Cavalier Hugh Hefner says 'Why Not?' to Incestuous Foursomes, Gay Sex

While most old folks would reward a query like, "Tell me about your fourgies, Grandpa!" with a sharp caning, Playboy founder Hugh Hefner is of a different breed. In his upcoming book, Mr. Playboy: Hugh Hefner and the American Dream, Steven Watts convinced the swinging octogenarian to open up about his earliest sexual adventures, including one aborted wife swap that led the mogul to seek out friendlier, more familiar partners. Says Page Six:

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].'"

Hef, you rascal! While the Chicago tourism board and The Advocate would no doubt welcome your twin endorsements of the Windy City and gay bee-jays, you surely queered the deal with intra-family extracurriculars that are more Penthouse than Playboy. Still, your pre-Eisenhower romp deserves kudos for one thing: it's the only recorded foursome in history with participants named "Millie" and "Rae."