20 Brave Celebs Reveal The CRAZY Way They Lost Their Virginity

20 Brave Celebs Reveal The CRAZY Way They Lost Their Virginity

20 Brave Celebs Reveal The CRAZY Way They Lost Their Virginity

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

Bow chicka bow—OW! Post-coital, even celebs have wondered, "Is that it?"

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? Find those answers—and more celebrity virginity stories—below:

 

Virgin Diaries

Angelina Jolie
It's no surprise Angie 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 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."

 

Virgin Diaries

Kim Kardashian
Before Kim K. was a reality star known for making a sex tape, 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]," Kim said in an interview. "We were sooo 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.

 

Virgin Diaries

Matthew Morrison
The 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, v-card cashed, Matthew took advantage of his odds as one of the few straight guys into musical theater in NYC. "There was so much opportunity," he says. "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."

 

Virgin Diaries

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," Tina revealed. "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."

 

Virgin Diaries

Kelly Osbourne
The newly-engaged 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 said. "I hadn't even gotten my period [yet]." Pregnancy scares happen to the best of us, Kel.

 

Virgin Diaries

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.

 

Virgin Diaries

Shia LaBeouf
At age 18, Shia'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. "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."

 

Virgin Diaries

Jessica Simpson
At 22, Jessica Simpson gifted Nick Lachey with a little celebrity sex 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 two kids with her fiancé Eric Johnson.

 

Virgin Diaries

Nick Cannon
He married Mariah Carey, who is 11 years his senior. But did you know Nick has been into older women since he was a teenager? The America's Got Talent host lost his virginity at age 14 to an older gal. "We were in a sleeping bag … I