Cringe-worthy one-night stand stories that'll make your bad choices seem lame

Cringe-worthy one-night stand stories that'll make your bad choices seem lame

SexFebruary 16, 2018 By Kylie Weinmeister

You’ve had ‘em, we’ve had ‘em, and according to our recent Ultimate Sex Survey results, 14 percent of younger generations (people under 35) are participating in them right now: the revered one-night stand.

But when mixing alcohol and strangers, those epic nights can sometimes lead to terrible outcomes. And what braver way to come to terms with what you’ve done than to tell the Internet all about it? That’s why we’ve gathered multiple responses from our readers about the worst, the most embarrassing, and the most cringe-worthy stories from around the globe.

Perhaps the following will make you feel better about your own drunken escapades.


“Okay, it sounds really wrong,” Hank*, a 27-year-old male, says.

“I didn't really know her very well, and we didn't grow up together,” he continues. “My dad married her mom when we were both 17. I only saw my dad for two weeks in the summer and holidays.

“I spent most of the time in my room on my computer. And her dad and just had another affair on her stepmom and her boyfriend dumped her about a month before. She had a lot going on.

“The last night before I flew home she came into my room and she was naked underneath her bathrobe.

“She asked if I was horny and then gave me a blowjob. I know I should have said no, but it had been about eight months since I'd had sex."

She climbed on top “and we had sex,” Hank explains.

The next day she was hungover.

“She told me she barely remembered it and we would never talk about it again. She's married now, and I don't think anyone else knows. We've never discussed it and I see her a couple times a year.”

The Nanny

Remember that one — or several — pornos of the girl who sleeps with the sexy dad she babysits for? Jen, a 20-year-old barista, actually did it.

“I babysat for this family periodically," she says. "They lived down the street from us growing up. The parents got divorced and the mom and kids moved out of state. When I was 18, the dad had the kids the whole summer. He hired me to be their nanny. It was great, because it paid well and I just needed a job until I left for college.”

He worked a closing shift two days a week and didn't get home until the kids were already asleep. Jen says he was talking to her one night and offered her a few drinks. Then she slept with him.

“He was my dad's age and his kids were asleep in the other room!” she sexclaims.

Jen says they had sex a few more times before she left for college. About five months later, her mom told her he'd been caught by another babysitter’s mom when she arrived to pick her up and that the girl was only 16.

“I felt used,” Jen said.  

Knocked Up

“That's my one night stand,” says Emma, a 19-year-old mother, while pointing to an energetic toddler working on an escape from his stroller to run around the coffee shop.

She laughs. “I won't tell him that though!”

Emma shares that she was at a high school party and she got really drunk. “I'm a lightweight and I had four shots and a couple of beers," she says. "There were these guys from another school. And I slept with three of them. I had only had sex once before. We didn't use protection and I wasn't on birth control. About three months later, there was no denying I was pregnant. I didn't even know the guy’s name.”

She says she regrets some of the choices, but never having her son. “It's been rough. But I wouldn't change it. He's my life.”

Sex for a Tattoo

Sarah G., 24, is a petite woman with bright red wavy hair. “Like Ariel the Little Mermaid,” she laughs. She reveals a side tattoo that stretches from her armpit to her waist.

It's a gorgeous piece of work, watercolor florals and geometric accents.

“I love the tattoo, but, it's not really a story I can tell a lot of people," she says. "Technically it was prostitution.”

Sarah recalls a time she met a tattoo artist at a party. She admired a lot of his work. “He’s really good and he had pictures of some of the stuff he'd done on his phone,” she said.

As the two kept drinking, Sarah confided that she wanted a large tattoo — she already had three smaller ones, but wasn't in a position to afford it and wouldn't be for a while. He offered to sketch something up and tattoo her, if she'd pay it off another way. Sarah says she went home with him and slept with him.

“I guess I'm lucky he actually followed through,” she laughs. “We're still sort of friendly, even now. But my sister says all the time she can't believe I'd get drunk and pimp myself out.”

More From Our Survey

“She was demanding I, "give her a baby" and wanted unprotected sex. When I refused she became angry and violent. I had to force my way out of her house and she followed me to my car still naked.”

“I went down on a lady, then noticed she had a bunch of cats and left without finishing.”

“Tinder gal was doing dabs and banging me while her kid was watching cartoons nearby.”

“Friends wedding. Hooked up with a cute waitress at the reception and took her to the bride's parents home and had sex under a pool table. Next day the bride's father was complaining about the loud sex he heard.”

“He kept lying to me about himself and gave me a landline for his phone number, and when I found he had a girlfriend, I told her what happened but found out months later they were still together...dumb asses.”

“After meeting a girl at the bar we walked back to her place and had sex. Afterwards, she told me to leave because she had a boyfriend and just used me cause she was mad at him. I left the used condom on her desk hopefully for him to find and get out of that nasty relationship.”

“Met this Irish girl at a bar while I was with the chick I was dating at the time. It started off friendly, but the Irish girl was clearly attracted to me. The girl I was with at the time was cool with it. She was all 'have fun, just be safe!' So I ended up back at the Irish girl's house.. … and she gave me Chlamydia.”

“After a night out in Cherry Creek, a random girl was giving me head in a parking garage elevator. She stopped at one point, looked up at me and asked: ‘Are you going to punch me in the face when you come like the last guy I did this with?’ I was all at once appalled, fascinated, and limp … so we went back to the bar … ”

“He tried to kick my cat. I kicked him out of my house into the snow, naked, and threw his clothes out afterwards. My cat lives here, you asshole. You don't.”

[cover photo by Ben White on Unsplash]