Former Playboy model Holly Madison made very sad admission about ‘gross’ reality of her relationship with Hugh Hefner
Topics: Playboy, Sex and Relationships, Hugh Hefner
Simon Fearn
Featured Image Credit: Denise Truscello/WireImage
Topics: Playboy, Sex and Relationships, Hugh Hefner
Hugh Hefner’s ex-girlfriend has lifted the lid on being pressured into things she ‘didn’t want to do’ while living in the Playboy Mansion.
Since the Playboy Magazine founder’s death in 2017, former models have increasingly come forward with heartbreaking and disturbing accounts of what it was like to be in his orbit, with Madison once describing the Playboy Mansion as like ‘a cult’ and ‘very Stockholm syndrome’.
Kendra Wilkinson, who started dating Hefner when she was 18 and he was 78, recently revealed she had to ‘go through a lot of therapy’ after their relationship ended, saying it left her with ‘unhealthy thoughts’ and ‘a little bit of a problem when it comes to thinking about sex’.
Madison started dating Hefner when she was 21 and he was 75. They were together for seven years from 2001 to 2008, though Hefner had multiple girlfriends during this time.
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Opening up on A&E’s Secrets of Playboy back in 2022, Madison said Hefner was incredibly controlling about the way she looked.
She said: “I got to a point not too far into my time there… where I kind of broke under that pressure and being made to feel like I needed to look exactly like everybody else.
"My hair was really long naturally, and I was just like, 'I’m gonna go chop my hair off so I can at least look a little different'."
Hefner ‘flipped out’ at her over the style choice, cruelly telling her the haircut made her ‘look old, hard and cheap’."
She said: “I remember there were times probably within the first couple years I lived there when I felt like I was just in this cycle of gross things and I didn’t know what to do.”
Her hair wasn’t the only thing Hefner yelled at her over, having also lashed out over her choice of lipstick.
Madison explained there was an unsettling reason why he didn’t want Playboy models wearing red lipstick.
Speaking on the Ahead of the Curve with Coco Mocoe podcast in 2023, Madison said ‘new girls’ could wear what lipstick they liked, but Hefner started exerting more and more control the longer they stayed in the Playboy Mansion.
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She explained: “I think it was a control tactic, but also, when I was brand new, I wore red lipstick out a couple of times, and he didn't say anything about it, because when you were the new girl in the group, you were always treated well.
"Somebody said, like, the higher up you are in a cult the worse you're treated because they want the new people to bond and feel into it.
"It wasn't a big deal until, like, six months into it, when I was living in his bedroom and I was the main girlfriend, that he felt like he had the leeway to yell at me over it."
Detailing why Hefner disliked red lipstick, Madison sickeningly said he thought it was a choice made by ‘older mature women’ which wasn’t ‘the barely legal thing anymore’, claiming he preferred women to appear ‘skimpy and fresh-faced and very young looking’.