Hugh Hefner's former Playboy model GF Holly Madison reveals 'disgusting' sex acts she 'hated' with him

Daily Mail​

04-05-2025

opens up about life as one of the late Hugh Hefner's girlfriends, and what she did and didn't like about what they got up to behind closed doors.
The former reality TV star dished on her sex life with Playboy founder Hefner, who died aged 91 in 2017 from sepsis brought on by an E. coli infection, and revealed she wasn't crazy about group bedroom activities.
On the In Your Dreams Podcast With Owen Thiele, Madison explained: 'Well, 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.'
However, Madison said her one-on-one time with Hefner was different.
She said: 'If it was just me and him, it was a lot more normal than you would think.'
Regarding their 50-year age difference and Hefner's other girlfriends, Madison 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, as she said, 'All cats are grey in the dark.'
Madison was Hefner's 'number one girlfriend' on The Girl Next Door from 2001 until she left in 2008.
She said: '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.'
Madison said she was a snooper because she felt she had 'zero control'.
She added: '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 has also revealed in the past that Hefner controlled her finances and would not allow her to earn any money outside of her role at the mansion.
Too many bunnies: Intimate group activities at the Playboy Mansion were not Madison's thing
When she was gathering her things, Madison 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.
'This is who's getting what and blah, blah, blah. He was leaving me $3million.'
Madison called the gesture 'kind of sad'.
She said: 'I'd already broken it off with him and he was trying to get me to stay, so it was kind of like a low-key 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..."'
Sad times: She called the will incident 'kind of like a low-key bribe' and she would have preferred for the Playboy founder to have sat her down and talked to her about it