Celebs Reveal How Awkwardly They Lost Their Virginity

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For most people, the first time you have sex is a nerve-wracking and awkward affair. You don’t know what you’re doing, you’re bearing yourself to somebody for the first time and there’s so much pressure. Famous people are no exception to this rule.

They were once awkward teenagers too you know! And judging by the stories on this list they had some terribly awkward and unromantic experiences when losing their V-card.

And reading about their difficult and sometimes tragic experiences is bound to make you feel less bad about your own horrible first time. It can happen to anyone, even famous celebrities.

1.Matthew Morrison

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This Glee star’s youth was as savoury as you would expect it to be. He didn’t lose his virginity until he was 21 because his high school girlfriend encouraged him to pray away any urges. Things were much different when Matthew Morrison began his musical theater career in the Big Apple however. According to Morrison, seeing as straight guys were such a rarity on Broadway, he was able to make it with a lot of hot dancers. He describes this period of his life as, “Very joyous and free.” The moral of the story is, it pays to be the only straight guy in a job that’s usually occupied by gay men and straight women.

2.Krysten Ritter 

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Krysten Ritter AKA The B in Apartment 23 lost her virginity to a real bad boy, as is the dream of most teenage girls. Ritter told Playboy that she and her bad boy beau started dating because he wrote her a dirty note on a high school picture. Well I guess he did charm the pants of her in the end because Ritter gave him her flower in his parents’ van before basketball practice. About her first time having sex she said, “I don’t remember it being very pleasant.” We’ve all been there!

3.Shia LaBeouf

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In an interview with Playboy, Shia LaBeouf spoke about his first experience of having sex at 18 as extremely nerve-wracking. He revealed that he didn’t let his mate know that he hadn’t done it yet and pretended to be much more experienced. Nevertheless, he was really nervous when it came to it, especially the getting naked part. He also told the interviewer that he placed a pillow under the girl’s back emulating an adult film he’d watched. This really didn’t work out well for him at all according to LaBeouf because he isn’t very well-endowed. It sounds like the actor had a similar experience to most people, a bit awkward and scary.

4.Daniel Radcliffe

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This one is going to ruin your childhood, because you really don’t want to know about the first time Harry Potter had sex – unless you enjoy reading dirty fan fics of course. Anyway, in an interview with Elle, Radcliffe described his experience as a positive one, “I’m one of the few people who seem to have had a really good first time … It was with somebody I’d gotten to know well.” Cue the speculation about which other Harry Potter star it could have been. He also went on to say, “It wasn’t as horrendously embarrassing as a lot of other people’s were — like my friend who got drunk and did it with a stranger under a bridge.” Was that Rupert Grint maybe?

5.Tina Fey

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Despite being an awesome and hilarious lady, Tina Fey lost her V-card quite late in life, at the age of 24. It’s hard to believe but the star stated that she “couldn’t give it away” in an interview with David Letterman. According to Fey, she didn’t really have the option of having sex at a younger age like a Victoria’s Secret model might (because they’d have guys falling at their feet obviously). When she eventually did the deed it was with her now husband Jeff Richmond. I guess that means he’s the only person she’s ever slept with. It’s pretty romantic don’t you think?

6.Kim Kardashian

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Kim Kardashian lost her virginity at just 14 years-old, a fact which she revealed on The Oprah Winfrey Show. I couldn’t imagine telling Oprah about my first time, it would be like telling my mom. But it turns out that’s what Kim K did anyway, when she was in love with her boyfriend and wanted to have sex she went straight to her mom, Kris Kardashian, to discuss it with her. Kim very wisely wanted to go on birth control and Kris obviously encouraged the fact. Well, I guess they are a very open family so it’s not too surprising.

7.Ashton Kutcher

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Like most guys before their first time, prankster Ashton Kutcher really felt the pressure. He was only 15 when he lost his virginity and it was out in a forest, with a girl he’d only just met. He admitted in a magazine interview that, “The whole thing lasted two seconds.” Poor guy. But he went on to say that he slept with the same girl a couple of years later to prove that he had gotten better since then. The male ego makes guys do some silly things.

8.Lena Dunham

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Of course Lena Dunham was happy to write a segment on sleeping with somebody for the first time. In the segment for Rookie Mag, she talks about how she lost her virginity when she was a college sophomore. Of course the circumstances were pretty comical too. Her friend Audrey busted into the room during Dunham’s first time. According to Dunham, “She understood the magnitude of the occasion and through her tears shouted, ‘Mazel tov!’” Despite this she was happy with her first time overall because it was with a nice guy and she’d made “a healthy, albeit hasty, partner choice.”

9.P. Diddy

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You’d expect a rap star to brag about losing their V-card but P Diddy takes it to a whole other level. The rapper claims that he first tried to lose his virginity at 7! But he didn’t succeed and lost it later, at the age of 13, while he was still very young. He’s spoken about how things were back in the day. You were able to get a cheap hotel room for an hour in the Bronx, and so he carried around a little bit of cash in case the occasion arose. On losing his virginity Diddy said, “I felt I was a p*rn* star because I’d been watching p*rn for so long.” It’s pretty crazy.

10.Celine Dion

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It’s clear to see that Celine Dion is a true diva, as her experience of having sex for the first time was so dramatic. Or at least it sounds dramatic the way that she tells it in her autobiography My Story, My Dream. She begins, “It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition.” So Dion was de-flowered on the same night she won the Eurovision song contest. She was a double winner that night. Her first experience was with her manager/husband whom she told, “You’ll be the first. And the only.”

11.Nick Cannon

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Cannon is 11 years younger than his former-wife Mariah Carey. Turns out his penchant for older women isn’t something new. He lost his virginity to a high school student when he was still in junior high. He’s spoken out about how it was quite an ordeal for him. They did it in a sleeping bag and when he asked the girl if she wanted to change positions she said, “Just get off me!” The girl then went and laughed in the bathroom with her girlfriends. Cannon revealed that he cried afterwards and vowed that nobody would ever laugh at him in the bedroom again.

12.Matthew Fox

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The dreamboat actor was a very early starter when it comes to sex. His first time was with a girl two years older than him when he was just 12. It was by a riverbank in his small hometown while there was some sort of rodeo going on apparently. He describes the experience as terribly unromantic, “It was absolutely terrible and awkward—just two kids lying down and pulling our pants down.” Not to worry though I’m sure many women have thrown themselves at him over the years and he’s had lots of better experiences since then.

13.Megan Fox

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We all know that the actress oozes sex appeal! She’s happy to talk openly about sex too, although she hasn’t given away too many details about her first time. She talked about her first time doing the deed in an interview with Cosmopolitan and it seems like it was quite a pleasant affair. She didn’t spill any steamy details though. Megan Fox lost her V to an unnamed actor who was her first real boyfriend at 17 years-old. About the experience she said, “I’ve had plenty of awkward sex, but that first time was not awkward. I was in love with him, and it was nice.” It’s hard to imagine Megan Fox just having “nice” sex.

14.Russell Brand

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Comedian Russell Brand shared his first time in his autobiography My Booky Wook. And it sounds absolutely wild. According to the star it took place on a holiday in Asia after visiting a dive bar with his dad. Brand’s dad brought three paid ladies back to the hotel, two for himself and for one for his son. It sounds like they did it in the same room which is pretty gross. Brand described it as a “bungling encounter” because it was his first time. That’s an example of top parenting for you right there.

15.Johnny Depp

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The handsome Mr Depp lost his V-card in the backseat of a car at just 13 years-old. He was in a band at the time called The Flames and his first experience was with one of the band’s ‘groupies’. It’s hard to imagine that a band with such young members would have groupies. But anyway, the actor has spoken about how much of a wild child he was in interviews. Depp says, “I lost my virginity somewhere around age 13.