Former Playboy model Holly Madison breaks down 'compulsive sex nights' with Hugh Hefner
Holly Madison has broken down the 'weird' sex ritual Hugh Hefner expected everyone to do, but 'nobody liked'.
The 46-year-old TV personality, who lived in the infamous Playboy mansion between 2001 and 2008, is no stranger to sharing exactly what went down while she was Hefner's 'Number One Girl' all those years ago.
She's previously detailed the 'disgusting' sex act with Hefner she 'hated' doing, the bizarre sex item he used to keep in his bedroom and the 'gross' reality of her relationship with the publisher, who died aged 91 back in 2017.
But her latest Hefner admission came while speaking on the Let's Be Honest with Kristin Cavallari podcast earlier this week (5 May), where she opened up about the strict schedule she and the other Playmates had to follow when it came to the bedroom and how that dramatically changed once filming began on The Girls Next Door reality TV series.
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"You've openly talked about the group sex that you guys had to have. So explain that whole scene to me," Cavallari said. "So that's all of the girlfriends and Hef?"
"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," Madison explained. "It would be like kind of silhouetted because you'd have like these giant screens of porn going. Oh my God. And it would be just girls like talking sh*t with each other.
"And it was a really weird scene, and nobody liked it. And everybody tried to just get it done as fast as possible."
"How often were you guys required to have sex with him?" Cavallari carried on, to which Madison responded: "Well, in the beginning, we would go out twice a week, and it would always be like after we would go out.
"But after we started filming the show, that just stopped, which was amazing."
The model recalled how she and her housemates would regularly go to nightclubs with Hefner on Wednesdays and Fridays before returning to the infamous mansion.
"We stopped those regular club nights where we're going out every Wednesday and Friday because we were so busy with the show, and he loved the show," she said.
Madison went on to claim that Hefner's refreshed fame, due to the E! series, seemingly lowered his need for 'compulsive sex nights'.
"He was like high off the show," she continued. "It gave him, like, new relevance, like the ego boost, so he didn't really feel the need to like, 'Oh, I have to do these compulsive sex nights to make myself feel wanted and relevant,' I think."
Madison explained that, over time, the dynamic between Hefner and the Playmates inside the mansion 'kind of evolved'.
With that said, however, she did outline that there was never an official conversation about calling it quits when it came to Hefner's sex routine schedule.
"There was no discussion. It just kind of - that's how it evolved," Madison said, adding that she, Bridget Marquardt, and Kendra Wilkinson were all on the 'same page' when it came to stopping the group sex parties.
"I think me, Bridget, and Kendra were so on the same page that we just didn't wanna do that anymore," she recalled.
"Nobody had to say anything. We were just like, 'Okay, we're not going out anymore, so nobody's gonna initiate.'"
What else have Playboy Bunnies said about sex with Hugh Hefner?
Hefner was married three times and had several girlfriends, with three of those, Wilkinson, Madison and 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.
'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.”
A number of women have spoken out about their time in the Playboy Mansion (M. Tran/FilmMagic)
'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, Celebrity, Hugh Hefner, Sex and Relationships
Rhiannon Ingle