17 People Share Their Most Brutally Cringeworthy Hook-Up Story

9. Ashley

I was freshly-single and (way too) ready to mingle, so I thought I would preemptively cockblock myself by wearing one of my roommate’s shirts. (My shirts, and bras, seemed to disappear at the slightest hint of a hookup, which was a problem because once your top is off, your pants soon follow.) She was a proud member of the Itty Bitty Tittie Committee, and I was proudly not. This shirt took 3 sets of hands to squeeze me into — there was no way it was gonna be coming off easily. Later that night, I found myself in the bedroom of this guy named Rusty. Never has anyone looked more like a guy named Rusty than Rusty. The 3 sets of hands that had helped me earlier where in various other bedrooms in the house making mistakes we would laugh about the next morning.

I make some asinine, albeit true, comment about how one of those girls (my roommate) was a virgin. “Haha, she doesn’t know what she’s missing out on!” I said. Totally, embarrassingly leading him on. (100% not my intention.) So he thought I was about the peen, which I am, of course, just not that night.

We started making out. Then he tried to take my shirt off. Poor guy didn’t have a chance. But oh, did he try. He tried real hard to get that shirt off. At one point he was squatting on the bed behind me using both hands. I was giggling like a damn fool because my evil plan had worked. He gave up on my shirt and grabbed a rubber.

“Hahh, um, nooo. I’m good. I think I hear my friend!” I panicked.

“Wtf!” He accused.

“I’m in my period, dude, sorry.” Another asinine, and totally false, statement.

“I don’t believe you.” I’m sure he could already feel his balls going blue.

I asked him if he wanted to see my tampon string.

He declined.

I ended up sleeping the too-tight shirt, alone, in my own bed, that night.

Preemptive cockblocking FTW.

Sorry, Rusty.

10. Shae

This guy I went to high school with and always had a thing for (we both always had our own gf/bf) came up to visit me during my birthday weekend my freshman year in college. 3 day weekend. 1st night we successfully made out at a frat but I was extremely drunk & proceeded to puke (very neatly btw) into a solo cup. Night 2: we went to a house party and he was in the basement grinding with a rando all night. Night 3 rolls around and I finally get this idiot into my room. He keeps having to go to the bathroom and eventually just ends up puking in my trash on my dorm floor. I woke up the next morning and he had slept in my roommates bed. Cool!!

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Chelsea Fagan

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

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