Celebs Dish On When And How They Lost Their V-Cards

Tina Fey

Anthony Kiedis

Marilyn Manson

Celine Dion

NSFL

Jerry Hall

Steven Tyler

Kathie Lee

Elvira

Jaime Pressly

Brooke Shields

Lisa Kudrow

Matthew Fox

River Phoenix

Grace Kelly

Flavor Flav

Tiger Woods

Diddy

Shia LaBeouf

Ashton Kutcher

The always classy Scott Baio

Before they were rich, famous, and desired by the masses, all celebrities were once virgins. (Some still are, of course.) Just think about it—someone out there devirginized George Clooney ... Brad Pitt. Plenty of celebrities keep mum about their first time in the sack—but plenty of others share the dirty details. Keep clicking to find out who, what, where, and when it all went down when these celebs turned in their v-cards.Tina Fey didn’t lose her virginity till the ripe age of 24, telling David Letterman she “couldn’t give it away” and explained to Vanity Fair, “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.” Sounds like a normal Friday night for me!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,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).”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.Celine Dion’s first time was naturally with her much older manager-turned-hubby, René Angélil., who she says she pursued sexually. She wrote in My Story, My Dream: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.”Jerry Hall’s first time orgasming was unorthodox—and no, it wasn’t with Mick Jagger.“It was really cold and there was ice on the ground,” she recalled.She eventually lost her v-card at age 14 to a bull rider, which is better than an actual bull, amiright?Steven Tyler’s first time was with a lady of the night. He said, “By the time I got there, she was very loose and very wet. It was such a nasty experience. I had to wash my penis in the sink.” Well, then.Poor Kathie Lee! After waiting until age 22 to finally have sex, she gave it up to her first husband on their wedding night and the experience was less than awesome. She wrote in her autobiography, I Can’t Believe I Said That!: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. Believe me, I was neither lying nor relaxed. I just don’t think that kind of thing comes naturally to most people. Not in the world I came out of. In fact,But [I had] some raging hormones going. I mean I was ready! My lifelong self-consciousness about my body seemed, miraculously, to fade right away ... let me tell you,Relaxed? Forget it!I lost every inhibition I’d ever had. It was time for candles and romance, time to boogie and swing from the chandeliers.And yet we just couldn’t seem to get relaxed with each other. It saddens me to think about it now. We were so uncomfortable with each other, and I felt responsible and disappointed for both of us. I spent the first night of my married life sobbing my eyes out, feeling we had just made the biggest mistake of our lives.Oddly enough, Elvira had her cherry popped by the famous baby’s arm that is Tom Jones.“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.’See? Bigger is not always better.Jaime Pressly told Howard Stern that she lost her virginity at the age of 14, but at such a young age she complained it wasn’t a good experience as she was “too tight” and the guy she was with “never finished.” Ahh, too tight. Those were the days…Brooke Shields apparently gave it up to Dean Cain in college, but wishes she had done it earlier than age 22. She told Health magazine:“I think I would have had sex a lot earlier! 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. I think I wouldn’t have had issues with weight—I carried this protective 20 pounds [in college]. It was all connected. And to me, that’s a health regret.”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?Matthew Fox just dished to Playboy that he lost his virginity at age 12 to a woman who “was about two years older than me. It wasn’t her first time.” He continued: “I can actually see the event in my mind’s eye, like photographs. 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 f**king kids lying down and pulling our pants down.”In an interview with Details Magazine in November 1991, Phoenix claimed he lost his virginity at age 4 while in the Children of God..."I'm glad I did it when I was young," River once said, perhaps trying to justify the unjustifiable. "But I didn't want those & different body parts that were in my face to make me perverse when I was older, so I blocked it all out. I was completely celibate from 10 to 14. You're just born into that reality, and you accept it." [ rickross.com "On the threshold of Grace’s wedding, her mother Margaret proudly boasted, “Men began proposing to my daughter Grace when she was barely 15.” Grace was encouraged by her parents to date as much as she wanted, and she took full advantage of their laissez-faire attitude.... the first was with Paul “Skinny” D’Amato. Involved with the mob and not the least bit interested in her, he was the first of a series of unattainable married men she longed to captivate yet failed to ensnare.With her liberal attitude to sex, it was no surprise that she had already lost her virginity at 17 (to the husband of one of her girlfriends) before she left Philadelphia for Manhattan." [ Express.co.uk "I lost my virginity in the bushes on a box... A girl and me were having sex on a box in the bushes, in some big tall bushes... I lost my virginity when I was 6 years old.... Because you know 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, I penetrated for about a few seconds." [ complex Dina Gravell, a blonde with blue eyes, met Tiger when she was 17 and he was 16 in a high school accounting class in Calif.The woman, who took Tiger Woods’ virginity describes a teenage Woods as a clingy, possessive romantic who liked to write love letters. The pair dated for more than three years and even made plans to get married. [ NYPost On his childhood mission to lose his virginity:"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."On finally losing it:"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." [ BET The Transformers 2 actor, who finally admitted this week that he dated Rihanna a few years back, tells Playboy all about the fateful night in Canada, which was only four years ago, when he was the ripe old age of 18.“For some reason, I was trying to portray myself as a man who had done it (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.”He added, “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.” [ Social butterflies This sexy hunk who's Demi Moore's man had a rather unpleasant first stand. Kutcher revealed to a UK-based tabloid: "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.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." Well, Ashton life's all about second chances, didn't we tell you that!"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 twenty 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!""I got tight with Charles Laufer, the owner and publisher of Tiger Beat, which became an effective promotional tool…. One girl sent me her underwear that she’d peed and menstruated in, didn’t wipe and ran a mile in, so I could have her natural body fluids and odors."’I really want your sperm. You’re a talented, good-looking Italian guy. That’s what I want my child to be.’ I was incredulous. ‘What are you gonna do with my sperm?’ ‘Well, I’m going to take my egg and put it into somebody else’s body.’" [ SERIOUSLY? OMG Sean Connery: Age 8Lil Wayne: Age 11Johnny Depp: Age 13Kelly Osbourne: Age 13Britney Spears: Age 14Kate Moss: Age 14Angelina Jolie: Age 14Ozzy Osbourne: Age 14Paris Hilton: Age 15Matthew McConaughey: Age 15Cheryl Cole: Age 15Daniel Radcliffe: Age 16Sienna Miller: Age 16Woody Harrelson: Age 17Megan Fox: Age 17Fergie: Age 18Chace Crawford: Age 18Jessica Alba: Age 18Kathy Griffin: Age 19Jessica Simpson: Age 22Kevin Jonas: Age 22Elton John: Age 23