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Ex-Playboy model Holly Madison described ‘hellish’ sex routine with Hugh Hefner and his other girlfriends
Home>Entertainment>Celebrity
Published 17:29 20 May 2025 GMT+1

Ex-Playboy model Holly Madison described ‘hellish’ sex routine with Hugh Hefner and his other girlfriends

Hefner's former girlfriend has opened up about the reality of living in the Playboy Mansion

Jen Thomas

Jen Thomas

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Featured Image Credit: Denise Truscello / Contributor / Getty

Topics: Playboy, Sex and Relationships, US News

Jen Thomas
Jen Thomas

Jen Thomas is a freelance music, entertainment, and news journalist, as well as a radio presenter for Virgin Radio and Magic Musicals.

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@jenthomasradio

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Life in the Playboy Mansion wasn't all it was cracked up to be, according to one of Hugh Hefner's many girlfriends.

With more and more grim stories coming to light in recent times about the Playboy Mansion, Holly Madison has opened up about the realities of life living alongside the magazine boss' multiple other girlfriends, and the antics that he wanted the Playboy playmates to partake in.

Hefner, died at the age of 91 back in 2017, became famous for having multiple girlfriends who lived with him in his lavish Beverly Hills home - but things weren't as idyllic as they seemed.

It has previously been revealed that weird items were often dotted around the mansion, and there were strict expectations of what the 'playmates' would do.

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Now, Holly has revealed all in an episode of her new podcast Girls Next Level, talking alongside another former girlfriend of Hefner, Bridget Marquardt.

Holly Madison has opened up about life with Hugh Hefner in the Playboy Mansion (Denise Truscello / Contributor / Getty Images)
Holly Madison has opened up about life with Hugh Hefner in the Playboy Mansion (Denise Truscello / Contributor / Getty Images)

'It was like hell'

The pair described sex with Hefner as a 'chore' that they 'tried to check off as quickly as possible'.

“None of the females were into it — like, sorry to burst the bubble," Holly, who dated Hugh in the early 2000s, said.

She went on: "We thought of it as a chore that we had to do or else we’ll get kicked out of the house, and everybody just wanted to make it go by as quickly as possible.

"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.... It was like hell."

Former girlfriends have opened up about their experiences with Hugh Hefner (Robert Mora / Staff / Getty Images)
Former girlfriends have opened up about their experiences with Hugh Hefner (Robert Mora / Staff / Getty Images)

‘Disgusting act'

Holly said her one-on-one time with Hefner was fine, but she hated it when everyone else was in the room with them.

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

"I made it very known I hated it. You’re literally sitting there naked having sex in front of a group of people who hate you and talk s**t about you while you’re having sex, and you can hear it."

She isn't the only girlfriend to speak out, either.

Marquardt also said that Hefner's bedroom was also incredibly dirty, recalling being shocked 'at how messy it was'.

"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.

"Then you get in [his room], and there’s vibrators all over the bed. It was just hoarder-style."

The magazine boss died at the age of 91 back in 2017 (Dan Tuffs/Getty Images)
The magazine boss died at the age of 91 back in 2017 (Dan Tuffs/Getty Images)

'I had to be very drunk'

Another former girlfriend, Kendra Williamson, revealed the lengths she had to go to in order to get through the group sex activities.

She talked about her coping mechanisms in her book, Sliding Into Home.

"I was usually very very drunk doing those evenings, I tended not to care about much until the next day... I had to be very drunk or smoke l lots of weed to survive those nights."

She also described sleeping with Hefner as being 'like a job' and how she handled it: "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."

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