The Virginity Loss Stories Of 15 Hollywood A-Listers

It’s a fact of life. You’re either a virgin or you aren’t. It’s the transitionary period that’s interesting. While we’ve all had our ups and downs in the bedroom, we can all admit that the first time is never quite as dreamy or as easy as the movies make it seem. Rest assured, though, that movie stars and other celebrities go through similarly sticky situations. Here are fifteen stories from fifteen Hollywood hotshots about how they popped the cherry.

Paris Hilton

Leave it the heiress of the Hilton empire to lose her virginity at a luxury resort in Palm Springs. And not just to any old schmuck either, but to Randy Spelling, the younger brother of Tori Spelling. Paris was fifteen years old at the time and even then had more money than any person should.

Ashton Kutcher

Kutcher is man enough to admit that his first experience with sex was the worst. Apparently, after being set up with a girl by a buddy of his, the pair snuck off into the woods for a quickie that lasted about four seconds and was super awkward. The two hooked up again a few years later so that Ashton could prove he had gotten much better.

Chris Brown

Believe what you want about Breezy, but this one sounds a little fishy. Brown reportedly told an interviewer that he lost his virginity to a fourteen year old girl when he himself was only eight. We’re not quite sure what to make of this one, but the hip-hop star seemed sincere, so take what you will from that exchange.

Katy Perry

The infamous “I Kissed a Girl” songstress was more than happy to kiss a boy or two back before her rise to fame. Katy revealed that she lost her virginity in the front seat of a Volvo Sedan while Jeff Buckley’s romantic ballad “Grace” played over the car radio.

Jessica Simpson

In a very public and highly televised affair, Simpson was fairly open about not wanting to have sex before marriage. When she did finally marry her first husband (now ex) Nick Lachey at the age of twenty-two, the pair got in on and the rest is history.

Johnny Depp

Thirteen years old and in the back of a car. Yup. No kidding, you guys. While still rocking out as a member of the band The Flame, a (very) young Johnny Depp found himself deflowered in the backseat of his friend’s car when he was barely pubescent. This, of course, was long before he became a global sex symbol.

Jason Segel

Gentlemen, take note. Chicks always go for a guy with an instrument. At the age of seventeen, Segel taught himself to play piano in an effort to pick up some ladies. He then found a less-than-bright young woman and convinced her that he’d written Elton John’s “Your Song” for her before promptly losing his v-card. Nicely done!

Kirsten Dunst

Give the girl a medal for waiting to do it with someone special! Kirsten reportedly lost her virginity to her boyfriend of two years Jake Gyllenhaal. After a very public relationship, the pair split fairly amicably as far as Hollywood break-ups go.

Taylor Swift

Sigh. Oh, T-Swizzle. Whatever will we do with you? Taylor Swift also lost her virginity to Jake Gyllenhaal, though the two barely dated for more than a few months and Taylor had only just finished high school when she began seeing the thirty-something Gyllenhaal. Smooth, guys. Real smooth.

Kim Kardashian

Someone has got to give mad props to the reality television star for stepping up and talking to Mom first. At fourteen, Kim was thinking very seriously about taking the next step with her high school boyfriend when she pulled her mother into the bathroom to ask about going on birth control.

John Stamos

We all wish we lost our virginity the way Stamos lost his. At the age of eighteen, he was hanging out with the older early-twenties age sister of a high school bandmate when she dropped her keys in his lap. She then invited him over to do the deed, and they remain great friends decades later!

Russell Brand

This one is absolutely classic Brand. While out to dinner with his dad, Russell writes in his memoir “My Booky Wook”, the father and son duo brought three Asian prostitutes back to the hotel. While dear old dad was busy with two of them, Russell was treated to the full virginity stripping service by the third.

Brooke Shields

Talk about family values. Brooke Shields revealed that she lost her virginity to fellow actor Dean Cain, but immediately regretted it. It seems a few parental issues got in the way when Brooke realized that she was not able to handle the idea of loving someone more than she loved her own mother.

Britney Spears

The seemingly innocent America’s sweetheart of the late 1990’s and early 2000’s turned out not to be quite the pop princess darling the media made her out to be. Britney’s own mother revealed that at the age of fourteen, Britney lost her virginity to her eighteen-year-old football player boyfriend. Thanks, Mom!

Angelina Jolie

Listen. We’ve all tried some weird stuff, just for the hell of it. Angelina Jolie, though, takes the cake. She confessed that, in an effort to gain emotional closeness to her boyfriend, she held a knife to him and cut him before also cutting herself and exchanging blood. Whatever floats your boat, Angie.