Numerous former Playboy bunnies have opened up about their experiences of life at the Playboy Mansions - including their most intimate moments with founder Hugh Hefner.
Eight years ago, in 2017, the Chicago-born magazine publisher passed away at the age of 91, and since then, more and more of his former girlfriends have spoken out about living in the Playboy Mansion - his Los Angeles estate that he purchased back in 1971.
Hefner was married three times and had numerous girlfriends, with three of those, Kendra Wilkinson, Holly Madison and Bridget Marquardt, all shooting to fame with their reality TV show, Girls Next Door.
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As well as a 2022 documentary, Secrets of Playboy, other girlfriends have given their insight into their lives as one of Hefner's girlfriends.
'Contaminated' music
Upon his death, his third and final wife Crystal Hefner, is believed to have inherited $7 million in cash as well as a $5 million home in Hollywood.
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After marrying an 86-year-old Hefner at the age of 26 herself in 2012, Crystal stayed with him until the end.
In her biography she released last year, titled Only Say Good Things: Surviving Playboy and Finding Myself, Crystal described sex with him alone as being 'blue little pill nights' due to the medication he needed to perform in the sheets.
She also shared that she'd played the same Madonna song each time so that 'no other music [would] be contaminated by this place' for her.
'Odd and robotic'
In the book, she also described their sex life as 'odd and robotic', as she wrote: "This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time.
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"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. Or maybe it was never fun and sexy'.
'Disgusting' sex act and 'normal' manhood
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Speaking on the In Your Dreams Podcast with Owen Thiele, Holly Madison explained what it was like having sex Hefner along with his other girlfriends at the time, compared to when they were alone together, which she described as 'a lot more normal' than what was expected.
Madison explained: “Well, 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. If it was just me and him, it was a lot more normal than you would think.”
She added: “I think everybody has this real horror story of how gross an old man's body must be. I feel like there was a time when I couldn't post anything without some dumb*** in the comments like, 'Oh, old balls', or something like that and look, maybe some people's balls do get old and nasty, but I've never seen such a thing.”
'How embarrassing'
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While speaking on her own podcast Girls Next Level with her co-host Marquardt, Madison described how Hefner acted during the orgies she was involved in.
"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." she said.
"Especially as we got later down the road when there would be, like, a lot of conflict with the other girls.
"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."
Having to be 'intoxicated' to get through it
Kendra Wilkinson, who starred alongside Madison and Marquardt as one of Hefner's three girlfriends that featured on The Girls Next Door, also released a memoir about her time in the Playboy Mansion.
The book, titled Sliding into Home, was released back in 2011 and it detailed how Wilkinson 'survived' the orgies she was involved in.
"I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it," she wrote.
'Two giant TV screens' in bedroom 'playing porn'
Speaking on their podcast, Madison and Marquardt even painted the picture of what his bedroom looked like.
"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," Marquardt shared.
Madison added: "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.”
'Black book'
While Marquardt touched on the fact that 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."
While both Madison and Marquardt also spoke of how they heard tales from other 'bunnies' that he'd called them out if they refused sex with him on personal grounds.
They shared: "He’d be like, ‘Oh, you’ve been on your period for three weeks.' "
'Almost comical'
Like Crystal, Madison also published a book on her time in the Playboy Mansion, titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
Reflecting on how she was ordered 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 then socialite for five years between 1976 and 1981, reflected on their time together while being interviewed for A&E's Secret's 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'
Meanwhile, twins Karina and Karissa Shannon also spoke about how their 19th birthday was ruined after they were invited to Hefner's bedroom.
Speaking on the A&E docuseries, Karissa claimed that they were both offered a pill that made them 'the most inebriated we've ever been', before engaging in sex with the then 86-year-old.
"We had never done a threesome together before, we would never want to," Karina said, to which 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."
Hefner wouldn't use 'protection'
Karissa also claimed how there was a time when a number of Hefner's girlfriends caught chlamydia at the same time due to the millionaire being unwilling to put a condom on.
"The problem is Hef doesn't like to use protection. 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," she 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."
Cleaning 'dildos' from the floor
In the same docuseries, Hefner's former valet, Stefan Tetenbaum, explained how he used to have to collect dildos from his bedroom floor after his sex sessions before readying the room for another round.
"I had to put on rubber gloves and pick up the dildos from the floor and put them in a special bucket," he explained.
"The maids would take them downstairs, spray them with a steam cleaner to sterilize them and then put them in plastic bags. I would carry them back upstairs and put them back in the headboard."
'Hefner taped everything in his bedroom'
Tetenbaum went on to explain how his former boss captured surveillance footage of everything that went on in his bedroom - even when he invited guests to 'use' the room.
"Hefner taped everything in his bedroom and many men and stars and athletes came into the bedroom and had sex with these girls. Most of the time Hefner never participated. He just watched, he was a voyeur," Tetenbaum said.
Madison also claimed in the documentary that he kept videos and photos of women to blackmail them. In 2022, Crystal took to Twitter to share that she had discovered 'thousands' of prints from disposable cameras.
"I found thousands of those disposable camera photos you are talking about @hollymadison," she typed.
"I immediately ripped them up and destroyed every single one of them for you and the countless other women in them. They're gone."
Topics: Hugh Hefner, US News, Sex and Relationships
Joe Yates