Down the Rabbit Hole

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Authors: Holly Madison
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prompted—and I had met a very welcoming response—so I figured I might have the same luck with moving in. I was a young blond girl with a small waist and large boobs, but I wasn’t quite as polished as the girls that usually decorated Playboy ’s pages—and hallways. Still, for the most part, I fit the bill of “girlfriend.”
    I can do this, I thought.
    It might be hard to understand, but in that moment, I didn’t blame Hef for anything creepy that had gone on the night before. He had the “nice guy” act down pat and it worked. At the time, Hef still had a certain swagger. There was a gentlemanly air about him that belied his reputation. And there was never a shortage of Hef’s friends lingering around the mansion who were all too eager to remind every pretty young thing that stepped through the doorway what an amazing, kind man Hugh Hefner is. It was easy to fall under the spell. If anything, it was the other girls I felt used by, and I couldn’t let them win.
    â€œCan I ask you something?” I let out another squeak. He looked up at me for the first time and I flat-out told him that I had no place to live. “What do you think about me moving in?”
    He took a brief moment to consider what I had just asked before finally saying, “You can stay for a while and we’ll see how it works out.”

C HAPTER 3

    â€œIt’s really dreadful,” she muttered to herself, “the way all the creatures argue. It’s enough to drive one crazy!”
    â€” Lewis Carroll, Alice’s Adventures in Wonderland
    I t only took me one trip in my beat-up red Toyota Celica to move my entire life from a tiny Westwood apartment into a Holmby Hills estate. No one offered to move me in, but I didn’t really need the help. I didn’t have much to bring besides the few outfits I owned, some makeup, my college books, and a handful of childish knickknacks, like Disney Princess picture frames and Star Wars figurines. I don’t even think I owned a curling iron at the time. I left my single twin mattress next to a Dumpster.
    As I pulled up the iconic driveway on Charing Cross Road, it couldn’t have felt less like “home.” The gates opened for me, and just like that, I was the newest resident of the Playboy Mansion. I pulled my car through the driveway and gave the keys to one of the staffers, who then made a call to one of Hef’s secretaries. She directed me to my room and presented me with my room key.
    Less than an hour later I had moved my belongings into the bedroom that Hef’s secretary designated for me, and that was that. None of the girls even poked their heads out of their bedrooms, let alone offered to help. I was pointed to my room and left alone. Now what? I thought. It was entirely bizarre.
    I didn’t tell many people about my decision to move into the mansion—I quickly learned that not everyone had the most positive reaction. I had naïvely thought of myself as an adult who was free to make her own decisions, out of high school, away from small-town Oregon, and far from the type of people who would judge me for my personal decisions. I was so wrong.
    When I told Nora I was moving into the Playboy Mansion, her jaw dropped so quickly I thought it would hit the ground. Nora was hyper-materialistic and wasn’t expecting me to go from “rags to riches” faster than her. In my excitement, I also told the first acquaintance I had run into while doing errands. His reaction wasn’t what I had expected, either.
    â€œYou hooked up with an old dude?” he cried, his face scrunching up. “Gross!”
    All I had said was that I was moving in—nothing about being intimate with anyone. I guess not everyone was as naïve as I had been. Seeing the angry look that appeared on my face, he quickly switched gears.
    â€œSo,” he said, his voice much friendlier, “can you get me on the list for the

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