The Trans Woman on the Corner Taught Me What I Was Looking For

What I’m about to tell was my entry into a world I didn’t even know existed back then. I live in a large city in the center of the country, and for many years now I’ve had encounters with trans women. I have other stories tucked away, some so old I can barely remember them, but this first one is etched into my mind as if it happened last night.

At that time I was twenty-three. I was a shy, skinny guy, the kind women like but don’t know it, and with very little experience under my belt. I worked days in a boring office and on weekends I went out looking for something I myself never quite managed to understand.

That night I had gone out drinking with some coworkers. I had more than I should have, ended up alone, and drove home slowly, with the window down and my body still hot from the alcohol and from wanting. It was hot, one of those sticky nights when the city seems unwilling to go to sleep. On other occasions I had already pulled over to hire some woman off the street, those quick escapes to relieve myself and go back home as if nothing had happened. It wasn’t something I was proud of, but at that age you follow desire more than reason, and I had a lot more wanting than common sense.

I was driving along a wide avenue near the San Telmo neighborhood, where at those hours there were always girls standing under the streetlights. I slowed down. And then I saw her.

I wouldn’t know how to describe her exactly, but something about her pinned me to the seat. She was leaning against the wall of a closed shop, wearing a short dress and with her long hair falling over one shoulder. The orange light of the streetlamp traced the curve of her leg and the shine of her lips. She looked straight at me, without hurry, as if she already knew I was going to stop. Something about that confidence appealed to me as much as it intimidated me. I rolled the window down a little more and we made a deal in a few words, in that half-whispered tone people use for those things. She got into the car with a natural ease that took me apart, leaving behind a trail of sweet perfume that hung in the space between us.

—Do you have somewhere to go? —she asked, smoothing her dress over her thighs.

—There’s a motel two blocks away —I answered, with a steadier voice than I felt.

I drove those two blocks with my heart pounding against my chest. We got there, I asked for a room in the darkened reception, and parked the car in the closed garage. We went up. The room smelled of cheap disinfectant and the only light was from a bedside lamp with a yellowed shade.

As soon as I closed the door, she pressed herself against me. And that’s where the difference from everything I knew began.

She kissed me. She really kissed me, slowly, pushing her tongue into my mouth and barely biting my lower lip while her hands slid down my back, then my waist, squeezing my ass through my pants as if she already knew exactly how much I liked being touched there. The other times, the street girls had been dry, distant, all business, all about getting there, finishing, and rushing off. She wasn’t like that. She treated me as if we had all night and as if I mattered to her.

—Wait, leave the light low —she asked when I reached for the switch.

I didn’t think much of it. I figured it was shyness, or habit. The dim light actually seemed better to me, more intimate.

She started undressing me with a patience I had never received from anyone. She took off my shirt button by button, kissed my neck, lingered at my collarbone, drifted down over my chest leaving my skin goosefleshed and my nipples hard from the brush of her tongue. She touched me with both hands and spoke in my ear.

—You’re delicious —she whispered—. I deserved a guy like you tonight.

This isn’t like the other times.

I was lost. Every caress lit me up more. I had never felt anyone take their time with me like that, never felt someone enjoy the journey instead of rushing it. She finished taking off my pants, and when she knelt in front of me, I was already so hard it hurt.

She opened her mouth and enveloped my cock slowly and obscenely, swallowing it little by little until I was panting. Her tongue circled the head, wet and hot, and then went down again, sucking hard at the base while one hand squeezed my balls and the other traced my thigh. I felt every stroke of her saliva, every suck, like a jolt in my stomach. I buried my fingers in her hair and let myself go, breathing in short gasps, mouth open, repeating to myself that I didn’t want to come yet, that I wanted more. She would pull back just a little and then take me in again, playing with me as if she knew exactly when I was about to lose it.

—That’s it, daddy —she murmured without taking her eyes off me—. Give me that cock, I’m hungry tonight.

—Fuck… —I managed to say, my throat dry—. Don’t stop.

She drove me right to the edge and then eased off, only to come back at it, licking my glans, sucking my foreskin hungrily, making sounds around my cock until my legs trembled.

—Wait —I gasped at last—, I’m about to come like this. I want to do you.

She smiled against my skin and sat up. She started taking off the rest of her clothes, but with the light so low I could barely make out the movement of her legs, the curve of her hips, the wet sheen of her skin. She asked me to take her from behind.

—Put me on all fours —she said, and settled on her knees on the mattress, arching her back and sticking her ass out for me.

I loved that position, so I didn’t hesitate. I took a condom out of my wallet, put it on with clumsy hands from the rush, and got behind her. I ran my hand over her hip, sliding it forward to guide myself. Her buttocks were firm, warm, and the contact made me swallow hard.

And then, instead of what I expected to find, my fingers touched something else.

I froze. It took me a couple of seconds to understand what my hand already knew. There, between her thighs, there was not what I had assumed. There was a cock, hard and hot, hidden and obvious at the same time, brushing against my palm with a truth that emptied my head in one shot.

—You’re a man —I blurted out, recoiling.

—No, daddy —she answered without losing her cool, looking back over her shoulder—. I’m a trans girl, which is very different.

***

I sat on the edge of the bed with my head spinning. The alcohol, the arousal, and the shock mixed together in my stomach. I started accusing her, babbling, not really knowing what I was saying.

—You tricked me —I told her—. I don’t like men. Why didn’t you warn me? Why didn’t you tell me before I got in the car?

She sat down in front of me, not covering herself, not hiding, with a calm that threw me off even more. Her legs were spread and that cock between her thighs was tense, firm, ready, as if she didn’t care that I was looking at her.

—I didn’t trick you —she replied—. Everybody knows the girls on that corner are trans. It’s the well-known corner in the neighborhood. I thought you knew, that’s why you stopped there.

I didn’t know what to say. The truth was I didn’t know anything at all. I was a small-town kid in a huge city, looking for things I didn’t even know how to name. I went quiet, staring at the floor, feeling ridiculous and confused in equal measure.

She let the first blow pass. She didn’t come closer, didn’t insist, just waited. After a long while, she spoke again, in a low voice.

—Look, but a moment ago you were having an incredible time. You were enjoying yourself, I could feel it. What’s the problem with me? Let me take care of you and I promise you’ll like it more than you think.

I should have gotten dressed and left. That’s what part of my head told me, the part educated in fear and in what one is supposed to feel. But there was another part, one I was only just discovering, that kept remembering her kisses, her hands, the way she had made me feel desired for the first time in my life.

I stayed.

***

She came close again slowly, giving me all the time in the world to change my mind. She kissed me again, just like before, and I discovered the kiss was still good, that my body hadn’t stopped responding just because my mind had gotten scared. Her hands traced me again, warm, unhurried, and I felt the tension from the shock start to loosen in my shoulders. Little by little I let go. I let her lie me back against the pillows, let her take me in her mouth again, and this time I looked her straight in the face, no longer hiding from what was happening or what I was feeling.

When she asked if I wanted to try, I nodded without speaking. She guided me, with infinite patience, telling me how, telling me to go slowly, not to rush. I opened her legs wider, she lined the tip up between her folds and helped me enter little by little, first just barely, then deeper, while she bit her lip and whispered for me not to hold back. The friction was different, tight and wet, and every centimeter I advanced drew a moan out of me. I grabbed her by the waist, she dug her nails into my shoulders, and between the two of us we found the rhythm, first slow, then firmer, with her voice in my ear setting the beat for me.

—Yeah, fuck me like that —she panted—. Don’t be a pussy, give it all to me.

The mattress complained beneath us. I went in and out, feeling how she squeezed around me, how the wetness coated my base and made me slide better, how she offered me her ass high and firm so I could slam into her mercilessly. Every time I drove my hips a little deeper, she exhaled with a moan and asked for more, harder, deeper. I bit her shoulder, grabbed her tits with one hand while the other held her by the waist, and watched her tremble beneath me, come apart, enjoying every stroke of my cock against her body.

Then I lifted one of her legs to open her better and changed the angle; I went even deeper and felt that delicious pressure closing around me. She let out a whimper and then a short, hot laugh, as if she loved that I had finally worked up the nerve.

—Like that, like that, don’t stop —she told me—. You’re leaving me all marked up.

By then I wasn’t thinking about anything else. The arousal had my head empty and my body on fire, throbbing all over. When she turned slightly to look at me, I saw her eyes half-closed, her mouth parted, her skin damp with sweat. She asked me to squeeze her cock and I did, wrapping my hand around it while I kept moving inside her, and I felt it harden even more between my fingers. The two of us were breathing like animals, sucking air in gasps, thrusting and receiving, hips crashing together on the narrow motel bed.

—I’m about to come —I warned her, my voice broken.

—Then come inside this condom, baby —she answered—. I want to feel you finish on me.

And I came. My whole body tensed and my load exploded into the condom with such violence it made me see white. I was still holding onto her, trembling, while she kept clenching around me in those spasms that shook my waist. I stayed like that for a few seconds, catching my breath, feeling my heartbeat slowly come back down.

Then came the awkward silence, the kind that always arrives when desire goes out and reality comes back. I took off the condom, got dressed in silence, and gathered my things. She stayed lying there, looking at me with a half smile, as if she knew something about me I still wasn’t ready to admit.

I didn’t take her back to her corner. I left her at the motel door, paid her what we had agreed on and a little extra, and left without looking back. On the way home I drove with the windows open, as if the air might clean something off me.

I got home and went straight into the shower. I stayed under the water for a long time, scrubbing myself hard, trying to wash off an odor that was really not on my skin but in my head. I felt dirty, strange, guilty. I kept telling myself it had been a mistake, that it was the alcohol, that it wouldn’t happen again.

But that night, in bed with the lights off, I couldn’t stop thinking about her hands, her mouth, what I had felt. And I understood, even if it was hard to admit, that something inside me had woken up and was never going back to sleep.

I wasn’t wrong. That unknown woman on the corner, whose name I never learned, was the beginning of a taste that has stayed with me for many, many years. It took me a long time to accept it without guilt, to stop showering afterward as if I had to erase something. But that first time, clumsy and scared, is still the one I remember most fondly. Because it was the night I stopped lying to myself about what I was really looking for.