Hugh Hefner’s Ex-Girlfriends Finally Reveal What Really Happened Behind Closed Doors

Nearly a decade after Playboy magazine founder Hugh Hefner passed away, the women who lived with him continue to share stories about the toxic environment at the mansion.

The businessman was married three times. He first married Northwestern University student Mildred “Millie” Williams, with whom he had two children.

His next wife was Playmate Kimberley Conrad. The couple, who had a 36-year age difference, also had two kids.

Hugh Hefner’s girlfriends revealed what the adult magazine founder was really like behind closed doors

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Hefner’s third and final wife, Playmate Crystal Harris, met him in 2008 when she was 21 and he was 60 years her senior.

Throughout his life, he maintained multiple informal relationships with many women at the same time, including a “quad” relationship with Holly Madison, Bridget Marquardt, and Kendra Wilkinson.

Many of the women he was involved with spoke unfavorably of their intimate moments with Hefner.

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Speaking on the In Your Dreams podcast, Holly said she “hated” going to bed with Hefner and the other bunnies.

“If it was just me and him, it was a lot more normal than you would think,” she said. “It’s a very different story between when we were just by ourselves than with everybody else in the room.”

She added, “That was disgusting. I hated it. I made it very known I hated it.”

Hefner allegedly “wouldn’t move” during intimate encounters with several women

Image credits: Luke Ford/Wikimedia

Holly, who was Hefner’s “number one girlfriend” for years, also claimed in the documentarySecrets of Playboy that he kept videos and photos of women to blackmail them.

During intimate encounters with multiple women, the Playboy founder “wouldn’t move,” Holly recalled. 

“He would be like a bump on the log in the middle of the bed. I can’t explain how embarrassing that whole routine was.”

Image credits: In Your Dreams With Owen Thiele

In a conversation with Bridget, Holly revealed that his bedroom was the opposite of glamorous and was “just hoarder-style.”

Bridget agreed, adding, “We walked in and it was just a disaster in there. The lights were out, but there were two giant TV screens in there that were playing p*rn. There’s just so much junk.”

Kendra, who met Hefner at his 78th birthday when she was 19, said there was dog excrement “everywhere” at the infamous mansion and Hefner “would just wobble by and just pick it up with his bare hands.”

Some of his exes came forward with more serious accusations, including claims that Hefner kept track of who slept with him

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According to Bridget, Hefner kept a journal in which he detailed who had slept with him.

“The black book kept track of a few different things,” she explained. “It kept track of when somebody collected their allowance. He would mark it off so you couldn’t ask for it twice. It also kept track of who slept with him and when.”

If a woman gave an excuse to avoid sleeping with him, he would allegedly tell them, “Oh, you’ve been on your period for three weeks.”

 

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Sondra Theodore, one of Hefner’s girlfriends who dated him between 1976 and 1981, revealed that she was “scared” of the adult magazine publisher “because you couldn’t satisfy him; he had to have more and more and more.”

Twins and Playmates Karissa and Kristina Shannon claimed women would catch chlamydia because Hefner refused to use protection. Additionally, Karissa said she had an abortion at 19 because of his refusal to wear a c*ndom.

The businessman, known for his wild parties and non-monogamous relationships, was described as “robotic”

Image credits: CBS LA

Crystal, who remained married to Hefner until his passing, wrote in her memoir, Only Say Good Things: Surviving Playboy and Finding Myself, that her late husband was “less s*x-savvy than some of the teenage boys I’d been with years ago.”

Moreover, she described her intimate encounters with him as “blue little pill nights.” 

Crystal, who told The Guardian that she “came from a world where [she] didn’t have much of anything,” shared that she played the same Madonna song every time she slept with Hefner so that “no other music [would] be contaminated” by the unpleasant experience.

In her book, she further explained the “odd and robotic” sequence that took place when Hefner wanted to share the bed with multiple women.

“[It] went the same exact way every time. 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 p*rn. Passing the pot. And then the s*x.”

Holly also described being told to wear pajamas to get ready for the intimate encounters with Hefner and other bunnies.

Image credits: Denise Truscello/Getty Images

“It’s almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner’s bedroom with his harem of blond bombshells. The answer? Not a whole lot.”

The Chicago-born businessman passed away at the Playboymansion in 2017 at the age of 91 from cardiac arrest and respiratory failure.

He is buried at Westwood Memorial Park in Los Angeles in the crypt beside Marilyn Monroe, a spot he paid $75,000 for in 1992. In 2009, he told the Los Angeles Times, “Spending eternity next to Marilyn is an opportunity too sweet to pass up.”

Crystal recently suggested that Hefner’s foundation may have stored illegal images of underage girls

Image credits: FOX 11 Los Angeles

Last month, Crystal called for an investigation into her late husband’s foundation, which she alleges possesses personal scrapbooks containing explicit photographs of women and, “possibly,” underage girls.

She said she believes the Hugh M. Hefner Foundation holds about 3,000 of Hefner’s images of intimate encounters, which may include pictures of girls who were underage at the time and “could not consent to how their images would be retained or controlled.”

Crystal added that some of the girls may not even have consented to the photos being taken in the first place because they were intoxicated.

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