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

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God and Man
God and Man

1. Checking my oil

I hooked up with this guy a few times who I had good chemistry with. He wasn’t bad in bed but he was so freaking awkward about sex.
We were making out naked, and he hadn’t touched me anywhere between my legs.

He decides it’s penetration time and gets up to get the condom from the bedside table. Before opening the condom and putting it on, he reaches down and puts one finger inside me and takes it out in one movement, then puts the condom on. With no words. I felt like he was checking the oil.

— justalittlewave

2. We just had sex and then…

Had what I thought was just going to be a one night stand with a dude. In the morning he confessed that he’d been interested in me for years and that his dreams had come true and started talking about our future. It was very awkward.

— ConnieC60

3. Blood. Blood everywhere

Hooked up with this cute guy for a night, both of us just wanted a one night stand or a FWB at max. We started having sex and it was pretty great, felt good then suddenly he pulls out and his condom is COVERED in blood. Like covered. I got really freaked out and told him embarrassingly that my period is a little weird to which he said (to my horror) “it isn’t you, it’s me”.

I just looked at him trying to understand how he could have been on a period (my brain was not working) and then he took the condom off (which now had a mix of semen and blood in it, SORRY for the TMI) and showed me some stitches on his penis that had ripped during sex (he said I was too tight). He also said “can’t believe this happened again”. Thankfully nothing was on me, I washed up and left and we never spoke again.

— ynok822

4. Wow, this guy really sucks

The guy who I thought was using a condom but I guess in the middle of sex, he took it off (I was very drunk and didn’t notice). Did not even know until I was showing symptoms of chlamydia and I had to ask him about it. Biggest scare of my sex life.

— cheechnfuxk

5. Not exactly sex but

Met a guy at a bar. He seemed clean, law abiding, kind. He came over. Start making out, took off my bra, suddenly pulls a crack pipe out of his pants and asks if he can “do this quick here or should he use the bathroom?” Asked him to leave and he did. Kept texting me afterwards saying he doesn’t need to do it in front of me, he found a kmart parking lot to do it in and he can come back. I blocked him.

— Gialicious

Brittany Cox

Ontario real estate specialist. I write relationship advice, #GuysInsight, sex, and snark.

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Depression is real. Anxiety is real. PTSD is real. ALL mental illnesses are real. Don’t believe anyone who is trying to tell you otherwise.

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“This place was amazing! The pictures just do not do it any justice—what a large and beautiful space that is tastefully appointed and well-thought out. Really loved writing on the chalk boards and cooking breakfast for my girlfriend in the wonderful kitchen.” — Schoolhouse guest, Jeff
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