The book revealed that:
Hefner once had a gay sex encounter, which occurred in an unspecified time and an unnamed bar in Chicago... “...He was propositioned [by a man] and, thought, 'What the hell...'"Hef was said to have found it “an interesting experience."
Since Hefner is still alive, so perhaps might be the man who successfully hit on one of the 20th century's most dedicated male heterosexuals and scored.
AKSARBENT thinks that the International Gay Conspiracy needs to find this man and write down everything he says before it is too late and relay any tips to the dude who made the video below, who might have better luck in his endeavors, unless he really is straight, in which case he may not want to increase his success rate. (Via Towleroad and yes, there is a girl-on-girl version.)