Lists  Reviews  Images  Update feed
MoviesTV ShowsMusicBooksGamesDVDs/Blu-RayPeopleArt & DesignPlacesWeb TV & PodcastsToys & CollectiblesComic Book SeriesBeautyAnimals   View more categories »
Added by SFG¿mystic on 18 Sep 2012 04:52
85927 Views 4 Comments

When Celebs Lost Their V-cards

Add header image

Choose file... or enter url:
Sort by: Showing 43 items
Rating: List Type:
Average listal rating (1230 ratings) 6.8 IMDB Rating 0
Megan Fox lost her virginity at 17 to her first love, whom many assume is current boyfriend Brian Austin Green. "I've had plenty of awkward sex, but that first time was not awkward. I was in love with him and it was nice."
SFG¿mystic's rating:
Average listal rating (272 ratings) 6.7 IMDB Rating 0
Matthew Fox created a mini stir last week after revealing that he'd "become a man" at the age of 12 with a woman who "was about two years older than me." He added, "It was absolutely terrible and awkward -- just two f**king kids lying down and pulling our pants down.”
SFG¿mystic's rating:
Other stars, like Christina Aguilera, have made no bones about their desire to, well, bone. "I'm a proud, sexual girl -- a woman, actually," she said in 2001. "All this do-not-touch nonsense is not me. I'm no virgin, I'm all for female sexuality and taking the sexual power away from the guys. They've had it for way too long."
SFG¿mystic's rating:
Average listal rating (76 ratings) 7.1 IMDB Rating 0
Chris Martin remained a virgin until he was 22 years old -- but not by choice. "Well, I used to walk funny and, to be quite honest, I was a bit of a knobhead -- I wouldn't have liked me either."
Same goes for Jessica Simpson, who married Nick Lachey on Oct. 26, 2002. "I promised God, my father and my future husband that I would remain a virgin until I got married. I just always knew it was something I wanted to do."
Diddy wasn't even in double digits before he tried to get a girl into bed. "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." A mission that was finally completed three years later.

"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."
Average listal rating (430 ratings) 5.7 IMDB Rating 0
Unlike Diddy, Fergie didn't have trouble losing it -- she had trouble keeping it! "I've always been a very sexual person. I've always had to hold myself back - I lost my virginity at 18. But that took a lot of willpower."
Average listal rating (749 ratings) 6.6 IMDB Rating 0
"For some reason, I was trying to portray myself as a man who had [had sex] 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. 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.”
SFG¿mystic's rating:
Ashton Kutcher's first time was so bad he demanded a do-over years later. "It was out in the woods and it was horrible. 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 got much better."
Some stars wish they could have "done it" earlier, like Brooke Shields. “I think I would have lost my virginity earlier than I did at 22. I had the public and all this pressure, and I wish I had just gotten it over with in the beginning when it was sort of OK. I think I would have been much more in touch with myself.”
Awkward, disappointing sex stories are dime a dozen in (and out of) Hollywood. “I was 15 and it was with an older man I was absolutely besotted with, so I was very willing," Shirley Manson has said. "Unfortunately, it was a nothing experience, in his friend’s super low-fi bachelor pad with dirty pants and half-eaten bowls of cereal around the bed. It lasted 40 seconds. And I remember the words ‘Is that it?’ spinning around my head, cause, if that’s what it’s all about, someone has been telling me fibs.”
Average listal rating (174 ratings) 6.7 IMDB Rating 0
Steven Tyler lost his virginity to a lady of the night. “It was such a nasty experience."
Jaime Pressly revealed to Howard Stern that losing her virginity at 14 was a big mistake and the guy she was with “never finished.”
Average listal rating (21 ratings) 6.8 IMDB Rating 0
Kathy Lee isn't the only one to give too many details of their first time. On losing his virginity to Erin Moran, Scott Baio said, "I didn’t know what to do. 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... I was humping a corduroy sofa!"
For Kathy Lee Gifford the wait (her wedding night) was not worth it. "I’m sorry, but anyone who’s instantly relaxed with being naked in front of somebody for the first time and having someone explore intimate parts of the body is either lying about being relaxed — or lying about it being the first time. But [I had] some raging hormones going. I mean I was ready! I lost every inhibition I’d ever had. And yet we just couldn’t seem to get relaxed with each other. It saddens me to think about it now. I spent the first night of my married life sobbing my eyes out, feeling we had just made the biggest mistake of our lives."
Some stars, however, remain mum on the subject. When asked by Playboy when he lost his virginity, Matthew McConaughey says, "15." When pressed for details, he says, "[That's] none of your business. I don't tell bedroom tales. Never have."
Average listal rating (330 ratings) 5.9 IMDB Rating 0
Celine Dion also described her deflowering with husband Rene Angelil in elaborate detail.

"It was in Dublin, on that unforgettable day of April 30, 1988, the evening of the Eurovision competition. He went back to my room with me ... I was seated at the head of the bed, legs folded under the covers. I was happy about being alone with the man I loved. And I had a very precise plan. I took his head in my hands and I kissed him on the lips. I put my arms around his neck ... He held me tight, the door still open behind him. Then he removed my arms. He fled to his room. I stayed there for a moment all alone, my heart beating — trembling and dumbfounded. I knew that I’d won. The flight was an admission of it. I grabbed the telephone and called his room to tell him: 'If you don’t come back here immediately, I’m going to knock on your door.' But there was no answer. It was he who called me several minutes later from the lobby of the hotel. To ask if I was all right. And then he told me: 'If you really want to, I’ll be the first.' And I answered him: 'You’ll be the first. And the only.'"
SFG¿mystic's rating:
Average listal rating (788 ratings) 7.4 IMDB Rating 0
Even the world's most famous "Virgin" -- Steve Carell -- refuses to dish the deets. "I could invent 50 different responses (to questions about losing my virginity). It was on top of the Eiffel Tower and it was windy and cold and we were both shivering and in love. But the other was based on what my wife said when I approached her with the subject. She said, 'Don't tell them.' I guess I do that too. Ultimately, I think my response is, it was like everybody else's loss of virginity. It was so mundane, so average, so quick, so uneventful, so uninspiring and awkward and weird which I think everyone that has had the same sort of experience."
SFG¿mystic's rating:
Then there are stars who go into enough detail, it kinda feels like you were front and center for the fornicating. Angelina Jolie, who lost her virginity at 14 said, "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."
SFG¿mystic's rating:
Daniel Radcliffe's story became a British fascination as everyone tried to deduce the identity of his deflowerer. After revealing that he lost his virginity to an older woman when he was 16 years old, US Weekly revealed that the lady in question was Amy, a 23-year-old assistant hairdresser who he met on the "Harry Potter and the Goblet of Fire" set.
SFG¿mystic's rating:
Average listal rating (451 ratings) 7.5 IMDB Rating 0
Tina Fey, who lost her virginity at 24, says she couldn't give it away. “I remember bringing people over in high school to play that game, Celebrity. That’s how I successfully remained a virgin well into my 20s, bringing gay boys over to play Celebrity.”
SFG¿mystic's rating:
Average listal rating (55 ratings) 4.9 IMDB Rating 0
Although we're all very familiar with his recent conquests, Tiger's first foray into female terrain happened when the golfer was 16, allegedly with Dina Gravell. She says he was a clingy, possessive romantic who used to write love letters. A foreshadow of his sexting, perhaps?
Shanna Moakler described her most embarrassing moment ever as "when I lost my virginity." She told ESPN, "My dad's a dentist, and this guy and I were in his office. My mom walked into the next room and turned the light switch on and was like, 'Shanna?' The guy skyrocketed out across the room. Suffice to say, the passion never was the same between us."
Average listal rating (790 ratings) 6.3 IMDB Rating 0
It took Will Ferrell 21 years of making jokes as an excuse to talk to girls before one finally deflowered him. He told Rolling Stone in a recent interview that he lost his virginity his junior year of college. "In my mind’s eye, it seemed like the way it was supposed to happen,” he said. But the joke was on him. He revealed that his mom assumed his deflowering took place much earlier with a "loose" high school classmate. “She said, ‘If you slept with this girl, you’d better slap a condom on that pecker of yours.’” That sounds like an awfully awkward convo.
SFG¿mystic's rating:
Average listal rating (38 ratings) 6.3 IMDB Rating 0
Jerry Hall's first time orgasming was unorthodox -- and no, it wasn't with Mick Jagger. Try her horse, Flicka. "It was really cold and there was ice on the ground," she recalled. "I wanted to get warm so I opened my coat and lay over my horse. To get warm. It just happened. I was very lucky." She eventually lost her v-card at age 14 to a bull rider, which is better than an actual bull, amiright? [Tabu Toys]
Average listal rating (32 ratings) 4.4 IMDB Rating 0
It's also safe to say that once Kevin Jonas married Danielle this past December, taking off his purity ring was the first order of business.
Britney Spears' virginity has been hotly debated but in her mom's book, Through the Storm, Lynn Spears capitalizes on her daughter's fame and dishes all the dirt. She says her daughter did NOT lose her v-card to Justin Timberlake, like everyone thought. Instead, she gave it up to a high school football jock when she was 14.
SFG¿mystic's rating:
Matthew Morrison of "Glee" also didn't lose his virginity until he was 21. Why? Because in high school, he dated the homecoming queen who, like Quinn, shut things down and suggested praying anytime anything got too hot and heavy. "It was sweet," Matthew says. "It was innocent." Then in college, he joined a Bible-study group. But because he was a straight guy into musical theater, once his v-card was cashed, he became a little bit of a ho. "There was so much opportunity," he says. "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."
Oddly enough, Elvira had her cherry popped by the famous baby's arm that is Tom Jones. She once told Blender magazine that the singer's large member left her sore and bleeding. "Tom [Jones] seemed gentlemanly and nice, so when he was jumping on me... I thought, 'Well, if I'm ever gonna do this, it might as well be with Tom Jones.' It was painful and horrible." See? Bigger is not always better.
Average listal rating (359 ratings) 6.7 IMDB Rating 0
Lisa Kudrow should feel right at home with Brooke and Tina Fey, as she too waited a while to have sex for the first time, holding off until she married her husband. Of her virginity, Kudrow said, "My virginity was something I had decided was very precious, something that I owned, to give away. It was an honor I was bestowing on a young man, and he had to be worthy of it." I'm surprised she's not a more vocal abstinence advocate, aren't you?
Anthony Kiedis was gifted with his virginity loss -- by his own dad, Blackie. According to what he told his biographer,"One night, when Anthony was 12, he went with his father to the Rainbow Room and Blackie's girlfriend is there dancing for him. And Anthony asks, 'Dad, can I have my first sexual experience with your girlfriend?' And Blackie says, 'Sure, son.' So they go back to the house, and his dad builds a big bed out of four mattresses in his room and puts the girl in next to him. And that's how he (loses his virginity)."
Average listal rating (366 ratings) 6.6 IMDB Rating 0
In Kate Moss: Model of Imperfection, an unauthorized biography, author Katherine Kendall dishes on Kate Moss' sexcapades. Kendall claims that Moss got hot n' heavy for the first time in the Bahamas when she was just 14. Kate supposedly went over the book carefully and planned to sue if any details weren't true, but this little factoid stayed.
Marilyn Manson wrote about his first time ever (with a girl named Tina) in The Long Road Out Of Hell:

We sat down on the side of a hill. Instantly, we began making out, and within minutes I had my hand down her pants. The first thing that went through my mind was how hairy she was. Maybe she didn't have a mother to teach her about shaving her bikini line ... Just the thrill of penetration was enough to make me orgasm, and before I was even in all the way, it was over. It was literally pump and dump.
Average listal rating (641 ratings) 3.3 IMDB Rating 0
When he was 26, nasty pants Randy Spelling (he's Tori's loser brother) took 15-year-old Paris Hilton's virginity. Dude, she wasn't even legal.
Average listal rating (3235 ratings) 8.7 IMDB Rating 0
Badass sexpot Johnny Depp used to play guitar in a rock band called The Flame. Well, things got hot as a flame when, at 13, Depp lost his virginity to a groupie in the back of the band's van. This seems a bit young. But I guess we would have done the same if presented with Johnny's johnny.
SFG¿mystic's rating:
Sienna Miller gave it up to her first "serious" BF when she was 16. Her mom insisted that they get it on in the house because she didn't want little Sienna doin' it outside. Ooookay, we hope her mom at least left the house while the couple had their, er, moment.
SFG¿mystic's rating:
Average listal rating (1052 ratings) 8.1 IMDB Rating 0
In a book called Where Do Nudists Keep Their Hankies? the author claims that Sean Connery began getting it on at the ridiculously young age of 8. Sean says, "I was 8, but I can’t recall with whom.” For some reason, we think he's lying. Who forgets their first time?
I can figure it out from the photo.
SFG¿mystic's rating:
Khloe Kardashian: 14. The reality star told the ladies at 'The View' that she felt "disgusted" after she lost her virginity at the young age of 14 to an older man. "I should have listened to my parents," Khloe said, "Don't let anyone pressure you, it's not worth it and how I felt afterward."
Ozzy Osbourne may be crazy and old now, but he was hot stuff when he was younger. He was doin' it by the time he was 14. Papa obvs doesn't preach because his daughter, Kelly, ended up losin' it at 16. Their v-cards aren't the only thing the Osbournes have trouble holding on to. Their sanity seems to be slipping away too.
At the age of 15 the 'Graduate' star lost his virginity at a New Year's Eve party to an older woman who mistook him for his brother in a dark room. Whoops!
SFG¿mystic's rating:
Today in terrible parenting news, Russell Brand's dad brought little Russell to a Hong Kong brothel to do the deed for the first time. "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."
Average listal rating (537 ratings) 7.7 IMDB Rating 0
A few character-forming years spent jumping up and down at contemporary clubs like the Music Machine and Vortex, shouting "Kill the hippies" and trying to get off with punkette girls ("I never got any"), then off went Roth to sixth-form college. "I lost my virginity there," he remembers with satisfaction. "To a girl. In sculpture class.

Thank you Yulle.
SFG¿mystic's rating:
Average listal rating (728 ratings) 8.4 IMDB Rating 0
She may be the fantasy of men everywhere but this Victoria's Secret model held out on having sex until she was 27 years old when married.

Added to

33 votes
Celebs Life & Death (65 lists)
list by SFG¿mystic
Published 3 years, 5 months ago
8 votes
SFG¿mystic - The Ultimate List (99 lists)
list by SFG¿mystic
Published 3 years ago

Related lists

Like a virgin
71 item list by fabrizius
24 votes 3 comments
Cigarette Cards: Birds & Their Young
50 item list by Supernaut
9 votes
WatchMojo's Top 10 Shows That Lost Their Mojo
10 item list by Leo
2 votes
You Smell Nice!
28 item list by TrekMedic
44 votes 3 comments
Shows I Lost Interest In
12 item list by Liss
19 votes 8 comments
Lost Generation
6 item list by nusch
12 votes 3 comments
Xmas & New Year & Easter Cards
15 item list by The O.P.
11 votes 4 comments
Cigarette Cards: Playing Cards - Actresses
53 item list by Supernaut
11 votes

View more top voted lists

People who voted for this also voted for

More lists from SFG¿mystic


Posted: 3 years ago at Sep 18 14:58
Suggestion of Tim Roth:

"-- A few character-forming years spent jumping up and down at contemporary clubs like the Music Machine and Vortex, shouting "Kill the hippies" and trying to get off with punkette girls ("I never got any"), then off went Roth to sixth-form college. "I lost my virginity there," he remembers with satisfaction. "To a girl. In sculpture class." --"

The full article: http://www.tim-roth.com/index.php?id=lifeapr95

So he was probably 16 years old. Great list, btw !
Posted: 3 years ago at Sep 24 18:18
I like this list, very informative on the 'V-Card' of celebrities...

Wait, so is that what inspired a then older Paris Hilton to do her sex tape scandal, nice job Randy Spelling, Ha!!

but this list is great, thanks!! :)
Posted: 2 years, 9 months ago at Dec 18 2:48
Wow! A spicy list.....lol....
Posted: 5 days, 8 hours ago at Oct 8 13:06
Randy Spelling and Paris Hilton are the same age... He was born in 1978 and she was born in 1981, what the hell were you guys looking at?

Login or Signup to post a comment

Insert image

drop image here
(or click)
or enter URL:
 link image?  square?

Insert video

Format block