Not everybody wants to share the story of their first time, but given Kendra Wilkinson's infamous sex tape, it shouldn't be surprising that she wrote all about losing her virginity at 13 in her memoir, Sliding Into Home. "We had no idea what we were doing," she described of her first time, but that was not the case when she went to sleep with Playboy's head honcho Hugh Hefner. "One of the girls asked me if I wanted to go upstairs to Hef's room… It seemed like every other girl was going, and if I didn't it would be weird," the reality-TV star and new mom recalls in her autobiography. "One by one, each girl hopped on Hef and had sex with him… for about a minute. I studied their every move. Then it was my turn… it was very weird. I wasn't thinking about how much older Hef was—all the body parts worked the same. I wanted to be there." Sure, it wasn't her first, but it was her first time with a man in his eighties who's done it many times—and that counts for something.
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First times can be emotional—and Mr. Mariah Carey, Nick Cannon, learned that lesson early. The actor admitted to on Lopez Tonight that he lost his virginity to "an older lady" when he was younger and " ended up crying at the end of the whole ordeal." "She was in high school and I was in junior high," Cannon explained, of girl who took his virginity. "We were in a sleeping bag. I said we should change positions. She was like, 'Just get off me!' She ran into the bathroom with all of her friends and they were in there laughing. I vowed from that day forward no woman would ever laugh at me in the sack again, and that's when the 'Cannon' was born!" Though we'd like to think some things have changed and there are no more tears following sex with Carey, his tendency to bed older women (the singer is 11 years his senior) has not.
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In a book called Where Do Nudists Keep Their Hankies?, author Mitchell Symons reveals many celebrities who had sex at a young age, but one of the biggest surprises? Sean Connery said he lost virginity at the age of 8. (Take that, Diddy.) The now-79-year-old actor said he doesn't "remember with whom," although to be fair, who really remembers things very clearly from when they were 8 years old? But one thing's for sure—he was obviously meant to play the smooth-talking, heart-breaking James Bond in the years to come.
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Harry Potter star Daniel Radcliffe thought it a magical moment in 2004 when he met the Irish-born Amy Byrne, a 23-year-old hair stylist, during the filming of the franchise's fourth installment Harry Potter and the Goblet of Fire. "I'd say it's a pretty big a deal being 16 in England," he told The Mirror at the time. " You can have sex and play the lottery. And I couldn't wait to play the lottery!" Seems like he couldn't wait to have sex either. A few years later, the beloved bespectacled actor told Details that he lost his virginity at 16 to "a much older woman," who Us Magazine later claimed was Byrne, six years his senior. A coy Radcliffe claimed, the age difference "wasn't ridiculous… but it would freak some people out."
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Diddy admitted he lives the "American rap star dream" in Playboy, but he wasn't completely successful the first time he attempted to have sex. At the age of 7 (yes, 7), the rapper/producer said he climbed on top of a girl he estimated to be around 9 or 10 (an older woman), but "it didn't happen," he admitted, despite his earnest efforts. "My mother and the babysitter whipped my ass, but it didn't knock me off my mission," he told the magazine. He "finally" lost his virginity at 13, and said he "felt like a porno star because I'd been watching porn for so long." His second attempt—and those thereafter—were seemingly positive. Diddy said he is "proud to admit I love having sex. You might catch me in a porn store at any given moment—it ain't nothing I'm ashamed of."
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Sienna Miller has had some famous sexual escapades since stepping into the spotlight, but her first time looks pretty normal at first glance: She said that she lost her virginity at 16, at home, in a bed. The story, however, does get a little strange from there: She told The Sun that her mother "made sure I brought him home. She didn't want me doing it somewhere else and would say, 'I'd rather you did it in my house if you're going to do it at all.'" Amy Poehler's character had similar advice for Lindsay Lohan's in Mean Girls regarding alcohol, telling her, "Do you want a little bit? Because if you're going to drink, I'd rather you do it in the house." And look where she wound up.
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After rumors surfaced this year that the Lost star had cheated on his wife with a stripper, Matthew Fox gave an interview with Playboy magazine in which he denied the affair and described his first time at the mere age of 12. Fox said "it wasn't her first time" and his unnamed lover was about two years older than him. He admitted the whole experience was "terrible and awkward." Perhaps contributing to the awkwardness? They were outside, "literally on the ground while a rodeo was going on in town … just two f------ kids lying down and pulling our pants down." Let's just call it practice for sex Oceanic Six style on the island, shall we?
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Lil' Wayne liked board games as a kid so it makes sense then that when visiting a 13-year-old girl, who "had every board game you could imagine," the then-11-year-old rapper decided she was the one with whom he wanted to have sex for the first time. "We was playing Win, Lose, or Draw and on the board she wrote, "F--- me,'" he told Playboy. The next thing he knew, he was naked and in a dark walk-in closet. At first hesitant, Lil' Wayne eventually gave in to the moment. "I felt that she was naked also, so I just stepped back and let her do what she do," he said of the innocence-lost moment.
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Red Hot Chili Peppers frontman Anthony Kiedis proved he earned his rock 'n' roll stripes with the tale of how he lost his virginity in his memoir Scar Tissue. The rock star wrote that his father arranged for the then-13-year-old Kiedis to lose his virginity to his father's 18-year-old girlfriend, while his father watched. Rounding out the father of the year award, Kiedis' father also supervised his son's first coke injection that same year. Not even Jon Gosselin nor Michael Lohan could compare.
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Katy Perry recently told Esquire UK that the British comedian and actor, to whom she is betrothed, "used to basically be a professional prostitute" But actually, the first time he rolled around in the sheets, Russell Brand was not the one getting paid. He revealed in his autobiography My Booky Wook: A Memoir of Sex, Drugs, and Stand-Up that he lost his virginity to a prostitute in Hong Kong, paid for by his father. "The episode that defined my relationship with women occurred in Hong Kong with my dad. I was 17," he recounted of the experience. "On day one, we went to some sleazy dive. Before long I was sat on a bar stool with a Filipino called Mary-Lou. Then we were leaving in a cab with three Asian prostitutes my dad was drunkenly herding. Back in the hotel my dad set about unwrapping his two prostitutes. I sat on the edge of the other twin bed. She must have known I was a virgin as soon as the bungling encounter commenced." But from that point on, he was hooked to the extent that he was later treated for sex addition.
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For someone so fixated on time (thanks to the giant clock around his neck), it's really no surprise Public Enemy's Flava Flav wasn't waiting around to have sex. At 6 years old, the hype man lost his virginity outdoors atop a box. And no, that's not a double entendre. "A girl and me were having sex on a box in some big tall bushes," Flav told Complex. The VH1 reality-TV staple admitted he was "real, real, real, real young." Translation: 6 years old. "We learned to have done the nasty back in the days, and me and this girl we experiment, we were experimenting, and my little joint got hard," he said. "I penetrated for about a few seconds," which is probably an accurate evaluation of the duration.
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Though Johnny Depp has long been somewhat of a Hollywood rebel, it seems he was more conciliatory when he lost his virginity. The actor told Rolling Stone in 2008 that while making the movie Sweeney Tood that he hadn't "done anything this collaborative since I lost my virginity at 13." While it's not exactly clear what that means, young Depp seemingly received high marks in junior high for playing well with others.
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Unlike Russell Brand, Aerosmith frontman Steven Tyler is actually a rock star and not just playing one on the silver screen. But the two do have something in common—at the tender age of 15, a prostitute took his V-card. And if that's not bad enough, he had to wait until three of his friends had finished with her before he got a turn. "It was such a nasty experience," he recalled of the incident. "I had to wash my penis in the sink." The rock 'n' roll hall of famer does not have the fondest memories of his filthy first time—as for the lady of the night's looks? "She was not a good-looking woman," Tyler added. Ouch.
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Happy Days heartthrob Scott Baio wrote a tell-all memoir called BaioWatch: How I Dated and Loved Hollywood's Most Beautiful Women and Ended Up Alone, which Radar got the first 60 pages of in 2007. In the autobiography's climax, if you will, Baio revealed that at 16, he lost his virginity to co-star Erin "Joanie" Moran—but not without a little trouble. "I didn't know what to do," he wrote. "I didn't know what to say after we got naked. So for the first five minutes, maybe less—hell, it might have been the first 20 seconds—I'm doing it and thinking, man, this is really uncomfortable. What happened was, my thing was between the cushions on the couch and I didn't even know it. Instead of being inside Erin, I was humping a corduroy sofa!" More than four decades later, Baio's legendary love for Joanie landed him a spot in DJ Lubel's music video " Wrong Hole." Now Scott Baio is 48, married, and hopefully staying away from couch cushions.
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