50 Women Reveal The Raunchy Details Of Their Biggest Hookup Mistake Ever

47. Got killed by doggy-style

Oh man, decided to hook up with this guy once while hanging with a bunch of friends. We went off into this walking closet and went at it. Very well endowed, I might add. It was really good and everything was going okay, we decided to switch positions. So fast forward to doggy style and I swear I’m pretty sure I died.

Everything was vaginal and it one quick second he slammed straight into my ass. I reallllly commend him on the accuracy…like he didn’t miss a beat with his thrusts and went straight in. I lost my breath and could barely talk but I managed to tell him to get it out. For some reason he was certain that I had done anal before (i had not). Regardless, his rather large dick was not something to just thrust into any vagina without warning. I hate him and we still laugh about it to this day.

— live4asmile

48. WTF dude

The guy who gave me herpes. Womp womp

— Princess_Trash_Panda

49. Got buttered up into sex

Not that bad, but a long time ago my friends hot older brother acted like he was really into me. He buttered me up like he was interested in a serious relationship (serious for HS).

After a very awkward hookup, he totally ghosted. I regret it because 1. I felt tricked and used 2. It occurred to me after the fact that I hurt my friend 3. Turns out, 10 years later, he’s a conservative Trump supporter who seems to hate women (according to his Facebook posts)

— Thomzzz

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