unilad homepage
unilad homepage
  • News
    • UK News
    • US News
    • World News
    • Crime
    • Health
    • Money
    • Sport
    • Travel
  • Music
  • Technology
  • Film and TV
    • News
    • DC Comics
    • Disney
    • Marvel
    • Netflix
  • Celebrity
  • Politics
  • Advertise
  • Terms
  • Privacy & Cookies
  • LADbible Group
  • LADbible
  • SPORTbible
  • GAMINGbible
  • Tyla
  • UNILAD Tech
  • FOODbible
  • License Our Content
  • About Us & Contact
  • Jobs
  • Latest
  • Archive
  • Topics A-Z
  • Authors
Facebook
Instagram
X
Threads
TikTok
YouTube
Submit Your Content
Hugh Hefner's ex describes 'really weird' group nights with mogul at mansion
Home>Celebrity
Updated 12:23 10 May 2026 GMT+1Published 12:22 10 May 2026 GMT+1

Hugh Hefner's ex describes 'really weird' group nights with mogul at mansion

Anyone getting down at the Playboy Mansion could expect the proceedings to get 'really weird'

William Morgan

William Morgan

google discoverFollow us on Google Discover
Featured Image Credit: Chad Buchanan/Getty Images

Topics: Hugh Hefner, Sex and Relationships

William Morgan
William Morgan

Advert

Advert

Advert

We should all be glad that the walls of the Playboy Mansion can't speak, judging by what one of his former 'playmates' Holly Madison has revealed about her orgies with Hugh Hefner.

The 46-year-old ex girlfriend of the infamous Playboy editor, who died in 2017 at the age of 91, said her group sex parties with Hefner and scores of other women were, unsurprisingly, 'a really weird scene'.

Madison became the Lothario's '#1 Girl' in 2002, when Hefner was in his mid 70s and she was 22 and up to her eyeballs in credit card debt, and stayed with him for around five years while she filmed the E! series The Girls Next Door, which followed her life at the mansion.

Speaking recently on the Let's Be Honest podcast with Kristin Cavallari, Madison detailed what it was really like to be involved in one of Hefner's infamous group sex parties and how exactly half a dozen women get down with a senior.

Advert

Holly Madison was Hefner's main squeeze for around six years (Denise Truscello/WireImage)
Holly Madison was Hefner's main squeeze for around six years (Denise Truscello/WireImage)

She revealed: “Yeah, kind of like taking turns and then the girls who weren’t active with him were kind of like acting like they were active with the other girls, but not really."

With this 'weird' atmosphere, Hefner's ex explained that 'nobody liked it and everybody tried to just get it done as fast as possible.'

And these debaucheries were not just confined to the orgy itself, Madison revealed, Hefner would also be playing pornography on large screens around the room, making the whole scene even stranger.

“It would be kind of silhouetted because you’d have, like, these giant screens of porn going and it would be just girls like talking s–t with each other,” Madison added.

But it was not always group sex parties and bored 'playmates', the reality star told Cavallari that when it was just her and Hefner, the proceedings were 'very suburban.' She said: “(It was) us watching a movie or he’s doing a crossword puzzle, and I’m reading.”

Kendra Wilkinson (L) Bridget Marquardt and Holly Madison (R) were Hefner's main girlfriends (Carlo Allegri/Getty Images)
Kendra Wilkinson (L) Bridget Marquardt and Holly Madison (R) were Hefner's main girlfriends (Carlo Allegri/Getty Images)

At this time, during Hefner's quieter years, Madison was one of just three of his main girlfriends, the other two being Bridget Marquardt and Kendra Wilkinson. But she has often spoken of her discomfort at taking part in the sex parties.

She told the In Your Dreams podcast last year: “Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it."

Madison even described their sex life as 'hell' and 'traumatic', explaining: “He wouldn’t move. He would be like a bump on the log in the middle of the bed."

When her relationship with the then 82-year-old Playboy editor came to an end in 2008, despite Hefner saying 'marriage isn't part of my puzzle' during their relationship, in 2010 he became engaged to Crystal Harris, who had appeared as Playboy's 'Co-ed of the week'.

Although Hefner was 60 years her senior, she remained married to him until his death in 2017.

  • Hugh Hefner's ex Holly Madison reveals the one specific 'rule' they were forced to follow in Playboy Mansion
  • Hugh Hefner's ex Holly Madison reveals truth about ‘tunnels under the Playboy Mansion that led to Diddy's house'
  • Bizarre food rules the Playboy Mansion had as Hugh Hefner’s personalized 31-item menu is revealed
  • Kendra Wilkinson explains why she 'never bonded' with Holly Madison while in 'throuple' Hugh Hefner relationship

Choose your content:

6 mins ago
an hour ago
3 hours ago
4 hours ago
  • YouTube/CBS Mornings
    6 mins ago

    Lizzo reveals strict social media rules she follows to avoid 'toxic' culture

    The 'Good as Hell' singer has spoken on how she views social media these days

    Celebrity
  • Michael Tran / AFP) (Photo by MICHAEL TRAN/AFP via Getty Images
    an hour ago

    Billie Eilish's ex Jesse Rutherford has awkward response after accidentally favoriting video of her

    Billie Eilish and Jesse Rutherford dated for around a year after first being linked together in 2022

    Celebrity
  • (Photo by Michael Buckner/Variety via Getty Images)
    3 hours ago

    James Franco makes appearance at Cannes Film Festival after being 'cast out' of Hollywood

    The star was all smiles as he posed alongside his long-term girlfriend

    Celebrity
  • (Photo by John Nacion/WireImage)
    4 hours ago

    Emilia Clarke's aneurism 'shame' saw her fear for her Game of Thrones future

    “I was so ashamed that...the people who employed me might see me as weak, or see me as something that could be broken."

    Celebrity