Down the Rabbit Hole - Holly Madison

“Hef, can I bother you for a second?” I squeaked, my voice breaking midsentence (I would
quickly adopt this as my “go-to” pitch when speaking with Hef—the higher octave made it easier for
him to hear out of his one good ear). Without even looking up from the pages, he gestured with one
hand that I enter his lair. In light of the evening prior, I was even more nervous in his presence than
usual. Hef was so used to girls coming in to ask for favors, though, that he didn’t seem at all surprised
by my impromptu interruption. I had gone from hoping to move into the mansion to downright
determined. There was no way I was not going to get what I wanted after having to sleep with him the
night before (or, rather, earlier that morning).
In the years that would follow, I noticed that after being intimate with Hef, the new girls fell into
one of three categories: the hustler, the runner, or the fighter.
Most of the girls that ended up becoming girlfriends reacted the same way: they were very
nonchalant about their “initiation.” Before the sun even rose the following morning, these hustlers
were already calculating just how many pennies they could squeeze out of the arrangement.
Next, we had the runners. While the hustlers were scheming, the runners were fleeing. Like a hitand-run,
these girls would bolt from the scene, never to be heard from again. While most—if not all
—had hoped to land a pictorial, they disappeared off the face of the planet, never returning for
another night out or party, despite being invited back. The “runners” always seemed like
inexperienced girls, so I assumed they didn’t come back because they didn’t like what they had seen
or done in Hef’s bedroom while under the influence of alcohol, Quaaludes, or both.
My reaction fell into the third category: the fighters. I was freaked out and, frankly, ashamed by
the experience. After disappointing myself like that, I had to come away with something positive,
something to make it right in my mind, somehow. I knew that if I couldn’t find a silver lining, I
couldn’t forgive myself for the night before. The other girls who would react as I did were probably
the most damaged and affected—we couldn’t so easily shrug off what we had been reduced to. It
would haunt us, but in order to move forward we needed to find an upside.
For me, asking to move in therefore seemed like the next rational step—or so I convinced myself
—and I decided to bite the bullet. After all, it hadn’t occurred to me to invite myself out to a club
night until 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.
“Can I ask you something?” I let out another squeak. He looked up at me for the first time and I