Hugh Hefner’s widow Crystal shared tragic reason why she played the exact same song every time they were intimate

Hugh Hefner’s widow has revealed one routine the pair always had to engage in during intimacy – and the reason why.

Crystal opened up about her sex life with Hugh Hefner. Credit: Charley Gallay/Getty Images for Playboy

The Playboy mogul was married to his third wife, Crystal Hefner, at the time of his death from sepsis at the age of 91 in 2017.

Crystal, now 38, has shared some insights into the couple’s private life, including the reason they always played a certain song while getting intimate.

She opened up on a number of bombshell revelations in her 2024 tell-all memoir, Only Say Good Things: Surviving Playboy and Finding Myself.

She told People that she preferred group sex rather than one-on-one intimacy with her husband, who needed to take sexual enhancement drugs in order to perform.

Crystal revealed that the pair would have “little blue pill nights” and Hugh also needed to have music on while getting intimate.

She explained that she always put on the same song by Madonna – though she did not specify which one – and the heartbreaking reason why.

Crystal revealed she stuck to the same track as “then no other music will be contaminated by this place”.

 

Crystal was 21 when she met the Playboy founder. Credit: Tommaso Boddi/WireImage/Getty Images

The model had met Hugh – who was 60 years her senior – when she was just 21 years old, and the pair began dating in 2009 before tying the knot in 2012.

However, just two years into their marriage, Crystal reveals the sex ended – which she found to be a “relief”.

She explained: “There was no more bringing girls home, no more performances. For years, I had been keeping up the Playboy charade for Hef, for the public.”

Crystal had also revealed how “odd and robotic” sex was with Hugh, as there was no kissing or romance involved.

She explained: “Hef was just going through the motions of something that had once been fun and sexy. Or maybe it was never fun and sexy.”

Crystal revealed that the first time she was invited up to the magazine mogul’s bedroom to join in with the group sex, he did not even look at her when it was her turn, instead he stared at a mirror placed on the ceiling.

She added in her book: “There was nothing sexy about it. It was about power and control and leverage. It was a performance. I was auditioning for a part.”

Crystal also alleged that Hugh “seemed less sex-savvy than some of the teenage boys I’d been with years ago.

“It was clear to me Hef had never taken a moment in his entire life to figure out how to please someone else.”

She is not the only ex-girlfriend to open up about life at the Playboy Mansion, as former girlfriend Kendra Wilkinson also recently shared the issues she’s been left with as a result of the relationship.

The former Playboy model, now 39, was the youngest of the magazine mogul’s three girlfriends featured on their reality show, The Girls Next Door.

At the time, Hefner was also dating Bridget Marquardt, now 51, and main girlfriend Holly Madison, now 45.

Wilkinson had met Hefner at his 78th birthday party when she was just 18 years old, and moved into the Playboy Mansion shortly after they met, living there for five years.

Speaking on the Amy & T.J. podcast, Wilkinson admitted: “Look, I struggle still to this day with my relationships and my views on sex.

“I had to go through a lot of therapy, and they looked at me and they’re like — this is the first time I’m admitting this — but they’re like, ‘You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking of sex.'”

Host T.J. Holmes asked the model-turned-real-estate agent how her relationship with Hefner – and their 60-year age-gap – as well as the “environment” she spent those formative years in affected her long-term.

He asked: “Again, you’re a teenager. You hadn’t been necessarily exposed to healthy relationships at that point in your life, but it puts you on a certain path — what did that do to you and [how did it] shape what you thought a relationship was, should be, and the type of person you were interested in?”

 

Kendra Wilkinson admitted her 60-year age-gap relationship with Hugh Hefner still causes her ‘problems’ with intimacy. Credit: Denise Truscello/WireImage/Getty Images

Wilkinson admitted it caused her to have “just unhealthy thoughts”, explaining: “Not really settling for a marriage and stuff like that.

“Which is not, I wouldn’t say unhealthy — I’m saying that everyone has their choices, and some people wanna be single, some people wanna be married … and I’m more of a fun idea type of person.”

Wilkinson ended up leaving the mansion for good in 2009 after getting engaged to former Philadelphia Eagles star Hank Baskett, with the pair even holding their wedding ceremony at the Playboy Mansion.