The Awkward Moments Celebrities Lost Their Virginities

While celebrities may seem perfectly polished and glamorous, they’re just like the rest of us, and they have had some pretty awkward moments too.

Here are a just a few celebrities with awkward stories of how they lost their virginity:

  1. Chris Evans: The day he lost his virginity, he ran home to his mom and yelled, “Mom, I just had sex! Where’s the clit?”
  2. Kholé Kardashian: She was only 14 years old when she dated an 18-year-old boy and got pressured into having sex. She told HLN, “”I felt like if I didn’t, I wouldn’t be cool or this guy wouldn’t want to talk to me anymore … I didn’t have sex for the next three years, just because I didn’t feel comfortable with my body and I didn’t feel like I knew myself. And then being out of that environment, I knew I did the wrong thing and I was kind of forced to have sex.”
  3. Angelina Jolie: At the age of 14, she was experimental and adventurous. She lost her virginity with her boyfriend at the time and “in a moment of wanting to feel closer…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.”
  4. Kim Kardashian: Also at the age of 14, Kim decided she wanted to start having sex with her boyfriend at the time. She told her mom in the bathroom that she was going to have sex and that she should be put on birth control. Her mom agreed.
  5. Shia LaBeouf: At 18, Shia lost his virginity but lied to the girl and told her he wasn’t a virgin. He played it off cool and told her not to worry but he admits he was shaking. “Getting naked was very strange,” he said, “It was the first time I’d been naked in 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.’
  6. Nick Cannon: When he was 14, he lost his virginity in a sleeping bag. When he asked her to change positions, she yelled, “just get off me!” and ran into a bathroom laughing about it with her friends. He admits that he cried at the end of his experience.
  7. Katy Perry: Her first time was in the front seat of a Volvo sedan. They were listening to the album “Grace” by Jeff Buckley when it happened.
  8. Ashton Kutcher: His first time was out in the woods at age 18. He was set up with a girl and the entire thing lasted two seconds. He met with her two years later and had sex with her again to show the girl he had gotten better.
  9. Lil Wayne: He was only 11 when he lost his virginity. She told him to get a board game from her walk-in closet and as she followed, she turn the lights off and took off his pants. Not knowing what was happening, he tried to push her away but he felt she was also naked, so he calmed down and let her take control.
  10. Jason Segel: He taught himself to play piano so that he could pick up girls. At 17 years old, he told a girl he wrote ‘Your Song,’ by Elton John for her and played it to set the mood before he lost his virginity to her that night.
  11. Jessica Simpson: She waited till her wedding night with Nick Lachey at 22 before she lost her virginity. She completely abstained from sex until she got married.
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