Weird Rules That Hugh Hefner's Girlfriends Had To Follow

There might have been tons of wild parties at the Playboy Mansion, but being a Playboy Bunny doesn't sound very fun, particularly if you were one of Playboy mogul Hugh Hefner's live-in group of seven unhappy employees — or, as he called them, girlfriends. One of Hefner's exes, Holly Madison, wrote in her 2015 memoir "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny" that the experience of being a live-in Bunny made her deeply depressed. "Drowning myself seemed like a logical way to escape the ridiculous life I was leading," she writes in the book, as quoted by Buzzfeed. "I just couldn't take my misery anymore."

Part of the misery seems to have been Hefner's penchant for bizarre, highly specific rules about how the Playboy Bunnies should act, what they should, and how they should look. Hefner even had schedules for the "girls" — from a curfew to specific nights for group sex (via Cosmopolitan).

The worst rule: scheduled 'chore vibe' sex

Hefner would have sex with his girlfriends on Wednesdays and Fridays, after they went out to a nightclub, according to Buzzfeed's interview with Holly Madison. "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 out of their minds on quaaludes (Hefner called them "thigh-openers," Madison claims) while one woman had to copulate with the elderly man at the center of it all.

Other ex-girlfriends have claimed they would each get a turn in the sack with Hef, a couple of minutes each, with the "main girlfriend" going first (via Cosmopolitan). "It had kind of a chore vibe, I felt," Madison told Buzzfeed."The girls would stand there and they'd kind of like put on a show to create a silhouette that something was going on. Hef couldn't hear very well out of one ear, and I could hear them all talking and making fun of what was going on and gossiping."

Surveillance, curfews, and an allowance

There were plenty of other rules: no red lipstick, no social media, a 9 p.m. curfew, and no inviting boys in the mansion. The girlfriends who got 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, 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 would read the book every morning.

On Friday mornings, the women received a $1,000 allowance each, paid in $100 bills. As Hefner paid the women, he would use the time to offer 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," wrote Hefner ex Izabella St. James in her memoir "Bunny Tales: Behind Closed Doors at the Playboy Mansion," 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."