What I Discovered Dressed as a Woman in That Hotel

My name is Matías, though when I dress as a woman I prefer to be called Lucía. I’m an open-minded guy, the kind who laughs easily and isn’t afraid of much. A couple of years ago I started wearing lingerie at night, first out of curiosity and then because the idea of being like that, dressed up and soft, in some man’s bed, made me shake with pure anticipation.

For a long time, that was all it was: a fantasy that stayed between the sheets of my own room. I tried on stockings, looked at myself in the mirror, imagined hands that weren’t mine, and fell asleep with my heart racing. But I had never taken the step. I was twenty-six and still a virgin in the only way that truly mattered to me.

That changed in Lisbon.

I was on vacation alone, far from anyone who knew me, and that distance gave me a courage I never had at home. The first night at the hotel I downloaded one of those apps for finding casual company. I wasn’t expecting much. Within minutes my screen was full of messages.

There was everything: older men, guys my age, others quite a bit younger. Among so many faces, two really caught my attention. One was a man of about forty-five, with a calm gaze and a body he took care of; in the photos he was wearing a shirt and smiling with the confidence of someone who had nothing left to prove. The other was Darío, a dark-haired guy with broad shoulders and a smile that looked like a challenge.

I couldn’t choose, so I did something I would never have dared to do in my city: I made plans with both of them. I was on vacation. I could sample a little of everything.

***

I met the older one, who introduced himself as Esteban, that same afternoon. The sun was setting when I went out for a walk, and we ended up in a small café, one of those places with wicker chairs out on the sidewalk. We talked a lot more than I had expected. He had a measured voice and a way of looking at me that made me lower my eyes.

“You’re nervous,” he said, and it wasn’t a question.

“A little,” I admitted. “I don’t usually do this.”

“Then we’ll do it at your pace.”

We kissed when we said goodbye, and that kiss lasted longer than either of us had planned. His hands slipped under my coat, stroking me slowly, and I stopped thinking. We ended up in the back seat of his car, on a side street where the only witness was the orange light of a streetlamp.

He pulled his trousers down to his knees. I knelt in the small space there was and started slowly, without rushing, running my tongue over everything in front of me before daring to do more. He breathed deeply, one hand barely resting at the back of my neck, not pushing, letting me set the pace.

This is what I imagined so many nights.

I enjoyed every second of having him like that, surrendered and quiet, while a car passed outside and didn’t even look at us. There was something about the age difference that I liked: the calm way he lived it all, without hurry, as if we had the whole night. I sped up and slowed down on purpose, stretching it out, listening to his breathing crack every time he thought he was about to finish and I stopped.

I brought him to the edge slowly and, when I whispered for him to give it to me, he didn’t hold back. Afterward he kissed my forehead, almost tenderly, and helped me straighten my clothes.

“Let me know if you want to do it again,” he said.

I went back to the hotel still burning, with the warm sensation of what had just happened under my skin. I hadn’t gotten undressed, I hadn’t gone any further, but something had opened inside me. And that very night I had another date.

***

I met Darío later. Before leaving, I carefully folded my best lingerie set — a black one, with stockings held up by garters — and put it in a bag. I wasn’t going to debut it just anywhere.

We started out at a pool hall downtown. He played well and I pretended I knew how, laughing every time I missed a shot on purpose. He had a different energy from Esteban’s: more direct, more impatient, as if he already knew how the night was going to end and was just waiting for me to say it first.

Every time I bent over the table to line up a shot, I felt his eyes fixed on me. He made no attempt to hide it. He would come closer under the pretense of correcting my shot, rest a hand on my hip, and linger there a little longer than necessary. I let him. All the tension I had held in for years concentrated that night in my neck, in my throat, in my desire for it all to stop being a game.

I was the one who said it.

“What if we get a hotel?” I blurted out while he lined up the next ball. “One with a jacuzzi. I’d like to put on something pretty for you.”

He looked up and his smile widened.

“Something pretty?” he repeated.

“Something I’ve never shown anyone.”

He didn’t go back to the table. He put down the cue and paid without waiting for the change. In the taxi he squeezed my hand the whole way, and I could feel my pulse in my throat. In messages earlier, I had told him I had never been penetrated, that this would be my first real time. Far from scaring him, it seemed to turn him on even more.

***

The room had warm lighting and a large bathtub by the window. The first thing I did was lock myself in the bathroom to change. When I came out, he was already on the bed, stretched out in his boxers, and you could see how turned on he was just by looking at him.

He took me in from head to toe with his eyes and stayed silent for a full second.

“Come here,” he said at last, his voice lower.

I lay down beside him. He started kissing me slowly, lingering at my neck, while one of his hands slid down my back to settle on my ass. He gave me a soft spank, then another, and each one drew out a sigh I couldn’t control. I was already hot before I touched him; now I was on the verge of begging.

“Turn over,” he asked. “I want to see you from behind.”

I obeyed. I felt his mouth travel over the small of my back, then lower, and I had to bite the pillow to keep from making too much noise. I had never imagined something like that could feel this way, that mix of shame and pleasure that made me arch my back and seek more.

Then he settled in and offered me his body. I took him eagerly, letting him set the rhythm, moving only as much as I needed to. At one point he warned me he was close and asked me not to pull away. I didn’t. I stayed with him until the end and cleaned him off afterward, slowly, with my tongue, while he watched me with an incredulous smile.

What was most surprising was that he didn’t stop there. Far from coming down, he seemed even more excited than before.

“Ready?” he asked, and I knew what he meant.

I nodded, even though my heart was pounding out of my chest.

***

He put me on all fours on the bed. He took his time, preparing me patiently, with spit and careful fingers, until I stopped tensing up. When he finally started to enter me, he did it so slowly that I almost didn’t notice the exact moment I stopped being a virgin.

He stopped all the way in for a few seconds, giving me time to adjust. I was breathing in short gasps, clutching the sheets, feeling every centimeter as something entirely new.

“Okay?” he whispered.

“Don’t stop,” was the only thing I could say.

He didn’t stop. He started moving, first slowly and then with more determination, and I discovered that it surpassed anything I had fantasized about in the solitude of my room. He had a way of doing it that drove me crazy: sometimes he pulled out and made me turn my head to use my mouth, and an instant later he’d take me from behind again. That alternation, that back and forth, had me completely at his mercy.

He tried me in several positions. The last was standing, me pulling my ass cheeks apart with my own hands so he could get all the way in. I didn’t want it to end. I felt as if all that fantasy I had kept locked away for years was suddenly becoming real, in a hotel room in a city that wasn’t mine, with a man I hadn’t even known on Monday.

“Want more in your mouth?” he asked after a good while, his breathing ragged.

“When you’re ready, let me know,” I answered.

I knelt in front of him. He jerked himself slowly, brushing against my face, teasing me, until I felt the first warm drops on my tongue. I took all of him, without pulling away, every last drop. Afterward I sat beside him, both of us breathless, laughing like two people who had just shared a huge secret.

***

We slept together that night. The next morning, before each of us went our separate ways, there was still time for a slow goodbye under the sheets, without hurry, as if we wanted to stretch out a little longer something we knew wouldn’t happen again.

We bathed in that huge tub by the window, with the city waking up outside. We hardly spoke. There was no need.

Darío and I stayed in touch for a while, messages every now and then, photos, some promise neither of us kept. We never saw each other again. But sometimes, when I put on lingerie in front of the mirror in my room, I no longer imagine just any hands. I imagine that night in Lisbon, the first time I stopped dreaming about it and finally lived it.