The Trans Woman Who Paid Me to Fulfill My Fantasy

You can call me Damián. I prefer the pseudonym because what I’m going to tell you I never told anyone, not even the friends with whom you think you can talk about anything. I’m from Santo Domingo, although I’ve been living in Vietnam for nearly a decade for work. I consider myself a textbook heterosexual guy: women drive me crazy, their skin, their curves, the way they breathe when I have them naked under me, with their legs spread and their cunt wet, waiting for my cock. That’s the easy part to explain. The hard part comes after.

I’ve been married to a Vietnamese woman for eight years. I love her, truly, and our relationship is good in almost every way. The problem is that our sex life died slowly. Not because of me, because I still have the same appetite as always, but because she lost interest. We used to fuck every day, sometimes twice; now we can go a month, sometimes two, without touching each other. We shower together and nothing happens: I look at her wet tits, her round ass, and she soaps herself up as if I were a wall. I end up jerking off almost every night, silently, staring at the ceiling, with a hard dick and a limp hand that isn’t enough. And that’s where all this was born, on those long nights.

A couple of years ago I got on a social network one early morning, one of those where you keep scrolling through photos without thinking. I came across the image of an amazing girl: narrow waist, firm legs, a mouth that looked drawn in. I opened the profile out of curiosity and, as I scrolled down, I realized she was a trans girl. I kept staring at the screen longer than I wanted to admit, my cock hardening on its own inside my pants.

In a night of madness, I might even go for it, I thought, and then I laughed to myself at how ridiculous it sounded.

But the idea didn’t go away. It kept turning over in my head, half curiosity, half provocation. I felt split in two. On one hand, I wanted to know what it felt like to fuck a trans woman, to put my cock in her, hear her moan; on the other, I kept telling myself I’m not attracted to men, not even the delicate ones, because I like women too much to get confused. It was a contradiction I didn’t know what to do with.

***

One of those early mornings, around two, I was still awake on the couch in front of the TV. I wasn’t working the next day. I got the usual urge, and without a woman around, the only possible company was my own hand. I opened one of those videos people watch in these cases. I started with the usual category, the one I’ve always watched, but something made me tap for the first time on the tab that said “trans.”

It was the most intense wank I can remember. I chose a video in which a very tall brunette, with perky tits and a mare’s ass, was letting a guy fuck her face-down, pounding her without mercy. The girl moaned like a bitch in heat while he shoved his cock into her balls-deep. I grabbed myself with my whole hand, spat into my palm, and started jerking hard, eyes locked on the way that woman’s ass opened every time the other guy slid it all the way in. When she turned around and showed her hard cock while they kept fucking her, instead of killing my arousal it sent it through the roof. I came seconds later, with a long shot that filled my hand and stained my stomach. Not because of cheap kink, but because I was crossing a line I’d set for myself, and that made everything race. When I finished, I stayed still for a while, heart pounding and semen cooling on my skin, wondering what the fuck was happening to me.

The next day I was on a dating app, scrolling through profiles aimlessly, and I came across a Colombian trans woman’s profile. To be honest, she wasn’t the kind who stops traffic: she had slightly harsh features, but her face was feminine and her hair was very long, black, and well cared for. In her description she’d written just one phrase: “I adore crazy shit.”

I sent her a simple “hi.” Not even five minutes passed before she replied. We started talking and she told me, almost right away, that she liked dark-skinned men, especially Americans. I speak and write English with no problem, and I noticed hers was weak, so I played along: I told her I was from the United States and was working in Asia for a while. A dumb lie so nothing would get complicated.

—Would you like us to spend some time together? —she wrote without beating around the bush.

I said yes, but I set a condition I didn’t even fully understand myself.

—Only if you pay me —I answered.

It wasn’t about the money. It was about some weird thing with myself: if I was being paid, I felt like I was the one in control of the situation, that I wasn’t doing it because I was into a man but almost as a service. An excuse, I know. But at that moment I needed it to get myself to go through with it.

She accepted. We agreed on what at the time was about two hundred dollars. She sent me the address and, since it wasn’t far, I went that same night.

***

Her apartment was in an old building with narrow hallways. When she opened the door I confirmed what I already knew: she looked better in the photos. But I was already there, standing in the doorway, and curiosity outweighed everything else. She had a woman’s face, her hair loose over her shoulders, dark red lipstick, and a sweet perfume that filled the whole place. She was wearing a short black silk robe that barely covered her ass.

The first thing I did, as soon as we went in, was grab the money. She had it ready on the nightstand, next to the bed, neatly folded. I counted it discreetly and put it in the pocket of the jacket I’d left on the chair. Only then did I breathe easy.

I undressed slowly while she watched me seated on the edge of the bed, legs crossed. As soon as I dropped my underwear and showed her my cock, already half hard, her eyes widened and she licked her lips. She knelt in front of me without me saying anything, took my dick by the base with one hand, and looked at it for a moment, as if measuring it.

—What a nice cock, daddy —she whispered in Spanish, then repeated in her broken English—: so big, so good.

If I’m being fair, the only really good thing about that night was what came after. Never in my life had my cock been sucked like that. She took it all the way in, down to the throat, without disgust, coating it in spit until it ran down her chin and dripped onto her tits. She’d pull it out, run it over her face, rub it against her cheek, stick it in her mouth sideways like it was a candy too big to fit. She sucked my balls one by one, kept them in her mouth, and looked up at me with those black eyes while she rolled them with her tongue. Then she’d swallow my cock whole again and work it with her throat, squeezing, swallowing, arching her neck so I could go deeper.

—So good, so good —she kept saying between sucks—. I love this cock, I love it.

She went lower, licked my perineum, played with everything, then came back up sucking me from the base to the tip with her tongue flat. She took one of my hands and placed it on the back of her neck, pressing herself against me so I’d grab her hair. I understood, and I took her head with both hands, shoving my cock down her throat until she made those guttural noises, that dry gag some girls like. Her eyes filled with tears, her mascara ran, and she nodded up at me, asking for more. I pushed harder, drove it into her to the balls, and she took it, her throat gripping my tip like a warm fist.

I had my eyes closed and, for a second, I forgot who I was, my wife sleeping on the other side of the city, the passport lie. Only that mouth existed, that throat, that tongue wrapping around me. When I opened my eyes again, I saw her face smeared with saliva, hair messy, mouth open waiting for another thrust, and I almost came right there.

She stayed like that for a few minutes until she reached toward the nightstand, took out a condom, and slipped it on me with her mouth, with a skill that left me speechless. That was where what I’d really come for began.

***

She climbed onto the bed, took off the robe, and showed me her whole body: hard, perky tits with dark, erect nipples, a slim waist, and between her legs her own cock, smaller than mine, pointing at me. She turned around, got on all fours on the bed with her back to me, and spread her cheeks with both hands so I could see her ass properly. She poured a good amount of lube into her hole, let the stream run between her ass cheeks, and with one finger started spreading it in circles, pushing it in to the knuckle and pulling it out slowly.

—Come on, daddy, put it in —she begged, bouncing her ass in the air.

I moved closer, rested the tip of my cock on her asshole, and pushed carefully. Even so, everything felt tight, much tighter than I’d expected, like my dick was being squeezed by a hot, elastic ring. I went in little by little, millimeter by millimeter, while she let out sharp, almost sing-song moans that cut off every time I advanced a little more.

—Oh, daddy, slow, it’s big —she moaned, face buried in the pillow—. Put it all in, give me all that cock.

When I was finally all the way in, with my balls resting against her cheeks, I stayed still for a moment to get used to that new sensation. The heat, the pressure, the way the muscle closed around my cock and then loosened again when she breathed. Then I started moving, first slowly, pulling almost all the way out and sinking back in at a measured pace, watching how her asshole stretched and tightened with each thrust. She reached down and grabbed her own cock, jerking it to my rhythm while she kept moaning into the pillow.

I grabbed her hips and sped up. I started fucking her harder, with dry thrusts that made my thighs slam against her ass, and the noise filled the room: skin on skin, her sharp moans, my broken breathing. The building had thin walls and, in the middle of everything, I thought the neighbor next door was probably hearing us and knew perfectly well what was happening. Instead of slowing me down, that idea made me even hotter. I slapped her ass hard, grabbed her hair from behind and yanked, and she screamed with pleasure.

—Like that, daddy, like that, fuck me, don’t stop —she gasped.

But I couldn’t hold out long. The mix of novelty, nerves, the tight heat of that ass around my cock, and months of pent-up tension got the better of me. I felt the load rising from my balls and couldn’t stop it: I came fast, too fast, in barely a few minutes, with my cock buried to the hilt, trembling, feeling every shot hammer against the latex inside her. She came almost at the same time onto the sheets, clenching around me with her ass every time another burst came out of her cock.

I let myself fall onto my side on the bed, breathless, not fully believing what I’d just done. She lay down next to me as if nothing had happened, lit a cigarette, and offered me a cold beer from a little cooler beside the bed.

We talked for a while. She started showing me photos of her supposed boyfriend, a dark-skinned man who, according to her, lived in the United States. She even sent me a couple of videos of the two of them fucking. I watched them with a strange distance, as if none of it were entirely real.

After a while, without even noticing, the excitement came back. My cock started hardening again on its own, there on my thigh. I told her, and she laughed, grabbed it with her hand, and gave it a gentle shake.

—My ass hurts a little, daddy, but I want to try yours again —she told me—. Wank it and come on my face, feed me.

She settled on her knees beside the bed, mouth open, and I sat on the edge, jerking off for her. I took my cock in my hand, started pumping fast, and every few seconds she licked the tip, or she’d take my balls into her mouth while I kept working myself. She pressed one breast against the tip of my cock and rubbed it there, the hard nipple grazing me, and that finished me off. I warned her with a grunt and she closed her eyes, stuck out her tongue, and waited.

I finished over her lips and cheeks, with three or four thick shots that painted her face. Semen landed on her forehead, her eyelids, her upper lip. She took it as if it were the best thing in the world, eyes closed and smiling, and at the end she opened her mouth and let the last shot fall inside. She gathered what was left on her cheek with a finger and put it in her mouth.

—Tastes sweet —she said, licking her lips—. Good cum, daddy.

***

I dressed in silence, tucked the money away properly, and left. I went down the stairs with a mix of guilt and relief that wouldn’t let me think clearly. In the taxi back I promised myself I wouldn’t do it again.

I didn’t keep that promise. We ended up seeing each other about once a week for roughly two months. She kept paying me, though each time a little less: we started at two hundred, then it was one fifty, and the last time it was barely one hundred. It wasn’t about the money, I already said that, it was about the game I’d invented for myself so I could feel comfortable. And while it was only that, it worked.

What ended it all was something else. One afternoon she started talking to me differently, telling me she was getting attached, that she wanted a real boyfriend, that why didn’t we give it a try. That’s when everything just dropped out from under me. I wasn’t looking for a boyfriend. I wasn’t looking for feelings. I was looking to close out a fantasy that had been burning inside me, and I’d already closed it.

I made up an excuse, told her I was leaving the country, and stopped answering her messages. I felt bad, I won’t deny it. But I also felt free, like someone finally setting down a weight they’d been carrying without even knowing why.

What I took from that experience was an uncomfortable truth: what attracted me wasn’t her in particular, but the feminine figure pushed to the limit, the woman’s body hiding what it hid. That’s why, after that Colombian girl, I was left wanting to try a really beautiful trans woman, the kind that takes your breath away. And, in a way, I did. But that’s another story, and I’m not going to tell it here. Not yet.