I Dressed as a Woman for Him for the First Time
My name is Carolina, although that’s not the name that appears on my ID. It’s the one I chose for myself, the one I whisper to myself when I look in the mirror and finally recognize myself. I’m twenty-eight, slim and short, and from a very young age I knew that something in me didn’t fit what others expected. I liked boys, yes, but there was something else too: I wanted to feel desired as a woman, dress like one, move like one, spread my legs like one, and be fucked like one.
The problem is I live with my family, and privacy is a luxury I almost never have. So my first experiments were stolen, hidden, in the gaps left by afternoons when everyone went out.
The first time was almost by accident. My parents had gone to have lunch at some relatives’ house and my older sister was away with her boyfriend. I had the whole house to myself for hours. I remember going into her room with my heart pounding in my chest, as if I were about to steal something forbidden. I opened her closet and stood there for a long while, looking, not daring to touch anything.
In the end I made up my mind. I took out a tight black skirt, a top that left my shoulders bare, a pair of red lace panties, and some stockings. It was hell putting the stockings on without ripping them; my nails kept snagging and I was trembling too much. I tried walking in a pair of heels I found, but I wobbled like a newborn colt and almost smashed my face into the dresser.
I don’t know how to do any of this, I thought. But I want to learn everything.
When I finally stood in front of the full-length mirror, I lost my breath. It wasn’t perfect, not by a long shot. I didn’t know how to put on makeup and my hair was short. But something about the silhouette, about the way the skirt hugged my hips, made me feel something I had never felt before. I looked good. I looked desirable. For the first time, I looked like me.
***
From that day on, every time the house was empty I repeated the ritual. I dressed up, looked at myself, practiced walking in heels while holding onto the walls. I started daydreaming about a man seeing me like that, touching me, prying my legs open and fucking me deep while calling me by my woman’s name. The fantasy became so intense that the mirror wasn’t enough anymore. I’d end up stretched out on my bed with the red panties on, my hard cock throbbing under the lace, and I’d masturbate biting the pillow while I shoved two saliva-soaked fingers into my ass, imagining it was a man fucking me.
I had been with two guys before, quite a while back, but never dressed up, never feeling like her. Those experiences had been timid, almost clumsy, quick blowjobs and nervous fingers in the dark. This time I wanted something different. I wanted to give myself as a woman. I wanted to suck a cock on my knees with my dress hiked up, I wanted my ass opened and filled with cum.
The problem was still the same as always: I had no idea where to start. I didn’t know anyone in the scene and I was too embarrassed to ask. So I did the only thing that occurred to me: I searched online. I joined a hookup group, put up a photo where you could barely see my face but my ass showed above the red panties, and waited.
Several people replied, but most of them made me uncomfortable. Rude messages, photos of cocks I hadn’t asked for, men who only wanted to spout a few lines and shove their dick into me that very night. I came close to deleting everything several times.
Then Andrés appeared.
He was in his thirties, had a calm smile in his profile photo and, above all, patience. He didn’t pressure me. He asked how I felt, whether it was my first time, what I liked and what I didn’t. We talked for days before even thinking about meeting up. He confessed that he adored girls like me, that he’d been craving to fuck a rookie transvestite for a long time, teach her to suck properly and cum inside her virgin ass. And I won’t lie, that attention melted me and got my cock hard under my pajamas.
—Whenever you want, come to my place —he wrote one afternoon—. No rush. Whatever happens, happens. But I’m warning you: if I see you in those red panties, I won’t let you go until I’ve got your ass dripping.
I spent two days turning that message over in my head, rereading it and rubbing myself against the mattress. On the third I told him yes.
***
The afternoon of the date I left the house dressed like a boy, plain and ordinary, with a backpack over my shoulder. Inside I had my little arsenal: a tight dress, the stockings, the red panties I already considered mine, and the heels I had practiced in so much. My heart was racing as I crossed the city. I live in Valencia, and I swear that metro ride felt endless; I had the sensation that everyone knew what I was carrying in my backpack and what cock I was heading to.
Andrés lived in an old building, one of those with worn marble stairs. He opened the door in a T-shirt and jeans, barefoot, and greeted me with a smile that disarmed me instantly.
—Come in, relax —he said—. Do you want to change? The bathroom is that door.
I locked myself in there with shaking hands. I put on the panties, the stockings, the dress. I looked at myself in the sink mirror and took a deep breath. The bulge of my cock showed against the red lace, already half hard from nerves alone. That’s it. Now it’s real. When I came out, barefoot because I still didn’t dare wear the heels, he was sitting on the sofa. He looked me over from top to bottom and I saw his eyes light up and the outline of his dick start to show against his jeans.
—You’re gorgeous —he said, and he meant it—. Come here, little slut, sit on me.
I sat astride him, stiff as a board. He didn’t lunge. He brushed a strand of hair away from my face and started kissing my neck slowly, whispering in my ear while his hard cock pressed between my ass cheeks over the dress.
—I’ve been thinking about this moment all week —he murmured—. How good you were going to look dressed like this, how nicely you were going to suck me off, how tight that little ass of yours was going to be.
I could barely move from nerves. I felt his hot breath on my skin and a tingle running down my whole back, tightening my cock inside the panties. His hand rested on my knee and started moving up the stocking, very slowly, until it reached the hem of the dress. When he lifted it all the way and saw the red lace stretched tight over my erection, he let out a rough breath.
—Fuck —he said softly—. Jesus. Look at how hard you already are, you filthy girl.
He touched me through the fabric, squeezing my cock with his open palm, and a moan escaped me that I didn’t even know was in there. It was like an electric current shot through my whole body. I was embarrassed by the sound, but he seemed to love it, because he kept at it, stroking me up and down while biting my earlobe. With his other hand he slipped his fingers under the elastic of my panties and fiddled between my ass cheeks, searching for my hole from behind. When the tip of his finger brushed my puckered opening, another, higher moan escaped me and I arched against him.
—That’s what I like —he gasped—. I’m going to leave you wet front and back.
He lifted my chin and kissed me on the mouth, pushing his tongue all the way in while he kept massaging my cock over the lace. I could feel the bulge of his dick digging between my ass cheeks and my own arousal beginning to soak the red fabric in front.
***
I don’t remember the exact order of what came after. The memory of that afternoon is more a mosaic of sensations than a neat sequence. I know that at some point he slid me off the sofa and to the floor and knelt me between his legs.
He unbuttoned his pants, pulled down his briefs, and took it out in front of me. It was thick, bigger than I had imagined, with a shiny glans and a clear drop hanging from the tip. I just stared at it, hypnotized and a little scared. It smelled of clean skin and something warm, intimate, masculine, something that stirred me inside and made me start salivating at once. I brought it to my mouth awkwardly, stuck out my tongue, and licked the drop from the tip.
—Slowly —he said, stroking my hair—. Don’t rush. Open wide, stick your whole tongue out and run it all over the shaft.
I had no idea what to do. I took it in my hand by the base and ran my tongue from the balls to the head, clumsily, leaving a trail of saliva. Then I opened my mouth and took it in, first just the head, sealing my lips around it and sucking hard. He let out a long gasp and gripped the back of my neck.
—That’s it, fuck, like that, all of it.
I pushed it to the back of my throat and choked on the first try. Tears sprang to my eyes and saliva dripped down my chin and my cheeks burned with sheer embarrassment. But he was holding my hair gently and guiding me, setting the pace, pulling it out when I ran out of breath and sliding it back in when I could breathe again. Little by little I lost my shyness. I started enjoying it, watching for his reactions myself, sucking his balls, taking him deep on purpose so I could hear him groan, feeling his thighs tense when I ran my tongue just under the head.
—That’s it, gorgeous —he gasped—. Just like that. You suck cock so well for it being your first time, slut, you’ve got it gushing.
Hearing those words drove me wild. I’d pull it out of my mouth slick with saliva, rub it over my face, over my painted lips, and take it in again. My cock was getting rock hard inside the soaked panties. For the first time in my life I felt exactly what I had always wanted to be: a bitch on her knees sucking a cock.
—Come here before I cum in your mouth —he said, yanking my hair up—. Not yet. First I want to fuck that ass.
***
He half dragged me to the bedroom. He laid me face down on the bed, hiked my dress up to my waist, and pulled my red panties halfway down my thighs, leaving them hanging around my legs like a filthy mess. He stood there for a moment looking at me, my ass bare and framed by the lowered lace and the stockings.
—What a beautiful ass you’ve got —he said, running his hand over it and then parting my cheeks with his thumbs to look at my hole—. So tight. I’m going to open you up real good.
He bent down and I suddenly felt his hot tongue between my cheeks, licking my puckered hole from top to bottom. I screamed into the pillow and grabbed the sheets. I wasn’t expecting that, I wasn’t expecting a man to eat my ass like that, soaking it, pushing the tip of his tongue into me, sucking my hole like it was a cunt. He had me writhing on the mattress, arching my back to offer him more.
—Please —I moaned, not really knowing what I was asking for—. Please, more.
He took a bottle of lube from the nightstand, thank God, because I had been so nervous I hadn’t even thought about that. I felt the cold gel dripping between my ass cheeks and then a finger easing in carefully, circling. I tensed up at once.
—Relax —he whispered—. Breathe. Push out like you’re trying to shit, that makes it go in better. If it hurts, we stop.
I breathed. I did what he said. The first finger stopped hurting and started to feel good, very good, touching something inside me that made me drool onto the pillow. Then a second finger went in, stretching me open, and I moaned against the fabric and gripped the sheets with both hands while he finger-fucked me. It was a strange mix of discomfort and pleasure that I had never felt before, and the longer it lasted, the more I wanted it. I started moving my ass back, impaling myself on his fingers, hunting for more.
—Look at this little slut —he laughed under his breath—. She’s fucking my hand all by herself.
He slipped in a third finger and opened me a little more. I was no longer even a person, just a body trembling with my dress hiked up and my panties around my thighs, moaning yes, please, to fuck me, to put it in.
—Are you ready? —he asked in my ear, lying down over my back.
—Yes —I said, almost voiceless—. Please. Put it in me.
He put on a condom, smeared more lube on his cock and on my hole, and rested the tip against my opening. He started entering me very slowly. The first seconds really hurt, a sharp burn that made me clench my teeth; he was much thicker than his fingers and I felt like I was being split in two. I had to remind myself to breathe, to push out. But he stayed still as soon as the head was inside, letting me adjust, stroking my lower back and my breasts over the dress with a tenderness I hadn’t expected.
—Easy —he kept repeating—. Hang in there, the worst part’s over. Open up for me, like that, nice and wide.
And it did. Suddenly, where there had been pain there was something else. He pushed a little more and I felt him sliding in all the way, centimeter by centimeter, until his balls were hitting my ass cheeks and I knew I had all of him inside. A wave of heat rose from my belly and spread through my whole body. He started moving, first gently, pulling almost all the way out and then sliding back in slowly, then a little faster, and I could do nothing but repeat his name and ask him to keep going.
—Don’t stop —I moaned into the pillow—. Please, don’t stop. Fuck me, fuck me harder.
He grabbed my hips with both hands and started pounding for real, each thrust making the bed creak and my ass bounce against his thighs with a wet smack. He had me pinned to the mattress, face smashed into the pillow and my ass lifted for him. My cock was rubbing against the sheets with every thrust and I felt like I was going to cum without even touching myself.
—This beginner’s ass fucks so well —he panted over me—. Look at it sucking my cock.
He yanked my hair back to lift my head and whispered in my ear, without stopping the hammering from behind, that I was his little whore, that he was going to fill me completely. I nodded like crazy, moaning that yes, that I was his, that he should fill me. He slid a hand underneath, grabbed me over the soaked lace, and jerked me in time with his thrusts. I held on for two, three more hits and came in a gush inside the red panties, soaking everything, screaming into the pillow while my ass clenched in spasms around his cock.
—Fuck, fuck, how tight you are —he growled—. Here I come, slut.
It didn’t last much longer after that, honestly. We were both too worked up to hold on. I felt him tense up, gripping my hips with his fingers digging into the flesh, and let out a long, low groan as he finished in hard strokes inside me, emptying into the condom with his cock buried to the hilt. I collapsed onto the bed, trembling, my dress wrinkled up at the waist, my panties full of my own cum, my breathing ragged.
He pulled out slowly and I felt the strange emptiness, my opening throbbing open, a thread of lube sliding down my thigh. We stayed like that for a while, in silence, his chest rising and falling against my back. No words were needed.
***
Afterward he helped me up, brought me a glass of water, and let me use his bathroom to freshen up. I looked at myself in the mirror with smeared mascara, swollen lips, mussed hair, and a smile that wouldn’t fit on my face. Before I left he gave me a long kiss at the door, squeezed one of my ass cheeks over the dress, and told me that whenever I wanted to do it again, I knew where he was.
I went back home at night, dressed as a boy again, with the women’s clothes folded in my backpack —the red panties still sticky inside a separate bag— and a goofy smile that wouldn’t leave my face. My ass ached with every step and I loved that soreness. On the metro I looked at people and thought none of them could imagine that I’d just been fucked for the first time as a woman. I was carrying a beautiful secret pressed against my skin.
Since then I haven’t seen anyone else. Partly because it’s hard to find someone you can trust —you read so many nasty things online that it’s scary—, and partly because I want to learn properly before going any further. I want to master makeup, buy my own clothes, my own shoes, my own dildo to practice with on my own and not depend on my sister’s closet.
Above all, I want to find other girls like me. Sisters who can teach me, who can tell me how to suck a cock properly, how to open an ass with lube before a date, who can help me become the woman I know I have inside me. That’s why I got up the nerve to write this, even though my hands are shaking a little as I do.
If you’ve made it this far and seen yourself in my words, let me know what you thought. And if you’ve ever hesitated, like I hesitated so many times in front of that mirror with a hard cock inside a pair of borrowed panties, I’m telling you this from the heart: it’s worth taking the step. On the other side there’s a version of you waiting to be born, legs open and wanting everything.