20 Celebrities Expose Who Lost Their Virginity Shockingly Young

It comes as no surprise that Hollywood is obsessed with celebrities’ sex lives. In almost any interview, reporters will bombard famous actors and musicians with questions about who’s keeping them warm at night. Although many celebrities play coy with non-answers, some bolder and more unabashed Hollywood starlets have no problem sharing their most salacious affairs.

Losing your virginity is a big deal for anyone, even celebrities. Depending on the type,celebrity virginity stories can range from the hilarious to the romantic, to the devastating, to the flat out embarrassing. Lucky for fans, a lot of stars have opened up about their first times with the public. Here for your sexual appetite is a round-up of some of the most noteworthy celebrity, virginity loss stories.
1. Paris Hilton

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.

2. Jessica Simpson

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.

3. Katy Perry

In stark contrast to her ex-husband’s tale, Katy Perry had quite the romantic experience losing her virginity. In a GQ spread, the pop singer described her first time in the front seat of a car. Perry recalled that she first had sex “in the front seat of a Volvo sedan while listening to Jeff Buckley’s album Grace.” Perry’s aesthetic puts Brand’s to shame.

4. Nick Cannon

On an episode of Lopez Tonight, Cannon revealed that he was only in middle school when he had sex for the first time. Cannon recalled how he lost his V-card in a sleeping bag with a high school girl. But when Cannon suggested they try a different position, the older girl shouted “just get off of me!” A poor, deflowered Cannon remember how “she ran into the bathroom with all of her friends and they were in there laughing.” Completely embarrassed by the experience, Cannon left in tears.

5. Johnny Depp

One of the most notoriously well-known celebrity sex stories, 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.

6. Jason Segel

Jason Segel let the audience in on how he wooed the ladies into bed with him. Segel taught himself how to play piano at age 17. Ambitious nonetheless, but Segel’s true motives were to capture the affection of his female classmates. Segel revealed to listeners that he would convince “not-that-intelligent” girls into believing that he wrote Elton John’s classic “Your Song.” He would tell girls “I wrote this for you.” And apparently that is what subsequently led him into the sack for the first time.

7. Shia LaBeouf

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.” In an effort to prove his manliness, LaBeouf attempted to mimic moves he had seen in pornos. He recalled putting a pillow underneath her which “put her at a weird angle, where I couldn’t get in correctly. I’m not extremely well-endowed.”

8. Sarah Silverman

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. Initially nervous, Silverman felt proud after making it unscathed through her first sexual encounter.

9. Tina Fey

Tina Fey is anything but shy when discussing her sex life. 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.

10. Angelina Jolie

Jolie lost her virginity at the age of 14, considerably young for many. However, Jolie confessed that after she began having sex with her then-boyfriend, she felt as if the connection wasn’t enough. During sex, Jolie grabbed a knife and cut her boyfriend in order to force an experience of closeness. According to Jolie, her boyfriend cut her back in “an exchange of something and we were covered in blood, my heart was racing.

11. Kim Kardashian

Kim Kardashian isn’t exactly shy when it comes to her sex life, especially considering her sex tape with Ray J is what made her a household name. And when asked about her first time, the Kardashian was equally confident in telling her story. 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.

12. Nicole Polizzi

Snooki shared the story of her deflowering. The experience was an all around terrible and horrifying experience for the reality TV star, but that didn’t stop her from dropping all the gross details in true Jersey Shore fashion. Snooki recalled being terrified of the possibility of a pregnancy. But the guy, who she now calls “a jerk,” didn’t have a condom.

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