Before they were stars, celebrities were just fumbling around like anybody else — with some losing their virginity as stars, and one beauty holding out until she was in her 30s! Click through the gallery above to get the inside story on Katy Perry, Macaulay Culkin, Khloé Kardashian, Britney Spears, Angelina Jolie, Gillian Anderson, Johnny Depp, and more famous ex-virgins as they reveal details of their most intimate secret…
Celebrity Virginity Stories — Tales Of The Stars’ First Times
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22
1 of 22
Britney Spears
Britney Spears' own mother revealed in a tell-all book that Britney was just 15 years old when she scored a touchdown with a high-school football player in her Louisiana hometown.
Photo credit: Getty Images
2 of 22
3 of 22
Ashton Kucher
"I was 15," recalled Ashton Kutcher, who was upfront about some male vanity. "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."
Photo credit: Getty Images
4 of 22
Paris Hilton
Paris Hilton skipped the City of Lights and lost her virginity at the age of 15 in Palm Springs — to ex-soap actor Randy Spelling, who's also the brother of Tori Spelling. “We were together for, like, two months,” recalled Randy.
Photo credit: Getty Images
5 of 22
Bryan Cranston
Breaking Bad star Bryan Cranston got broken in by a hooker! In his memoir, A Life in Parts, the former Malcolm in the Middle dad revealed that he lost his virginity to a prostitute while he was studying overseas as a teen! “For her, it’d been an utterly forgettable moment,” he wrote. “But it was a moment I’d never forget.”
Photo credit: Mega
6 of 22
Macaulay Culkin
Macaulay Culkin told Anna Faris during her podcast about being home alone with a girl for his first time, saying: "I was about 15. It wasn't gross or weird; we planned it...It was warm and sticky and I thought like, 'Geez, this is weird. Am I doing it right?'" The former child star also put in a plug for his personal soundtrack, saying: "And also, we listened to the [Beatles'] 'White Album.'"
Photo credit: Getty Images
7 of 22
Fergie
Fergie was a perfectly legal 18-year-old when the future The Black Eyed Peas babe revealed her lovely lady humps for her first boyfriend, “I’ve always had to hold myself back,” she said. “But that took a lot of will power!”
Photo credit: Corbis
8 of 22
Johnny Depp
Johnny Depp was already rocking out with a band called The Flame at the age of 13 — and the young guitarist rocked the back of a van with a groupie for his big debut!
Photo credit: Getty Images
9 of 22
Lisa Kudrow was a true Hollywood rarity as a 32-year-old virgin when she married ad executive Michel Stern in 1995. “When I was young, I had always hoped and wanted to be a virgin when I got married,” said the Friends star.
Photo credit: Getty Images
10 of 22
Celine Dion
Celine Dion lost her virginity to an older man and her future husband René Angélil, who was then her manager — and her autobiography revealed in the romantic scene: "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."
Photo credit: Getty Images
11 of 22
Katy Perry was another Sweet 16 surprise, with her own “Teenage Dream” occurring in the front seat of a Volvo — set to the music of Jeff Buckley’s “Grace” album — with Katy adding: “I love that record!”
Photo credit: Getty Images
12 of 22
Snooki
Jersey Shore star Snooki wasn't romantic about recalling her first time, saying: "I was 14. I mean, in upstate New York, there's really nothing to do up there but experiment. He was a senior, and I thought he liked me — but turned out he was just a jerk. So, it was terrible."
Photo credit: Getty Images
13 of 22
Dustin Hoffman
Dustin Hoffman had his own Mrs. Robinson at the age of 15, but it was even less romantic than his pairing in The Graduate. Dustin claims that he only made the auld acquaintance with the lady at a New Year’s Eve party after she mistook him for his brother, Ronny.
Photo credit: Getty Images
14 of 22
Angelina Jolie
Angelina Jolie was a bad girl from the start — and her first lover might regret taking her virginity at 14 years old. “In a moment of wanting to feel closer to him, I grabbed a knife and cut him,” Angeline recalled. And though she's a good mom now, that's also a reminder of how she wore a vial of her husband's blood while married to Billy Bob Thornton.
Photo credit: Getty Images
15 of 22
Jessica Simpson
Jessica Simpson was "sexual napalm in bed" to womanizing rocker John Mayer, but the former pop star says that she first saved herself for ex-husband Nick Lachey — and didn't regret the honeymoon! “It was the most amazing moment of my life,” she said.“I’m so lucky I didn’t lose my virginity in the back of a Jeep or something. Instead, I had this amazing, elaborate wedding and I topped it off with that.”
Photo credit: Getty Images
16 of 22
Maksim Chmerkovskiy
Maksim Chmerkovskiy revealed in an interview that he was sweet 16 when he had his first sexual encounter with an older supermodel. The Dancing with the Stars pro added that his first horizontal mamba teacher had "ended up lying about her age" during the 1996 encounter. "She was about 10 years older than she said," insisted Maksim, "and it made her, like, in her early 30s — and it was amazing!"
Photo credit: Mega
17 of 22
Brooke Shields
Brooke Shields didn't let anything get between her and Calvins until she was 22 years old! If she’d had sex earlier, “I would have been much more in touch with myself,” she said.
Photo credit: Getty Images
18 of 22
Tommy Lee Jones
Tommy Lee Jones was only 13 years old when he ended up with his sister's best friend in the family garage — only to be caught by his infuriated sibling! “She told my parents," Tommy recalled. "It was all bad.”
Photo credit: Getty Images
19 of 22
Gillian Anderson
Gillian Anderson opened up her Sex Files at the age of 13 — but she isn't sentimental about her first experience with a “punk guy” who later turned into a Neo-Nazi! She looks back on the moment as “awkward, stupid, unadulterated crap.”
Photo credit: Getty Images
20 of 22
Selena Gomez
Selena Gomez seemed to suggest that the purity ring that she wore while dating Nick Jonas had slipped off while she was dating Justin Bieber — telling the U.K.'s Sunday Times: “I didn’t think I was doing anything bad by falling in love. There’s such an emphasis on people being the perfect thing, and then destroying them because it’s good press. Throw in the fact that you’re a teenager — it makes it more difficult.”
Photo credit: Getty Images
21 of 22
Kevin Jonas
Kevin Jonas recalled that his wedding night with wife Danielle was a letdown, Kevin was a 22-year-old groom, and said: “After we did it, I was kind of like, 'That’s it?'”
Photo credit: Corbis
22 of 22
Khloé Kardashian
Khloé Kardashian regrets getting together with an older man when she was just 15 years old — as she was left feeling “disgusted,” she recalled. “I should have listened to my parents,” she added. “Don’t let anyone pressure you; it’s not worth it and how I felt afterward.”
Photo credit: Corbis
Britney Spears
Britney Spears' own mother revealed in a tell-all book that Britney was just 15 years old when she scored a touchdown with a high-school football player in her Louisiana hometown.
Photo credit: Getty Images
Daniel Radcliffe
Daniel Radcliffe enjoyed a Very Sweet 16 as Harry Potter! Daniel revealed how the teen star opened the sexual Chamber of Secrets with the help of his 23-year-old girlfriend.
Photo credit: Getty Images
Ashton Kucher
"I was 15," recalled Ashton Kutcher, who was upfront about some male vanity. "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."
Photo credit: Getty Images
Paris Hilton
Paris Hilton skipped the City of Lights and lost her virginity at the age of 15 in Palm Springs — to ex-soap actor Randy Spelling, who's also the brother of Tori Spelling. “We were together for, like, two months,” recalled Randy.
Photo credit: Getty Images
Bryan Cranston
Breaking Bad star Bryan Cranston got broken in by a hooker! In his memoir, A Life in Parts, the former Malcolm in the Middle dad revealed that he lost his virginity to a prostitute while he was studying overseas as a teen! “For her, it’d been an utterly forgettable moment,” he wrote. “But it was a moment I’d never forget.”
Photo credit: Mega
Macaulay Culkin
Macaulay Culkin told Anna Faris during her podcast about being home alone with a girl for his first time, saying: "I was about 15. It wasn't gross or weird; we planned it...It was warm and sticky and I thought like, 'Geez, this is weird. Am I doing it right?'" The former child star also put in a plug for his personal soundtrack, saying: "And also, we listened to the [Beatles'] 'White Album.'"
Photo credit: Getty Images
Fergie
Fergie was a perfectly legal 18-year-old when the future The Black Eyed Peas babe revealed her lovely lady humps for her first boyfriend, “I’ve always had to hold myself back,” she said. “But that took a lot of will power!”
Photo credit: Corbis
Johnny Depp
Johnny Depp was already rocking out with a band called The Flame at the age of 13 — and the young guitarist rocked the back of a van with a groupie for his big debut!
Photo credit: Getty Images
Lisa Kudrow was a true Hollywood rarity as a 32-year-old virgin when she married ad executive Michel Stern in 1995. “When I was young, I had always hoped and wanted to be a virgin when I got married,” said the Friends star.
Photo credit: Getty Images
Celine Dion
Celine Dion lost her virginity to an older man and her future husband René Angélil, who was then her manager — and her autobiography revealed in the romantic scene: "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."
Photo credit: Getty Images
Katy Perry was another Sweet 16 surprise, with her own “Teenage Dream” occurring in the front seat of a Volvo — set to the music of Jeff Buckley’s “Grace” album — with Katy adding: “I love that record!”
Photo credit: Getty Images
Snooki
Jersey Shore star Snooki wasn't romantic about recalling her first time, saying: "I was 14. I mean, in upstate New York, there's really nothing to do up there but experiment. He was a senior, and I thought he liked me — but turned out he was just a jerk. So, it was terrible."
Photo credit: Getty Images
Dustin Hoffman
Dustin Hoffman had his own Mrs. Robinson at the age of 15, but it was even less romantic than his pairing in The Graduate. Dustin claims that he only made the auld acquaintance with the lady at a New Year’s Eve party after she mistook him for his brother, Ronny.
Photo credit: Getty Images
Angelina Jolie
Angelina Jolie was a bad girl from the start — and her first lover might regret taking her virginity at 14 years old. “In a moment of wanting to feel closer to him, I grabbed a knife and cut him,” Angeline recalled. And though she's a good mom now, that's also a reminder of how she wore a vial of her husband's blood while married to Billy Bob Thornton.
Photo credit: Getty Images
Jessica Simpson
Jessica Simpson was "sexual napalm in bed" to womanizing rocker John Mayer, but the former pop star says that she first saved herself for ex-husband Nick Lachey — and didn't regret the honeymoon! “It was the most amazing moment of my life,” she said.“I’m so lucky I didn’t lose my virginity in the back of a Jeep or something. Instead, I had this amazing, elaborate wedding and I topped it off with that.”
Photo credit: Getty Images
Maksim Chmerkovskiy
Maksim Chmerkovskiy revealed in an interview that he was sweet 16 when he had his first sexual encounter with an older supermodel. The Dancing with the Stars pro added that his first horizontal mamba teacher had "ended up lying about her age" during the 1996 encounter. "She was about 10 years older than she said," insisted Maksim, "and it made her, like, in her early 30s — and it was amazing!"
Photo credit: Mega
Brooke Shields
Brooke Shields didn't let anything get between her and Calvins until she was 22 years old! If she’d had sex earlier, “I would have been much more in touch with myself,” she said.
Photo credit: Getty Images
Tommy Lee Jones
Tommy Lee Jones was only 13 years old when he ended up with his sister's best friend in the family garage — only to be caught by his infuriated sibling! “She told my parents," Tommy recalled. "It was all bad.”
Photo credit: Getty Images
Gillian Anderson
Gillian Anderson opened up her Sex Files at the age of 13 — but she isn't sentimental about her first experience with a “punk guy” who later turned into a Neo-Nazi! She looks back on the moment as “awkward, stupid, unadulterated crap.”
Photo credit: Getty Images
Selena Gomez
Selena Gomez seemed to suggest that the purity ring that she wore while dating Nick Jonas had slipped off while she was dating Justin Bieber — telling the U.K.'s Sunday Times: “I didn’t think I was doing anything bad by falling in love. There’s such an emphasis on people being the perfect thing, and then destroying them because it’s good press. Throw in the fact that you’re a teenager — it makes it more difficult.”
Photo credit: Getty Images
Kevin Jonas
Kevin Jonas recalled that his wedding night with wife Danielle was a letdown, Kevin was a 22-year-old groom, and said: “After we did it, I was kind of like, 'That’s it?'”
Photo credit: Corbis
Khloé Kardashian
Khloé Kardashian regrets getting together with an older man when she was just 15 years old — as she was left feeling “disgusted,” she recalled. “I should have listened to my parents,” she added. “Don’t let anyone pressure you; it’s not worth it and how I felt afterward.”
Photo credit: Corbis
