Holly Madison reveals what she hated with Hugh Hefner and opens up about their relationship struggles.

Holly Madison is now speaking out about her years in the Playb0y Mansion, revealing a part of her s3x life with Hugh Hefner that still makes her uncomfortable. Madison dated Hefner from 2001 to 2008, and she often looks back on their relationship and what life inside the mansion was really like.

She joined the In Your Dreams podcast in May and opened up about a s3xual act she “hated” throughout her time with Hefner. Madison said, “If it was just me and him, it was a lot more normal than you would think,” regarding their 53-year age gap. However, her tone changed when she described the group encounters that often happened.

Earlier this year, Hefner’s widow, Crystal, also shared unexpected details about her own s3x life with the Playb0y founder.

Madison Says Group S3x Left Her Feeling Sick

Holly Madison and Hugh Hefner (Photo Via X)
Madison was clear about why those moments still bother her. “It’s a very different story between when we were just by ourselves than with everybody else in the room.” She explained that the dynamic changed the moment others joined, and she hated the group s3x. “Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it,” she said.

Madison also discussed the online hate she received due to their relationship. She said people constantly joked about his age whenever she posted anything. “There was a time when I couldn’t post anything without some dumba** in the comments like, ‘Oh, old balls,’” She added jokingly, “Maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”

She said they usually kept the lights off and used the phrase “all cats are gray in the dark” to deal with the age difference.

Even though things sometimes worked physically, Madison said the emotional connection was never there.

In an interview with the New York Post, she said she thought she knew Hefner well, but now realizes she didn’t. She described herself as “young and impressionable” and called Hefner “a master manipulator.”

Looking back, Madison said she felt like she was living in a delusion during that time and didn’t fully understand what was happening until much later.