PLAYBOY founder Hugh Hefner - who boasted of bedding hundreds of women - also had sex with men as he "tested the boundaries" of his sexual appetite, he once claimed.

Ultimate ladies man Hugh Hefner, who died aged 91 yesterday from natural causes, said in a 1999 interview he had slept with men.

10 Carrie Leigh and Hugh Hefner in happier times during their five-year relationship before it ended bitterly. Following their break-up, she said he would often have affairs with other men Credit: Photoshot.

10 Despite commenting on Hefner's homosexual encounters, it emerged Carrie Leigh admitted to having lesbian sex during their relationship Credit: Getty - Contributor

10 The former Playboy cover girl told of Hefner's encounters after their break-up Credit: Photoshot.

10 Carrie Leigh, now in her 50s, launched a multi-million palimony suit after their break up, which she later dropped

10 Carrie Leigh was a successful Playboy cover girl but hit out at the brand after leaving Credit: Getty - Contributor

Hefner admitted experimenting with the opposite sex during his swinging days, according to the Washington Post.

"There was some bisexuality in the heterosexual, swinging part of my life," said Hefner. "I was testing the boundaries, just knocking down walls.

"That period of sexual experimentation is long gone."

Ex-girlfriend Cararie Lewis corroborated his comments after the pair had a bitter break up after dating for five years in the 1980s.

During this time, Leigh filed three lawsuits against him - including a multi-million palimony case which she later dropped.

They began dating when she was aged 19 and he was 57, with Carrie Leigh moving into his world famous mansion in Los Angeles, near Beverly Hills.

10 She became one of Hefner's girlfriends when she was aged 19 and he was 57 Credit: Rex Features

10 The Playboy founder said that Carrie Leigh was 'obsessed' with his homosexual encounters and denied he preferred men Credit: This content is subject to copyright.

Hefner's partners from this period were reportedly disturbed by his sexual encounters with males, according to the 1999 Washington Post article.

Leigh said she even walked in on him having sex with guys and feared his true interest in women was to exploit them.

The Playboy cover girl told the Washington Post it "totally flipped me out" but that Hefner "thought it was okay".

The self-styled godfather of the sexual revolution was famous for being surrounded by beautiful women at his legendary mansion

10 After leaving the Playboy mansion, Carrie Leigh said that she stopped having sex for several years because she felt degraded Credit: Paris Match - Getty

Hefner said claims he preferred men were were a projection of Leigh, who was "obsessed" with his gay affairs and also herself admitted to having lesbian affairs during their relationship.

Carrie Leigh described the Playboy lifestyle as like a "cult" and how she didn't have sex for two years after leaving because she was "sick of feeling like an object".

She compared her time to a line from the Eagles' song Hotel California.

It read: "Mirrors on the ceiling, pink champagne on ice. We're all just prisoners here.

"You know? 'You can check out any time you like, but you can never leave."

At the time of her legal action, Carrie said: “He promised to marry me, he promised to have a child with me, promised to support me.”

Hugh batted off the palimony charge, claiming: “I’m the silliest possible target for a palimony suit, because I’m the most confirmed bachelor of the 20th century.”

10 Hefner, who died aged 91 from natural causes yesterday, claimed to have slept with thousands of women Credit: This content is subject to copyright.

10 Dozens of celebrities have paid tribute to the self-styled godfather of the sexual revolution Credit: PA:Press Association

In later life, Carrie Leigh remarried and launched a rival to Playboy called Nude magazine.

Celebrities from Kim Kardashian to Paris Hilton have paid tribute to the flamboyant figure after his death.

The firm behind the magazine described Hefner as "the American icon who in 1953 introduced the world to Playboy magazine and built the company into one of the most recognisable American global brands in history."

Hefner is survived by his third wife Crystal Harris, a former Playboy Playmate who was Miss December 2009.

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