Hugh Hefner’s Male ‘Playboy’ Fantasy Lived on in Diddy

Sean Combs turns 55 on Nov. 5, and he is all but certain to spend his birthday in the notorious Metropolitan Detention Center in Brooklyn, facing federal charges of sex trafficking and racketeering and conspiracy.

“Mr. Combs physically and sexually abused victims for decades,” Asst. U.S. Attorney Emily Johnson said while successfully arguing at his Sept. 19 arraignment for a Manhattan federal magistrate to remand the hip hop mogul. “He used the vast resources of his company to facilitate his abuse and cover up his crimes. Simply put, he is a serial abuser and a serial obstructor.”

Almost six years ago, on Nov. 4, 2018, Combs marked his 49th birthday by donning a knock-off NASA space suit that had the word “LOVE” on the chest and boarding a small private plane with parachute.

“I’m gonna jump out a plane and attempt to land two houses down in the backyard of the Playboy mansion,” he said in an online video he made of the stunt at the time. “I’m living my best life!”

After pausing to tell everybody to be sure to vote in the next day’s midterm election, Combs proceeded to parachute onto the grounds of the 29-room, 21,987-square foot Gothic Revival residence in Holcomb Hills where Playboy publisher Hugh Hefner had died the year before. Hefner had long portrayed himself as living what he sold as every male’s fantasy. Women were just objects, and they were not even that unless they were young and had a certain look and bra size.

Combs ascribed to a hip-hop version of the Playboy lifestyle; years before the rapper’s stunt, Hefner had let him host a party at his mansion after the 2012 Grammy Awards.

“This is actually one of the HOTTEST parties I’ve ever thrown!! Right now at the Playboy Mansion!!!! Let’s goooooooo!!!!” he reportedly tweeted.

Maybe it was a little too hot. TMZ would report that he was suddenly hit with “an extreme migraine.” His entourage took him to the emergency room at the UCLA Medical Center, where he was examined and released.

But that did not dim Combs’ admiration for the Hefner philosophy.

In 2014, Combs paid $40 million for a newly constructed “European-style villa” a brief stroll from Hefner’s mansion. Like Hefner, Combs now had a private movie theater and a pool with a grotto.

Hefner died in 2017. In an added insult to women, he was interred one row and four spaces from the woefully objectified Marilyn Monroe at Pierce Brothers Westwood Village Memorial Park and Mortuary in Los Angeles. He had purchased this crypt for $75,000 a quarter-century before.

The hip-hop version of Hefner’s male fantasy lived on in Combs, but his self-image was too macho to just lounge around in pajamas. He made that clear the following year.

Combs’ home sat on just 1.3 acres, but the grounds of the nearby Playboy mansion were 5.3 acres, big enough for Combs to make his big birthday skydive. He descended out of a blue sky onto the grassy lawn while in the lap of an experienced parachutist.

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“I DID IT!!!” Coombs proclaimed in a tweet that has since been deleted. “Thank you to my neighbors at the Playboy Mansion for letting me use their house to land. NO FEAR!!!!”

Combs might have come up with something even more dramatic for his birthday this year, along with a fresh reminder to vote the next day—this in one of the most momentous elections in American history.

But, where he sported a NASA suit on his 49th, Combs is almost sure to be wearing a prison uniform for his 55th. And, where people clamored for invites to his birthday fetes in years past, any innocent souls who did attend should be asking themselves how they could have ignored all the signs of the evil reality at the core of his chill image.

We should have asked the same about Hefner. The truth of that was evident in his catch-and-abuse of Kristina and Karissa Shannon, identical twins from Clearwater Beach, Florida. They were 18 when they were lured by an illusion of glitz and glamor to move into the Playboy Mansion.

As they told A&E’s 2022 docuseries, Secrets of Playboy, the twins were invited into Hefner’s bedroom on their 19th birthday. They say he gave them each a pill, apparently quaaludes, which he nicknamed “thigh openers.” Karissa says on the docuseries that she and her twin were suddenly “really f---ed up… the most inebriated we’ve ever been.” She recalled that Hefner started “pulling our heads down, like a very hard pull, down to his penis so that we would give him oral sex.”

The twins say they had never engaged in a threesome with each other before. And Hefner was 84.

“Just imagine this,” Karissa said. “His old hand kind of shakes [as he’s] touching your boob. It’s like you’re having sex with your grandpa.”

By their account, the twins waited until Hefner dozed off. They then ran into a spare bedroom and took a streaming hot shower to “sterilize” themselves

“After that night, I didn’t feel like my body was mine anymore,” Kristina said. “I felt used, disgusted.”

But as can happen to those who have been lured and groomed, the twins found themselves unable to just leave. They began to drink heavily, starting at the 5 p.m. dinner to anesthetize before midnight, when Hefner would summon any women in his mansion to his bedroom for his version of what Combs would later call “freak offs.”

During the 18-month ordeal between 2008 and 2010, Karissa became pregnant.

“Every time I’ve done it with him, it’s assault," she said on the docuseries. “To me, it’s like rape. He used control mechanisms completely through everything, so I’m happy that I had the abortion.”

When contacted by the Daily Beast last week, Kristina inquired if she would be paid for an interview. She was told no and did not respond to subsequent texts. Her sister did not reply to a query.

And as told by the docuseries, the twins were just two of many. Hefner’s ex-girlfriend, Sondra Theodore, said, Hefner would break down innocent young women and watch them do things they never thought they would do.

“Really, he was a monster, the things that he got turned on by,” Theodore said. “Nothing was enough, nothing."

And, like Combs is alleged to have done, Hefner would sometimes just sit and look, sometimes filming it so he could watch it again or maybe show it to others.

When A&E released The Secrets of Playboy, it noted that “the vast majority of allegations have not been the subject of criminal investigations or charges, and they do not constitute proof of guilt.”

If Hefner were alive today, things may be different. But because Hefner was never investigated, he was never in danger of having to trade his pajamas for the prison uniform Combs now wears.