My First Night Dressed as a Woman with a Stranger

I grew up in a completely ordinary family: my father, my mother, and two sisters. I was the middle child, the only boy. My dad wasn’t absent, but work kept him traveling almost all week, so if I was lucky I saw him a couple of times when he came back to Punta Serena. The house, most of the time, was women’s territory, and I suppose some of that stuck to me from a very young age.

The first time curiosity got the better of me, I hadn’t even turned twelve. My sister Carolina, four years older, had left a black panty with a little bow on top of the dirty laundry in the bathroom. I was about to get in the shower, but when I saw it there, abandoned, I couldn’t help myself and tried it on. A current ran through my whole body. The fabric was soft, infinitely softer than that rough men’s underwear they made me wear.

From then on, every time I showered I checked whether she’d left any garment in the hamper. In time I worked up the nerve to open her drawer, always hoping to be alone at home, which luckily happened often. At first that was all it was: take a panty, put it on, look at myself in the mirror for a second, take it off, and put it back exactly where it had been so no one would suspect anything.

The years passed and the curiosity grew with me. I started rummaging deeper in her wardrobe and found clothes she no longer wore: skirts, jeans, blouses, and the occasional bra. I waited eagerly for the moment I’d be alone so I could put it all on. In front of the mirror I felt like I was somewhere else, as if I were finally occupying the right body.

By the time I turned eighteen, I knew for sure it wasn’t a phase. I’d had one girlfriend or another, nothing that went beyond kisses and clumsy groping, but what really made my pulse race was still locking the door and dressing up. What I still didn’t know was how much I wanted someone else to see me like that.

One night, coming back from downtown, I discovered that part of it. It wasn’t even nine yet, but the street was nearly empty. A man in his thirties came up to me and, in a low, shameless voice, told me I had a good body, that from behind I looked like a woman, that he’d love to stick it in me from behind until I screamed. I got scared and quickened my pace toward the bus stop where there were more people. But all the way home I couldn’t stop thinking about his words. He’d said them in such a filthy, perverse way that it stirred something deep inside me and I felt my cock hardening in my pants, unable to help it.

That night I waited until everyone was asleep and silently went down to the dirty laundry. I found a blue panty and one of Carolina’s nightgowns and took them to my room. I stood in front of the mirror, turning to see myself from behind. The guy had been right: from the back I could pass for a woman. I ran my hands over my ass, squeezing it, imagining they were a stranger’s hands. The thin fabric slipped between my cheeks, and with every movement my cock showed more and more against the cotton. That night I masturbated differently than men do, rubbing myself slowly with two fingers over the panty, as if instead of a cock I had a swollen clit that needed to be worked in slow circles. I bit my lip so I wouldn’t moan too loud, sped up my wrist until I started trembling, and came inside my sister’s panty, feeling the warm semen cling to my skin through the fabric. I’d never finished so intensely, never felt those long spasms that left me breathless.

***

For months my routine was the same: school, home, and the anxious wait to be alone so I could run to my sister’s room. Sundays were sacred. The family visited my grandparents, but Carolina had managed to get out of it, and not long after I did the same, using the excuse that I was staying home to play video games. The condition was that I clean the house. In return I had hours all to myself.

Carolina would leave around two and come back around nine. My parents arrived after ten. As soon as the door closed, I got dressed and moved through the house trying to behave like a lady, doing everything as femininely as I could. For me, Sundays were not a day of rest. They were the only day I could be who I truly was.

In time, my parents gave me more freedom. They started letting me go to parties and come back late, at one in the morning. And one of those nights I didn’t go where I’d said I was going. I went to the red-light district of the city. Today that avenue is lit up and full of bars, but back then it was dark, unsafe, dominated by prostitution.

I wasn’t going to offer myself. I just wanted to see up close that world people talked about so much. I saw women with their pimps, a couple of gorgeous transvestites, and the occasional lone guy. The routine was always the same: someone standing on a corner, a car pulling over, a short conversation, and then the person either getting in or staying put. I was about to leave when a car pulled up and the driver, a guy in his mid-twenties, told me to get in. I said no, more out of embarrassment than fear, and kept walking.

I couldn’t sleep. That night I masturbated imagining what would have happened if I’d said yes: how I would have spread my legs in the back seat, how he would have pulled down my pants and shoved his cock into my mouth without asking, how he would have spit on me and fucked me right there with my face pressed to the window. I came in my hand thinking about it. All week I kept turning over the idea of going back and, this time, getting in. I kept telling myself it was crazy, that a stranger was a risk, and I convinced myself to stay away. But the desire wouldn’t go away.

On Saturday I was still telling myself it wasn’t a good idea. At six in the evening some friends invited me to a party; I said no to them, but to my parents I said yes, that I was going with them. They only asked me not to come back too late. Almost without thinking, I knew I’d go back to the red-light district. I took advantage of the fact that Carolina wasn’t home, went into her room, and took a black panty from her, insanely comfortable, with a soft perfume still clinging to it. I would wear that under my men’s clothes.

In those years, because of fashion, I almost always dressed in black and wore tight pants. It was hard to control my erection while dressing, because every brush of feminine fabric against my cock made it jump to full attention, but on the way to the avenue I managed to calm it down. I couldn’t believe it: I was walking downtown at night with women’s underwear pressed against my skin, the seam marking the crack of my ass with every step.

***

I arrived around nine thirty and sat for a good while, gathering courage to stand up and “offer myself,” though I still couldn’t quite work up the nerve. After a long while with nothing happening, I decided to walk the whole avenue to see what I could find. Past eleven, I’d covered about five blocks when a black pickup truck slowed to a stop beside me.

I kept walking. The man behind the wheel, who looked about forty-five, asked if I didn’t want to get in. Truth was, I found him attractive. I don’t know whether it was the tone he used or those gray hairs of a mature man that had always drawn me in, but something about him stopped me. I played hard to get and told him no. He insisted, now offering me a ride. I asked if he was sure, and when he said yes, I opened the door and got in.

—My name’s Rodrigo —he said as soon as I sat down—. You caught my eye and I wanted to meet you.

—Okay —I replied—. But I want to be honest: I’m eighteen.

—I’m forty-five —he answered—. Does that bother you?

—No, not at all.

—Then I don’t mind what you’ve got going on either.

While he drove, he told me he’d only recently moved to the city, that he had two children, and that he was separating from his wife. Then he casually let slip that he hadn’t fucked in a long time, that he barely even remembered the last time a mouth had touched him. Playing innocent, I told him I didn’t know what he meant.

Curiosity got the better of me and I asked him what he wanted to do. He looked at me out of the corner of his eye, licked his lips, and told me straight out, no beating around the bush: he wanted me to suck him off right there in the truck, to unzip him and pull out his cock and take it into my mouth all the way to the back. I told him I didn’t feel comfortable in the car, that maybe we should go to his place instead. He thought about it for a moment and agreed, on one condition: that I crouch down so none of the neighbors would see me. Before we arrived, he lowered the passenger seat back and I hid myself.

When we got into his house I felt an odd calm. It was a nice place, small, but with a large bedroom and a bathroom with a jacuzzi. Thinking about it now, it was the perfect house for a bachelor in his late forties.

I’ll never forget the moment he lay down on the bed and stripped off, ending up naked and barely covered by the sheets. I managed to catch sight of his cock before he covered it: thick, long, veins standing out, already half hard resting against his thigh. I hesitated. I didn’t know whether to take my clothes off or ask him to take me back. But when he turned off the light, I understood it was now or never. I took a deep breath and pulled off my T-shirt. Before lowering my pants and letting him see what I had underneath, I asked him.

—Is this a one-time thing, or are we going to meet again?

—If you want, we’ll meet again —he said—. It’s your decision.

—Well, then I’m going to tell you a secret.

—Tell me, I’m listening.

—I love wearing women’s clothes. Sometimes I go into my sister’s room, borrow her clothes, and put them on. I like pretending I’m a girl. I feel good that way.

—You’ve got a pretty body —he replied, looking me up and down—. Dressed up, you probably look even better. With an ass like that, any man would make you his.

—If you get me some clothes, I’d be happy to put them on for you. For now I can only show you this.

I lowered my pants slowly, very slowly, and stood beside the bed with Carolina’s black panty stuck to my body, pressing my hard cock against the fabric. I heard him let out a long sigh, as if the air had been knocked out of him. He ran his tongue over his lips.

—Turn around —he asked hoarsely—. I want to see your ass.

I obeyed. I turned slowly and stood still, showing him my cheeks barely covered by the black lace. I heard the sheets rustle when he sat on the edge of the bed.

—Come here —he whispered.

I moved closer. He put his hands on my hips, pulled me toward him, and buried his face between my cheeks over the panty. I felt his hot breath through the fabric, his nose pressing into the hollow of my ass, his mouth opening and closing over my cheeks. I shivered all over. He bit one cheek, then the other, and ran his tongue over the seam of the panty before inviting me under the sheets with him.

It was my first time with a man in a bed: him naked, me in women’s lingerie. He had a good body, a broad chest covered in gray hair, and I found him more and more attractive.

—This is the first time I’ve been like this with another man —I told him—. Can I kiss you?

He didn’t answer. He just kissed me on the lips, first softly, then driving his tongue all the way in, tangling it with mine, biting my lower lip. I immediately felt myself getting hard, harder than I ever had before, straining out over the edge of the panty, and I noticed the same was happening to him: his cock was pressing into my thigh, hot, throbbing. He took my hand and brought it there, forcing me to wrap my fingers around it. It was thick, heavy, hard to close my fist around. I started moving my hand up and down, clumsy at first, hearing him moan softly against my mouth.

He lowered his hand to my panty and squeezed my cock through the fabric, then pulled it out from the side and started jerking me off slowly, with a palm wet with saliva. He pinched my nipples, one after the other, until they hardened like stones. After a couple of minutes like that, I instinctively began moving downward, kissing his neck, his chest, his stomach, until I reached his member, which was fully erect, pointing at the ceiling, the tip already shining with pre-cum.

I knew what I had to do, but I didn’t know how. First I touched it with my hand. It was the first cock I’d ever touched that wasn’t my own, and Rodrigo’s was big and thick, with taut skin and a thick vein running beneath it. I wrapped my fist around it and felt it pulse against my palm.

—I don’t know how to do it —I admitted, looking at him—. It’s my first time.

—Don’t worry —he said, stroking my hair—. I’ll guide you. Let your mouth find the rhythm on its own. Stick out your tongue first, suck my balls, get it all wet before you take it in.

I started timidly, licking him from base to tip, following that thick vein with the tip of my tongue. Then I went down to his balls and took them into my mouth one by one, feeling them heavy against my palate. Rodrigo let out a growl and gripped my hair. I went back up the shaft, leaving a trail of saliva, and licked the tip in circles, tasting that thick drop already leaking from the head. I didn’t dislike it. It was salty, a little bitter, and it made me want more.

I took it into my mouth. At first just the tip, sucking it with my lips closed like it was a candy. Then a little more, as much as I could take, feeling it reach the back of my throat and trigger a gag. I pulled back, took a breath, and went down again, this time slower, learning how much I could swallow without choking. It was hard, but after a few minutes I got into the rhythm and started to really enjoy it. With my right hand I helped him at the base, squeezing and moving it in time with my mouth; with my left I slipped inside the panty and rubbed myself as if I had a clit, in fast circles over the tip of my own cock.

Rodrigo held my head with both hands, guiding me, setting the pace. He pushed gently so I’d take more of him, let me come up so I could catch my breath, then shoved me back down. He drooled on my chin, his saliva running down his cock and onto his balls, and I licked it back up with my tongue, slurping loudly, letting the sounds be heard. I could hear my own wet, obscene noises and it turned me on even more. My cock swelled inside the soaked panty.

—That’s it, baby, that’s it —he gasped—. Suck all of it, don’t let go, look at me while you suck me off.

I looked up without taking his cock out of my mouth. He was looking down at me with his mouth open, face red, chest rising and falling. Seeing me like that, in women’s lingerie, kneeling between his legs with his cock buried to the back of my throat, drove him to the edge. I felt everything in him tighten, his cock swell inside my mouth, the vein underneath beating faster.

I lost control. I felt a warm jet suddenly fill my mouth, then another, and another, thick, salty, sticking to my palate and tongue: Rodrigo had come without warning. I nearly choked. I swallowed some by reflex, while the rest slipped from the corners of my mouth and dripped down my chin to my chest. He kept gripping my head, forcing me to suck until the last drop, until his cock stopped twitching. He wasn’t lying when he said he’d been out of action for a long time. I went to the bathroom to clean my face and neck, and while I did, a new fear crept over me: maybe he was going to want to penetrate me. I’d never explored that far, it would probably hurt, and I didn’t know how to tell him no.

But when I came out I found him lying back, calm, and he asked me to get back into bed. I curled up against him, still wearing the panty and with my own hard cock resting against my stomach. The first man who had seen me in girls’ underwear, the one who had given me my first kiss and to whom I had given my first oral sex. He draped an arm over me and let his hand fall right onto my ass, squeezing me over the lace, playing with the edge of the panty.

—Another day I’ll show you the rest —he whispered in my ear—. When you’re ready, I’ll open you up slowly, with plenty of lube, until you ask me for it yourself.

My whole body broke out in goosebumps. I didn’t know what to say. I only pressed myself closer to him and let him keep groping me while I told him how it had all started, how I’d worked up the nerve to go out dressed under my clothes. He listened, and now and then he slipped a finger under the edge of the panty, barely brushing the hollow of my ass with his fingertip, making my whole body clench.

It was almost two in the morning and I had to get back. I asked him to take me home and he agreed. Before I got out of the truck he asked for my number, and I gave it to him with a smile so big it barely fit on my face.

At home I realized I hadn’t finished, and at first I didn’t care: I had felt so comfortable with him that the rest didn’t matter. I went up to my room, undressed, and stayed in Carolina’s panty alone, soaked in front by my own fluid and still with traces of Rodrigo’s semen stuck to the fabric over my chest. I threw myself on the bed on my back, spread my legs, and stroked myself over the lace, feeling my cock press against the fabric. I put two fingers in my mouth, got them nice and wet, and slid my hand back inside the panty, this time to touch the hollow of my ass. I’d never dared before. I took advantage of the lubrication and pressed slowly with my fingertip, feeling the muscle resist and then give just a little, letting me in to the first knuckle. I thought of Rodrigo, of what he’d whispered to me, of his thick cock opening me little by little, and with my other hand I started rubbing my cock over the panty, in circles, like a woman.

I masturbated slowly, moving my finger inside and my imaginary clit outside, replaying every second of that night: the smell of his skin, the taste of his seed on my tongue, the weight of his hand on my nape. I sped up. The bed started creaking softly and I had to bite my arm so I wouldn’t moan. When I came, it was in long spasms, one after another, pushing my ass against my own finger while semen smeared the inside of my panty. I finished with such an abundant release that I knew that garment was never going back.

I slept better than I had in a long time. And when I woke up, the only thing I could think about was that, at any moment, Rodrigo was going to call.