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Hugh Hefner's ex-girlfriend Holly Madison reveals 'disgusting' sex act she 'hated' doing with the late mogul

Home> Celebrity

Updated 17:48 4 May 2025 GMT+1Published 10:24 4 May 2025 GMT+1

Hugh Hefner's ex-girlfriend Holly Madison reveals 'disgusting' sex act she 'hated' doing with the late mogul

The ex-Playboy Bunny has gotten candid about her sexual past with Hefner

Gerrard Kaonga

Gerrard Kaonga

Featured Image Credit: Michael Bezjian/WireImage via Getty Images

Topics: Celebrity, Hugh Hefner, Sex and Relationships

Gerrard Kaonga
Gerrard Kaonga

Gerrard is a Journalist at UNILAD and has dived headfirst into covering everything from breaking global stories to trending entertainment news. He has a bachelors in English Literature from Brunel University and has written across a number of different national and international publications. Most notably the Financial Times, Daily Express, Evening Standard and Newsweek.

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Hugh Hefner’s ex-girlfriend Holly Madison has opened up about the less-than-enjoyable side of dating the Playboy founder.

Madison, now 45, had the ‘privilege’ of being Hefner’s ‘number one girlfriend’ back when she was staying at the Playboy mansion in the 2000s.

While the infamous LA residence was filled with people coming and going, a few women were very clearly mainstays as they were the girlfriends of the late mogul - who passed away aged 91 in 2017.

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One of those women was Madison and following her time on the reality TV show The Girls Next Door, she has opened up about what things were really like, including their sex life.

Holly Madison has opened up about her sex life with Hugh Hefner (Chad Buchanan/Getty Images)
Holly Madison has opened up about her sex life with Hugh Hefner (Chad Buchanan/Getty Images)

Speaking on the In Your Dreams Podcast with Owen Thiele, Madison explained what it was like sharing Hefner with his other girlfriends at the time, Bridget Marquardt and Kendra Wilkinson, as well as the overall experience.

Speaking about the sex, she insisted it was ‘normal’ despite the 50-year age difference between her and Hef but admitted there was one act she hated doing with him.

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She said: “Well, it's a very different story between when we were just by ourselves than with everybody else in the room.

“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.

“If it was just me and him, it was a lot more normal than you would think.”

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Madison also stated that she was previously ridiculed on social media if she ever spoke about her sex life, because of the age gap.

She added: “I think everybody has this real horror story of how gross an old man's body must be.

She said she had normal sex with Hefner despite the significant age difference (Laurence Cottrell/FilmMagic)
She said she had normal sex with Hefner despite the significant age difference (Laurence Cottrell/FilmMagic)

“I feel like there was a time when I couldn't post anything without some dumba** in the comments like, 'Oh, old balls', or something like that and look, maybe some people's balls do get old and nasty, but I've never seen such a thing.”

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Despite having a relatively normal sex life when it was just the two of them, Madison has also opened up about the difficulties of living in the 'fast lane' and the struggles being Hefner’s girlfriend brought her.

Speaking to the Mail Online, she revealed: “When you're involved in a world where you're highly sexualized or sexualizing yourself, and there's a lot of things at stake and things you could possibly gain, like fame, money, opportunities, there's people around you who are jealous of those things. It's truly living life in the fast lane.”

  • Hugh Hefner's ex-girlfriend Kendra Wilkinson describes what she saw during Diddy's infamous parties
  • Former Playboy twins open up about ‘trauma’ they experienced after years in Hugh Hefner's mansion
  • Hugh Hefner's ex-girlfriend Kendra Wilkinson reveals damaging impact their relationship has had on her sex life
  • Hugh Hefner's ex-girlfriend says living in Playboy Mansion was like a 'cult'

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