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First Times of the Rich and Famous

FIRST TIMES OF THE RICH AND FAMOUS

First Times Of The Rich And Famous

Everybody was a virgin at one time - even your favorite celebrities. From the awe-inspiring to the awkward, here's how these stars remember their first time.

Jessica Alba

The actress lost her virginity at age 18 to fellow Dark Angel actor Michael Weatherly (30).

Milton Berle

Claims to have lost his virginity at age 12 to a showgirl who caught him snooping in her dressing room. He stated, “I think the whole thing lasted two seconds.”

Mariah Carey

The singer claims to have lost her virginity at age 23 to Sony Music Chief, Tommy Mottola, on their wedding night. Think Tommy bought that one?

Cher

Cher had a one-night stand with Warren Beatty when she was an unknown 16-year-old and he was 25.

Joan Crawford

A 2002 Biography asserts that Joan was sent to a convent by her Mother at age 12 after being raped by her stepfather, Henry Cassin. However, according to Joan, he was "kind", and the relationship was "consensual." Ugh!

Miley Cyrus

Says she "didn't go all the way" until she was 16 with her future husband, Liam Hemsworth.

Johnny Depp

The Pirates Of The Caribbean actor admitted to having lost his virginity in the back of a car at age 13.

Sean "Diddy" Combs

The Producer revealed to Playboy that his first attempt at sex wasn't exactly a hit. “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."

Sean Connery

“The World’s Sexiest Man” claims to have lost his virginity when he was 8 years old. What?

Macaulay Culkin

The actor says he lost his virginity at 15. “It wasn’t gross or weird. We planned it. It was warm and sticky and I felt like, ‘Geez, this is weird. Am I doing it right?’”

Miley Cyrus

“I didn’t go all the way with a dude until I was 16, but I ended up marrying the guy,” the singer said on a podcast in August 2020.

Cara Delevingne

The Actress/Model admits she started having sex when she was 18. "I was quite late."

Celine Dion

The singer lost her virginity at age 20 to her manager and future husband, Rene Angelil.

Colin Farrel

The actor lost his virginity at 15, after meeting an Australian woman at a gay nightclub. Some 20 years his senior, she took him home, produced a basket full of condoms, and asked him to choose one.

Tina Fey

The Actress and Comedian lost her virginity at age 24 to her current husband, Jeff Richmond.

Carrie Fischer

Reports that Warren Beatty repeatedly offered to “relieve her of her virginity” at age 17 on the movie set of Shampoo. She declined.

James Franco

On losing his virginity: "In high school with my girlfriend. I think girls liked me, but I was awkward, shy, and emotionally immature, so I didn’t have a ton of girlfriends. I had short-term relationships and always got dumped, I think because I was too slow for them."

Lady Gaga

According to the singer, her first time was not a positive experience: 'I didn't lose my virginity until I was 17. But I have to say even then I wasn't ready and it was an absolutely terrible experience."

Janeane Garofalo

Janeane lost her virginity when she was 21 years old to her college boyfriend.

Robin Givens

The ex-wife of Mike Tyson admits she lost her virginity to Eddie Murphy.

Selena Gomez

The singer alluded to having lost her virginity at age 13 with then-boyfriend and fellow singer, Justin Bieber.

Jerry Hall

The former supermodel and ex of Mick Jagger once revealed the curious source of her first orgasm: Her friend 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." After Jerry’s horse-humping stage, she lost her virginity at age 14 to a rodeo bull rider who also deflowered her girlfriend.

Woody Harrelson

Lost his virginity at age 17. "Neither of us knew what we were doing, but we went at it feverishly -- until her parents showed up, with doors opening, bright lights, them screaming, me stuffing my underwear and her bra down the back of my pants."

Colton Haynes

Revealed to Andy Chen that he lost his virginity in 8th grade: “I lost my virginity at 13, to a girl and a guy,” Haynes said, explaining the female was 15 at the time and the male, 16. “I’ve never said that before.”

Paris Hilton

Lost her V-Card to Tori Spelling's brother, Randy Spelling, at age 15.

Dustin Hoffman

The star told an Australian publication that he lost his virginity at 15 by making believe he was his brother when he was in a darkened room. Afterward, when the woman saw his face and realized what happened, she screamed.

John Holmes

In classic porn style, Johnny Wad lost his virginity at age 12 to the 36-year-old mother of a friend.

Billy Idol

Th singer lost his virginity at age 11 to the song “Mony, Mony”. He later covered the song in 1980.

Angelina Jolie

The actress revealed a darker sexual experience to OK! “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."

Khloe Kardashian

Revealed on The View that her first time at age 14 was with an older partner who made her feel"conned."

Kim Kardashian

The reality star admitted to Oprah that she lost her virginity at age 14 to Michael Jackson's nephew, TJ Jackson.

Anthony Kiedis

According to Anthony’s autobiography “Scar Tissue,” the singer lost his virginity at the age of 12 to his father's girlfriend (with his father’s permission) Quote, “Dad, can I have my first sexual experience with your girlfriend?”… “Sure Son!”

Lisa Kudrow

The star of “Friends” says she lost her virginity at age 31, on her wedding night.

Ashton Kutcher

The actor admitted to Details Magazine that his first time wasn't exactly stellar. "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,”

John Legend

The singer told Cosmopolitan that he felt pressured into having sex at the young age of 12. "Just being around older people that were having sex, it felt like I had to catch up with everybody, I think a lot pressure when you’re a ‘cisgender male’ teen has to do with losing your virginity and negotiating relationships with women.

Adriana Lima

The Victoria's Secret model claims to have guarded her virginity until the ripe age of 27, when she married Marko Jaric in 2009.

Alanis Morissette

According to the Howard Stern show, Dave Coulier who played Joey on “Full House” deflowered Alanis when she was 19. Dave is also said to have inspired the song “You Oughta’ Know”.

Kate Moss

The model lost her virginity at age 14 on a family vacation in the Bahamas.

Iggy Pop

The punk icon admits he lost his virginity late in life. “The summer I was twenty”, he says. “I was old. People are like, yeah, he probably lost it at ten, eleven. No, I was older. It wasn’t so great. It wasn’t, like, a winner.”

Evita Peron

Before she achieved world fame as the glamorous and influential wife of Argentine president Juan Peron, lost her virginity at age 14 with tango singer Jose Armani.

Katy Perry

The singer admits that she lost her virginity at age 16 in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace. “Love that record so much,” she told GQ in 2014.

Lisa Marie Presley

Lisa told Howard Stern that she had lost her virginity at 15 to a drug dealer.

Jamie Pressly

Jamie 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'.

Daniel Radcliffe

The Harry Potter actor admits he had an enjoyable first time. “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.”

The Rock

Lost his virginity at 14 to an 18-year-old girl in a certain park in Hawaii where he grew up. He now requires a “moment of silence” when driving friends through the same park.

Dax Shepard

The actor revealed that he had lost his V-card at 12 or 13 years old: "I lost my virginity intentionally to 'Love My Way' by The Psychedelic Furs in the basement of my house," he shared at the time.

Sarah Silverman

Lost her virginity at age 19 to a "fellow comedian" who was 30.

Britney Spears

According to her Mother, Brit-Brit lost her virginity to a high school football player at 14 years old.

Jerry Stahl

Confessed to losing his virginity “to a hot-breathed waitress who took me to a Popeye’s Chicken stockroom on a school trip to Sea World.”

Oliver Stone

Oliver Stone has revealed his father, a Wall Street Financier, took him to a prostitute to lose his virginity. He states "For me it was great."

Gene Simmons

The "Prince of Darkness" claims to have lost his virginity to a housewife on his paper route at age 13.

Stuart Townsend

The Irish star, (a devout Catholic who once dragged his Mother to church) lost his virginity on an exchange trip to France to a married woman who kept a whip hanging over her bed.

Steven Tyler

The Aerosmith rocker lost his virginity to a prostitute at the tender age of 15 but had to wait until three of his pals had finished with her. He recalls, "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.”

Alex Van Halen

Alex claims to have lost his virginity one night after a gig at the ripe Rock-God age of nine.

Gore Vidal

When asked whether his first time was with a man or a woman his reply was “I was too polite to ask”.

Winona Ryder

The Stranger Things actress opened up about losing her virginity to fellow actor, Johnny Depp: “When I met Johnny, I was a pure virgin. He changed that. He was my first everything. My first real kiss. First real boyfriend. My first fiancé. The first guy I had sex with. So he’ll always be in my heart… Forever."

Brooke Shields

The actress lost her virginity to fellow actor (TV’s Superman) Dean Cain, while they were both attending Princeton University.

Jerry Springer

Jerry claims to have lost his virginity at age 17 in New Orleans with a $10 hooker.

Elizabeth Taylor

Reputedly lost her virginity at age 15 to actor Peter Lawford.

Ike Turner  

The former husband of singing sensation Tina Turner claims he lost his virginity to a 45-year-old-woman when he was just a child - and insists he wasn't in love. Ike says, "She was a neighbor named BOOZEY. It wasn't love - it was sex."

Andy Warhol

A biography states that the artist lost his virginity at 25 to his first boyfriend, though Warhol claimed never to have engaged in any sexual intercourse.

Lil Wayne

In a 2009 Playboy interview, the rapper stated, "I was 11 and the girl was 13. She had every board game you could imagine. I liked board games. We was playing Win Lose or Draw and on the board and she wrote, ‘Fu+k me.’ Now I was 11, and I didn’t even know it meant ‘intercourse.’

The Weeknd

Says he lost his virginity at age 16 to an older woman he met at a college Toga party. “I was drunk too. It was the worst experience of my life. Losing your virginity to an older woman sounds good, but it was kinda like, ‘Oh shit, it’s done?'”

I always thought of losing my virginity as a career move.

— Madonna

Aug 4th 2022 C. Ressi

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