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25 Shocking “Sex” Confessions From Celebrities About Their First Sexual Experiences That Are Kinda Wild

1. Chris Evans

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2. Miley Cyrus

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On a 2020 episode of the Call Her Daddy podcast, the singer said, “I was attracted to girls way before I was ever attracted to guys.” She revealed that her first-ever sexual experience was with two women, saying they went “past first base.” Miley didn’t “go all the way with a dude [until] I was 16. But I ended up marrying the guy, so that’s pretty crazy.”

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However, “I lied and said he wasn’t the first so I didn’t seem like a loser,” she revealed. Instead, she told him that she’d hooked up with a friend.

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“I couldn’t think of anyone so I just made somebody up that I knew, but we’d never actually had sex before,” she said. “[Liam’s] friend ended up marrying him, so then [Liam] was like, ‘Now my friend is marrying someone you’ve hooked up with.’ So then, when I was like 24, I had to say that I lied when I was 16.”

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3. Dwayne “The Rock” Johnson

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In 2017, the Jumanji actor told Elle that his first sexual experience was at 14 in a park. “We shouldn’t have been in the park in the first place. All of a sudden, a big spotlight came on us. Bang. You hear the cop roll down the window and say, ‘Ma’am, are you okay? Will you come to the car?’ She gets dressed, comes to the car. They say, ‘Are you being attacked?’ She says, ‘No, that’s my boyfriend.'”

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“It was a complete nightmare,” he said with a laugh. “Some stories are beautiful, but mine was not.”

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4. Khloé Kardashian

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The reality TV star shared a 2016 blog post on her website recalling her first sexual experience. “It’s not funny to lose your virginity! It’s weird and you’re scared and it hurts and you don’t know what will happen. I was 15 and he was an older guy who wasn’t a virgin. I don’t really remember it hurting, but I do remember that I just wanted to get it over with.”

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“You definitely don’t have an orgasm your first time. I didn’t for the first few years! I didn’t even know what the feeling was until I had one; I just liked the intimacy part. When it happened, I was like, ‘Ohhhhh, that’s what that is!!!'”

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5. Joe Jonas

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During a 2016 Reddit AMA, the singer revealed, “I lost my virginity to this girl named Ashley. You can probably just Google it. It’s pretty easy to figure out.”

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“It’s quite the great story,” he continued. “I didn’t have any condoms, so I went to our drummer, Jack’s room, who was my roommate at the time, and I demolished his room looking for them. Found them underneath his underwear drawer. When he came home, he thought somebody broke into his room because his whole room was demolished because I was in dire need. Needed to happen then and now. Safety first, kids.”

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6. Jessica Alba

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In 2005, the actor told Cosmopolitan, “I was so young, 18, when I started dating [Michael Weatherly]. 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.”

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7. Daniel Radcliffe

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During a 2014 interview with Elle, the Harry Potter actor shared, “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.”

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“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.”

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8. John Legend

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During a 2017 interview with Cosmopolitan, he said, “Just being around older people that were having sex, it felt like I had to catch up with everybody. I think a lot pressure when you’re a [cisgender male] teen has to do with losing your virginity and negotiating relationships with women.”

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9. Krysten Ritter

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During a 2017 interview with Playboy, the actor recalled, “He was so angsty and bad. 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.”

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10. Sebastian Stan

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On The Drop-In with Will Malnati podcast, the Marvel actor revealed that his first sexual experience was during his senior year of high school. He lied to his girlfriend and pretended he had more experience in the bedroom.

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“I was so freaked out,” he said. “We rented out a hotel room, did it at the Times Square Hotel, and had a McDonald’s happy meal afterwards. I swear to god. I will not name her, but god bless her — she’s married now.”

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11. Kevin Hart

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In his memoir I Can’t Make This Up: Life Lessons, the comedian wrote, “Her name was Angie. We didn’t go to the same school, but she lived in the neighborhood. The first time, I couldn’t tell whether we did it or not. This time, I was certain we did it. So I double lost my virginity. I had to lose it twice, just to make sure.”

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12. Jessica Simpson

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In her memoir Open Book, the singer wrote, “I’d built up this anticipation in my mind that the first time I had sex with my husband had to be this transcendent experience where the heavens parted. What I didn’t know then is that everyone’s first time is awkward, and that is part of it. And that it’s OK, but at the time, it’s tough to understand.”

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13. Nick Kroll

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On Conan, the Big Mouth actor revealed that his first sexual experience was on Valentine’s Day in college with a friend. “It happened in my sister’s bed,” he added.

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14. Ed Sheeran

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During a 2014 interview with Elle, the singer was asked which felt better: selling out Madison Square Garden three times or having sex for the first time. He replied, “Probably selling out Madison Square Garden.”

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When asked if his first time wasn’t memorable, he responded, “It’s a benchmark in my life, but it wasn’t the best thing I’ve ever done.”

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15. Charlie Puth

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Last week, the singer made headlines for revealing during a Bustle interview that he had sex for the first time with a fan when he was 21. “This girl came up to me and was like, ‘Can you sign my chest?'” he recalled. “I was like, ‘I feel like a rock star.'”

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“I never saw her again,” he continued. “She was lovely, but it makes me sad sometimes because I wish the older version of me was like, ‘Hey, you might want to just make this like a little more memorable.'”

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16. Kit Harington

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In 2017, the Game of Thrones actor told Elle, “It was a typical sort of teenage thing, at a party. I was probably too young. I think the girl and I just kind of wanted to. You either hold on and do it right, or you’re young and decide to get the monkey off your back.”

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17. Tina Fey

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In a 2008 Vanity Fair interview, the 30 Rock actor revealed that she had sex for the first time at 24. “I remember bringing people over in high school to play — that’s how cool I am — that game ‘Celebrity.’ That’s how I successfully remained a virgin well into my 20s, bringing gay boys over to play Celebrity.”

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On the Late Show with David Letterman, David read from an article listing celebrities who had sex for the first time in their twenties. He mentioned Brooke Shields, and Tina said, “She made a choice,” then joked that she couldn’t “give it away.”

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18. Brooke Shields

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During a 2009 interview with Health, the Blue Lagoon actor revealed that she regrets waiting so long to have sex. “I would have lost my virginity earlier than I did at 22. I had the public and all this pressure, and I wish I had just gotten it over with in the beginning when it was sort of OK. I think I would have been much more in touch with myself.”

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19. Ashton Kutcher

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In 2008, the actor told The Frisky, “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. Two years later, I had sex with her again just to show her the first performance was a fluke and I’d gotten better.”

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20. Kim Kardashian

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On a 2012 episode of The Oprah Winfrey Show, the reality TV star revealed that she decided at 14 that she wanted to have sex for the first time with her boyfriend of two years. “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 [Kris Jenner] was like, ‘Okay, so this is what we’re gonna do, we’re gonna put you on birth control,’ and she was like, really open and honest with me.”

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21. Adam Lambert

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In E! True Hollywood Story: Adam Lambert, the singer said, “I lost my virginity at 21, and it was to a man — not a woman. And it wasn’t very good,” he laughed. “Sometimes, it takes a little while to learn how to do that correctly.”

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22. Tamera Mowry-Housley

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On HOT 97, the Sister, Sister actor shared that she had sex for the first time at 29. Then, due to religious reasons, she waited until she was married to have sex again.

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23. Lena Dunham

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In her memoir Not That Kind of Girl: A Young Woman Tells You What She’s “Learned,” the Girls actor wrote, “[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 Jonah on top of me doing what grownups do. She understood the magnitude of the occasion and through her tears shouted, ‘Mazel tov!'”

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“I didn’t tell him I was a virgin, just that I hadn’t done it ‘that much.’ It hurt a little more than I’d expected but in a different way, and he was nervous too, and he never came. Afterwards, we lay there and talked, and I could tell he was a really nice person. I commended myself for making a healthy, albeit hasty, partner choice. I really couldn’t wait to tell my mom.”

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24. Megan Fox

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In 2010, the actor told Cosmopolitan that she had sex for the first time at 17 with her first real boyfriend. “I’ve had plenty of awkward sex, but that first time was not awkward,” she recalled. “I was in love with him, and it was nice.”

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25. And finally, Sarah Silverman

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In her memoir The Bedwetter: Stories of Courage, Redemption, and Pee, the comedian wrote, “Slowly at first, he pushed inside me. All the way inside. And all I could think was, ‘Holy shit, THIS is sex.'”

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“He put out his cigarette and pulled back the sheets to get up, revealing a Rorschach-like pattern of blood. Like a red butterfly stamp, getting lighter and lighter with each imprint. There was a long moment of silence before I worked up the moxie to say, ‘That came out of you.’ ‘Um. No, it didn’t.’ Another long pause, broken by him: ‘It’s okay. Just buy me new sheets.'”

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Do you have a special or funny story about your first sexual experience? LMK in the comments below!