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6 Celebrities Share Their Worst Hookup Stories

I’m sure we all have our fair share of awkward sex stories. Maybe it was when you lost your virginity and he poked around for 10 minutes trying to find the hole with no luck. Or maybe it was last week when your period came early all over his white sheets. I’m honestly cringing just thinking about it all of my embarrassing sex stories (and trust me, there are a lot). But once you get past the embarrassment of accidentally letting one rip while you’re doing it, it makes for a great story down the line. And what’s better than your own embarrassing sex stories?  Embarrassing celebrity sex stories. Whether it makes them seem more human or makes me feel better about myself, awkward celeb sex stories are sooooo amazing. Hearing of the most awkward times our fav celebrities were having sex and it went from romantic to embarrassing v fast is extremely enjoyable. Here is a list of some of the best embarrassing celebrity sex stories, for your viewing pleasure.

Kris And Caitlyn Jenner

Back when Kris and Caitlyn were still married, they had a rather rambunctious sex life. I don’t think I need to remind you of when Kris accidentally slipped Rob a Viagra, or how they used to have a stripper pole in their bedroom. But one time, the couple was flying a commercial airline *gasp* (don’t worry, they were in first class). They decided to join the prestigious Mile High Club. How people actually do it, I don’t know. But they did their thing and “felt they got away with it.” Until the flight attendant got onto the speaker at the end of the flight to congratulate the Jenners on joining the club! They were given a bottle of champagne to celebrate! Honestly, that flight attendant should get a raise.

Khloé Kardashian

Honestly, this embarrassing celebrity sex stories list would not be complete without another Kardashian/Jenner family member. In 2016, Khloé wrote on her app and website about the time she had sex in a moving vehicle. She rated it a “two out of five” because it was v uncomfortable and “hurts her f*cking knees” since she is tall. She clarified that this all went down in the backseat, though, so neither she nor this mystery man were driving. So my only question is, who TF was driving?!

Paris Hilton

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Hilton lost her virginity at 15 to Randy Spelling (Tori Spelling’s brother). And while most people’s first times are not their finest moments, this one takes the cake among these embarrassing celebrity sex stories. He said that after they snuck off to have sex, “I hear this knock knock knock on the door, and I look out and her grandma’s there. And then I look out the window and I see Paris in a full-on dress with a suitcase running down the golf course.” First of all, what was in the suitcase? Why did Paris take it with her? And also, I wonder what he said to her grandma …

Nick Cannon And Mariah Carey

In an interview back in 2012, Cannon admitted that he and then-wife, Carey, would get down and dirty to her music. And when Carey isn’t there? He masturbated to her songs. Um, wow. That is a new level of narcissism. Their favorite song to have sex to was “Hero” and honestly, I’ll never be able to listen to that song in the same way again. It may not be embarrassing for them, but I definitely have some secondhand embarrassment hearing about this. It seems a little weird, but whatever gets you off, dude.

Cara Delevingne

Cara admits that she is a frequent member of the mile high club, but there is one story that stands out. She was once having sex on a plane in the chair (yes, not the bathroom) and some guy kept watching them. I mean, wouldn’t you at least take a peek if people were getting it on in the row next to you?? Instead of stopping, as any logical person would, they asked the stewardess to ask the man to stop watching them so they could continue. Sure, that’s a normal reaction. She recalls the situation as “disgusting” and called him a “pervert” but like, do you blame him for staring?

Ariana Grande And Pete Davidson

Keep in mind that Davidson has a tendency to overshare. He told Howard Stern in 2018 that he always thanks Ariana for having sex with him and always apologized afterward. If that isn’t awkward enough, he told Stern that he has a trick to help him last longer in bed. He said that he thinks of his father, who was a firefighter who died in 9/11, “being burned alive.” I’m not a guy and don’t experience boners. But that seems like an automatic boner-killer, rather than just a technique to help you last longer. I’m truly uncomfortable. Then again, Pete is known for openly talking about his dad’s death and joking about it, so it is very possible he’s not being serious. At least, I hope he’s not.

Images: Shutterstock; Giphy (4)

Carrie Betchshaw
Carrie Betchshaw
I'm just a regular 'ol Toronto gal who just so happens to publically write about her sex life online.