Former Playboy Bunny Holly Madison reveals ‘disgusting’ sex act with Hugh Hefner she ‘hated’ doing
Holly Madison once opened up about the ‘disgusting’ thing she ‘hated’ doing with Hugh Hefner during the years she was living at his Californian mansion.
45-year-old Madison was just 22 when she struck up a relationship with Hefner, the Playboy founder who died in 2017.
The pair, who shared a 53-year age gap, were together from 2001 until 2008, though the father-of-four simultaneously favoured other women like Bridget Marquardt and Kendra Wilkinson during this time.
Madison, a former Playboy model and reality TV star, has revealed a slew of details about life in the mansion over the years. These include extreme 'rules' that residents had to abide by, such as not wearing lipstick.
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Another legislation Hefner’s girlfriends reportedly had to abide by was group sex parties—an activity Madison has previously discussed on Owen Thiele’s In Your Dreams podcast.
The mother-of-two claimed that while sex was a ‘very different story’ when she and Hefner were alone, it was really ‘disgusting’ when everyone else was in the room.
"I hated it. I made it very known I hated it," she explained.
Madison noted that her one-on-one time with Hefner was far more 'normal', continuing: "If it was just me and him, it was a lot more normal than you would think."
The Girls Next Door icon continued, claiming her age gap relationship never bothered her, but that she would receive criticism from others.
"I feel like there was a time when I couldn’t post anything without some dumbass in the comments like, 'Oh, old balls,' or something like that," she told Thiele.
"Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing."
Madison also used the podcast to clarify how she and Hefner would keep the lights off while having sex, adding: "I mean, there's a saying: 'All cats are grey in the dark.'"
According to the former model, the prolific sex parties always took place on the same two days of the week.
"It was always Wednesdays and Fridays after the club. It was always exactly the same because that's just how he likes to live his life," she told Buzzfeed in 2015
According to Madison, all of Hugh's girlfriends were required to take part as she explained: "They knew it was kind of a quote-unquote requirement for living there, and expected.
"And it had kind of a chore vibe, I felt."
In 2022, Madison claimed her ex-boyfriend was also extremely controlling about the way she looked.
Appearing on A&E’s Secrets of Playboy, she explained: "I got to a point not too far into my time there… where I kind of broke under that pressure and being made to feel like I needed to look exactly like everybody else.
"My hair was really long naturally, and I was just like, 'I’m gonna go chop my hair off so I can at least look a little different'."
Madison said cutting off her hair allegedly made Hefner ‘flip out’, cruelly telling her the haircut made her ‘look old, hard and cheap’.
She said: "I remember there were times probably within the first couple years I lived there when I felt like I was just in this cycle of gross things and I didn’t know what to do."
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.
'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.”
Several Playboy Bunnies have spoken out about their experience with the late magazine publisher (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 pyjamas 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 fantasised 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: Celebrity, Entertainment, Hugh Hefner, Playboy, Podcasts, Sex and Relationships, Reality TV
Ella Scott