Hugh Hefner's widow on first time having 'odd and robotic' sex with Playboy boss

25 January 2024 , 12:35

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Crystal Hefner has detailed her first orgy with Hugh Hefner (Image: GC Images)

Crystal Hefner has detailed her first sexual encounter with Hugh Hefner in her new tell-all memoir Only Say Good Things: Surviving Playboy and Finding Myself.

The book starts with an in depth description of how she first arrived in the Playboy Mansion as a college student after being invited to a Halloween Party there. She then elaborates on how she found herself in Hugh's bedroom surrounded by other women as she began her first sexual experience with him.

Crystal, 37, says she she knew "it was probably going to be wild" but she "wasn't thinking about the sex" as she followed Hugh to the room. She also claimed that while she had been drinking she didn't feel drunk but instead was "intoxicated by this new, mysterious version of my life."

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Crystal makes a series of shocking revelations in the book (GC Images)

Crystal became Hugh's chief girlfriend then his wife (AFP/Getty Images)

She described how when she arrived in the bedroom she immediately noticed there was a chandelier covered in underwear "like some kind of carousel of trophies," and that four TVs around the bed were playing vintage porn. Crystal then details how she was given silk pyjamas to change into and how Hugh gout out a locked box which he removed a joint from.

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She said he then "grabbed a bottle of baby oil off the nightstand and oiled himself up. Then he looked up at the four of us and waited." She wrote: "He gave an impatient, questioning smile and opened his hands in a gesture that suggested, 'Who's first? Let's get a move on."

Crystal described how safe sex was not an option as "there were no condoms in sight" and how the encounter was purely physical with "no kissing or romance or intimacy" involved with the experience feeling "odd and robotic." She said it felt "like Hef was just going through the motions of something that had once been fun and sexy," and Crystal confessed that she was the second woman to have intercourse with him on the night.

Crystal nursed Hugh up until his death in 2017 (WireImage)

She explained: "My body wasn't ready, but it didn't matter because of all the baby oil. I was very much outside my body watching the show, above the bed was a huge mirror, and while I was on top of Hugh Hefner having sex with him for the first time, he didn't look into my eyes once, he stared to the side and up, watching the view from above in the mirror."

Crystal then admitted that "there was nothing sexy about it," and that she realised it "wasn't about making love. It was about power and control and leverage. It was a performance," and that she felt she was "auditioning for a part."

She also detailed how she and another woman then "pretended" to use sex toys on each other until Hugh "suddenly" dismissed them and "grabbed himself to finish the job." She described his climax as him "moaning and flailing and flopping like a fish trying to get back to water" adding "his face contorted as if he was in pain" and calling it, "the strangest five seconds of my life." Crystal says Hugh then turned off the porn and went to bed.

Ayeesha Walsh