Former Playboy Bunny shares disturbing details of a ‘disgusting’ encounter with Hugh Hefner

Holly Madison has candidly discussed the sexual relationship she had with Hugh Hefner and highlighted an aspect she particularly disliked.

The model dated Playboy founder Hugh Hefner from 2001 until 2008, despite the significant age difference of 53 years. Throughout this period, Madison has frequently shared details about their intimate life.

Madison has been open about the highs and lows of residing in the Playboy Mansion and her connection with the late publisher of the magazine.

Hefner passed away at 91 on September 27, 2017.

At 45, Madison appeared on an episode of the In Your Dreams podcast in May, where she revealed her distaste for a particular act.

Regarding the age disparity, she commented: “If it was just me and him, it was a lot more normal than you would think.”

Madison further mentioned her aversion to group encounters with Hefner and others.

She elaborated: “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.”

During the podcast, Madison also addressed the ridicule and online harassment due to her relationship with Hefner.

She mentioned: “There was a time when I couldn’t post anything [on social media] without some dumba** in the comments [being] like, ‘Oh, old balls.’”

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

She also disclosed that they often kept the lights off, referencing the saying, ‘all cats are gray in the dark’.

Although their physical relationship seemed satisfactory, Madison has reflected on the emotional aspects of being with Hefner.

In retrospect, she acknowledged that she ‘didn’t actually know him that well’, even though she engaged in activities she believed connected them.

In an interview with the New York Post, the Holly’s World star revealed: “I thought I was connecting with [Hefner], 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.”

Reflecting on her past, Madison views herself as ‘somebody who was young and impressionable and just kind of in a fog almost’.