That Night a Trans Woman Chose Me as Her First Client

What I’m about to tell happened many years ago, when I still knew almost nothing about myself. That’s why I remember it with that mix of shame and nostalgia that belongs to the things one did before truly understanding oneself. Back then I traveled a lot for work, slept in cheap hostels, and spent my nights walking through cities that weren’t mine. That habit of wandering alone, with no one waiting for me, led me into more than one situation I took years to talk about.

It was a cool night, and I was walking unhurriedly through downtown Guadalajara. I had just come out of a busy plaza, heading for the light rail station closest to the hostel where I was staying those days. I was passing a row of closed shops, with the metal shutters down and the air smelling of wet asphalt, when I heard someone say my name. It wasn’t just any voice: it said my full name, confidently, like someone who couldn’t be mistaken.

I turned around, looking for who had called me. Leaning against a wall was a trans girl, a little taller than me, neither fat nor thin, waving me over. I know her from somewhere, I thought. When I got to her, we greeted each other and she introduced herself with the name she used on her social media. Then it clicked: yes, we had already exchanged messages online months earlier, and I also remembered what she did for a living.

—I saw you as soon as you crossed the street —she told me—, but I couldn’t quite place you. I had to look up your photo on my phone to make sure.

She asked me what I was doing there at that hour. I told her I was heading back from work and going straight to rest. The truth was that by then I had barely had any experience with anyone, and much less with someone like her.

—Why don’t you come with me for a while? —she said bluntly—. You won’t regret it.

I paused a second longer than I should have.

—That sounds tempting —I admitted.

She told me she was working that night and still hadn’t had any luck. That if I agreed, I would be her first client. She kept insisting that we’d have a great time, that I’d really enjoy it, while asking me for my phone number. She spoke to me looking straight into my eyes, without the clumsy urgency I would have expected, and that disarmed me more than any promise could have. I gave it to her almost on autopilot.

—Let me think about it —I told her—. I have to stop by somewhere first.

I said goodbye politely and kept going toward where I had to get to.

I had barely gone a few minutes when my phone started vibrating nonstop. I stopped and looked at it. It was several messages from her, one after another, repeating that I wouldn’t regret it, that she would give me pleasure, that I would be more than satisfied. I stood there reading, undecided. Then another message came, this time with a photo: her hard cock, without any pretense, accompanied by a single line. “This is what you’re missing. Come on, be brave.”

I stared at that image longer than I should have. And just as I was about to put my phone away, it vibrated again. The tone had changed.

—If it’s not now, I’m blocking your number and you can forget about me —she wrote.

I don’t know what moved me. Maybe the threat of losing something I hadn’t even had yet. I turned around and hurried almost running back to the place where I had left her. She was still there, leaning against the same wall.

—I thought you really wouldn’t dare —she said with a half-smile—. But since you’re here, let’s go to a hotel I know nearby.

***

We walked a couple of blocks to a cheap hourly hotel with a faded façade and a blinking neon sign. On the way we hardly spoke; she walked a step ahead, sure of the route, and I followed her feeling my heart pounding in my throat. I asked for a room at a reception with tinted glass, without looking anyone in the face. We went up a narrow staircase that smelled of disinfectant. The moment I closed the door behind me, I felt her body against mine. She shoved me until my face was pressed to the wall.

—I’m dying to try you —she whispered in my ear, while one of her hands squeezed my ass over my pants.

Then she let me go. She started taking off her pants and underwear, and with a gesture she signaled for me to do the same with everything I was wearing.

When she finished undressing, I saw it. A thick cock, about eighteen centimeters, dark brown skin, already with a drop shining at the tip. She grabbed it in her hand and began stroking it slowly, staring at me hard.

—Look at what you’re about to eat, daddy.

She came closer. With one hand she held her cock and with the other she gently pushed my shoulders until I was on my knees in front of her. She rubbed the tip across my face, over my lips, teasing me, before pushing it into my mouth. I started sucking it without really knowing how, letting myself be carried by the pressure of her hand on the back of my neck.

—You suck it so good —she moaned—. Keep going like that. You’ve got such a sweet mouth.

She didn’t let me go on for long. She pulled me up and took me to the bed, where she positioned me on all fours, with my chest and face against the mattress and my ass in the air. I felt a hot spit, and then one of her fingers forcing its way in, in and out, circling. Then a second finger. The pleasure took me by surprise: I hadn’t expected it, but I was liking that new sensation.

At one point she pulled her fingers out and I felt something bigger starting to press against me. Her cock was trying to get in, with difficulty. It hurt, because it was much thicker than anything I had felt before. She pulled back, spat again, tried once more. This time it went in a little farther. She pulled it out, pressed again, and it went all the way in, to the hilt, in one go. A short cry of pain escaped me; from her, a long moan of pleasure.

For a moment I thought I wouldn’t be able to take it. I clenched the sheets with both hands and took a deep breath, forcing my body to relax, while she waited patiently for me to get used to having her inside me. I could feel every inch, the heat, the weight, the way she filled me completely.

She stayed still for a moment, not moving, bringing her face close to my ear.

—What a delicious ass you’ve got —she said—. You’re squeezing me so damn good. You’re nice and tight.

She started pulling out halfway and then pushing back in. She would pause, repeat in a low voice how tight I felt, and little by little the pain began to fade. In its place something else started to grow, a thick pleasure I had never felt before, the pleasure of being speared by that cock that no longer seemed so foreign to me.

***

She pulled it out again, all the way this time. I felt her hands spreading my ass cheeks, leaving me exposed.

—Now your little hole is really open —she murmured.

She adjusted herself and shoved it into me all the way in one stroke. This time the sound that came out of me was pure pleasure. She started the slow rhythm, sliding it in and out halfway, until all of a sudden she stopped.

—Spread your ass cheeks apart with your hands —she ordered me.

I obeyed. I felt her withdraw completely, heard the click of her phone taking a photo of me in that position. Then she placed the tip at my opening again and rammed it into me with a single thrust. The moan it tore from me echoed through the room.

—Ah, what a gorgeous ass —she panted—. It’s been a while since I fucked an ass like this.

She went in and out again, speeding up little by little. With each thrust she let something out, scattered phrases about my ass, about how good I felt. At one point, without stopping, she warned me.

—I’m about to finish. I’m going to leave it all inside you.

The pace turned frantic. Her moans grew louder until they became screams, and then suddenly she sank all the way in with one hard thrust. I felt something hot flooding me from the inside while she trembled on top of my back.

—What a fucking delight of an ass —she said between gasps—. Now I really came hard.

She slowly pulled her cock out. She didn’t let me get up. She took out her phone again and asked me to spread my ass cheeks once more so she could take a couple more photos. I, still breathing hard, did what she told me.

***

When she was done, she let me stand up. Using her body, she pushed me against the wall again and slid her cock, now softer, between my ass cheeks.

—I really liked it —she told me in my ear—. I hope we can do it again soon.

—Yeah —I answered, and I wasn’t lying.

I picked my clothes up from the floor and started getting dressed in silence, still dazed by what had just happened. She was watching me from the bed, unhurried, smoking a cigarette she had taken out of her bag. She gave me her number again, in case I had deleted it, and asked me to let her know the next time I passed through the city. She came closer, gave me a quick kiss on the lips, and let me leave. I crossed the reception without looking up, stepped out into the cool street, and started back to the hostel.

As I walked, with my body still hot and my head spinning, I found myself thinking of only one thing: when I would be able to see her again.