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'I Hated It!': Holly Madison Goes Off on 'Disgusting' Group S-- With Hugh Hefner at Playboy Mansion

holly madison disgusting group experience
Source: MEGA

Holly Madison opened up about having a group s-- with Hugh Hefner, calling it 'disgusting.'

May 5 2025, Published 7:50 a.m. ET

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Holly Madison isn’t holding anything back when it comes to her wild years at the Playboy Mansion.

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The former reality TV star opened up about one thing she couldn’t stand during her relationship with Playboy founder Hugh Hefner.

"Well, it’s a very different story between when we were just by ourselves than with everybody else in the room," she explained on the “In Your Dreams” podcast.

"Everybody else in the room, no," she said bluntly, referring to the infamous group s-- sessions. "That was disgusting. I hated it. I made it very known I hated it.

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holly madison hugh hefner relationship truth
Source: MEGA

Holly Madison called group s-- at the Playboy Mansion 'disgusting.'

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Despite the 53-year age gap between her and Hefner — who passed away in 2017 at 91 years old — Madison said their one-on-one moments were actually more typical than most would expect.

"If it was just me and him, it was a lot more normal than you would think," she shared.

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The Bunny House alum then got real about the judgment she’s faced for her past with Hefner.

"There was a time when I couldn't post anything [on social media] without some dumba-- in the comments [being] like, 'Oh, old b----,'" she stated. "Maybe some people's b---- do get old and nasty, but I've never seen such a thing."

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holly madison playboy group sex comments
Source: MEGA

The reality star said she was much more comfortable when it was just her and Hugh Hefner.

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She noted that the lights were always off during their intimate moments, so she couldn’t exactly confirm any details.

"I mean, there's a saying: 'All cats are gray in the dark,'" she teased.

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Madison, who dated Hefner from 2001 to 2008, has been open for years about how uncomfortable she felt being pressured into group s-- situations with other women in the mansion.

"They would have these trays everywhere, like in every bathroom, out on the tennis courts, by the pool, and it would be a tray with Kleenex, Pepto Bismol, Vaseline, baby oil, sunscreen — any kind of makeshift lube,” she previously told People. “It was weird.”

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playboy secrets holly and crystal reveal all
Source: MEGA

Fans used to mock Holly Madison online about being with an older man.

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“My experiences that played with the negative parts of it are more related to the relationship and the relationship dynamics, both with Hef and some of the other girls,” she explained. “I 100 percent enjoyed posing for the magazine. I was always a fan of the pictorials. I always wanted to be in Playboy. And I even worked at the studio producing the playmate pictorials for a couple of years, and that was a super fun experience. So, it's very multifaceted for me.”

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Even the businessman’s last wife, Crystal Hefner, came forward with her own shocking claims. Crystal met Hef when she was 21, and despite their 60-year age gap, they tied the knot five years later. In her book Only Say Good Things: Surviving Playboy and Finding Myself, she recalled her own bizarre experiences in the mansion.

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crystal hefner playboy mansion memoir
Source: MEGA

Hugh Hefner’s last wife, Crystal Hefner, also revealed dark details in her memoir.

"This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time,” she wrote. “Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas. The dimming of the lights. The music. The p---. Passing the pot. And then the s--.”

She added, [It was] "like Hef was just going through the motions of something that had once been fun and s---. Or maybe it was never fun and s---.”

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