of the road, she led me through some trees. Quickly soil became sand, a small cove hidden on the island. It was like we had our own private beach, she lay down the towels as I headed into the water. It was bliss, it was the first time I’d heard nothing in a long time. Noi joined me in there, both treading water as we talked. My eyes were glued to hers, her dark wet hair made her brown eyes shine even more. We both couldn’t help but smile at each other, each sentence flirtier than the last. I held myself back from kissing her, worried I was reading it all wrong.

We both swam back to shore, lying on the towels on the hot sand. Only a foot or two separated us. Being English, I had to rub suncream on myself, managing to reach most parts of my body. As I tried to reach my back, Noi sat up and helped. It had gone exactly as I’d hoped. I lay on my front as she rubbed suncream into my back, both of us silent as she did so. She complimented my physique, which had deteriorated greatly during my travels. I turned back around, Noi stayed kneeled up next to me. I told her I found her very attractive, refusing to believe her age. A nervous smile broke, unable to look at me as I complimented her back. My hand went to hold hers, hoping to get her eyes back on me, which they did. I sat up, smiling at her, glancing from her eyes down to her lips, wanting to her to make the first move. The tension was too much for us both, our lips touching, and then passionately kissing eachtoher.

We kissed for a while on the beach before she said we should head back. As I climbed back on her moped, I held onto her in a different way, my hands exploring her body. Her tits were perky and solid, clearly fake, and from past experiences I knew what that could mean. It was something I’d already questioned when we were in the water, if she was a ladyboy or a woman, neither bothered me. Half tempted to find out straight away, I resisted the temptation to feel, waiting to get back instead.

Arriving at the house, I asked her if she wanted to go out for some drinks and food. She told me she knew some great spots and would be ready in an hour. I showered and got changed, waiting in my room for Noi. She knocked on my door, I walked over to open it and there she stood, looking amazing. She wore a green dress, her hair tied back with light make up on her face. I, on the other hand, was underdressed, not having anything in my bag to even come close to what she was wearing. We walked to the first bar, the whole time I checked her out, fully attracted to what I was seeing.

A few drinks had passed, we sat out a beach bar together, both a little bit tipsy and fully comfortable with each other. The conversation flowed nicely, with some leg touching under the table. I was eager to get back to the house, wanting to carry on from where left it at the beach. It turned out we didn’t need to go back to house, because after a few more drinks were kissing each other at the bar, her hand making her way up my shorts. She brushed over my erect dick, smiling, happy from what she had felt. Still at the bar, she kissed my neck and whispered in my ear that she wanted to go back.

We only made it to the kitchen at her house before we were all over each other again, picking her up with her legs wrapped around me. My mouth went down from her lips to her neck, then lower to her breasts. She moved the strapping off of her shoulder so her tits were now uncovered, sucking on them as I grabbed her ass. I lay her down on the kitchen table, pulling off the dress so she was only wearing her panties. I kissed down her body before reaching her black silk panties.

Unlike other ladyboys, she didn’t warn me or tell me, just let me find out myself. If I’m being honest, I’d felt her dick when she was up on me, and it was clearly erect when I took her dress off, leaving a big crease in her panties. Immediately I took off her panties and began to suck her, she was bigger and thicker than anyone I’d been with, and she’d clearly shaved whilst she got ready beforehand. Her pre cum tasted great, her moans whilst I sucked the tip made me hornier and hornier. I tried to take her whole in my mouth but I couldn’t. Off my knees, I stood up and brought her to the edge of the table, where I took off my shorts and flopped out my fully erect penis. It was clear she’d done this many times, as I received the best blowjob that I’d ever had. We spent the rest of the night jerking and sucking each other, Noi came three times whilst she made me cum four times! I think we ended up actually sleeping at 6am, cuddled next to each other when we woke up.

We lay in bed talking, she’d asked me if I was bothered she was a ladyboy. I told her I wasn’t, and that she wasn’t the first I’d been with in Thailand. She told me it was obvious she wasn’t my first one by the way I didn’t react to her dick and the way I sucked it. The more we talked about the night before, the hornier I became, my dick hardening on her ass. She turned to me and smirked, kissing me as she stroked me, teasing my tip around her hole. She grabbed the lube from the side, putting a lot in her hand, covering my dick in it. We took our time putting it in, kissing more passionately with each inch that entered. I’ve had serious relationships before, but I’ve never had more intimate sex than what me and Noi had that morning, and for the rest of the week. It wasn’t rough and hard, it was slow, enjoying every second of it.

At the end of the week it was tough to say goodbye. She’d asked me to stay a few more days but I knew it was time for it to be over. That week with Noi was one of the best weeks I’ve had, and I haven’t been attracted to anybody as much as her since. We stopped speaking a year ago after she told me she’d started seeing a woman from the island.

So I used to visit Thailand quite a bit for work and this was one of my more memorable stories there.
When I was there I used to use an app (Beetalk and WeChat) to find locals around me who wanted to grab drinks or wanted a foreigner to play with. This particular time I matched with ladyboy from Malaysia who looked smoking hot, feminine face and a dr make body with all the right curves. I was instantly smitten and we were messaging on where to meet up. She finally asked me to go to her hotel in a very local place far away from tourist areas so I take a taxi and get to a dimly lit night market and with the address I have the taxi driver dropped me off in front of a restaurant. A little confused I started messaging again and found out the hotel was on top of the restaurant through a small side door.
I get to her room and there are two hot ladies, one on the bed and another just sitting in a chair both watching tv. I'm offered a beer which I gladly accept and told me that they were in Thailand for her friend to have genital reassignment surgery and we're staying at this cheap hotel while in recovery.
Not understanding why they're telling me this though interesting, the friend who I matched with then asked if I would help them test out her friend's new parts. I was interested but was honestly looking for a lady who had a cock. And they said they didn't want to go full out fucking but just wanted me to test it out a little bit.
Seeing my semi hard cock poke through my shorts and me not answering yet, the friend just tugs at my shorts and pulls out my cock straight into her mouth while the pre op lady just watching. Once I'm hard enough she gets on the bed and tells me to put it in. I wrap myself up and oh man, this is the tightest pussy I've felt since I was a teenager. The dr did a great job and it felt amazing. Unfortunately, after a few minutes of thrusting I guess their test was done and the friend got up, gave me a kiss and said thank you while leaving.
The girl I matched up with closed the door and said thanks, but it's her turn now.
I took her lingerie off and revealed a thick dark cock about 6in, the biggest ladyboy I've been with and couldn't slurp it up any faster than I did. The feeling of a warm cock in your mouth while feeling amazing silicone breasts is one of the best things out there. We traded some more oral and she got on all fours while looking back at me. Standing behind her about to mount her I decided I wanted to fuck her while holding her joystick so I flip her over and insert into her slowly until she was accustomed to me. I pick up my pace a little and watch her breasts bounce up and down and with her cock in my hands stroking her with each of my thrusts.
She starts closing her eyes, her breaths getting shorter and shorter, toes curling up then she starts moaning out she's cumming.
I see the first rope come out and then drop to the side of the bed so I could swallow the rest. After she finishes, I get back to position, kiss her with her own juices still in my mouth and get back thrusting. I quickly finish inside her while still making out and it was just bliss.
After getting dressed and having a smoke with her I leave and her friend is just chilling outside in the hallways, said thanks to me again and I take off into the night.
Just one of my many BKK stories.
Thanks for reading and let me know if you wanna hear more.
Typed on my phone: sorry for formatting.

So this is the first time I've ever bought a toy and holy shit, I can't believe it's taken me so long.

So anyway, yesterday I had a long drive home, about 5 hours. It's a trip I've done many times and know the road very well as I do it regularly.

Anyway as I was driving, I was like fuck it, I'm bored, I wonder what it would be like to use it while I'm driving to entertain me.

Holy shit, I've never had orgasim quite like that.

I placed it in my underwear and it turned out great because the panties held it in place.

I got it into position, set it on the lowest setting, started the car and began to drive.

It felt so fucking good. I slowly increased its intensity. As I was getting close to the top setting it became so fucking intense. I got it to the top setting and had to pull over because my orgasim was becoming uncontrollable.

I just sat there completely helpless with this stuck in my pants while shaking and losing complete control of my body. My whole body was shaking and I couldn't stop moaning.

It was one of the best organisms I've ever had in my life. I made sure not to touch it, I liked the feeling of being helpless and having no control.

I still can't believe I did it and it's a story I'll take to my grave but I wanted to share with all of you because holy fuck it was something.

When I was in Bangkok, I partied hard for a week, getting drunk every night, forgetting most things when I woke up. However on one of my last nights, something happened that I could never forget.

It was roughly 2am, I was done clubbing and wanted to head back to my hostel. Stumbling out onto khao San road, I was instantly surrounded by people. In the crowd, prostitutes grabbed me, trying to pull me towards them. Before I knew it I was on the side of the road, with three Thai women in front of me. The three of them negotiated prices in front of me, until one of them told me 400 Baht (less than £10)!

Drunkenly I nodded, and she spun around, grabbing my arm and taking me to a low quality apartment block, only 2 minutes from where we were. As she grabbed her keys from her bag to enter the block, I asked one question.

‘Are you a lady?’

She looked at me with a smirk, pulling my hand towards the crotch of her dress. I was met with a hard throbbing cock. It was something I was definitely curious about before going to Thailand, and I knew I was going to go through with it.

‘I know you like’ she said to me.

After giving her a quick kiss, we headed into the room. She lay me on the bed as she got herself ready in the bathroom. I quickly messaged my friend ‘about to fuck a ladyboy’, before putting my phone down as she came into the room. She’d taken off her summers dress, and instead was in black laced lingerie. Her tits looked great, and her whole body was soft to touch. She wasted no time, unbuckling my belt and moving down on me, my dick already erect from everything. She sucked good, not the best I’d had, but the thrill of it all made it feel amazing. Although the feeling was great, I was still curious to see what she was working with.

I pulled her hair to remove her mouth off my dick, bringing her back up to me to kiss. She straddled me as both our dicks rubbed together, with only her soft panties in between us.

‘Can I suck you?’ I asked her.

She giggled and nodded her head, the excitement in her eyes growing. She stood on the side of the bed, grabbing me by my neck and putting me on my knees. I kissed the outline of her dick through her panties until she eventually lowered them down. She was as thick as me, maybe an inch shorter, with some pubic hair above her shaft. As I opened her mouth I instantly tasted her pre cum, licking all of it up, loving each taste I got. She thrusted harder and harder until she was ready to cum, hesitant if I wanted her load.

‘I want to taste it’ I said looking up at her.

I sucked her hard and good after that, begging for her cum. Her moans were slutty and very loud until she unloaded into my mouth. It was way more than I’d anticipated, having to take my mouth off and let some go down my chest. She lay me back down, licked her cum off me and sucked me until I finished, with her also taking most of my load down her throat.

I told her after I’d finished that she was my first ladyboy, and tipped her extra for her service. After it I was desperate for more ladyboy action, actively only seeking it. The rest of my time in Thailand was filled with many more stories, even fucking a 50 year old ladyboy !

[25M] So recently there’s been something about TGirls that have been really turning me on. I’ve only been with women sexually. I like to please within those acts so I guess it’s the fact of getting them off/dominating? I was wondering how other people’s 1st experience fucking a TGirl went?

Did it feel wrong? Did you like it? Part of me feels wrong for being so attracted but it’s been on my mind..

Also if anyone knows any spots around Philly, New Jersey, for local spots please let me know!