Last summer my dad lost his job for being drunk and driving the company van into a lake and even though I was going into grade twelve, the most important year of my entire life, we had to move and I had to start my last year of high school four hundred miles away from all my friends. Well, actually I didn’t really have very many friends, but it still sucked big time.

So the very first day of school, I was in the cafeteria and this girl walked right up to me and said, “you’re just like me.” She was wearing Dayton boots, ripped jeans and a leather jacket over top of a black t-shirt. Her short black hair was slicked straight back and she even had a cigarette behind her ear. She was without a doubt the most ‘butch’ looking girl I had ever seen. I couldn’t imagine anyone more unlike me. I was still trying to figure it out when she said, “you’re gay, right?”

Great. My first day at a new school, a chance to start fresh and already I was being labeled. What, is there a sign on my back? I set off gaydar everywhere I go, but it’s wrong. Guys hit on me all the time and girls only want to be my friend. I hadn’t actually had sex yet, but when I did it was going to be with a girl. And she’ll look like a girl, not like this bull dyke here. I was getting really pissed and wanted to tell her off, but all that came out of my mouth was, “umm no.”

“Really? Wow. Do you have any weed?”

I didn’t, but she met up with me after school anyway. We didn’t live very far apart and we walked to her house together. That’s how I met Lou. We were drinking colas in their kitchen when her older sister Dawn came home from her first day at beauty school. Dawn was the exact opposite of Lou. Even in jeans and a sweatshirt, she looked like a movie star. She had long brown hair, big blue eyes, perfect teeth, perky boobies…she was a walking talking wet dream. Lou saw the look on my face and groaned. “Don’t get any bright ideas big boy, she’s as gay as I am.” They both laughed and at the time, I didn’t know if they were kidding. They weren’t.

A few weeks after that first meeting, I was at their house when Dawn came home from school. She needed a model to practice make-up application on. She pleaded with Lou, but her sister was having nothing to do with it. Then they both looked at me. “Hey”, Dawn said. “You’ve got nice clear skin, you can be my model.” She said it just like that. As a statement, not even a question. They knew I couldn’t say no to either of them. That’s how it all got started.

For the next month, three times a week I sat still while Dawn worked on my face and Lou smoked cigarettes and looked for ‘fucked up shit’ on the Internet. When it came time to practice hairstyles, it was clear my thin wispy hair wouldn’t do so Dawn shaved Lou’s head and she went to the cancer clinic pretended she was sick and they gave her a wig.

With hair and make-up done, it wasn’t long until they had me trying on Dawn’s clothes and I was prancing around their house like a girl. It was during the Christmas holidays that I went out in public with Lou dressed as a girl for the first time. We went to a movie. I was so scared, but at the same time it was exciting. We started doing it on a regular basis. Sometimes Lou dressed up as a guy. She’d kept her head shaved and bought a moustache from a theatre supply store. We made quite a nice looking couple if I do say so myself.

I had a part time job and most of my money went to clothes and accessories. Surprisingly enough, Lou was an excellent seamstress. We’d find clothes that were close to the right size and she’d do her magic on the sewing machine and voila! It fit. We even bought a set a silicone inserts so I could have cleavage.

It was close to spring break and Dawn was practicing pedicures on me. I was flipping through the fashion magazines that she was always bringing home when I saw the most beautiful dress in Cosmo Girl Prom. I showed it to the girls and Dawn said, “Oh my god. That’s almost exactly like the dress I wore to my prom and I still have it.” About two seconds passed and we all got the same idea at the same time. I’d wear Dawn’s dress to the prom; we’d rent a tuxedo for Lou and we’d be a smokin’ hot couple.

This dress was amazing. It was a light peach colour that came off the shoulder, perfect for my little fake boobies. The crinoline and Lou’s sewing skills made it look like I actually had hips. I bought an open-bottom girdle and matching strapless long-line bra on EBay. New frilly full cut panties and stockings with lace at the top and flowers down the back seam. I even found some white satin pumps at a second hand store that fit me.

Lou’s vintage style tuxedo made her look like a gangster from the ’30’s. The band on her hat matched my dress and she even had a pimp cane and a peach coloured rose in her lapel. Fuck we looked hot.

It took people quite awhile to figure out who we were and even later we still got lots of compliments and lots of dances with boys and girls. Hell, we came in second in the voting for king and queen of the prom.

Unbeknownst to me, Lou had a flask of vodka strapped to the inside of her leg (I just thought she was happy to see me) and she started getting drunk. She had her eye on a little hottie named Tammy, but when that didn’t work out she turned her impaired attention on me. Yeah, I know I should have said ‘no’. I was sober, she was drinking, but I was flattered and pretty and horny and well, fuck, I was an eighteen year old virgin and I needed to get laid.

We went out to the far edge of the football field and started making out. She was kissing my neck and telling me how much she liked me and how hot my perfume was making her. When she started squeezing my boobies and admiring how firm they were, I realized she’d forgotten whom she was actually with. But did I make her stop? Nope. It wasn’t until my dress was up around my waist and my panties were around my ankles that she realized. “Oh yeah,” she said stupidly. “I forgot you had one of these.”

She started to lower herself down onto my cock and when I was about half way inside her, she let out a little gasp and I felt something running down onto my balls, but I didn’t realize what that might mean. Once I was all the way inside her, she rode up and down a couple of times then said, “Hey, put your legs on the outside of mine. I want to fuck like I’m really the boy and you’re the girl.” I spread my legs and hooked my ankles across her ass. She rode me like that, thrusting like she was doing the penetrating until I came. It didn’t take long. I think she was too drunk to come.

We got ourselves sort of put back together (I couldn’t find my panties) and headed back to the school. We caught a cab and Lou was passed out by the time we got back to her place. Dawn was there and together we got Lou into bed. It wasn’t until we got back into the living room that Dawn really noticed me. “What the hell did you get all over the back of my dress?” She demanded.

“Grass stains.” I said sheepishly.

She glared at me then walked behind me to get a better look. “What the fuck is this stain then?”

I had no idea what she was looking at. Finally she yelled, “It’s blood! You rat-faced bastard. You got my little sister drunk and fucked her out on the football field!”

My jaw was flapping, but no words were coming out. She kept yelling at me, but I couldn’t make sense of the words. She had never spoken to me like that before and I think I was in shock. She told me to stand right where I was and I didn’t move. When she came back into the room, she’d taken her pants off, she still had her shirt and panties on, but she was also wearing some kind of leather harness. Sticking out from the harness was a huge black cock.

“You think it’s cool deflowering innocent virgins? I’m going to show you how it feels.” And she pushed me down onto the couch. She got between my legs and lifted the dress up to my waist. “Look, you’ve even lost your panties. You’re going to lose more then that tonight.”

She put a bunch of lube on her cock and started pressing it against my asshole. “You better relax or it’s really going to hurt.”

“I’m scared.” I whimpered.

“You should be.” The head of the big black penis penetrated me and it hurt like crazy.

“Please.” I begged. “Don’t do this. It wasn’t my fault. It was Lou…” And I bit my tongue.

“Were you going to blame my poor little sister for what you did? Dawn snarled, as she pushed the massive cock all the way inside me. I thought I would split in two. My ass was on fire; it would never be the same. It felt like she was going to poke right through my belly button.

After a few excruciating moments the pain started to subside and as she kept fucking me it started to feel…good. The tip of her cock was touching a place inside me that I hadn’t known existed before. My own cock started to thicken and I hooked my ankles across Dawn’s ass in the same way I had done with Lou a few hours before.

She fucked me like that, thrusting into me and calling me nasty names until I came all over the inside of my pretty dress. When I was done she pulled her cock out and wiped the santorum (the frothy mix of lube and fecal matter that is sometimes the byproduct of anal sex, named after Senator Rick Santorum) on my dress and left me there alone.

Prom night was over and my pretty pretty Cosmo dress was ruined; soiled with grass stains, blood, ejaculate and santorum.