Which celebrities did these stars lose their v-card to?

Britney Spears to Justin Timberlake? - While it was long believed that Spears lost her virginity to pop star Justin Timberlake, it actually happened way before Timberlake was even in the picture. Apparently, Spears was sexually active at 14 years old and did it for the first time with a high school football player.

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Kristen Stewart to Michael Angarano - Kristen Stewart lost her virginity to actor Michael Angarano at the age of 14. They dated for four years.

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Mila Kunis to Macaulay Culkin - Before Ashton, Kunis was in a long-term relationship with the 'Home Alone' actor, and she gave him her virginity.

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Tina Fey to Jeff Richmond - The comedian and actress was 24 when she lost her virginity, and did it with the man who became her husband, composer Jeff Richmond.

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Hilary Duff to Joel Madden - Duff described her former relationship with the Good Charlotte lead singer as intense. Duff was just a teen and he was 26. She has lead people to believe that she lost her V-card to the famous rocker.

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Jessica Alba to Michael Weatherly - Alba was engaged to the actor (whom she began dating at the age of 18) and ultimately lost her virginity to him.

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Jessica Simpson to Nick Lachey - Simpson lost her virginity to her former reality television costar. She waited until marriage, although the two singers eventually divorced.

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Mandy Moore to Wilmer Valderrama? - In an interview with Howard Stern, Valderrama bragged about taking Moore's virginity, whom he briefly dated when she was a teenager. Over a decade later, Moore spoke to Stern herself to tell her side of the story... and said Valderrama lied!

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Paris Hilton to Randy Spelling - A young Paris Hilton lost her virginity to actor Randy Spelling at just 15 years old in a hotel room (the Hilton, perhaps?). Their beautiful teenage affair was eventually ruined by Hilton's grandmother, and the pair broke up a week later.

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Jordin Sparks to Jason Derulo - Derulo said that his then-girlfriend was a virgin when they began dating. Also a former wearer of a purity ring, Sparks removed it during their relationship and time together.

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Vanessa Hudgens and Zac Efron - The 'High School Musical' on- and off-screen couple had their first time with each other. Aww!

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Adriana Lima to Marko Jaric - Lima was married to the Serbian basketball star and followed the old-school path, having waited until she said "I do."

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Joe Jonas to Ashley Greene - This former purity-ring-wearing Jonas brother lost his virginity at 20 years old to his then-girlfriend, actress Ashley Greene.

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Nick Jonas to Olivia Culpo - Jonas' younger brother Nick Jonas also stopped wearing his chastity ring after losing his virginity to his then-girlfriend, beauty queen Olivia Culpo.

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Kevin Jonas to Danielle Deleasa - The only Jonas brother to actually keep his promise to wait until marriage was the oldest, Kevin Jonas. He met his wife Danielle Deleasa and lost his virginity to her upon marrying.

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Tamera Mowry to Adam Housley - The daytime talk show host waited to lose her virginity. At 29 years old, she lost it to her now-husband and Fox News correspondent Adam Housley.

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Tia Mowry to Corey Hardict - Like her sister, Mowry waited to be intimate with her now-husband, actor Corey Hardict. She waited until she was 25.

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Aaliyah to R. Kelly - The late R&B princess lost her virginity to a man she was formerly illegally married to, singer R. Kelly.

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Beyoncé to Jay-Z -

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Miley Cyrus to Liam Hemsworth - The pop star swiped her V-card for actor Liam Hemsworth.

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Selena Gomez to Justin Bieber - The singer-actress stopped wearing her chastity ring after she began dating Canadian singer Justin Bieber, implying that she lost her virginity to him.

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Kirsten Dunst to Jake Gyllenhaal - But before Swift, there was another blonde bombshell in Gyllenhaal's life. The stunning actress gave her virginity to the actor whom she began dating at 19.

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Brooke Shields to Dean Cain - In her memoir, the actress admitted to losing her virginity in college at age 22 to Superman himself.

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Kim Kardashian to TJ Jackson - The reality television star lost her virginity at 14 to Michael Jackson's nephew and a member of 3T, TJ Jackson.

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