17 People Share Their Most Brutally Cringeworthy Hook-Up Story

3. Nicole

Upon going home for winter break a few semesters ago, I realized that I hadn’t really planned for most of my old friends having jobs and actual things to do instead of hanging out with me. One afternoon, I decided to combine the trifecta of foolishness: boredom, horniness, and Facebook. Scrolling through my timeline, I stumbled upon a former high school classmate that I had once hooked up with. I decided to act on my recklessness, and after a brief and thirsty conversation via messenger, he was texting me that he was outside.

I had the entire house to myself, because my mom was working a night shift and my dad wasn’t due back until midnight. Me and my one-nighter had one of those incredibly awkward conversations that only precede pre-arranged sex; I think I asked him how school was going (he wasn’t enrolled). The foreplay was clumsy and since he’s about a half inch shorter than me, limbs and members were getting accidentally bumped and pushed. Fortunately, once we finally got into it, it was glorious.

The only thing I had remembered about this guy was that he was pretty well endowed, but either my memory was modest or those infomercials about growing your dick aren’t lying because homeboy was packing. He was stroking it from just the right angle, and I was beginning to feel the tingling tension signaling a coming orgasm in my toes. I wrapped my legs tighter around him and gripped him in a hug.


I stopped him for a moment. Was that the garage?


FUCK! It was the garage! My dad was home early! “Shit, shit, shit!” I hissed, and threw the guy off me. It’s important to note that at this point, in the deep throes of sex, my pussy had gone into gripping mode (shout out to my daily kegels). My vag hadn’t fully unclamped, so when I unexpectedly pushed him off, this guy squealed. Like a piglet. Jesus H, I thought, is he fucking coming right now? He was. All of this happened in about 5 seconds. In the next 5 seconds, I scooped up his clothes, threw them at him, and started hissing at him to get dressed. I hurriedly tied my robe as I heard the garage door motor stop. I figured I had about 60 seconds to get my booty call down the stairs, through the living room, and out the sliding door to the back patio before my dad walked in and I had to explain this shit. The guy didn’t even have his shirt on yet. I didn’t care.

“Come ON!”

I grabbed his arm and manhandled him down the stairs like a rag-doll. It was at this point that it really hit me he didn’t have on a shirt. It was somewhere around 30 degrees outside since it was around christmas. When I slid open the patio door, he shivered. I pretended not to notice.

“Just go down the deck stairs and through the gate.”

“What about my shirt?”

“I’ll give it back later!”

BBBBBRRRRrrrr. That was the garage going down. That meant I had about 10 seconds, tops.


I shoved him out into the wintry air and he gave me a puppy dog face as I shut the drapes. I turned around and my dad opened the door.

I was breathing so hard at that point, and I didn’t want to give myself away. I mumbled a hello to my dad and ran back upstairs.

In my room, on the floor was one of those gaudy sweatshirts with a gold foil design on the front.

My phone bleeped with a new notification from the booty call:

So that was fun, huh ;)

4. Julie

I’d just broken up with a boyfriend and was feeling in the pits of despair and so I went out with some people who I didn’t even know that well. We went to a house belonging to a guy who I did not know at all. And I was really fucked up on all the substances and ended up inviting him back to my house, where we started messing around and eventually having sex. Then I started thinking about my ex and started crying. While we were having sex. I ended up kicking him out of my apartment without his shirt on and to this day I do not know for sure if I ever got his name.



Chelsea Fagan

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

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