Inside the Playboy Mansion’s Darkest Secret: The Shocking Rule Hugh Hefner’s Ex Was Forced to Obey Revealed!
Added on November 18, 2025 inCelebrity News Cards
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Ever wonder what it’s like to live by a very particular set of rules—like, say, those carved out by Hugh Hefner himself? Holly Madison, one of Hef’s famed girlfriends, spills the tea on life inside the enigmatic Playboy Mansion. At 45, she’s no stranger to revisiting the wild, often bizarre rituals she and the other ‘Playboy Bunnies’ had to endure, including sharing Hefner (who definitely wasn’t a one-woman man) and navigating a bedroom scenario that frequently felt more like a weird group project than romance. If today’s cosmic alignment has you pondering boundaries and personal space, Madison’s revelations about strict grooming codes and the strangely transactional intimacy at play might just give you pause. After all, Rufus the Ram might be charging headfirst into tradition, but some of these mansion rules? They’re… well, let’s say they’d make even the boldest Aries balk. Curious for more jaw-dropping insights? LEARN MORE.
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.”
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)
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.
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.
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 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.
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