How did you lose yours? See how these 10 celebrities lost their virginity

Posted on May 19 2017 , at 06:55 pm
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  • Their experiences go from painful to romantic, and downright extreme.

Some of Hollywood’s big names have told us how they lost their virginity.

How did you lose your virginity? It might have been awkward, painful, or funny – just not exactly the romantic, beautiful moment you were hoping it’d be.

While celebrities are living seemingly perfect lives, when it comes to losing their virginity, they’re just like us.

Check out their stories.


Angelina Jolie

Angelina Jolie

‘I had started having sex with my boyfriend and the sex and the emotions didn’t feel enough. I was no longer a little girl. 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.’Metro UK!, April 2007


READ: ‘It was very difficult’ – Tearful Angelina Jolie finally speaks on Brad Pitt divorce



Khloé Kardashian

Khloé Kardashian

‘My situation was not a good situation. I was 14 years old and dating an 18-year-old boy, which now I look back and think it’s disgusting, but then I thought I was really cool … Basically, I got pressured into having sex. I wasn’t ready. I barely knew my own body…


READ: French Montana’s still my friend, he’s seen my vagina – Khloe


‘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.’HLN, December 2012



Megan Fox

Megan Fox

‘I’ve had plenty of sex, but that first time was not that awkward.


I was in love with him and it was nice.’Cosmopolitan 2010.



Krysten Ritter

Krysten Ritter

‘He was a real bad boy. He gave me a school picture that year that said, ‘OK, Krysten, I love you. You give me a boner.’ That’s how we started dating. His name was Damian, but my parents called him ‘Demon.’


‘Our first time was in his parents’ van before basketball practice. I don’t remember it being very pleasant.’Playboy, October 2012



Chris Evans

Chris Evans (Captain America)

‘The first time I had sex I raced home and was like ‘Mom, I just had sex. Where’s the clit?’ – Cosmopolitan



Celine Dion

Celine Dion

‘It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition. He went back to my room with me … I was seated at the head of the bed, legs folded under the covers.


‘I was happy about being alone with the man I loved. And I had a very precise plan.’ – Dion’s autobiography My Story, My Dream, October 2012



Lil Wayne

Lil Wayne with ex girlfriend, Christina Milian

‘I was 11 and the girl was 13. She had every board game you could imagine. I liked board games. We was playing Win Lose or Draw and on the board she wrote, ‘Fuck me.’


‘Now I was 11, and I didn’t even know it meant ‘intercourse.’ I just knew it was a cuss word, so I was like, ‘Why is she cussing herself out?’


READ: How Lil Wayne and Christina Milian broke up after one year of dating


‘She said, ‘Do you want to play Press Your Luck? Well, the game is in my closet.’ She had a walk-in closet, so she said, ‘Go get it, it’s right to the right…’


‘When I walk to the closet she came in and cut the lights off and took off my pants, and I remember my ass was cold up against the wall. I was like, ‘What the hell!?’ When I tried to push her off me, I felt that she was naked also, so I just stepped back and let her do what she do.’Playboy, April 2009



Sarah Silverman

Sarah Silverman

‘He led me to his bedroom — a bed, a dresser, and an ashtray. He kissed me while he laid me back in his bed.


‘Have you ever had sex before?’


‘’Yes, I’ve had sex before,’ I said, insulted.


‘He put on a condom and pushed against me, but there was honestly no hole there. I figured that was it. The guy just pokes hard between your legs for a while. Sex. When he finally gave up, he said, ‘It’s not like it is in the movies, Sarah. Is that what you thought?’ – Rookie, March 2012



Jessica Alba

Jessica Alba

‘I didn’t really [seriously] go out with any guys until I was 18 and met my ex-fiancé, Michael Weatherly … It just didn’t work out. I was so young, 18, when I started dating him.


‘I was a virgin. I knew I wanted to be in love with the first person I slept with, because for almost everyone I knew, the first experience made them feel like shit.


‘So I wanted to be really careful that he was going to be in love with me and wasn’t just going to leave me.’Cosmopolitan, October 2005





‘I was 14. I mean, in upstate New York there’s really nothing to do up there but experiment. He was a senior, and I thought he liked me but turned out he was just a jerk. So, it was terrible.’ — YourTango, April 2013

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