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Ah, celebrities: They’re just like us. At least when it comes to awkward first sexual encounters, which many—including Lena Dunham, Sienna Miller, Diddy, Jessica Alba, and Joe Jonas—haven’t been shy about sharing. Read on for tales of how 16 celebrities lost their virginity. Warning: Cringing might occur.
The “Girls” star lost her V-card at college, as she explained to Rookie in 2012. After a fight with her roommate, Dunham’s best friend Audrey headed to her room expecting a sleepover. “She was sobbing, and disoriented … so she flung my door open without knocking. There she found [the guy I was losing my virginity to] Jonah on top of me doing what grownups do. She understood the magnitude of the occasion and through her tears shouted, ‘Mazel tov!’
“I didn’t tell him I was a virgin, just that I hadn’t done it ‘that much.’ It hurt a little more than I’d expected but in a different way, and he was nervous too and he never came. Afterwards we lay there and talked, and I could tell he was a really nice person. I commended myself for making a healthy, albeit hasty, partner choice. I really couldn’t wait to tell my mom.”
Radcliffe—aka “Harry Potter—told Elle magazine in 2013 that his first time was actually—shocker—decent.
“I’m one of the few people who seem to have had a really good first time,” he said. “It was with somebody I’d gotten to know well. I’m happy to say I’ve had a lot better sex since then, but 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.”
In 2010, the reality star copped to losing her virginity at the age 14 in the Kardashian sisters‘ (pre-Kanye, obviously) tell-all, Kardashian Konfidential. “This guy was very, very manipulative, and I ended up losing my virginity to him when I was only 14,” Khloe wrote. “When my dad found out I was having sex, he went ballistic.”
KK also admitted to sneaking out to meet the mystery man, writing: “My mom taught me how to drive when I was 13, so if one of our baby sisters had an emergency I could drive to the hospital. But I took advantage of it. I used to steal her car or Bruce’s, and I’d go over to this guy’s house. He was a lot older than me, though he lied and said he was younger. Of course, I lied, too, and said I was 16. I was doing really well in school until I met him.”
The “Fault in Our Stars” actor admitted he 14 years old when he did the deed for the first time. “I was 14. I had no clue what I was doing, and neither did the girl,” he told Elle magazine in February 2015.
“I didn’t even make the lighting good. That’d be one thing I’d do differently. It was, like, fluorescent, bright bedroom light, like, over the covers.” When asked if he waited long to do it again, Elgort said “No, no, no. Definitely not. The only thing that made me feel better was doing it again.”
This one might blow your mind. While most of the free world would assume Britney lost her virginity to Justin Timberlake (despite vows of celibacy-until-marriage), Britney’s mom, Lynne, revealed in a memoir that the pop star lost her virginity to a high school football player at 14 years old
Sean ‘Diddy’ Combs
In 2010, Diddy revealed these gems to Playboy: “I tried to lose my virginity when I was seven years old. I was on top of a girl who was nine or 10, but it didn’t happen — so everybody doesn’t have to bug out. My mother and the babysitter whipped my ass, but it didn’t knock me off my mission. When I was 13, and I felt I was a porno star because I’d been watching porn for so long. 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 porn store at any given moment–it ain’t nothing I’m ashamed of.”
In predictable Angie fashion, her first time was, um, interesting.
“I had started having sex with my boyfriend at 14 and the sex and the emotions didn’t feel enough,” she told OK! (via Metro) “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.”
Hilton was 15 and allegedly lost it to fellow millionaire Randy Spelling, Tori’s brother, at a hotel in Palm Springs. “We were together for like two months … She was like 15; I was 17. We broke up like a week later,” Randy told the New York Daily News.
“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,” Kutcher told Details in 2008.
In a world where most celebs freely admit they lost their virginity at 14 and 15, it seems Fey held out until she was 24 because she “couldn’t give it away,” she told David Letterman. She ended up losing to Jeff Richmond, her now-husband.
The actress lost her virginity at 16 years old in her bedroom, because her mother insisted she experimented safely, in her own house.
“I had my first serious boyfriend when I was 16 and my mother made sure I brought him home,” she said. “She didn’t want me doing it outside and would say, ‘I’d rather you did it in my house if you’re going to do it at all … It was a very open household but I only brought home guys I really liked.”
“For some reason, I was trying to portray myself as a man who had [had sex] many times in the past,” the actor told Playboy (via Celebuzz) in 2009.
“I didn’t tell the girl I was a virgin. I was all, ‘Don’t worry, babe. I’m gonna handle it tonight.’ And meanwhile I was shaking in my boots. Getting naked was very strange. It was the first time I’d been naked in the 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. I’m not extremely well-endowed … and clearly this wasn’t the move.”
In 2005, Jess told Cosmopolitan: “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.”
In 2013, Jonas decided to come clean to New York Magazine’s Vulture, clearing up all those “purity ring” rumors. “I did other stuff before then, but I was sexually active at 20. I’m glad I waited for the right person, because you look back and you go, ‘That girl was batshit crazy. I’m glad I didn’t go there.”
We can’t say we’re shocked that the bad-boy actor lost his V-card the second he hit his teenage years. While promoting the Tim Burton musical “Sweeney Todd” in 2008, he told Rolling Stone: “I haven’t done anything this collaborative since I lost my virginity at 13.”
Okay, this one might be the most shocking. “I was 11 and the girl was 13, Weezy told Playboy in 2009 (via VH1). 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, ‘Fu+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.”
—Playboy [via VH1], April 2009
StyleCaster’s Second Annual Summer of Sex brings you scintillating content about—you guessed it—all things related to our favorite three-letter word. A few things to expect: Answers to pressing questions you always wanted to know but were too afraid to ask, ways to boost your own sex appeal, what being sexy means to various people, and lots and lots of eye candy. And that’s just the beginning.