The Man Who Pays Me to Dress as a Woman

This city grows a different set of rules when one in the morning passes. Traffic lights blink yellow, taxis cruise empty, and the people still awake at that hour are usually looking for something they don’t dare look for by day. I’m part of that landscape. I go out walking when everyone else is asleep, not because I can’t sleep, but because at that hour hunts are easier.

I like women, that much is clear to me. But women at three in the morning aren’t available, and if they are, they charge too much or drag you into trouble. Men, on the other hand—the ones who want what I’ve got between my legs—those are always awake. Cross-dressers, transsexuals, desperate fags. I don’t care what they are as long as they pay.

—Are you awake? —it was always the same message.

It came from Mateo. Thirty-four years old, chronically single, one of those men who live in an apartment that’s too neat and too empty. I met him on one of those apps people swear they don’t use but keep installed in a secret folder on their phone. He wrote to me on a Tuesday at 4:20 in the morning with a photo that left little to the imagination: he was on all fours, two fingers shoved up his ass, his face hidden.

We only ever talked about sex. I never asked what he did for a living, where he lived, whether he had a family. He didn’t ask much either. The only thing that interested him was the size of the cock I’d shown him in the first photo, and all I wanted to know, for my part, was how much he was willing to pay to suck it.

Because that’s what I do. I charge fags. Not because I need to—I have my job, my life, my own routine—but because it seems fair to me. They want something they can’t easily find, and what isn’t easy to find has a price. Where I live, men like me aren’t common. I’m tall, dark, quiet, and between my legs I’ve got exactly what the apps ask for with eggplant emojis and exclamation points. A thick, long cock, veins standing out, heavy balls. That costs money.

Mateo and I had spent weeks talking about doing a threesome with another guy he knew. It was a plan he kept dragging along with enthusiasm and me with patience. Every time he wrote, he repeated the same fantasy like a mantra: the two of them on their knees, taking turns sucking my cock, fighting over my load. I went along with it, but I knew those plans rarely come off: someone chickens out, someone gets cold feet, someone doesn’t show. The important thing was keeping him hooked.

One night he wrote at half past three to confirm. Forty minutes later, he canceled. He said he was tired, better another day. I answered with one sentence.

—If you want me to go, this costs money.

It took him almost ten minutes to reply. When he did, he didn’t argue about the price. He agreed. He sent me the address of a hotel fifteen blocks from downtown, one of those places that charge by the hour and don’t ask names.

***

He paid for the taxi in advance, a direct transfer to my account. The room too. By the time I got there, he already had the lights low, a towel folded on the bed, and a bill on the nightstand. I took three steps to look at him properly.

Mateo was shorter than he looked in the photos. Skinny, narrow-shouldered, with a shadow of poorly shaved beard. He was nervous. His hand trembled a little when he handed me the water he’d bought.

—Want me to turn off the bathroom light? —he asked.

—Leave it —I said.

I sat on the bed, took off my shoes, and looked at him without hurrying. He stayed standing there, waiting for an order I didn’t intend to give yet. That pause, that moment when the other person doesn’t know what to do, is where everything begins. It’s the part I like most. Before the contact, before the moans, before anything else. The pause.

—Take your clothes off —I told him at last.

He did it without looking at me. He ended up in white briefs, a little too big, and awkwardly covered himself with his hands.

—All of it —I added.

He didn’t argue then either. He slid the briefs down and showed me a small cock, half hard, hanging between his thin legs. I didn’t look at it twice. I wasn’t interested in what he had. I was interested in what he was going to do with mine.

—Come here. Kneel down.

He knelt between my legs. I grabbed his head with one hand, opened my zipper with the other, and pulled out my cock, already half hard. He stared at it with his mouth slightly open, as if he didn’t know where to start.

—Suck it. All of it. No hands.

He opened his mouth and took it in. At first clumsily, clenching his teeth, choking too soon. I grabbed the back of his neck and pushed until I felt the tip against his throat. He gagged, spit saliva, coughed, and I kept him there a few more seconds before letting him go.

—Again. Deeper.

He learned. My cock got fully hard in his mouth, swollen, shining with the saliva running down his chin. I watched his face while he sucked me: teary eyes, mouth stretched around the circumference of my cock, cheeks hollowing every time he sucked. When I could no longer stand his tongue working over my balls, I yanked him up by the hair and threw him face down on the bed.

—Open your legs.

He spread them. I saw his shaved ass, tight, trembling. I spat on the hole, ran my thumb over it, opened it a little. I slicked my cock with saliva and the lube from the bottle he’d left on the table, and shoved it in all at once, to the hilt, without waiting for him to get used to it.

He screamed into the pillow. A muffled scream, more surprise than pain. I grabbed his hips and started moving without giving him a break, going in and out with long thrusts, feeling his ass clamp down every time I drove my cock all the way in to the balls.

—Take it. You asked for this.

—Yeah… yeah…

That first time wasn’t for him. It was to show him what he was going to get when he called me again. I fucked him fast, with the calculated haste of someone who has absolute control over the moment, feeling the bed creak and him moan into the sheets with every slap of my balls against his ass. I grabbed his hair, pulled his head back, and fucked him the way you fuck someone you already know is going to ask for more. Ten minutes in, I pulled out without warning. My cock was hard, shining, and his ass stayed open, throbbing, with a thread of saliva and lube running down the crack.

I pulled out, dressed, grabbed the money from the table, and left before he could ask me for anything else. I left him gasping face down, cheek pressed to the sheet, and from the hallway I still heard the phrase I’d been expecting.

—Come back.

***

It took him a week to write me again. I didn’t message him. That’s another part of the game: making yourself wanted, not answering messages right away, letting the other person think they don’t interest you anymore. When the message finally came—a Friday at 2:40 in the morning—I left it on read for an hour before answering.

—I want to see you again —he wrote—. Whatever.

—This time you’re going to do something different.

—Whatever you say.

I sent him instructions by voice note so he couldn’t reread them and chicken out. I told him to buy a wig, women’s underwear, a short dress, stockings. I told him the approximate size, the color, and I told him that when he got to the hotel I wanted him to look like someone else. I didn’t care whether he did it well or badly. I just wanted to see him trying. And I told him one more thing: to prep his ass before I got there, to get his fingers in with lube until he could take three, because that night I was going to give it to him without mercy and I wasn’t going to wait for him to get used to it.

—Are you sure? —he asked by message.

—You’re the one asking. I tell you what it costs.

***

I got to the hotel twenty minutes late. I did it on purpose. The door was ajar and I pushed it open without knocking.

Mateo was sitting on the bed, dressed the way I’d asked. The wig was black, straight, falling to his shoulders. The dress was red, tight, with a neckline that didn’t suit him because he had nothing to offer up there. The stockings reached halfway up his thighs. He’d done his makeup, badly, but he had done it. His eyes were lined and his mouth painted a pink that went with nothing.

I stopped in the doorway and looked at him. He lowered his head.

—Look at me —I said.

He raised his face. He was ashamed, but there was something else too. A mix of humiliation and hunger I know well. People who are ashamed of wanting something want it twice as much.

I stepped closer, took his jaw between two fingers, and lifted his chin.

—Today you’ve got a different name —I said—. Today you’re not you.

—What’s my name?

I made up some name on the spot, a woman’s name that came to me. He repeated it. I made him repeat it several times until it sounded natural.

Then I told him to kneel.

***

He knelt between my legs, the red dress wrinkling against the floor. I opened my zipper, pulled my cock out, and pressed it against his painted mouth.

—Open. And don’t close your eyes. I want to see your face while you suck me.

He opened up. I shoved my cock halfway in and left it there. He looked at it with wide, dazed eyes, tongue working under the head. Then I started moving, slowly at first, fucking his mouth like I’d fuck a cunt, one hand holding the back of his neck and the other smearing his mascara as I ran my thumb over his cheek. Saliva dripped down his chin and pooled in the neckline of the red dress. The lipstick smeared, leaving pink stains around the base of my cock every time I pulled it out.

—Deeper. Swallow it all.

I pushed his head forward. He gagged, his eyes filled with tears, the makeup running in two black streaks. I didn’t let him go. I rammed my cock down his throat until I felt his nose against my balls, and there I held him, counting under my breath, until he started gagging. Only then did I let him breathe.

—Good girl —I told him, using the fake name—. Like that.

He opened his mouth again without being asked, tongue out, panting. I spat inside, slid two fingers in, stroked his throat from the outside. Then I hauled him up by the hair and threw him on his back on the bed.

I lifted the red dress up to his armpits. Under it he had on a ridiculous white women’s thong over that little wrinkled cock. I pulled it aside, grabbed his legs with the stockings behind the knees, and spread them wide. The ass was shining with lube, just as I’d ordered. He’d prepared himself well.

—Ask for it.

—For what?

—Ask for it. With the new name. Tell me what you want.

—I want… I want you to fuck me.

—Fuck what?

—Put your cock in me. All of it. Fuck my ass until you cum inside me.

I put the tip against the hole and pushed. It opened without resistance, swallowing me to the base in one continuous motion. He moaned long and high, mouth half open. I started moving hard from the first moment, giving him deep thrusts that shook his whole body against the mattress. The wig shifted, started to twist, the black hair covering half his face.

I fucked him for almost an hour straight, without pauses, without condescension, without the tenderness you give a woman when you want her to come back. I fucked him the way you fuck someone who knows he’s paying for exactly that. Face down after that, cheek pressed into the pillow, stockings half fallen, dress hiked up to the waist. I shoved my cock in to the balls and he clutched the sheets with both hands, the wig almost off now, biting the pillowcase so he wouldn’t scream too loud. I grabbed his real hair beneath the twisted wig and lifted his head so I could see his face while I fucked him.

—Look at yourself in the mirror. Look at what you turned into.

Next to the bed was a big, crooked mirror with a chipped frame. He turned his face and saw himself: the wig hanging off one side, makeup ruined, the red dress wrinkled at the waist, my cock going in and out of his open ass. He tightened around my cock all over.

—Oh my God, oh my God, oh my God —he kept repeating like a broken prayer.

I like that phrase. I’ve heard it so many times it doesn’t mean anything in particular anymore. Fags say it when they don’t know what else to say, when their body turns into an instrument they can’t control. They say it as they might say anything else. But they say it.

The wig shifted at some point and I let it fall to the floor. I drove my cock deeper, faster, until I felt my balls tighten and my whole body tense. I came inside him the first time, with short, furious thrusts, unloading semen deep inside while he moaned without a voice, mouth open against the pillow. I felt my cock throbbing inside him, emptying, and I didn’t pull out until the last contraction faded.

I pulled out slowly. A white thread ran from his open ass to the back of his thigh, sliding down the stocking. I flopped onto my back on the bed, lit the joint I’d carried in my pocket. Mateo stayed lying face down, panting, motionless, his ass still open and dripping. I watched his back rise and fall. I ran a hand through his hair—his own, the real one, under the fallen wig—and didn’t say anything.

I smoked slowly. I offered him some; he took it. We shared the joint like old friends, in silence, and for a moment it almost seemed like this could be something else. But it wasn’t.

Twenty minutes later I turned him face down again.

The second time was longer. Not so rough, more methodical, almost systematic. I lifted his hips, put a pillow underneath for a better angle, and entered him again, this time with his ass already fucked and still full of my cum from before. I pushed in slowly, feeling the semen run down the shaft of my cock as I went in. I fucked him with the rhythm of someone who takes his time because he knows the other person won’t complain. I whispered things in his ear I hadn’t said before. I called him by the fake name I’d given him. I asked if he liked being someone else for a while.

—Yes —he said.

—Say it better.

—I like it.

—Louder.

—I like it. I like it. I like it.

—What do you like? Say it all.

—I like you fucking me. I like being your slut. I like paying you to fill my ass.

I grabbed the back of his neck, squeezed a little, not enough to hurt him. I drove my cock in to the hilt and stayed there, moving my hips in circles, letting him feel every millimeter inside. Then I started fucking him again, long and steady, until he began moving against me, pushing his ass back on every thrust.

—That’s it. Move. Earn your load.

He moved. With the red dress wrinkled at the waist and the stockings slipping down, he shoved his ass against my cock like a bitch in heat. His little cock slipped out of the shifted thong, and I saw him grab it with one hand and jerk himself frantically to the rhythm of my thrusts.

—Don’t you cum. You cum when I tell you.

He let go of his cock at once. I slammed into him another hundred times, sweat running down my back, hearing him moan higher and higher, more and more surrendered. When I couldn’t hold out any longer, I pulled out hard.

—Turn over. Open your mouth.

He turned quickly, sat on his knees in front of me. I told him to open his mouth. He did it without thinking. I shook my cock twice over his face and started coming into his mouth, long ropes of semen filling his tongue, dripping down his chin, staining the already ruined lipstick. I gripped the back of his neck so he wouldn’t close his mouth, so he’d take it all. When I finished, I put two fingers in, dragged the cum hanging from his chin, and fed that to him too.

—Swallow. All of it.

He swallowed. He swallowed it all, just as I’d warned him over text weeks before. Then he opened his empty mouth to show me. That part was important. That part was the contract.

***

After that I got dressed slowly. I washed my hands in the bathroom, splashed water on my face, and looked at myself in the mirror. When I went back to the room, Mateo was still lying back, still wearing the stockings, makeup smeared, eyes closed. A thread of semen was still running out of his ass, soaking the sheet.

—The money —I said.

He pointed to the drawer of the nightstand without opening his eyes. I opened it, counted the bills, and put them in my back pocket.

—When are we seeing each other again? —he asked, still not moving.

—When you write me.

—I’m going to write you.

—I know.

I paused a second at the door. I looked at him one last time. There was something pathetic and something beautiful about him at once, that figure lying on the bed with the wig fallen to one side and the mascara running. Something that probably shouldn’t exist and yet did. Something that paid for the right to exist.

I closed the door behind me.

I went down the stairs, nodded to the doorman, stepped out into the street. The city was still asleep. Less than an hour remained before dawn. I lit a cigarette on the sidewalk and walked toward the avenue without hurrying.

He’s going to write me again. When he does, I’m going to take three days to answer. The price is going to go up a little each time.

That’s part of the deal too. He knows it, I know it. That’s why he pays.

At five in the morning I sat down in a twenty-four-hour bar and ordered a coffee. I counted the money under the table, unseen by anyone. It was all there, as always.

I took out my phone, opened the app, and started looking to see who else was awake at that hour.