Former Playboy Bunny reveals the ‘disturbing’ intimate encounter with Hugh Hefner that still haunts her

Holly Madison has candidly discussed aspects of her past intimate life with Hugh Hefner, highlighting one particular element she disliked.

The model was romantically involved with the Playboy founder from 2001 until 2008. Despite a significant age difference of 53 years, Madison has previously shared that they maintained a very active sexual relationship, often providing explicit details.

She frequently reflects on both positive and negative experiences of her time at the Playboy Mansion and her personal relationship with the late Hefner.

Hefner died at the age of 91 on September 27, 2017.

In May, Madison, now 45, appeared on the *In Your Dreams* podcast, where she discussed an action she found ‘disgusting.’

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

However, Madison admitted she ‘hated’ engaging in group sexual activities 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 spoke about the ridicule and trolling she encountered on social media due to her association with Hefner.

She stated: “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 mentioned that they often kept the lights off, referencing the saying, ‘all cats are gray in the dark.’

While things seemed fine physically, Madison has reflected on the emotional aspects of her relationship with Hefner.

In retrospect, she admits she ‘didn’t actually know him that well’ despite participating in activities she believed would connect them.

In a conversation with the New York Post, the former *Holly’s World* star confessed: “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 describes herself as ‘somebody who was young and impressionable and just kind of in a fog almost.’