I Dressed as a Woman and Went Out Looking for a Stranger

I want to share what happened to me on an ordinary Sunday, the day I finally dared to do something I’d been imagining in the darkness of my room for months.

My parents had gone to the coast for the weekend. I had the whole house to myself, no schedules, no eyes on me, no one to ask me anything. That freedom filled me with an excitement I hadn’t felt in a long time.

I got up early, took a slow shower, and pulled out from the back of the closet everything I kept hidden away. I did my makeup slowly, enjoying every step. I have long eyelashes, so I didn’t need false ones; I put on mascara, a deep red lipstick, and a little blush. Then came the clothes: a black thong, a garter belt with fishnet stockings, silicone padding inside the bra, and over that, a strappy blouse and a tight, pale miniskirt. I slipped on high heels, stuck on some fake nails, and at the end, I put on the wig, long and brown.

I looked at myself in the mirror and barely recognized myself. I liked what I saw. I felt sexy, shameless, like the woman who only existed when no one was around. I called myself Vanesa, as I always did in my head when I transformed.

I wandered around the house for a while pretending to tidy up, but the truth was I only wanted to feel the stockings brushing my thighs and the sound of the heels against the floor. The excitement kept growing and growing. One idea started circling in my head: what if I went out into the street like this, dressed up, exposed?

My heart was pounding just thinking about it. I peeked out the window to make sure there were no neighbors on the sidewalk and, almost running, I climbed into my parents’ car. I started it with trembling hands.

Driving through the neighborhood dressed as a woman was one of the most intense sensations of my life. Every traffic light, every pedestrian who crossed without looking at me twice, fed my arousal. I felt like a slut parading among people who suspected nothing. I was so horny I needed more. I needed something real to happen.

***

A few streets before getting back home there were some buildings under construction. I passed by there almost every day and always found myself watching the workers, fantasizing that one of them would take me into a corner and use me. They didn’t work on Sundays, I knew that. So I thought it was the perfect place to stroll around alone with my fantasy.

I drove the car through a side entrance to the site and left it behind a half-built wall. I checked that no one could be seen. I got out and started walking among the rubble, the bags of cement, and the iron bars. The echo of my heels bounced off the bare walls and that made me even more aroused. I walked slowly, swaying for no one, enjoying being Vanesa in the middle of that raw, harsh place.

Then I heard voices. I didn’t know where they were coming from. I got scared all at once; I had wandered too far from the car. The only thing I could think of was to duck into what looked like a little workroom, dark and without a door, and crouch against the wall so they wouldn’t see me.

My heart was racing. They were the guards for the site; when they heard the heels, they’d come out to see who was walking around there. I stayed silent, barely breathing, until I stopped hearing anything. I thought they had left.

I decided to come out and get the hell out of there as fast as I could. But when I peeked out, I ran straight into one of them, standing right in front of me. I froze, unable to move a muscle. He was a tall man, around forty-something, dark-skinned, lean but wiry, wearing a work-worn T-shirt, stained jeans, and heavy boots.

“Well, well. What do we have here?” he said, looking me up and down.

I instinctively pulled my miniskirt down and forced my voice as feminine as I could.

“Please, don’t say anything. I just came in to walk around a little, I was leaving already.”

“I’m going to have to report this,” he replied, very serious.

A chill ran down my spine. I imagined the scandal, more people showing up, the police.

“No, please, don’t tell anyone. I’m leaving, I swear.”

He took a step toward me and I backed up.

“And what are you going to give me in exchange for keeping quiet? Because I should call my partner and the police.”

“Not the police, please,” I begged. “I’ll do whatever you want.”

He kept coming closer, slowly, and I kept backing up until my back hit the wall and I had nowhere else to go. The situation terrified me and, at the same time, it had me completely turned on.

He stopped just a few centimeters from my face. And then, with the arousal I’d been carrying from home, I couldn’t stop the bulge under my skirt from showing. He noticed it instantly and a crooked smile crossed his face.

“So you’re a little faggot,” he muttered. “You know what I do to queers like you?”

“No, sir,” I answered, in a tiny voice.

“You’re going to learn right now, little slut.”

“But they’ll see us,” I weakly protested.

“My partner went to the other section. It’ll be a good while before he’s back.”

***

He grabbed me by the waist and pulled me toward him. When I felt his rough hands on my skin, my whole body bristled and a sigh escaped me. He smelled of earth, cement, and work-sweat; it wasn’t an unpleasant smell, on the contrary, it stirred something in me.

“You like cock, don’t you?” he said right near my mouth.

He kissed me. It was a rough kiss that made me tremble from head to toe. I was paralyzed, only feeling his hands holding my waist. Without even realizing how, my hand was already resting on the bulge in his pants. I started stroking it through the fabric and felt it harden little by little. It was insane. My dream was coming true: I was about to taste the cock of a complete stranger.

I went down, almost by instinct, until I was on my knees in front of his fly. I unbuttoned his pants with clumsy fingers and started kissing his stomach, right below his navel. His breathing quickened. I pulled his pants down to his knees and left only the boxer shorts in front of me, which I slowly removed while sticking my tongue out to welcome what he had hidden inside.

A big, erect cock sprang out in front of me, already wet at the tip. It was the biggest I had ever seen. Not too thick, but long, with visible veins and hot to the touch. Until that day I had only had two in my mouth, and neither had satisfied me; neither of them had even come.

I stood there, hypnotized. I took it in my left hand while with my right I stroked his testicles; the skin was soft, the opposite of his hands. I jerked him for a few seconds, looking up at him from below.

He grabbed the back of my neck and gently pushed me toward his sex. I stuck out my tongue and ran it over the tip, in slow circles. I kissed the head as best I could. I had fantasized about this moment so many nights that I knew exactly what I wanted to do. I took it into my mouth, first only halfway, pulled it out, and went down to lick his balls, running my tongue over them, biting them carefully, before taking him a little deeper again. He was moaning.

“That’s it, slut. You do it very well.”

“Do you like it, daddy?” I asked, lifting my gaze.

“I love it. Take all of it.”

He held my head more tightly and pushed all the way in. He reached my throat and I felt like I was choking, but I didn’t pull away; on the contrary, I wanted him even deeper. The rough hair of his pubic mound tickled my nose while I kept massaging his balls.

“That’s it, little slut, suck it,” he panted.

I pulled back to run my lips over the tip and trace the frenulum with my tongue, drawing circles. At times he knocked my face with it, dragging it over my cheeks, my lips, my chin. I swallowed him again faster and faster, sucked his testicles, jerked him with my hand. His moans became shorter and more frequent.

“Do you want milk, little slut?”

“Yes, give me your milk, I want it in my mouth.”

“Keep going, whore, your reward is almost here.”

I took him all the way in when I felt he was about to come. I sucked him slowly, as deep as I could, and felt the first stream of semen hit the back of my throat. He gasped hard. I swallowed. It was thick, but delicious. I pulled back a little so nothing would spill and kept sucking while more spurts came, more than I expected. The taste was intense, a little salty, and it drove me crazy. I couldn’t fit it all, so I pulled away and the last bursts landed on my face. I swallowed what I could. I took him back into my mouth to clean him properly.

He gathered up with a finger the semen running down my cheek and brought it to my lips.

“Don’t waste anything, whore,” he said.

“You make it taste so good, baby,” I murmured.

“Did you like it, daddy?”

“Of course I did,” he replied, pulling his pants back up. “Now get the hell out of here, my partner’s about to arrive.”

***

I took off my heels so I wouldn’t make noise and ran out, with my face still stained and some semen sliding down my chin. I didn’t care. I was trembling, yes, but I was also floating: I had just fulfilled the fantasy I’d fed for so many nights in the dark. Giving head to a worker, to a stranger, in the middle of an empty construction site.

I drove home with my heart still racing. By the time I got in, it was already getting dark. I showered slowly, replaying every second of what had happened, and ended up masturbating in bed, remembering everything. As I came, I could only think about one thing: when I would go out again, dressed as Vanesa, to look for my next adventure.