Before we begin, submit your Hook Up Heroes stories here. Seriously. DO IT. We need entries. And not from freshmen in high school who blew an ill-timed load into their J.Crew cords during a dry-humping sesh only to be left to walk around an underage Smirnoff Ice party for the rest of the night with a cum circle the size of a drink coaster. Got it?
Today's story is more fail than win, but is awesome nonetheless. Because it involves asshole friends.
The fall of into my junior year of college, I started seeing an extremely cute friend of mine.
We'd hung out a lot, always in a platonic fashion. She was always dating someone. But our first day back, she told me things had just ended with her most recent boyfriend. That night, we were up until two a.m., making out.
She was gorgeous, with a pair of the most dreamy sea-foam green eyes. And phenomenal tits. Those were nice. I couldn't believe my luck.
Things progressed fast, as they tend to do in college, and within a week, we'd done everything short of sex. This persisted for a few weeks, until I asked her, late one Friday night.
“I really like you. I don't want our first time to be when we're drunk.”
Which is kind of hard to do in college. But I acquiesced to her request. Because not only did I like her, in lieu of doing it, she let me titty fuck her face off. And she was into it. Our first time, when I told her I was going to come, she simply nodded.
That made it pretty easy to hold out.
Then, one night a week or so later at the bar, she pulled me aside.
“I’m ready to fuck you.”
I should have immediately whisked her back to my place, but I had three good friends from high school visiting. I couldn't ditch them. Instead we stayed at the bar until last call, where my roommate invited a sizable group back to our place to polish off a keg.
After twenty minutes, her and I tried to surreptitiously slink away to my room. But my door faced the kitchen—and since the keg was in the kitchen—everyone saw us slip away.
We started going at it. Even though she said we could fuck, old habits die hard, I guess. Because I went for more titty fucking. I was going at it intensely, my ass pressed firm against her Xiphoid Process, when I heard one of my other roommates talking. I could only catch snippets.
“…There's no deadbolt…”
“…Maybe need a credit card…”
“…I could knock it over…”
At that last phrase, with my dick cruising through her rack like a Norwegian ship navigating fjords, I could only pray he wasn't going to do what he so obviously was planning.
The thunderous cracks of my exploding door frame an instant later told me otherwise. The whole setup gave out very easily, and my roommate, who'd come at it from a full sprint, came stumbling over the smashed door and flying at my bed., his head crashing into the top of my bed frame.
There he was, his head next to my girl's, his clothed body parallel with and inches next to our naked ones. Meanwhile, because I'd turned slightly from the commotion, my dick was pointed straight at his face. A foot away.
It was the closest I’d ever come to giving a man a facial. But that wasn’t the part of me that all of a sudden needed to exploded. No, the vicious rocking of a vigorous tit-fucking combined with the abrupt invasion of my bedroom upset my already-sloshing stomach.
I instantly dove off the bed and reached for my trash can. It was a mesh deal and didn't have a bag in it but it didn't matter, because it was already too late.
Meanwhile, everyone from the kitchen had followed my roommate’s surge and, unbeknownst to me, were standing in my room watching as I unleashed a naked, full-body convulsion that sent my digestive system in reverse and forced every shot and beer from the evening into my trash can, where it then seeped out onto my carpet.
After three pukes, I felt much better and turned around. There I was, standing naked, rivulets of stomach acid and vomit dribbling down my neck and chest, as nine people stared at me.
I put one hand over my penis and waved.
After a moment, some lone voice of reason told us to be left alone. The girl started dressing in the far corner of the room. She told me she thought it would be best if she left.
We never hooked up again.