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Everything Playboy bunnies have claimed about sex with Hugh Hefner as Holly Madison reveals ‘disgusting’ act she ‘hated’ doing

Home> Entertainment> Celebrity

Published 16:00 5 May 2025 GMT+1

Everything Playboy bunnies have claimed about sex with Hugh Hefner as Holly Madison reveals ‘disgusting’ act she ‘hated’ doing

Many women have come forward with details of the strict set of rules they had to abide by while under Hefner's roof

Jess Hardiman

Jess Hardiman

The Playboy Mansion was more than just a home for Hugh Hefner, who used the sprawling property for the lavish parties that became as well-known as the magazine behind it all.

Over the years, it became a hotbed of activity - literally - as Hefner welcomed various girlfriends to live alongside one another.

In the years since his death, many women have come forward with details of the strict set of rules they had to abide by while under his roof.

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But while you may have heard about the mandatory sex parties, what else has been said about what it was really like being a girlfriend at the mansion?

(David Klein/Getty Images)
(David Klein/Getty Images)

Holly Madison

Speaking on Owen Thiele’s In Your Dreams podcast last week, Madison opened up about the mandatory sex parties that the Playboy Mansion became famous for.

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"Well, it’s a very different story between when we were just by ourselves than with everybody else in the room," she explained, adding: "Everybody else in the room, no. That was disgusting. I hated it.

"I made it very known I hated it."

Kendra Wilkinson

Wilkinson also has some less-than-fond memories of nights of group sex at the mansion.

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"I was usually very very drunk doing those evenings, I tended not to care about much until the next day," she wrote in her 2010 book Sliding Into Home.

"I had to be very drunk or smoke l lots of weed to survive those nights.

"At about the minute mark, I pulled away and it was done. It was like a job. Clock in, clock out. It’s not like I enjoyed having sex with him."

Bridget Marquardt

On the Girls Next Door podcast, Marquardt said Hefner had a 'black book' to keep tabs on all the girlfriends.

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"The black book kept track of a few different things,” she 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."

Both she and Madison had heard other girlfriends called out if they weren't playing ball, with the pair remembering: "He’d be like, ‘Oh, you’ve been on your period for three weeks.'"

Marquardt also said Hefner's room was incredibly chaotic, and that 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," she said, with Madison agreeing it was 'hoarder-style'.

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Hefner with Holly Madison, Bridget Marquardt and Kendra Wilkinson in 2004 (Frazer Harrison/Getty Images)
Hefner with Holly Madison, Bridget Marquardt and Kendra Wilkinson in 2004 (Frazer Harrison/Getty Images)

Crystal Hefner

Hefner's last wife Crystal admitted that sex was 'odd and robotic', saying in her book Only Say Good Things: Surviving Playboy and Finding Myself: "This was a well-oiled and well-practiced sequence of events.

"One that went the same exact way every time. Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pyjamas.”

She said the sex was never 'fun' or sexy', and that Hefner seemed 'less sex-savvy' than some of the teenage boys she had 'been with years ago'.

“The dimming of the lights," she wrote. "The music. The porn. Passing the pot. And then the sex.”

Sondra Theodore

Theodore, who was Hefner’s girlfriend between 1976 and 1981, appeared in A&E’s Secrets of Playboy docuseries, explaining how their relationship started off fairly normally – only for it to escalate with Hefner’s growing success.

"He scared me a lot at the end because you couldn't satisfy him - he had to have more and more and more," she said.

"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."

Theodore said that Hefner had cameras in his bedroom – a claim many other girlfriends have also echoed – and that, if someone objected, he would only pretend to turn them off.

Hefner with Sondra Theodore in the 1970s (Images Press/IMAGES/Getty Images)
Hefner with Sondra Theodore in the 1970s (Images Press/IMAGES/Getty Images)

Kristina and Karissa Shannon

Twins Kristina and Karissa Shannon recalled in the A&E docuseries how having sex with Hefner was ‘like having sex with your grandpa’.

Kristina recalled them being given a pill that immediately made them feel ‘the most inebriated’ they’d ever felt, before enaging the two of them in sexual activity.

"We had never done a threesome together before, we would never want to,” she said. They also said multiple women caught chlamydia at the house as Hefner wasn’t willing to use protection.

Stefon Tetenbaum

Tetelbaum may not be one of the girlfriends, but as Hefner’s former valet, he still saw a lot inside the house.

He also featured in A&E’s docuseries, remembering how he had to retrieve used sex toys before getting the bedroom ready for the next round.

"I had to put on rubber gloves and pick up the dildos from the floor and put them in a special bucket," he said. "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."

As for Hefner taping those bedroom antics, Tetenbaum added: “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."

Featured Image Credit: David Klein/Getty Images

Topics: Hugh Hefner, Playboy, Sex and Relationships

Jess Hardiman
Jess Hardiman

Jess is Entertainment Desk Lead at LADbible Group. She graduated from Manchester University with a degree in Film Studies, English Language and Linguistics. You can contact Jess at [email protected].

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@Jess_Hardiman

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