The Night I Went Out Dressed as a Woman

I’m going to tell it exactly as it happened, without embellishment or lies, because I haven’t told anyone in months and I need to get it out of me. I’m twenty-four, I’ve been living with my girlfriend for two years, and to anyone who knows me, I’m a regular guy: the gym three times a week, office job, soccer with my friends on Sundays. No one would ever suspect what I did that Friday night when I was left alone in the apartment.

Camila had gone to sleep at her parents’ house because her mother was sick and needed help with her medications. I told her it was fine, that I’d take the chance to organize the closet, watch some series, and rest. She kissed my forehead, grabbed her bag, and left her keys on the kitchen table. It was nine when she closed the door.

At eleven I was stretched out on the couch with my phone in my hand, mindlessly scrolling through videos. I wasn’t looking for anything in particular, but the algorithm, which knows you better than you know yourself, kept dragging me toward clips of women walking in heels, taking their clothes off in front of the mirror, adjusting a fishnet stocking over a thigh. It wasn’t the first time those videos had made me feel something different from ordinary desire. I didn’t want them: I envied them. I wanted to be in their place, to feel what they feel when a man looks at them and his mouth goes dry.

What if I do it?

The thought came that way, without warning. Camila wasn’t coming back until Sunday. I had the whole house to myself, her clothes hanging in the closet, her makeup on the dresser. No one ever had to find out. I got up from the couch before my mind could stop me.

***

I stripped in the middle of the bedroom. Camila is five foot one; I’m almost twelve inches taller. Her clothes wouldn’t fit me, but I wanted to try anyway. I opened the first drawer and took out a black lace bra, one she wore when we went out to dinner. Camila has a big chest, so the cups were loose on me on every side. Luckily, in another drawer she kept some silicone inserts shaped like teardrops, the kind that stick to the skin to add volume under a low-cut dress. I put them inside the cups and, when I looked at myself in the mirror, I wasn’t quite myself anymore.

The black panties were a little harder. It’s difficult to hide what one has when the underwear was designed not to hide anything. I grabbed my cock with one hand, pulled my balls back with the other, and worked everything into place between my legs, tight against my perineum. The fabric sank into my ass crack and tore a gasp out of me I hadn’t expected. I felt the lace brush my hole for the first time in my life and got goosebumps. It wasn’t the desire of a man for a woman: it was the desire to be desired, to be fucked, to have someone put something inside me and make me moan.

I took out a black denim skirt, short, the one she wore when she went out. It rode higher on me than on her, which, far from bothering me, I liked. I looked up at the closet mirror and saw a back wider than normal but with a waist, with long legs, with an ass the gym had made firm and that now, stuffed into someone else’s skirt, seemed to be asking for something. I stood there for a long while looking at myself from different angles, and without even noticing I ran my hand over the skirt, between my butt cheeks, squeezing. The cock, trapped where I’d hidden it, started swelling against the fabric.

On top I put on a thin sweater, also black, with a boat neckline that left my collarbones and the outline of the padded bra exposed. I sat down at the vanity. Camila had shown me as a joke, one night during lockdown, how to use concealer and foundation. I did it for real. I covered the beginning of my beard with two layers of makeup, sculpted my cheekbones, lined my eyes with a thick winged stroke, and painted my lips a dark red, almost wine-colored. Then I took the mascara and put on three coats. When I combed my bangs to one side, I let a lock fall over my right eye.

All that was left was my legs. I took out some fishnet stockings, pulled them up slowly so I wouldn’t tear them, and noticed how they changed everything. The gym-trained calves stopped looking male. They were long legs, the legs of a tall woman, a woman going out to a party. I slipped into a pair of stiletto heels Camila barely used because they were intentionally too big for her —she’d inherited them from a friend— and for once that “too big” was for me.

I stood in front of the full-length mirror. The warm light from the bedside lamp was flattering. I didn’t recognize myself. I felt fear, I felt pride, and I felt, above all, a huge urge for someone to see me, to touch me, to slide a hand under the skirt and discover what was there.

***

At first I was going to stay inside the house. Walk around the living room a bit, take some photos, feel the heels against the parquet floor, and put everything away before dawn. But the apartment felt too small. The walls didn’t give back what I needed. I needed eyes. I needed the street.

It was close to two in the morning. I put on a long overcoat, grabbed the keys, my phone, a bill just in case, and a condom that was on my nightstand —I wasn’t planning to use it, I told myself, but what did I know about what was about to happen—. I locked the door, double-turned it, and took the six floors down in the elevator, careful, for the first time in years, not to put my weight on my heels so I wouldn’t make noise.

The street was almost empty. We live in a quiet neighborhood, a little away from downtown. The few cars that passed were going fast, as if they knew nobody strolled around at that hour. I walked half a block to a corner with better lighting. I took off the overcoat, folded it over my arm, and stood there as if I were waiting for a taxi I never called.

The first car that saw me was a white Corolla. The driver turned his head so fast he almost hopped the curb. He didn’t stop, but a block later I saw him pull over and start circling the block. I didn’t dare wait for him. I moved two more corners ahead.

A family passed in a pickup truck. The father stared straight ahead, but the mother fixed her eyes on me through the window, and I knew, with a strange clarity, that she had understood more than I had shown. I lowered my head, touched my bangs, and kept walking.

Then two guys on a motorcycle passed. One of them shouted something from behind, a textbook obscenity —“Suck my cock, doll!”— and both of them laughed and sped up. It didn’t hurt me. It turned me on. I felt my cock twitch against the panties, pulling the lace forward, and I had to slip my hand under the skirt to set it back against my perineum.

Half a block away there was a security guard standing in front of an office building. I had seen him from a distance but thought I wouldn’t dare. I walked slowly toward his sidewalk, feeling each step, feeling the fabric of the skirt brush my thighs. When I got to his level, I pretended to be looking for something in my bag —I didn’t have a bag— and bent down. The skirt rode up in the back and I felt the cold breeze slip between my butt cheeks. He had the radio in his hand and never brought it to his mouth. Out of the corner of my eye I saw him adjust the bulge in his pants with his palm, squeeze it, move it to one side so it wouldn’t bother him. He had a hard cock clearly outlined against the uniform fabric, and he held my gaze while I, still bent over, ran my tongue over my lower lip. He didn’t say anything, but he didn’t stop looking at me until I turned the corner, and I walked on knowing that if I had gone back on my steps he would have pulled me into the doorway and let me do whatever I wanted.

***

The car that stopped was a dark gray sedan with partially tinted windows. The passenger window rolled down. The driver leaned a little over the seat.

—How much? —he asked, no greeting.

I went silent. I hadn’t thought of that script. I hadn’t thought of any script. I stammered something even I didn’t understand. He laughed, a low, patient laugh, and opened the door from the inside.

—Get in —he said—. We’ll figure it out after.

I got in.

He smelled like men’s cologne, mixed with the leather of the upholstery and something like old tobacco. He must have been around forty, short beard, wedding ring on. He put his hand on my thigh as soon as he pulled away. He slid it up a couple of inches and left it there, not squeezing, waiting to see if I moved away.

I didn’t move away.

—You’re shaking —he said.

—It’s the cold.

—It’s not the cold. —He smiled without looking at me—. First time you’ve gotten into a car?

I nodded. What was I going to lie for. Then I regretted nodding so quickly, but it was done.

Damián —he didn’t tell me then; he told me later, leaning back against the seat— handled that car like it was his own bed. He drove with one hand and explored me with the other. He hiked my skirt up without asking, slid two fingers over my panties, and paused for a second when he understood what was underneath.

—Look at that —he murmured, almost to himself—. Didn’t expect that.

I went rigid, sure the ride was over, that he was going to brake hard and throw me out. But no. Damián squeezed over the lace, felt the cock hidden back there, and gave a low laugh, something like recognition. He tugged my panties until my cock popped out to the side, hard, already wet at the tip, and took it in his whole hand. He gave it two slow shakes while still driving.

—Still, you’re a little beauty —he said—. And this thing you’ve got down here doesn’t bother me at all. On the contrary. Let’s see if you work with your mouth as well as you do with your face.

He pushed two fingers against my lips and I let them in. I sucked the tips and drew them out with my tongue, leaving him a shining strand of saliva between his index and middle finger. He brought them back down, rubbed them over his own cock through his pants, and then slid them between my butt cheeks over the panties. One of the two fingers found the hole and pressed there, not entering, just insinuating itself, and a moan slipped out of me from somewhere I didn’t know I had. No one had ever touched me there. Not even me, except in the shower, and always only from the outside, always afraid of what I might feel.

—You’ll see —he said, without removing the finger—. You’ll see what you’re missing.

He drove about ten blocks toward an industrial area I knew by day, full of locked warehouses and a single shuttered convenience store. He parked against a wall with no windows, where the only light came from a yellow streetlamp half a block away. He shut off the engine.

—Back seat —he said.

***

The back seat was leather, cold at first. Damián unbuckled his belt, pulled his pants down to his ankles, and took out a cock that in the dim light looked bigger than I had imagined. It wasn’t huge, but it was thick, with prominent veins, and the head was shiny and reddish. He settled back against the seat, legs apart, and gripped it at the base.

—Come here. Suck me.

I knelt in the footwell, skirt hiked up and fishnets leaving rings on my thighs. It was the exact right height. I started slowly, licking him along the side, from base to tip, the way I had seen Camila do to me. I licked his balls too, first fearfully, then eagerly, taking them one by one between my lips, tugging them slightly outward. Damián threw his head back and let out a long growl.

—Like that, whore, like that.

I ran my tongue over the frenulum, in circles, and felt him swell between his fingers. When the head started leaking fluid, I sucked it, swallowed it, and lowered my mouth halfway down. Saliva was already running from my chin onto Camila’s sweater. I was going to have to throw that sweater away. I didn’t care.

—Look at me —he said.

I lifted my eyes. His hair was mussed, his shirt collar open, a vein standing out at his temple. When he saw my lipstick smeared and my eyeliner starting to tremble, he let out a sigh that was worth more than any compliment.

—You’re a whore —he said, not with contempt, almost in awe—. And you don’t even know how much.

I took him in all the way. As far as I could. My eyes filled with water, I coughed, spat him out for a moment with a thick string hanging from my lip, then took him back. Damián grabbed my hair with both hands and started fucking my mouth himself. Not violently: with rhythm. As if he were teaching me how to dance. I kept going, choking, spitting, taking him back. Every thrust shoved him to the back of my throat, and every time he pulled out I gasped for air and went back down on my own, without being asked, craving him. There, with another man’s cock in my mouth, I discovered that I liked choking. That I liked feeling it push me past my limit. That I liked the low groan he made every time I squeezed the base with my lips.

—Good girl —he said, and pressed his thumb into my cheek, squeezing from the outside to feel his cock against it—. Good girl.

Suddenly he pulled out of my mouth, leaned forward, and grabbed my jaw with his hand. A thread of saliva and pre-cum still linked his cock to my lips.

—Turn around —he ordered—. Take off those panties.

I turned around on the seat. I ended up on my knees, hands against the fogged-up window, the overcoat on the floor, the skirt bunched up over my lower back. I pulled my own panties down to my knees, with the fishnets still on, and felt the cold air of the car hit my spread ass. Damián stayed silent for a second, looking.

—What a ass you’ve got —he said, and gave me a sharp slap that made me jump—. What an ass. And virgin, right?

—Yes —I whispered. It was the first time I said the word out loud referring to myself. It burned and I liked it at the same time.

I felt a hot spit land between my butt cheeks. He spread it with his thumb over the hole, wetting it, circling it. He spit again. Spread it again. Then he pushed his thumb in, just the first knuckle, and I arched and let out a sharp, feminine moan I hadn’t known was in me.

—Oh, look at it go in —he said—. Look at how it asks for it.

He worked me with his thumb for a while, in and out, opening me. Then he switched to his middle finger, longer, and reached a place inside that made my legs tremble. My cock, dangling between my thighs, started dripping onto the leather seat all by itself without anyone touching it. Damián noticed. He laughed.

—You don’t even grab it and it’s already leaking. You’re going to come just from a cock in your ass, doll.

He shoved in a second finger. It hurt, I complained, I clenched my teeth. He didn’t stop but didn’t rush either. He scissored them, pulled them out, spat again, pushed them back in. I felt something inside me start to open that had been closed my whole life.

—Did you bring anything? —he asked, with a calm that surprised me, never taking his hand away.

—In the overcoat pocket —I said, and my voice came out higher than I expected.

He stretched, felt around on the floor, took the overcoat, and rummaged through it. He found the condom. He tore it open with his teeth. He put it on with one hand, never stopping working my ass with the other, and when he was done he spit once more between my butt cheeks and knelt behind me.

I felt the thick head settle against the hole. He pressed. It didn’t go in. He pressed harder. I pushed back, frightened and hungry at the same time, and suddenly the head went through and a white-hot burn shot through me that made me bite the seatback.

—Hold on —he said, still, hand on my waist—. Hold on, it’ll pass.

And it did. He pushed in little by little, one centimeter and he waited, another centimeter and he waited, until I felt his balls against my ass and knew he had all of it inside. Damián stroked my back under the sweater.

—Good, whore, good. There. You’ve got it all now.

He started moving. First slowly, coming almost all the way out and sinking back in gently, letting me feel every nerve, every vein. Then faster, gripping my hips, fucking me against the fogged-up car window where my spread hands left two sweaty prints. The seat creaked. My heels dug into the leather. I moaned in a tone that wasn’t mine, and every time he shoved in hard an “oh” slipped out of me, high and eager, and he loved it.

—Tell me what you are —he panted, never breaking rhythm—. Say it.

—A whore —I murmured.

—Louder.

—A whore! I’m a whore!

—My whore.

—Your whore.

He grabbed my hair and pulled my head back. He fucked me harder, and with his free hand he found my cock between my legs and started jerking me off to the rhythm of his thrusts. I didn’t last at all. After four or five strokes, with the other man’s cock hammering inside me and his rough hand yanking at me from above, I came onto the seat, onto my own fishnets, in long ropes that splattered the leather and Camila’s skirt. My legs were shaking, my ass clenching around him in spasms, and I heard myself whimper like I never had before.

—Oh, the whore, you clamped right down on me —growled Damián—. Like that, squeeze me, squeeze me, I’m going to come.

He dug his nails into my hips and sped up. Three, four, five deep thrusts, and suddenly he drove all the way in and stayed there, still, his cock throbbing inside my ass. I felt the latex swell, felt his spasms against my butt cheeks, felt the rough groan that came out of him pressed against the back of my neck. He came fully. I stayed on my knees, hands trembling against the glass, while he emptied into the condom and I felt everything, every shudder.

He stayed like that for a while, over me, not pulling out, breathing down my neck. Then he withdrew slowly, carefully, and I felt the emptiness like a loss. The black panties were hanging off one knee. The fishnets were torn at the right thigh. I had my own cum on the skirt, saliva on the sweater, and my ass pulsing in a way that wasn’t going away for hours.

I thought of Camila, asleep forty blocks away, in a bed from her childhood, not knowing. I thought about how tomorrow I was going to have to wash everything, press the skirt, put the heels back in their box, wipe the makeup off my face, go back to being that regular guy who goes to the gym three times a week.

But tomorrow was still a long way off.

Damián took off the condom with two fingers, tied a knot in it, and tossed it out the open window. He settled back against the seat, still with his cock out, glossy and half-soft. He looked me up and down, kneeling there, ruined, and smiled.

—Don’t go yet —he said, and ran his thumb over my lower lip, wiping away a bit of lipstick—. Rest five minutes and then get back to sucking. The night’s just getting started, doll.

I still hadn’t asked his name. He hadn’t asked mine.

There are things, I discovered that night, that are better told without names.