Everything Playboy Bunnies Have Said About Having Bad Sex with Hugh Hefner: 'It Was Hell'

Crystal Hefner, Holly Madison and Bridget Marquardt are among the former Playmates who have spoken out about how much they disliked having sex with 'Playboy' founder Hugh Hefner

As the founder of Playboy, Hugh Hefner had a larger-than-life reputation for having tons of women, wild parties and even wilder sex. In the decades since the magazine was founded, he played up that impression by presiding over the Playboy Mansion, where dozens of scantily clad women would be summoned to his bedroom or to the infamous grotto for X-rated escapades. A resurgence of interest in his over-the-top lifestyle occurred in 2005, when E! camera crews followed girlfriends Holly Madison, Bridget Marquardt and Kendra Wilkinson during their time in the mansion.

Since Hefner's death in 2017 at age 91, however, many of his former girlfriends from the '70s and beyond have gone on the record to say that his prowess in the bedroom was greatly exaggerated (in addition to more serious allegations, addressed in the A&E docuseries Secrets of Playboy). From his last wife Crystal Hefner saying in her memoir that Hef seemed "less sex-savvy than some of the teenage boys I’d been with years ago" to Madison and Marquardt breaking down the perfunctory "chore" of having sex with him, read on for everything the former Playboy bunnies and Hefner's employees have said about how bad it really was.

'Odd and Robotic'

Hugh Hefner's last wife, Crystal, met him when she was 21 and he was 60 years her senior; they wed five years later. In her book Only Say Good Things: Surviving Playboy and Finding Myself, she writes about her time in the Playboy Mansion — including the "odd and robotic" sex Hefner required of her and the other girls around at the time.

"This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time,” Crystal writes. “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 adds 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.”

'Little Blue Pill Nights'

Group sex was the norm for Hef, and Crystal writes that she preferred it to having to have sex with him alone — what she called their "little blue pill nights." Because he required medication and music to perform, Crystal turned on the same Madonna song each time to ensure "no other music [would] be contaminated by this place" for her.

'It Was Hell'

Holly Madison and her Girls Next Door costar Bridget Marquardt co-host a podcast called Girls Next Level, and in a few early episodes, reflected on their time in the bedroom with Hefner.

Reiterating a common theme – that the girls thought of it as a chore and wanted to get through it quickly — Madison added that the voyeuristic aspect of having other "girlfriends" watching made it especially unpleasant for her.

“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, according to 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.”

Tracking Their Movements

On the same podcast, Marquardt said that Hefner kept a diary to keep tabs on 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 said they heard of other girls getting called out for lack of participation: "He’d be like, ‘Oh, you’ve been on your period for three weeks.' "

'You Couldn't Satisfy Him'

Sondra Theodore, who was Hugh Hefner's girlfriend from 1976 to 1981, recounted in A&E's Secrets of Playboy that though their relationship started off straightforwardly enough, Hef's growing fame and reputation as the "Playboy" led his demands to escalate, 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."

'Get It Over with as Quickly as Possible'

When she was first recruited, Holly Madison was surprised to find out that she and a number of girls would be chosen that night to put on matching pajamas and line up for their turn with Hefner. All of them "tried to get it over with as quickly as possible," she writes in her memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.

“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 writes, noting that she was encouraged to "fake" it to move things along: “My turn was over just as quickly as it had started.”

'Hoarder-Style' Bedroom

Many "girlfriends" have commented on the mess in Hef's bedroom, including Madison and Marquardt, who discussed the 'disaster' on their Girls Next Level 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 porn … 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 Pulp Fiction poster.”

In her memoir, Crystal shared similar thoughts: "Everything was moldy and dusty and it was just hoarder central in the mansion."

'I Had to Pick Up the Dildos from the Floor'

In an interview for A&E's Secrets of Playboy, Hefner's former valet Stefon Tetelbaum recounted the process of retrieving the used sex toys after one of the bedroom sessions and getting them ready 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," explained Tetenbaum. "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."

'He Had Tapes on Everyone'

In the A&E docuseries, Theodore said that Hefner had cameras in his bedroom and if a girl objected, would pretend to turn them off — but the tapes would surface days later anyway.

According to Tetenbaum, "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."

The use of videos and photos as blackmail continued for decades; Madison said in the documentary she knew that he kept photos of hundreds of girls for just that purpose.

In 2022, Crystal shared on Twitter 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 you and the countless other women in them. They're gone."

'Like Having Sex with Your Grandpa'

Twins Karina and Karissa Shannon were invited to Hefner's bedroom on their 19th birthday, which they felt obligated to do as a promised magazine centerfold hung in the balance. In the A&E docuseries, Karissa recalls him offering a pill that immediately made them feel "the most inebriated we've ever been," then engaging the two of 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 sex 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."

'Hef Doesn't Like to Use Protection'

In the docuseries, the Shannon twins also recalled the time that multiple girls caught chlamydia, and were told by their "house mom" that it was a natural consequence of being sexually active. After all, 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."

On her Girls Level Up podcast, Marquardt spoke similarly about the lack of protected sex, saying she'd usually try to go first during group sex as that seemed "cleanest."

'I Had to Be Very Drunk to Survive Those Nights'

In her 2011 memoir Sliding into Home, Kendra Wilkinson (who, with Holly Madison and Bridget Marquardt, were the three featured "girlfriends" on the E! show The Girls Next Door), echoed what many others had said about how unpleasant the nights of group sex 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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