Down the Rabbit Hole - Holly Madison

less prestigious “minor pictorials” in Playboy or for pictorials on Playboy.com.
The guest list for the Sunday pool parties was much more selective, so I have to admit, I was
flattered to have been included. Only 20 or so girls were invited to these more intimate events
splashing the day away. Yet it was rare to see any of Hef’s then seven girlfriends at the pool party for
any length of time. I remember it striking me as odd that they chose to hole away in their mansion
bedrooms, but I didn’t give it much thought beyond that. (I would later realize that they considered it
dues they no longer needed to pay.) As for Hef, he would tuck away in a corner of the pool and play
backgammon with two friends—usually the only other males allowed to be in attendance.
Occasionally they would stride over and join the girls in a drink or a game, but they mostly kept to
themselves and always focused their attention on Hef. After all, they wanted a repeat invite and Hef,
without actually saying a word, made it clear that the girls were solely for his amusement. The
staffers—who strictly refused all tips—were readily available to wait on us hand and foot, the
mansion gym was available to any of the girls who wanted to work out during the party (perhaps a red
flag to the expectations placed on the women of Playboy), and a masseuse was on call in the
bathhouse for guests looking to further unwind.
One afternoon I was freshening up in the bathhouse and talking with a girlfriend when a buxom
woman named Nicole bounded in and introduced herself. She was very sweet, but I could barely stop
gaping long enough to get a word out. This woman had the largest breasts I’d ever seen, so large that
it looked like the implants were struggling to escape from under her skin. The masseuse had to go
rustle up an extra stack of towels just so Nicole could lie on her stomach for the treatment. (Years
later, I was flipping through an issue of Playboy and recognized the busty blonde from the bathhouse
—only this time her name was Coco and she was married to the rapper Ice-T. It’s been her booty that
has earned her the most attention, but strangely enough I didn’t notice her butt as unusually large back
then. Probably because I couldn’t take my eyes off of those boobs!)
When the light would eventually dip below the hills in yet another picture perfect sunset, the
service staff would busy themselves with preparations for the evening’s dinner and movie screening.
The pool party guests would excuse themselves to freshen up as the festivities moved inside.
Eventually, some of the girlfriends would trickle down from upstairs and idly take their obligatory
seat next to Hef at the dining table for the pre-movie buffet. I could never understand their lack of
enthusiasm; they seemed to have it all. Initially, I assumed they were spoiled, jaded, or just not a good
fit in Hef’s world—maybe they hated the social scene or hated watching old movies every week.
Since those were things I happened to love, I couldn’t understand it.
Because I was an L.A. transplant, the concept of “being fake” was still a bit lost on me. Don’t
get me wrong; I was familiar with fake tans, fake nails, and of course fake boobs, having already
undergone my breast enhancement surgery. But I didn’t have any idea how insincere and calculated
people could be. It never dawned on me that the girls I was about to be spending a lot of time with
had ulterior motives beyond simply being friendly, and that all of their encouragement was just for
show. As I’d come to learn, they saw me as a useful pawn in their twisted game of Playboy chess.
In those early days, Vicky and Lisa (two of Hef’s live-in girlfriends) were incredibly welcoming
—the other girlfriends weren’t particularly mean, but they didn’t exactly roll out the red carpet,