Ex-Playboy Bunny girlfriends of Hugh Hefner have opened up about getting intimate with the magazine publisher after Holly Madison revealed all about her experience.
Holly Madison is probably one of the most known ex’s of Hefner, and dated him between 2001 and 2008.
As his 'number one' girlfriend, Madison moved into the Playboy Mansion, where she had to share her boyfriend with other women, and many of them have negative feelings about what went on in the mansion.
The now-46-year-old has been open about the 53-year age gap, revealing that people took to social media for the longest time, mocking her over Hefner’s alleged ‘old balls’.
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She said on the In Your Dreams podcast, that she had ‘never seen such a thing’, and that they typically had sex in the dark.
‘That was disgusting’
However, she did mention that she ‘hated’ group sex with him and the other bunnies, and the feeling was mutual.
“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.”
Since Hefner's death in 2017 at age 91, many of his former girlfriends have voiced their disgust for some of the behaviors in the home, with some more serious things that were later revealed in the A&E docuseries Secrets of Playboy.
‘Less sex-savvy than teenage boys’
Hefner’s last wife before his death, Crystal Hefner revealed in her memoir, Only Say Good Things: Surviving Playboy and Finding Myself, Hefner was 'less sex-savvy than some of the teenage boys I’d been with years ago’.
'It was hell'
Madison and her Girls Next Door costar Bridget Marquardt also co-host the podcast, Girls Next Level, and in some of the episodes, Madison revealed Hefner was like a ‘log’ in the bedroom, explaining: “He wouldn’t move. He would be like a bump on the log in the middle of the bed. I can’t explain to you guys how embarrassing that whole routine was. Especially as we got later down the road when there would be, like, a lot of conflict with the other girls.”
She said, per the New York Post: "You’re literally sitting there naked having sex in front of a group of people who hate you and talk s*** about you while you’re having sex, and you can hear it. It was just, like, hell.”
'Hoarder bedroom’
On the same podcast, ex-girlfriend Marquardt claimed Hefner’s room was a nightmare, and covered in ‘junk’.
"We walked in and it was just a disaster in there. The lights were out, but there were two giant TV screens in there that were playing porn … There’s just so much junk," she said.
Madison also shared: "It was just hoarder-style. Imagine thinking you’re this big player and you’re bringing all these girls home, and your room looks like s***. It’s like the weird eccentric millionaire version of the guy with the mattress on the floor and a Pulp Fiction poster.”
'Doesn't like to use protection'
In the docuseries, Karissa and Kristina Shannon claimed girls would catch chlamydia because the Playboy boss didn’t like to use condoms.
"From the butlers, we'd just order a big bowl and we'd put hot water in it, then we'd put rags in it," Karissa said. "So whoever was having intercourse with him, when they were finished, they can wipe him off. And then the other girl could do it."
‘There was no way around it’
Kendra Wilkinson, who was in a quad relationship with Hef, Madison, and Marquardt, revealed in her book, Sliding into Home, that she had to take substances to get through the group sex sessions, writing: “I had to be very drunk or smoke lots of weed to survive those nights – there was no way around 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 Kristina 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,” Kristina 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: Sex and Relationships, Hugh Hefner, US News
Britt Jones