Not many people knew about my crossdressing. My mind would fill with worries about what everyone would think. I did tell two of my friends, David and Nick. They were experimenting with bisexuality and very open minded. Somehow I knew they would be more understanding, and they were.
The three of us lived in a small house for the price of an apartment. It seemed to be a much better choice. In apartments, everyone can hear every little word you say and everything you do. We were all discovering new sexual things and we didn’t want the whole world to hear us.
Though they knew, I found myself dressing up when they weren’t home. I guess I wasn’t comfortable yet. I’d been dressing for a little over two years and everyone who had seen my pictures online thought they were very passable. A few people thought I was a girl until I broke it to them.
Other than rent, a lot of my money went to building up my clothing collection. When we moved in, all I really had was some things I had swiped from my mom or aunt. We had the internet at my mother’s house too but it felt strange having women’s clothes shipped there. More than anything, I became concerned someone would open it and find out my secret.
My love for latex and leather was very obvious and Dave and Nick noticed right away. Almost all of the clothing that came to the house for me was made of one of the two. They both had a love for it too and would joke around about how sexy I’d look in them.
Whenever they were at work or just out, I’d dress up in my uniforms or corsets and get online. When I dressed, I became a different person. Sometimes I could barely tell it was me. Watching myself actually turned me on because I didn’t look anything like me, I looked like a very sexy female in a maid’s outfit or in a rubber catsuit.
I’d go into the fetish chat rooms and feed the people what they craved on my web cam. Whether that be smoking cigarettes (which works out for me as well because I have a huge smoking fetish), putting dildos into my ass, or jerking off. The thoughts of all these people watching and masturbating to me filled my head. I was a performer and I’d do anything to turn these people on. No charge, just pure satisfaction.
One night when David and Nick had gone out to the movies, I figured I’d try on my new latex school girl uniform. I’d be the naughty smoking school girl. To add to my costume, I learned to do pigtails correctly. My lips were glossy pink and just staring into the mirror had my cock hard, pressing against the rubber panties. I had put on a coat of latex shiner before hand so the light had the outfit glistening. I was very happy with the purchase. It was all black with a pink tie. My vinyl knee high’s complimented the outfit perfectly.
Just as I was lighting up my Marlboro cigarette, the door opened. It startled me, but it was just Dave and Nick. My first thought was “Oh shit, they are going to see me dressed as a girl. What if they don’t like it?”
“Wow, look at her. I would definitely have sex with that sexy girl. Wouldn’t you Nick?”
“Oh god yes! Love the outfit by the way. Must be new.”
I smiled, happy that they liked my appearance. “It is new, but I thought you two were going to see a movie?”
David sighed, “Well we were but the damn thing was sold out. I guess we should have left earlier.”
For the first time I started imagining what it’d be like to have sex with them. Their eyes were scanning my latex clad body, and I could see how much they were enjoying it. I’ve never done anything with a guy before but the thought of being dressed like a woman and servicing a guy always turned me on. My only thought was, “Here is your chance to service not one, but two guys.”
Nick walked around me, examining the outfit, “Man, that is really tight. It shows off your ass nicely. I guess I had never noticed how nice it was.”
“Thank you.” I took a drag off my cigarette. “Well it’s like a second skin, it’s so tight so it shows off all aspects of your body.”
Everyone was silent for a minute, it was uncomfortable. There was a looming sexual tension. Without even thinking, I blurted out, “Do you guys want to fuck?”
For a moment I was thinking, “Oh fuck oh fuck, what have you done?! You have made things awkward and you have to live with these people!”
It turns out that they were just a bit surprised by this but they both responded with the same answer, “Yes!”
“Really? Okay. Well take off your clothes so this naughty school girl can service you.”
They fumbled with buttons and finally got the clothing off, tossing it onto the couch. They were both half way there so I got down on my knees and started licking their shafts. Like I had said, when I dress, I become someone else. The questions thoughts stopped and all that was on my mind was pleasing them. I took Nick into my mouth while holding the bottom of David’s shaft. His cock grew inside of my mouth, poking at the side. It was so thick and hard as it slid to the back of my throat. He withdrew his member from my mouth, then tapped it on my tongue. Dave grabbed my hair and pulled me closer to his dick so I sucked at the head like a lollipop.
“Who wants my cock inside them?” My eyes stared deeply into theirs, seductively, waiting for an answer.
“David will take it, he owes me some oral.”
“Okay, well don’t cum in his mouth.”
“Why not?”
“Because I’m here to please both of you and I want all the cum in my mouth.”
“This girl is quite a slut,” Nick teased.
He sat down on the couch as Dave bent over, leaning his mouth closer to Nick’s throbbing prick. Right away he started sucking him down to his balls.
I’d never fucked a man in the ass but this wasn’t me. I was this slutty crossdresser who would fuck or suck anyone.
I spit on my hand and rubbed it along his hole and plunged my cock inside of him. It only took a few thrusts before he had loosened up and I could fuck him the way I wanted. His moans were escaping from his mouth, which was full of Nick, as I progressively fucked him harder.
“You love that cock in your ass. You love getting fucked by a slutty school girl with a hard prick, don’t you?”
“Mm, fuck yes. Keep tearing up my ass hole.”
I’d grip onto his hips and go full force as I listened to the slurping sounds that were going on a few feet from me. I couldn’t help but watch him take all of Nick into his mouth. He knew what he was doing and loving every second.
My balls were slapping against his ass as I’d push every inch into his anus. I reached around and started jerking his cock, which made him suck faster. The sounds combined with the tight ass hole that gripped my dick were nearly driving me over the edge.
Since this was my first time fucking a guy and being dressed up while having sex, it was all a bit much. I don’t think I’d ever been that turned on in my life, up to that point. I’d only had anal sex once before and I don’t remember her being this tight. The friction was filling me with so much pleasure. It was almost like tight latex being wrapped around your rod.
“Oh shit. I’m getting real close. Fuck, Dave, you have to stop sucking or I will orgasm.”
“No! Don’t cum! I want it all!”
I pulled my cock out of his ass hole and got back onto my knees. They both stood up and walked towards me when I signaled for them. Their cocks were both large and rock hard, begging to release their seed. I spit on them and started stroking quickly, staring up at them, licking my pink glossy lips.
“Come on. Give me all that you have. I want my mouth full! Fucking cum on my tongue. I want it all.”
I started to suck on David’s head but I realized that Nick was nearly there so I switched. I continued to stroke David, but I focused on taking this huge cock down my throat, bobbing my head on it. I’d suck hard at the head before diving all the way down to his balls. Without meaning to, I was moaning as I sucked hungrily. For the first time, I took a man’s cum into my mouth. He didn’t give me warning. His moaning picked up but I thought nothing of it until a warm salty fluid started to shoot all over my tongue. I stroked the length to release every last drop.
A thought came to my mind and it was so incredibly hot to me. I couldn’t resist so without swallowing I put David into my mouth. The cum swirled around his cock as I kept my lips tightly sealed around him, so as not to let any get away. Nick’s cum was covering his friends shaft and it was turning me on so much. I felt like such a whore, which is what I wanted. My hand reached down and started furiously stroking my own dick. Within seconds, more sperm was filling up my mouth. I had to pull part of him out so I could focus on swallowing. I already had Nick’s seed in my mouth and now that Dave’s was mixing, there was too much. His cock kept spurting and I swallowed the best I could, but some did leak out and drip down my lips.
The thought of all that hot semen spurting down my throat was all I needed to get off. I started moaning very loudly, sucking harder on David’s soft sensitive head.
We all lay down on the floor. The pleasure was still circulating through me. It was unlike anything I’d experienced and I knew that this had to happen again. The satisfied looks on their faces said that it was nearly a guarantee.
