03-05-2025
Hugh Hefner's ex Holly Madison details the 'disgusting' sex acts she 'hated' with the Playboy mogul
Holly Madison has opened up about life as one of Hugh Hefner's girlfriends, and what she did and didn't like about it when they were behind closed doors.
The former The Girls Next Door star dished on her sex life with the Playboy founder and revealed she wasn't crazy about group bedroom activities.
'Well, it's a very different story between when we were just by ourselves than with everybody else in the room,' she said on the In Your Dreams Podcast with Owen Thiele.
'Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it,' she declared.
However their one-on-one time was different.
'if it was just me and him, it was a lot more normal than you would think.'
Regarding the 50-year age different between the Hefner and his bevy of beautiful girlfriends, the reality star said, 'I think everybody has this real horror story of how gross an old man's body must be.'
'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 and look, maybe some people's balls do get old and nasty, but I've never seen such a thing.'
That could be because the lights were out when the two were together and 'All cats are grey in the dark.'
Madison was Hefner's 'number one girlfriend' on TGND from 2001 until she left in 2008.
'This is kind of sad, but when I broke up with him, I was like packing my stuff, and then one day there was like ... I don't know why I'm laughing ... There was a folder set out on my side of the bed because he knows I'm going to look at it. Everybody knew I was the biggest snoop in the house, so I looked at it,' she said.
Madison said she was a snooper because she felt she had 'zero control.'
'You didn't know who was showing up, who was going to be in the bedroom the next day and I just wanted to be prepared,' she explained.
She has also revealed in the past that Hefner controlled her finances and would not allow her to earn any money outside her role at the mansion.
While gathering her things, the influencer said, 'This was very clearly for me to see, my side of the bed, so I look at it and it's his will all printed out, all the details,' she revealed.
'This is who's getting what and blah, blah, blah. He was leaving me $3 million.'
Madison said the gesture was 'kind of sad.'
'I'd already broken it off with him and he was trying to get me to stay, so it was kind of like a lowkey bribe but also sad because he can't sit me down and talk to me about it. It was just like, "Oh, maybe if she sees this,"' the Down the Rabbit Hole author guessed.
Hefner died in 2017 at age 91.
Hefner died in 2017 at age 91; Pictured in Holmby Hills, CA in February 1999
Madison has been able to turn her time at the mansion into a viable career that helps her support herself and her two children with jobs hosting The Playboy Murders and Lethally Blonde.
Her parents, obviously know about her time with Hefner, but her children, Forest, about nine, and Rainbow, about six, don't. She shares her kids with ex-husband Pasquale Rotella.
'They don't know anything about it. They're very sheltered. They go to a very sheltered school. Their dad hates all that stuff, so he doesn't talk about it, but also kids that age have no idea what that is,' she explained.
When it comes to revealing the past, Madison said she isn't sure how she'll break the news to them. 'I mean, you never know with kids how you're going to explain anything until it comes up.'
