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Ex Playboy Bunny opens up about the one 'disgusting' sex act with Hugh Hefner that still horrifies her

Home> Celebrity> News

Updated 12:42 22 Nov 2025 GMTPublished 12:41 22 Nov 2025 GMT

Ex Playboy Bunny opens up about the one 'disgusting' sex act with Hugh Hefner that still horrifies her

She explained what it was like dating Hugh Hefner

Gerrard Kaonga

Gerrard Kaonga

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Featured Image Credit: Ethan Miller/Getty Images for BASE Entertainment

Topics: Hugh Hefner, Sex and Relationships, Celebrity

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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Holly Madison has opened up about the sex life she used to have with Hugh Hefner and one aspect she 'hated'.

The model was in a relationship with Playboy founder Hefner from 2001 to 2008.

Despite the 53-year age gap between the two, Madison said they had a very active sex life and has regularly shared NSFW insights.

She has often spoken about the good and bad of living in the Playboy Mansion, as well as her relationship with the late magazine publisher.

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Hefner passed away at the age of 91 on September 27, 2017.

Madison, now 45, made an appearance on an episode of the In Your Dreams podcast in May and opened up about an act she used to find 'disgusting'.

Holly Madison has been candid about her relationship with Hugh Hefner (Denise Truscello/Getty Images for Grant A Gift for Autism)
Holly Madison has been candid about her relationship with Hugh Hefner (Denise Truscello/Getty Images for Grant A Gift for Autism)

Addressing the age gap, she said: “If it was just me and him, it was a lot more normal than you would think.”

But Madison went on to say that she 'hated' having group sex with Hefner and other individuals.

She explained: “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.”

While on the podcast, Madison also touched on the mockery and trolling she faced on social media because of her relationship with Hefner.

She said: “There was a time when I couldn't post anything [on social media] without some dumba** in the comments [being] like, 'Oh, old balls.'”

Madison then joked: “Maybe some people's balls do get old and nasty, but I've never seen such a thing.”

However, she did go on to say the pair would often keep the lights off and brought up the phrase, 'all cats are gray in the dark'.

The pair dated from 2001 to 2008 (Chad Buchanan/Getty Images)
The pair dated from 2001 to 2008 (Chad Buchanan/Getty Images)

Despite things getting on fine in the bedroom, Madison has also previously reflected on the mental aspect of her relationship with Hefner.

Speaking in hindsight, she noted that she 'didn’t actually know him that well' despite doing things she thought were connecting them.

In an interview with the New York Post, the Holly's World star admitted: “I thought I was connecting with [Hefner], when really I was just somebody who had trouble connecting with people my whole life. And I’d met somebody who was like a master manipulator.”

Looking back, Madison sees herself as 'somebody who was young and impressionable and just kind of in a fog almost'.

  • Hugh Hefner's ex-girlfriend Kendra Wilkinson makes surprising admission about living in Playboy Mansion and having 'sex for money'
  • Bizarre weekly schedule Hugh Hefner had at Playboy mansion as ex-girlfriend Holly Madison details 'disgusting' sex act
  • 10 bizarre rules Hugh Hefner imposed on Playboy girlfriends as ex Holly Madison speaks out on 'disgusting' sex act
  • Hugh Hefner's ex-girlfriend Holly Madison reveals 'disgusting' sex act she 'hated' doing with the late mogul

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