Holly Madison Spills the Tea on Bizarre Group Sex Nights with Hugh Hefner

“A really weird scene” is how Holly Madison describes her nights of group sex with Hugh Hefner. The former Playmate didn’t hold back during her recent chat on Kristin Cavallari’s podcast, “Let’s Be Honest,” diving into the bizarre dynamics of the Playboy Mansion bedroom.

Madison recounted the awkwardness: “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 painted a picture of discomfort, noting that “nobody liked it and everybody tried to just get it done as fast as possible.”

Picture this: giant screens blasting porn while the women exchanged gossip, all under a surreal glow. “It would be kind of silhouetted,” she added, capturing the oddity of the atmosphere.

In stark contrast, her one-on-one encounters with Hefner were “very suburban.” “(It was) us watching a movie or he’s doing a crossword puzzle, and I’m reading,” she shared, highlighting the mundane reality behind the glitz.

Madison rose to fame on “The Girls Next Door” alongside Bridget Marquardt and Kendra Wilkinson, who were also part of Hefner’s inner circle. The trio became synonymous with the Playboy lifestyle, but behind closed doors, things were far from glamorous.

After Hefner’s death in 2007 at age 91, Madison has been vocal about her disdain for those group sex nights. “Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it,” she declared on the “In Your Dreams” podcast last year.

Back in 2002, she described her sexual experiences with the aging mogul as “hell” and “traumatic.” “He wouldn’t move. He would be like a bump on the log in the middle of the bed,” she lamented on “Girls Next Level.”

In a candid 2025 interview, Madison revealed that her undiagnosed autism may have contributed to her complicated feelings for Hefner, who was over five decades her senior. Living at the Playboy Mansion meant being on call for sexual performances at any hour, a pressure that weighed heavily on her.

Today, Madison is a mother of two with ex-husband Pasquale Rotella, navigating life far removed from the peculiarities of her past in the mansion.