Former Playboy model shares disturbing rule Hugh Hefner made them follow in mansion
Holly Madison has shared some more secrets about what went down behind closed doors at the Playboy mansion.
The former girlfriend of the late magazine magnate Hugh Hefner explained that living at the notorious property in Los Angeles wasn't half as glamorous as it may have appeared.
Although a lot of people imagine that it was a lavish 24-hour party pad where scantily-clad bunnies ran amok, Madison has revealed it was a lot stricter than that, as there was actually a ton of rules to abide by.
The 46-year-old TV star, actress and model has revealed that she spent the majority of the first 12-months in the mansion simply 'trying to not get in trouble' as she adjusted to living under Hefner's roof.
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Madison moved into the mansion in 2001 after striking up a relationship with the Playboy publisher at a tricky time in her life, as she was both homeless and being buried under credit card debt.
But she got quite the rude awakening when she took up residence at Hefner's home, as she had no idea the women who lived there had to follow certain rules.
Speaking on the Baby, This Is Keke Palmer podcast last year, Madison said: "I moved in, and then I realised, 'I don't know what the schedule of this place is'.
"Like, I knew they had a curfew...They had to be in at nine o'clock. I know people think that's weird, and I always get the weirdest looks when I tell people that.
"When I moved in, I was like, 'Well, I'm not going to be here very long'. The girls never last very long here, and, you know, I'm just going to enjoy this for what it is."
She then opened up to podcast host and actress Keke Palmer about what the 'weirdest' element of living at the Playboy mansion was.
Madison continued: "You get into little things like, 'This is the schedule', and 'This is how you're supposed to act, or he'll freak out'.
"I thought it would be fine for me to have a day job during the day - I found out that wasn't the case. There was a lot of stumbling around my first six months to a year, just trying to not get in trouble."
She claimed that Hefner is the one who informed her that seeking employment elsewhere was not permitted.
The mother-of-two, who eventually left the mansion in 2008, has previously opened up about what fulfilling Hefner's sexual needs was like.
While appearing on the In Your Dreams podcast a few years back, she explained that intercourse with her much older boyfriend was 'a lot more normal than you would think'.
However, there was one thing that Madison 'hated' - which is when Hefner wanted an audience to watch them roll around in the sheets.
Recalling what their sex life was like, she said: "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."
Hefner passed away in September 2017 at the age of 91 and is buried in the Westwood Village Memorial Park Cemetery beside Marilyn Monroe.
What else have Playboy Bunnies said about sex with Hugh Hefner?
Hefner was married three times and had several girlfriends, with three of those, Kendra Wilkinson, Holly Madison and Bridget Marquardt, all rising to fame with their reality TV show, Girls Next Door.
A number of former Playboy Bunnies have opened up about intimacy with the late businessman.
'Contaminated' music
In her 2024 biography, titled Only Say Good Things: Surviving Playboy and Finding Myself, Hefner’s third and final wife, Crystal, described sex with him alone as being 'blue little pill nights' due to the medication he needed to get jiggy between the sheets.
She also claimed that she'd played the same Madonna track every time so that 'no other music [would] be contaminated by this place' for her.
'Odd and robotic'
Elsewhere in the book, Crystal called their sex life 'odd and robotic', as she penned: “This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time.
"Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas. The dimming of the lights. The music. The porn. Passing the pot. And then the sex.”
She described the experience as if Hefner 'was just going through the motions of something that had once been fun and sexy’.
Crystal added: “Or maybe it was never fun and sexy.”
'Black book'
While speaking on her and Madison’s Girls Next Level podcast, Marquardt claimed Hefner had a journal, which detailed who had been having sex with him and when.
“The black book kept track of a few different things,” she explained. “It kept track of when somebody collected their allowance. He would mark it off so you couldn’t ask for it twice. It also kept track of who slept with him and when.”
'Almost comical'
Madison also published a book on her time in the Playboy Mansion, called Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
Recalling how she was told to put on pajamas when she was first asked to live in Hefner's estate, she wrote: “When I think about it now, it’s almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner’s bedroom with his harem of blond bombshells. The answer? Not a whole lot.”
She added: “My turn was over just as quickly as it had started.”
'Nobody knew the hell'
Another of Hefner's girlfriends, Sondra Theodore - who dated the magazine publisher for five years between 1976 and 1981, opened up about their time together during an appearance on A&E's Secrets of Playboy.
“He scared me a lot at the end because you couldn't satisfy him — he had to have more and more and more,” Theodore recalled.
“I might as well have been a vibrator, I might as well have been a sex toy — because that's what it was. And nobody knew the hell I was in.”
Like having 'sex with your grandpa'
Twins Karina and Karissa Shannon also spoke about how their 19th birthday was ruined after they were invited to Hefner's bedroom.
While being interviewed for the A&E docuseries, Karissa claimed that they were both offered a pill that made them 'the most inebriated we've ever been', before having sex with the then 86-year-old.
“We had never done a threesome together before, we would never want to,” Karina said.
Meanwhile, Karissa added: “And that was our 19th birthday. You're never going to forget that. He didn't even finish. Just imagine this, just his old hand kind of shakes [as he's] touching your boob.
“It's like you're having sex with your grandpa. And he laid there, looking up, and he was like, 'My babies, my babies. You love me.'”
Karissa continued: “We ran down the hall to the spare bedroom we were staying in. We hit the shower, steaming hot. Our skin was red from just trying to, like, sterilize.”
Topics: Playboy, Hugh Hefner, Celebrity, US News
Olivia Burke