
A series of strict rules governed the lives of the women there, with them having to be home by the 9.00pm curfew, not have relationships with anyone else and line up to collect their ‘allowance’ money from him.
According to those who lived in the mansion an unwritten rule was no wearing red lipstick.
Beyond their behaviour the women’s appearance was also subject to Hefner’s rules which meant having blonde hair and avoiding red lipstick since the Playboy mogul didn’t like it.

Holly Madison, one of Hefner’s ‘girlfriends’ at the Playboy mansion, said he didn’t like women wearing red lipstick (J. Merritt/FilmMagic)
“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,” Madison explained.
“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.”
Madison said that she thought Hefner banned red lipstick because he wanted the women at his mansion to look ‘skimpy and fresh-faced and very young looking’, and associated shades of red with ‘older mature women’.
After he died in 2017 may of his former ‘girlfriends’ spoke out about what things were really like at the Playboy mansion.

Madison felt it was a control tactic (Victor Spinelli/WireImage)
Apparently the place was a bit of a tip, especially when it came to the carpets as they’d go for years without being washed or cleaned.
One woman, Izabella St. James, said that when Madison became Hefner’s ‘girlfriend number one’ and brought her dogs with her their mess wouldn’t be cleaned off the floor.
There were also descriptions of the mattresses in the various rooms provided for the women being ‘old, worn and stained’.
Hefner’s widow Crystal described the place like a ‘prison’ and security there ‘couldn’t let her leave’, while she said that if he changed his meal from a tepid bowl of soup to a BLT she knew that was a signal that he was expecting to have sex that night.
Multiple women who stayed there said that Hefner also kept ‘disgusting’ books where he tallied how many times the women at the mansion had slept with him.