I Cheated on My Girlfriend Again with a Trans Woman

I did it again. I cheated on Carla again, and as I write this the burn between my legs and the taste of someone else in my mouth are still lingering. I’m despicable, I know. Just two months ago I started something with a girl who truly loves me, who texts me “good morning” before I even open my eyes, who worries about whether I’ve eaten. And this is how I repay her: with lies and with afternoons she can’t even imagine.

The problem, or my downfall, is always the same. I like women, yes, but what really turns me on is having a good cock in my mouth or feeling it forcing its way into me. If you asked me what my ideal partner would be, I wouldn’t hesitate: a trans woman. That exact blend of femininity and something else that nothing else gives me.

This weekend Carla went with her sister and a group of friends to the festival in a mountain village. Three whole days to myself. I should have used them to rest, to miss my girlfriend like any decent person would. Instead, that very afternoon I already had my phone in my hand, browsing a contacts site, looking at who was advertising in the city.

I spent a long time sliding through profiles, comparing, discarding. Some ads were too generic, others lied with old photos that could be spotted from a mile away. And then she appeared.

A Black woman, gorgeous, with a smile that seemed to mock my meager self-control. In the photos, she seemed to have generous breasts and legs you’d want to bite. She caught my attention in a way I couldn’t ignore. I spent a while wrestling with guilt, looking at a photo of Carla in my gallery and then going back to the ad. I told myself no, put the phone face down on the table, poured myself some water, paced around the living room. Ten minutes later I was already writing to her. Weakness won, as always.

We agreed on a time and an address. I showered, put on something decent, and left home with my heart racing and my stomach twisted with shame. During the entire metro ride I promised myself it would be the last time. It’s a promise I’ve made to myself many times before, and I’ve never kept it.

***

She called herself Naima. When she opened the door, I understood the photos hadn’t done her justice. She was taller than I expected, wearing a short dress that clung to her hips, and she gave off a warm, sweet perfume that hit me the second I walked in. We greeted each other with a certain polite awkwardness.

—So what do you feel like doing? —she asked, closing the door behind me.

I didn’t answer with words. I wrapped my arms around her waist and kissed her. Her lips were full and tasted just as good as she smelled. While we kissed, her breasts pressed against my chest and I grew more and more nervous, more impatient. I could have kept kissing her all afternoon, but my body wanted something else: to take her and let myself be taken by her.

I’m not exaggerating when I say I traced every centimeter of her skin with my hands and mouth. I touched, kissed, and licked every inch. I tickled her by accident when I ran my tongue over her armpits — one of my habits that makes some women laugh and drives others wild — and she burst out laughing, breaking the solemnity of the moment. I laughed with her. I was enjoying myself like a kid eating cake, and her dark skin, soft and warm, was exactly that: something sweet I didn’t want to end.

By the time I reached her breasts, I was already rock hard. I sucked them slowly, carefully, drawing circles around her nipples with my tongue, holding myself back so I wouldn’t bite. She stroked my hair and spoke softly to me, affectionately, almost as if she already knew me.

This is what I’m missing. This is what no normal relationship gives me.

Her legs and butt were firm, the kind of body built by someone who really hits the gym. I went down her thighs kissing, nibbling, all the way to her ankles, and then climbed back up. When I turned her around and explored her from behind, I knew I could no longer keep putting off what I had really come for.

***

I took off the last piece of clothing and there it was. A cock that looked like chocolate, thick even at rest. I started at the base, tracing every millimeter with my lips, and slowly worked my way up until I had the head in my mouth. I closed my eyes. I sucked, slowly at first, savoring every nuance, and then more eagerly. At one point I couldn’t help grabbing it and rubbing it over my face, my cheeks, my chin. I wanted to feel it everywhere.

When it got completely hard, I relaxed my throat and let it make its way into me, little by little. I don’t know how long I stayed like that. Too long, probably. It was the kind you’d suck until your jaw couldn’t take it anymore. Long, thick without being excessive; I found it impossible to take all of it, but most of it fit, and I enjoyed it like a delicacy.

Then I went for her ass. That hole seemed to be screaming at me to shove my tongue all the way in, and that’s what I did, until I regretted not having the longest tongue in the world. She was breathing hard, moaning, moving her hips, searching for my mouth. She liked both jobs, that much was obvious.

I stopped for a moment to drink some water — from sucking so much, my mouth was dry — and then she was the one who took control. She grabbed me, knelt down, and in one go took my whole cock until her nose brushed my stomach. She surprised me; mine isn’t huge, but still. You could tell she had experience. She gave me such a good blow job that I had to gently pull her away before I came right then and there.

—Fuck me —I asked her, barely finding my voice.

***

While she prepared the lube and licked me to relax me, I reached for the poppers. I don’t like them that much; they give me a headache and sometimes make me a little dizzy, but for a cock like that I wanted to be fully surrendered, with no tension. I inhaled. I felt her finger go in first, spreading the lube, and then the head, slowly, with a patience I silently appreciated.

I let out a long breath and made that face of pain that is really pleasure. She paused, waited for me to get used to it, and kept going. Centimeter by centimeter, that cock went in and out, first softly, then harder, faster. At first it was pressure and a bit of discomfort. Then came an enormous pleasure that made me moan like a madman. My whole body seemed to be screaming “more” at her.

She fucked me for a good while with a movement of her hips that sent me up to heaven and dropped me back down at once. She changed my position a couple of times, lifted one of my legs, held me by the waist with one hand while with the other she forced my back to arch. She knew exactly what she was doing, and I let myself be carried away like someone surrendering unconditionally.

At one point I had to ask her to stop, because I didn’t want to finish yet and because I also wanted that beautiful ass I had so carefully eaten earlier.

I put her on all fours and fucked her. Every moan she let out was one step closer to the end, so I turned her onto her back to see her face while we both came. When I was close, I did something I didn’t even fully understand myself: I sat on top of her, put her cock inside me again, and it only took a few seconds. I came with a groan that must have been heard in the hallway.

She smiled, breathless, and asked if I wanted her to come in my mouth. I nodded without hesitation. I knelt in front of her and waited for her moans to grow more intense. When I saw she was about to finish, I took her all the way in and sucked until the spasms filled my mouth. I swallowed everything, without disgust, and kept sucking until I left her dry, until her cock calmed down again. Then we hugged, shared a long kiss, and went to shower together, laughing about something stupid like two people who’d known each other all their lives.

***

I left there with my ass burning and the taste of semen still in my mouth. And then, as always, the guilt arrived right on time.

Carla’s image came back. Her smile, her “good morning,” the way she worries about whether I’ve eaten. I felt miserable, because she doesn’t deserve any of this. I love her, I truly do. But trans women and a good cock are my downfall, and I don’t know how much longer I’ll be able to keep this double life going before everything falls apart.

Maybe the right thing would be to confess. Maybe the right thing would be to set her free so she can find someone whole, someone who doesn’t open a contacts site as soon as she closes the door. But I’m a coward, and while I write this I’m already thinking about the next time.