The Night I Dressed as a Woman for a Stranger

I was already a grown man when I finally found the courage to do it. I had wanted it for years, now and then, in silence, like someone keeping a key he didn’t dare use. I had no experience of any kind, except for that time on the city subway, during a blackout, when a stranger took advantage of the darkness and the crush of bodies to put his hand down the back of my pants.

I didn’t push him away. That was the part I found hardest to admit afterward. I felt his open palm on my ass, squeezing it through my pants, and instead of bothering me, my cock turned rock-hard within seconds. He noticed and lowered his hand until it brushed against my fly, feeling the bulge showing through. While the car remained dark, I imagined him pulling me out of there, taking me to some random room, pulling down my pants, and sinking his dick all the way inside me without saying a word. When the lights came back on, we both stared straight ahead as if nothing had happened. But I already knew it was only a matter of time before a man really fucked me.

That wasn’t the first sign, of course. The first had come much earlier, one afternoon during a soccer game on the neighborhood field. We didn’t have jerseys, so the opposing team played shirtless. One of them, tall and broad-shouldered, ran sweating beneath the sun, and I felt a strange knot in my stomach every time he came near. I didn’t understand what the feeling was, only that it was nothing like what I felt for girls.

And then there was the other thing, the thing nobody knew about. One night, almost by accident, I shaved my legs in the shower. Running my hand over that smooth skin felt so good that I soon began dressing in secret: an old skirt I found, some stockings, whatever fell into my hands whenever the house was empty. I would look at myself in the mirror and not recognize myself, and that was exactly what turned me on. Sometimes I ended up with the skirt pulled up to my waist, grinding my cock against the mirror, imagining a stranger fucking me from behind while I wore my stockings.

***

A long time passed between the subway incident and the moment I decided I no longer wanted to keep it confined to my imagination. I wanted a man to really fuck me, to open my ass with his dick and make me come like I never had by myself. I placed an ad on one of those classified sites, without beating around the bush: I confessed that I had never done it, that I was looking for someone patient for my first time, that I wanted him to fuck me and treat me like a whore. I was determined to meet the first man who sounded even reasonably normal.

His name was Damián, or so his profile said. We chatted for a couple of nights. He wasn’t much of a talker, but he didn’t pester me for pictures or push me to hurry, and that gave me some confidence. We agreed to meet on a Thursday, late at night, in a quiet square near his home.

I arrived fifteen minutes early and paced around the fountain, my heart pounding in my throat. I didn’t know what to expect. Every time a man passed by, I thought that’s him, that’s him, and my mouth went dry. When he finally appeared, we recognized each other at once by the clothes we had described. He was older than me, with a short beard and a calmness in his eyes that reassured me and made me even more nervous at the same time.

“Shall we walk?” he said, just like that.

“Yes,” I replied, and my voice came out higher than I wanted.

We went to his building in silence. It was night and the street was almost empty, so nobody noticed the bulge showing through my pants with every step. I kept my eyes on the ground, counting the paving stones so I wouldn’t think too much about the cock I was going to suck in a matter of minutes.

***

His apartment was small and tidy. He put on some quiet instrumental music and poured us two glasses of red wine. I held mine with both hands so he wouldn’t notice them shaking. I was too nervous to make conversation, but I needed to hear something to anchor me, so I asked him the only thing that came to mind.

“Have you… done this before? With men, I mean.”

“I’m no expert,” he replied with half a smile. “But yes, I’ve fucked several. Relax. We’ll go slowly, at your pace. Tonight I’m going to open you up properly, so don’t worry.”

I nodded and took a long drink. The heat of the wine went down my chest and loosened the knot a little. He looked at me patiently, as if we had all night, which was exactly what we had.

Then he stood, went into the bedroom, and returned with something folded in his hands. It was a dress, one of those cheap ones sold at street stalls, made of shiny fabric with loose stitching. He placed it on the sofa beside a pair of low-heeled plastic shoes, worn at the toes.

“I want you to put it on,” he said. “If you’re up for it.”

My breath caught. I hadn’t told him about dressing up, about my secret afternoons in front of the mirror. It was as if he had guessed the secret I found hardest to say aloud. I took a second too long to answer, and that second said everything.

“All right,” I murmured.

***

I changed right there, turning my back to him at first, until modesty became absurd. The dress was tight in all the wrong places, and the heels made me take awkward little steps, but when I put them on, something inside me settled into place. For the first time, I felt exactly as I had imagined myself on those lonely nights.

“Here,” he said, handing me a feather duster. “Tonight you’re the housemaid. What’s your name?”

I understood at once. It was a game, a role, and it gave me permission to be someone else.

“Marina, sir,” I said, lowering my eyes.

“Good, Marina. There’s dust on those shelves.”

I began dusting the furniture, pretending to do my job, feeling him watching me from the sofa. Every time I stretched or bent over, I knew his eyes were following the movement of the dress. The fabric brushed my thighs, and I, who had never done anything like that in front of another person, discovered that shame and desire were the same current running down my back. Beneath the dress, my cock was completely hard, pressed against the fabric, and a drop of precum had already stained my underwear.

I bent down to clean the lower part of a shelf. I felt his hand before I heard him stand. He placed his palm on one cheek of my ass, over the fabric, and I remained motionless, saying nothing, pretending to continue with my task. He didn’t speak either. He slowly raised his hand, lifted the hem of the dress, and began running it along my legs, moving upward until it brushed my ass over my panties.

“Tell me, Marina,” he said in a low voice, very close to my ear, “does your boyfriend like your legs like this, with all that manly hair?”

“I don’t have a boyfriend, sir,” I answered, staying in character, my voice uneven. “I’m a virgin.”

“A virgin maid.” His hand stopped high on my thigh, squeezing the flesh, while with the other he felt my hard cock through the fabric. “That needs to be fixed. But first I want you to shave your legs. Now.”

***

I obeyed without thinking. I went to the bathroom with my heels clicking on the floor, stepped beneath the shower with the dress pulled up to my waist, and wet my legs with warm water. I took his razor and some soap and shaved them as quickly as I could, my hand trembling with pure anticipation. My cock stood hard against the wet fabric of the dress, and I couldn’t stop thinking that in a few minutes this man was going to fuck me.

I ran my palm over the freshly shaved skin and shivered all over. That smoothness was a promise. For a moment I looked at myself in the fogged mirror: the makeup I wasn’t wearing, the dress clinging to my wet skin, the face of someone who was finally about to do what he had been putting off for years. I left the bathroom with my legs gleaming and my chest heaving.

He was waiting for me standing beside the bed, already naked from the waist down. His dick was out, hard and thick, its veins prominent, its red head pointing straight at me. My mouth went dry when I saw it. It was the first other man’s cock I had ever seen at such close range, and it was bigger than I had imagined. He held out his hand, and I took it, unable to pull my eyes away from his dick.

“Come, Marina,” he said. “Kneel. I want you to suck me first. Learn how to use that mouth.”

I lowered myself to the floor with my heels still on, feeling the carpet beneath my knees. He stepped forward and brought his dick to my face. I grasped it awkwardly, and the weight of that hot piece of flesh surprised me. I stuck out my tongue and ran the tip over his glans, tasting him, and the salty flavor of precum filled my mouth. I heard his sigh, and it encouraged me.

“Open wide,” he murmured.

I opened my mouth, and he pushed it in slowly. I felt it sliding between my lips, warm and hard at the same time. The tip touched the roof of my mouth, and I began sucking as best I could, moving my tongue beneath it, squeezing it with my lips. He grabbed the back of my head with one hand and began setting the pace, pushing my head forward and back.

“That’s it, slut. Suck it properly. Use your whole tongue.”

I obeyed, drooling, my eyes filling with tears whenever he pushed it too deep. When the tip touched my throat, I gagged, but he pulled it out at once and let me breathe before pushing again. A strand of saliva ran down my chin and stained the dress, and instead of feeling disgusted, I was harder than ever. I sucked him for what seemed like an eternity, until he yanked his cock out with a grunt and lifted me by the shoulders.

“Enough, or I’ll come in your mouth. And tonight I’m going to fuck your ass.”

***

He led me to the mattress, laid me down carefully, and finished undressing. Then he pulled down the straps of my dress and began caressing my chest with his fingertips, drawing slow circles over my nipples until they grew hard and sensitive.

“I love your tits,” he said, playing along with the fantasy as he pinched one hard. “They’re so soft. So girlish.”

He lowered his mouth and sucked my nipples one after the other, nibbling them, while his hand slipped between my legs and gripped my hard cock beneath the dress. He began stroking it slowly without stopping his attention to my chest, and the first real moan of the night escaped me.

“Look how hard you are, little slut. All hard for your master.”

I let him do whatever he wanted, completely surrendered. Every caress drew a sigh from me, and I no longer tried to hide them. I let him strip me completely, let his mouth travel over my neck, chest, and belly, while I clung to the sheet, not knowing what to do with my hands. When he reached the bottom, he pulled my legs open and stared at my shaved ass with a dark smile.

“Bring your knees to your chest. Open up for me.”

I did it, ashamed and aroused in equal measure, feeling more exposed than ever. He spat on my hole, and the warm thread of saliva running down my crack made me tremble. Then he buried his tongue there without warning, and I cried out muffled against the pillow.

“Oh, God…” I gasped.

“Shut up and enjoy it.”

He ate my ass for long minutes, thrusting his tongue into me, licking me, soaking me completely. Then he brought up a wet finger and slid it in slowly, all the way. It burned a little at first, but the pleasure came immediately, a new, deep pleasure that made me arch my hips in search of more. He inserted a second finger, then a third, opening me, preparing me for what was coming.

“You’re tight as a real virgin,” he whispered. “I’m going to split you in two.”

I watched him take a condom from the nightstand and put it on calmly, then pour a generous stream of lubricant over his cock and another over my ass, smearing it around with his fingers.

“I don’t want to get you pregnant,” he said, and we both laughed under our breath without breaking the spell.

***

I lay on my back. He held me by the ankles and rested them on his shoulders, opening me completely. It was an impossible moment to describe. Feeling my legs folded against his chest, his weight above me, was like crossing a line from which there was no return. It was really going to happen. A man was about to put his dick inside me and make me his.

I lowered my gaze and saw it: hard, ready, glistening with lubricant, the first cock that was going to enter my ass. I watched it for a second too long, wanting to burn it into my memory, then let my head fall back and closed my eyes.

I felt the tip against my hole. I took a deep breath and tried to relax my body, to loosen everything as I had read a thousand times I was supposed to. He pushed very slowly, with a patience I thanked him for silently, and I felt him opening me inch by inch. The glans forced its way against the ring, and for a moment I thought it wouldn’t go in; then, suddenly, I gave way, and the head slipped inside me. I let out a long moan caught between pain and pleasure, clutching the sheets.

“That’s it,” he whispered. “Easy, Marina. The tip’s in. Hold on.”

He remained still, letting me breathe, and then began pushing farther, very slowly, sinking his cock into my ass inch by inch. Every inch brought a new sensation: the burning mingling with an incredible fullness, the pressure of his hot flesh forcing its way inside me. When I finally had all of him inside, his balls pressed against my ass, I felt as if I couldn’t breathe.

“All the way in,” he said. “You’re mine now, slut.”

Little by little he began moving in a slow rocking rhythm. He pulled almost all the way out and pushed back in, slowly, letting me feel every thrust. At first I tried to follow him awkwardly, until my body found his rhythm and I began lifting my hips to take him better. The burning turned into pleasure, a deep, unfamiliar pleasure that climbed my spine and made me arch my back against the mattress.

“More…” I begged, unable to believe it was my voice. “Harder, sir.”

He smiled and obeyed. He began fucking me in earnest, with harder, faster thrusts, making his balls slap against my ass. The bed creaked, the heels I was still wearing brushed against the sheets, and I moaned without stopping, moaning like a woman, like the Marina he had invented. He grabbed my hard, dripping cock and began stroking it in time with his thrusts.

“Come for me, little slut. Come with my cock in your ass.”

I couldn’t hold out for another minute. A huge spasm rose from deep in my belly, tensing my entire body, and I came in streams over my own chest, staining the half-on dress, moaning so loudly that he had to cover my mouth with his free hand. My ass clenched around his cock in waves, squeezing him, milking him, and he let out a hoarse grunt.

“Oh, fuck, yes, just like that…”

He dug his hands into my hips and drove into me with everything he had, five, six, seven more times, until he buried himself one last time all the way to the hilt and stayed there, trembling. I felt him come inside the condom, pulsing inside me, panting over my chest as if his life depended on it.

I don’t know how long it all lasted. Time became elastic, made of his quickening breath and my own moans, which I no longer recognized as mine.

***

He pulled out carefully, and I felt the strange emptiness his cock left behind as it slipped out of my open ass. He removed the condom, tied it off, threw it in the trash, and collapsed beside me. I turned toward him, still breathless, my semen cooling on my belly, and then he did the one thing we hadn’t done all night: he kissed me on the mouth. Slowly, with his tongue, without masks or role-playing. It was also my first kiss with a man, and it turned out to be what affected me most of all.

We stayed like that for quite a while, tangled in the sheets, without saying much. I got rid of the stained dress, and the heels lay beside the bed like two silent witnesses. At some point during the early morning, he fucked me again, this time doggy-style, more slowly, and made me come a second time with my face buried in the pillow. We spent the entire night in his apartment, and at dawn I dressed in my own clothes, my ass still burning, and left before he had fully woken.

I never learned his real name. I never saw him again. But that night stopped being a fantasy locked away with a key and became something real, something nobody could take from me. And, of course, it wasn’t the last time. After walking through that door, I knew exactly what I had been looking for all along: a hard cock fucking me hard, and a man calling me a slut in my ear.