The Night I Had to Dress Up as a Woman

Let me introduce myself: back then I called myself Camila, my girl name. I had just turned eighteen, had just started university, and was in my first term. Since I was fourteen, I liked to sneak into my mother’s and my sister’s clothes. I was fascinated by lingerie, by everything feminine, by the feel of a stocking against my skin. But it was a secret I guarded with claws and teeth. No one, absolutely no one, could know.

At the university, our classroom was a cross-section of people: teenagers like me, others already older, all mixed together. As always happens, a group of friends formed, and on weekends we’d go out to get lost among parties, gatherings, and drinks. One of those nights, four of us —Tobías among them, my best friend— went downtown. It was a hot area, full of bars, clubs, and nightspots that drew people of every kind.

After midnight, emboldened by alcohol, we were wandering aimlessly when we came across a gay club. At the door stood women of a beauty that left us speechless: dresses clinging to their bodies, carefully made up, posing in ways that promised things we couldn’t even name. It took me a second to realize they were transvestites and trans girls, fighting to get into the place. Some were alone, others on the arm of a partner, and all of them were moving through a sea of guys looking for the slightest lapse to brush against them.

I saw Tobías staring at them, dumbstruck, mouth slightly open. He said nothing. We kept walking and called it a night, but something had lodged itself in both of us.

***

The following week, a coincidence left Tobías and me alone in the library, finishing a research assignment. During one of those pauses I asked him, pretending not to care, what he had thought of Friday night’s outing. He talked to me about downtown, the bars, but he completely dodged the club. I had to be more direct.

—What caught my attention was that gay place —I blurted—. And the girls standing at the door.

His face changed. He lowered his voice, as if someone might hear us between the shelves.

—They impressed me too —he admitted—. They’re huge, gorgeous.

—Did you know they were trans? —I asked.

He looked at me mockingly.

—I’m not stupid. Of course I realized they weren’t women. But they seemed like the sexiest things I’ve ever seen in my life. I couldn’t stop thinking about that place. I didn’t tell you because I didn’t want you to think I was queer.

I laughed so hard they kicked us out of the library. Once we were in the street, on the way to catch the bus, we kept talking about it. Between jokes I threw out the proposal:

—Why don’t we go one day and check out the club from the inside? Get a close look at those girls.

To my surprise, Tobías nodded, eyes shining. We agreed to go on Friday.

***

The day came, and I was so anxious I could hardly wait. We met up early and gave the moment some flavor with a bit of alcohol. Between drinks we joked that, if we were lucky, we might even pick up a trans girl. For both of us it was a hidden fetish that suddenly seemed about to come true. We even split the loot before catching it: I wanted a blonde, he wanted a brunette with long hair and endless legs.

—Those flesh-colored pantyhose and tiny skirts really got me hot —Tobías confessed, already tipsy—. All made up, showing off for everyone. With those hard cocks outlined under the dress, brother. Thinking about it drives me crazy.

We drank and talked for almost two hours, until midnight found us climbing into a taxi bound for the club.

When we got out, it was after one in the morning and there were about thirty people packed at the door, all fighting to get in. That should have made us suspect it wouldn’t be that easy. We saw four trans girls crossing the entrance and three others a few meters away, chatting and smoking cigarettes with an unmistakable smell. When we reached the door, two huge men stopped us.

—What do you want? —one of them said.

—To get in, meet people, have fun —I answered. Tobías wasn’t even able to open his mouth.

—Only trans girls and crossdressers get in here, alone or with their partners.

Between fear and disappointment, I tried to negotiate:

—Isn’t there any exception?

The bigger one looked at me and, seeing my face, softened his tone.

—Look, kid, you’re not even of age yet. Only the girls and their partners get in here. This place is very discreet and we don’t want trouble. If you want to get in, you have to come invited by a member, and even then you pay admission and minimum spend at the table.

—How much would that be? —we asked almost in unison.

The bouncer laughed.

—Thirty dollars per head for admission and another fifty in minimum spend. Each.

We looked at each other. Between the two of us we had, if we were lucky, thirty dollars. Impossible. We stepped away from the door and stood a few meters off, cursing our bad luck.

—I’m going to try to convince him —Tobías said suddenly—. Let’s see if he lets us in for even a few minutes with what we’ve got.

—I’ll wait here. I don’t want to be humiliated again.

***

Seeing him so determined shocked me. Tobías was almost twelve inches taller than me, and it showed that he was willing to do anything to be part of that carnival. From a distance I watched him beg, one by one, at the people going in. He even talked to the girls, asking them to let him in. Everyone turned him down. I felt sorry for him.

And it was then, while I was watching him fail, that a mature trans woman with a calm gaze came up to me.

—If you want to get into that club —she said—, you’ll have to be more creative.

I was speechless. I could only listen. She explained that the moment she saw us she knew it was an impossible mission: just two students with no money, out of their element. But seeing my friend so determined, she thought she had the solution.

—To get in, you need a trans partner to bring you in. That saves you the admission, the minimum spend, everything.

—Thank you —I replied, still dazed—, but I wasn’t planning to go in with you, if that’s what…

The woman burst out laughing, set her cigarette aside, and gave me the answer that would mark the rest of my life.

—You misunderstood me, sweetheart. What I’m proposing is a transformation session for you. You be the cross girl who goes in with your friend.

I froze.

—From the moment I saw you I realized you could pass for one. You’re smaller than him, you have delicate features. With a little makeup, a corset, and some padding, you’d be a real little girl.

I said nothing. I looked at her, not knowing what to answer. She put a piece of paper in my hand.

—I do transformation jobs. There’s my number, if you’re interested.

And she left with her friends, leaving me more confused than ever. Was it that obvious? Could people tell I dressed like a girl? Was I not as discreet as I thought? Everything turned upside down for me. Tobías came back defeated, said something about the woman who had spoken to me, but I barely answered. We walked to a taxi and I went home mute, under his questioning gaze.

***

On Monday, in class, one of the professors was absent and Tobías took the chance to complain about Friday’s failure. I answered with monosyllables until he confronted me hard:

—What’s wrong with you? You’ve been acting weird since Saturday.

I hesitated a few seconds.

—That woman at the door told me something that got me thinking.

Big mistake. He wouldn’t let me alone for two days. In the end he forced me to tell him, though I changed things a little: I told him the woman had explained there was no way to get people our age in, except through one method of hers.

—What method? —he jumped in, suddenly hopeful.

I took a deep breath.

—One of us dresses as a woman. Makeup, wig, everything. And we go in as a couple.

Tobías laughed out loud. Then, all of a sudden, he fell silent.

—It’s not that crazy —he muttered—. But the thing is, it would have to be you. I’m much taller and broader. You’d look natural. That way we get in without anyone suspecting, and finally we’re next to those girls.

He asked for the phone number the woman had given me. I handed it over. He snatched the paper from my hand and said he was going to call her to find out if it was true. That’s how Monday ended.

***

On Tuesday he caught up with me when I left the university, eager. We walked a few blocks.

—I called her last night —he told me—. Her name is Selene. She’s trans; she used to be a showgirl at that same club in its heyday. Now she only does transformations and sells those cigarettes at the door.

He watched me, afraid I’d refuse, but I was as determined as I had been that night.

—She says that if we get in, we could even go to the VIP area, where couples have their moments in front of everyone. Without spending a cent, all discreet. She’d do the crossdressing job on you: padding, corset, makeup. You’d look like just another girl.

—You’re crazy —I told him—. I’m not doing it. If you want it that badly, dress up yourself and I’ll go with you.

But he reminded me again of the size difference, how broad he was, how much I still looked like a boy. I told him I didn’t dare. Then he begged me. He would pay for everything. That he owed me hundreds of favors, that he’d always had my back when people picked on me. That it would be just once.

—And how do I dress, how do I do my makeup? That takes hours.

—Selene does everything at her place. She even provides the clothes. For a first time, it’s less than thirty dollars.

—I’m not putting on heels like those girls.

—Women’s sneakers, jeans with hip padding, a tight T-shirt, wig, and makeup. The rest is done by the darkness of the night.

He had an answer for everything. Afraid, but also with a horny curiosity I couldn’t deny, I said yes. We agreed that on Friday I’d go to Selene’s place at eight, and by eleven I’d be ready. Everything coordinated, and I still didn’t understand how I’d gotten myself into this.

***

On Friday at seven I arrived at Selene’s house. She greeted me with a warmth that undid me and told me everything was already paid for. She led me into her bedroom, and when she opened the door I found a true boutique: wigs, shoes, clothes, lingerie, corsets, silicone breasts, and fake hips piled in a huge room with a sweet, stale smell.

—Take off all your clothes and put this robe on —she ordered.

I looked at her without moving, expecting her to leave. She didn’t.

—Girl, we have to work on your body, wax you, bathe you. Don’t get shy on me.

Her voice was firm. I started undressing with shaking hands. I took off my shirt, my pants, and was left in my underwear in front of her. Selene looked at me without the slightest modesty, with the faintest smile, like someone assessing a piece of work. I pulled down my underwear and stood completely naked. I felt the blood rush to my face and to another place too: to my shame, my cock started to swell slightly, betraying me, hanging between my thighs with a new weight.

—I knew it. You almost look like a girl. And today you’re going to look even more like a woman. Lucky for you, you hardly have any body hair.

She came closer and slowly circled around me, looking me up and down. Her hands moved over my shoulders, down my back, and stopped at my ass, squeezing the flesh with expert fingers that knew exactly what they were doing.

—You have a gorgeous little ass, round like a girl’s —she murmured against my ear—. Your friend is going to have a hard time keeping himself under control tonight.

Her words hit me right in the crotch. My cock went hard all the way, pointing forward, impossible to hide. I tried to cover myself with my hands but she gently moved them away.

—Don’t hide it, my love. There’s nothing to be ashamed of here. All girls get like this the first time. In fact, if it didn’t get hard, I’d be worried.

She led me by the hand to the bathroom with the same shameless ease with which one takes a client to a table. The shower was large, with green tiles and a huge head. She turned on the hot water and made me get in. Then, without hesitating for a second, she started taking off her dress. She stood naked too, and for the first time I saw her entire body: big firm silicone tits, a narrow waist, the hips of a mature woman, and between her legs —to my astonishment— a cock thicker than mine, brown, hanging heavy between toned thighs.

—Don’t make that face —she laughed—. Or did you think I came from another planet? All the girls at the club have one between their legs, my love. That’s the first thing you’re going to have to learn tonight.

She got under the spray with me. Her body pressed against mine burned my skin more than the water. She grabbed the sponge and liquid soap and started lathering my chest, arms, and stomach with slow circular motions. Then she lowered her hands and closed them around my hard cock, squeezing it with a firmness that tore a moan out of me.

—Selene… —was all I managed to say.

—Shhh. Relax, my love. This is part of the job too.

She washed it calmly, moving her fist up and down, playing with my balls, gently pulling back the foreskin until she’d uncovered me completely. I leaned against the tiles because my legs were giving out.

—Look at that pretty little cock you’ve got —she said in the deepest voice—. Small, yes, but standing up hard as a rock. Perfect for hiding under a thong. But if I let go now, my love, you’ll spend the whole night with your dick standing up under the dress, and it’ll show. Better I empty you once here, so you’ll be calm outside.

She crouched without taking her eyes off me, knelt under the spray, and took my cock all the way into her mouth. I felt it hot, tight, her tongue wrapping around the head, sucking with a technique I had never known. Selene sucked me slowly at first, drawing the cock out to the tip, kissing it, licking my balls one by one, and then taking it back down to the base until I felt her throat closing around me. The water fell over us, warming everything. My legs were shaking. I grabbed her wig with both hands without meaning to, and she let me hold it.

—Like that, my love —she whispered, pulling away for a second—. Grab me the way a man would. Fuck my mouth, go on.

She swallowed me again and sped up. I, emboldened, started moving my hips, pushing my cock against her palate. She moaned with her mouth full, sucking hard, and with one hand she squeezed my ass, sliding a finger between my cheeks, feeling around.

—Selene, I’m going to cum… —I panted.

She took my cock out of her mouth for just a second, never stopping stroking it with her fist.

—That’s what I want, my love. Cum all over my mouth. Then it’s my turn.

She took me into her mouth again, now to the hilt, and pumped fast. A few seconds later I came in her mouth in a long stream, moaning like a whore, feeling her swallow every bit without losing a drop. She pulled my cock out slowly, sucking it to the end, squeezing my balls with her other hand, and smiled at me with glossy lips.

—Oh, how delicious, baby. And what a load. With how worked up you were, it was about time.

My legs were trembling. She stood up and pressed her body against mine. Her hard cock dug into my stomach, thick and hot.

—Now it’s your turn. You need to learn how to suck it, because if you end up in VIP tonight you’ll need to know how. Kneel down, my love.

I knelt without thinking, with water pouring over my head. Her brown cock was in front of my face, thicker than mine, the head swollen and shining under the shower. I had never sucked one in my life, but I opened my mouth anyway and took it in. Selene guided my head with both hands, teaching me the rhythm.

—Like that, my love. Tongue down, careful with your teeth. Suck slowly. That’s it, that’s it. Now a little deeper. Yes, you’re a gorgeous little girl sucking cock. Look at you, you’re already a total slut.

Her words made me ashamed and horny at the same time, and I felt how my cock, freshly emptied, began swelling again between my legs. I sucked her as best I could, choking a couple of times, tasting the salty head on my tongue, the smell of hot cunt mixed with soap. Selene moved softly, fucking my mouth carefully, letting the head bump my throat until I felt her getting harder and heard her panting.

—Take it all, my love. Just like I did to you. Come on, you’re a nasty little slut, I want to see you swallow my cum.

She came in my mouth in hot, thick spurts, one after the other. I choked at first, but swallowed most of it, the rest running from the corner of my lips. She laughed, pleased, and wiped my chin with her thumb before sliding a finger into my mouth for me to suck.

—Welcome to the club, baby. Now then, I’ll finish bathing you and make you beautiful for your boyfriend.

She finished soaping me up all over with the patience of an old professional. She washed my ass, opening me with her fingers, running the sponge between my cheeks, and for a second I felt one of her fingers pressing lightly at my entrance, testing the resistance.

—Nice and tight. Virgin back there, huh? —she murmured—. That’s going to be very useful, my love. But not today, today is just training. The first time that little ass gets opened, I want it to be by a good man, not by my little tickles.

She spread depilatory cream over my legs, my arms, and that sparse patch of pubic hair, and a few minutes later she rinsed it off, leaving me smooth as a doll. My cock, with not a single hair around it, looked even smaller, almost girlish. She took me back to the room wrapped in a towel and rubbed creams all over my body, massaging my legs, my ass, my chest, until my skin shone. Half an hour later I was sitting in front of a mirror at a vanity table, my legs still trembling, ready for the transformation.

She began with a liquid foundation she spread over my face. She smeared my eyebrows with a stick glue, let it dry, and covered them completely. Then she applied powders that slightly darkened my skin tone and erased the trace of my brows. With a pencil she drew new ones, fully feminine. Shadow, contour, a long-wear lipstick with gloss, and she curled my lashes. She found a dark brown wig and pinned it in place over my hair.

When I looked at myself in the mirror, I wasn’t me.

She fitted me with silicone breasts that went on like a T-shirt, and I felt the strange and at the same time familiar weight on my chest. Then she handed me a tiny black lace thong and pulled it up on me herself. When the fabric reached my crotch she gently took my cock —half hard again— and tucked it back between my cheeks, holding it in place with a very tight corset that flattened everything. When she was done, between my legs there was nothing, just a smooth line where my cock had been.

—See? Like that, you can’t even tell. Even if you get hard a thousand times, nobody’s going to know. But you’ll feel it there behind, throbbing between your cheeks, all the time. It’ll be your little secret.

She slid a pair of sheer light-brown pantyhose up my legs, moving them with deliberate slowness, inch by inch to my waist. The feel of nylon on freshly waxed legs raised goosebumps all over my body. She pulled a pink mini dress with thin straps over my head and arranged it on my hips, tugging it so it would cling properly. Then she had me stand up.

—You have beautiful legs. They don’t deserve to be hidden in pants.

She looked me over, satisfied, and pinched one of my cheeks gently through the dress.

—You’ve dressed as a woman before, haven’t you?

In my excitement, the truth slipped out.

—Yes. My mother’s and my sister’s clothes, their heels, their dresses. I was fourteen.

—I knew it.

She went out and came back with black high-heeled shoes with ankle straps, unbelievably feminine.

—I thought you said we were wearing sneakers —I said.

—With those legs it would be a sin.

I put them on and started to walk. I felt my ass lifting, felt myself looking less like a teenage boy and more like one of those girls from the club Tobías wanted so badly to meet. With every step, the thong slid between my cheeks, rubbing my shaved little ass, and the dress caressed my silicone tits. My cock, flattened under the corset, throbbed again without being able to fully grow, trapped, sore, deliciously uncomfortable.

—Better sneakers —I insisted—. How am I going to explain to Tobías that I know how to walk in heels?

Selene thought for a second.

—Don’t worry. I’ll tell him I taught you in an hour and that, because they have a platform, you can barely feel the heel. That’s why it comes so naturally to you.

***

When she finished dressing me, she left me alone in the room. All that was left was to wait for Tobías to come get me. I lay on the bed, looking at my legs wrapped in those sheer stockings, the high heels, the pink skirt riding just a little up my thighs. I brought one hand to my silicone breast and felt, for the first time, that fear was mixing with something much warmer. With the other hand I slipped beneath the dress, over the thong and the corset, until I found the soft, throbbing bulge of my trapped cock. I squeezed it gently through the tight nylon, and for a second I imagined Tobías, tall and broad, walking into that room, looking at me the way you look at a woman, pressing me against the wall, sliding his hand under my skirt without knowing it was me, his best friend. A tiny feminine moan escaped me, one I didn’t recognize as my own. There was no turning back now.