Hugh Hefner, who founded the Playboy empire in 1952, was often thought of as ​an easygoing magazine mogul surrounded by beautiful women. He called the Playboy Mansion home and it emanated luxury, from the well-known Grotto to the scantily clad women wearing the infamous bunny ears serving Hef drinks on silver platters. However, after Hugh passed away in 2017, many of the former Playboy Bunnies who were close with the publisher revealed several shocking sex confessions.
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HOLLY MADISON

Holly Madison spilled several bombshells in her ​2015 book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.

Holly, who eventually became Hugh’s ​No. 1 girlfriend, said that sex life with the CEO wasn’t what most would expect. She claimed that Hugh would smoke weed and masturbate while he forced several women to dress in identical lingerie in front of him and watch porn. She also gave a few details regarding her intimate moments with Hugh.

“There was zero intimacy involved. No kissing, nothing,” Holly revealed in the book. “It was so brief that I can’t even recall what it felt like beyond having a heavy body on top of mine.”

Holly also exclusively revealed to In Touch in January 2024 that Hugh required the women in the house to abide by certain rules.

“You were always expected to look a certain way, maintain your hair color, behave a certain way,” she explained. “It just kind of overall gave me the feeling of walking on eggshells at all times. I wore red lipstick and found out the hard way that Hef didn’t like it.”
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KENDRA WILKINSON

Kendra Wilkinson was also one of Hef’s well-known girlfriends and penned her own book, Being Kendra: Cribs, Cocktails, and Getting My Sexy Back, which revealed some shocking information. The mom of two admitted that she was only 18 when she had sex with ​then-78-year-old Hugh for the first time.

“I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it,” Kendra wrote. “At about the minute mark, I pulled away and it was done. It was like a job. Clock in, clock out. It’s not like I enjoyed having sex with him.”
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CARLA HOWE

Carla Howe became a Playboy Bunny alongside her twin sister Melissa in 2011. Carla spoke with The Sun in 2015 and claimed that the Playboy Mansion was “more like an old person’s home” versus a hedonistic escape. She also added that Hugh wasn’t the big partier most people believed him to be.

“He almost never leaves home and refuses to change anything in the mansion, so the whole place feels like it’s stuck in the 1980s,” Carla said.
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CRYSTAL HEFNER

Hugh’s third and final wife, Crystal Hefner (née Harris,) shared plenty of details about their sex life ​after he died in her book Only Say Good Things: Surviving Playboy and Finding Myself. Many of her stories echoed Holly’s claims.

“This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time,” Crystal wrote in the memoir. “Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas. The dimming of the lights. The music. The porn. Passing the pot. And then the sex.”
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BRIDGET MARQUARDT

Bridget Marquardt was 28 when she moved into the Playboy Mansion. She eventually became one of Hef’s “main girlfriends” and during an episode of the “Juicy Scoop” podcast in 2022,​ she revealed she was once pressured into having unprotected sex during an orgy at the mansion.

“I was still just gonna watch and then [one of the other Playmates] was like, ‘Aren’t you gonna go?’ It was like, ‘You need to go.’ And I was like, ​’I would rather not.’ And she’s like, ‘Well, then you probably won’t be invited back,’” she recalled.
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IZABELLA ST. JAMES

Izabella St. James detailed some of her moments with Hugh in her book Bunny Tales: Behind Closed Doors at the Playboy Mansion. She detailed how Hugh gave each of the women in the mansion a $1,000 allowance every Friday, but that many of the women dreaded it because he always took it as an opportunity to complain about what was wrong in their relationship.

“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,” Izabella revealed.