"As he took his pants off I thought to myself, holy moly . . . "

Anthea Levi
December 14, 2017

Ever experience a hookup that started out so, so promising—and at some point turned awkward, embarrassing, hilarious, or simply left you thinking WTF? Yep, been there. Rather than walk around feeling like you're the only person to deal with a bizarre bedroom fail, take comfort in the hookup horrors other women have gone through. Here are eight stories of sex gone wrong that made these women laugh, wince, turn crimson, or grab their phone and text their group chat the crazy details immediately. 

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Bloody mess

“When I was in college, I had just started hooking up with my current boyfriend. He was going down on me, and while he was doing it, he got a bloody nose all over me, himself, and my sheets. It was quite the memory.”

His special package

"I was hoping to have a friends-with-benefits thing with my cute neighbor, so when he invited me over one night, I thought it was my chance. We were getting flirty, and then he left the room momentarily. While he was gone I looked around and saw an open UPS package. I’m a snoop, so I decided to take a see what was in it . . . a penis enlargement pump! That was such a turn off, I made up an excuse to leave and never came over again."

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Sticky situation

“When I first started hooking up with one guy, we had a sticky encounter one night. After we finished having sex, he told me that gum accidentally fell out of his mouth and into my hair during doggy style. I then had to cut a chunk of my hair off from the back of my head to get it all out.”

Size matters

“I’d messed around with one guy several times, and tonight was the night we were going to have sex. But as soon as he took his pants off I thought to myself, holy moly…that thing is not going to fit in me. His penis was huge! I immediately backed away, and his expression changed. It became clear that he had experienced this same reaction with other women. “Don’t worry, we can use a lot of lube,” he offered. He was a sweet guy and we had great chemistry, but I know my body. I ended up feeling really sorry for him.”

Orgasm accident

“One time when my ex-boyfriend and I were having sex, he ejaculated and somehow it got all over his face and into his mouth. He was freaking out—I was laughing so hard.”

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Allergic reaction

“Just after he entered me, the guy I was with finished really fast. After it happened, he said he’d need to wait a minute to get hard again so he could then focus on my pleasure. When I told him he could just go down on me instead, he claimed that he was allergic to latex—and the fact that he had just been inside me with a condom meant that he couldn’t perform oral sex or he might have an allergic reaction. I laughed in his face and told him that that was both the worst and funniest excuse to not go down on someone I had ever heard.”

Wedgie weirdness

“A guy I was seeing had a bizarre approach to foreplay. Every time we started hooking up, he would grab my underwear in the back and yank up really hard, giving me a wedgie. The worst.”

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Frustrating first time

“I was all ready to have sex for the first time with a guy I had been seeing. I had a candle lit, slow jams in the background, and lingerie on under my clothes. When he walked in my room, I took my dress off. Surprising him seemed to completely through him off, because he couldn't get it up. After 10 minutes, I rolled over to get my phone and called my best friend to give her a blow-by-blow of my attempted sexual pursuit....in front of him. I'm not proud of how insensitively I handled the situation. In my defense I was only 20. Luckily he made it up to me the next day."

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