Former Playmates have spilled their Hugh Hefner horror stories, including chlamydia outbreaks, “disgusting” group sex and having to endure his mould-addled, “hoarder-style” home
“I was imprisoned,” said Hugh Hefner’s ex-wife Crystal after the Playboy mogul’s death.
The two had met when Crystal was 21 and ‘Hef’ was 60. On New Year’s Eve 2012, the pair married and remained together until a sepsis-induced heart attack caused the multi-millionaire’s death at the age of 91 in 2017.
Writing in her memoirs published after her husband’s death, she painted a disturbing picture of life in his libertine Playboy Mansion, an image since corroborated by countless other ex-Playmates.
Many more Bunnies have described living with Hefner as “hell”, lifting the lid on uncomfortable group sex, secret sex tapes used for blackmail and demeaning chores in his “hoarder” home.
Here’s everything Playmates have said about life and sex with Hef.
“Everything was mouldy”
In her book, Crystal called Hefner “less sex-savvy than some of the teenage boys I’d been with years ago” and said sex with him was “odd and robotic”. When the time for intimacy came, she claimed she would put on the same Madonna song so that “no other music [would] be contaminated” for her.
But bad sex was far from the worst part of life as one of Hefner’s Playmates. Despite the glitzy facade, Crystal claimed the Playboy Mansion was a dump, saying: “Everything was mouldy and dusty and it was just hoarder central in the mansion.”
On the podcast Girls Next Door , co-hosted by Holly Madison, a former girlfriend of Hefner’s, and Bridget Marquardt, another former Playmate, the two described Hefner’s bedroom as a “disaster”. Bridget said: “The lights were out, but there were two giant TV screens in there that were playing porn.”
Holly added: “It was just hoarder-style… It’s like the weird eccentric millionaire version of the guy with the mattress on the floor and a Pulp Fiction poster.”
Dirty ‘toys’ and Hef’s “black book”
In the docuseries, Secrets of a Playboy, former Playboy valet Stefon Tetelbaum expands on just how disgusting the mansion was. She said: “I had to put on rubber gloves and pick up the dildos from the floor and put them in a special bucket.
“The maids would take them downstairs, spray them with a steam cleaner to sterilise them and then put them in plastic bags. I would carry them back upstairs and put them back in the headboard.”
Despite the mess, Hef kept close control over everything that happened in the mansion. Bridget claims that he kept a “black book” to keep track of how much each Playmate had been paid, who had slept with him and when it had happened.
If girls hadn’t had enough sex with them, he would use the black book to call them out. Holly recalled: “He’d be like, ‘Oh, you’ve been on your period for three weeks.’”
Blackmail and Big Brother
Hef also apparently kept constant surveillance in the house, with cameras recording in every room – even after Playmates asked for them to be switched off. “He was a voyeur,” said Stefon. “Hefner taped everything in his bedroom and many men and star athletes came into the bedroom and had sex with these girls.”
Hef would then keep these tapes, featuring hundreds of girls, and use them for blackmail. In 2022, Crystal tweeted: “I found thousands of those disposable camera photos you are talking about… I immediately ripped up and destroyed every single one of them.”
Another favourite activity of Hef’s was group sex, which Holly called “disgusting”. She continued: “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… You’re literally sitting there naked having sex in front of a group of people who hate you and talk sh*t about you while you’re having sex. It was like hell.”
“Like having sex with your grandpa”
Twin sisters Kristina and Karissa Shannon, who were invited to Hefner’s bedroom on their 19th birthday, said they were pressured to have a threesome with the then 82-year-old. They said he gave them a pill that made them feel “the most inebriated we’ve ever been” before being solicited for the threesome, which “we would never want to do”.
“It’s like having sex with your grandpa,” Karissa reported, adding that afterwards they “ran down the hall… We hit the shower, steaming hot. Our skin was red from just trying to sterilise.”
The twins also complained of multiple chlamydia outbreaks in the mansion since 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.”
Kendra Wilkinson, another former girlfriend, remembered: “I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it.”
