Former Playboy model and reality TV star Holly Madison is opening up once again about her time with the late Hugh Hefner—this time getting candid about their private life behind the gates of the iconic Playboy Mansion.
Now 45, Madison recently appeared on the Podcrushed podcast hosted by Owen Thiele, where she didn’t shy away from the more uncomfortable aspects of her relationship with the Playboy founder, who passed away in 2017 at the age of 91.
“It Was Disgusting. I Hated It.”
In one of the podcast’s more revealing moments, Madison spoke bluntly about her experience with group sex during her years with Hefner, calling it something she “hated” and made clear she was never comfortable with.
“When it was just the two of us, it was a completely different experience than when other people were involved,” she said. “Group sex? No. That was disgusting. I hated it. I made it very known I hated it.”
Addressing the Age Gap
Madison also touched on the 53-year age difference between her and Hefner, noting that it didn’t impact their one-on-one intimacy as much as people might expect.
“If it was just me and him, it was a lot more normal than you would think,” she shared, responding to the host’s skepticism about what “normal” could look like in such a mismatched relationship. “Nobody believes that, but it’s true.”
Online Trolling and Hefner’s Appearance
Madison said she was often mocked online during their relationship, particularly with crude comments about Hefner’s age.
“There was a time I couldn’t post anything without someone commenting, ‘Oh, old balls,’” she said. “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
She also revealed that their bedroom time was always in the dark. “We always had the lights off. I mean, there’s a saying: ‘All cats are gray in the dark,’” she joked.
Life Inside the Mansion
Madison dated Hefner from 2001 to 2008 and has been open in the past about feeling pressured to participate in sexual situations she was uncomfortable with. On the podcast, she shared more strange details about life inside the Playboy Mansion—including the presence of odd items around the estate.
“There were trays everywhere—in bathrooms, by the pool, on the tennis courts—filled with Kleenex, Pepto-Bismol, Vaseline, baby oil, sunscreen,” she recalled. “Basically, anything that could be used as makeshift lube. It was weird.”
A Complicated Legacy
Despite her negative experiences in the relationship, Madison clarified that she never resented the modeling side of her Playboy involvement.
“I 100% enjoyed posing for the magazine,” she said. “I always wanted to be in Playboy. I even worked behind the scenes producing Playmate pictorials for a couple of years, and that was actually a super fun experience. So, it’s very multifaceted for me.”
Madison continues to speak out about her time at the mansion, offering a nuanced look at what life was really like behind the glossy covers and curated images of the Playboy brand.