The Crossdresser Hiding in Me

I don’t know exactly when it started. It’s easier for me to say when it started to matter.

I was forty-one years old, working as a security guard in a shopping center shut down by the pandemic, and living alone in the apartment I’d shared with Mónica for twelve years. She had gone off with her parents to her home village as soon as the state of alarm was declared. I stayed. The apartment was big for one person, and the silence weighed on me in a way I hadn’t expected.

The first weekend I opened Mónica’s closet. Not for the first time.

***

To understand what happened during that confinement, you have to understand what I’d had inside me long before.

I’m a man with no visible mystery. Five foot seven, one hundred and eight kilos, forty-three years old when all this happened. I’ve got a round face and a receding hairline I decided to accept a long time ago. No one seeing me on the street would think anything in particular. I’m the guy standing behind you in the supermarket, the one patiently waiting for the elevator, the neighbor who says hello in the entryway.

What no one sees is that under my work clothes, sometimes, I wear lingerie.

Not always. Not even often. But sometimes.

It started when I was sixteen. We lived in an apartment block, and the neighbor on the fifth floor hung her laundry on the terrace overlooking the inner courtyard. One summer afternoon, from my window, I saw her hanging, among towels and shirts, a collection of lace underwear in various colors: pink, black, red, with details I couldn’t make out clearly from that distance but that my imagination filled in without difficulty. I don’t know how long I stood there looking. Long enough for a question to form in me that I wouldn’t know how to put into words until much later: what would it feel like?

I didn’t do anything with that question for years. I went on functioning like any other man around me. The girlfriends I had, the job, the life expected of someone like me. But the question was still there, dormant, waiting for me to pay attention to it.

The first time I paid attention to it I was twenty-six and spending a week alone in the apartment while Mónica visited a friend. In the drawer of her nightstand there was a set of underwear she hadn’t worn yet: black lace panties and a matching bra. I took them, put them on, looked at myself in the bathroom mirror. My cock got hard immediately, pressed tight against the lace, pushing the fabric forward until the tip showed over the elastic. I grabbed it over the panties and worked it slowly, feeling the lace rub against my balls. It didn’t last long. I came, staining the inside of the panties with a thick rope that seeped through the lace. I took them off, rinsed them in cold water in the bidet for twenty minutes until there wasn’t a trace of semen left, wrung them out, and left them drying on the radiator. The next morning I put them back in her drawer as if nothing had happened.

What I felt in those five minutes in front of the mirror stayed with me for weeks. A mixture of things I didn’t know how to separate: excitement, shame, curiosity, and something harder to name. A kind of recognition. As if the mirror were showing me something that had existed for a long time without my ever looking it in the face.

Over the years I built it in secret. I bought clothes in stores where I paid in cash, kept them in a bag at the back of the closet, and wore them when Mónica wasn’t home. Always the same cycle: excitement, pleasure, shame as soon as the heat wore off, a promise not to do it again. And then all over again.

The fantasies I built around all that changed over time. At first they were seen from the inside: just me, the mirror, the question of how I’d look to someone from the outside. In time they began to include other people. I imagined someone opening the door and finding me dressed like that. That person not horrified, but looking at me in a way I recognized even though I had never received it from anyone. Pushing me against the wall and slipping a hand under the skirt to grab my cock over the panties. Forcing me to my knees, opening the fly of my pants, and shoving his dick all the way down my throat.

There was something about the fantasy of being seen that intensified everything. It wasn’t enough to put the clothes on. What excited me was imagining the effect I had on someone else. Having my stuffed tits looked at and seeing them get hard thinking that the tits were fake but the ass was real and ready to be fucked.

Carnival gave me an outlet I used with more care than anyone around me could have imagined. I bought wigs months in advance, practiced makeup at home with YouTube tutorials, chose clothes with the judgment of someone who knows exactly what he’s looking for. I went out with several beers in me and the feeling that for a few hours I could be somebody else. They looked at me. Men who under other circumstances wouldn’t have spoken a word to me made space for me at the bar and asked me my name. When my voice gave the game away, some of them got flustered. Others just smiled.

One of them asked for my phone number anyway.

What I discovered on those nights was something I hadn’t expected: my body, with the weight it had picked up since I was thirty, produced a certain effect when dressed the right way. The broad hips that made me look bulkier than I should as a man turned into something people looked at when I wore a fitted dress. The chest I’d developed over the years, which I’d always seen as a problem, took on a shape with a padded bra that stopped embarrassing me. It was the same body as always, seen from another angle.

I never forgot that feeling.

***

When confinement began, I held out for two weeks as best I could. Then I opened Mónica’s closet.

She and I had similar builds: she was five foot five and had the generous body that comes with age and good food. Her clothes fit me with differences: tighter at the shoulders, looser at the hips. But they fit. And on me they produced effects that kept surprising me every time.

I spent weeks dressing every day, without the urgency of before, without the fear that someone might turn up unexpectedly. I took photos of myself with my phone: the cleavage, the back, the legs in black fishnet stockings. I recorded myself walking down the hallway in the heels I found at the back of the closet. I lay on the double bed with my panties pulled down to my knees and my dress hitched up to my waist, and I jerked off with both hands: one on my cock and the other slipping two saliva-slick fingers into my ass, imagining it was something else going in. I came up to five times a day, some of them against the closet mirror so I could watch my face while semen ran down my thighs, staining my stockings.

I masturbated looking at those photos with a clarity of purpose I hadn’t felt about anything in a long time. I also discovered that if I licked my finger and ran it over my nipple through the lace bra, the sensation shot all the way to the tip of my cock as if everything were connected by a wire I’d never known existed.

The curiosity about whether it would have the same effect on other people came one rainy night, after I’d already been alone a month. I created a profile on a dating app. I uploaded four photos. No face, nothing identifiable. Just the body, the lingerie, the brown wig I’d bought years ago for Carnival.

In twenty-four hours I had fifty-three messages.

I stared at the screen not quite knowing what to do. Men of all ages writing things that ranged from outright obscene to unexpectedly tender. Young guys sending photos of their hard cocks like business cards, some still dripping, with the foreskin half pulled back and their balls tight in the frame. Middle-aged men with established lives writing long paragraphs describing what they’d do to me: how they’d bend me over, how they’d fuck my mouth until my makeup ran with tears, how they’d come inside me and leave semen running down my legs. Older men asking only to talk, only to listen, only to know there was someone on the other end.

I answered some of them. I made up a coherent story: I lived alone, worked from home, wanted to get through confinement in a more entertaining way. None of them asked too much.

I gave myself a name. Silvia. No special reason, just that it sounded like someone who knew what she wanted.

Over time, Silvia took shape beyond the name. She had a different voice in messages: more direct, less roundabout than mine. She knew what she wanted and said it without apologizing. She wrote things like “I want you to fuck me to the hilt” or “I like being called a bitch” without hesitating. In that, I thought more than once, she was pretty much like the person I’d always wanted to be.

Among all the men who wrote, there was a type that kept repeating with a frequency I hadn’t expected: truckers. Men on the road who kept working while the world stopped, with long hours on the highway and nights in the cab at some service area. They wrote at any hour, from their phones, with short messages at first and longer conversations later. They sent photos from the driver’s seat, the steering wheel in the background, a hand down their pants, their cocks peeking above their belts. The cab was the only private space they had.

There was something about them that connected with me in a way I took time to understand. Maybe it was the discretion they all needed: none of them could afford for anyone to know, just as I’d gone years without being able to afford anything for myself. Maybe it was the shared loneliness, the feeling of being outside normal life while normal life was at a standstill. Or maybe it was simply that they were direct, without pretension, not asking for more than what was there.

With one of them, Emilio, I talked for more than three weeks straight. He sent me voice notes from the road, the engine rumbling in the background, telling me in that rough voice of his, worn down by sleepless hours, everything he’d do to me if he had me in the bunk. “I’d suck your tits over the bra, Silvia, until it was soaked through. Then I’d pull down your panties with my teeth and eat your ass until you begged me to fuck you.” I answered with photos or voice messages in which I tried for a softer tone than my own, cock in hand, describing how I was sliding a dildo I’d bought online into myself while we talked. We never actually met up. It wasn’t necessary for that daily exchange to become something I looked forward to every night.

When the restrictions eased in the summer, I met another one. He arranged to see me at a rest stop thirty kilometers from where I live. I drove there with the wig pinned up, a black spaghetti-strap dress that belonged to Mónica, and low heels that gave me just the right amount of height. Underneath, black lace panties, thigh-high stockings, and nothing else. My hands trembled on the wheel but I didn’t turn back.

I parked beside the truck, a white semi with the cab curtains drawn. I sent him a message. “I’m here.” The passenger door opened and a hand gestured for me to climb up. I got in. Inside it smelled of old smoke, cold coffee, and a man’s sweat. He was fifty-something, graying beard, plaid shirt open to the third button, a big belly and thick arms from lifting things all his life. He looked me over in silence, calm as someone who already knew what he’d come for and wasn’t in any rush.

“Pull your dress up,” he said.

I did. I hiked it up to my waist, leaving the lace panties in view and my cock outlined underneath. He smiled and put his hand on me, squeezing me through the fabric.

“What a surprise,” he said, though both of us knew it wasn’t any surprise. I’d told him by message a week earlier.

He slipped his hand inside my panties and pulled my hard cock off to one side. He worked it with his rough palm, spitting into his hand so it would glide better, while with the other he squeezed one tit over the dress, searching for the padded bra and chuckling softly when he found the nipple underneath, real, hard. He bent down and sucked it through the fabric, biting it carefully, leaving a wet ring on the black dress.

“Get on your knees,” he told me.

I slid to the cab floor, between his seat and the steering wheel, a narrow gap where I barely fit. He opened his pants without ceremony. Out came a thick cock, shorter than fantasy would have liked, but broad, with dark skin and heavy balls hanging over the lowered underwear. He grabbed my wig with one hand and brought me closer to his face.

“Open up,” he said.

I opened my mouth and he slid into it slowly the first time, watching me, and after a couple of back-and-forths he started pushing all the way down, down my throat, until tears filled my eyes and my makeup began streaking down my cheeks. I sucked him off the way I’d spent years imagining I’d suck someone off: tightening my lips around the head, pulling back to lick his balls one by one, running my tongue all the way up the length, taking him back in until I gagged. He held the wig in place so it wouldn’t fall and kept the rhythm for me, breathing hard through his nose, murmuring things: “That’s it, bitch, that’s it, suck my cock, take it all.”

After a while he made me stand up. There wasn’t room in the cab, so he braced me against the passenger seat, face down, with my knees on the seat and my heels hanging in the air. He hiked my dress up to my back and pulled my panties down to mid-thigh. He spat, smeared my asshole with his fingers, and then with more saliva, and then with a tube of lubricant he pulled out of the glove compartment like someone who always had that sort of thing handy.

He put one finger in first, then two, unhurriedly, until he felt me give. Then he got behind me and pushed. His broad cock opened me slowly, with a burning that made me grit my teeth, and kept pushing until I felt him all the way inside, resting against the back of me. He stayed there for a moment, breathing on my neck.

“What an ass you’ve got, Silvia,” he said. “What a bitch’s ass.”

He started fucking me slowly, pulling almost all the way out and shoving back in, while with his other hand he reached around to grab my cock and beat it off at the same rhythm. The cab rocked with each thrust. The windows fogged up from the inside. My face was crushed against the seat upholstery, the wig crooked and one cheek slipping in my own spit, and even so I wouldn’t have wanted to be anywhere else.

When he sped up I knew he was coming. He grabbed my hips with both hands, digging his thumbs in, and drove in three or four good times all the way to the hilt. I felt the heat of his cum inside me, a hot burst that stayed there, and he stood still for a while before slowly pulling out. Semen began dripping down the inside of my thigh, over the stocking. He worked my cock with his hand until I came across the seat, one jet splattering against the upholstery and another weaker one hanging from my fingers.

What happened lasted less than two hours. I sat in the car before driving off and looked at myself in the rearview mirror. The wig was crooked. The makeup hadn’t survived completely. There was a red mark on the passenger seat from my cheek and I could still feel the other man’s cum running down inside me. But what I saw in the mirror wasn’t shame. It was something else that still didn’t have a proper name, but it was pretty damn close to calm.

***

Confinement ended. Mónica came back. Four months later I asked for a divorce, unable to explain exactly why, though I knew perfectly well why.

Living alone gave me the freedom to arrange things my way. For the first few months I dressed more often than I had ever allowed myself before. Over time that frequency settled: there are weeks when I don’t do it, and that’s fine too. It no longer comes with shame.

Silvia didn’t disappear. She’s still on the app, in the wig stored on the closet shelf, in the lingerie that’s now mine and that I buy without rushing.

I still meet up with men from time to time. Some live in the city and come up to the apartment, where I have the big mirror and the sheets I no longer share with anyone, and they fuck me on the bed with the easy confidence of men who know no one will interrupt. Others are just passing through, with their truck parked in the industrial estate and a few hours free before the next run; for them, the cab is enough, with the curtains closed and Silvia kneeling between the steering wheel and the seat, sucking them off and letting them fuck her ass until they come and drive away.

Those are the ones who come back the most.

I don’t need to understand everything to know it works. I just know there’s a version of me that shows up from time to time, that her name is Silvia, that she wears fishnet stockings and a brown wig, and that certain truckers look for her when they pass through here.

And that, for now, seems enough to me.