Former Playboy Bunny Holly Madison reveals ‘disgusting’ sex act with Hugh Hefner she 'hated'
An ex-Playboy Bunny and girlfriend of Hugh Hefner has opened up about one thing that she 'made it very known' she 'hated'.
Holly Madison dated Hefner between 2001 and 2008, becoming his 'number one' girlfriend and moving into the infamous Playboy Mansion.
The now-46-year-old has previously opened up about her frustration with people commenting on their 53-year age gap.
“There was a time when I couldn't post anything [on social media] without some dumba** in the comments [being] like, 'Oh, old balls',” she told the In Your Dreams podcast.
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“Maybe some people's balls do get old and nasty, but I've never seen such a thing.”
But there was one part of her relationship with Hefner that Madison admitted she 'hated'.
This was group sex with Hefner and his other girlfriends.
“If it was just me and him, it was a lot more normal than you would think,” 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.”
And this was not the only issue in the relationship either, with another being that Madison claimed that she 'didn’t actually know him that well'.
“I thought I was connecting with [Hefner],” she told the New York Post. “When really I was just somebody who had trouble connecting with people my whole life.
“And I’d met somebody who was like a master manipulator.”
Hefner passed away in 2017 at the age of 91, and after his death several women came forward with claims of abuse.
Following his death, Playboy published an open letter in which the company appeared to distance itself from Hefner.
It read: “Today’s Playboy is not Hugh Hefner’s Playboy. Today, our organization is run by a workforce that is more than 80 percent female, and together we are building upon the aspects of our legacy that have made a positive impact, including serving as a platform for free expression and a convener of safe conversations on sex, inclusion and freedom.
“We will continue to confront any parts of our legacy that do not reflect our values today, and to build upon the progress we have made as we evolve as a company so we can drive positive change for you and our communities.”
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, 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.
'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: News, US News, Celebrity, Hugh Hefner, Sex and Relationships
Kit Roberts