ladbible homepage
ladbible homepage
  • Home
  • News
    • UK
    • US
    • World
    • Ireland
    • Australia
    • Science
    • Crime
    • Weather
  • Entertainment
    • Celebrity
    • TV
    • Film
    • Music
    • Gaming
    • Netflix
    • Disney
  • Sport
  • Technology
  • Travel
  • Lifestyle
  • Money
  • Originals
    • FFS PRODUCTIONS
    • Say Maaate to a Mate
    • Daily Ladness
    • UOKM8?
    • FreeToBe
    • Citizen Reef
  • Advertise
  • Terms
  • Privacy & Cookies
  • License Our Content
  • About Us & Contact
  • Jobs
  • Latest
  • Archive
  • Topics A-Z
  • Authors
Facebook
Instagram
X
Threads
Snapchat
TikTok
YouTube
Submit Your Content Here
  • SPORTbible
  • Tyla
  • GAMINGbible
  • LADbible Group
  • UNILAD
  • FOODbible
  • UNILAD Tech
Former girlfriend of Hugh Hefner revealed disturbing rule they were forced to follow in Playboy mansion
Home>Entertainment>Celebrity
Published 19:01 18 Nov 2025 GMT

Former girlfriend of Hugh Hefner revealed disturbing rule they were forced to follow in Playboy mansion

Holly Madison revealed one of Hefner's more unsettling rules for the Playboy Mansion

Joshua Nair

Joshua Nair

google discoverFollow us on Google Discover

Hugh Hefner's ex-girlfriend, Holly Madison, opened up on some of the rules she had to follow while living in the Playboy Mansion.

Now 45, Madison has previously opened up on her experience as one of Hef's many girlfriends, speaking about some of the things the famous 'Playboy Bunnies' would have to do for the famous publisher.

The American TV personality revealed that they would often have to share Hefner between themselves, as he would have several other girlfriends at the same time.

In the bedroom, she revealed that she 'hated' it when 'everybody else' was in the room during sexual acts, explaining: "If it was just me and him, it was a lot more normal than you would think."

Advert

She even admitted in her 2015 book Down the Rabbit Hole that there were 'rituals' for the girlfriends, which included sleeping with Hefner before bed every night.

Holly Madison started dating Hugh Hefner at the age of just 22, while he was 75 (Lawrence Lucier/FilmMagic)
Holly Madison started dating Hugh Hefner at the age of just 22, while he was 75 (Lawrence Lucier/FilmMagic)

Now, the former Playboy Bunny, who was one of the few girlfriends who held a permanent residence at the Playboy Mansion, spoke about some of the disturbing rules they would have to follow.

Strict rules on shaving

Speaking on the Call Her Daddy podcast back in 2021, the reality star explained: "He (Hefner) would get mad if somebody wasn’t shaved," adding that he 'liked vaginas to look a certain way', with 'nothing sticking out'.

Madison confirmed that he preferred 'inies not outies', after host Alex Cooper asked, even revealing that a girl who had an 'outie' was not invited back.

She added of the late businessman, who died aged 91 in September 2017, that he always had to take Viagra before any bedroom sessions.

Sex positions and intimacy issues

Madison, who started dating Hefner in 2001 at the age of 22, even revealed his favourite sex position, explaining: "He was on top the first time, but he was always lying down every other time that I remember."

That wasn't all, though, as the mum-of-two said that she never orgasmed while being intimate with the former Playboy CEO, pointing out that it 'was too messed up', as Cooper said it seemed 'fully transactional'.

Madison said she didn't enjoy most of her sexual encounters with Hefner (Denise Truscello/Getty Images for BOA Steakhouse Las Vegas)
Madison said she didn't enjoy most of her sexual encounters with Hefner (Denise Truscello/Getty Images for BOA Steakhouse Las Vegas)

Madison said it felt like being with him wasn't the best feeling, adding: “In the moment, you’re like, this is, it’s almost like your job. And just messed up like drunk and high.”

She even addressed criticism from others claiming she knew what she was getting into before moving into the mansion, as Madison claimed she 'absolutely did not'.

"I thought I kind of had a hazy idea of what living at the mansion would be before I moved in, but nobody breaks it down for you," the former model began.

"I think people imagine it being like 50 Shades of Grey, where the woman is sat down in a conference room and given this long contract, and you’re told exactly what’s going to happen, and what do you consent to, and what do you not."

Apparently, the other girls wouldn't tell her what was coming either, sadly admitting: “Nobody really wants to help anybody out – everybody wants a centerfold,” concluding that they all wanted more money.

Featured Image Credit: Robert Mora/Getty Images

Topics: Hugh Hefner, Celebrity, Playboy, Sex and Relationships, Podcast

Joshua Nair
Joshua Nair

Joshua Nair is a journalist at LADbible. Born in Malaysia and raised in Dubai, he has always been interested in writing about a range of subjects, from sports to trending pop culture news. After graduating from Oxford Brookes University with a BA in Media, Journalism and Publishing, he got a job freelance writing for SPORTbible while working in marketing before landing a full-time role at LADbible. Unfortunately, he's unhealthily obsessed with Manchester United, which takes its toll on his mental and physical health. Daily.

X

@joshnair10

Recommended reads

Why Dana White announced Conor McGregor's comeback fight during Francis Ngannou Netflix walkoutChris Unger/Zuffa LLC via Getty ImagesGTA 6 pre-order chaos begins after third delay ruled outRockstarMan arrested at Venezuela Fury's wedding held on suspicion of 'licensing offence'TikTok/parisvenezeulaEuphoria creator called out for 'insane' scene in 'diabolical' new episodeHBO

Advert

  • Former Playboy model shares disturbing rule Hugh Hefner made them follow in mansion
  • Margot Robbie turned down Hugh Hefner offer to appear in Playboy
  • Playboy Bunny shares strict rules they had to follow living in the mansion
  • Hugh Hefner's former partner shares strict rules Playboy founder had for his girlfriends

Choose your content:

an hour ago
2 hours ago
  • Rockstar
    an hour ago

    GTA 6 pre-order chaos begins after third delay ruled out

    Best Buy may have got it wrong, according to the latest on GTA 6 pre-orders

    Entertainment
  • HBO
    2 hours ago

    Euphoria creator called out for 'insane' scene in 'diabolical' new episode

    It's the second time the symbol has been shown in Euphoria season three

    Entertainment
  • Mireya Acierto/Getty Images
    2 hours ago

    Shakira has €55m returned in new case after previously avoiding threat of eight-year jail sentence

    It's been affecting her greatly for nearly a decade

    Entertainment
  • BBC
    2 hours ago

    BBC Panorama to address MAFS sexual misconduct allegations in last-minute schedule change

    The documentary sees three women make allegations of sexual misconduct of their on screen former husbands

    Entertainment