My Former Classmate Recognized Me in Drag That Night

I had barely started exploring cross-dressing, encouraged in large part by my boss, for whom I had been dressing as a woman for months. Even so, we rarely went out together dressed up to public places. That night we decided to have a few drinks at a modest bar in Colonia Juárez, one of those places older people frequent and where no one ever looks up from their table.

When we left, while I was waiting for him to bring the car around, what I least expected happened. Rubén, accompanied by his wife, recognized my face almost immediately. I saw his eyes widen and a half-smile form on his lips before he swallowed it in conversation with his woman.

For a second our gazes met fully. He looked down right away, pretending to search for something in his wife’s handbag, but I still caught the flush rising up his neck. The sidewalk smelled of damp and extinguished cigarettes, and the night cold made me cross my arms over my coat. Then the car arrived and I got in without looking at him again.

I kept wondering whether he had really recognized me or if he had simply liked the girl he saw. The answer to that doubt came the next morning, with a private message and a friend request.

Rubén had recognized me the night before and had looked me up on social media. Since we still had acquaintances in common, I suppose it was no trouble at all for him to find me. Along with the request came the message: “Hi, I don’t know if you remember me. I’m Rubén, from high school.”

I replied politely and accepted his request. We caught up, asked about work, about family, that formal talk you have with someone you haven’t seen in years. Until he dared to write what he really wanted to know.

—Can I ask you something?

—Sure, what’s up?

—I hope you don’t take this the wrong way. Are you a cross-dresser? Last night, I swear, I saw a cross-dresser who looked a hell of a lot like you.

So he had recognized me after all. I felt my nerves surge up through my chest. I didn’t know what he was going to think of me now that he knew.

—Haha, where did you see her? —I answered, testing him.

—In Juárez, coming out of a bar.

—Yeah, that was me.

—Well, let me tell you, you looked gorgeous. I thought you were a real woman. If I’d been alone, I would’ve even hit on you.

—Haha, oh yeah? And what would you have said to me?

—I don’t know, something really filthy.

We kept chatting by message about a thousand different things until the time came to close out the day and disconnect. As we said goodbye, he wrote: “Hey, send me your cell number, okay? Let’s see if we can meet up this week, have a drink and talk more comfortably.”

To feel out his intentions, I replied jokingly.

—What do you want my number for? I remember that in high school you used to say you didn’t like fags.

His answer left me frozen.

—Not in public. In private it’s different.

—Now I don’t get you. So do you want to see me in public or in private?

—In private. How about today? There’s a hotel near my work. Tell me where to pick you up.

—Really? But I don’t think you want to see me today, I didn’t bring girl clothes.

—What a shame. Then you tell me what day I can see you dressed up and I’ll pick you up that day.

We said goodbye. My inner girl was insanely turned on by the idea, but part of me still distrusted him. I wanted to be sure it wasn’t a joke, a whim, or some game of his. Because that was how I remembered him from high school: Rubén always playing the macho guy in class, bragging about women. And having seen him with his wife that night made me doubt his interest in me even more.

But as if he could read my mind, Rubén never let up all week. He kept asking me to meet up, asking me for photos, asking me about my experiences. I answered briefly, and the most I told him was about my relationship with my boss, without going into details.

—If I’d gone out alone the night I saw you, I would’ve proposed we fuck, without even knowing it was you.

—And if you recognized me afterward?

—I would’ve taken you anyway. Even more eagerly, because there would’ve been more trust.

—But that night I was going to fuck my boss.

—Either way I would’ve tried to convince you to make a fool of him once. I don’t think he’d mind you cheating a little. Especially at his age.

In the end I agreed. He picked me up as we’d arranged. In my bag I had a navy blue pleated skirt, perfect for the occasion of meeting up again with an old classmate, nude stockings, black thong and bra, a white sleeveless blouse, and black zip-up knee-high boots. Some makeup, which I had already learned to handle reasonably well thanks to my boss, and a wig of long, straight black hair.

In the car we chatted about those school days, like two buddies reuniting after so many years. The conversation was very pleasant, although in hindsight it clashed terribly with the real intention of the date.

Feeling him as the male friend from high school filled me with nerves when we finally got to the room. I shook off the trembling as best I could and, like a shy teenager, rushed into the bathroom without saying a word.

There I took my time getting dressed. I looked at myself again and again in the mirror and always found something to fix. Or, rather, no effort was enough to make me look less like a guy in a disguise. The fourth time Rubén knocked on the door to show me his impatience, I decided to come out exactly as I was, however I looked.

—You look very pretty —he told me, while he took me by the waist and led me to the edge of the bed, where we sat down.

The room smelled of cheap disinfectant and the only light came from a lamp beside the bed. I felt the mattress dip under both of us when he settled in beside me, and the closeness of his body gave me goosebumps. It was strange having him so near after so many years, remembering him as the noisy kid in the back of the classroom.

He offered me a beer he had ordered while he waited. It seemed like a good idea to drink it and ease my nerves. He must have noticed I was embarrassed, because he went back to talking about the past, just like in the car. While we remembered our high school years, he rubbed my knees in a slow, almost soothing gesture. Then he started.

—Did you already like being a girl back in high school?

—I was already drawn to that scene, but I still wasn’t dressing yet.

—Did you have any encounters with anyone back then? A boyfriend, something like that?

—Do you remember the English teacher?

—With him?!

We both laughed. Then he went on.

—And when we were “brushing up against each other,” when we’d press ourselves together under the desk, did you like it?

—Yes… Honestly, I enjoyed it a lot.

—And was there anyone you liked more? Mario’s? Beto’s?

—You won’t believe me, but the one I liked best was yours.

Rubén got up from the edge of the bed and began taking off his belt.

—I already knew it. Back then I could tell how you’d grind your ass against me when I rubbed up on you.

—And you knew damn well how to press it against me. Yours was the one I liked best because it got hard right away. Back then I dreamed that someday you’d want to fuck me.

As I said it, with no shame left, I pulled down his pants and boxers. I took his cock in my hand and started stroking him slowly while I kissed his balls. The kisses turned into licks, and from the balls my tongue moved up the shaft to the head.

—Fuck, little slut, I really needed this. My wife doesn’t like sucking it.

—Well, I love it. Your wife is so fucking stupid, having such a delicious cock to suck and not doing it. But don’t worry: whenever you want a blowjob, just tell me.

After sucking him for a good while, Rubén wanted to lie back, with his cock fully hard, while I sat on top of him to take him inside me little by little.

—That bastard boss of yours has really got you trained. It went in the first time.

—Yeah, he’s opened me up real good.

—But you still squeeze so fucking nice, baby.

—Do I squeeze more than your wife?

—A lot more. And you move nicer than she does.

—Who fucks better, daddy: your old lady or your slut, which is me?

—You. That’s why I looked for you, to have you as my slut, to use you whenever I want to fuck good and hard.

—Use me, Rubén. Use my ass; it was always yours. Don’t ask me for it, just take it, like when you used to rub up against me at school like that, by surprise.

I got off him only to settle on all fours at the edge of the bed. Standing up, he brought his cock to my ass and opened me again, effortlessly. He drove hard while he spoke in my ear.

—That’s it, slut… Fucking easy-assed fag. Let’s see what you tell your boss now that another man has already made you his.

I took every furious thrust with moans and answered him breathlessly.

—Like that, baby, like that, little Rubén, make me your slut… Do you fuck that good when you’re with your wife?

—No, she doesn’t turn me on like you do. And besides, you’ve had my cock hard since high school.

Rubén came inside me. He pulled out still hard, took off the condom, and let himself fall onto the bed. I lay down beside him, turning my back to him, my breathing ragged and my body spent.

Then a doubt came to me. I turned to look at him over my shoulder and asked:

—Aren’t you going to kiss me?

—No, that seems too faggy to me —he replied.

And as he said it, he slid his hand over to my ass and stuck his middle finger into my freshly fucked hole, a gesture that tore from me a long moan I couldn’t hold back.