True Stories

Celebrity Virginity Loss Stories That Prove It's Awkward For Everyone  

Ryan Davis
158.4k views 20 items

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.
Angelina Jolie is listed (or ranked) 1 on the list Celebrity Virginity Loss Stories That Prove It's Awkward For Everyone
Photo: Denis Makarenko/Shutterstock
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."

More Angelina Jolie

#73 of 159 on The All-Time Greatest Action Stars #62 of 459 on The Most Beautiful Women Of 2019, Ranked featuring Fun Facts You Didn't Know About Angelina Jolie 14 Twisted Angelina Jolie Stories That Prove There's More To Her Than Meets The Eye

see more on Angelina Jolie
Shia LaBeouf is listed (or ranked) 2 on the list Celebrity Virginity Loss Stories That Prove It's Awkward For Everyone
Photo:  DoD News Features/Wikimedia Commons/CC BY 2.0

In an interview with Playboy Magazine, Shia LaBeouf recalled 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.

More Shia LaBeouf

#5 of 135 on The Best Hot Ones Guests Ever #9 of 21 on Famous People Supposedly Controlled by MK Ultra featuring Shia LaBeouf’s Many Alter Egos, Ranked Whatever Happened To Shia LaBeouf?

see more on Shia LaBeouf
Kim Kardashian is listed (or ranked) 3 on the list Celebrity Virginity Loss Stories That Prove It's Awkward For Everyone
Photo: Beacon/flickr/CC-BY-NC 2.0
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]."

More Kim Kardashian

#86 of 95 on The Most Influential Women of 2019 #9 of 13 on Celebrities Who Took Negative Press And Turned It Positive featuring Here Are All The Celebrities Who Have Fallen Victim To The Kardashian Kurse The Most Extravagant Gifts Kanye West And Kim Kardashian Have Ever Given Each Other

see more on Kim Kardashian
Nick Cannon is listed (or ranked) 4 on the list Celebrity Virginity Loss Stories That Prove It's Awkward For Everyone
Photo:  Alberto Rodriguez/Getty Images
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.

More Nick Cannon

#47 of 54 on The Best Black Actors & Actresses Under 40 #23 of 27 on The Biggest Manwhores in the Entertainment Industry #23 of 30 on A Definitive Ranking of Rappers as Actors #6 of 20 on 20 Famous Celebrities Who Are Also DJs

see more on Nick Cannon