Hugh Hefner's ex wife Crystal has opened up about life in the infamous Playboy mansion, admitting there was a 'well oiled' routine the late magazine founder had in place for sex.
Having founded Playboy back in 1953, Hefner captured major media attention after he began sharing insights into his Playboy mansion where he would live with his many girlfriends. He purchased the infamous sprawling California property in 1971 for the price tag of $1.1million.
But following his death aged 91 in 2017, several of his former girlfriends have since spoken out about their experiences living in the mansion - painting a pretty damning picture of a life fuelled by sex, partying, and strict rules.
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One of those is Crystal Hefner, who met the Playboy founder when she was just 21 and he was 60.
In her tell-all book Only Say Good Things: Surviving Playboy and Finding Myself, Crystal gets candid about her most intimate moments with Hefner, following in the footsteps of other women who have spoken out about the bizarre routines and rituals that were part of the daily life of living in the infamous property.
From little black books to chore-like sex and even banning one lipstick shade, here are some of the most shocking claims about Hugh Hefner's sex life and what it was like living under his roof.
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Sex with Hefner was 'odd and robotic'
Having tied the knot five years into their relationship, Crystal was with Hefner right up until his death eight years ago - but when it came to their sex life, she said it was 'odd and robotic' and like a 'well oiled machine'.
In her book, she explained that sex became a 'well-practiced sequence of events' and '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 revealed.
"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."
Solo sex with Hefner was branded 'little blue pill nights'
Crystal also revealed in her book that she much preferred group sex to having to solo it with the Playboy founder in what she described as 'little blue pill nights', in reference to the medication Hefner needed to take to do the deed.
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Apparently, it wasn't just pills he needed either to perform - but music too.
Crystal explained that to avoid other music becoming 'contaminated' from her time in the mansion, she would opt for the same Madonna song every time.
Hefner 'had tapes' of everything in his room for sinister reason
Another of Hefner's girlfriends, Sondra Theodore, claimed he would keep tabs on everything as the camera was rolling in his bedroom when guests came and went.
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"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," Hefner's former butler Stefan Tetenbaum alleged.
Even more sinister are claims that he kept videos and photos of women to blackmail them, with former girlfriend Holly Madison admitting she was aware this was going on at the time.
Shockingly, in 2022, Crystal took to Twitter to share that she had discovered 'thousands' of the photos Madison was speaking about and 'immediately ripped them up'.
"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," she wrote.
Having to be 'drunk' just to 'survive those nights'
In her memoir Sliding into Home, Kendra Wilkinson admitted she had to get herself drunk to be able to endure the group sex sessions Hefner wanted.
“I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it," she wrote.
Hefner's 'black book'
According to Bridget Marquardt, Hefner had a journal - which she described as a 'black book' - in which he would keep track of who was having sex with him and when, alleging he would sometimes use it as a way to call out 'bunnies' who were refusing to have sex based on reasons like being on their period.
"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."
Playboy mansion curfew and punishment
Hefner apparently had a strict 9.00pm curfew for all those living in the property to ensure they wouldn't be out cheating on him.
"We had to be home by 9.00pm," former girlfriend Izabelle St. James told Fox News Digital. "Hef didn't want girls to go out and party without him. I suppose he didn't want us to have the opportunity to be unfaithful.”
And if you missed the cut-off time? Well, he apparently forced the women to sleep on the lawn, according to former Playboy model Jenna Bentley.
The one lipstick shade banned by Hefner
According to several accounts of women living under the roof of the infamous mansion, Hefner had strict rules and regulations about appearance, including what clothes his 'bunnies' could wear, the colour of their hair, and even what lipstick they put on.
Platinum blonde hair was a non-negotiable, with Crystal shockingly revealing she was left with 'blisters' on her scalp from bleaching it so much.
And, bizarrely, Hefner apparently had a vendetta against red lipstick.
“Among the many unspoken rules at the mansion, the red lipstick rule was one of the more notorious," Madison revealed in her book. "I'm not over-exaggerating here.
"Hef absolutely despised red lipstick and wouldn't allow his girlfriends to wear the colour.”
Topics: Celebrity, Hugh Hefner, Playboy, Sex and Relationships
Chloe Rowland