Men and women describe their worst, and most hilarious, one-night stands

Men and women describe their worst, and most hilarious, one-night stands

SexSeptember 01, 2016 By Staff

Everyone knows the feeling of a one-night stand: That bittersweet realization located at the crossroads of lust and drinking too much. Some people wake up feeling joyous, while others wake up staring down the nasal cavity of a bad mistake. We compiled responses from our 2015 Ultimate Sex Survey, where we asked anonymous participants what was the worst one-night stand they’ve ever had. We didn’t think it could get that bad. But it does. They told us everything.

“She woke up and hopped out of bed ‘who are you, I'm not that kind of girl' to which I responded, ‘Uh, I've known you for five years and yes, you are that kind of girl if you responded that way by default, without double checking who I was."
-----

“Whiskey dick led to a surprisingly helpful penis pep talk in the bathroom. Finally got the condom on and then three pumps in, her hand broke the window. She was bracing herself against it and cut her wrist. She passed out at the sight of blood and the police showed up.... so yea that happened...”
-----

“Her kid walked in on us.”
-----

“Got too drunk and the guy pissed in my bed.”
-----

“Had partially clothed period sex on Farrand Field. Guy was wearing white shorts. Enough said.”
-----

“Was fucking a girl in the backyard of a party when her drunk friend needed her to hold her hair while she puked and call her an Uber. We planned to get back to it when the situation was handled so I went to take a leak and as I did I noticed the head of my penis swelling very rapidly. My first thought was immediate onset AIDS but when the head got obnoxiously large all of a sudden, pop! The condom I forgot to take off finished filling up with my piss and basically splattered on my pants. I went back to the party where I started dancing with who I thought was the same girl as before, called a cab, then got upstairs to the light where I realized it definitely wasn't. But she was down so I got laid a second time. Started out pretty bad ended up pretty good.”
-----

“After we were done, she left and I though everything was cool. The next morning she arrives at my house with an over night bag and a frozen pizza. The pizza was Tombstone.. so yeah.. it was all bad.”
-----

“The guy and I were arguing at the bar about the existence of Jesus. The bar was closing and he wanted to continue the conversation back at the house where he had access to his beloved Bible. For some reason I agreed. At his house we drank more and he proceeded to read me passages out of the Bible. Then we had sex. Still regret that one.”
-----

“She woke up and said she was pregnant but there was no penetration.”
-----

“I was going down on this girl that I took home from the bar and she farted. Silent, but it was sour as hell. I manned up and finished and was repaid with a blow job involving a lot of teeth. :/ ”
-----

“This girl never had crazy sex before. One, she came everywhere (didn't notice the cum stains till two weeks later; I was sleeping in that. Whatever). Two, she was allergic to latex, and insisted using a condom leading me to go on a hunt for latex-free condoms. I was only able to find reduced-latex condoms. Over it. Three, I couldn't fuck her like I wanted because the condom was irritating her pussy, so I had to take it niiiicceee and sloowwwww (she didn't even suck dick). Eventually I fucked her, and when I came, her response was, ‘Did we just pound?’”
-----

“We started having sex and she began to violently claw my back and moaning loud. I switched from missionary to girl on top to stop the pain (and probably the bleeding) but as she’s riding me, she starts crying about her ex-boyfriend. I end up talking to her for a few hours then head to bed. Before I can fall asleep, she throws up all over my floor. Yea, I end up taking care of her for the rest of the night.”
-----

“Everything was going great until she looses it when I cum in her. She proceeds to makes things awkward by calling her friend and telling her how miserable she is. Gets to the point where I have to tell her to leave.”
-----

“Lost my virginity to her, and she totally asked me mid-sex if I was a virgin. I lied and she looked at me like, ‘Come on. Yeah right.’”
-----

“Picked up an older women from a 7-Eleven that said, ‘Where's the party?’ To which I said, 'follow me!' Once the drunk wore off, I realized the mistake I had made. She stayed the night and was still there when I woke up...never again.”
-----

“She got pregnant. Now we’re married.”
-----

“I was in the middle of hooking up with a girl in college and went to grab a condom but didn’t have any so I went into my roommates stash and grabbed a random condom. I put it on and we started going at it. About 30 seconds in, I become aware that I can’t feel my penis. I immediately start thinking the worst: STDs, ED. I wait a minute to see if the feeling will come back. It doesn’t. It gets more numb. I end up faking an orgasm so she’d leave and run into the bathroom and pull the condom off. I look at the wrapper and it’s an extended pleasure condom with a numbing agent. Eventually my little guy comes back to life making that night the worst and best night of my life.”
-----

“This guy ended up buying me drinks all night and it was apparent we were going to end up hooking up. Me, him, my roommate and his friend all ended up going to his friends house to stay the night. Back at his house I started feeling the spins and ran to the bathroom to throw-up. I cleaned it up, rinsed out my mouth and pretended it never happened. I ended up fucking that guy on the couch and woke up in the morning to him on the phone with his girlfriend, 'See you soon, Love you babe.' I pretended to sleep as he left to go get picked up by his girlfriend and kissed me on the cheek. Worst part was I woke-up with a 20-minute Uber ride away from my hotel.”
-----

“Had one-night-stands on both Friday and Saturday with two different guys. When the guy on Saturday found a used condom in my bed during giving me oral, he got turned off and went home.”
-----

“Drunk, best friend, sister downstairs.”
-----

“He woke me up trying to joke around with me and made me breakfast in bed ... I didn't even remember meeting him. Whoops …”
-----

“He actually used his hand to shield his face from me when we ran into each other at lunch the next day.”
-----

“He pulled some of my hair out.”
-----

“Afterward finding out the guy was an acquaintance's boyfriend.”
-----

“He put it in the wrong hole and wouldn't admit it. Then wouldn't leave when I told him too.”
-----

“A while back, I knew this guy who was a hot body builder. Not the kind that's scary big, but the kind that was still of normal proportions yet hard as a rock. He was incredibly cocky and popular, not usually my type, but hey, experimenting is fun. Anyway, one night we went out for drinks and hooked up. I was so excited when it started, but was disheartened by finding out he had a four or maybe five, at best, inch penis. He had seemed like he would at least definitely know what he was doing, so I got into it again. Literally as soon as he put it in, he came. And, not only did he cum in like less than a second, but then he collapsed on me and cried for a good twenty seconds before I squirmed my way out from under him and left after an awkward 'goodbye' wave in his direction.”
-----

“The night I lost my virginity ... to a one-night stand. I came back into the room (which my roommate and I shared at the time and both brought home dudes that night) the next morning after brushing my teeth and he was crying about his ex girlfriend.”
-----

“I had to physically leave before throwing up. The only bathroom in the house had dried up shit and vomit stains.”