Holly Madison discussed her sex life with Hugh Hefner during her time at the Playboy Mansion on the May 2 episode of the In Your Dreams podcast. She expressed her disdain for group sex, stating it was “disgusting” and that she made her feelings clear. However, she found one-on-one time with Hefner, despite their 53-year age gap, to be more “normal” than expected. Madison noted that while she enjoyed posing for Playboy and worked in production for pictorials, her experiences were complex, often involving pressures within the relationship dynamics and group scenarios.
- Holly Madison discussed her intimate life with Hugh Hefner while residing in the Playboy mansion, noting that while she found group sex “disgusting,” her private moments with Hefner were “a very different narrative.”
- “When it came to others in the room, no. That was repugnant. I made it clear that I hated it,” she remarked during her May 2 appearance on the In Your Dreams podcast.
- Madison was involved with Hefner from 2001 until 2008.
Holly Madison is revealing insights about her intimate experiences with Playboy founder Hugh Hefner and expresses her disdain for situations involving multiple partners.
The former star of Girls Next Door, now 45, appeared on the May 2 episode of the In Your Dreams podcast, chatting with host Owen Thiele about her time at the Playboy Mansion as one of Hefner’s girlfriends.
“The dynamic was completely different when it was just the two of us compared to when others were present,” she explained.
“With others present, absolutely not,” she added, referring to group sex. “That was appalling. I made my feelings on that very clear.”
Madison also mentioned that the 53-year age difference with Hefner—who passed away in 2017 at age 91—did not negatively affect their intimate relationship. “When it was just us, it felt more conventional than you might think,” she disclosed.
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After Thiele expressed skepticism about the normalcy of it, Madison responded, “Nobody believes that.”
“There was a phase where I couldn’t share anything on social media without some clueless person commenting ‘Oh, old balls,'” the host of Girls Next Level joked. “Some people’s experiences may vary, but I’ve never encountered that.”
She did clarify that she and Hefner preferred to keep the lights dimmed, so she couldn’t assert her views with absolute certainty.
“There’s a saying: ‘All cats are gray in the dark,'” she playfully noted.
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Madison, who was romantically linked with Hefner from 2001 to 2008, has previously admitted feeling pressured to engage in sexual scenarios with Hefner, particularly with other women.
In a March discussion with PEOPLE regarding her true crime series Lethally Blonde, which highlights the experiences of victims in the adult entertainment industry, she reminisced about some of the oddities she observed around the Playboy Mansion.
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“They had trays of items all over, like in every bathroom, on the tennis courts, and by the pool, which included tissues, Pepto Bismol, Vaseline, baby oil, and sunscreen — basically every type of makeshift lubricant,” she described. “It was bizarre.”
“My negative experiences seemed more tied to relationship dynamics, both with Hef and some other women,” Madison elaborated. “I absolutely loved posing for the magazine. Being in Playboy was a dream of mine, and I even spent a couple of years working at the studio producing playmate pictorials, which was incredibly enjoyable. So, my experience is quite complex.”