20 Celebrities Reveal The Disturbing Ways They Lost Their Virginity - #18 Will Stun You!

Ethan Tremblay November 29th 2016 Entertainment
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. When the spotlight's main focus is sex, sex, sex, major celebrities often feel obliged to offer insight into their past sexual conquests. Although considered a private topic, many famous personalities have opened up about their first times having sex. 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. It may have taken them years to get over these sloppy flashbacks to bad sex, but these celebrities have told their stories with both humor and integrity. Here for your sexual appetite is a round up of some of the most noteworthy celebrity, virginity loss stories.

1. Angelina Jolie

Could it be possible that Angelina Jolie incorporated some real life experience into her infamous Girl, Interrupted role? According to an interview she gave to Ok! magazine, 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. Then whenever I felt trapped, I'd cut myself."

2. 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. Kardashian then went on to praise her mother, Kris, for advising she go on the pill and for being "really open and honest with [her]."

3. 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. In his own words, Spelling stated: "I hear this knock knock knock on the door, and I look out and her grandma's there. And then I look out the window and I see Paris in a full-on dress with a suitcase running down the golf course." Mortified is an understatement.

4. 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. Joking with Letterman, Fey attributed her chastity to "just good, Christian values... or bein' homely."

5. Sarah Silverman

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. Initially nervous, Silverman felt proud after making it unscathed through her first sexual encounter. However, when her new lover pulled back the sheets, it revealed "a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint." Following an incredibly long, awkward silence, Silverman hilariously remarked: "That came out of you." Silverman claims his only response was "Um. No it didn't. It's OK. Just buy me new sheets." At least he was understanding...

6. Jessica Simpson

Although Jessica Simpson was considered a blonde bombshell during the early 2000s, she assured the media that she would wait till 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

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.

8. Shia LaBeouf

In an interview with Playboy Magazine, Shia LaBeouf retailed his first time having sex. 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." Although LaBeouf's recollection may sound awkward and self-deprecating, the actor assured readers that he went on to date the same girl and had a lot more practice with her in the future.

9. Nick Cannon

Nick Cannon's marriage to Mariah Carrey wasn't his first experience with an older woman. 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.

10. Ashton Kutcher

During his interview with Details, 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. In an act of redemption, Kutcher had sex with the same girl again to prove how much his stamina had improved since his first time.

11. 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.

12. Jason Segel

During a press tour for Despicable Me (of all places, of all movies), 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.

13. Chris Evans

Would your teen self ever have been okay with your mother knowing about your sex life? Chris Evans sure didn't mind. According to his interview with Details, Evans rushed home after losing his virginity and proclaimed, "Mom, I just had sex! Where's the clit?" For anyone else, this would be the most horrifying utterance that could come out of your mouth to your own mother. But for Evans, it's just another weekly conversation. Apparently Evans and his mother are very open when discussing his sex life. The actor has admitted to often calling up his mom when he develops an attraction to a new girl, and he will always ask for her personal opinions.

14. Russell Brand

In his autobiography My Booky Wooky By Russell Brand, the comedian and actor detailed his first sexual experience. In true Brand fashion, his story recounted a night filled with debauchery in Hong Kong, which resulted in the loss of his virginity to a prostitute. From his memoir, Brand describes how he visited a sleazy dive bar in Hong Kong with his dad. The father and son then took three prostitutes back with them to their hotel room. Brand recalled how "back in the hotel [his] dad set about unwrapping his two prostitutes. [He] sat on the edge of the other twin bed. She must have known [he] was a virgin as soon as the bungling encounter commenced." Unsurprisingly, that wasn't Brand's last encounter with Hong Kong prostitutes. His book goes on to tell that he "had sex with loads more prostitutes, never wore a condom and never fell in love." Charming.

15. Anthony Kiedis

Like Russell Brand, Red Hot Chili Peppers frontman Anthony Kiedis also lost his virginity to a prostitute while out with his dad. In fact, Kiedis actually shared the same prostitute his dad had frequently spent nights with. According to Kiedis' ghostwriter of his autobiography Scar Tissue, the musician accompanied his father to a bar where his young girlfriend was dancing. At age 12, Kiedis asked his dad for permission to have his first sexual experience with his girlfriend. His dad, Blackie's, response? "Sure, son." Blackie then arranged some mattresses for Kiedis and his girlfriend to do the deed.

16. Nicole Polizzi

On an episode of MTV's Virgin Territory, 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. The solution? The two wrapped his penis in saran wrap. Snooki wasn't particularly proud of the moment and wishes she waited for her current fiancé.

17. Steven Tyler

In an interview with Elle magazine, Steven Tyler, lead singer of Aerosmith, took the opportunity to tell readers how his first sexual encounter was with twins, at age 7. Tyler recalled sitting next to the French twins during church choir. What followed was a threesome that no one needed a mental image of. In fact, no one wanted to imagine Steven Tyler having sex in general. But nevertheless, Tyler always makes a point of illustrating the image for us anyway. Elle readers weren't particularly pleased with Tyler's cheekiness regarding the memory, and they were sure to let him know on the website's comments section.

18. Matthew Fox

Known as the studly Jack Shepard on Lost, Matthew Fox's first time was equally bewildering as his time on the island. According to Fox, he was 12 years old at the time. Although it wasn't the girl's first time, Fox recalls very much being an awkward virgin. The memory isn't as fond as Fox anticipated it would be. He described the image, stating: "It happened literally on the ground by a river while a rodeo was going on in town. It was absolutely terrible and awkward - just two f*cking kids lying down and pulling our pants down."

19. Dustin Hoffman

The Graduate wasn't exactly all fiction for Dustin Hoffman. The acclaimed actor had his own Mrs. Robinson experience when he lost his virginity, at age 15, to an older woman in the school library. Hoffman has attributed the experience to his love of libraries and is quite fond of the memory. The story gets weirder when you find out that the woman actually thought Hoffman was his older brother. Whoops.

20. Matthew Morrison

In an interview for Details, Matthew Morrison discussed how he didn't lose his virginity until he was 21. According to the Glee star, Morrison remained celibate for so long because he was in a long-term relationship with a religious girl. He also joined a Bible study group in college, which helped maintain his good boy image. As one of the only eligible straight men in musical theater at NYU, Morrison began attracting a lot of attention. He's quoted saying, "As a straight guy I had some room. There were the shared interests in singing and dancing, and I always find dancing with someone very evocative and sexual. I definitely hooked up with a lot of girls when I was a young guy on Broadway." Looks like it didn't take long for Morrison to shed his chaise lifestyle.

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