My Debut as a Cross-Dresser on the Busiest Corner

My name is Vanesa, and for a long time I had been carrying around a fantasy that wouldn’t let me sleep. It wasn’t the first time I’d sold sex; I had done that before. I’d advertise myself on social media, exchange messages, meet the client, and see each other straight at a motel, everything discreet, everything controlled. But what really kept me up at night was something else. I wanted to stand on a street. I wanted to feel the cold asphalt under my heels, the lights of the cars sweeping over me from head to toe, and the gaze of strangers sizing me up from their windows.

I’m tall, thin, with a good body and a back I like to show off in tight clothes. I knew exactly the image I wanted to give that night, and for weeks I kept refining it in my head until I knew it by heart.

One night, without telling anyone, I decided I was ready. It was almost eleven. I packed my bag with everything I needed, ordered a car, and went to a transient motel in an area I knew well. I wanted to get ready there, leave from there, and, if everything went the way I had imagined, come back there with whoever it was.

In the room I took my time. I put on a body-hugging black dress, one of those that forgive nothing, and a pair of silver high-heeled shoes that shimmered in the light like two beacons. Underneath, a black string thong. I adjusted the long, straight wig, styled with a center part, lined my eyes carefully, and finished with a deep red lipstick that made me feel like someone else. A small black purse, and nothing more. I looked at myself in the mirror and for a second I didn’t recognize myself. It was her. It was who I wanted to be that night.

This is really me, I thought, and smiled.

***

I left the motel and walked to a wide avenue, one of the busiest in the city, where cars never stop passing even after midnight. The night air raised goosebumps on my skin the moment I stepped out. I positioned myself on a corner, under a streetlight, and stayed there, standing still, my heart pounding in my throat.

The adrenaline was immediate and brutal. I was really doing it. After months of imagining it, I was standing right there in the middle of the street, in full view of anyone, offering myself with no protection but the night. I felt every car that passed like a caress and a threat at the same time. Some slowed down. Others turned their heads and kept going. A pickup truck honked and the people inside shouted something at me I couldn’t make out, but the gesture alone made me burn inside.

I don’t know how long I stood there like that, exposed, feeling desired by complete strangers who would never know my name. It was exactly what I had been looking for. Every glance that swept over me confirmed that I was there, that it was real, that I was daring to do it.

I thought about all the nights I had spent in front of the mirror practicing that same pose, about the times I had backed out at the last minute and crawled back into bed with the fantasy still intact and the desire only half satisfied. Now there was no turning back. The cold asphalt, the distant hum of the avenue, the damp smell of the night: everything was new, everything electrified me.

I leaned against a pole and crossed one leg over the other, letting the light fall all over me. I knew that from the cars you could see the silhouette well, the shine of the heels, the curve of my hips under the dress. I felt dangerous and beautiful at the same time, owner of something I had only ever imagined in secret for years.

The first one to stop was a man in a dark sedan. He lowered the window just a crack and asked me how much. I gave him a price. He stared at me for a few seconds, hesitated, looked in the rearview mirror as if afraid someone might see him, and in the end shook his head and drove off. I watched him leave and, instead of disappointment, I felt a kind of game. There would be more. The night had only just begun.

I adjusted my hair again and waited. Several more cars passed, some slow, others indifferent. An empty taxi slowed down, the driver looked at me for a long moment, and kept going. Every time one of them braked even a little, my breath caught in my chest.

***

The second one really stopped. It was a gray pickup, neither new nor old. The man lowered the passenger-side window and beckoned me over with his hand. I walked up to the window moving slowly, knowing he was looking at my legs, my heels, the curve of my back.

—How much? —he asked.

—Five hundred —I said.

He scratched his chin and twisted his mouth.

—I’ve got three hundred —he said. —That’s what it is.

On another night I might have bargained, or let him go. But by then I was already turned on, set on fire by everything that had happened before, by the waiting, by the looks, by the simple fact of being there standing. The money almost didn’t matter. What I wanted was to live the full fantasy.

—All right —I said, and opened the door. —Let’s go.

I got in, told him the motel where I was staying, and he started the car. On the way we hardly talked. He drove with one hand and with the other squeezed my thigh over the dress, slowly moving higher, testing me. I let him, watching the avenue lights race backward through the window, feeling more like a whore and more free with every block.

I didn’t even ask his name. I didn’t care. He was a stranger, and that was exactly what I needed him to be.

***

We went into the room and I locked the door. The light was dim, orange, perfect. He set the keys and wallet on the little table and began undressing without ceremony, like a man who knew why he was there. I watched him do it, still in my dress and heels, enjoying the contrast between him, already naked, and me, still put together from head to toe.

I knelt in front of him. I started slowly, with my mouth barely brushing him, licking softly, playing with my tongue while I listened to his breathing get heavier. I felt him harden little by little between my lips. I took my time, going down to the base, coming back up, controlling the rhythm, looking up at him to see his face.

—Like that, slowly —he murmured, his hand tangled in my wig.

I kept sucking him until he was completely hard, until his breathing turned into a steady pant and I knew he was ready. I wiped my mouth with the back of my hand and stood up.

—Get on all fours —he said, his voice hoarse.

I took off my thong, left my dress hiked up, and got onto the bed on my elbows and knees, my heels still on. I pulled the lubricant out of my purse and got ready, feeling the cold gel make me shiver. He came up behind me and began to rub against me, sliding in slowly, without hurry, letting me feel every inch.

—I want to do it to you like this, with nothing —he said, and it wasn’t a question.

—Do it —I answered, because that was exactly what I wanted too.

He held my waist with both hands and pushed. I felt him enter all the way, hot, with no barrier between us, and a long moan escaped me that I didn’t try to hold back. It was the fantasy made flesh: a stranger, in a transient motel, after I’d stood on a corner the way I had dreamed of for so long. I didn’t know his name and I didn’t care in the slightest.

—You’re a whore —he told me in my ear, setting the pace.

—I’m your whore tonight —I answered between gasps.

He started moving harder and harder, gripping me, and I followed his rhythm, rocking back to feel him deeper. Hot skin, the sound of our bodies, his broken breathing against my nape. I closed my eyes and let myself go completely, feeling used and desired at the same time, which was exactly the mix I had been after.

I could stay like this forever, I thought, lost in the sensation.

—Say dirty things to me —he asked.

And I did. I told him everything I knew would turn him on, I played along with his dirtiest fantasies, in that game of words that had nothing real about it but lit both of us up. The more I talked to him, the harder he moved, until the rhythm turned frantic and I knew he was close.

***

—Where do you want it? —he managed to ask, barely out of breath.

—Inside —I said without hesitation. —Stay inside.

He held me tight, pushed all the way in, and stayed there, trembling, while he finished. I felt him come, hot, collapsing a little over my back with ragged breathing. We stayed like that for a few seconds, still, both of us panting, until he slowly pulled away.

I let myself fall onto my side on the bed, my heart still racing. He sat on the edge, catching his breath, and then got up to look for his clothes. There was no conversation, no promises, no phone numbers. They weren’t needed. He took the three hundred out of his wallet, left them on the little table, gave me one last look, and walked out of the room.

I stayed alone in the room, staring at the ceiling, still wearing my heels and with a huge smile I couldn’t wipe off my face. I had done it. After months of imagining it, I had stood in the middle of the street, been watched, desired, chosen. I had lived out the exact fantasy it had taken me so long to gather the courage to experience.

That night I learned something about myself that I could no longer ignore: that I loved the street, the exposure, the risk, the idea of not knowing which stranger would be the next to stop. I went back to the motel and took a long shower, thinking that it wouldn’t be the last time. And it wasn’t. But that one, the first, the one of my debut under the avenue lights, is the one I will never forget.