Stars are often known to be particularly outspoken, so of course, we’re able to get all the saucy details and get them to divulge in shocking detail about their first time. These A-List stars are known to have lost their V-Card at an early age, and some were even as young as kids. You’ll be surprised to discover some of our favorite celebs weren’t shy in revealing intimate details about losing their virginity and that even for seemingly perfect people, it’s not always a perfect moment.
Among these young stars who stated they lost their virginity young is Kim Kardashian West who was aged 14 at the time. Her partner in the sack was none other than Michael Jackson’s nephew, TJ. Following suit at just 14 years old was Tomb Raider’s own Angelina Jolie, and Lost star Matthew Fox lost his at 12. Several famous male stars and musos also revealed they had sex at a young age including the likes of singer Chris Brown who lost his virginity before he had even turned 10!
We’ve rounded up some of the most interesting and shocking stories from the actress who may or may not have waited for her husband, to the actor who lost his V-Card after being a member of a band to a daring game of “Win, Lose or Draw.”
The following are 15 chilling stories featuring a string of stars that lost their V-Card at a very, very young age. Read on for all of the surprising details…
15. Jaime Pressly – 14
For model-turned-actress Jaime Pressly, her first experience was anything but romantic, and she was more than happy to overshare about losing her virginity and all the dodgy details in a sit-down interview with Howard Stern.
Everyone knows that when confessions go down on the Howard Stern show, it’s all very raw and unedited, and this interview was no exception. We almost feel for poor Jamie that her first time was so awful! She went on to say that she was “too tight” during her first experience and that her partner “never finished” as a result.
14. Kim Kardashian West – 14
Just when you think there’s absolutely nothing else left to discover about Kim Kardashian West, we have news for you. In the days long before Ray J, Reggie, and even current hubby Kanye West were on the scene, there was another great love in Kim’s life. This man is celeb royalty and is someone that’s even related to one of the most famous musicians to ever have existed.
Kim Kardashian West lost her V-Card at the young age of 14 to TJ Jackson, none other than Michael Jackson’s nephew. Kim went on to explain how she approached her mum back in the day before her — shall we say, “big day” — which she recalled in a conversation live on the Oprah Show in 2012.
13. Angelina Jolie – 14
Angelina Jolie is one of Hollywood’s most in-demand actresses, so it’s not at all surprising that the world has always remained curious about her personal life. She has a soaring career and admirable advocacies, but somehow, her love life hasn’t turned out perfectly as we once thought it would.
The gorgeous brunette beauty lost her virginity at 14 years old.
“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. 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,” said Angelina in an interview with OK magazine in 2007. “I was a member of a group called the Kissy Girls. I was very sexual in kindergarten. I created a game where I would kiss the boys and give them cooties. Then we would make out, and we would take our clothes off. I got in a lot of trouble!”
12. Britney Spears – 14
If you’re anything like us, then you were probably thinking this story is about the great love affair of Britney Spears and Justin Timberlake, right? Wrong! The child star turned songstress lost her virginity to a football player at her high school when she was just 14 years old. How do we know this? Her mom, Lynne Spears, revealed all. Awks.
The Toxic singer’s former momager detailed her daughter’s first time in a revealing memoir Through the Storm: A Real Tale of Fame and Family in a Tabloid World. If that was a case of TMI, then you’d be surprised to hear Brit’s mom didn’t stop there. She also went on to reveal Britney Spears started drinking at the age of 13 and lost her V-Card to a football player that was 18, all the while with her mom encouraging her. She hoped it would make her daughter more popular, and it looks like it worked.
11. Khloé Kardashian – 14
On the set of The View in 2010, the Strong Looks Better Naked author and star of Keeping Up with the Kardashians revealed details about her first time. Khloé revealed that she almost felt “conned” by her older sex partner. “Looking back, I think that’s not a normal thing,” she said.
Then in her book, Kardashian Konfidential, Khloe admitted to losing her virginity at 14. “It’s not funny to lose your virginity! It’s weird, and you’re scared, and it hurts, and you don’t know what will happen. I was 14, and he was an older guy who wasn’t a virgin.”
“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.”
10. Snooki – 14
For Snooki, former Jersey Shore star, her first sexual encounter was “terrible” and took place when she was just 14 years old. It just goes to show that not everyone’s first time is something to look back on with pride.
The reality star and now proud mom confessed all to YourTango magazine and said it was nothing less than terrible. She and the guy were young, and they didn’t have a condom, so they used saran wrap instead. “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.”
9. Ashton Kutcher – 15
Even the sexiest of celebs have awkward first-time stories, and actor Ashton Kutcher is no exception to the rule. He revealed all to Frisky magazine in a tell-all interview back in 2008. Long before he was married to the ever-gorgeous Mila Kunis, the actor had a horrible first-time experience.
“I was 15. It was out in the woods with a girl I had just met who my buddy set me up with. The whole thing lasted two seconds. It was really awkward. Two years later, I had sex with her again just to show her the first performance was a fluke and I’d gotten better.”
8. Matthew McConaughey – 15
Oscar-winning actor Matthew McConaughey has always been hot and has always had a way with the ladies. It could be the reason behind Matthew giving it all away at the tender age of 15. But don’t you dare think he’ll be happy to reveal more details than that.
The actor once confessed to Playboy Magazine about losing his V-Card when he was just 15 years old, but he refused to divulge any further details. He told the magazine in no uncertain terms, “I don’t tell bedroom tales. Never have.” When the publication urged him for further saucy details and to divulge more, it’s rumored that Matthew, husband to Brazilian-American model Camila Alves and father to three kids politely declined. “None of your business, I don’t kiss and tell.” To this day the identity of the girl is not publicly known…
7. Paris Hilton – 15
At just 15 years old, the first sexual encounter took place for the Hilton heiress, and it seemed nothing went to plan. Randy Spelling went on to tell the New York Daily News, “We were together for like two months. 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,” explained her fling, Randy Spelling. “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.”
6. Robin Thicke – 13
In another Howard Stern exclusive, Robin Thicke detailed his first-time sexual encounter. The Blurred Lines star was just 13 at the time, and when a reporter asked what he wished he could change about losing his virginity at such a young age, Robin candidly responded, “Make it last longer than 30 seconds.”
Robin Thicke is well known for being outspoken about his sexual adventures and his deepest darkest desires. Perhaps, it shouldn’t shock us then that he lost his V-Card so young. Perhaps he should stick to doing the deed and less to talking about it so he can get those feminist groups off his back.
5. Johnny Depp – 13
The first time we heard about legendary actor Johnny Depp’s first time was in his passing comment to Rolling Stone magazine. The Sweeney Todd star was promoting the 2008 musical and proclaimed, “I haven’t done anything this collaborative since I lost my virginity at 13.”
We all knew Johnny Depp was a rebel, but perhaps we could never have seen this coming. Then again, during those days, Johnny was a child star and had already begun drinking and smoking and even doing drugs at the age of 12.
4. Matthew Fox – 12
Smoking hot Lost star Matthew Fox had little to say about his first time, but chilling details revealed he was just 12 years old at the time, practically a kid. He agreed to an exclusive interview with Playboy magazine and said the whole experience was “absolutely terrible and awkward.”
The exclusive caused quite the stir, and rightly so. Fancy finding out all the chilling details? Well, it appears that the young star grew up in the small town of Dubois in Wyoming, and that’s how things were done in those days. He wouldn’t reveal too much about his partner other than that she was a couple years older and was more experienced. The first encounter took place by a river while a rodeo was in town. Fox revealed it was the classic “pull your pants down and mess around” scenario.
3. Lil Wayne – 11
Well, what can we say when it comes to Lil Wayne other than he continues to shock the hell out of people with what he has to say. This time, it’s his chilling confession about losing his virginity at just 11 years old.
The rapper was not shy in dishing the dirt about his racy first time and said that it all went down during a game of “Win, Lose or Draw” with a 13-year-old girl. Lil Wayne claims the girl he was playing with wrote down “F—k me” on the board, and the rest, as they say, is history as he revealed all in an interview with Playboy magazine.
“I was 11, and the girl was 13. She had every board game you could imagine. I liked board games. We were playing Win, Lose or Draw and on the board, she wrote, ‘F–k 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?'”
“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.'”
2. Sean “Diddy” Combs – 13
Sean Combs aka P Diddy, once told Playboy Magazine that he had been trying to lose his V-Card since the ripe old age of 7, and from what we hear, he almost succeeded.
The first time P Diddy got sexual was when he was just a child, and he revealed in a tell-all interview that he tried “by getting on top of a girl who was about nine or ten years old.” The experience didn’t go as planned, fortunately, and he went on to say that his mother and babysitter thoroughly punished him for trying. If you thought that stopped the young rapper from trying again, you’d be wrong, as sooner or later he succeeded.
He eventually lost his V-Card at age 13 and wouldn’t reveal who the mystery girl was that helped him seal the deal. “In the Bronx, you could get a hotel 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 p–n store at any given moment — it ain’t nothing I’m ashamed of.” TMI, P Diddy. TMI.
1. Chris Brown – 8
Chris Brown has his cousins to thanks for his sexual prowess, which he began developing at a shockingly early age. It’s been said he was subjected to sexual imagery at a young age when they would all watch p–n together.
We’re assuming that would make any 8-year-old curious, and lo and behold, soon, Chris lost his virginity to a girl who was rumored to be 15 years old. “At eight, being able to do it, it kind of preps you for the long run, so you can be a beast at it,” he said. “You can be the best at it,” said Chris to the readers of The Guardian.