17 People Share Their Most Brutally Cringeworthy Hook-Up Story

11. Mark

Last August I accompanied a college basketball team to Cabo San Lucas. First five days of the trip were game days, but the remainder of the trip was dedicated to partying. On the last night of our trip my buddies and I hit the infamous Squid Roe club for the fifth night in a row. I started dancing with this young lady, a couple things lead to another and she wants me to leave with her.

She doesn’t want to walk to my hotel, but she doesn’t have her room key.


In my drunken brilliance I declare we should hang out on one of the lounging beach chairs. It’s 3 am and the place is desolate.

We do the deed, I finish too quickly and in my guilt-ridden refractory period I offer to eat her out, to which she complies.

I’m nomming my heart out of her fantastic vagina when I hear, “excuse me, sir”


Local muscle had crept up behind me with my ass in the air and pants around my waist and told me and my similarly naked ladyfriend to GTFO, seeing as I wasn’t a resident of that hotel. Or something.

12. Seth

She shit on me during anal. I wish this were more interesting. (To be fair, it wasn’t a full-on shit, but it was like, not NOT a shit. She just sort of like, emitted poop onto my dick.)



Chelsea Fagan

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

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