Let’s be real – hookup stories are so fun to gossip about. Oftentimes people don’t want to share their most embarrassing personal moments, but those can be some of the best ones. I mean come on, everyone has had an awkward or just plain funny sex moment at some point in time. Therefore, last year I reached out to my peers to share their stories. Their stories were so great that I’ve decided to collect even more. The following are 14 of the most painful, or just downright hilarious, sexual encounters that have occurred within the past year.
“My boyfriend lived in Towers directly across from the communal bathroom, and the first few times we hooked up, we were pretty eager. So one time, we were having sex, after having foreplay for a good while (all naked), when a guy called in, ‘Mind if I shut this for you?’ The door had been open the entire time, so every single guy on his floor who peed in that time got a quick show.”
“This guy I was dating had this amazingly cute dog. He went everywhere with it and it was part of his whole ‘sweet guy’ charm. Then it turned out he talked to me in bed just like he talked to the dog. Same patronizing voice, ‘Good girl’ etc. I was so out of there.”
“Once I was hooking up with a guy and we were making out. I wanted to make the move from his undies on to undies off but he stopped me and told me he had already finished earlier when we were just kissing.”
“Once my boyfriend and I were having sex on my couch and my mom walked by us to go to the bathroom. We froze and pretended to be asleep. But then she came back again and again. Turns out my mother has gotten minor food poisoning and we picked a very inconvenient time to do it. The best part was 2 days later she asked me if I ‘got some’ while he visited so she still doesn’t know.”
“So I had a crush on this guy forever, and I was constantly trying to talk to him. One night, I saw him at a party and chatted him up. I couldn’t believe that he was talking to be because he was just so hot! We got together later on and we were making out on his bed. All of the sudden, I felt something really wet against my upper lip and since it was dark I couldn’t tell what it was. I ignored it until he asked if I was okay. We turned on the light and there was blood pouring out of my nose. I was horrified.”
“One time I was hooking up with a guy and his penis was so small the condom fell off”
“The first time I met the guy I had a fling with last year, we watched ‘Step Up’ and cuddled. He tried to take it further, but I wasn’t having that. He later told me that that wasn’t actually his dorm room, and that he still lived with his ex-girlfriend. He tried to get with me on his frat brother’s bed.”
“All terrible sex stories start with a frat house. He left to ‘pee’ in the middle of sex with only a condom on. 30 minutes later I find him passed out in his own puke in the shower. Apparently he blacked out and forgot I was there. The worst part is that one of the brothers and that brother’s girlfriend saw him in the bathroom with only the condom on.”
“I thought a blow job literally involved blowing air, like whistling without sound. Good thing I didn’t like the guy that much and never had to see him again…”
“A few weeks ago, I was with this guy and he squirted right in my eye. I couldn’t see normally for a day or so.”
“I ran into an acquaintance while very drunk at a party and we started dancing and he offered me a tour of his house. We went upstairs and sat down on some sketchy couch and started talking. Then all of a sudden we were making out. He stopped and said he had to go to the bathroom so I said “I’ll be right here.’ As soon as he left the room, I threw up all over myself and ran out of the house. He called me after I got home to see where I went and I said I had to go home. Immediately after we got off the phone, I threw up all over my living room floor. Solid night and I’m pretty sure he never found out about the conditions under which I left. A few months later, we ran into each other again and started hooking up again, but this time I threw up in front of him. Surprisingly he still tries to contact me after all this lol”
“Once I was hooking up with a guy, and he got a nose bleed while eating me out. It got all over my private area…”
“I’m pretty into handcuffs and blindfolds. So one day while decently intoxicated I decided to handcuff and blindfold my boyfriend. I started giving him a blow job and I guess I was more adventurous than usual because I threw up. I literally threw up with my boyfriend’s penis in my mouth. I quickly ran away to handle that and later went back to business. The best part was that he was blindfolded so he had no idea what even happened until I told him later.”
“This isn’t directly sexual, but my boyfriend and I have handcuffs. One day we were cleaning out his room because his mom was visiting so I shoved them in my backpack and forgot about them for like a month. Well eventually I went to work at a hospital and I couldn’t find my id. In order to get in I had to go through security. I put my bag in the scanner and the security guy made a really odd face. He then looked at me really seriously and asked ‘Are you a criminal justice major?’ I, still not getting it, responded ‘No, why?’ to which he answered ‘I, uh, I saw handcuffs in your bag and wanted to make sure you didn’t have any weapons or anything.. No judgement.’ THE SECURITY GUARD SAW MY SEX HANDCUFFS AND DEFINITELY KNEW WHAT THEY WERE FOR. I’ve never felt more judged in my life.”
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