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 a broad-minded guy, the kind who laughs easily and isn’t afraid of much. A couple of years ago I started putting on lingerie at night, first out of curiosity and then because the idea of being like that, all dressed up and soft, in some man’s bed, made me tremble 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 and my cock hard, pressed against the lace of a thong that was too small for me. But I had never taken the step. I was twenty-six and still a virgin in the only way that really mattered to me: no one had fucked my ass yet.

That changed in Lisbon.

I was away on vacation by myself, far from anyone who knew me, and that distance gave me a courage I never had at home. The first night in 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: mature men, guys my age, others quite a bit younger. Among so many faces, two really caught my eye. One was a man about forty-five, with a calm gaze and a body he kept in shape; in the photos he was wearing a shirt and smiling with the confidence of someone who no longer had anything 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 never would have dared to do in my own city: I made plans with both of them. I was on vacation. I could try a little of everything.

***

With the older one, who introduced himself as Esteban, I met that same afternoon. The sun was going down when I went out for a walk, and we ended up in a little café, one of those places with wicker chairs out on the sidewalk. We talked a lot more than I expected. He had a measured voice and a way of looking at me that made me drop 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, tracing me slowly, and one of them found my groin right away, squeezing me over my pants until a short moan burst from my mouth into his. I stopped thinking. We ended up in the back seat of his car, on a side street where only the orange glow of a streetlamp could see us.

He pulled his pants down to his knees and freed a thick cock, already rock hard, with a shiny head and a vein running the length of it. My mouth watered just looking at it. I knelt in the little space there was, my knees bent against the door, and started slowly, without rushing, running my tongue over his balls first, sucking them one by one, then moving up the shaft with a long lick that drew a groan from him. I kissed his glans, teased the tip of my tongue along the frenulum, and only then took him all the way into my mouth, very slowly, until I felt him hit the back of my throat.

He breathed deeply, one hand resting lightly on the back of my neck, not pushing, letting me set the pace. I closed my lips tight around his cock and went up and down, leaving a thread of saliva running over his balls and staining his dropped pants. Every time I pulled the cock out to breathe I held it against my cheek and gave him a dirty smile, knowing he was watching me from above with half-lidded eyes.

This is what I imagined so many nights.

I enjoyed every second of having him like that, surrendered and silent, while a car passed outside without even looking at us. There was something about the age difference that I liked: the calm with which he lived everything, without hurry, as if we had the whole night. I took him back in, this time deeper, making myself gag on purpose, tears gathering in my eyes and a thick string of spit running down my chin. I changed the rhythm on purpose, prolonging it, sucking him with my mouth wide open, listening to his breathing break every time he thought he was about to come and I stopped dead, squeezing the base with two fingers so he wouldn’t finish yet.

“Fuck, girl, like that… don’t stop,” he murmured, and every word made me hotter.

I sucked his balls again, one inside my mouth and then the other, while I gave him a slow hand job with a saliva-soaked hand. His cock throbbed against my face on its own. I took him to the edge slowly and, when I whispered for him to give it to me in my mouth, he didn’t hold back. A warm stream hit my tongue, and then another, and another, until I was completely full. I swallowed almost all of it, let a little drip deliberately from the corner of my mouth, and cleaned the tip with my tongue, not letting go until the last drop was gone. Then he kissed my forehead, almost tenderly, still tasting his load in my mouth, and helped me fix my clothes.

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

I went back to the hotel still burning, with his semen still warm on my palate and the feeling of what had just happened sunk into my skin. I hadn’t gotten undressed, hadn’t gone any further, but something had opened inside me. And that same night I had another date.

***

I met Darío later. Before leaving, I carefully folded my best lingerie set — a black one, with stockings that clipped to the thigh — and put it in a bag. I wasn’t going to break it in just anywhere.

We started at a pool hall downtown. He played well and I pretended I knew what I was doing, laughing every time I deliberately missed a shot. He had a different energy from Esteban’s: more direct, more impatient, as if he already knew how the night would 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 locked on my ass. He didn’t even try to hide it. He’d come closer under the pretense of correcting my aim, rest his hand on my hip, and once he slid it shamelessly between my cheeks over my pants, squeezing just enough to make a sigh slip out of me. I let him do it. All the tension I’d held back for years concentrated that night in my neck, in my throat, in the need for this to stop being a game and for him to fuck me already.

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 something pretty on for you.”

He looked up and his smile widened.

“Something pretty?” he repeated.

“Something I’ve never shown anyone.”

He never touched the table again. He set down the cue and paid without waiting for change. In the taxi he pressed my hand against his bulge all the way there, and under the fabric I could feel a hard, long cock already standing diagonally against his thigh. I squeezed him over his pants and he let out a rough laugh. I had told him, in earlier messages, that no one had ever penetrated me, that this would be my real first time. Far from scaring him off, it seemed to turn him on even more.

“I’m going to tear that virgin little ass apart,” he whispered in my ear. “I’ve been thinking all day about how tight your cunt is going to feel around my cock.”

I bit my lip and pressed my thighs together.

***

The room had warm lighting and a big bathtub by the window. The first thing I did was lock myself in the bathroom to change. I put on the black set, the thigh-high stockings with the straight seam, the lace thong that barely held in my cock, pushing it upward, and I painted my lips red. When I came out, he was already on the bed, reclined, in nothing but boxer briefs, and you could tell how aroused he was just by looking at him: the fabric tented up and a dark stain of pre-cum marking the tip.

He ran his eyes over me from head to toe and stayed silent for a whole second.

“Come here,” he said at last, in a lower voice. “Come here, princess.”

I lay down beside him. He started kissing me slowly, lingering on my neck, while one hand slid down my back to rest on my ass over the thong. He gave me a soft slap, then a harder one, and each one pulled a sigh from me I couldn’t control. His free hand squeezed the bulge under the lace, feeling how hard I was too, and he smiled against my neck.

“Look at you, already soaked,” he murmured, and ran his thumb over the wet stain my own cock had left on the fabric.

I was already hot before touching him; now I was on the verge of begging. I yanked his boxer briefs down and his cock sprang free, thick, with a pronounced curve upward and heavy balls hanging underneath. I stared at it for a second before lunging.

“Turn around,” he asked later, after I’d run my tongue over the whole thing twice already. “I want to see you from behind.”

I obeyed. I got on my knees with my face against the mattress and my ass raised, and he slowly pulled my thong down, leaving it tangled halfway down my thigh, over my stockings. First I felt his hands spreading my cheeks apart and then his mouth right there, his tongue hot and broad licking me from top to bottom, circling my entrance, pressing in. I had to bite the pillow to keep from screaming. He ate my ass with obscene patience, coating me with spit, forcing his tongue in hard, alternating with long licks that ran up my perineum to my balls.

I had never imagined something like that could feel that way, that mix of shame and pleasure that made me arch, desperate for more, pushing my ass back into his face. One of his fingers slipped in with all that saliva and opened me slowly, moving in circles, searching inside. Then there were two.

“So tight, fuck,” he said, and slapped me again, making me tremble.

Then he settled himself and offered me his cock in my mouth. I took it eagerly, turned to the side, letting him set the rhythm, fucking my throat slowly at first and then deeper, gripping my hair. He’d pull it out, smack my face with it, rub it over my lips and shove it back in. I sucked him until his balls were hard and taut against his body. 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, mouth open and tongue out, feeling him come in thick bursts inside, hot and heavy, swallowing and swallowing again. Then I cleaned him slowly with my tongue, gathering every last drop left shining on the tip, while he looked at me with a smile of disbelief.

What was most surprising was that he didn’t stop there. Far from going soft, his cock stayed hard, red, throbbing against his belly. He seemed even more aroused than before.

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

I nodded, though my heart was hammering out of my chest.

***

He put me on all fours on the bed. He took a little bottle of lubricant from the bedside table and squeezed a good amount onto his fingers. He took his time, preparing me patiently, with spit and careful fingers, one first, then two, then three, opening me with scissors inside until I stopped tensing and started moving my ass on my own, looking for more. He put on a condom, coated his whole cock with lubricant until it shone, and rested the head of his glans at my entrance.

“Breathe,” he said, and pushed.

When he finally started going in, he did it so slowly I almost didn’t notice the exact moment I stopped being a virgin. I felt the pressure, then the brief burn, and then the thick head sliding past the ring and sinking inside. A long moan escaped me into the sheets. He kept going in centimeter by centimeter, stopping now and then, until I felt his balls pressed against mine.

He stopped fully inside for a few seconds, giving me time to get used to it. I was breathing in short gasps, gripping the sheets, feeling every centimeter as something entirely new, a hot fullness throbbing inside me.

“Good?” he whispered.

“Don’t stop,” was all I could say. “Fuck me.”

He didn’t stop. He started moving, first slowly, pulling almost all the way out and pushing back in again at a pace that made me watch his cock disappear inside me each time, and then more forcefully, gripping my hips, driving in with a sharp thrust that made my teeth click together. I discovered that it was better than anything I had fantasized about in the solitude of my room. My own cock was rock hard, dripping on its own onto the sheet without anyone having to touch it.

“Look at you, leaking all on your own,” he laughed behind me, and slapped my ass again. “You like getting fucked, huh, slut?”

“Yes… yes, harder,” I begged him.

And he gave it to me harder. He had a way of doing it that drove me crazy: sometimes he pulled out completely, made me turn my head, and shoved his cock into my mouth so I could taste myself, and a moment later he was around me again, burying it in from behind with one single thrust. That alternation, that back-and-forth from ass to mouth, had me completely at his mercy, drooling, with smeared mascara and lipstick rubbed all over his cock.

He tried me in several positions. He put me on my back, with my legs bent against my chest and the stockings cutting into my thighs, and fucked me looking me in the eyes, watching the moans slip out of me and my cock bouncing against my own belly with every thrust. Then he sat me on top of him and made me ride him, his hands on my chest, letting me go up and down on my own, impaling myself completely each time, while he groped my ass and spanked me to set the rhythm.

The last one was standing, against the wall, with me spreading my cheeks apart with my own hands so he could get all the way in. He drove it all the way home in one shot and stayed inside, moving his hips in circles, grinding me from the inside, pulling broken gasps from me. I didn’t want it to end. I felt as if that whole fantasy I’d kept locked away for years was becoming real all at once, 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 while, breathing hard and slowly pulling out, shining all the way to the base.

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

He took off the condom. I knelt in front of him with my tongue out, grabbing his balls with one hand and offering my face like a cup. He jerked himself slowly, with his cock a finger’s width from my lips, brushing my cheek, tapping me with it, teasing me, until I felt the first warm drops fall onto my tongue. Then came the stream, long and powerful, painting my lips, my nose, my chin. I swallowed what would fit in my mouth and took it all, without moving away, until the very last drop. I licked the tip so I wouldn’t lose any and looked up at him with my face smeared with semen and a smile. Then I sat beside him, both of us out of breath, 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 way, there was still time for a slow goodbye under the sheets: he woke me by sliding his cock between my cheeks, already lubed up, and came at me from behind on his side, with my leg lifted over his, fucking me slowly, almost lazily, until he came inside the condom with his mouth pressed to the back of my neck.

We bathed in that huge tub by the window, with the city waking up outside. He sat me astride him in the water and put it in me once more, while I moved only a little, and he stroked my cock beneath the foam until I came over his belly. We barely talked. There was no need.

Darío and I stayed in touch for a while, messages 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 and pull down my thong to give myself a slow hand job, I don’t imagine just any hands anymore. I imagine that night in Lisbon, Darío’s cock sinking into me for the first time, and Esteban’s shooting in my mouth in the seat of that car, the first time I stopped dreaming it and finally lived it.