10 Stars Share The Creepy Ways They Lost Their Virginity

It appears as no wonder that Hollywood is obsessed with stars’ private times. In almost any interview, journalists will attack famous stars and musicians with questions about who’s keeping them warm at night. Some fearless and more unabashed Hollywood starlets have no problem sharing their most salacious affairs. Here for your se**al appetite is a round up of some of the most noteworthy celebrity, virginity loss stories.

1. Angelina Jolie

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Jolie lost her virginity at the age of 14, considerably young for many. However, Jolie confessed that after she began making love with her then-boyfriend, she felt as if the connection wasn’t enough. During that, Jolie grabbed a knife and cut her boyfriend in order to force an experience of closeness.

2. Kim Kardashian

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According to Kardashian, she had been thinking of having sex with her boyfriend at the time, who could have possibly been Michael Jackson’s nephew TJ. At age 14, Kardashian confided in her mother. Kris Jenner gave Kardashian the talk and made sure she was protected.

3. Paris Hilton

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Two months after meeting in Palm Springs, Randy Spelling, the brother of Tori Spelling, took Paris Hilton’s virginity. Spelling recounted the story in which he tried to sneak off with the then 15-year-old heiress. The two eventually slipped out to do the deed, but were interrupted by everyone’s worst nightmare.

4. Tina Fey

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The comedian has consistently cracked jokes about how long it took her to lose her V-card. Fey told David Letterman that she waited until she was 24 to finally seal the deal with Jeff Richmond, who she incidentally wound up marrying.

5. Sarah Silverman

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In a personal essay, Sarah Silverman described in great detail about the time she lost her virginity. After going home with the emcee of an open night mic she worked at, Silverman allowed “Kevin” to walk her through her first time.

6. Jessica Simpson

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Jessica assured the media that she would wait until marriage to lose her virginity. At age 22, the singer shed her promise ring on her wedding night with former husband Nick Lachey. Although the marriage didn’t last, Simpson emphasized how important it was to her to remain a virgin until marriage at the time.

7. Katy Perry

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In a GQ spread, the pop singer described her first time in the front seat of a car. Perry recalled that she first had her first time “in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace.” Perry’s aesthetic puts Brand’s to shame.

8. Shia LaBeouf

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Shia LaBeouf retailed his first time. At age 18, LaBeouf sealed the deal with a close friend of his. In his own words, LaBeouf stated that “For some reason, I was trying to portray myself as a man who had done it many times in the past. I didn’t tell the girl I was a virgin.”

9. Ashton Kutcher

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Ashton Kutcher shared his awkward first-time experience with a girl he was set up with by a friend. Kutcher divulged highlights which included that “it was out in the woods with a girl [he] had just met” and “the whole thing lasted two seconds.” Feeling awkward and embarrassed, Kutcher couldn’t forget his first time.

10. Johnny Depp

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Johnny Depp lost his virginity while touring with his band The Flame. Only 13 years old at the time, Depp secured his quintessential bad boy image at a young age. Not only did Depp lose his virginity during his first teen year, but he also lost it to a groupie in the backseat of a car. His first time is considered legendary to say the least.


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