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

A former Playboy bunny has spoken about an aspect of her past relationship that she said she found “disgusting”.

Holly Madison dated Hugh Hefner from 2001 to 2008, a period during which she also lived at the Playboy Mansion.

Their relationship drew frequent attention because Hefner was 53 years older than Madison, and she has said the scrutiny often missed what the relationship was actually like.

Madison has previously shared how tired she became of people fixating on the age difference whenever she posted online.

“There was a time when I couldn’t post anything [on social media] without some dumba** in the comments [being] like, ‘Oh, old balls’,” she told the In Your Dreams podcast.

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

However, Madison said there was one specific situation with Hefner that she strongly disliked.

She said the dynamic changed significantly when the sexual encounters involved other people, referencing group sex with Hefner and his other girlfriends.

“If it was just me and him, it was a lot more normal than you would think,” she said.

“It’s a very different story between when we were just by ourselves than with everybody else in the room.

“Everybody else in the room, no. That was disgusting.

“I hated it. I made it very known I hated it.”

Madison also described broader issues she felt existed in the relationship, including her belief that she never truly knew Hefner as well as she thought she did.

“I thought I was connecting with [Hefner],” she said. “When really I was just somebody who had trouble connecting with people my whole life.

“And I’d met somebody who was like a master manipulator.”

Hefner died in 2017 aged 91. In the years following his death, multiple women publicly alleged abuse.

After he died, Playboy released an open letter that positioned the company as distinct from Hefner’s legacy.

It read: “Today’s Playboy is not Hugh Hefner’s Playboy. Today, our organization is run by a workforce that is more than 80% female, and together we are building upon the aspects of our legacy that have made a positive impact, including serving as a platform for free expression and a convener of safe conversations on sex, inclusion and freedom.

“We will continue to confront any parts of our legacy that do not reflect our values today, and to build upon the progress we have made as we evolve as a company so we can drive positive change for you and our communities.”