Met an amazing trans woman on Tinder [MT]

This is a true story, and I hope that comes across.

I am in my early thirties, and recently my life changed dramatically. I’ve been with my partner for over ten years, but—suddenly, catastrophically—our relationship began to fall apart, until we decided to separate. Not completely done, we decided that, while separated, we should explore ourselves sexually. Well, not really we—this was her idea, not mine—but if she was going to fuck around, then I was going to as well. We were, officially, “separated, but in an open relationship.”

So, for the first time ever, I installed Tinder and got started. Luckily, I hadn’t slouched off too much, and I’m pretty fit. I’m muscular, of above-average height, and not bad looking. And it turned out, other people thought this too! I was getting matches, and dates! As depressed as I had been by the wreck that was my relationship, this cheap acknowledgement cheered me up.

However, my previous relationship wasn’t quite over yet, so I made it clear that I was not looking for anything serious on my profile. This key phrase, “Looking for casual dating,” did most of the heavy lifting, filtering out women looking for something serious. And once I matched, I would, after a bit of conversation, clarify my situation and what I was looking for. Sometimes they said “thanks, but no thanks,” but, often enough, they would say, “Great, that’s exactly what I’m looking for.”

I was having a great time. Often, we would grab drinks, go back to my place, and have great sex. Because of the city I was in, these ladies came from all over the world, and were very interesting. It was hard to decouple my sexual enjoyment from my intellectual connection.

One day at work, my phone buzzed. I got a match! She was very pretty, in her early twenties. Dark hair, dark eyes, a pretty smile, and some freckles. She looked like she might own an art gallery, and the photos were very Terrence Malick-y. She also looked incredibly… kind. I’m not sure how one can tell that from a photo, but I found it incredibly attractive. I checked her profile, which I only do after I match. There were excerpts from poems in Spanish and French, languages I understood and spoke. Below, it said, “trans woman” in both languages.

I immediately got very excited. I know this will rub some people the wrong way, but I’m trying to be honest here: I’ve been masturbating to trans porn since I’ve been masturbating to porn… I love it. I find it incredibly sexy and arousing. I had assumed that I would be with my previous partner forever—a cis woman—and I would never get to experience sex with a trans woman. Of course, I’ve always wanted to fuck basically anything that moves, so that never really bothered me—that’s just inherent in monogamy—but now, maybe, was my chance! I was at work when I got the match, and the idea of having sex with this woman made me so horny that I went to the nearest handicap bathroom and beat off to her pictures.

But, I also felt a bit nervous. I didn’t want to “fetishize” trans women or treat her like an “experiment.” I’m not applying for sainthood, but I try to at least not be a monster. I had read about this phenomenon, and how terrible it makes trans women feel, and I certainly didn’t want to hurt anyone. But, in a certain way, I was “experimenting” with every woman I met recently. It was all, one, big, sexual experiment. I also had gotten the feeling that I had been something of an experiment for some women… And then, “fetishizing”… Was I “fetishizing” this woman? Maybe. Though, for example, I also had a thing for women with fat asses. Did I “fetishize” fat asses? Again, maybe. But then what did “fetishize” even mean? I spent some mental energy cranking away at these thought-anxieties without much to show for it. Finally I decided that, rather than overthink things any more than I already had, I would just proceed slowly, honestly, and respectfully, and play it by ear.

A few days later, I messaged her in Spanish about one of the poems on her profile. She responded in Spanish, saying her English, was not so great, and she had come to this place to practice it a bit. No problem, we could chat in Spanish.

Now, I really hate messaging or anything to do with phones. I like meeting face to face and having a drink, so I tend to ask for that pretty early on, and most women are very receptive to the idea. But she said she couldn’t. She would love to, but she was incredibly busy with deadlines. Fine, I said, let’s keep talking. And we talked for two or three weeks, and she was always busy, or something always came up. The conversation wasn’t exactly sparkling either… a little dull. I was getting annoyed and bored. What was taking so long? Maybe I was being cat-fished? Or maybe she was too self-conscious to meet in person? Had she gotten bored of me? Whatever the reason, I had given up and written the whole thing off, so I texted her asking if she was still interested or what. She just responded with, “Hi, I’m ready to meet :)” So we made a date at a bar later that night. I was expecting very little. I had gotten tired of the waiting, and felt like she was just meeting me out of a sense of obligation. It was a Wednesday, and I expected a couple of quick drinks, some awkward conversation, and a “See you never.”

She picked the bar, and I got there first. When she finally arrived, I was shocked. She was gorgeous, much more so than her pictures. Her hair was very long, down to her back, and a bit wild in a fashionable way. She was very petite, maybe just over five feet tall, and thin. She had hip, round, thick-rimmed glasses, and red lipstick. We did the two-kisses thing, and started talking immediately. The conversation was going at 100mph. She was incredibly intelligent and interesting. She was an academic, and a very successful one, it seemed. She had won a prestigious scholarship. Later I would google her and find her quoted in popular articles about her expertise. She was very interested in left-wing politics, and so am I. We talked about marching and organizing, and the political situation in our respective countries of birth. When she spoke about this, she was very intense and confrontational, which I found incredibly sexy. We spoke in Spanish, French, Italian, mixing all three and switching back and forth… At some point, she mentioned she had an interest in Russian, and I managed to recall a bit of Russian I had studied almost ten years ago, and we managed to exchange a few awkward phrases.

The topic of her being trans never came up. She mentioned her involvement in LGBTQ and feminist issues, and we discussed them, but in a sort of abstract way. She shamed me playfully for not being more involved in these issues, and I conceded that I had become a bit lazy recently. I was so wrapped up in our conversation that I had even forgotten she was trans. At some point she said,

“I knew you were an interesting man from the start”

“How did you know that?”

“I mean, you messaged me.”

“I mean, of course I did. Why wouldn’t I have? We matched, and look at you!”

“Not all men would have.”

“What? That can’t be true. You’re so gorgeous. Is it the language barrier thing?”

“No… It’s not the language barrier…” and she laughed

It took me a few seconds before I replied,
“Oh, yeah, right. Sorry–I mean–I’m an idiot.”

We talked for more than an hour before I realized we hadn’t even gotten drinks yet. So I got us some wines, we kept talking and talking. The time flew by, and soon it was closing time. We had been there for hours before she said

“I’m amazed.”

“Amazed… By what?”

“You. You are amazing. I never expected to find someone like you here. On Tinder. I just can’t believe it.”

“Me? You’re the amazing one. You know all these languages, and you’re so accomplished and dedicated. I’m just some guy…”

I didn’t know what to add to that, and stared silently at her as I thought of what to say next. Her eyes were like deep pools, and for a second, I feel into them. While down there, she moved in, and started kissing me, deeply. I put my hand on her leg, and we made out for a while. Then, she grabbed my hand, got up, and said, “Come.”

I followed her outside, and she started moving down the street with a purpose, with me following her. Around the corner, I grabbed her, spun her around, and made out with her against a wall.

“Where are we going?” I asked

“‘Where are we going?’ Where do you think we’re going?” She laughed. “To my place!”

So, things were moving faster than I thought. At this point I gave myself a mental pat on the back. Without trying, I had managed to get invited back to her place on the first date. Nice.

She lived a block away. Her roommates were gone. We started making out in the living room. I took off her coat, and her blouse. Her body was very skinny and toned, and very slightly tan. Her breasts were nice: Big for a her small frame, but not ridiculous. These were the first fake breasts I had ever seen in real life! They were harder than real breasts, a little rounder than real breasts, but they still felt and looked great. We were kissing and groping each other, my hands running all over her back and ass. It was very hot, and more intense than usual. She would bite my ear and lick it. I was pulling her hair as I kissed her. We were like two animals. Sometimes she would stop me from kissing her, slap me hard on the face, then kiss me. I had never been slapped before, and I really liked it.

She was still wearing a skirt and black tights. I took off her skirt, and I saw she was pitching a massive tent, massive for her size, at least. In any case, she was rock hard. Well, alright, so she can get hard. I quickly remembered that I had no idea what I was doing. Now what? When I make out with cis women, I like to stick my hand down their pants and play with their pussy. Should I do the same here? No pun intended, but it felt like a loaded gun. I had read and heard trans women talking about how they hated their genitals, hated them being touched or even acknowledged, so didn’t want to just reach down and touch her cock. It also felt weird and selfish to just not do anything.

So, I just asked: “Should I touch it?” And rather than answer, she just took my hand, and slowly placed it on her dick. It was nice. My first dick. It was eerily smooth and spongey. It was circumcised, shaved, very hard, and about 5 inches. So I slowly masturbated her as we made out, and she moaned a bit. At one point I picked her up, and she loved that, and started giggling. She said I was very fiery, and that she liked that. I told her she had an amazing body and amazing eyes. She thanked me. She said she loved my lats–and it’s true, I do work hard on my lats.

I picked her up and moved her to her bedroom. It was a tiny room, with a small mattress on the ground. It was not dirty–in fact, her sheets smelled nice and freshly laundered–but it was a goddamn mess, full of books, purses, and clothing everything. I was a little preoccupied by her to give the tidiness of the room further thought, however. At this point, she was totally naked. I stared at her. Her body was very tight and even a bit muscular, like she was really into cross-fit or something. She looked absolutely like a woman, and a very hot one at that, just with a penis, which was still very erect, and bounced around as she walked.

I started kissing her all over. Her shoulders, her breasts, her abdomen, her hips… I moved down and down, until I started licking around the shaft of her cock. She said, “I love that.” So I started blowing her, and she started moaning. It felt wonderful to suck her dick. I’ve always loved going down on women. Nothing gets me harder, and this was no different. I know this is going to sound like I’m trying to be very PC or whatever, but it really did not feel fundamentally different than licking a clitoris. It was just a much bigger clitoris, which made things much easer! As per her aggressive style, she grabbed my head and started basically face-fucking me. That, I have to say, I liked less, and made me gag a bit.

Then I ate her ass. I’m a twenty-first century man so eating ass was nothing new, but the amount of pleasure she got out of it was. She couldn’t get enough of it. She ground her ass again my face. She sat on my face. All the time, while eating her ass, I was playing with her dick, which was starting to leak.

I asked to fuck her, and she looked at me with total surprise: “What, you want to fuck me already? You have this—this wonderful body—in front of you, and you want to go straight to fucking? I’m yours… Don’t you want to enjoy me more?” Goddamn, what confidence! Coming out of somebody else, it would’ve sounded ridiculous and arrogant, but somehow… it worked for her. Maybe it works better in Spanish. It was so hot. And to answer her question, yes, I did want to enjoy her more. So, for what must have been an hour and a half we just kept kissing, sucking each other’s dicks, masturbating each other… I licked her body up and down. I gave her a terrible hickey, which she later got pretty pissed about (“What, you wanted to mark me to make me yours? Ugh”).

But eventually, she told me to fuck her. I laid down, put on a condom, and she got on top of me. She slowly eased herself onto my dick, her dick hard as a rock. I had to try very hard not to cum. For the same reason that I was no stranger to eating ass, I was no stranger to anal sex, which I *love*. It has always been much harder not to cum when fucking a girl in the ass. It’s just so much tighter, and there’s the taboo. Well, her ass was very tight. At first she rode me slowly and sensually. She kept closing her eyes and moaning, while slowly stroking herself. Eventually she sped up. Occasionally she would bend down, kiss me, then slap me hard on the face, and laugh. Sometimes I played with her dick, and sometimes she played with it herself.

We switched it up a few times. We did it from behind. We did missionary for a while. She was very flexible, putting her legs behind her head. She kept running her hands over on my body as I fucked her, and looking into my eyes. She told me she loved my biceps, and how big I was. I’m a sucker for compliments, and I loved it all.

This was becoming a real marathon. If I was ever going to die of a heart-attack mid-coitus, this was it. It felt like we had been fucking at high-intensity for hours. In fact, it had been about two hours since we got to her apartment. Her sheets were soaked with my sweat. I told her I wanted her to cum.

If you have experience making cis women cum, you know things can take a while, and patience is the name of the game. I had assumed that, given that she had a dick, things would be a little more immediate. Turns out, no. Even though she clearly had no trouble staying hard, she still took a while to cum. She straddled me again, and ground her ass on my dick as she stroked her cock. I was exhausted, soaked in sweat, focusing on not summing but also not getting soft, and trying not to die. Then, all of a sudden, she yelled, and started cumming. I had expected, because of hormones, that she would either cum just a tiny bit of clear stuff, or nothing at all. But I was very wrong. She started shooting big, thick ropes of cum. It felt like she came for a solid minute, in different waves. My chest, my stomach, her stomach, her legs, ever her breast… They were all absolutely covered in her semen. Exhausted and satisfied, she laid down on my chest, so that the semen rubbed between our chests. It felt incredibly intimate and hot.

She climbed off me, and asked if I had cum. No, not yet. In fact, I had spent so much energy trying not to cum, that I didn’t even know if I’d be able to from fucking her, specially with a condom on. So I asked her to make me cum, and like magic, she knew exactly what do to. First, she grabbed my dick, starting stroking it, and while doing that, licking her own cum mixed with sweat, off my chest. That was so hot, that I get hard again just thinking about it. She moved to my nipples, and started sucking them. I came like a champagne cork pops. I don’t even know how much, and there was frankly so much semen everywhere, that it seemed ridiculous to care.

We laid there for a while, her head on my chest, nestled on me, at first unable to speak. Eventually, we talked about how mind-blowing and intense the sex was. She said I fucked like a lion… A little cheesy, but, again, I love compliments, and took it. Plus, I’m such an unoriginal idiot that I replied that she, also, fucked like a lioness. She asked me what parts of her body I liked, what about her eyes I liked, and so on, and I told her.

“I wasn’t your first trans, was I?” She asked

“Actually, believe it or not… Yes.”

“No! No way! I don’t believe it! You knew exactly what to do! I love how you love *all* of my body.”

“Of course, you have a gorgeous body.”

She asked me if I all I wanted was to fuck her. I told her, sure, I definitely wanted that, but that I really liked the intellectual connection we made. I told her that, really, I don’t like fucking people I don’t have at least a connection to—which is true. She thought I was full of shit, but what can I do?

Eventually, we both started falling asleep, and I decided it was time to go. It was almost 2am. I gave her a kiss, and thanked her for the wonderful night. She told me that she didn’t expect me to ever text her again; she knew I would forget her. I told her I would prove her wrong.

…

Reader, I did. I texted her that same night, telling her how amazing it was, and kept texting her throughout the week. She had gone on a trip, but when she came back, we saw each other again. No drinks, this time, just straight to her place; her decision. She was wearing a bright summer dress. We talked a bit about her trip, her research, the weather, and the books she had just bought.

But I had been worried. Things had moved so fast last time, that I hadn’t actually had time to tell her that I was in an “open relationship.” I was scared to tell her, afraid it might hurt her. She would think I’m just “experimenting” with her. But I decided that it was the right thing to do anyway. So as she started kissing me, I stopped her, and told her.

She looked at me with a strange, taut face. I was terrified. I really fucked things up, I thought. But then she laughed, and said that I was very cute. She knew, of course. She wasn’t an idiot. She could tell, from the profile, but also how I carried myself. She made fun of me for being so serious. Then she told me that she hated monogamy, thought that monogamy was a tool of the patriarchy, and that she would never “belong” to man, but only to herself. Well, I dunno about all that, but whatever. Normally I would’ve enjoyed unpacking this series of very strong statements over some drinks, but as it happened, her hand was already unbuckling my belt, and I could see her dress bulging. This was no time for talking. We got to it. It was just as incredible, if not more so, than the previous time, but there was nothing fundamentally different about the sex to justify writing it out again. I’m not sure what the future will bring for us, but I hope I keep seeing her.

Source: reddit.com/r/gonewildstories/comments/c4v8d1/met_an_amazing_trans_woman_on_tinder_mt