Hugh Hefner's ex Holly Madison says Playboy Mansion could be 'a little bit scary'
Holly Madison is looking back on her time at the Playboy Mansion, which she revealed wasn’t as glamorous as you’d expect.
The reality TV star has been active in talking about her life as the former partner of Playboy owner Hugh Hefner.
Madison was his official beau from 2001 to 2008, and at one point, was in a quad-coupling with Hefner, Bridget Marquardt, and Kendra Wilkinson.
Previously, she and Marquardt spoke on their reality show Girls Next Door, claimed Hefner kept a journal, aka the 'black book', which tracked who slept with him and when, and who had collected their weekly allowance.
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There were also odd rules he allegedly gave the women regarding what food they could eat, citing his need for healthy foods, until it came to his love of cakes.
Among the strange life at the mansion, Madison said she sometimes felt that it was ‘scary’, and mostly, that came down to who was in the home.
She told Page Six in an interview published yesterday (June 1), that she first ‘saw it as a safe harbor’ after moving in at the turn of the century.
However, she went on to reveal that it ‘turned out to be so much more complicated than that.’
Madison explained that when she moved in at 21, she noticed ‘a lot of predatory people’ involved in the entertainment industry who were out ‘looking for young women who aren’t that sophisticated.’
While she said she was ‘aware of the dangers out there’ for young women, she had believed Hefner’s mansion ‘would be a safe place to go.’
But she said it became clear just ‘how people can turn on each other so quickly.’
“It was very much an ‘everybody out for themselves’ kind of environment,” she told the outlet.
Recently, she was also heard speaking on the Baby, This is Keke Palmer Podcast, where Madison explained that she didn’t know what she was getting herself into.
"I moved in, and then I realised, 'I don't know what the schedule of this place is'," she said.
"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."
She also revealed that she wasn’t allowed to work, noting: "I thought it would be fine for me to have a day job, 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."
It doesn’t sound as exciting as it was portrayed on TV, does it?
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.
However, a number of former Playboy Bunnies have opened up about intimacy with the late businessman.
'Disgusting' sex act
Madison, who dated Hefner between 2001 and 2008, has been very candid about her sex life with the Playboy founder.
Speaking on the In Your Dreams podcast, she revealed: “If it was just me and him, it was a lot more normal than you would think.
“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.”
'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: Hugh Hefner, Celebrity
Britt Jones