Former Playboy Bunny Holly Madison reveals ‘disgusting’ sex act with Hugh Hefner she ‘hated’ doing

Holly Madison once opened up about the ‘disgusting’ thing she ‘hated’ doing with Hugh Hefner during the years she was living at his Californian mansion.

45-year-old Madison was just 22 when she struck up a relationship with Hefner, the Playboy founder who died in 2017.

The pair, who shared a 53-year age gap, were together from 2001 until 2008, though the father-of-four simultaneously favoured other women like Bridget Marquardt and Kendra Wilkinson during this time.

Madison, a former Playboy model and reality TV star, has revealed a slew of details about life in the mansion over the years. These include extreme rules that residents had to abide by, such as not wearing lipstick.

Another legislation Hefner’s girlfriends had to abide by was group sex parties—an activity Madison has previously discussed on Owen Thiele’s In Your Dreams podcast.

Holly Madison detailed a 'disgusting' bi-weekly activity she and other Playboy mansion residents had to partake in (Lawrence Lucier/FilmMagic)

The mother-of-two claimed that while sex was a ‘very different story’ when she and Hefner were alone, it was really ‘disgusting’ when everyone else was in the room.

“I hated it. I made it very known I hated it,” she explained.

Madison noted that her one-on-one time with Hefner was far more 'normal', continuing: "If it was just me and him, it was a lot more normal than you would think."

The Girls Next Door icon continued, claiming her age gap relationship never bothered her, but that she would receive criticism from others.

"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," she told Thiele.

"Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing."

Hugh Hefner and Madison shared a 53-year age gap (Denise Truscello/WireImage)

Madison also used the podcast to clarify how she and Hefner would keep the lights off while having sex, adding: "I mean, there's a saying: 'All cats are grey in the dark.'"

According to the former model, the prolific sex parties always took place on the same two days of the week.

"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 told Buzzfeed in 2015

According to Madison, all of Hugh's girlfriends were required to take part as she explained: "They knew it was kind of a quote-unquote requirement for living there, and expected.

"And it had kind of a chore vibe, I felt."

In 2022, Madison claimed her ex-boyfriend was also extremely controlling about the way she looked.

Madison has detailed her Playboy experiences in books and in various interviews (Instagram/@hollymadison)

Appearing on A&E’s Secrets of Playboy, she explained: “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.

"My hair was really long naturally, and I was just like, 'I’m gonna go chop my hair off so I can at least look a little different'.”

Madison said cutting off her hair allegedly made Hefner ‘flip out’, cruelly telling her the haircut made her ‘look old, hard and cheap’.

She said: “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.”