27 Celebrities Share The Awkward Ways They Lost Their Virginity

Some celebrities make a career out of talking about their virginity: Britney Spears claimed to be a virgin in her teenage prime, Jessica Simpson famously spoke about not having sex until her wedding night, and now Nick Jonas is boasting about his bedroom exploits years after rocking purity rings publicly. For some stars, it's a matter of marketing and borderline fetishization, for others, like Jonas, it's the latest step in TMI marketing and pandering to an aging audience.

Having sex for the first time is a big deal to some people, not such a big deal to others, and stars are no different. Some celebrities have normal, awkward experiences like anyone else, while others have had uncomfortable, creepy and even traumatic times losing their virginity.

When you read these celebrity first time sex stories, chances are they'll shed some light on how they approached the rest of their love lives ... at least in the public sphere.

1. Nick Jonas

Nick Jonas recently confessed to Wendy Williams that he lost his purity ring and his virginity, though he didn't provide details on when. "I'm an adult in all ways," the perpetually smug singer said. Right, because when you're a Disney kid, the only way to assert your adulthood is to make your entire persona about sex.

Photo: Flaunt Magazine

2. Joe Jonas

Joe Jonas wrote a long missive in New York magazine about his sexual exploits and purity ring pressures. "The topic that dominated news coverage of us for a long time was the whole promise-ring thing. We couldn't escape it. It started when I was really young — I must have been 10 or 11. There's a program people do in some churches called True Love Waits, where you wait for marriage to have sex. Kevin and I decided to join — Nick tried it later. Fast-forward a few years, we've started playing music and we're working with Disney and we have these rings." He added, "I lost my virginity when I was 20. 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 bats--t crazy. I'm glad I didn't go there.'" (Fact: Joe Jonas was dating Ashley Greene when he was 20.)

Photo: IMDB

3. Anthony Kiedis

Anthony Kiedis famously lost his virginity when he was 12 ... to his own father's girlfriend.

Photo: VEVO

4-5. Tia Mowry-Hardict And Tamera Mowry-Housley

Tia Mowry made her man, Cory Hardict, wait a year to kiss (and do other things). She told OK! magazine, "I think the one thing I did do was I just held out. We weren’t physical, we didn't do anything for a while to make sure this was something special and this was something real. That's what we did. And also my husband … we courted each other for about a year. We didn't go on dates with just him and I, there were other people around. We waited a year to kiss. That's basically what I did." Tamera Mowry lost her virginity to her husband, Adam Housley, at 29 years old. "I don't know how to explain this, but I'm religious ... So I waited 'til I was 29 to lose my virginity," she dished to Hot 97. "And then — you may not understand this — I did it and then I felt guilty, and then I became celibate until I got married."

Photo: IMDB

6. Bethenny Frankel

On her eponymous, now-cancelled talk show, Bethenny Frankel spoke about losing her virginity on Valentine's Day at age 16.

Photo: IMDB

7. Sean "Diddy" Combs

Sean "Diddy" Combs (or whatever else he's calling himself lately) got interested in sex at an extremely young age. In an interview, Combs said, "I tried to lose my virginity when I was seven years old. I was on top of a girl who was 9 or 10, but it didn't happen — so everybody doesn't have to bug out! [I lost it] when I was 13, and I felt I was a porno star because I'd been watching porn for so long." He added, "In the Bronx, you could get a hotel [room] 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." Nor should you be ashamed to love sex. But, uh, that's still some TMI, Diddy.

Photo: IMDB

8. Will Ferrell

Will Ferrell lost his virginity in his junior year of college. "In my mind's eye, it seemed like the way it was supposed to happen," he said. But his mom, on the other hand, thought his first time having sex was much earlier with another girl in high school. "She said, 'If you slept with this girl, you'd better slap a condom on that pecker of yours.'"

Photo: IMDB

9. Matthew Morrison

Matthew Morrison admitted he didn't lose his virginity until he was 21 because his hyper-religious high school sweetheart would have them stop to pray whenever things got too amorous. He reminisced, "It was sweet. It was innocent." Then once he got that out of the way, Morrison went all in on Broadway, where he was one of the few straight dudes among entire casts of gorgeous women. "There was so much opportunity. There were all these beautiful, beautiful dancers. As a straight guy, I had some room. There were the shared interests in singing and dancing, and I always find dancing with someone very evocative and sexual. I definitely hooked up with a lot of girls when I was a young guy on Broadway. It was exciting. Very joyous and free." Anyone else think he may be protesting too much?

Photo: IMDB

10. Daniel Radcliffe

Talk about horny: Daniel Radcliffe lost his virginity on his 16th birthday to his then-girlfriend, who was older.

Photo: IMDB

11. Kelly Osbourne

Kelly Osbourne cashed in her V-card at 13 years old, and she, like Kim Kardashian, was responsible about it, to the point of paranoia. "I convinced myself I was pregnant," Osbourne admitted. "I hadn't even gotten my period [yet]." Phew. That's good news for all of us, because, well, how many of us want a nepotist who makes a living talking smack about people's appearances to breed? Anyone?

Photo: IMDB

12. Snooki

Snooki confessed to MTV that her first time having sex was, uh, really dumb. "We were so young, and I didn't want to get pregnant, so he literally put Saran Wrap on his penis and we tried to have sex. It was stupid ... Looking back at it now, I wish I had saved my virginity for Jionni, because I’m obsessed with him."

Photo: Instagram

13. Tina Fey

Tina Fey lost her virginity at 24 to Jeff Richmond — her husband! "I just couldn't give it away," the 30 Rock star admitted. "I remember bringing people over in high school to play—that's how cool I am—that game 'Celebrity.' That's how I successfully remained a virgin well into my 20s, bringing gay boys over to play Celebrity."

Photo: IMDB

14. Steven Tyler

Steven Tyler told Elle magazine that his first sexual experience was with twins ... when he was seven years old.

Photo: IMDB

15. Ashton Kutcher

Even Ashton Kutcher's first time sex story is obnoxious. "It was out in the woods and it was horrible," the That 70s Show star said. "It was a girl I'd just met who my buddy set me up with. The whole thing lasted like two seconds. It was really awkward. Two years later, I had sex with her again just to show her that the first performance was a fluke and I'd gotten much better."

Photo: IMDB

16. Nick Cannon

Nick Cannon's first time having sex was unintentionally hilarious, just like most of his attempts at intentional humor. "We were in a sleeping bag … I said we should change positions, she was like 'Just get off me!'" Cannon said in an interview. "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. I actually ended up crying at the end of the whole ordeal." Just like the world did at this photo, and just like he probably is now over Mariah Carey, who reportedly was disgusted at his constant TMI about their sex life.

Photo: Instagram

17. Shia LaBeouf

When Shia LaBeouf lost his virginity, he used his acting chops to try to make his partner think it wasn't his first time having sex. "I was trying to portray myself as a man who had done it many times in the past. 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," he admitted. "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." Chances are his cover was blown well before his confession went to print.

Photo: IMDB

18. Matthew Fox

Matthew Fox remembers his first time having sex like it was yesterday. "I was 12. She was about two years older than me. It wasn't her first time. I can actually see the event in my mind's eye, like photographs," the Lost star says of losing his virginity. "It was in Dubois, Wyoming, where the population sign probably says, to this day, about 1,000. It happened, literally, on the ground by a river while a rodeo was going on in town … it was absolutely terrible and awkward — just two kids lying down and pulling our pants down."

Photo: IMDB

19. Mama June Shannon

Maybe the reason Mama June is into dating sex offenders and pedophiles is because, well, that's what she's used to. She told Entertainment Tonight that she lost her virginity at 12 years old and that she had no idea what was even really happening the first time she had sex. "I had no idea what it was, how to whatever … and then it kind of escalated from there ... I was dating men who were in their 20s, 30s, my mom knew about it. I would kind of lie and say they were 21, 22. When me and Mark [McDaniel] started dating, I was 20 and he was 38. There was an 18-year age difference." Mama June gave birth to her oldest daughter, Anna "Chickadee" Cardwell when she was only 14 years old. Cardwell later accused Mark McDaniel of molesting her, an allegation Mama June has firmly and fiercely denied.

Photo: IMDB

20. Khloe Kardashian

Khloe Kardashian admits that losing her virginity was nearly traumatic. The youngest and tallest Kardashian sister actually regretted her first time having sex. "I should have listened to my parents," she lamented. "Don't let anyone pressure you. It's not worth it and how I felt afterward."

Photo: YouTube

21. Jessica Simpson

Jessica Simpson famously lost her virginity to then-husband Nick Lachey on their wedding night. He classily later referred to her as "the best stocking I ever stuffed," while ex-boyfriend John Mayer called her "sexual napalm." We're glad she's moved on to better (and probably bigger) things.

Photo: IMDB

22. Angelina Jolie

Of course Angelina Jolie didn't have a totally vanilla sex life, even as a teen. The Oscar winning (and soon to be retired) actress once confessed, "I had started having sex with my boyfriend at 14 and the sex and the emotions didn't feel enough. 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 ... It was an age when I felt adventurous and after a few beers, things happened." Hold up, Ange. Beers? At 14? Scandalous!

Photo: IMDB

23. Brooke Shields

Brooke Shields calls herself "the most celebrated virgin of all time" in her memoir, There Was A Little Girl, and she previously wrote a chapter about her virginity in her teen memoir, The Brooke Book. "The whole virginity thing happened quite genuinely," she says. "I had no problem talking about it because I talked about it with my friends. My mother thought it was important for me to then represent that to kids. I was just honest, and like, 'By the way, I also didn't smoke and I had braces.' These things were not off limits with regard to the public and their knowledge of me so I thought, 'Okay, that'll be a good chapter.'" As for when Shields lost her virginity, it was in college — to a man who'd later be Superman. Shields says she and Dean Cain met at Princeton University and were "instantly crazy about one another ... always holding hands and trying to find ways to be alone and kiss, but poor guy, I made him wait." She adds, "I think it was more tortuous for him because I was used to shutting that part [of me] off." Shields admits that her overbearing mother played a role in her sexual difficulties with Cain, and she split with the Lois And Clark star not long after.

Photo: IMDB

24. Britney Spears

Britney Spears claimed she was a virgin while she was dating Justin Timberlake in her heyday, but her mother, Lynne Spears, wrote in her memoir that the pop princess had sex for the first time when she was 14.

Photo: VEVO

25. Chris Brown

Chris Brown told The Guardian that he lost his virginity when he was eight years old  to a 14- or 15-year-old girl. Which, uh, is actually rape. Still, Brown reportedly laughed, "It's different in the country." Why? well, Brown said he and his cousins had watched a ton of porn as kids. "By that point, we were already kind of like hot to trot, you know what I'm saying?" he said. "Like, girls, we weren't afraid to talk to them; I wasn't afraid. So, at eight, being able to do it, it kind of preps you for the long run, so you can be a beast at it. You can be the best at it." Or so you can spend a lot of your life with really serious issues that you dismiss instead of addressing properly.

Photo: Twitter

26. Fergie

"I've always been a very sexual person," Fergie says. "I've always had to hold myself back. I lost my virginity at 18. But that took a lot of willpower."

Photo: IMDB

27. Kim Kardashian

Kim Kardashian basically sells sex for a living, but she's always been responsible about it. The now-Mrs. Kanye West said in an interview that losing her virginity was a big deal, and she was smart and safe when she did it: "We were sooo in love. I thought we were going to get married. I brought my mom in my bathroom and I'm like, 'Mom, I think I'm gonna have sex. I think I should go to the doctor and get put on birth control.' And my mom was like, 'Okay.' What else was she gonna say?" Knowing Kris Jenner, she probably said something like, "Get a camera and make this your living."

Photo: VEVO