n 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.”
