11 Famous Celebs Who Lost Their Virginity In A Shocking Way

#1 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."

#2 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 reveals to GQ that she fooled around "in the front seat of a Volvo sedan while listening to Jeff Buckley's album Grace."

#3 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 tells New York Daily News. "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."

#4 Johnny Depp

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

#5 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," explains Segel.

#6 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," Khloe said. "Don't let anyone pressure you, it's not worth it and how I felt afterward."

#7 Fergie

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

#8 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.

#9 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."

#10 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.

#11 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.