The Night I Dressed Up So He Would Make Me His

I’m going to tell how it all began, because every time I remember it my pulse speeds up and I feel that mix of shame and excitement all over again, and it doesn’t let go of me. It’s not a perfect story. In fact, it turned out quite differently from how I had imagined it for years. But it was mine, it was real, and it was the beginning of something I’m still discovering.

The secret started when I was very young. I must have been eleven or twelve. I used to look at my mother’s clothes hanging there and they seemed pretty to me, soft, forbidden. At home it was just the two of us, so the only female reference I had was right there, within reach. One Sunday afternoon I was alone and couldn’t stand the curiosity. I tried on one of her dresses in front of the hallway mirror.

I don’t know how to explain what I felt. I looked pretty. I looked different. For a moment I stopped being the shy kid who hid in his room and I was someone else, someone I liked more. I put everything away before she got home, my heart pounding, and from then on that became my best-kept secret.

I repeated that ritual every time the house was empty. I learned to calculate my mother’s schedule, to fold the clothes exactly as I’d found them, to erase any trace of perfume. Over time I stopped trying on only her dresses and started paying attention to the details: how a skirt fell, how a bra fit, the way a pair of stockings completely changed the line of a leg. It wasn’t curiosity about the fabric. It was a way of recognizing myself.

The years passed. Today I’m twenty-three, I live alone in a small apartment near the center, and I work at some boring office thing that doesn’t matter. Outwardly I’m a normal guy: average height, slim, brown skin, and a smile people say is the best thing about me. Inside, I was still carrying that secret, only now it wasn’t a childish curiosity. It had become a concrete, urgent desire, asking to come out.

For a long time I dressed alone. I bought lingerie online, with fake names and parcel delivery addresses, and tried everything on when I knew no one was going to ring the bell. I looked at myself, touched my cock over the thong until it stood hard against the fabric, shoved two fingers into my ass while imagining I was someone else. But there was always an invisible wall: the fantasy ended with me cumming into a tissue, turning off the light, and going back to being the same as always.

Until I decided to cross that wall.

***

I talked it over with myself for many nights before daring to do it. I wanted someone to see me. I wanted a man to see me dressed up and want me, not as a game, but for real. I wanted him to fuck me. I went into some messaging groups like the ones where people look for encounters with no names and no questions. I wrote an honest description of what I was and what I was looking for: a guy dressing as a woman for the first time who wanted to be treated like one.

It didn’t take long for someone to answer. He called himself Damián. His messages were direct, to the point, and that confidence of his felt attractive to me. He told me where, he told me when, and I, with my hands trembling over the phone, told him yes.

The days before the meeting were delicious torture. I couldn’t concentrate on anything. I replayed every detail of how I was going to dress in my head, practiced gestures I thought were feminine in the mirror, imagined the scene over and over. Sometimes fear won and I thought about canceling, about texting him that I’d changed my mind. But then I’d look at myself in the mirror again, with the promise of finally being seen, and desire would shut fear up.

We booked a room in a discreet hotel on the outskirts, one of those places that charge by the hour and don’t ask questions. I was supposed to get there before him. I went dressed as a guy, with the women’s clothes tucked into a backpack like contraband treasure. My stomach was tied in knots the whole way there.

The room smelled like cheap disinfectant and ironed sheets. I closed the door, put the backpack on the bed, and went into the bathroom. I’d already shaved my legs and my ass, smooth as I’d never been, and that alone made me feel different, more exposed.

I started getting dressed slowly, almost ceremoniously. The red thong first, the fabric pressing against the cock that was already getting hard just from nerves. Then the fishnet stockings, pulling them up centimeter by centimeter over my legs, feeling the fabric tighten exactly where I wanted it. The garter belt. The pink bra with a bit of padding. And finally a tight black dress that didn’t match any of the above, but it was the one I had, and honestly at that moment I didn’t care.

I put on the wig, black too, and combed the strands in front of the stained bathroom mirror. I painted my lips slowly, with a pulse that wouldn’t quite calm down. And when I looked up, I didn’t see the same old boy. I saw someone new. I liked myself so much I stood there a while staring, swiveling my hips, discovering the way I moved in the dress.

I touched my face as if to confirm that person there was me. I ran my fingers over the dress fabric, over the curve of the garter belt under the skirt, over the edge of the stockings, and higher still, until I brushed my cock pressing against the red thong. Every texture reminded me that this was really happening, that it wasn’t one of the many afternoons hidden away in my room. This time there was someone on the other side of the door waiting for me. For the first time I wasn’t hiding from anyone.

This is me. At last.

I touched the bathroom door with the idea of stepping out like a proper lady, ready for slow courtship, for kisses before anything else. That was the movie I had in my head.

***

But reality didn’t read my script.

When I came out, Damián was already completely naked on the bed, with his hard cock resting against his belly, thick, veined, the tip shiny. He looked me up and down with a smile, and I won’t lie: seeing him like that turned me on immediately. He was bigger than I expected, broad-shouldered, with that kind of man’s attitude that’s used to taking what he wants. My body reacted before my head did. My thighs tightened under the dress and I felt a wet pull in my mouth just from looking at his dick.

I was expecting the prelude. Hands on the fabric of the dress, kisses on the neck, hands tracing me slowly. I’d spent years imagining exactly that. But he had a different idea, and he made it clear right away.

—Come here —he said, patting the mattress—. Get up here.

I crawled over to the bed, feeling insecure and aroused in equal parts. The dress rode up in back and I knew my thong was showing, the garter belt, the line of my shaved ass. Damián licked his lips looking at me. He grabbed the back of my neck and planted a rough kiss on me, almost biting my painted lip, while his other hand squeezed one fake tit and then went down to grab my cock over the thong.

—Look how hard you are, little slut —he murmured against my mouth—. And dressed like this too. You’re going to be a very good little whore.

The word made me tremble. No one had ever spoken to me like that. I put my hand on his cock, feeling it throb between my fingers, thick and hot. I squeezed it and he let out a low groan. I started jerking him slowly, moving my fist from the base to the head, feeling it get even harder. I liked that. That was power. I lowered my head without thinking too much, my painted lips trembling, and took it into my mouth.

I choked on it at first. It was too much dick for a mouth that had never sucked anything before. Damián put a hand on the back of my neck and started setting the pace himself, pushing my head down until I felt the head bump my throat. Tears spilled from my eyes and my mascara ran, but I kept going. I sucked with my eyes half-closed, drooling, hearing him pant above me, feeling for the first time what it was like to have a cock throbbing in my mouth. Saliva ran down my chin and dripped onto the black dress. I didn’t care. He was using me and I liked being used.

—That’s it, whore, suck that cock good —he panted, tugging on my wig—. Let it show how much you wanted it.

He pulled his cock out of my mouth all at once, a string of spit hanging between my lips and his swollen head. For a moment I thought he was going to kiss me, that he was going to caress me, that here came the courtship I’d imagined for years. But no. For a moment I thought it was going to go the way I wanted.

—Get on all fours —he cut in.

I obeyed. I hiked my dress up to my waist, leaving my ass raised and the red thong stretched between my cheeks. I felt his thumb shove it aside, leaving my hole exposed. I heard the click of a bottle of lube and breathed. At least he was going to use some. But it was only a quick squirt on the tip of his cock, almost as a formality, without giving me a single finger, without preparing me. And almost without warning, without enough saliva, without anything to soften the moment, he shoved into me.

The burn was immediate. A sharp, searing pain that ripped the air out of me and made me grip the sheets with both hands until my knuckles turned white. I felt every inch of that cock forcing its way in, pushing, prying the ring of my ass open until it sank in to the base. A strangled cry escaped me. It was nothing like the times I, alone and calmly, had explored my body at home with my fingers and a small dildo. That had been soft, mine, controlled. This was rough, чуждо, too fast, a whole cock driven into an ass that had never had more than two fingers inside it.

He started moving hard, fast, grabbing my hips and pulling almost all the way out before slamming back in with a dry thrust. The mattress squeaked with every hit. I felt his balls slap against my shifted thong, the skin of my butt bouncing, the wig sliding to one side. He asked me to moan, to sound like a woman, to tell him I was his little slut.

—Tell me you like it, whore. Tell me you want my cock in your little ass.

And I moaned, yes, I moaned and said the words he wanted in the highest voice I could manage, but half of those sounds were discomfort I didn’t know how to name. The burn wouldn’t go away. When he changed angle and hit me where he was supposed to hit me, my own cock, flattened against the mattress over the thong, gave a strange jolt, a sting of pleasure mixed with pain that confused me even more. My head was split in two: one part registering the novelty of having a man inside me, of finally being desired, of being fucked while dressed as a woman; the other just wanted it to be over.

He sped up. He dug his nails into my hip, panting over me like an animal, and suddenly he pulled out, flipped me over roughly, and started jerking off with the tip resting against my painted lips.

—Open your mouth, open it —he growled.

I opened it. And he filled my face and mouth with thick semen, hot bursts that landed on my tongue, on my chin, on the pink bra peeking out from the dress neckline. He finished with one last whimper, rubbing the head of his cock over my lips to wipe off the last drop. I stayed still, mouth full, not knowing whether to swallow or spit. In the end I swallowed. I don’t really know why. I guess because in the movie I had in my head, the woman I wanted to be swallowed.

When he was done, he let himself fall onto his side on the bed, satisfied, completely oblivious to the fact that I had been left halfway between relief and disappointment, with my own cock still hard and throbbing in the thong and no one touching it. I got dressed in silence, took the wig off with semen still sticky at the corner of my lips, cleaned my mouth in front of the same mirror where a little while before I had felt invincible. In the bathroom, sitting on the toilet, I pulled down the thong and jerked myself off quickly until I came too, biting my lip so he wouldn’t hear me. I needed to finish that on my own.

It wasn’t how I dreamed it.

And yet, while I drove back home with the backpack once again on the passenger seat and still feeling the burn between my cheeks, I didn’t regret it. I had crossed the wall. I had let someone see me completely, dressed up, real. I had sucked a cock and had my ass fucked for the first time. Nobody could take that away from me now. What was missing, I knew then, was finding the right person.

***

Because this is where my real fantasy begins, the one I repeat in my head every night since then, while I jerk off slowly wearing lingerie.

I imagine someone who knows how to wait. A man who doesn’t get naked before I finish getting ready, but instead enjoys watching me become her. Who watches me do my makeup, who helps me zip up the dress, who chooses my lingerie with his own hands and puts it on me himself, slowly, sliding the stockings up my legs while he kisses the insides of my thighs, arranging my thong with his fingers brushing my fake pussy between my cheeks, as if he were discovering me.

I imagine long caresses over the fabric before anything else. Kisses on the nape of my neck, on my shoulders, on the line of the stockings. That he speaks to me softly, tells me I’m pretty, calls me a slut but tenderly, treats me with the delicacy that first time lacked. A real courtship, patient, where there is no hurry. That I kneel in front of him with the dress on and he lets me suck his cock at my own pace, without pushing my head, letting me taste it, lick his balls, suck the tip until he moans my woman’s name.

Then that he lay me on my back on the bed, spread my legs with the stockings still on and eat my ass with his tongue for a good while, licking me, spitting on me, slipping one finger in first, then two, until he opens me up completely. That he jerks my cock over the thong while he opens me with his mouth. That he leaves me wet, stretched, begging.

And then, only after all that, that he changes the rhythm. That he gets on top of me, looks me in the eyes, and slides his cock in slowly, centimeter by centimeter, letting me feel how it goes in without pain, only fullness. That he starts soft and grows harder, that he fucks me with hunger but without forgetting that behind the dress there’s someone who needs to feel cared for at the same time as possessed. That he drives it deep while kissing my neck, that he whispers that I’m his woman while he pounds into me, that he makes me cum with his cock inside me and without touching me, that then he cums inside me, filling me, and stays there a while, holding me, not pulling out. That he makes me his on that bed until the two versions of me, the old one and the new one, become one.

That’s my fantasy: being the woman of a man who dresses me first and then makes me his. Discreet, attentive, intense when the time comes. Someone who understands that surrender is also cultivated, that the sweetest submission is born from care and not haste.

The first time showed me what I don’t want. Now I know exactly what I’m looking for. And every time I dress in front of the mirror, alone in my room, with my cock hard beneath the thong and my fingers teasing between my cheeks, I promise myself that the next time a man sees me like this, it will be someone who knows how to treat me like the woman I am when I put on that wig and stop hiding.

In the meantime, I’m still here, keeping my secret that isn’t quite a secret anymore, waiting for the one who knows how to wait.