Confessions of a Sissy XDresser

Confessions of a Sissy Crossdresser

Prologue: When I was young, I'd place ads in Craigslist looking for men who liked sissy crossdressers. I lived out my wildest fantasies a hundred times over. This is the story of some of those nights.

Eros Adult Video was a few miles from downtown in a warehouse district. A freight line, overrun by weeds, lies nearby. Train noises came from somewhere in the far distance. Men got out of cars and trucks, shuffled across the parking lot, their shoes scuffing the pavement as they went. I was in my car, parked in the back, sitting on a butt plug. Well, squirming more than sitting.

I was out of school, in a new city, and ready to explore my sexuality. I decided to go inside. As I stood next to my car, making sure I had everything, an El Camino pulled into the parking lot and drove by me slowly. I'm thin with long legs and a bubble butt. I had on heels, thigh highs, panties, a long sleeve burgundy blouse and a curly, red wig. Bracelets swung from my wrists. I made my way towards the front door slowly, soaking up the attention.

When I entered, I saw a Hispanic guy in paint splotched work clothes. He was rugged, about my age, and looked away when our eyes met. I came down an aisle and saw a powerlifter type guy, near the stairs to the basement, watching me intently. I walked past the front desk towards the stairs to the basement. Two men followed me to the stairs. I twirled my purse around my legs. The Powerlifter Guy was browsing the XXX rated movies on the shelves.

The Powerlifter Guy walked by, brushing my butt with his midsection. I smiled at him. A noise startled me. A couple came up the basement steps hanging onto each other and laughing. She had on a halter top with thin straps and her boobs flopped around. He paraded her around the room and, for a moment, no one paid any attention to me. They stumbled out the door into the parking lot.

I walked towards the Hispanic guy, gazing into his smoldering dark eyes, as I came by. He watched me as I walked out the door and headed back to my car. The El Camino was parked next to my car. A guy reclined in the front seat with his cock out. It was erect, throbbing, and slick with precum. He looked like an MMA fighter. Dark hair swirled around his head, and he hadn't shaved in days.

The next thing I remember, we were careening around corners speeding back to his place. He pulled into an apartment complex. "Ready to be my little fuck toy?" he asked with his hand on my knee. His roommates were home, so he went inside alone. Minutes later he appeared at the front door and waved. My heels clicked and clacked on the asphalt as I ran from his car towards the building. He grabbed my hand and pulled me up a flight of stairs.

He dropped his pants and his cock flopped out. I got on my knees and did what sissies do until he was about to climax. He nudged me towards the bed. I got on my hands and knees. He lubed up and worked the tip inside of me, going slow, because it wouldn't go in.

When I loosened up, he went balls deep, pounding me so hard I grabbed the mattress. I came in two minutes. Pleasure turned to pain. When he was ready to explode, he would pull out, taking his time, enhancing his fun, prolonging my agony. He slammed his cock inside me. Sex sounds filled the room, THWAP, THWAP, THWAP. A blond with big tits was getting fucked doggy style on the TV in front of my face.

"Tight pussy, tight pussy," he mumbled to himself. I'm a cum dump for alpha males. The skinny geek the jocks taunted in high school. Mascara tears streamed down my cheeks. He finished with a series of back wrenching thrusts. I drove home, in a daze, thinking the streetlights looked weird. I hated myself. No one will ever love me. I promised God it would never happen again.

Years later, in a new city, I discovered Craigslist M4M. I lived out my fantasies one hundred times over. One night, a rude guy replied to one of my ads. I played along, slightly interested. But, as soon as I saw his pictures, which gave me wet dreams, I decided he was worth meeting. I shared my foolish and stupid fantasies with him, things I'd never actually do, like being the sissy cook on a ship with a hundred pirates or walking the streets for rent money.

We decided to meet at a seedy hotel. I had on my sluttiest outfit, better heels, a new wig, thigh highs without runs in them, a snug fitting animal print blouse, silicone C cup breast inserts. It was a frigid night. He never showed up. I drove away, in tears, to horny to go home, and ended up near a cluster of gay clubs. I parked across the street in an empty lot between two buildings. Thoughts of suicide overwhelmed me. I was completely broken.

A white pickup truck pulled in and parked. I got out of my car and sauntered towards the street. My breast inserts jiggled with each step I took. He called me over. He was black with a weathered face and large nose. He took me into his arms. "Mmmm yeeeessss," he murmured. There was a massive bulge in his pants. He put both his hands on my butt and squeezed. A guy with a flashlight and orange safety vest walked into the parking lot.

The Black Guy closed the door and drove off. The Guy with the Flashlight walked by me, up the length of the parking lot, turned around and came by me again. I looked at each entrance, knowing the Black Guy would come back. He never came back. I went back to my car and sat there shivering. I put the key in the ignition. Just then, a car twenty yards away, flashed its lights. I walked over there.

A black guy sat in a sedan with the window open. He was in his mid-twenties and lean but richly muscled. He had on a wife beater T-shirt. There was a shag rug all over the dashboard and steering wheel. He talked on his cell phone as I walked up. A few minutes went by. Finally, he hung up and looked at me. I waited, with my arms folded, for him to say something.

"You like to suck cock?"

"Yeah."

"Follow me," he ordered.

I followed him to a parking lot.

He parked behind a fence with vines all over it. People parked behind us, getting out of their cars, slamming doors, on their way to a leather bar across the street. He pulled his seat back as far as it could go. He pulled his jeans down. His cock was semi-erect, about six inches long, and had a nice chubbiness to it.

A bristly trail of hair ran from his cock to his abdomen. His abdomen was grooved with solid muscle. I sucked his cock like a worthless whore. I swallowed it without gagging. His precum tasted sweet and milky. "Wanna get fucked?" he asked. I nodded. I put lube all over his cock and wiped my hands on my blouse. I crawled on top of him and guided the head of his cock to where it needed to be.

It wouldn't go in. My right knee was crushed up against the car door. I tried again and, little by little, got it all inside. My whole body reacted. I rose up, then eased down on it again, skin on skin, all the way to the base. It filled me with toe curling pleasure. I bounced up and down on it. His hands moved up and down the sides of my body. Just outside his car, people were walking around us.

The windows fogged up. His cock fit perfectly, pushing me past my limits. I was breathless but didn't want it to stop. Out on the street, through the back window, I saw cars going back and forth. We came at the same time. The rhythm of our bodies stopped. His skin glistened with sweat. I grinded on him very slowly. My back was arched, my body relaxed, moved up and down a few inches at a time.

"Is this what you've been waiting for?" he asked. He was still rock hard and I was enjoying the feeling of having him inside of me. Our lips brushed together. We kissed. He pumped me slowly at first. Then harder and harder. He rocked my world. I completely surrendered to his will. He was drained and exhausted and so was I. When he was done, I crawled back into the other seat; and felt around for my panties.

I couldn't believe what had happened. It shocked me how attractive he was. My head was spinning but not really. I was proud of myself. I put my panties on and walked back to my car. It was bitterly cold, an icy wind gusted, but I didn't feel it. As I was walking, I thought about the big grass field that me and all my friends would play on as kids and how happy we all were.