Hugh Hefner’s ex Holly drops bombshell about sex with Playboy mogul after Kristen Cavallari begs for details

Holly Madison did not hold back about her sex life with Playboy founder Hugh Hefner during a no-holds-barred chat with Kristen Cavallari.

The 46-year-old moved into the infamous Playboy Mansion in 2001, quickly becoming his ‘number one girl’ for seven years, even though she later described the place as isolating and downright ‘cult-like’ in her 2015 memoir.

As the face of the reality hit The Girls Next Door, alongside fellow girlfriends Bridget Marquardt and Kendra Wilkinson, she charmed fans with a picture-perfect life – but behind the cameras, Madison was quietly chafing under Hefner’s strict rules.

By 2008, she had had enough, leaving the mansion when it became clear Hefner would neither marry her nor have children with her.

On Tuesday’s episode of Cavallari’s Let’s Be Honest podcast, the former Playboy Bunny spilled intimate bedroom secrets about the former relationship after she was pressed on how often she was ‘required’ to have sex with him.

‘In the beginning, we would go out twice a week and it would always be after we went out,’ Madison revealed. ‘When the show [Girls Next Door] started filming, we would stop and it was amazing.’

Holly Madison has been candid on a podcast about her sex life with Playboy founder Hugh Hefner. Above, the former couple in 2003

On Tuesday’s episode of Kristin Cavallari’s Let’s Be Honest podcast, the former Playboy Bunny spilled intimate bedroom secrets about the former relationship after Cavallari pressed her on how often she was ‘required’ to have sex with him

She added, ‘Not that we wouldn’t ever go out if it was a special occasion, but we stopped those regular club nights where we would go out every Wednesday and Friday because we were so busy with the show.’

Hefner, Madison explained, ‘loved the show’ and even ‘got high off’ the series.

‘It gave him new relevance like an ego boost, so he didn’t really feel the need to do these compulsive sex nights to make himself feel wanted,’ she added.

‘There was no discussion to stop the nights. It just evolved and we just didn’t want to do it anymore,’ she said.

Cavallari chimed in, ‘And you’ve openly talked about the group sex you guys had to have, explain that whole scene to me, like is it all of the girlfriends and Hef?’

Madison replied, ‘Yeah, kind of like taking turns and then the girls who weren’t (sexually) active with him were pretending to be or acting like they were (sexually) active with the other girls but not really…it was kind of silhouetted…cause there were like giant screens of porn going. 

‘It was a really weird scene and nobody liked it and everybody just tried to get it done as fast as possible.’

Cavallari then asked if Madison was the ‘first or last’ in line of the girls having sex with him during the group nights, as Madison was ‘the main girlfriend.’

‘In the beginning, we would go out twice a week and it would always be after we went out,’ Madison revealed to Cavallari, adding,’When the show [Girls Next Door] started filming, we would stop and it was amazing’

Madison with Hefner, Bridget Marquardt and Kendra Wilkinson on the reality show

‘There wasn’t really an order, but it was kind of the same every night,’ Madison replied, adding, ‘But kind of not.’

Cavallari continued, ‘So even as the main girlfriend, you didn’t have to have sex with him on your own?’

Madison said that was ‘very rarely’ the case.

‘It was just us watching a movie or him doing a crossword puzzle,’ she added.

In a May 2025 appearance on the In Your Dreams Podcast with Owen Thiele, Madison opened up about the 50-year age gap between Hefner, who died in 2017 at age 91, and his bevy of glamorous girlfriends.

‘I think everybody has this real horror story of how gross an old man’s body must be,’ she admitted at the time.

‘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.’

In the same interview, Madison revealed that her two children, Forest, ten, and Rainbow, seven, whom she had with ex-husband Pasquale Rotella, are completely in the dark about her Playboy past with Hefner.

Madison said of the group sex nights: ‘It was a really weird scene and nobody liked it and everybody just tried to get it done as fast as possible’

Madison revealed she ‘rarely’ had to have sex with Hefner one-on-one 

‘They don’t know anything about it. They’re very sheltered. They go to a very sheltered school,’ she said at the time.

‘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 added.

When it comes to eventually revealing her past, Madison admitted she isn’t quite sure how she’ll break the news. 

‘I mean, you never know with kids how you’re going to explain anything until it comes up.’