Celebrity2 min(s) read
Ex-Playboy bunny reveals strict bedroom rules that Hugh Hefner demanded she follow at all times
Holly Madison, a former girlfriend of Hugh Hefner, has lifted the lid on one of the more disturbing realities of life inside the Playboy Mansion. The 45-year-old reality star, who dated Hefner when she was just 22 and he was 75, spoke openly about the strict and unsettling rules she and the other women were expected to follow.
Known for her time on The Girls Next Door, Madison has never shied away from discussing her experience as one of Hefner's live-in girlfriends. In her 2015 book Down the Rabbit Hole, she revealed that Hefner expected all his girlfriends to sleep with him before bed every night. On top of that, group sexual activity was often expected. "If it was just me and him, it was a lot more normal than you would think," she admitted.
Strict rules on grooming and exclusion
Speaking to the Call Her Daddy podcast in 2021, Madison shared one of the Playboy founder’s more unsettling preferences. “He would get mad if somebody wasn’t shaved,” she said. “He liked vaginas to look a certain way,” clarifying that he preferred “inies not outies.” According to Madison, one girl wasn’t even invited back because she had an “outie.”
She also revealed that Hefner would take Viagra before any sexual encounters. “He was on top the first time, but he was always lying down every other time that I remember,” she said when describing his preferred sex position.
Sex, silence and isolation inside the mansion
Madison said her encounters with Hefner were far from satisfying, adding that she never had an orgasm during any of their sessions. “It was too messed up,” she explained, agreeing with host Alex Cooper’s comment that the whole setup felt “fully transactional.”
“In the moment, you’re like, this is, it’s almost like your job. And just messed up like drunk and high,” Madison said, reflecting on how detached the experience made her feel. She addressed criticism that she knew what she was signing up for by moving into the mansion, saying, “I absolutely did not.”
“I thought I kind of had a hazy idea of what living at the mansion would be before I moved in, but nobody breaks it down for you,” she explained. Comparing it to Fifty Shades of Grey, Madison said there was no contract or clear agreement. “Nobody really wants to help anybody out – everybody wants a centerfold,” she added, suggesting competition for attention and financial gain kept the women isolated from one another.