Holly Madison Details “Weird Scene” of Group Sex Nights With Hugh Hefner in Playboy Mansion

Published: May 09 2026

Holly Madison is reminiscing about one of her most unsettling experiences from her days in the Playboy mansion. Almost two decades after leaving Hugh Hefner's residence, she recounted the group sex she, Kendra Wilkinson, and Bridget Marquardt had to engage in alongside the Playboy founder.

"At first, we'd go out twice a week, and it would always be after our nights out," Madison told Kristin Cavallari in a May 5 appearance on the Let's Be Honest podcast. "There wasn't really an order. It was the same every night but kind of not. It was just, ew."

Holly Madison Details “Weird Scene” of Group Sex Nights With Hugh Hefner in Playboy Mansion 1

Madison recalled that the women residents of the mansion would "take turns" having sex with Hefner, while "the girls who weren't active with him were pretending to be active with the other girls, but not really."

"It was a weird scene. You'd have these giant screens of porn going, and it would just be girls talking trash to each other," said the 46-year-old mother of two children with ex-partner Pasquale Rotella. "It was a nightmare."

Fortunately, with the success of the Playboy reality series, which premiered in 2005, the "compulsive sex nights" came to an abrupt end as the group stopped going out as frequently.

"There was no discussion," Madison noted. "That's how it evolved. Me, Bridget, and Kendra were all on the same page that we just didn't want to do that anymore. Nobody had to say anything. We were just like, 'OK, we're not going out anymore so nobody's going to initiate it.'"

During her final years in the mansion, Madison - who identified as Hefner's No. 1 girlfriend - admitted that she had sex with him "very rarely."

"It would just be us watching a movie or he's doing a crossword puzzle and I'm reading," she explained. "It was very suburban."

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