15 Celebs Who Had The WORST Time Losing Their V-Card

Everyone's experience when losing their virginity for the first time is going to be different. It can be awkward, funny, romantic, painful, terrifying or an out of this world bonding experience. Let's be honest - as adults, most of us have been through it and whether or not in our youth we choose to lie about how that experience was at the time, as adults we tend to open up about it a little more.

Celebrities are often willing to share a lot of their own private lives with the public and when asked the question, "How was your first time?" there have been mixed reviews from them. Some thoroughly had the best time of their lives, Harry Potter star Daniel Radcliffe revealed, "I'm one of the few people who seem to have had a really good first time. It was with somebody I'd gotten to know well. It wasn't as horrendously embarrassing as a lot of other people's were - like my friend who got drunk and did it with a stranger under a bridge." Whereas others were more extreme as Angelina Jolie revealed she had used knives to draw blood from her partner during the first time - we'll just leave that for now.

Then sadly for others, they had just the worst time. You can put it down to either having zero experience, not picking the right partner or rushing into things too quickly - but for these following celebrities, they probably wish they could turn back time.

15 Khloe Kardashian 

The Kardashian family have never treated their love life as a taboo subject and Khloe is not afraid to discuss her private life either. She told Belgium news station HLN that losing her virginity was "not a good situation." The reality star revealed, "I was 14 years old and dating an 18-year-old boy, which now I look back and think it's disgusting, but then I thought I was really cool. Basically, I got pressured into having sex. I wasn't ready. I barely knew my own body. I felt like if I didn't, I wouldn't be cool or this guy wouldn't want to talk to me anymore."

She added, "I should have listened to my parents. Don't let anyone pressure you, it's not worth it and how I felt afterward." Hopefully, her younger sisters, Kendall and Kylie Jenner, took her advice and saved themselves for someone special.

14 Lil Wayne 

Rapper Lil Wayne, born Dwayne Michael Carter Jr., is no stranger to the ladies nowadays and it's no surprise he can turn on the charm as he lost his "V-card" aged just 11-years-old. During an interview with Playboy magazine, he revealed, "I was 11 and the girl was 13. I liked board games. We was playing Win Lose or Draw and on the board, she wrote, 'F**k me.' Now I was 11, and I didn't even know it meant 'intercourse.' I just knew it was a cuss word, so I was like, 'Why is she cussing herself out?'"

He continued, "She said, 'Do you want to play Press Your Luck? Well, the game is in my closet.' She had a walk-in closet, so she said, 'Go get it, it's right to the right… ' When I walk to the closet she came in and cut the lights off and took off my pants, and I remember my a** was cold up against the wall. I was like, 'What the hell!?' When I tried to push her off me, I felt that she was naked also, so I just stepped back and let her do what she do." All that at just 11-years-old, we're surprised he doesn't just cower away from women now.

13 Shia LaBeouf 

Shia LaBeouf has always had the acting bug - even from a young age when he tried to pull a confidence trick as a teenager so he could have his way with the ladies. He told Playboy, "For some reason, I was trying to portray myself as a man who had (had been with girls) many times in the past. I didn't tell the girl I was a virgin. I was all, 'Don't worry, babe. I'm gonna handle it tonight.' And meanwhile, I was shaking in my boots."

The Transformers star managed to keep his act together long enough for them to actually make it to the bedroom. He continued, "Getting naked was very strange. It was the first time I'd been naked in the light, in front of a girl, with no hiding place. I remember putting a pillow underneath her because I had seen that in (an adult movie). (It) put her at a weird angle, where I couldn't get in correctly. I'm not extremely well-endowed… and clearly, this wasn't the move." Well, you know what they say - fake it till you make it.

12 Nick Cannon 

Nick Cannon walked down the aisle with Mariah Carey in 2008. The pair welcomed two children into the world, twins Morrocan and Monroe, before they eventually split - all on good terms - in 2015. Mariah is 11 years his senior and it turns out that Nick has always had a thing for the older women.

The America's Got Talent host revealed on Lopez Tonight that his first time with an older woman left him in tears - and it wasn't with Mariah. He said when he was 12-years-old he ended up sleeping with a 14-year-old girl. He explained, "I said we should change positions, she was like 'just get off me!' She ran into the bathroom with all of her friends and they were in there laughing. I vowed from that day forward no woman would ever laugh at me in the sack again. I actually ended up crying at the end of the whole ordeal."

11 P. Diddy

American rapper and record producer P. Diddy, real name Sean Combs, had a tough time growing up. He was just 3-years-old when his father, an associate of convicted drug kingpin Frank Lucas, was killed whilst sitting in his car and P. Diddy was left without a father figure in his life.

This might explain why he was tempted to lose his virginity at the shocking age of just 7-years-old. He told Playboy, "I tried to lose my virginity when I was seven years old. I was on top of a girl who was 9 or 10." But he explained his attempts were a failure (probably because the children had no idea what they were doing or that it was wrong.) Despite his shockingly early start, this did not put him off. He continued, "(I lost it) when I was 13. In the Bronx, you could get a hotel (room) for an hour. I always had $20 or $30 to take a chick to a hotel." We would like to think when he was dating J-Lo he had to up his game to more than a $30 hotel.

10 Britney Spears 

During the early 2000s, Britney Spears was the poster girl for virginity and when she began dating Justin Timberlake everyone was under the impression she had "waited" for him. Then the shock news hit the stands - Britney had actually lost her virginity aged just 14-years-old to a high school football stud.

Her mother Lynne Spears told the world all about it in her book Through The Storm. She wrote about her daughter, "(Britney) lost her virginity a while ago - and I should know" and also added that Justin was misled by her daughter. To add to the heartbreak of her mother's betrayal, Britney was dumped by Justin - the love of her life - not long after the scandal broke. During an interview with Diane Sawyer on ABC when Britney was asked about Justin, she broke down in tears and started sobbing "Oh my god." Our heart goes out to you, Britney.

9 Paris Hilton 

As teenagers, we like to think that we're being a lot smarter than we actually are. Socialite and reality television star Paris Hilton wasn't a famous name at 15-years-old but she was a well-known one. Which meant checking into a hotel with then-boyfriend, 17-year-old boyfriend Randy Spelling, almost impossible and embarrassingly ended with her own grandmother getting involved.

Spelling told New York Daily News, "(Me and Paris) went to Palm Springs once for the weekend, and we couldn't check into the hotel under her name because her grandma was looking for her." After giving a fake name the pair finally got down to it, but Spelling continued, "And what do you know, 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. We broke up like a week later." Sorry, but we'd rather run across a golf course in a dress than have to face our own grandmothers.

8 Snooki 

Our hearts go out to former Jersey Shore cast member Snooki who had her heart broken right after her first time. She told Your Tango, "I was 14. I mean, in upstate New York there's really nothing to do up there but experiment. He was a senior, and I thought he liked me but turned out he was just a jerk. So, it was terrible."

Now she's older, the reality star has certainly worked men out better after being in relationships with fellow cast members Emilio Masella and Justin O. She has also had brief encounters on a night out or casual hookups with Dennis Figueroa, Jeff Miranda, Vinny Guadagnino and Mike 'The Situation' Sorrentino. However, since 2012, she has settled down with Jionni LaVelle and the two had a baby son together, Lorenzo. She told People magazine, "Lorenzo has made me a better person. I'm so much more mature. He's just my life."

7 Ashton Kutcher 

Ashton Kutcher looks like he's been a confident playboy all his life but even he experienced an awkward teenage phase. He revealed during an interview with The Frisky, "I was 15 (when he lost his virginity). It was out in the woods with a girl I had just met who my buddy set me up with. The whole thing lasted two seconds. It was really awkward. Two years later, I had sex with her again just to show her the first performance was a fluke and I'd gotten better." Well, at least he went back to prove his point.

After his divorce from actress Demi Moore, Kutcher fell in love with his former That 70s Show co-star Mila Kunis - although it was supposed to be 'no strings attached.' Kunis revealed on The Howard Stern Show, "We started dating with the idea we're both never going to get married. (He) just got out of a marriage. I got out of a long relationship. I was single and having the best time ever. I was totally dating, having a great time, and I was like, 'I'm never getting married.' He's like, 'Great, neither am I!' And we're like shaking hands on it and we're like, 'Life is great!' A year later, we're like, 'Tomorrow, let's get married.'"

6 Krysten Ritter 

After hit roles in both Breaking Bad and Marvel's Jessica Jones, actress Krysten Ritter has become and international sex symbol. But when she was much younger she doesn't remember the act of love making being one she would rush back to in a hurry.

She told Playboy magazine, "He was a real bad boy. He gave me a school picture that year that said, 'OK, Krysten, I love you. You give me a boner.' That's how we started dating. His name was Damian, but my parents called him 'Demon.'" Jones has played a number of characters who have fallen for bad boys and clearly she could easily take from her own life experience. She added, "Our first time was in his parents' van before basketball practice. I don't remember it being very pleasant." See that's why ladies - you should always leave the bad boys behind.

5 Robin Thicke

Robin Thicke is known for his promiscuity, especially since he dropped his sexually-charged track Blurred Lines in 2013. When asked by Elle magazine what the worst thing about losing his virginity aged just 13-years-old was, he candidly replied, "Make it last longer than 30 seconds." We're unsure how much of a stud he expected to be when underage and getting up to no good.

Just one year after this incident, he met his girlfriend and future wife, Paula Patton, at an under 21s nightclub. They later divorced after 21 years of marriage, following a photo leak showing images of him grabbing a fan's behind in an elevator. Thicke tried to win back his ex-wife with an album called titled Paula - but the album was an international flop and so was his future love life.

4 Matthew Fox 

Following his huge success with the hit TV series Lost, actor Matthew Fox became an international heartthrob and women swooned after him everywhere. Although he ended up batting them off with a stick as he has been happily married since 1992 to his wife, Italian-born Margherita Ronchi.

Before his wife, he learned the easy way that love can be a really awkward thing. He told Playboy magazine, "I was 12. She was about two years older than me. It wasn't her first time. I can actually see the event in my mind's eye, like photographs." He added, "It was in Dubois, Wyoming, where the population sign probably says, to this day, about 1,000. 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 kids lying down and pulling our pants down."

3 Kelly Osbourne

Kelly Osbourne comes from a very laid back and liberal family. Born in London, she has one older sister Aimee and a younger brother Jack. Alongside her parents, Ozzy and Sharon, they are one of the most recognizable families in the world. Kelly grew up

Kelly grew up traveling with her father as he went on tour and throughout her childhood she lived in more than 20 different homes. So meeting people was not a problem - it was just the consequences afterward. She told US Weekly that she lost her V-card age just 13-years-old and was frightened she had fallen pregnant. The Fashion Police queen said, "I convinced myself I was pregnant. I hadn't even gotten my period (yet)." Pregnancy scares are the worst but at so young it's tough to imagine how scary that must have been.

2 Sarah Silverman 

Almost everyone's first encounter was likely embarrassing but for comedian Sarah Silverman it's a moment she'll never be able to look back on without a red face. Known for being outspoken and controversial she told Rookie magazine, "My senior year of high school I visited my sister at Boston University, and she fixed me up with a friend who was from all accounts very good-looking. He put on a condom and pushed against me. I figured that was it. When he finally gave up, he said, 'It's not like it is in the movies, Sarah.'"

Then when she did actually lose her virginity a year later, she wasn't aware this was her first time - not second. She explained that after her real first time finished, "(Kevin - the guy she was with) put out his cigarette and pulled back the sheets to get up, revealing a pattern. Like a red butterfly stamp, getting lighter and lighter with each imprint. There was a moment of long pause, broken by him: 'It's OK. Just buy me new sheets.'" Nothing worse is there, ladies?

1 Russell Brand

Russell Brand, who was also the one-time husband of Katy Perry, had quite the traumatizing moment losing his virginity. Not only was he a young teenager who was pressured into bed with prostitutes in the Philippines but they were also supplied by his own father.

In his tell-all book My Booky Wook, he wrote, "On day one we went to some sleazy dive. Before long I was sat on a bar stool with a Filipino called Mary-Lou. Then we were leaving in a cab with three Asian prostitutes my dad was drunkenly herding." He continued, "Back in the hotel my dad set about unwrapping his two prostitutes. I sat on the edge of the other twin bed. She must have known I was a virgin as soon as the bungling encounter commenced."

Following recovery from drug dependency and a treatment for sex addiction, Brand has now settled with his current partner and together they have one newborn child together.