r/transstoriesgonewild

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...

So background I’m a 25yo bi ish married male. I say bi ish because I’ve never really been attracted to men but I do feel attracted to their package. I married my wife right after high school, she’s definitely the more dominant in our relationship. I’ve always been self conscious about my package size but instead of reassuring me my wife liked to make it worse. At the beginning of our relationship it was strictly just between me and her, she would make jokes about my size and would even make me change into panties when we would hang out because I was “too small to fill out men’s underwear”. Her behavior caused me to grow a humiliation/degradation kink.

Once we got married her humiliation got more public. When we moved in together she replaced my whole underwear drawer with women’s underwear, some even matching hers, and she even gave me a little section in the closet with dresses and skirts and stuff to wear. She made sure every one of her friends and quite a bit of her family knew how small I was, some of her friends even learned first hand. One night she had a friend come over and they were teasing me until her friend took it up a notch and sparked my wife’s pegging fetish. Sometimes my wife will wear her strap on out and about and if she sees a moment she will have me bent over somewhere. She’s taken me in changing rooms, in an empty parking garage, out in the woods, even at family functions and I gotta say I do love it.

So that was kind of a long introduction so I’m sorry. So recently my wife has wanted more from our sex life. A couple months ago she expressed to me that she wants me to try real cock. She wants to watch me suck a real one not just her strapon. She wants to see me with a big load in my mouth, on my face, running out of my freshly fucked hole. She went to work looking for someone, but she’s kind of picky she didn’t want someone super masculine, she wanted someone that she would have fun watching while I was getting railed. After a month of her looking she finally found someone, she didn’t tell me any of the details until in the moment.

I came home after work one Friday to my wife and an older woman sitting on the couch a little less than dressed giggling with some wine. My wife jumped up and made her way to me in her underwear and met me with a kiss. She pulled me over to where they were on the couch and commanded me to strip for them. Once I was down to my thong the mystery woman giggled, “ oh you weren’t lying he does barely fill those panties”. Their laughs made me twitch in my thong. My wife commanded me to kneel in front of them, when I got down in front of them is when I saw that the older woman had a bulge in her panties. My eyes locked onto her crotch as they talked and giggled between themselves. My wife looked down at me staring and laughed, “ well are you just going to stare or are you going to put it in your mouth, she’s here for you. I’ve gotten to used to your little dick something like hers would rip me in half “. The woman slipped her panties off showing her magnificent semi hard cock. Even not fully hard she was bigger than mine.

I knelt there frozen until my wife grabbed my head aggressively and pulled me to her, “ listen don’t make me look bad, you know you want this. Give me a good show and maybe I’ll reward you later” then she spit in my open mouth. I shakely reached for her cock and grabbed it and I slowly stroked her before leaning in and kissing her tip. “Good boy, suck her big cock. Just wait until you get her fully hard”. I started to suck this strangers cock like I had done to my wife’s strap on so many times. I sucked harder with each one of their degrading words. When I first opened my eyes I got a shock as both my wife and the other woman had their beautiful breasts exposed and my wife had one tit in the woman’s mouth. I was having an absolute blast with this huge real cock in my mouth and getting to watch my wife with this other woman. I knew she was close when I felt the other woman firmly grabbed me by the hair. The first shot of her load shot down my throat and I choked but she wouldn’t let me pull up for air. As much as I tried I couldn’t swallow fast enough, rope after rope shot in my mouth before I was finally released. As soon as her cock popped out of my mouth the final rope of cum shot me in the face.

“Mmmm, that was so hot baby how did you like your first taste of cum?”, my wife asked. As I was licking my lips and trying to catch my breath I responded, “ mmm that was pretty good”. “ now get up and lead us to the bedroom “, the mystery woman(I found out later her name is Brittney) said. I got up and after they each planted a hard smack on my ass I led the way to the bedroom. When we got to the bedroom my wife shoved me on the bed and ripped my panties off of me. She got between my legs and engulfed my dick in her mouth and Brittney got into position by my face and layed her already hardening cock on my face. It didn’t take me too long before I blew my load in my wife’s mouth. She sucked up every last drop and climbed up and spit my cum over top of Brittney’s dick, running down her cock to my lips.

They got me to sit up and on my knees with my face down. My wife climbed on my back and spread my cheeks so that Brittney could lube my ass. I could definitely feel the size difference between Brittney and my wife’s strapon. My wife moaned as she watched my back door stretch around her cock. It felt like forever from when her head pushed in to when her hips reach mine. Once she took a couple slow strokes she pick up the pace extremely. She kept going until the force of her strokes were too much and my hips and stomach were flat on the bed. My wife had never fucked me this violently, it was amazing I’d never felt so abused in my life. In the middle of me getting my cheeks destroyed I heard my wife let out moans louder than mine but when I went to look up I couldn’t move my head, Brittney had her hand pushing my head down. She finally let out a couple of slower but hard strokes before one very hard stroke and I felt her erupt inside me, it felt incredible.

In the aftermath I layed there with my wife and Brittney. I thanked both of them and I asked my wife if we could do it again sometime. My wife teased me and said, “ if youre a good boy”.

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 just goes 'ok' real quiet and drops to his knees.

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.

True story

Over the last three years I have had fun servicing a local coach from the high school. Usually we meet in his backyard shed and I suck his cock. I don’t know his name, but I know his cum is extremely creamy and I alway swallow his seed. I have let him fuck my pussy a few times and on some occasions, he has filled my cunt after my other friend has already been there. Recently, I contacted him for cock and he told me to meet him by the baseball field. I quickly got ready, put on my bra, shirt, plug, sandals and a skort I like. When I got to the field, he led me up the stairs to the press box. We went inside and it was a larger room with a couch at the back. I could look across to the football practice field and there was football practice going on. I don’t know if anyone could see us, but I pulled his coaches shorts down and began sucking his cock and balls. After a few minutes of that, his cock was erect and my pussy was throbbing, so I pulled my plug out, got on my knees on the coaches couch and he slid his hot, aching cock into my sloppy pussy. He had his hands on my hips and rode me for about 10 minutes. He moaned as he shot his load into my hot cunt. He rested on my back for a minute going soft. slowly, he pulled out of me, and I popped the plug back in. I then got on my knees and sucked the remaining seed off his dirty cock like the good little cock slut I am. Once he had used me, he had no further use for me and I went home. Once there, I pulled out my plug and lovingly tasted his creamy cum from the plug and from my fingers as it oozed out of my cunt while I rubbed myself all over remembering how sexy it was in the press box. I can’t wait for another trip to the press box.

So most of my stories are about me as a crossdresser but I have also met many sexy TS women while in guy mode. This is one of those stories. I was on a work trip but couldn't bring anything to dress up in. I was online looking to see if I could find a CD or TS to join me in my hotel room for some fun.

I got a message from a beautiful blonde TS, she said she'd love to come over and give me a massage and top me if I was into that! I said absolutely and we set up a time to meet in a few hours after she got off work.

When she arrived at the room, I let her in and she gave me a hug, her fake tits felt amazing pressing against me. I could tell they were cheaper ones because of how firm they were but I actually like those.

She told me to strip down to my underwear and lay down on the bed. Once I did, she did the same in front of me, taking her bra off but leaving her panties on. She told me to flip over so she could rub my back, then got on top of me and started giving me an oil massage.

I kept on trying to grind my ass upwards when I would feel her bulge between my cheeks. She pushed me down and said I'd be getting that eventually.

Once she was done, she told me to flip back over, where she straddled my face and pulled her thick cock out of her panties and starting rubbing it on my face. She teased me a little as I tried to get it in my mouth but she soon let me start sucking her. As I sucked her she rubbed my cock over my underwear but didn't start stroking it right away.

It didn't take much of me sucking her before she pulled her cock away and said omg I need to fuck that ass. She got off of me so I could take my underwear off and get on all fours as she got some lube from her bag. Then I felt her pressing the head of her cock into my ass. I thought I was pretty experienced at getting fucked but her thick cock took some time stretching me out.

After a short time and more lube she was all the way in me and started pounding away. She said wow I can tell you love getting fucked, don't you? All I could respond in between my gasps was how good her hard cock felt in me. Then she pushed me so I was laying completely flat on the bed, she wrapped her legs around mine, I could tell she was getting ready to cum. Sure enough, she tensed up and thrust into me as hard and deep a she could, letting out a long moan. She laid on top of me for a moment, and turned my head towards her to kiss her.

She pulled out and said it was my turn to cum. She laid on the bed and told me to stand next to her. She leaned over and started sucking my cock, pausing only to tell me to let her know when I was going to cum. She was amazing with my cock in her mouth, and when I told her I was going to cum she told me to stroke myself and cum on her tits. I quickly blew a huge creamy load all over her gorgeous fake tits.

She told me to lay down next to her, and then told me to clean up my mess, grabbing the back of my head and guiding it to lick the cum off of her tits. She gently played with her cock some more while I licked my cum off of her, as she told me to show her that I swallowed it.

After we laid there for a few minutes, she said let's go take a shower. The hotel room had a nice big shower for us to wash each other in. As we bathed, she got hard again, and pushed me down to her knees to start sucking her cock again. She said I was too good at it for her not to cum again. For having already cum in once already, I was surprised when she shot a decent size load in my mouth. I showed it to her and she told me to swallow it.

From there we finally cleaned ourselves up in the shower, dried off and got dressed. I walked her to the door, we kissed and said goodbye. A little while later, I got another message from her, she said thanks for such a fun time and she was already stroking her cock thinking about the fun time we had together!

I have been generally straight my whole life but at my friends bachelor party, things went a different direction. The night started normal, good food and drinks flowing. After a few stops at different bars, we climbed into a car and his best man(a gay man) said we were going to a club. I immediately head to the restroom of the club and that’s when I realized what kind of club it was. I was drunk so I just went with it. As I came out of the stall, there was this gorgeous woman doing her makeup in the mirror and I smiled at her as I washed up.

In the club, I started dancing and drinking more and was surprised at the number of hot women out on the dance floor. After a bit, I felt a woman dancing up on me and I recognized her from the bathroom. I turned and started grinding on her and before long we were all but fucking on the dance floor. We made our way to a dark corner and began to make out. I told her I had a place nearby and we left in a hurry.

Once I got her inside, we continued to make out and started stripping. Then she pulled out her big cock. My eyes got big and then I started to freak out a bit. I had never been in that situation. She calmed me as she started making out with me again. Before I knew it, she was blowing me and I was in heaven. Then I did something I hadn’t ever done and haven’t done since. I moved to where I could blow her, and we 69’d for a bit. It was so hot and I was on cloud 9.

I ended up fucking her ass and we came together. She left after giving me her number. I texted her several times but we’ve never hooked up since.

in my 20's (2024) i was curious about how can i meet a trans lady on GRINDR, but it seemed pretty impossible until one day one text pinged me with "you bottom?" i looked upon profile, the gender was female so i started saying things like am a male and i think you mistaken me as a girl because of my anime pfp, but she then sent a pic of her with her big thiccc 7 inch dickk, saying am a trans

so i knew it was my chance and i cant fumble it!! i started talking to them as we both were straight forward she wanted cheeks to crack i wanted that lightsaber to hold,
so we decided to meet, she shared her location i reached there and realised its not her space as someone else were there too,
and that someone was the owner of that room, so it appeared he was chill with us doing stuff but ahhhhh human lust human greed, he said to me that you must suck me too if you want to do stuff with her at my space, and horny me, accepted...
back to her, man she was so direct, pulled her cock out of underwear and made me suck it it was good and like flavorful, and after a bit she tossed me over and blessed me with her 7 inch excalibar and that owner came to me and watched me for a while and stuck his cock on my lips and said nothing i was horny so i sucked him too out of sympathy, as we continued she came into me and it was soooo goood my whole legs and body were shaking, but as we know good things come to an end.
It was a one-time experience, and i never ever met that person again.

i still remember that night.

So a quick download of background info
I was married and a swinger for a long time.
Towards the end of the marriage I discovered I was bisexual and since then have been trying to explore more bisexual experiences mostly with couples.
(I have a few stories of that posted on my page)

Well about two months ago I had finally convinced a bartender at my local lgbtq bar to go on a date with me. I had been going there for a while to try and maybe meet new people. It hasn’t really generated much but me and this bartender built a rapport.

She is a lovely person. I find her very attractive. She is trans and was not born female but is extremely fem presenting. Well call her Amber for this story.

I had asked for her number at one point, she declined but had me add her on Instagram.
This allowed me to at least interact with her from time to time and eventually get her to let me take her on a date.

Fast forwarding, we get to a point where I tell her about my swinging/slutty past. I was worried this would be a deal breaker but she seemed to have more and more questions about it.

We end up hooking up. Pretty standard hook up.
I don’t bottom. I’ve had my ass played with, never really enjoyed it. I have and like sucking dick that’s not a problem but I’ve never taken a dick anally.

This wasn’t a problem for Amber at first……
Amber is 5’4” ish, has a wolf cut that’s half black half blonde. She’s African American. Septum ring. Tattoos Pierced tits that are small and cute. She has been on estrogen for some amount of time. Has an out of the world ass. And has the biggest dick I’ve ever had in my mouth. Like had to get better at sucking dick just for her lol. It was a bit intimidating. It’s actually the only person I’ve hooked up with that has a dick that’s almost as big as mine.

The first couple times went basically the same way. Starts with heavy kissing and groping till I start taking off her clothes. I suck on her tits and move my way down to her cock. I tease it. She has small balls but I love kissing them and even eating her ass. As she’s grown more comfortable shes has started grabbing my head and actually fucking my mouth with I’ve never had done time before. Even holding my head down till I gag.

I’ve only been with purely submissive partners with cocks. It was shocking for me but I did like it.
Eventually we’ll switch to her sucking me or we sometimes 69 but I make sure she gets more oral since it always ends with me topping her.

Another new thing, she can’t always cum. I guess the estrogen starts to mess with that. I do kind of wish she did still cum. She’s the only one I’ve fucked anally and can’t get to cum from it. Hurts my ego lol. She sometimes will kind of cum but it’s not a lot.
But she has came in my mouth. I’ve never had dick cum in my mouth before her. It’s only happened twice, but the first time I gaged, and as I took my mouth off a tiny bit shot right over my eye/eye brow.
I couldn’t believe that a little over a year after finalizing a divorce I was on my knees sucking dick and had cum on my face lol.
She gives me warnings of a “possibility” of cum now. But I did manage to keep it all contained the second time it happened and she made out with me while the cum was still in my mouth. Which made me feel super slutty but the passion she had, the way she bent and reached down grabbed my head and brought me to her mouth was so fucking hot.

So we’ve been seeming each other multiple days a week now. And she has started to express wanting to top me. And how it’s a little unfair that I get to top her but not the other way around.
I tried not to be selfish but honestly was super hesitant and I didn’t really want to.

We agreed to start small and start with smaller toys.
First it was us having our normal routine but she slipped in a butt plug while sucking my dick and then I’d fuck her with it still in me.
This did make sex feel better for me, but hated it the moment after I came lol. I didn’t want it there anymore and felt annoyed I had to give effort in getting it out.
But for her I would keep exploring a little.
She bought a new toy for me. Invited me to her place.
When I arrived she brought my right to her couch. Sat me down and told me to get naked. She takes off her comfy clothes and has black lingerie on. She goes down on me and is sucking my cock. She scouts me closer to the edge of the couch and lifts my leg some. She starts eating my ass. Then I feel her lube it. As she sucking I feel/hear a vibrating toy starting poking my ass. It doesn’t go in right away I kind of tense up. She tells me to relax and starts deep throating my cock and I feel my ass open to her vibrating anal bead type toy.

This is intense. It’s like the inside of my cock is vibrating. I’m letting out moans I’ve never made before. It’s like a whole body high. She’s slowly putting more into me. I can feel when a new bump/bead gets inside me and my whole hole recloses up around it.
I ended up exploding. She’s trying to swallow it all but between my convulses, and never ending cum it’s pouring out of her mouth. I can feel it dripping down my cock, all while my ass is pulsing on the toy.
I’m telling her to take the toy out but she’s loving this and she’s still sucking and putting pressure on the toy teasing me till I completely tap out.

I will say once the orgasm ends, I hate having to have what ever is in my ass taken out. I’ll never enjoy that part lol.

So we explore with that toy a few times and finally agree to let her fuck me. I was surprised on how different she felt compared to the toy. The toy made every thing vibrate and feel “full” her cock made me feel “open” like even if she took it out I feel like was open. But the real difference was feeling it deep inside me. It felt like the tip of her cock was touching my stomach and the base of my cock at the same time.

It did take some effort for her to get into me. But I was bent over ass in the air. She was standing on the floor at the edge of the bed. Grabbing my hips, slapping my ass, calling me a “good boy” it was a such unique euphoric feeling. I can’t come from it unless she’s jerking me off at the same time. But she took my anal cherry.
I’m learning how to be on top with her inside me now. I don’t really enjoy being on top but doing it for her enjoyment.
I still top her way more than she tops me but I am regularly taking cock in the ass now.
And sometimes I’m the only one getting topped in a session.

Recently I took her to the local swinger club. We didn’t have a goal of swinging but just wanted to show her it since she was interested. She got to dress slutty and be half naked around other half naked sexual people. Got to mingle. We fucked in a room that people could watch and a lot of people did.

But now she wants to top me while other people watch. We’ll see lol.

This morning I was up early because I had an early morning run scheduled in a city park about 30 minutes from the house. I left early hoping to score a hookup before the run but no fish were biting.

Then when I'm about to give up hope and lace up the shoes she responds to a message of mine. We exchange pics and I tell her I'm looking for some early morning romance. She says that sounds great. I send her another pic and she tells me that she's a top.

I am too excited. I exit the park and haul ass to her house planning to get my workout in there.

I get to her house and she answers in pajama pants and a crop top. Her bulge sways side to side as she walks back to her couch.

She grabs the hem of her shirt and pulls it up to reveal two of the softer large bolt ons that I've seen in person. I kiss her neck as my fingers trace the nipples and then gently massage her breasts. They're not as soft as natural, but they're not rigid.

Then she eases her pajamas down to release her absolute unit. Fully shaved and a gorgeous vein running down the length of it to her bulbous head.

I drop to my knees and take her between my lips letting my tongue twirl over the tip. One hand embraces her shaft easing it further and further into my throat as my other hand caresses her smooth sack.

She moans tenderly as I continue to suck and begin pulling off my gym shorts. I take my position over the edge of the couch. I tell her I had cleaned out and I had played this morning. I'm more than ready for her. At this point, I crave her and need her inside.

She lubes her head and gently places it at my entrance as she tells me that I'm tight. It'll take you I promise her. She pops into me and I feel my heart race as the amazing feeling tingles through me.

She slowly starts to get a rhythm. After a while, I start to buck back into her aching to feel her harder and deeper. She props a leg up and begins driving deeper and deeper into me. After mere minutes, I feel her pace quicken and her breasts press against my back as her mushroom tip pulses inside of me with her seed filling me.

She pulls out of me with the entire lengths of her shaft glistening with her cum. I eagerly take her in my mouth licking it clean.