The Night I Dressed Up So He Could Make Me His
I’m going to tell you how it all began, because every time I remember it, my pulse quickens and I feel that same mixture of shame and arousal that won’t let me go. It isn’t 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 began when I was very young. I must have been eleven or twelve. I would see my mother’s clothes hanging there and think they were pretty, soft, forbidden. It was just the two of us at home, so the only female reference I had was right there, within reach. One Sunday afternoon, I was left alone and couldn’t resist my 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 boy who hid in his room and became someone else, someone I liked better. I put everything away before she came home, my heart racing, and from then on it was my most carefully guarded secret.
I repeated that ritual whenever the house was empty. I learned to calculate my mother’s schedule, to fold the clothes exactly as I had found them, to erase every trace of perfume. With time, I stopped trying on only her dresses and began paying attention to the details: the way a skirt fell, the way a bra fit, the way stockings completely changed the line of a leg. It wasn’t curiosity about fabric. It was a way of recognizing myself.
The years passed. Today I’m twenty-three, I live alone in a small apartment near downtown, and I work at a boring office job that isn’t relevant here. On the outside I’m an ordinary guy: average height, slim, tan-skinned, with a smile people say is my best feature. Inside, I was still carrying that secret, only it was no longer childish curiosity. It had become a specific, urgent desire demanding to get out.
For a long time I dressed up alone. I bought lingerie online, using fake names and delivery addresses, and tried everything on whenever I knew no one was going to ring the bell. I would look at myself, touch my cock through my thong until it grew hard against the fabric, slip two fingers into my ass while imagining I was someone else. But there was always an invisible wall: the fantasy ended with me coming into a tissue, turning off the light, and going back to being the same person as always.
Until I decided to cross that wall.
***
I talked it over with myself for many nights before I dared. I wanted someone to see me. I wanted a man to see me dressed as a woman and desire me, not as a game, but for real. I wanted him to fuck me. I joined some of those messaging groups where people look for no-strings encounters without names or 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 as one.
It didn’t take long for someone to answer. He called himself Damián. His messages were direct, no beating around the bush, and I found that confidence attractive. He told me where, he told me when, and I, with my hands trembling over the phone, said yes.
The days before the encounter were a delicious torture. I couldn’t concentrate on anything. I went over every detail of how I was going to dress, practiced gestures I thought looked feminine in front of the mirror, imagined the scene again and again. Sometimes fear won and I thought about canceling, about writing to tell him I’d changed my mind. But then I would see myself in the mirror, with the promise of finally being seen, and desire would silence the fear.
We booked a room in a discreet hotel on the outskirts, one of those that charge by the hour and ask no questions. I arranged to arrive before him. I went dressed as a boy, with the women’s clothes packed in a backpack like contraband treasure. My stomach was tied in knots the whole way there.
The room smelled of cheap disinfectant and freshly ironed sheets. I closed the door, left the backpack on the bed, and went into the bathroom. I had already shaved my legs and my ass, smoother than ever, and that alone made me feel different, more exposed.
I began dressing slowly, almost ceremonially. The red thong first, pressing the fabric against my cock, which was already getting hard from sheer nerves. Then the fishnet stockings, pulling them up inch by inch, feeling the fabric tighten exactly where I wanted it to. The garter belt. The pink bra with a little padding. And finally a tight black dress that didn’t match any of the rest at all, but it was the one I had, and honestly, at that moment I didn’t care.
I put on the wig, also black, and combed the strands in front of the bathroom mirror, its surface spotted and grimy. I applied my lipstick slowly, my hand never quite managing to stop trembling. And when I looked up, I didn’t see the same old boy. I saw someone new. I liked myself so much that I stood there for a while, watching myself, rolling my hips, discovering how the dress moved around me.
I touched my face as if to confirm that the person there was really me. I ran my fingers over the fabric of the dress, along the curve of the garter belt beneath the skirt, over the edge of the stockings, and higher, until I brushed against my cock pressing into the red thong. Every texture reminded me that this was really happening, that it wasn’t one of countless secret afternoons in my room. This time someone was waiting for me on the other side of the door. For the first time I wasn’t hiding from anyone.
This is me. At last.
I touched the bathroom door, intending to step out like a real lady, ready for a slow courtship, for kisses before anything else. That was the movie playing in my head.
***
But reality hadn’t read my script.
When I came out, Damián was already completely naked on the bed, his hard cock resting against his stomach, thick, veined, glistening at the tip. He looked me up and down with a smile, and I’m not going to lie: seeing him like that turned me on immediately. He was bigger than I expected, broad-shouldered, with the attitude of a man accustomed to taking what he wanted. My body reacted before my mind did. My thighs tightened beneath the dress, and I felt a wet tug at my opening just from looking at his cock.
I had expected a prelude. Caresses over the fabric of the dress, kisses on my neck, hands moving slowly over me. I had spent years imagining exactly that. But he had another idea, and he made it clear right away.
“Come here,” he said, patting the mattress. “Get up here.”
I crawled toward the bed, feeling insecure and aroused in equal measure. The dress rode up in back, and I knew he could see my thong, the garter belt, the line of my shaved ass. Damián licked his lips as he watched me. He grabbed me by the nape and planted a rough kiss on me, almost biting my painted lip, while his other hand squeezed one of my fake breasts and then moved down to grab my cock through the thong.
“Look how hard you are, little slut,” he murmured against my mouth. “And dressed like that, too. You’re going to make a fantastic little whore.”
The word made me tremble. No one had ever spoken to me like that. I brought his hand to his cock, feeling it pulse between my fingers, thick and hot. I squeezed it, and he groaned under his breath. I began to jerk him off slowly, moving my fist from the base to the glans, feeling it grow even harder. I liked that. That was power. Without thinking too much, I lowered my head, my painted lips trembling, and took him into my mouth.
He caught in my throat at once. It was too much cock for a mouth that had never sucked anything before. Damián put his hand on the back of my head and began setting the pace himself, pushing my head down until I felt his glans strike my throat. Tears sprang to 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 throbbing cock inside 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, bitch, suck that cock properly,” he panted, tugging at my wig. “Let it show that you wanted it.”
He pulled his cock from my mouth with a jerk, a strand of saliva hanging between my lips and his swollen glans. For a moment I thought he was going to kiss me, touch me, that the courtship I had imagined for years was finally coming. But no. For a moment I thought things were going to go the way I wanted.
“Get on all fours,” he cut me off.
I obeyed. I pulled the dress up to my waist, leaving my ass raised and the red thong wedged between my cheeks. I felt him push it aside with his thumb, leaving my hole exposed. I heard the click of a bottle of lubricant and breathed out. At least he was going to use some. But it was only a quick squirt over the tip of his cock, practically an afterthought, without giving me even a finger, without preparing me. And almost without warning, without enough saliva, without anything to soften the moment, he pushed inside me.
The burning was immediate. A sharp, searing pain that knocked the breath out of me and made me clutch the sheets with both hands until my knuckles turned white. I felt every inch of that cock forcing its way in, pushing and stretching my asshole until it sank all the way to the base. A muffled cry escaped me. It was nothing like the times I had explored my body at home, alone and slowly, with my fingers and a small dildo. That had been gentle, mine, controlled. This was rough, foreign, far too fast—a whole cock driven into an ass that had never held more than two fingers.
He began moving hard and hurriedly, gripping my hips and pulling almost the entire length of his cock out before driving it back in with a dry thrust. The mattress squeaked with every impact. I felt his balls knocking against my displaced thong, the skin of my buttocks bouncing, the wig slipping to one side. He told me to moan, to sound like a woman, to tell him I was his little slut.
“Tell me you like it, filthy girl. 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 came from a discomfort I didn’t know how to name. The burning wouldn’t go away. When he changed the angle and touched me inside where he needed to, my own cock, crushed against the mattress through the thong, gave a strange twitch, a stab of pleasure that mixed with the pain and confused me even more. My mind was divided: one part registered 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 end.
He sped up. His nails dug into my hip, he panted over me like an animal, and suddenly he pulled out, turned me over roughly, and began jerking off with the tip pressed against my painted lips.
“Open your mouth, open,” he growled.
I opened it. And he filled my face and mouth with thick semen, hot spurts spilling over my tongue, my chin, and the pink bra showing through the dress’s neckline. He finished with one last moan, rubbing his glans over my lips to wipe off the final drop. I stayed still, my mouth full, not knowing whether to swallow or spit. In the end I swallowed. I’m not sure why. I suppose that in the movie playing in my head, the woman I wanted to be swallowed.
When he was done, he dropped onto his side of the bed, satisfied and completely unaware that I had been left halfway between relief and disappointment, my own cock still hard and throbbing inside the thong, untouched. I dressed in silence, removed the wig with semen still sticky at the corner of my lips, and wiped my mouth in front of the same mirror where, not long before, I had felt invincible. In the bathroom, sitting on the toilet, I pulled down my thong and quickly jerked myself off until I came too, biting my lip so he wouldn’t hear me. I needed to bring it to an end on my own.
It wasn’t how I dreamed it.
And yet, as I drove home with the backpack once again on the passenger seat and the burning still lingering between my cheeks, I didn’t regret it. I had crossed the wall. I had let someone see me completely, dressed, real. I had sucked a cock and been fucked in the ass for the first time. No one could take that away from me. What was missing, I knew now, was finding the right person.
***
Because this is where my real fantasy begins, the one I replay in my head every night since then while I slowly masturbate in my lingerie.
I imagine someone who knows how to wait. A man who doesn’t get naked before I finish getting ready, but enjoys watching me become her. Who watches me put on my makeup, helps me pull up the dress’s zipper, 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, placing the thong on me with his fingers brushing against 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, my shoulders, the line of my stockings. Him speaking softly to me, telling me I’m pretty, calling me a slut but tenderly, treating me with the delicacy that first time lacked. A real courtship, patient, where haste doesn’t exist. Him having me kneel in front of him with the dress still on and letting 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 having me lie on my back in bed, opening my legs with my stockings still on and eating my ass with his tongue for a good long while, licking me, spitting on me, slipping in one finger first, then two, until he opens me completely. Him jerking my cock through the thong while opening me with his mouth. Letting me grow wet, stretched, begging.
And then, only after all that, changing the pace. Climbing on top of me, looking into my eyes, and pushing his cock inside slowly, inch by inch, letting me feel it enter without pain, only fullness. Starting gently and growing harder, fucking me eagerly without forgetting that behind the dress there is someone who needs to feel cared for at the same time as she is possessed. Driving deep into me while kissing my neck, whispering that I’m his woman as he thrusts, making me come with his cock inside me and without touching me, then coming inside me himself, filling me, and staying there for a while, holding me without pulling out. Making me his on that bed until the two versions of me, the old one and the new one, become one.
That is my fantasy: to be a man’s woman, with him dressing me first and then making me his. Discreet, attentive, intense when the moment arrives. Someone who understands that surrender must also be cultivated, that the sweetest submission grows from care, not haste.
The first time taught 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 playing between my cheeks, I promise myself that the next time a man sees me like this, he’ll 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, which is no longer entirely a secret, waiting for the one who knows how to wait.