Former Playboy Bunny Holly Madison reveals most 'disgusting' thing she did with Hugh Hefner: 'I hated it.'

A former Playboy bunny has previously spoken out about one aspect of her relationship with Hugh Hefner that she described as “disgusting” and admitted she “hated” during her time living at the Playboy Mansion.

Holly Madison was in her early 20s when she began dating Hefner, who was 53 years older than her. Their relationship lasted from 2001 to 2008, during which Hefner was also involved with other girlfriends, including Bridget Marquardt and Kendra Wilkinson.

Over the years, Madison has shared a number of insights into life inside the mansion, including strict rules the women were expected to follow. One of the most controversial expectations involved group sex, which she discussed on Owen Thiele’s In Your Dreams podcast.

Not your typical house rules

She explained that while intimacy between just her and Hefner was a “very different story,” the group situations were something she found deeply uncomfortable, saying: “I hated it. I made it very known I hated it.” She added that it felt “really ‘disgusting’” when others were present.

Madison contrasted this with their private moments, saying: “If it was just me and him, it was a lot more normal than you would think.”

Reflecting on their relationship, she said the large age gap didn’t personally bother her, though it often drew criticism from others. She recalled: “I feel like there was a time when I couldn’t post anything without some dumbass in the comments like, ‘Oh, old balls,’ or something like that,” before adding, “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”

She also revealed that they would often keep the lights off, joking: “I mean, there’s a saying: ‘All cats are grey in the dark.’”

In a previous interview with BuzzFeed in 2015, Madison said the group encounters followed a strict routine. “It was always Wednesdays and Fridays after the club. It was always exactly the same because that’s just how he likes to live his life,” she said.

According to Madison, participation was expected from everyone living at the mansion. “They knew it was kind of a quote-unquote requirement for living there, and expected,” she explained, adding that it “had kind of a chore vibe.”

Madison reveals Hefner's controlling tendencies

She has also claimed Hefner was highly controlling about appearance. Speaking on Secrets of Playboy, she said the pressure to conform eventually became overwhelming: “I got to a point not too far into my time there… where I kind of broke under that pressure and being made to feel like I needed to look exactly like everybody else.”

Madison said she tried to assert some individuality by cutting her hair, but claimed Hefner reacted badly, telling her the new look made her “look old, hard and cheap.”

Looking back, she described feeling stuck during those early years, saying: “I remember there were times probably within the first couple years I lived there when I felt like I was just in this cycle of gross things and I didn’t know what to do.”

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