20 Celebs Reveal The Crazy Way They Lost Their Virginity

Even the sexiest celebs have awkward first-time sex stories.

20 Celebs Reveal The Crazy Way They Lost Their Virginity DFree & Everett Collection / Shutterstock

Many celebrities don't seem to be afraid to get candid about their first time. 

Thanks to the lack of barriers when it comes to fame these days, many celebs have spilled the dirty and juicy details about losing their virginities. What's most surprising to us is how young most of these celebrities were when they had sex for the first time.

Which hot TV actress has only slept with one person? Which rap star tried to lose his virginity at 7, but failed? And which reality TV star asked her mom for birth control when she decided to have sex?


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Find those answers and more in these celebrity virginity stories!

1. Angelina Jolie

It's no surprise Jolie has a wild side between the sheets. But the experience she had at 14 led to some darker moments for the actress.

"I had started having sex with my boyfriend at 14 and the sex and the emotions didn't feel enough," she said in a 2007 interview. "In a moment of wanting to feel closer to my boyfriend, I grabbed a knife and cut him. He cut me back. We had an exchange of something and we were covered in blood, my heart was racing.


Then whenever I felt trapped, I'd cut myself. I have a lot of scars. It was an age when I felt adventurous and after a few beers, things happened."

2. Kim Kardashian

Before Kim Kardashian was a reality star known for making a sex tape with Ray J, she was just a 14-year-old virgin who wanted to have sex with her first boyfriend of four years. So, who did she tell? Mama Jenner, of course!

"I'd say around late 14 or early 15 [I lost it]," Kardashian revealed in a 2012 interview. "We were so in love. I thought we were going to get married. I brought my mom in my bathroom and I'm like, 'Mom, I think I'm gonna have sex. I think I should go to the doctor and get put on birth control.' And my mom was like, 'Okay.' What else was she gonna say?"


Safety first, Kim.

3. Matthew Morrison

The former Glee star held onto his virginity until he was 21, thanks to a high school girlfriend who would suggest praying any time things got too hot and heavy. "It was sweet," he said. "It was innocent."

Then, with his v-card cashed, Morrison took advantage of his odds as one of the few straight guys into musical theater in NYC.

"There was so much opportunity," he said in a 2010 interview. "There were all these beautiful, beautiful dancers. As a straight guy, I had some room. There were the shared interests in singing and dancing, and I always find dancing with someone very evocative and sexual.

I definitely hooked up with a lot of girls when I was a young guy on Broadway. It was exciting. Very joyous and free."


4. Tina Fey

It's not a secret that Tina Fey didn't lose her virginity until she was 24. But did you know she lost her v-card to her now-husband, Jeff Richmond? That just doesn't happen very often anymore!

"I just couldn't give it away," Fey once revealed in her memoir, Bossypants. "I remember bringing people over in high school to play — that's how cool I am — that game 'Celebrity.' That's how I successfully remained a virgin well into my 20s, bringing gay boys over to play Celebrity."

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5. Kelly Osbourne

The star wasn't so much worried about the awkwardness of sex at 13 as she was about the consequences. "I convinced myself I was pregnant," she has said. "I hadn't even gotten my period [yet]." 


6. P. Diddy

If at first you don't succeed, dust yourself off and try again. Diddy knows that lesson all too well.

"I tried to lose my virginity when I was seven years old," he said. "I was on top of a girl who was 9 or 10, but it didn't happen — so everybody doesn't have to bug out! [I lost it] when I was 13, and I felt I was a porno star because I'd been watching porn for so long.

In the Bronx, you could get a hotel [room] for an hour. I always had $20 or $30 to take a chick to a hotel. I'm proud to say I love sex. You might catch me in a porn store at any given moment—it ain't nothing I'm ashamed of."

Thanks for that, Diddy. TMI.

7. Shia LaBeouf


At age 18, LaBeouf's first time had the actor falling back on his acting chops.

"I was trying to portray myself as a man who had done it many times in the past. I didn't tell the girl I was a virgin. I was all, 'Don't worry, babe. I'm gonna handle it tonight,'" Shia revealed in a 2009 interview.

"And meanwhile I was shaking in my boots. Getting naked was very strange. It was the first time I'd been naked in the light, in front of a girl, with no hiding place. I remember putting a pillow underneath her because I had seen that in a porn movie. It put her at a weird angle, where I couldn't get in correctly. I'm not extremely well-endowed and clearly this wasn't the move."

8. Jessica Simpson


At 22, Jessica Simpson gifted Nick Lachey with her virginity on their wedding night. The pop-diva-turned-fashionista had famously abstained from sex until she said "I do."

And now, she's embraced her sexual side, having been called "sexual napalm" by ex-BF John Mayer and having three kids with her husband, Eric Johnson.

9. Nick Cannon

He married Mariah Carey, who was 11 years his senior. But did you know Cannon has been into older women since he was a teenager? The singer lost his virginity at age 14 to an older gal.

"We were in a sleeping bag... I said we should change positions, she was like 'just get off me!'" he said in a 2010 interview. "She ran into the bathroom with all of her friends and they were in there laughing. I vowed from that day forward no woman would ever laugh at me in the sack again. I actually ended up crying at the end of the whole ordeal."


No worries, Nick. 

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10. Fergie

Though Fergie oozes sex appeal, she also knew her virginity was something worth holding onto until she knew she was ready.

"I've always been a very sexual person. I've always had to hold myself back," she said. "I lost my virginity at 18. But that took a lot of willpower."

11. Matthew Fox

Sex isn't always romantic — and Matthew Fox learned that his first time.

"I was 12. She was about two years older than me. It wasn't her first time. I can actually see the event in my mind's eye, like photographs," he explained. "It was in Dubois, Wyoming, where the population sign probably says, to this day, about 1,000.


It happened, literally, on the ground by a river while a rodeo was going on in town... it was absolutely terrible and awkward — just two kids lying down and pulling our pants down." 

12. Khloe Kardashian

Similar to her sister, Khloe lost her virginity at age 14. But she immediately regretted having gone all the way at such a young age.

"I should have listened to my parents," she said in a 2012 interview. "Don't let anyone pressure you, it's not worth it and how I felt afterward."

13. Daniel Radcliffe

The man we all know and love as Harry Potter started having sex at age 16, which is the age of consent in England. A little weird, right?

Radcliffe has said he celebrated his sweet 16 by doing the deed with his older girlfriend, Amy Burne, who is now his ex, at the time. And he didn't even have to put a spell on her!


14. Ashton Kutcher

The actor described his first time at age 15 as "horrible."

"It was out in the woods and it was horrible. It was a girl I'd just met who my buddy set me up with," he said in 2008. "The whole thing lasted like two seconds. It was really awkward. Two years later, I had sex with her again just to show her that the first performance was a fluke and I'd gotten much better."

We're sure Mila wouldn't disagree.

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15. Will Ferrell

You'd think being funny would help get women. But that's not the story for Will Ferrell, who lost his virginity his junior year of college. That doesn't mean he didn't try as a high schooler.


"In my mind's eye, it seemed like the way it was supposed to happen," he once said.

During his high school days, his mom had assumed his first time took place with a flirty high school classmate. "She said, 'If you slept with this girl, you'd better slap a condom on that pecker of yours.'" 

16. Katy Perry

This singer's first time wasn't as spectacular as fireworks, instead it was actually quite normal! Like a lot of teenagers, she revealed that she fooled around, "in the front seat of a Volvo sedan while listening to Jeff Buckley's album Grace."

17. Paris Hilton

This rich socialite wasn't going to lose her virginity in the back of a car like most teenagers. Her first experience was with Randy Spelling, and he spilled all of the details.


"We went to Palm Springs once for the weekend, and we couldn't check into the hotel under her name because her grandma was looking for her," Randy said in a 2007 interview. "She was, like, 15; I was 17. And what do you know, 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. We broke up like a week later."

18. John Stamos

It looks like Uncle Jesse learned a few things from his older friend, and the connection stayed!

"I think I was almost 18," John Stamos said in 2013, "and none of my friends had really done it yet. I wasn't a geeky kid, but I was sort of... innocent. And then I was driving home with the sister of the bass player from my high school band, and she dropped her keys in my lap — my crotch area — and went to grab 'em. And I thought, 'Oh. This might be on!'


And she was this beautiful woman who was maybe five to seven years older than me. So we went to her house, and she was very gentle, and easy, and walked me through it. And it was fantastic! We're still friends."

19. Russell Brand

The British comedian's first time was done abroad — with prostitutes!

"On day one we went to some sleazy dive. Before long I was sat on a bar stool with a Filipino called Mary-Lou. Then we were leaving in a cab with three Asian prostitutes my dad was drunkenly herding," wrote Brand in his 2007 book, My Booky Wook.

"Back in the hotel my dad set about unwrapping his two prostitutes. I sat on the edge of the other twin bed. She must have known I was a virgin as soon as the bungling encounter commenced."


20. Johnny Depp

Fame certainly makes you grow up faster, and that's also true for this actor. At the young age of 13, Depp lost it to a groupie while he was in the band, The Flame. He did the deed in the backseat of a car.

21. Dustin Hoffman

This actor's first time is fitting for a comedy! At age 15, an older woman at a New Year’s Eve party mistook The Graduate star for his brother. They then went into a dark room and got frisky.

22. Jason Segel

This is another actor who got lucky out of some trickery. The funny man came up with a little white lie to impress the ladies.

"I taught myself to play piano when I was 17 to pick up girls... the first thing I did was I found a really not-that-intelligent girl and I told her that I wrote 'Your Song,' by Elton John. I was like, 'I wrote this for you.' And then I lost my virginity," explained Segel.


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Sloane Solomon is a YourTango editor and writer who covers pop culture, lifestyle topics, and love and relationships.

Editor's Note: This article was originally posted in April 2015 and was updated with the latest information.