Weird Rules That Hugh Hefner's Girlfriends Had To Follow

Despite the many wild parties at the Playboy Mansion, being a Playboy Bunny doesn't sound like much fun, according to the 2015 memoir "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," written by Holly Madison, one of Hugh Hefner's exes. That was particularly true if, like Madison, you were one of "Playboy" mogul's unhappy live-in employees — or, as he called them, his girlfriends.

In her book, Madison wrote that life as a live-in Bunny and Hef's No. 1 girlfriend made her feel deeply depressed. "Drowning myself seemed like a logical way to escape the ridiculous life I was leading," she wrote, via Buzzfeed. "I just couldn't take my misery anymore." Hef forbade her from seeing a therapist, so she took antidepressants instead. Part of Madison's misery seems to have stemmed from Hefner's penchant for bizarre, highly specific rules about how the Playboy Bunnies should act, what and when they should do what they do, and how they should look.

Hefner even had schedules for the "girls," with a curfew, and had specific nights for group sex (via Cosmopolitan). Referring to the metal gate at the entrance of the Playboy Mansion, Madison wrote in her book (via Cosmo), "Everyone thinks that the infamous metal gate was meant to keep people out. But I grew to feel it was meant to lock me in."

The worst rule: scheduled 'chore vibe' sex

According to Buzzfeed's interview with Madison (pictured) on the occasion of her book release, Hefner would have sex with his girlfriends on Wednesdays and Fridays, after they had gone out to a nightclub, "It was always exactly the same because that's just how he likes to live his life," she said, describing his sex routine. During these biweekly orgies, most of the girlfriends would mime sex with each other, high on quaaludes (Hefner called them "thigh-openers," Madison claims) while one woman had to briefly copulate with the elderly man in the center.

According to other of Hefner's ex-girlfriends, each would take a turn in the sack with Hef with the "main girlfriend" going first (via Cosmopolitan). "It had kind of a chore vibe, I felt," Madison told Buzzfeed. Girls involved would simply stand there and put on a show to create a fantasy that something was going on, and since Hef couldn't hear well out of one ear, Madison could hear the women talking and gossiping while they made fun of what was happening.

Surveillance, curfews, and an allowance

Also according to Madison, Hef's live-in girlfriends could not work outside the mansion, though Madison briefly held on to her job at Hooters. It was her only contact with the outside world and only source of income beyond Hef's inadequate clothing and beauty allowance. Soon Hef forced her to quit. "It was just a dumb waitressing job," Madison said (via Buzzfeed), "but after I was pressured to give that job up, I really felt cut off from the outside world."

There were plenty of other rules: no red lipstick, no social media, a 9 p.m. curfew, and no inviting boys in the mansion. According to Madison, Hef once told her, "You look old, hard, and cheap." The girlfriends who appeared on "The Girls Next Door," the E! reality show about life in the mansion, also had to contend with Hefner tracking them. According to cast member Kendra Wilkinson (pictured), Playboy staffers would use a book to keep tabs on when the women left the mansion and returned every day (via New York Daily News). Hefner read the book every morning.

Hef's girlfriends were paid an allowance on Fridays

Also according to Buzzfeed, Hef's girlfriends were not allowed to appear in Playboy Magazine because once they did, they often left him. On Friday mornings, the women received a $1,000 allowance each, paid in $100 bills. Hef reportedly distributed the money in his bedroom while picking up dog feces. On the topic of cleanliness at Playboy mansion, Hefner ex Izabella St. James (pictured) wrote in her memoir "Bunny Tales: Behind Closed Doors at the Playboy Mansion" (via Cosmopolitan) that the mattresses and sheets the women were given were old worn and stained, and the carpet in Hef's bedroom was dirty.

Each Friday, as Hefner paid the women, he would use the time to offer them feedback. "Most of the complaints were about the lack of harmony among the girlfriends — or your lack of sexual participation in the 'parties' he held in his bedroom," St. James wrote in her memoir, as quoted by Cosmopolitan. "If we'd been out of town for any reason and missed one of the official 'going out' nights ... he wouldn't want to give us the allowance. He used it as a weapon."