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When Madison came home from the salon after a makeover that included shorter hair and red lipstick, Hef reportedly told her, "I hate the whole look.I hate the makeup and I hate the red lipstick." He added, "You look old, hard, and cheap." When Kendra Wilkinson moved in later and appeared before Hef wearing red lipstick, Madison braced herself for his wrath, only for him to tell Wilkinson, "Why, that red lipstick looks absolutely wonderful on you, Kendra! Hef demanded his girlfriends be in by the 9 o'clock curfew each night.Earlier this month, the 41-year-old announced she has a new TV show in the works.

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When Madison told him she doesn't do drugs, she says Hef replied, "Usually I don't approve of drugs, but you know, in the '70s they used to call these pills 'thigh openers.'"4.

Among his bizarre set of mansion rules, Madison writes, were that the girlfriends change into identical flannel pajamas before the bedtime routine.5.

He would watch porn, smoke pot, and jerk off while his girlfriends and whoever else happened to be joining them that night pretended to get it on around him.

Madison says they would take turns pleasuring Hef, but he always finished by himself.

Hef would take photos of his girlfriends and him every night before they went out, then have them delivered to each girlfriend's door the next morning.

The photos "only amplified the massive pressure to always look perfect and cause the girlfriends to spend hours critiquing their appearances," Madison writes.

As for Hef, he moved on from the trio and began dating Crystal Harris.

The two became serious and eventually tied the knot on New Year’s Eve 2012.

She was also involved in a very public relationship with illusionist Criss Angel.

In 2013, Holly’s personal dreams came true when she and her then fiancé Pasquale Rotella welcomed their first child Rainbow Aurora lasted just one season.

Holly admitted she wanted to be married and have children– neither of which Hefner was willing to do.

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