Everything Playboy Bunnies Have Said About Having Bad Sex with Hugh Hefner: ‘It Was Hell’
As the founder of Playboy, Hugh Hefner cultivated a larger-than-life image of endless women, extravagant parties, and unrestrained sexuality. He reinforced this impression for decades at the Playboy Mansion, where numerous women would be invited to his bedroom or the infamous grotto. The fascination with his lifestyle surged again in 2005 with a reality show following his girlfriends.
Since Hefner’s passing in 2017 at the age of 91, many of his former partners have come forward, revealing that his sexual prowess was greatly exaggerated. This, alongside more serious allegations, is addressed in the documentary series. From his last wife, Crystal Hefner, stating in her memoir that Hef seemed “less sex-savvy than some of the teenage boys I’d been with years ago,” to former playmates describing the perfunctory “chore” of intimacy with him, here’s what ex-Playboy bunnies and employees have said about the reality.
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**’Odd and Robotic’**
Crystal Hefner, who met Hugh Hefner when she was 21 (60 years his junior), and married him five years later, described her experiences in the Playboy Mansion in her book, detailing the “odd and robotic” sexual encounters Hefner expected from her and the other women.
“This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time,” Crystal wrote. “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 added, it was “like Hef was just going through the motions of something that had once been fun and sexy. Or maybe it was never fun and sexy.”
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**’All Cats Are Gray in the Dark’**
Holly Madison clarified that while she “hated” the “disgusting” group encounters, the one-on-one intimacy was “more normal than you’d think.”
When someone expressed disbelief, Madison responded, “Nobody does… There was a time when I couldn’t post anything [on social media] without some dumba– in the comments like, ‘Oh, old balls’… Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
She did clarify, though, that the lights were out, so she couldn’t speak with total authority on the subject. “I mean, there’s a saying: ‘All cats are grey in the dark.'”
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**’Little Blue Pill Nights’**
Group intimacy was commonplace for Hef, and Crystal wrote that she preferred it to being alone with him, which she referred to as their “little blue pill nights.” Because he required medication and music, Crystal played the same Madonna song each time, ensuring “no other music [would] be contaminated by this place.”
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**’It Was Hell’**
Holly Madison and her Girls Next Door co-star Bridget Marquardt reflected on their intimate moments with Hefner on their podcast.
Madison reiterated the common sentiment that the girls viewed it as a chore they wanted to finish quickly. She added that the voyeuristic aspect of having other “girlfriends” watching made it particularly unpleasant.
“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. “You’re literally sitting there naked having intimacy in front of a group of people who hate you and talk s— about you while you’re having intimacy, and you can hear it. It was just, like, hell.”
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**Tracking Their Movements**
On the same podcast, Marquardt revealed that Hefner kept a diary to monitor the girls.
“The black book kept track of a few different things,” Marquardt 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.”
She and Madison heard of other girls being reprimanded for lack of participation: “He’d be like, ‘Oh, you’ve been on your period for three weeks.'”
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**’You Couldn’t Satisfy Him’**
Sondra Theodore, Hefner’s girlfriend from 1976 to 1981, recalled that his growing fame led to escalating demands, eventually “breaking [her] like you would break a horse.”
“He scared me a lot at the end because you couldn’t satisfy him — he had to have more and more and more,” she 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.”
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**’Get It Over with as Quickly as Possible’**
Upon being recruited, Holly Madison was surprised to learn that she and other girls would be chosen to wear matching pajamas and take turns with Hefner. They all “tried to get it over with as quickly as possible,” she wrote in her memoir.
“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,” Madison wrote, noting she was encouraged to “fake” it to speed things up: “My turn was over just as quickly as it had started.”
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**’Hoarder-Style’ Bedroom**
Many “girlfriends” have commented on the untidiness of Hef’s bedroom, including Madison and Marquardt, who discussed the ‘disaster’ on their podcast.
“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 adult films… There’s just so much junk,” said Marquardt.
Madison agreed: “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 movie poster.”
Crystal shared similar thoughts in her memoir: “Everything was moldy and dusty and it was just hoarder central in the mansion.”
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**’I Had to Pick Up the Dildos from the Floor’**
Hefner’s former valet recounted the process of retrieving used adult toys after bedroom sessions and preparing them for the next one.
“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.”
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**’He Had Tapes on Everyone’**
Theodore stated that Hefner had cameras in his bedroom and, even if a girl objected and he pretended to turn them off, the tapes would surface later.
According to the valet, “Hefner taped everything in his bedroom and many men and stars and athletes came into the bedroom and had intimacy with these girls. Most of the time Hefner never participated. He just watched, he was a voyeur.”
The use of videos and photos as leverage continued for decades; Madison said she knew he kept photos of hundreds of girls for that purpose.
In 2022, Crystal shared that she’d discovered and destroyed those pictures: “I found thousands of those disposable camera photos you are talking about… I immediately ripped them up and destroyed every single one of them for [Madison] and the countless other women in them. They’re gone.”
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**’Like Having Intimacy with Your Grandpa’**
Twins Karina and Karissa Shannon were invited to Hefner’s bedroom on their 19th birthday, feeling obligated due to the promise of a magazine centerfold. Karissa recalled him offering a pill that made them feel “the most inebriated we’ve ever been,” then engaging them in sexual activity.
According to Karina, “We had never done a threesome together before, we would never want to.”
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 intimacy with your grandpa. And he laid there, looking up, and he was like, ‘My babies, my babies. You love me.'”
When Hefner finished, Karissa said, “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.”
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**’Hef Doesn’t Like to Use Protection’**
The Shannon twins recalled a time when multiple girls contracted an infection and were told it was a natural consequence of being sexually active, as Hef wasn’t willing 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,” 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.”
Marquardt spoke similarly about the lack of protection, saying she’d usually try to go first during group intimacy since that seemed “cleanest.”
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**’I Had to Be Very Drunk to Survive Those Nights’**
Kendra Wilkinson echoed what many others had said about how unpleasant the nights of group intimacy were: “I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it.”
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