The Last Night of the Year I Dressed as a Woman

I got off work when the last days of the year were already falling away, with that tightrope feeling in my stomach that always shows up whenever I’ve been behaving too well for too long. I hadn’t given myself a treat in months; I hadn’t allowed myself to be anything other than the serious, punctual man everyone expected. The city was mad with lights and urgency, and I walked through the crowd feeling something inside me pushing to get out.

I was watching, as I always do, without making it obvious. The women moved along the sidewalk with a confidence that hypnotized me. Tight skirts, fitted dresses that seemed ready to burst with every step, necklines that left almost nothing to the imagination. But what really stole my breath were the legs: dark stockings ending in towering heels, that sharp clicking on the pavement that made me turn my head.

If only it were me walking like that.

It wasn’t exactly envy. It was a deeper desire, harder to explain. I wanted to feel fabric hugging my waist, the cold of the stocking sliding up my thigh, the impossible balance on a stiletto heel. For one night, I wanted to stop pretending. I wanted, though I wouldn’t admit it fully even to myself, for someone else to look at me hungrily and fuck me the way a woman gets fucked.

I stopped in front of a mall window and went in almost without thinking. My heart was pounding as if I were doing something forbidden, and in a way I was: in this city there’s always someone ready to judge you for whatever you do. I found the lingerie aisle with my head bowed, praying no one I knew would appear around the corner.

There were dozens of styles hanging there. I went through the packages one by one, comparing textures, shine, lengths. Some fishnets, too obvious. Some light-colored nylons, too shy. In the end I chose black ones, plain, opaque, the kind that define the leg without shouting. While I was holding them, I was already imagining what I’d pair them with.

“Did you find what you were looking for?” the cashier asked me, a young girl with a nose piercing.

“It’s a gift,” I lied, and the word tasted bitter.

She smiled without malice and rang me up. I left with the bag clutched to my chest, as if inside it I were carrying a secret that might escape.

Out on the street, December’s cold slapped my face and brought me a little back to reality. I passed a couple laughing in each other’s arms, a group of office workers shouting as they celebrated the end of the year at the door of a bar. Nobody looked at me, the anonymous man in the gray coat with a shopping bag. And yet I felt as if everyone could guess what I was carrying, what I had been carrying in silence for years. I quickened my pace. The sooner I got home, the sooner I could shed this skin that felt tighter every day.

***

On the way home I also stopped for dinner. I knew I wouldn’t be able to settle until I did what I wanted to do, but my body needed something to eat if I meant to stay awake all night. I bought some fruit, a bottle of white wine to toast with myself, and some canapés I probably wouldn’t even touch. The whole way back my head was racing, going over my wardrobe from memory, deciding the order of what I was going to try on.

I’ve lived alone for a couple of years, in a small apartment in a quiet neighborhood. That solitude, which weighs on me so many nights, was a gift today. No one was going to ring the bell. No one was going to ask questions. I locked the door with both turns, left the bags by the entrance, and went straight to the bedroom.

At the back of the closet I keep what almost nobody knows I have. The basics, I always tell myself, though by now it’s not so basic anymore: dresses, skirts, low-cut shirts, formal blouses, heels, sandals, and of course underwear I would never dare hang out in the open. I took everything out with almost ceremonial care, laying it across the bed like someone preparing an altar.

I stripped off in one yank. The shirt, the pants, the boring briefs of the serious man, all of it hit the floor in a heap. I was already half hard just thinking about what was coming. I grabbed myself for a second in front of the mirror, gave it a slow shake, and forced myself to let go: if I came now, I’d ruin the whole night. First the ritual. Then, if I could hold out, the reward.

I started with something comfortable, to warm up. A short skirt and blouse set, simple lingerie: white cotton culotte panties and a padded bra that gave me a silhouette I don’t have, the silhouette of a woman with presence. I tucked my cock into the culotte, folding it back between my legs so the bulge wouldn’t show, and felt the fabric squeeze my balls with a strange, delicious pressure. I looked at myself in the full-length mirror and something loosened in my chest. This wasn’t a costume. It was a release, a feeling that I should always be like this, that the other one, the one in the tie, was the real costume.

***

I moved on to the dresses. I wanted to try them all, to see myself differently in each one. The first was white with tiny blue flowers, light, summery. It hung a little loose at the waist, so I gathered the extra fabric from behind with my hands and pulled until it hugged my figure. Suddenly the reflection changed: a defined waist, the skirt falling in a more feminine way. I pulled out my phone and took a picture of myself, just for me, just so I could remember later that this woman had existed for a while.

Look at yourself. Look at what you hide the rest of the year.

The second dress was more serious, the kind you’d wear to an elegant office. Black with white details, short sleeves, a straight skirt that fell just above my knees. When I put it on, I knew the moment I’d been waiting for had arrived.

I sat on the edge of the bed, opened the package, and took out the new stockings. I unrolled them slowly, one then the other, sliding them over the sole of my foot, over my ankle, over my calf, inch by inch up to my thigh. The friction of the nylon against my skin made my whole body tingle; my cock got hard again inside the culotte, pushing the fabric forward. I ran my hand over it, squeezing my cock against my belly through the cotton, and let out a short, ridiculous moan of a woman alone. I stood up, smoothed my skirt, and walked to the mirror, almost holding my breath.

What I saw left me speechless. The legs were shaped, dark, shining under the lamp light. A formal woman, restrained, with a hint of dangerous promise beneath the straight skirt. Only one thing was missing.

I searched through the pairs until I found a set of black stiletto heels, the tallest ones I own. I slipped them on carefully, tightened the buckles, and straightened up, swaying for a second before finding my balance. The heel changed everything: the angle of my back, the curve of my calf, the way the skirt fell over my sheathed thighs. I took a few steps around the room, hearing that clicking sound I love so much on the street, and for the first time that day I was the one making it.

A secretary. A secretary who would do anything for her boss. A slut with a folder and a pen.

The fantasy built itself in my head. An empty office late at night, the blinds half drawn, a secretary in dark stockings leaning over a desk. I braced myself on the dresser, mimicking the pose, arching my back a little, looking over my shoulder at an imaginary boss who devoured me with his eyes. Heat began to rise from my belly, slow and thick.

“Like this, boss,” I whispered to the mirror, to no one. “Like this, with the skirt hiked up. Rip my stockings if you want.”

I pulled my skirt up to my waist and stood there looking at the reflection with the culotte tight against me, the bulge of my cock pressed sideways, my legs spread over the heels. I ran one hand over my ass, over the cotton, squeezing one cheek and pulling it away from the other so I could see the crease underneath. With my other hand I touched my cock through the fabric, a slow stroke up and down, feeling it swell more and more, the tip pushing against the waistband of the culotte until a finger of skin, wet with pre-cum, peeked above the elastic.

I slid my hand inside. I grabbed my cock with two fingers, weighed it, let it go. A strand of pre-cum had stuck to my belly. I ran it over my lips as if it were gloss, looking myself in the eyes in the mirror. The secretary in the reflection licked her lips.

I walked to the kitchen just to feel the heels on the tile, to hear that sound in my own house. I poured myself a glass of the wine I’d bought and went back to the bedroom, sipping small mouthfuls, letting the alcohol undo the last knots. In front of the mirror I raised the glass toward my reflection, as if toasting with her, with that woman who stared back at me from the other side of the glass. For an instant I didn’t know which of us was real.

I set the glass on the dresser and turned my back to the mirror. I bent over the wooden surface until my elbows rested on it, my legs straight and spread wide, my skirt hiked up to my waist again, my ass lifted. I looked over my shoulder. There was the secretary: the reflection of a woman with her skirt hiked up, waiting for her boss to lift the rest and shove his cock into her without asking permission. I put one finger into my mouth to the knuckle, pulled it out dripping with saliva, and took it to my ass under the culotte. The elastic dug into my thigh when I pressed the fingertip against the hole. I closed my eyes and pushed it in slowly, up to the second knuckle, and I remembered all the times I’d looked at a man on the street and wondered what it would be like to have him on top of me, fucking me with my dress on and my stockings still in place.

“Fuck me, boss,” I said out loud, alone, squeezing the finger inside. “Fuck me with your whole cock. Break me.”

I yanked the finger out, my legs shaking. I nearly came right there, standing up, against the dresser. I breathed deeply, clenched my teeth, forced myself to wait. There was still the last dress.

***

But there was a last dress, and it was the one I had truly saved for the end. I took it down with both hands: electric blue, shiny, very short. It barely covered my thighs; the neckline dipped in a V, revealing a good part of the fake chest the padding gave me, and the fabric clung to my waist like a second skin.

I took off the black dress and slipped into the blue one with a shiver of anticipation. I had to sway a little to get it into place, and when I did, the hem sat so high that the edge of my stockings barely showed, that line of tension between the fabric and naked thigh that drives anyone crazy. I tied a satin bow around my waist, one I’d been saving, made a big coquettish knot, and planted myself in front of the mirror.

A gift. I’m a New Year’s gift waiting for someone to pull the bow and leave me open-legged.

I couldn’t hold back. The woman in the mirror was looking at me with parted lips, and I wanted her, wanted myself, with a force that startled me a little. I took out my phone again and started taking pictures of myself, changing poses, playing with the bow, letting one strap fall off my shoulder. With every shot I got more nervous, hotter. With my right foot on the edge of the bed, the skirt no longer covered anything: the culotte was fully visible, soaked in the center with the pre-cum that had been dripping all night, and above it the bulge shoved obscenely against the cotton, impossible to hide.

I set the phone on the dresser, propped against the wall so it would keep focusing on me, and brought my hands to my body. First over the fabric: palms moving up my thighs sheathed in stockings, feeling the nylon border, the edge of the dress, the shape of my chest. My breathing broke. I closed my eyes and let the secretary, the woman with the bow, the one in the mirror, merge into a single person.

I sat on the edge of the bed with my legs crossed, feeling the heel hang from my foot by the toe. One hand kept tracing the stocking; the other slipped under the blue hem. I wanted more. I needed more. I wanted that night to last long enough for me to forget the man in the tie, the judgment of the street, the lie I’d told the cashier.

I pulled the culotte down to mid-thigh, just enough for my cock to spring upward, stiff, the tip purple and shining with fluid. I looked at myself in the mirror: a girl dressed for a party, stockings immaculate and heels on, the satin bow still tied at her waist, and between her legs a rock-hard cock trembling in the air, without the slightest shame. The image made me dizzy. It seemed like the most obscene, most truthful, most mine thing I had ever seen.

I grabbed my cock with my right hand. I brought my left to the fake chest, pressing over the fabric as if it were real, twisting an imaginary nipple. I started jerking myself off with a clenched fist, slow, all the way up and down, letting the pre-cum act as lubricant. My heels dug into the floor every time I squeezed my thighs. My skirt kept riding up with every pull.

“Fuck me,” I whispered to the woman in the mirror, through clenched teeth. “Fuck me dressed. Fuck me with the stockings on. Don’t take them off me.”

I slid down to the floor on my knees, onto the rug, never stopping jerking myself off. I pressed my legs together, thighs in stockings rubbing against each other with a nylon sound that drove me wild. With my free hand I put two fingers in my mouth and soaked them well with saliva, sucking them deep, imagining it was the boss’s cock shoved down my throat. I pulled them out dripping and took them to my ass again, over the culotte half lowered, searching for the hole. I pushed one finger in, then the other. I thrust.

“Ah, you son of a bitch,” I moaned, not knowing who I was saying it to. “Put it all in me. Tear my ass open. Leave the stockings on.”

The fingers went in and out at the same rhythm as my hand on my cock. I was fucking myself, secretary and boss, woman and man, all at once. The blue dress was wrinkling around my waist, the bow had come undone from all the movement, one heel had tilted to the side and I hadn’t even noticed. In the mirror, the woman in the reflection had her mouth open, her eyes rolled back, two fingers knuckle-deep in her own ass under the hiked-up skirt, and the cock slipping between the fingers of her other hand, swollen, red, on the verge.

Outside, someone set off the first firecracker of the season and the city answered with a distant chorus of horns. I, locked in my room with my new stockings and the bow slowly coming undone between my fingers, toasted the year that was ending in my own way.

I felt the orgasm rising from my balls, like a current that climbed up my spine and got stuck for a second in my throat. I pushed my fingers deeper, clenched my thighs, and let go. The first burst splashed my belly beneath the blue dress; the second, longer one, stained the inside of my right thigh, a thick white thread sliding over the black stocking to the edge of the heel. The rest hit the floor between my knees. It didn’t stop. I kept pumping, mouth open, watching myself come in the mirror, seeing that woman in the party dress and immaculate stockings dirtying herself underneath, semen dripping over black nylon.

I stayed still for a long while, kneeling on the rug, fingers still inside, cock still in my hand, chest rising and falling. For all the months of behaving myself. And, above all, for the slut that only let me be myself when I locked the door with both turns and nobody could see me.

I pulled my fingers out slowly, wiped them on the stained stocking without caring, and kept staring at myself. The semen gleamed on the nylon’s black sheen like another decoration, another proof that the woman in the mirror had existed, had come, had finished. The blue dress wrinkled at the waist. The bow lay loose over my hips. One heel sat cocked to the side.

The reflection stared back at me, lit from within, and for once I didn’t look away.