Hugh Hefner lived in his own fantasy world surrounded by stunning women – with his life revolving around sex.
The American tycoon, who passed away in 2017, always had at least three beautiful girlfriends living with him inside the infamous Playboy Mansion.
“Much of my life has been like an adolescent dream,” Hef once confessed, with his debauched lifestyle provoking a mix of envy and disgust in equal measure from many.
“If you were still a boy, in almost a Peter Pan kind of way, and could have just the perfect life that you wanted to have, that’s the life I invented for myself.”
Hef’s indulgence in women continued into his later years, even when he was barely able to still bonk.
His final wife, Crystal Harris, revealed that sex with Hugh only lasted “two seconds” after she called off their initial wedding just a few days before they were due to walk up the aisle in 2011.
Hugh Hefner was married to Crystal Harris when he was 82 and she was only 22 (Image: WENN)
Crystal moved into the mansion when she was only 22 and Hefner was 82 – a staggering 60-year age gap.
But Hugh may never have lived that long had it not been for the quick thinking of a former Playmate when a sexual experience went wrong.
The Playboy boss started choking on a sex toy during a romp and nearly died in 1977.
“What is the closest I’ve come to death? That time I was having sex with four Playmates and I almost swallowed a Ben Wa ball,’ said Hef in his book.
He began choking and was bout to pass out but was saved when girlfriend Sondra Theodore pumped his chest and dislodged the toy.
The Playboy founder with former girlfriends Holly Madison and Kendra Wilkinson (Image: Kevin Winter/Getty Images)
Hugh went through plenty of girlfriends throughout his life – with many revealing his sordid secrets after leaving the intensity of the mansion.
Kendra Wilkinson, who dated and lived with Hef from 2004 to 2008, claimed she had to be drunk to survive sleeping with her boyfriend.
“I moved in and weeks went by and I didn’t know that sex was involved,” admitted Kendra.
“I was usually very drunk doing those evenings. I tended not to care about much until the next day. I had to be very drunk or smoke lots of weed to survive those nights.
“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.”
Izabella St James (left) revealed Hef funded unlimited plastic surgery
While Polish model Izabella St James, who moved in for two years in 2002, explained the girls were given a staggering $1,000 weekly allowance.
Hugh would also fund unlimited plastic surgery for his girlfriends, but it came at a cost.
Once a week they would have to go to his room to ask for their money while Hef picked up dog poo from the carpet.
“Every Friday morning we had to go to Hef’s room, wait while he picked up all the dog poo off the carpet – then ask for our allowance,” explained Izabella.
“We all hated this process. Hef would always use the occasion to bring up anything he wasn’t happy about in the relationship.
“Most complaints were about the lack of harmony among the girlfriends or your lack of sexual participation in the ‘parties’ he held in his bedroom.”
Playboy founder Hugh Hefner and Playboy bunny Holly Madison in 2003 (Image: Getty)
There are even darker stories, with one former “number one” girlfriend admitting she was “freaked out and ashamed” after taking part in group sex sessions.
Holly Madison who was just 21 when she got with Hef in 2001, claimed she was so traumatised by her time at the celeb-packed pad that she developed a stammer.
She slammed Hef as a a “cruelly manipulative” man who stripped her of her self-worth and offered her “thigh-opening” drugs.
“The sexy fairytale Hef would have you believe in was a bedazzled, twisted, toxic prison. And I know that because I spent six years as Girlfriend Number One to a man old enough to be my grandfather,” she wrote in her 2015 biography, Down the Rabbit Hole.
The life inside the Playboy Mansion was certainly not what she imagined – with the girls having a strict 9pm curfew.
Hugh Hefner and girlfriend Holly Madison flash outside The Standard Hotel on September 24, 2003
The grand staircase was covered in pee stains from his nine dogs.
There was a strict routine, with the girls required to attend club nights on Wednesday and Friday, followed by a buffet dinner and movie night on Saturday and a pool party on Sunday.
“His harem of girlfriends would trickle down to take their seats next to Hef at the dining table,” explained Holly.
“I could never understand their lack of enthusiasm. Initially, I assumed they were spoiled, jaded, or just not a good fit in Hef’s world. This may sound naïve, but I didn’t immediately realise that they were actually required to sleep with him.”
The worst part, according to the reality star, was the way Hef tried to turn the girls against each other to create the impression that he was being “fought over”.
He also berated them, ordering Holly not to wear red lipstick again because it made her look, “old, hard and cheap.”
Pamela Anderson spent some time with Hef in the mansion (Image: E!)
Pamela Anderson also opened on the wild sex escapades in the mansion, including being invited to have sex with the Playboy founder while seven women watched.
“Everyone was naked in the grotto and the girls were downstairs and they all went upstairs,” she told Piers Morgan on his Life Stories programme.
“I followed them upstairs. I thought, ‘What could be going on up here?’ Seven girls, one at a time with Hef.
“I was stood at the end of the bed watching them and then I realised they were watching me. I thought, ‘This is not a movie. I need to leave’.”
Another famous face who stayed in the Playboy Mansion is Katie Price, who stayed for six weeks in 2002.
Katie had a brief stay in the Playboy Mansion (Image: Mario Anzuoni/ Splash News)
Katie actually turned down the chance to sleep with the Playboy founder and become one of his girlfriends – which would have taken her life down a completely different path in life.
But she was still determined to make her mark in a very unpleasant way to let people know she had been there.
In an unearthed interview, the mum-of-five confessed to urinating in the infamous grotto, which featured a large swimming pool in a cave.
“When I was younger I lived with Hugh Hefner at the Playboy Mansion for about six weeks, but to be a girlfriend you have to do the deed and I did not want to do the deed,” Katie explained during her Cardiff tour in 2017.
“He’s a really nice guy though. I just didn’t want to do it. But I went to the famous grotto and I marked my territory – I p***ed in it.”
The reality star also confessed she had a fling with a woman while living in the LA mansion.
Katie has spoken openly about her time in the mansion (Image: GETTY)
“I have had time with a woman, not a relationship, but only when I am drunk, never sober,” she told fans at her An Evening With Katie Price show in Gateshead.
“You know, when you’re with your mates like in a room, mucking about, like the Playboy Mansion. I have had like threesomes and all of that. It was years ago.”
Katie also discussed watching him have intercourse with other girls and opened up about his bizarre sex toys.
“I was really intimidated at first. He told me he wanted me to be his girlfriend but to be his girlfriend you have to do the deed. You either encourage it or you don’t and I didn’t,” she said.
“I saw him do the deed with younger girls. On a Monday, Wednesday and Friday we would all go out and then back to his room. Some of the toys were like a Dyson Hoover.”
Hugh Hefner’s lavish Playboy Mansion in Los Angeles (Image: Getty Images)
Hugh went to desperate lengths to make sure no one found his ‘treasure chest’ of sex tapes and X-Rated photos dating back to the 1950s.
He became paranoid that someone would find his hidden private collection after Pamela Anderson’s sex tape was leaked.
According to an insider, he collected up his entire hidden collection and put them in a concrete-lined box so they couldn’t fall into the wrong hands.
He then asked the Playboy Mansion’s head of security Joe Piastro to oversee the collection being thrown into the Pacific Ocean.
It also reportedly contained personal notes and photographs given to him by celebrities, including Marilyn Monroe.
“Hugh was terrified of the world finding out everything about his past,” a source told the Sun.
“He had hundreds of other photographs of women who were not famous, but he had enjoyed one nights stands with or even short relationships. There were also audio tapes too.”
Twin sisters Malissa and Carla with Playboy tycoon Hugh Hefner
They claim he was so paranoid in the 90s that he decided it was best to get rid of them all, but didn’t trust people to burn them in case they were stolen.
The source added: “Hugh explained that he didn’t want anyone’s lives, marriages or careers to be destroyed by what he had in his library.”
During his later years, Hugh reportedly spent most of his time in his most treasured possession – his rotating bed.
He would watch movies with the girls and even have dinner parties in his bed while wearing his famous pyjamas.
The media mogul also revealed he preferred to spend most of his time in bed, doing as many activities as possible there.
British twins twins Melissa and Carla Howe were “relieved” not to have to sleep with him but enjoyed the parties.
Carla said: “We would watch movies with him. He would use a Zimmer frame, and he mainly walked with the help of nurses. He was never without a nurse. They gave him round-the-clock care.”
Source: Celebrities - dailystar.co.uk
