She’s not the only former Playboy Bunny to speak out about her time with Hugh Hefner
A former Playboy Bunny and one-time girlfriend of Hugh Hefner has shared details about part of her experience that she described as ‘disgusting’.
Holly Madison was in a relationship with Hefner from 2001 until 2008. During that time, she became his main partner and moved into the well-known Playboy Mansion.
Now aged 46, Madison has spoken in the past about how people often focused on the large age gap between them, which was more than five decades.
“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 said during an appearance on the In Your Dreams podcast.
“Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
Even with that, Madison made it clear that there was one part of the relationship that she could not stand.
Holly Madison opened up about her relationship with Hugh HefnerTaylor Hill/Getty Images
That part involved group situations with Hefner and other girlfriends living in the mansion.
“If it was just me and him, it was a lot more normal than you would think,” she explained.
“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.”
She also shared that this was not the only issue in the relationship. Another problem was that she felt she never truly got to know Hefner, even though she believed at the time that they had some kind of connection.
“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. After his death, several women came forward and shared their own stories, including claims of troubling behavior.
After his passing, Playboy released a public statement that appeared to separate the company from parts of its past.
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.”
The pair dated between 2001 and 2008J. Merritt/FilmMagic
What else have Playboy Bunnies said about sex with Hugh Hefner?
Hefner was married three times and had several long-term partners. Some of them, including Kendra Wilkinson, Holly Madison, and Bridget Marquardt, became widely known through the reality show Girls Next Door.
Over time, a number of former Playboy Bunnies have shared their own experiences about what went on behind the scenes.
Hefner with Kendra Wilkinson, Bridget Marquardt, and Holly Madison in 2004Carlo Allegri/Getty Images
‘Contaminated’ music
In her 2024 memoir, Only Say Good Things: Surviving Playboy and Finding Myself, Hefner’s third wife, Crystal, described private moments with him in a way that suggested a routine pattern.
She referred to those moments as ‘blue little pill nights’, pointing to the medication he relied on.
She also explained that she would play the same Madonna song each time so that ‘no other music [would] be contaminated by this place’, which shows how she tried to separate that experience from the rest of her life.
‘Odd and robotic’
In the same book, Crystal described their experiences as feeling mechanical and repetitive.
She wrote: “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 explained that it felt like Hefner was repeating something that may have once been enjoyable but no longer felt that way.
Crystal added: “Or maybe it was never fun and sexy.”
‘Black book’
Speaking on the Girls Next Level podcast, Bridget Marquardt said Hefner kept detailed notes about his personal life.
“The black book kept track of a few different things,” she said. “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.”
A number of women have opened up about their experience at the Playboy MansionM. Tran/FilmMagic
‘Almost comical’
Madison also wrote about her time in the mansion in her book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
She described what happened when she was first asked to move in, recalling the instructions she was given and how things unfolded.
“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’
Sondra Theodore, who dated Hefner for several years in the late 1970s and early 1980s, also spoke about her experience in the A&E series 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,” she said.
“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 shared their experience, saying their 19th birthday took a turn they did not expect after being invited into Hefner’s room.
During the A&E docuseries, Karissa said they were given something that made them feel extremely intoxicated before anything happened.
“We had never done a threesome together before, we would never want to,” Karina explained.
The twins pictured with Hefner in 2009Michael Bezjian/WireImage
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.'”
She went on to say: “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.”