According to an authorized biography about Hugh Hefner’s life, the Playboy Mogul had some creepy sexual relations with his wife and brother.  Apparently Hugh got to boink his sister-in-law during a an unsuccessful attempt at a foursome between the two couples.

At first it started out him having sex with his wife while his friend poked his own wife on the same bed.  But then it got creepy when he involved his brother.

Hef then went further, trying a foursome out on his own family. “It did happen with his brother, Keith, and his wife, Rae, one evening,” Watts writes. “[But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law.”

The book also says some dude went down on him once.

I’m all for people having foursomes if that’s what it takes to get off, but there is absolutely no reason to involve family.  I can’t even have sex in my mother’s house.  That to me is the naughtiest of naughtiest and I simply will not go there.

HUGH Hefner has gleefully enjoyed a sexually liberated life, but few know it all started with a little erotic dabbling within the Playboy czar’s own family.

In his upcoming book, “Mr. Playboy: Hugh Hefner and the American Dream,” Steven Watts writes how after Hefner wed his first wife, Millie, in 1949, he enlisted his friend Eldon Sellers, who would later help him co-found Playboy, into a staging a foursome.

The book relates: “One night after [Hugh] and Millie watched a stag film with Janie and Eldon Sellers, he suggested that the four of them make love on the same bed, each husband to his own wife. They did and in Sellers’ words, ‘It was different and exciting.’ According to Millie, Hugh began to hint at switching partners, apparently suggesting it with the Sellerses, although the swap never materialized.”

Hef then went further, trying a foursome out on his own family. “It did happen with his brother, Keith, and his wife, Rae, one evening,” Watts writes. “[But] while Millie ultimately backed out of having sex with Keith, Hugh slept with his sister-in-law.”

The book also claims Hef once tried a gay tryst. “Hefner’s thirst for sexual experience became so strong that he even had a one-time homosexual experience,” Watts writes. “One evening in downtown Chicago he was propositioned and, according to Sellers, he ‘thought, what the hell. Found it an interesting experience. As far as I know, the guy just gave him [oral sex].’ ”

Hefner also once shot a porno starring himself called “After the Masquerade.” Watts writes: “It was shot at a friend’s apartment where Hefner and a female acquaintance had sex while wearing masks.”

Hefner told Page Six he cooperated with Watts and gave him access to his personal papers. “This is the most authoritative book ever written about me . . . It’s all essentially true,” he said.

In the spirit of Playboy I thought I’d post the July photos of Cindy Margolis in the publication.  Unfortunately I couldn’t find them.  So here’s her last Playboy spread. Enjoy!

NSFW Playboy photos after the cut…