The First Time They Made Me a Woman

My name is Vero, and for years I kept a secret that existed only inside my closet: I loved dressing as a woman. It wasn’t something I could easily explain, but women’s clothing had a texture, a softness, that I couldn’t find anywhere else. Thongs, stockings, skirts that hugged my hips—all of it awakened something in me that I didn’t know how to name and, for a long time, preferred not to name.

I’m slim, fair-skinned, with delicate features. I’ve always known that. I also knew, from the time I was a kid, that I could transform myself into something I liked more than what I was. Whenever I was home alone, I rummaged through my older sister’s wardrobe and tried on whatever I found. At first with shame, then with something resembling happiness. Many times I ended up wearing the thong, one hand slipped inside it, masturbating slowly in front of the mirror, watching the silk become stained with the clear liquid dribbling from the tip of my cock.

With time and a little independence, I began buying my own clothes. Little by little: first a pair of stockings, then a thong, then a complete outfit. I saved until I had a brown wig that fell to my shoulders, good-quality makeup, and three skirts that fit me as if they had been made for me. I would look at myself in the mirror dressed like that and feel that I was myself—more myself than at any other time of day.

But I wanted more. I wanted someone to see me like that. I wanted someone to treat me as what I was in those moments: a woman. I wanted another man’s cock in my mouth, in my ass; I wanted a man to fuck me with the wig on and fill me with cum.

***

I started exploring specialized forums and social networks. Profiles belonging to men who were looking for transvestites, who knew that world, who understood what it was about without needing explanations. At first I only looked. Then I created a discreet profile with half-body photos, without showing my face. The replies came quickly—too quickly, and most of them didn’t appeal to me.

Until Marcelo’s message appeared.

He was different. He didn’t start with an obscene photo or a direct proposition. He was a man in his forties, he wrote well, and introduced himself by name and without rushing. He said he had experience with girls like me and that what mattered most to him was making sure I felt comfortable. We exchanged messages for several weeks. He told me about his apartment, about living alone, about having learned to read people and knowing how to wait.

He didn’t pressure me once.

That was what finally convinced me.

***

I told him yes on a Thursday night. We arranged to meet the following Saturday, at four in the afternoon. He confirmed the address and told me I could change at his place if I preferred to arrive as a man. I didn’t have to think about it much: the idea of crossing the city dressed up still overwhelmed me. I would bring everything in my backpack and transform myself there.

I didn’t sleep well on Friday. I spent the night staring at the ceiling, mentally going over what I was going to wear. In the end I decided on a tight black skirt that reached halfway down my thighs, a red lace thong, a garter belt, black stockings, and a pair of heeled ankle boots that had cost me a fortune but made my legs look endless. Up top, a padded bra and a fitted V-neck blouse. The brown wig, wavy, falling over my shoulders.

I folded everything carefully into the backpack and tried to sleep.

***

On Saturday I woke up early. I checked the bag three times. I sent Marcelo a message telling him I was on my way and went outside to find a taxi.

As we moved through the traffic, with the backpack on my knees and my hands clasped together so no one would notice them trembling, I felt something difficult to describe. It wasn’t just nerves. It was anticipation, expectation, a kind of hunger that had been building for years and that was going to be satisfied for real that day. It was finally going to happen. I was finally going to have a cock inside me.

The taxi stopped in front of a brick building on a quiet street. I paid, got out, and stood on the sidewalk for a moment, looking at the intercom. I imagined turning around and going home. I imagined the empty apartment, the wig tucked away in its box, another night staring at the ceiling.

No. I pressed the buzzer.

***

Marcelo opened the door almost immediately. He was exactly as I had imagined him: tall, with a neatly trimmed salt-and-pepper beard and a calmness in the way he moved that made me feel less exposed than I had expected. He was wearing a blue shirt rolled up to the elbows and smiling without overdoing it.

“I’m glad you came,” he said, and let me in.

The apartment was tidy and bright. Soft music played in the background, something instrumental I didn’t recognize. He gestured toward the sofa and went to get something to drink. He came back with two glasses of sparkling water and told me the bathroom was at the end of the hall, that I should take all the time I needed.

I picked up the backpack and went.

***

The bathroom was spacious and well lit. I silently thanked him for that. I undressed slowly, put on the thong, adjusted the garter belt, and pulled the stockings smooth so there wouldn’t be any wrinkles. Then the bra, the blouse. I sat on the edge of the bathtub to put on the boots and laced them hook by hook, enjoying the process without rushing.

Then the makeup. Foundation, concealer, smoky eyeshadow, eyeliner. Mascara. A dark pink lipstick I liked because it was serious without being aggressive. Finally, the wig: I adjusted it carefully, combed it a little with my fingers, and looked at myself in the mirror.

The girl in the mirror looked back at me.

I smiled. She smiled too.

I opened the door and walked down the hall toward the living room, my heels clicking against the parquet.

***

Marcelo was standing beside the window. When he heard my footsteps, he turned, and what crossed his face was not surprise but approval. A slow, genuine approval that traveled up and down my body before he said anything.

“Everything looks so good on you,” he finally said. “You’re a gorgeous slut.”

It was a simple phrase, but it was exactly what I needed to hear. I felt something loosen in my chest, and something else tighten beneath my skirt.

He came closer. He took my hands and slowly turned me around, as if he wanted to see me from every angle. Then he stood behind me, put his hands on my shoulders, and spoke close to my ear:

“Are you comfortable?”

“Yes,” I answered. And it was true.

His lips found my neck. At first they were soft, exploring; then wetter, sucking the skin beneath my ear until my arms prickled. I closed my eyes and leaned back against him a little, feeling the heat of his body through the blouse. And I felt something else: the hard bulge of his cock pressing against my ass over the skirt. He was already hard, and he was big. He rubbed it slowly against me, emphasizing its size, letting me know what awaited me.

His hands slowly descended from my shoulders to my waist, wrapped around me, and drew me closer. One rose to my cleavage, found the padded bra, and squeezed a fake breast as if it were made of flesh. The other moved down to the skirt, lifted it slowly, and grabbed my ass over the lace thong, squeezing me hard. I could feel how much he liked what he saw, what he touched. That turned me on more than anything else.

“What an ass you’ve got, girl,” he murmured against my neck. “I’m going to split it open.”

A moan escaped me. I couldn’t help it.

He turned me around and we kissed. It was a long, unhurried kiss, with tongues, his hand gripping the back of my neck. While he kissed me, he slipped a hand under my skirt from the front and found my hard cock beneath the thong. He squeezed it through the lace, fondled it knowingly, and I moaned into his mouth. I forgot my nerves. I forgot everything.

***

He led me to the sofa and made me sit on his lap. He caressed my thigh over the stockings while kissing my neck again, and I let myself go, my hands resting on his forearms. I felt his hard cock beneath my ass, separated by two layers of fabric and nothing else. I moved just a little, rubbing myself against it, and he gave a low laugh.

“A slut from the very first minute,” he said. “That’s how I like you.”

Then he gently took me by the chin, looked me in the eyes, and said in a low voice:

“Kneel.”

He didn’t say it like a harsh command. He said it like someone who knew he would be obeyed because what he was proposing was what both of us wanted. I got off the sofa and knelt in front of him on the rug, my skirt falling around my sides and my heels resting on the floor.

He leaned back a little and waited.

I understood. I unbuckled his belt, lowered the zipper, and carefully pulled off his pants. When I lowered his underwear, his cock sprang out in front of my face, already completely hard, thick, with prominent veins and a swollen, glistening tip. It was big, bigger than I had imagined. My mouth watered.

I took it in both hands. One hand couldn’t cover the whole base. I stared at it for a second, hypnotized, then stuck out my tongue and slowly ran it over the tip, tasting, learning. I gathered the drop of pre-cum hanging from his glans and savored it. It tasted clean, salty, warm. I ran my tongue over it again, more slowly, from base to tip, following the thick vein running along the underside, and heard him breathe a little more deeply.

“That’s it, girl. Suck it properly.”

I did as he said. I opened my mouth and took it all the way in as far as I could. First halfway, getting my throat used to the thickness, finding a rhythm. I moved up and down slowly, my lips sealed firmly around the shaft, letting saliva dribble to lubricate it better. Then deeper. I felt the glans strike the back of my palate and kept lowering until my gag reflex made me stop.

I breathed through my nose, kept it inside, forced my throat to open. He didn’t force me: he let me set the pace, discover what I could and couldn’t do. He only placed one hand on my wig, without pushing, accompanying me. When I reached the base and held it there for a few seconds, my nose pressed against his pubis, I heard a low, satisfied sound escape him before he could stop it.

I came back up, drew a breath, spat on his cock to lubricate it more, and swallowed it again. I increased the pace. I sucked hungrily, my painted lips becoming smeared around it, strands of saliva hanging from my chin, the fake breasts in my bra trembling every time I raised and lowered my head. I wasn’t thinking about anything else anymore. I only wanted it to be hard, harder, thicker, readier to go inside me.

I ran my tongue over his balls, one and then the other, sucking them slowly while jerking him off with my hand. I returned to the tip, licked it in circles, and barely nipped it with my lips. He watched me with his jaw clenched.

“You suck it so well. You’re a natural slut.”

I smiled at him with his cock between my lips and swallowed it whole again.

***

Before he came, he stopped me. He took me by the shoulders, lifted me carefully, and led me to the bedroom, almost dragging me by the hair of the wig. The bed was large, with pale sheets. He made me sit on the edge, tore open my blouse by undoing it in two quick pulls, removed my bra, and left me with my breasts bare, my nipples hard and pink. He crouched down and sucked them one by one, biting them lightly while I caressed his head. Then he went to get a bottle of lubricant from the bedside table.

“Face down,” he told me. “Ass up.”

I lay down. He slowly lifted my skirt, revealing the garter belt and the red lace thong outlining the cleft of my ass. He stood there looking for a moment. He ran his hands over my buttocks, spread them with his thumbs, and smacked me loudly, making me flinch.

“You’ve been saving this ass for me, haven’t you?”

“Yes,” I murmured against the sheet.

He moved the thong aside with one finger, leaving my hole exposed. He crouched down, and I felt his hot tongue at my entrance. He licked me calmly, in circles, pushing the tip inside, softening me with saliva. I moaned against the pillow, gripping the sheets in my fists. No one had ever done that to me. His tongue went in and out, opening me patiently, and I pushed my ass back, asking for more.

Then came the lubricant. I felt the cold stream on my skin, followed by his finger, massaging in slow circles around my hole before entering. He pulled it out, went back in, up to the knuckle. Then two fingers, keeping them inside, moving them in a scissoring motion, opening me patiently. He curled them upward and found a spot that made me let out a muffled cry.

“There, isn’t it? That’s the place,” he murmured, massaging it with his fingers until a little stream escaped from my cock, soaking the sheet beneath me.

He didn’t rush me. He didn’t rush me, and that was the only thing I needed.

When he withdrew his fingers, he asked me to arch my back and press my chest into the mattress. I did. He placed a pillow beneath my hips to set my body at exactly the angle he wanted. He lubricated me again, generously, and I felt him pour another stream onto his cock and slowly jerk himself off to coat it all over.

Then I felt the pressure. The thick tip resting against my hole.

First at the entrance, firm but without force. When he met resistance, he stopped and waited, then pressed again. I felt myself opening by an inch, then another. It burned. I forced myself to breathe deeply, relax the muscle, receive him. Little by little. The head entered with a sudden tug and I let out a long whimper against the pillow. Each time a little farther in, until the muscle finally gave way and I felt him slide all the way inside, until his balls rested against mine and his pubis against my buttocks.

I released the breath I had been holding. I was full. Completely full, with a cock inside me for the first time in my life, and it was exactly what I had been waiting for.

“All right?” he asked.

“Yes,” I said. And it was true.

***

At first he moved slowly, letting me get used to the sensation. He pulled his cock halfway out and sank it back in, unhurried, each thrust a little firmer than the last. I felt it slide against the walls of my ass, marking every inch, widening me little by little. The lubricant made everything sound wet, obscene.

But as the minutes passed and I stopped feeling tense, he increased the pace. His hands held me by the hips, fingers digging into my skin at the level of the garter belt, and I could feel his body striking mine, dull and regular, filling the room along with the sounds of our breathing and the squelch of lubricant. His balls slapped against me with every thrust. The wig fell across my face.

“What a tight ass you’ve got, slut. I’m going to fill you completely.”

There was no way to think. There was only feeling.

I pushed back to receive him better, moving my hips so he could go deeper. He noticed and increased the intensity. He grabbed me by the hair of the wig, pulled my head back, and drove his cock all the way in with such force that I screamed into the sheet. The pillow beneath my hips kept me at the perfect angle, and each thrust went deeper, touching that spot inside me that made me see stars. I felt heat, pressure, a mixture of discomfort and pleasure without an exact name that I didn’t want to end.

“Tell me you like it.”

“I like it,” I panted. “I love it. Fuck me harder.”

He fucked me harder. He rode me like a slut, his hands on my hips, my buttocks smacking against his pubis. I grabbed my breasts, pinched my nipples, touched my cock as it dripped against the mattress without needing to move my hand. I felt it grow, tighten, and then suddenly, without warning, without touching it, I came with his cock inside me. A long, warm stream soaking the sheet beneath me. My whole ass contracted around him, squeezing him, and he released a hoarse growl.

“Ah, that’s it, squeeze me, slut. That’s it.”

He fucked me faster, almost angrily, seeking his own release. I was shattered, trembling, but I kept pushing my ass back, offering it to him, asking him to fill me.

But he came.

I heard his rhythm change, become more urgent and broken, followed by a deep, prolonged sound as he emptied himself inside me. I felt the hot contractions of his ejaculation pounding inside me, one after another, filling me until it began leaking down the sides of his cock. He stayed still for a few seconds, all his weight resting on me, breathing against my nape, his cock still throbbing inside. Then he slowly withdrew, and I felt the semen run down my thighs, warming the skin between my stockings and garter belt. He kissed me behind the ear.

“Good,” he said softly. That was all.

***

I stayed still for a moment, exhausted in a way I had never experienced before. It wasn’t just physical fatigue. It was something broader, as if I had crossed a threshold I could neither go back to nor wanted to.

Marcelo went to get towels and carefully cleaned me, running the cloth between my legs, drying my stained thighs. Then, before I could stand up, he opened the bedside drawer and took out something small. A black silicone plug, with a heart-shaped base. He coated it with lubricant, spread my buttocks, and pressed it against my hole, which was still dilated and dripping his cum. I felt it enter cold, and the muscle accepted it almost without resistance, closing around the base with a small spasm. I felt the semen trapped inside.

“For the trip home,” he said with half a smile. “That way you’ll remember me until you get there.”

I understood that I wasn’t supposed to remove it until I got home.

I went to the bathroom to fix myself up. I touched up my smeared makeup, adjusted my wig, pulled my thong over the plug, and straightened my skirt. I put everything in the backpack. Every step reminded me of what I was carrying inside. When I came out, he was waiting for me at the entrance with the same calmness he had had from the beginning.

“Take care,” he said, giving me a soft kiss on the cheek.

***

I took a taxi home with the backpack on my knees and my eyes fixed on the window. Every bump in the road made me feel the plug move inside me, pressing the semen against the walls of my ass. The city was still the same: the same traffic, the same lights, the same people walking along the sidewalk without knowing anything. Without knowing that the girl in the back seat was riding with her ass full of someone else’s cum, her stockings damp, her lipstick smeared from sucking a cock all the way down. I was the same person who had gotten into that taxi hours earlier, but something inside me had shifted and would never return to where it had been.

I got home, locked the door, and sat on the edge of the bed. It took me a while to remove the plug. When I did, I felt the warm stream of semen leak out, and I stayed still, staring at the ceiling, with no desire to hurry anywhere.

For several days I remembered every detail: the living-room rug, the background music, the cold lubricant, the dull impact of his body against mine, the thick cock opening me, the hot ejaculation inside me. The moment he asked whether I was all right and I answered yes without lying.

I’m still thinking about it. And I’ve already sent him a message to do it again.