(It All Started With A Dare)

"There's no in any of the seven hells that I'm doing that!" I yelled, the sound echoing off the walls of the dorm

"You have to Blake, I mean you were dared." Sonya giggled, "Now Leslie, we'll need your black skirt, Jessica your purple top, and Connie, your wonder bra and grey jacket please. I'll supply the wig." At the mention of Sonya owning a wig, everyone in the room stared at her.

"What? Darrell liked brunettes." Heads were shook as each of the girls moved to retrieve their items and I shed my clothes on the stone floor.

"Oh." Sonya gasped. "Hey Leslie, grab your purple thong with the flying hearts on it would ya. Boxers simply will not do." Throughout the next hour, I was plucked, shaved, shoved, and stuffed, turning me into a curly haired brunette.

Three minutes before lunch ended, I walked up to the Brandon, the head jock of the football team.

"Hey there handsome, I'm visiting Leslie over break. I'm looking for someone to show me a good time." I purred, batting my eyes in what I hoped was a seductive manner.

"Hello doll. I'd love to show you around. I'm Brandon Johnson." The bastard slid his arm around my waist, leading me down the hallway.

"I'm Jen."

He took me to the movies, to some action film. Sadly I didn't get to watch any of it, to preoccupied keeping his hands from wandering down anything. After a quick meal at McDonald's he took me back to the school where the girls had swiped me a visitor's room earlier that afternoon.

The girl's had already been in the room, as luggage, clothes, and movies were strewn around the room, and a toiletry bag on the bathroom counter. We started making out and everything was going just as planned. Then my wig fell off and all hell broke loose.

"Holy fuck! You're not a chick!" he yelped.

""No shit Sherlock, neither are you." I dead-panned. "Now are we gonna do it or not?"

"Who tops?" I stared at him. "What? There's no law saying I can't be curious."

"I'll top, then you can." I shrugged, bending down to undo my strappy heels.

"Clearly I'm the more dominant here. I should top first." He crossed his arms.

"And unlike you, I know what I'm doing. So unless you're up for a very awkward doctor's visit, I suggest you swallow your pride."

"Fine." He huffed. Once we were lying naked, an unexpected bottle of lube was discovered under a pillow.

"Thank you Sonya." I thought as I slathered it on my cock. I was sure to take it slow and gentle; decreasing the pain I knew he'd feel the next morning. After I came we waited a while to restock our stamina before switching positions. Once his clumsy attempt was over its climax we fell asleep.

The next morning I woke at seven when Brandon was still sawing away at "Z's" and went to tell the girl's what happened like I'd promised. Afterwards I grabbed a couple of muffins from the kitchen before returning to my borrowed room. As I came through the door, Brandon was just waking up.

"Morning. Listen, you're probably really sore. A nice hot bath would help you immensely." I greeted.

"Thanks. We'll have to do that again sometime."

"I don't know what kind of guy you think I am, but I don't do the casual fuck thing. I'll do one night stands or relationships. That's it."

"Then I guess that means we're dating."

"What about your football buddies?" I dropped a muffin cup on the floor and started unwrapping the second one.

"Oh right, them. Could we possibly date in secret without the entire school knowing? I promise I won't sleep with anyone else. Hey, did you per chance get me a muffin?"

"I'll agree to secretive dating, but if you want a muffin, get it yourself." That was how I drug our football captain out of the proverbial closet and claimed him as mine.

(Visiting the 'Rents)

"And this is my little sister's room." I commented, throwing open the last door on the hallway, revealing I pink room filled with unicorns.

"Wow." Brandon said as he walked over and plopped onto the princess bed. He sunk down several inches as I walked over, causing me to giggle.

"This bed would be fun to play on." He stated.