In July 1989 she married Hugh Hefner, becoming his second wife.
Kimberley was the mother of two of Hef’s four children, Marston Glenn Hefner and Cooper Bradford Hefner.
Though they publicly denied it, all girlfriends were expected to participate in Hef's bizarre bedtime group sex ritual.
According to Madison (and some details have been echoed by other former girlfriends), the ritual would begin with them putting on matching pink flannel pajamas.
Pitfalls aside, Hef's youngest ex maintains that she enjoyed life with her 82-year-old beau.
"Hef was kind of like my best friend, but a sugar daddy at the same time ...
Hef would pleasure himself while watching porn and smoking pot before taking short turns with the girls in the room and then finishing by himself. Ever since I left the mansion about six years ago, I got offers and interest for doing a tell-all book.
All the while, Madison writes, the women around him would "[go] through the motions as if they were getting it on or making out with each other, but no one really was." She adds, "No one was actually in the mood (besides Hef, I assumed) or turned on in the slightest." Madison discussed that and much more from her book on a call with And I wasn't interested at first, so I was like, "No, I don't just want to do a tell-all where I talk about someone else." If I do ever write a book I want it to be my story and my journey and what I learned.