The long list of hot women Hugh Hefner has slept with – #2 will shock you! (With Pictures)

8. Karen Christy

Something has to be said about the girl that gave Hefner his most passionate relationship – and those are his own words. Karen Christy met Hefner in Chicago, though hailing from Texas, and from there the two started having an affair of sorts. It’s reported that Hefner’s staff would invite Christy to the Playboy mansion only when his current girlfriend, Barbi Benton, was out of town or on the road.

It might not sound like much of a scandal for Hef to be a philanderer, but the pictures of the duo together were big enough to make it into Time magazine who busted the two lovebirds.