No matter how the experience goes, it is hard to forget your first time hanging out in bed with another person… if you know what we mean. Activities in the bedroom are always prone to some moments that we regret, much less the first time! For half of our list, they have moments that you are going to pray never happen to you. Whether it’s Shia LaBeouf who talks about the issues his self-admitted small “Transformer” caused, Nick Cannon who ended up crying as girls laughed at him, or Ashton Kutcher who was only able to throw down for 2 seconds of pleasure; there are plenty of reasons as to why these stars regret how it went down.
For the other half on the list, you’ll be happy to know that they’re able to proudly say they have no regrets with how their first booty-bumping went. Jessica Alba, Megan Fox, and Kim Kardashian may have some moments they’d change in real life, but how they lost their virginity is not one of them.
Then, of course, we have some hilarious stories like Charlie Sheen losing his card to a “lady of the night” at the age of 15, Jason Segel lying about writing an Elton John song and even Daniel Radcliffe tells us about how it went when he first used his wand.
An intimate list like this deserves the personal touch that only the celebrities’ words can have, so sit back as celebrities tell their tale in their own words (alongside a joke or two from myself) from every entry as we tackle “Loved or Hated: 20 Celebrities Reveal Their First Time In Bed”.
20. Loved – Daniel Radcliffe: Had Better Since, But Not Embarrassed
Now if we are going to be fair, it sounds like Daniel Radcliffe enjoyed his first time so much because one of his friends seems to have had a horrible go of it,
“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 very well. I’m happy to say I’ve had a lot better sex since then, but 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,” he said in a past interview.
Like drunk and under a bridge? Are you serious? If that’s your barometer, no wonder your first time was really good! Though we’re glad to see that Potter has gotten significantly better at using his wand since his first go-around.
19. Hated – Krysten Ritter: He Gave Her A Picture Saying She Aroused Him
Krysten Ritter may act like a badass on Breaking Bad, but perhaps she nailed the role because she had her bedroom bumped for the first time from a self-described bad boy.
“He was a real bad boy. He gave me a school picture that year that said, ‘OK, Krysten, I love you. You give me [an erection]’ That’s how we started dating. His name was Damian, but my parents called him ‘Demon’. Our first time was in his parents’ van before basketball practice. I don’t remember it being very pleasant,” she said in a past interview.
Looks like Jesse telling Jane that she makes him “pitch a tent” wouldn’t have been that different from her real life experiences! Let’s hope nobody called her ‘bitch’.
18. Loved – Jason Segel: Learned To Play The Piano
If you’re sitting at home and wondering what it is you can do to try and pick up women, learning an instrument is definitely a method that has worked for many men. And while Jason Segel may be better known for his sense of humor than his musical talent, it was his desire to get it on that helped him find his inner Elton!
“I taught myself to play the piano when I was 17 to pick up girls… the first thing I did was I found a really not-that-intelligent girl and I told her that I wrote ‘Your Song,’ by Elton John. I was like, ‘I wrote this for you.’ And then I lost my virginity,” he said in a past interview.
17. Hated – Nick Cannon: Had Several Girls Laugh At Him
“We were in a sleeping bag… 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,” he said in a past interview.
16. Loved – Megan Fox: It Actually Wasn’t Awkward
No matter how many times you have sex, awkward sex is just going to be part of your life. Perhaps you had too many nachos for dinner, drank too much beer or just weren’t feeling on your game. You just have to hope that you and your lover are able to roll with the punches! Megan Fox definitely knows that feeling well, but thankfully she didn’t experience any awkwardness on her first bounce in the sack,
“I’ve had plenty of awkward sex, but that first time was not awkward. I was in love with him and it was nice,” she said in a past interview.
15. Hated – Paris Hilton: Ended With Her Running From Grandma
You can understand that Paris Hilton probably has plenty of sexual experiences that she wishes she could take back. Or you know, some that she wishes she could have had the camera off for. One moment she wishes she could do differently? When she elected to lose her V-Card and her Grandma played the spoiler card! The story below was dictated by Randy Spelling who was allegedly the one who first slept with Hilton,
“We 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. She was, like, 15; I was 17. 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.”
14. Loved – Matthew Morrison: Plenty Of Opportunity With Theater Girls
Matthew Morrison is not only known for his time on the show Glee but also his numerous performances in Broadway and Off-Broadway productions. When he was first starting to break into the industry, he quickly realized that he was one of few straight men around, and you better believe that played a factor into him getting it on!
“There was so much opportunity. There were all these beautiful, beautiful dancers. 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. It was exciting. Very joyous and free, ” he admitted in a past interview.
13. Hated – Khloe Kardashian: Turned Her Off For 3 Years
Not only did Khloe Kardashian not enjoy the first time she got down and dirty, but it literally turned her off intimacy for several years.
“I felt like if I didn’t, I wouldn’t be cool or this guy wouldn’t want to talk to me anymore… I didn’t have sex for the next three years,” she said when talking in a past interview.
Kardashian went on to say,
“My situation was not a good situation. 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.”
We can only hope that by the next time Khloe welcomed someone to her bed, that she was in a much more confident place!
12. Loved – Kim: Talked To Mom And Got Protection
Kim‘s sister Khloe may have had herself a terrible time, but that was definitely not the case for Kim who relied on openness with her mother to make for a smoother time,
“When I did want to have sex the first time I was almost 15… I was like, ‘I think I’m going to, or I want to,’ and she [Kris] was like, ‘OK, so this is what we’re going to do, we’re going to put you on birth control,’ and she was, like, really open and honest with me,” she said in a past interview.
While many people find very valid reasons to hate on the Kardashians, at least Kim was put in a position where she was well-informed of her sexual health and took the proper precautions. We can hope she will do the same with her own children, you know, as well as explain why there are naked photos and videos of mommy all over the internet.
11. Hated – Ashton Kutcher: Gave Her 2 Seconds Of Fun
Ashton Kutcher‘s character on That ’70s Show refers to himself as the Apollo Rocket of Love, but that was far from Kutcher’s real life experience with a lady.
“I was 15. 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,” he admitted to a past interviewer. It’s definitely never a great thing when you go to get intimate with a girl and the entire session lasts under one song!
You’ll be happy to hear that Kutcher’s story at least ends on a happy note as he went on to say, “Two years later, I had sex with her again just to show her the first performance was a fluke and I’d gotten better.”
Kudos to him for finding a way to convince her to sleep with him again!
10. Loved – Jessica Alba: Lost It To Her (Now Ex) Fiancé
Jessica Alba definitely seems like someone who makes smart and responsible decisions with her life. You can imagine that also extends to who she allows herself to get close to and when it came to knocking boots, you better believe she cared deeply about him.
“I didn’t really [seriously] go out with any guys until I was 18 and met my ex-fiancé, Michael Weatherly… It just didn’t work out. I was so young, 18, when I started dating him. I was a virgin. I knew I wanted to be in love with the first person I slept with, because for almost everyone I knew, the first experience made them feel like shit. So I wanted to be really careful that he was going to be in love with me and wasn’t just going to leave me,” she said in a past interview.
The two had met during the filming of Dark Angel.
9. Hated – Snookie: Dude Was a Jerk
Snookie has spent part of her life surrounded by jerks at the Jersey Shore and has definitely rubbed some people the wrong way. But when she was only 14 years old she claims it was just the other person being a jerk and not her,
“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.”
Though if we’re being fair, literally the only thing to do in upstate New York is to have sex? Clearly either Snookie needed to get out more or they needed to work on their tourist department.
8. Loved – Beyonce: Booty Bumped With Jay-Z
Beyonce may know how to shake it up on the stage, but don’t think that’s because she has plenty of experience shaking it up in the bedroom. When talking about her past relationships, Beyonce said,
“People would be surprised as to the lack of experiences I’ve had. When I was 12, 13, I had my first boyfriend, and he was my boyfriend till I was 17… I was too young for it to really be a boyfriend— we didn’t live together, we didn’t, you know…,” with the last sentence implying doing the deed.
Beyonce then went on to say that Jay-Z was the only other boyfriend that she has had. While we don’t know the details on their first night in the sack together, you can imagine it was at least good enough for him to put a ring on her finger! (…Sorry if that’s in your head now.)
7. Hated – Lena Dunham: Best Friend Walked In Crying
When you are experiencing any physicality with your partner, much less the first time, you probably aren’t going to be expecting any of your friends to be stopping by. But as you’ll learn from Lena Dunham, there was no privacy to be found when she was punching her V-Card.
“[My best friend] Audrey headed back to my room hopeful for a sleepover. She was sobbing, and disoriented, and also pretty sure I was alone finishing the cheese, so she flung my door open without knocking. There she found [the guy I was losing my virginity to] Jonah on top of me doing what grown-ups do. She understood the magnitude of the occasion and through her tears shouted, ‘Mazel tov!'”, she said in a past interview.
So not only did Dunham have her friend barge in, but she was even crying. Talk about a double whammy! Dunham also admitted in the interview that she did not tell her partner that she was a virgin prior to the session, but that she could not wait to tell her mom all about it.
6. Loved – John Stamos: “She Dropped Her Keys On My Lap!”
While not everyone out there is still friends with the person they lost their card to, Stamos is lucky enough (or is she the lucky one) to get to say that he is. But to be fair, who is going to STOP trying to be friends with Uncle Jesse? But long before Jesse, it was a set of car keys that started him along his sexual journey.
“I think I was almost 18, and none of my friends had really done it yet. I wasn’t a geeky kid, but I was sort of… innocent. And then I was driving home with the sister of the bass player from my high school band, and she dropped her keys in my lap— my crotch area— and went to grab ’em. And I thought, ‘Oh. This might be on!'”
Stamos went on to say, “She was this beautiful woman who was maybe five to seven years older than me. So we went to her house, and she was very gentle, and easy, and walked me through it. And it was fantastic! We’re still friends.”
5. Hated – Brooke Shields: Ran Down The Hall Naked After
When Brooke Shields wrote about her life in the memoir There Was a Little Girl: The Real Story of my Mother and Me one of the most compelling areas was her relationship with fellow celebrity Dean Cain. The two dated in their 20s and when Shields was 22, she lost her virginity to Cain, but as you can tell from our heading it was not an entirely positive time.
“It should have been what I had wished for myself, but in an instant, guilt slapped me in the face. I got so overwhelmed that I jumped out of my bed. I was buck naked, streaking down a hallway and running as if I had just stolen someone’s wallet. What a sight! Dean leapt up and ran after me with the comforter in his arms. He threw it around me, grabbed me around my shoulders and stopped me from running,” she wrote.
Call us crazy, but ending the session in tears as you run away is definitely not what you are hoping for!
When Cain was asked about his opinion on the story and taking Shields’ virginity, he responded “[she gave it willingly]… I mean, we were in love. She was a wonderful girl,” so at least you know everything ended amicably!
4. Loved – Charlie Sheen: Lost It To A “Lady Of The Night”
While there are some celebrities out there who may consider losing their virginity to a lady of the night to not be a positive, are you really surprised that Charlie Sheen loved it? Sheen was 15 years old when he stole his father’s (fellow actor Martin Sheen) credit card and called up Friendly Introductions LLC.
Sheen was partying with his fellow 15-year-old cousin Joey, who also got in on the action.
“I told Joey, ‘Look, this is my dad’s credit card, you’re going second. He was thrilled. He didn’t give a s**t. I remember having the greatest night of my life,” he said in a past interview.
Sheen later admitted that Martin figured it out when he looked at the credit card bill and saw the charges. Though while you may expect discipline, Sheen said “His whole concern was that I didn’t mistake that for love. I’m still trying to process that one.”
It definitely was the start of a long love of escorts for Sheen.
3. Hated – Ansel Elgort: Set The Mood With Fluorescent Lighting
Ansel Elgort is both a talented actor and musician, so you can imagine he has several tools at his disposal for when trying to woo over a lady love. But when he was 14 years old and knocking boots for the first time, he admitted that he was in completely over his head saying,
“I had no clue what I was doing, and neither did the girl. I didn’t even make the lighting good. That’d be one thing I’d do differently. It was, like, fluorescent, bright bedroom light, like, over the covers.”
2. Loved – Sienna Miller: Mom Made Sure She Did It At Home
Above you read about how Krysten Ritter had to get down and dirty in a van, but that was not the case for Sienna Miller.
“I had my first serious boyfriend when I was 16 and my mother made sure I brought him home. She didn’t want me doing it outside and would say, ‘I’d rather you did it in my house if you’re going to do it at all’,” she said in a past interview.
You can imagine that Miller’s mom also made sure she took the necessary steps to ensure protection was used. This is definitely a far better stance than just pretending sex isn’t a thing! Sienna Miller recently admitted to spending nine hours filming bedroom scenes with Ben Affleck for Live By Night but you can imagine her first time wasn’t nearly that long!
1. Hated – Shia LaBeouf: Admits His Johnson Is Small
Shia LaBeouf made several key errors when it came to shaking his booty for the first time. All of which he highlighted in a past interview,
“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,” definitely a rough start. Good luck asking for pointers. He went on to say,
“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 a movie,” mistake number two, don’t use adult entertainment as a starting guide! Especially because he went on to say,
“[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.”
Lied about virginity, couldn’t complete the transaction AND admitted to having a tiny penis? No wonder LaBeouf ends this list!