Holly Madison Details ‘Weird’ Group Sex, ‘Taking Turns’ With Late Hugh Hefner

Holly Madison is spilling all about her sex life in the Playboy Mansion.

The former Girls Next Door star, 46, detailed group romps with the late Hugh Hefner during the Tuesday, May 5, episode of the “Let’s Be Honest With Kristin Cavallari” podcast.

“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*** with each other,” Madison said, claiming it was an awkward experience that she and other women rushed through. She added, “It was a really weird scene and nobody liked it and everybody tried to just get it done as fast as possible.”

When asked how the trysts began, Madison — who previously identified as the magazine mogul’s No. 1 girl for seven years — told host Kristin Cavallari, “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.”

Fans got to know Madison and Hef’s other main girlfriends Bridget Marquardt and Kendra Wilkinson when the trio appeared on five seasons of their E! reality series, The Girls Next Door, which debuted in 2005. The sixth and final season premiered in 2009, introducing his future wife, Crystal Harris, as well as twins Kristina and Karissa Shannon. (Crystal has since remarried after Hefner died in September 2017. He was 91.)

“But after we started filming the show, [the group sex sessions] just stopped, which was amazing,” Madison said. “He loved the show. He was like high off the show,” she speculated. “It gave him new relevance, like the ego boost. So he didn’t really feel the need to like, ‘Oh, I have to do these compulsive sex nights to make myself feel wanted and relevant,’ I think.”

Deal of the Day

Need an Easy Spring Outfit? This Bestselling Matching Set Is 53% Off

View Deal

Check our latest news in Google News

Check our latest news in Apple News

(Photo by Ethan Miller/Getty Images)

Madison said the hookups often happened after they went on date nights. While recalling their past, she admitted there was a point in time when things changed, which came as a relief.
“I think me, Bridget, and Kendra were so on the same page that we just didn’t want to do that anymore,” Madison said of how the dynamic evolved over time, noting there was no conversation but rather an overall understanding. “Nobody had to say anything. We were just like, ‘OK, we’re not going out anymore.’”

Madison, now a mom of two, said that toward the end of her relationship with Hefner, 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 shared. “It was very suburban.”

Just For You