Jenna and I were randomly matched in the freshman roommate lottery. She wasn't a bad person to live with, but the two of us couldn't have been more different. She was a party girl with tons of boyfriends, and I was--to be blunt--a dork. Tall and skinny, with hardly any tits. Thick glasses and long, straight hair I always forgot to brush.
While Jenna went out almost every night, I usually spent evenings alone, either doing homework or watching anime in bed on my laptop. And that's exactly what I was doing the first time she brought Kevin home. I was propped up on my tummy, engrossed in the final episode of
Neon Genesis Evangelion
,, when they staggered in, banging the door and giggling.
They both were really drunk, and they tumbled into Jenna's bed, making out like crazy. I tried to ignore them, but it's pretty hard not to look up when your cute roommate is taking her top off so her boyfriend can suck her nips.
"Guys... I'm like
right here
," I said with a groan.
"So go watch your cartoons in the common room," Jenna said.
"Where am I supposed to sleep?"
"You can use my bed," Kevin said. "I don't think I'm going to need it tonight."
He was on already on top of Jenna with his pants off.
Kevin's room was just a few floors down, so I packed up my laptop and made myself scarce.
His roommate looked baffled when I turned up carrying my pillow and backpack.
"Who are you?"
"I'm Emily," I said matter-of-factly.
"And why are you here?"
"Your roommate is fucking my roommate in my room, so I'm sleeping here."
"Okay.... You can come in, I guess."
His name was Justin. I recognized him from my engineering classes. He had bright red hair and glasses. A dork like me.
He gestured at an unmade bed near the window.
"That's yours."
The room was a total wreck. Books and dirty clothes strewn everywhere. Boys are such slobs. And it smelled musty. Boy sweat.
I sat down dubiously on Kevin's bed, and Justin went back to his computer. There was a picture of a naked girl on the screen. I realized he must have been jerking off to her when I knocked on the door. I had the impression back then that guys needed to jerk off a lot, so I felt bad for interrupting him.
"Um... if you want to finish, it's okay," I said.
He looked at me like I had grown a second head.
"Seriously!?"
"Yeah, I'm actually kind of curious. I've never watched a guy... you know."
"Should I take off my clothes?"
"Just do whatever you normally do. Pretend I'm not here."
He stood up and pulled down his sweatpants. He wasn't wearing anything underneath. His thing hung down, long and thick between his skinny legs. It was bigger than the ones I'd seen in pictures. Despite been a dork, Justin was really hung. His pubic hair was reddish-blond, lighter than the hair on his head, and his big balls hung heavy in his loose sack.
Standing in front of me without pants was apparently a turn on, because his cock started to stir. It twitched a little with every heartbeat, getting thicker and harder as it filled up with blood. Pretty soon it was jutting straight out. It was the first time I'd ever seen a hard-on in the flesh, and the transformation was kind of impressive.
Justin was looking at me strangely. He took his erection in his fist and slowly started to jerk.
"Can you take off your clothes too?" he said.
"How come?"
He glanced back at the naked girl on his computer screen.
"I... uh... need something visual, in order to... you know."
"Okay. It's only fair, I guess."
I kicked off my tennis shoes and started getting undressed. Back then all my clothes were boring and shapeless. Baggy jeans, faded tee shirts and hoodies. I didn't have any curves, so what was the point in dressing to show them off? I stripped down to my bra and panties while Justin watched and stroked his cock.
"Underwear too?" I asked.
"Please." There was an edge of desperation in his voice. He really wanted to see me naked.
I reached around and unhooked my bra.
"Prepare to be underwhelmed," I said, pulling down the cups to expose my tits. I really was as flat as a boy, but Justin seemed to like what he saw, because he started stroking faster. Every once in a while, his hips would jerk forward. I could tell he was thinking about fucking me.
Watching him stroke was so fucking hot. My nipples were poking straight up from my tiny titties, and I was starting to soak through the crotch of my panties. I really wanted to join him and masturbate too, but I didn't know if he'd be cool with that. I was wandering in the wilderness, unsure about everything. I mean, I'd never even kissed a boy before, but here I was, practically naked, letting I guy barely knew jerk off to me.
Feeling like the biggest perv on the planet, I slipped my hand down the front of my panties and started rubbing my clit. Justin's attention was laser-focused on what I was doing with my hand.
"Now, take off your panties," he croaked.
What the hell. Why not? I lifted my butt off the bed and pulled my panties down around my ankles. My cheeks flushed bright red. I was mortified by how hairy my pussy was. The pretty girl on Justin's computer was shaved smooth, but my crotch was a messy thicket of dark curls. I'd never even trimmed. Why? Because I was a