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Holly Madison details ‘really weird’ group sex nights with Hugh Hefner at the Playboy mansion

May 9, 2026
in News
Holly Madison details ‘really weird’ group sex nights with Hugh Hefner at the Playboy mansion

Holly Madison called having group sex with her ex Hugh Hefner “a really weird scene.”

During a recent appearance on Kristin Cavallari’s podcast “Let’s Be Honest,” the former reality star shared what actually happened when the Playboy founder invited other women to join them in the bedroom.

“Yeah, kind of like taking turns and then the girls who weren’t active with him were kind of like acting like they were active with the other girls, but not really,” she recalled, explaining that “nobody liked it and everybody tried to just get it done as fast as possible.”

Holly Madison and Hugh Hefner.
Holly Madison, seen here in 2006 with Hugh Hefner, was not a fan of group sex nights at the Playboy Mansion. WireImage
Holly Madison.
The former Playmate called it “a really weird scene.” holly madison/ instagram

“It would be kind of silhouetted because you’d have, like, these giant screens of porn going and it would be just girls like talking s–t with each other,” she added.

However, one-on-one nights were far more pedestrian and “very suburban.”

“(It was) us watching a movie or he’s doing a crossword puzzle, and I’m reading.”

Madison gained fame by starring in “The Girls Next Door” and its spinoff, “Holly’s World.”

Hugh Hefner and Holly Madison.
Madison, pictured in 2006, said that “nobody liked it and everybody tried to just get it done as fast as possible.” Getty Images
Holly Madison and Hugh Hefner.
The former reality star added that one-on-one time with Hefner was “very suburban.” WireImage

She, Bridget Marquardt and Kendra Wilkinson were Hefner’s three main “girlfriends” for many years.

Hefner died in 2007 at the age of 91.

Last year, Madison, 46, stressed how much she abhorred group sex nights.

“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it,” Madison said on the “In Your Dreams” podcast.

Hugh Hefner poses with Kendra Wilkinson (L) Bridget Marquardt and Holly Madison.
Madison was one of Hefner’s three main “girlfriends” along with Kendra Wilson and Bridget Marquardt. (Photographed here in 2004). Getty Images
Holly Madison.
The “Down the Rabbit Hole” author, snapped in 2024, has said her undiagnosed autism played a part in her relationship with Hefner. GC Images

In 2002, the former Playmate described her sex life with the geriatric Hefner as “hell” and “traumatic.”

“He wouldn’t move. He would be like a bump on the log in the middle of the bed,” she said on the podcast, “Girls Next Level.”

In a 2025 interview with Page Six, the “Down the Rabbit Hole” author revealed that she believes her undiagnosed autism made her susceptible to “falling in love” with Hefner, more than five decades her senior, and living at the Playboy Mansion, where she was expected to sexually perform at any hour.

Madison shares two children with her ex, Pasquale Rotella.

The post Holly Madison details ‘really weird’ group sex nights with Hugh Hefner at the Playboy mansion appeared first on Page Six.

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