The First Time I Dressed to Give Myself to a Man

I’m thirty-one years old and I live in Medellín, although I grew up in a small mountain town. Like so many of us, my taste for women’s clothes started when I was still a boy. On vacation they would leave me at my aunt’s house, and when I was alone I’d take advantage of it to open my cousins’ drawer and try on whatever I found. I remember, with an almost shameful clarity, the first time I put on a black thong and felt it disappear between my ass cheeks. That new, forbidden sensation left me trembling in front of the mirror.

Since then, every time I had the house to myself, I repeated the ritual. I tried on dresses, stockings, padded bras stuffed with socks, and I looked at myself in profile, trying to guess at the woman I wanted to be. I grew up, moved to the city, finished school, and that desire never disappeared. It just learned how to hide better.

At twenty-one I gathered the courage to start reading those ads from people looking for hookups. Everything I read excited me, but nothing convinced me completely. The idea of going to a hotel terrified me, so I always looked for options at the other person’s place. I spent almost a whole year browsing, getting turned on, and closing the page before writing anything.

Until Marcelo appeared.

His ad was different: direct, but kind. I replied one night, my heart pounding in my throat, and told him right away that it would be my first time. I told him I wanted to do it dressed as a woman, completely. I thought it would scare him. Instead, he loved the idea and asked for photos to get to know me first.

That turned me on in a way I hadn’t expected. I had never imagined sending him photos of myself all dolled up, to a man. And then I realized something absurd: I didn’t have any clothes of my own. Everything I had worn in my life had been borrowed, stolen from other people’s drawers.

So I started looking. It took me more than I expected to find stores that sold what I wanted without making me feel watched, but in the end I got a set that seemed perfect to me: a black corset to give me a little waist — I’m of average build, neither skinny nor fat — a pair of black silicone stockings that held themselves up, and a thong in the same color.

I locked myself in my room one afternoon, put everything on, and took pictures lying on the sofa. When I sent them to Marcelo, his reply came almost instantly. He loved them. The two of us ended that conversation breathless, and agreed to meet.

***

The place we chose was a hotel in the Laureles neighborhood, one of those discreet places where nobody asks anything. Marcelo told me I could change there, that the place was open to the public and not to worry about a thing. That phrase, “don’t worry about a thing,” stayed with me the whole taxi ride, repeating itself like a mantra while my nerves twisted my stomach.

I recognized him as soon as I saw him at the entrance. He was about ten years older than me and quite a bit taller. He had a calm, confident way of moving that soothed me right away. He behaved like a gentleman from the very first moment: he handled all the check-in at the desk, asked me to wait to one side, and when we went up he opened the room door for me and let me go in first.

Inside, I was a bundle of nerves. He noticed.

—Go change at your own pace —he said—. I’ll wait here. No rush.

I went into the bathroom and started undressing slowly. Since I’ve always worn my hair a bit long, I didn’t need a wig. I put on the thong, then the corset, and finally the stockings, which are what I like most about the whole process, that feeling of the fabric sliding up my leg. I did a little makeup, with eyeshadow and lipstick I had kept for months for that day. I took a breath in front of the mirror, looked at the woman staring back at me, and came out.

Marcelo looked me over from head to toe. He said a few things that made me blush to my ears. And then he did something I hadn’t expected: he handed me a box.

—It’s for you —he said.

I opened it with trembling hands. Inside were a pair of open-toe heels, eight centimeters high, black and shiny. I almost burst into tears. I had told him how difficult it had been for me to buy my first clothes, and he had remembered that detail. I sat on the edge of the bed, still emotional, and started putting them on.

It was when I lifted my head that I realized he had already gotten naked while I was distracted with the box. He was only wearing a towel tied around his waist. And right in front of my face, exactly at eye level, the towel was lifting over a bulge that left no room for doubt.

Finally. The moment I had been imagining for years was, literally, right in front of me.

***

I looked up at him, with all the cheek I could gather.

—Take it off —he said in a low voice.

I pulled at the towel and let it fall. What appeared left me breathless. I took him from the base and my hand didn’t even reach half his length. He was bigger than anything I had ever seen, bigger than I had imagined. He moved a little closer and I could smell him, that smell of a clean, warm man that has driven me crazy ever since.

I started slowly, running my hands over him from top to bottom. Then I kissed the tip, licked him along the shaft, and little by little I began to take him into my mouth. He was the first one I had ever tasted in my life and I liked him immediately. The only problem was exactly that: being the first, and of that size, gagging was impossible to avoid.

—Easy —he said, stroking my hair—. No rush. Take your time.

And I did. We stayed like that for a good while, me learning, him guiding me patiently, until I felt more than half of him sliding in when my mouth touched my own hand. I was happy, proud of what I was managing, until he stopped me gently.

—Get on all fours on the bed —he asked.

I obeyed, expecting a caress, something. Instead I heard a click. I turned, startled, and saw him taking a photo of me.

—You’re going to like them —he said—. I promise.

I agreed, I don’t know why, maybe because in that room I felt like someone else. So I kept going. On my knees, lying on my side, with the thong pulled over to one side, I let him photograph every inch. Then, without warning, I felt his tongue between my ass cheeks and my whole body shuddered at once. I had never felt anything like it, a warm current running up my back.

He turned me over carefully and handed me a condom.

—Put it on me —he said.

I did it with my mouth, as much as I could. Then I watched him take a bottle of lubricant and ask me again to get on all fours.

***

He smeared the lubricant on me with a firm hand, without hurry, parting my ass cheeks and looking at me as if he knew exactly what he was doing to me. First I felt the coldness of the gel, then the pressure of his fingers searching for my opening. He stroked me in circles, slow, insistent, and I was already panting before he touched me for real. First one finger, slowly, barely opening me. Then two, and the stretch drew a moan from me that filled me with shame and pleasure at the same time. When he put in three, my back arched on its own over the bed, because that sweet, painful tension was driving me crazy.

—That’s it, stay still —he whispered in my ear—. That’s how I like you.

I couldn’t answer. My face was buried in the sheet, my ass held wide open by his hand, and my breathing was broken. He pulled his fingers out and I felt the brush of his tip pressing at my entrance, pushing just a little, testing. The condom was hard and hot. He held my waist and, with brutal slowness, started to enter. First the head, then a little more, and then a deeper sting that made me squeeze my eyes shut. Tears came to my eyes from the intensity of the stretch. He was huge. I felt him filling me, opening me in a way none of my fantasies had been able to anticipate.

—Does it hurt? —he asked, though he didn’t stop.

—You’re splitting me in two —I said, between gasps—. Don’t stop.

He liked that. I could tell from the way he drew in a deep breath, from the way he gripped my hip harder and kept pushing. He went in millimeter by millimeter, without jerking, letting me adjust to his size while sweat ran down my back. Every time he sank a little deeper, my cunt clenched uselessly against the mattress and my legs trembled. When he was almost all the way in, I was left suspended in a mix of sweet pain and ferocious hunger. I felt the pressure of his big cock inside me like a living presence, heavy, hot, impossible to ignore.

He started moving with short, slow strokes, measuring my body. He pulled out just a little and then slid back in, rubbing me inside in a way that made me let out filthy little moans without thinking. The sound of his skin slapping against my ass filled the room little by little, first soft, then wetter, more rhythmic. I clung to the sheet with both hands and pushed back, wanting more, offering him my ass without a hint of shame. I loved feeling him come in and out, feeling him open me with more and more confidence, feeling my body stop resisting and start asking him for the rhythm.

We turned onto our sides to change angle. He lifted one leg and held it against his chest while he kept fucking me. From there I felt him even deeper. Every thrust ripped a different moan from me, longer, more broken. He kissed my neck and spoke into my ear with that low voice that was dismantling me.

—Tell me if you want me to stop.

—No —I answered at once—. I want to feel all of you.

That answer seemed to ignite him. His hand closed harder on my waist and he started taking me with more determination, with sharp blows that made my body bounce against the mattress. I was already completely wet inside, the lubricant mixed with my own arousal, and still every thrust felt brutal. The bed creaked, my breathing turned into a continuous moan, and every now and then he stopped to look at me, as if enjoying me was part of the game too. Then he made me open my legs wider, pulled my thong aside with two fingers, and kept driving his cock into me with that dirty precision that made me more obedient.

—Look at me —he ordered at one point.

I lifted my head as best I could and saw his face twisted, focused, his mouth slightly open, his eyes fixed on me. That finished breaking me. A wave of heat rose from my belly to my throat, a shiver that left me covered in goose bumps. He kept fucking me, firm, without letting go. Now and then he pulled almost all the way out and then slammed back in, forcing me open again. I clung to him, to his rhythm, to the filthy pleasure of knowing myself used and wanted at the same time.

—I want to ride you —I said, my voice trembling with desire.

He lay back right away, breathing hard. I got myself on top, turning my back to him so I could see myself in the large mirror in the room. I took his cock in one hand and guided it to my entrance, still sensitive from before. I lowered myself slowly, feeling that delicious stretch again, and when I sat down completely on him, we both went still for a second, weighing the charge of the moment. Then I started moving.

I went up and down carefully at first, holding onto his thighs. Then faster, letting my body set the pace. The sound of my ass slapping against his pelvis grew louder, more obscene, and that turned me on even more. I could feel every internal brush, every friction of his cock against my walls, every pulse of his lost inside me. The mirror gave me back an image that looked nothing like the boy I had been: fake tits, black heels, my ass spread over a man who looked at me like he didn’t want to miss a thing.

—That’s it, like that —he said—. Ride me hard.

I obeyed. I leaned forward a little so he could grab my hips and started fucking him back with more force. The pleasure gathered down low like an unbearable pressure, a burning ball that was going to explode at any moment. I touched my own stomach, felt the corset squeezing my waist, and moaned without shame, completely surrendered. Marcelo held me from behind and suddenly made me go deeper, until I felt him hitting the bottom with every rise. The impact was so good it made me dizzy.

***

We stayed like that until he made me get off the chair and took me back to the bed. He arranged me face down, with my face buried in the pillow and my ass lifted high. From behind he started fucking me with everything he had, without the patience from before, already in full possession of my body. Every thrust made me bounce on the mattress and left me with my mouth open, letting out sounds even I didn’t recognize. The friction was so strong I felt my skin burning where my thighs met, but I didn’t want to stop. I wanted more, deeper, dirtier, more of this man splitting my ass while I came apart inside.

Then he pulled his cock out and knelt behind me. He took off the condom quickly and I felt the heat of his hand on my lower back, guiding me so I wouldn’t move. He moved my thong aside, opened me wide, and I felt the first thick drop fall onto me, warm, sliding down my slit until it stuck between my ass cheeks. Then came another, and another, until I was left marked and shining.

—You were going to warn me —I complained, still panting, with a broken little laugh of frustration—. I wanted to put it in my mouth.

Marcelo smiled, just as winded, looking at me like he knew he had left me hungry on purpose.

—That —he said— is for the second round.

And I loved that answer. I liked feeling like that, hot, used, still with his cock throbbing in my memory and his cum marking my back. I stayed there for a moment, breathing deeply, while he stroked my ass with the tips of his fingers and I understood that this first time had not only taken my virginity: it had also left me with a new way of looking at myself, of wanting myself, and of demanding from my body everything I had kept locked away for years.

***

That was my first time. I waited years for it, and it turned out better than any of my lonely fantasies had promised. I left that hotel feeling, for the first time in my life, exactly like the person I had always wanted to be. I’ll tell you another day what happened in the second round. For now, thank you for reading me. Kisses to all.