Down the Rabbit Hole

Read Down the Rabbit Hole for Free Online

Book: Read Down the Rabbit Hole for Free Online
Authors: Holly Madison
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, either. I knew that the role of girlfriend was coveted by many and fleeting for some, so I expected the women to be defensive, protective, and, quite frankly, bitchy—especially this crop of girls who looked more like garden variety strippers than dazzling Playboy bunnies. I was surprised with how wrong I thought I

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