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

·12 min read

1.Chris Evans

  Jason Merritt / Getty Images
Jason Merritt / Getty Images

During a 2017 interview with Esquire, the Marvel actor recalled, "I know I'm going to L.A. in August. So I go home, and that spring I would wake up around noon, saunter into high school just to see my buddies, and we'd go get high in the parking lot. I just fucked off. I lost my virginity that year. 1999 was one of the best years of my life."

  Jeff Kravitz / FilmMagic / Getty Images
Jeff Kravitz / FilmMagic / Getty Images

In an interview on Late Night with Seth Meyers, Chris also shared that after his first sexual experience, he immediately went home to tell his mom.

  NBC
NBC

2.Miley Cyrus

  Steve Granitz / WireImage / Getty Images
Steve Granitz / WireImage / Getty Images

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."

  Matt Winkelmeyer / Getty Images for The Recording Academy
Matt Winkelmeyer / Getty Images for The Recording Academy

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.

  Larry Busacca / Getty Images
Larry Busacca / Getty Images

"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."

  Dia Dipasupil / Getty Images
Dia Dipasupil / Getty Images

3.Dwayne "The Rock" Johnson

  Kevin Winter / Getty Images
Kevin Winter / Getty Images

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.'"

  Tibrina Hobson / Getty Images
Tibrina Hobson / Getty Images

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

  Samir Hussein / Samir Hussein / WireImage
Samir Hussein / Samir Hussein / WireImage

4.Khloé Kardashian

  Matt Winkelmeyer / Getty Images
Matt Winkelmeyer / Getty Images

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."

  Rodin Eckenroth / WireImage / Getty Images
Rodin Eckenroth / WireImage / Getty Images

"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!!!'"

  Kevin Mazur / Getty Images
Kevin Mazur / Getty Images

5.Joe Jonas

  Stephane Cardinale - Corbis / Corbis via Getty Images
Stephane Cardinale - Corbis / Corbis via Getty Images

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."

  Stefanie Keenan / WireImage for Vanity Fair
Stefanie Keenan / WireImage for Vanity Fair

"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."

  Jeff Kravitz / Getty Images
Jeff Kravitz / Getty Images

6.Jessica Alba

  David Livingston / Getty Images
David Livingston / Getty Images

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."

  J. Vespa / WireImage / Getty Images
J. Vespa / WireImage / Getty Images

7.Daniel Radcliffe

  Anthony Harvey / Getty Images
Anthony Harvey / Getty Images

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."

  Karwai Tang / WireImage / Getty Images
Karwai Tang / WireImage / Getty Images

"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."

  Rich Fury / Getty Images for SXSW
Rich Fury / Getty Images for SXSW

8.John Legend

  Charley Gallay / Getty Images
Charley Gallay / Getty Images

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."

  Troy Harvey / ABC via Getty Images
Troy Harvey / ABC via Getty Images

9.Krysten Ritter

  Paul Archuleta / FilmMagic / Getty Images
Paul Archuleta / FilmMagic / Getty Images

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."

  Randy Shropshire / Getty Images
Randy Shropshire / Getty Images

10.Sebastian Stan

  Jamie Mccarthy / Getty Images
Jamie Mccarthy / Getty Images

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.

  Paras Griffin / Getty Images for Roadside Attractions
Paras Griffin / Getty Images for Roadside Attractions

"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."

  Bravo / NBCU Photo Bank / NBCUniversal via Getty Images
Bravo / NBCU Photo Bank / NBCUniversal via Getty Images

11.Kevin Hart

  Roy Rochlin / Getty Images
Roy Rochlin / Getty Images

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."

  Mike Coppola / Getty Images for MTV
Mike Coppola / Getty Images for MTV

12.Jessica Simpson

  John Shearer / Getty Images for Jessica Simpson Collection
John Shearer / Getty Images for Jessica Simpson Collection

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."

  Frank Micelotta / Getty Images
Frank Micelotta / Getty Images

13.Nick Kroll

  Taylor Hill / WireImage / Getty Images
Taylor Hill / WireImage / Getty Images

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.

  TBS
TBS

14.Ed Sheeran

  Thomas Niedermueller / Getty Images
Thomas Niedermueller / Getty Images

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."

  Dave J Hogan / Getty Images
Dave J Hogan / Getty Images

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."

  Jeff Spicer / Getty Images for Universal Pictures International
Jeff Spicer / Getty Images for Universal Pictures International

15.Charlie Puth

  Momodu Mansaray / WireImage / Getty Images
Momodu Mansaray / WireImage / Getty Images

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.'"

  Jc Olivera / Getty Images
Jc Olivera / Getty Images

"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.'"

  Kevin Mazur / Getty Images for iHeartRadio
Kevin Mazur / Getty Images for iHeartRadio

16.Kit Harington

  Jason Laveris / FilmMagic / Getty Images
Jason Laveris / FilmMagic / Getty Images

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."

  David M. Benett / Dave Benett / Getty Images
David M. Benett / Dave Benett / Getty Images

17.Tina Fey

  Dia Dipasupil / Getty Images
Dia Dipasupil / Getty Images

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."

  Jamie Mccarthy / Getty Images for Writers Guild of America, East
Jamie Mccarthy / Getty Images for Writers Guild of America, East

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."

  CBS
CBS

18.Brooke Shields

  John Lamparski / Getty Images
John Lamparski / Getty Images

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."

  Dimitrios Kambouris / Getty Images for Glamour
Dimitrios Kambouris / Getty Images for Glamour

19.Ashton Kutcher

  Jean Baptiste Lacroix / Getty Images
Jean Baptiste Lacroix / Getty Images

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."

  J. Merritt / Getty Images
J. Merritt / Getty Images

20.Kim Kardashian

  Angela Weiss / AFP via Getty Images
Angela Weiss / AFP via Getty Images

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."

  Rodin Eckenroth / WireImage / Getty Images
Rodin Eckenroth / WireImage / Getty Images

21.Adam Lambert

  Frazer Harrison / Getty Images
Frazer Harrison / Getty Images

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."

  J. Merritt / Getty Images for GLAAD
J. Merritt / Getty Images for GLAAD

22.Tamera Mowry-Housley

  Rodin Eckenroth / WireImage / Getty Images
Rodin Eckenroth / WireImage / Getty Images

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.

  HOT 97
HOT 97

23.Lena Dunham

  Vince Bucci / Getty Images for Friendly House
Vince Bucci / Getty Images for Friendly House

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!'"

  Frederick M. Brown / Getty Images
Frederick M. Brown / Getty Images

"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."

  Presley Ann / Getty Images
Presley Ann / Getty Images

24.Megan Fox

  Scott Dudelson / Getty Images
Scott Dudelson / Getty Images

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."

  Han Myung-gu / WireImage / Getty Images
Han Myung-gu / WireImage / Getty Images

25.And finally, Sarah Silverman

  Kevin Winter / Getty Images
Kevin Winter / Getty Images

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.'"

  Tibrina Hobson / WireImage / Getty Images
Tibrina Hobson / WireImage / Getty Images

"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.'"

  Kevin Winter / Getty Images
Kevin Winter / Getty Images

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