Down the Rabbit Hole (9 page)

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Authors: Holly Madison

BOOK: Down the Rabbit Hole
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How these “side boyfriends” felt about their girlfriends dating Hugh Hefner, I don't know. I imagine the girls weren't forthcoming with these men and probably denied that they even had sex with Hef (they denied it to everyone). Most of them referred to “dating” Hef as a big publicity stunt to help them launch their careers. Maybe some of the guys got a perverted little kick out of the fact that they were dating the same girl as Hugh Hefner. Who knows?

Contrary to popular belief, most nights at the mansion were pretty boring. We usually ended up in one of the bedrooms gossiping or watching TV. One night Lisa was hanging out in Vicky's room and the doors to our connecting bathrooms were open. When Tina came to visit, I went into Vicky's room to try and make an effort to be friendly with the girls. Tina was excitedly talking about her “boyfriend,” and like the socially awkward person I was, I asked her, “Do you feel like he even takes you seriously when you live with Hef?”

My intention wasn't to be mean; I actually wanted these girls to like me! I was genuinely curious. When I shared the news that I'd be moving into the mansion, I hadn't met the warmest response, so I wondered how everyone else's friends, families, and even boyfriends felt about it.

Tina whipped her head in my direction and snapped a dismissive response at me. I grimaced and tried to apologize, but Tina wouldn't even look at me. She just rolled her eyes at Vicky.

As you could have predicted, Tina's boyfriend didn't stick around long. In fact, none of the “side boyfriends” ever stayed longer than a few months at most. I don't think the men took them seriously. I always assumed most men were just using the girls to check some Playboy Bunny fantasy off their bucket list. I only ever saw one “side boyfriend” stick around: Hank Baskett.

Following the rules wasn't difficult for me. I didn't know too many people in Los Angeles and I quickly cut out the small group of friends I did have—either because I didn't want to be subjected to their judgment or because they started to call asking for invites to the mansion and other favors I couldn't grant. Plus, I've always been a bit of a homebody and much preferred the delicious home-cooked meals the staff provided to dancing the night away at nightclubs (where I would usually get pretty drunk purely out of sheer boredom). Most of the girls would have rather died than sit around the dining table with men three times their age, but I found Hef's friends funny and interesting, and genuinely enjoyed listening to all of their stories. Eventually, I would convince myself that this was yet another component of the common ground Hef and I shared as a couple.

Usually the movie nights included a steady rotation of Hef's favorite classic films and I adore old movies—something we were truly starting to bond over. Every Sunday night, Hef's office would arrange to have studios bring in movies that were still in theaters—and armed guards would enter the mansion with giant film cans to screen the newest Hollywood blockbuster for us. It was pretty cool, but it also was sort of bizarre, because oftentimes celebrities or other important Hollywood power players would join us for the screenings and be relegated to spending roughly two hours squirming in uncomfortable metal folding chairs. For being a super upscale home, it wasn't without its downscale touches. One of the most memorable was the tray of Johnson's Baby Oil, Vaseline, and Kleenex that was in every bathroom, in the grotto, and at the tennis courts and the pool bar. I still don't know whether to be disgusted or amused by those trays.

At first, my constant attendance at all of the events deemed “boring” by the other girls earned me a bit of good grace with them. They felt that I took some of the attention off their recurring absences while they busied about with their outside lives. Girls would find crafty ways to sneak out past curfew when they thought it wouldn't be noticed—like hiding in the trunk of someone's car as they drove off and onto the property!

While evenings at the mansion were pretty regimented, during the day we were virtually free to do as we pleased. Hef was usually awake by 10
A
.
M
. for breakfast, then meandered down the hall to his office wing, where he would work on the magazine, various book projects, and other business. He wouldn't emerge again until the evening.

In the beginning, I spent most days with Britney—a nice girl that I had met at the Sunday pool parties. We'd go to the gym, tan, lay by the pool, and cruise around L.A. searching for bargain clothes. The only other girl I remember spending time with was Lisa.

Besides me, Lisa was the youngest girlfriend in the group at that time. She lived in Bedroom 2, the largest of the bedrooms, and was still celebrating the release of the issue in which she was the centerfold. She was a cute country girl who, according to the other girls, dated Kid Rock on the side, though I never saw any evidence of it. She had first auditioned for
Playboy
over a year prior to her Playmate pictorial finally being published. Somewhere along the way, she met Hef, became a girlfriend, and secured a centerfold after acquiring a new set of Hef-financed breast implants to lift the mammaries that he'd deemed “too droopy” for a Playmate.

Like most of the other girlfriends, she was both manipulative and manipulated. Becoming a published centerfold didn't happen overnight. In fact, Playmate features were often shot 8 to 12 months before they actually hit newsstands. According to Vicky, Lisa had been a girlfriend for several months before losing patience.

“She threw a fit when we were out one night, asking when she was going to finally shoot her centerfold,” Vicky once explained to me, rolling her eyes and exhaling cigarette smoke. “She's the baby, she always gets what she wants.”

“This is like a boy band,” my friend Britney added. “Hef has to have an old one, a young one, a wild one . . .”

This brought a cackle out of Vicky, who rolled her eyes.

“He always plays the oldest one against the youngest one,” Vicky explained, eager to share her expertise on the topic as we gossiped about the situation. “Tina may be his main girlfriend, but she's older, so he likes to play on her insecurities by playing favorites with whoever the youngest one is. And Lisa isn't special. Before her, he used Buffy to play against Tina.”

I took note of this, but at the time I didn't want to believe a man as old and accomplished as Hef could be that petty and immature. Vicky was starting to show her nasty side, so I wrote it off as jealousy on her part.

Lisa was one of the friendlier girlfriends. In fact, when I walked by her room one morning, she called me in.

“Hey, wanna go to Target with me later? I need to run some errands.”

“Yeah, sure, lemme know what time!” I said, feeling lucky to be invited. I was hoping she could fill me in a little more on how things worked around the mansion, since Vicky and the others had given me the cold shoulder.

“Ugh. I need to get lipo,” Lisa croaked, looking down at her belly and pinching her spare tire. She was adorable, but had been told to lose weight by a
Playboy
photo editor.

“No you don't,” I said. “You look fine.”

“Thanks!” she replied through a toothy grin.

As I knelt down to pet one of her three dogs, she picked up the phone next to her bed, pressed 0 for the butler's pantry, and ordered a piece of chocolate cake and a glass of chocolate milk for breakfast. Was I in the twilight zone? Plastic surgery was so commonplace for these women that liposuction sprung to mind as the obvious weight loss cure before, say, taking chocolate cake out of your breakfast routine.

“Hang out here while I get ready,” Lisa demanded while hopping into the bathroom. After she had chattered on about herself for about 10 minutes, her cake was finally delivered. She thanked the butler, plopped the tray down on her bed, started shoveling the cake in her mouth, and asked, “So, how do you like it here so far?”

Finally, someone I can talk to!
I thought with relief. Now was a good time to ask a few questions and confess a few of my insecurities about this wild world I had just entered. I confided in Lisa that I wasn't too fond of April, that she really intimidated me.

“That's okay, the rest of us don't like her, either,” Lisa stated, wrinkling up her nose. “Hef just likes her because she's wild.”

“Oh, wow, thank God it's not just me!” I sighed, feeling relieved. Maybe April wouldn't last that long and then we could all really be like sorority sisters; all on the same team.

Feeling more and more comfortable with Lisa, I thought I would ask her opinion about something that had started worrying me the past few days.

“Hef hasn't given me a bunny necklace yet,” I admitted meekly. “Do you think that's weird?”

Every Playmate and every girlfriend was presented with a bunny pendant necklace from Hef. At the time, I (along with everyone else in L.A.'s 30-mile zone) thought these necklaces were made with real diamonds. They had looked so glamorous, glittering on the chests of the chosen ones who flitted about the Playboy parties, the hottest nightclubs, and the spendiest shopping districts in L.A. (In reality, the pendants were cubic zirconia, and if you could track down the Downtown L.A. jeweler who made them, anyone could purchase one for just $100.)

My interest in acquiring a necklace had nothing to do with its value, however. Sure, I coveted one, but my worry stemmed from what it symbolized.

Hef's words echoed in my mind: “You can stay for a while and we'll see how it works out.” Maybe I wasn't making the cut. That had to be why he hadn't graced me with a necklace yet. In the few weeks I had been there, he had presented one to Charis Boyle, an upcoming centerfold, whom he had met after me. Somehow I had been skipped over.

“Oh, he hasn't?” Lisa asked, feigning amazement. “Ohhhh. Yeah, I dunno why that is.” She purred as she put down her fork and sauntered back into the bathroom.

I felt a knot form in my stomach. That was definitely not the reaction I had hoped for. Lisa's sisterly vibe had me hoping she would reassure me that this was normal or perhaps even offer to ask
for
me—after all, she seemed so comfortable around Hef and was certainly good at getting whatever she wanted.

As Lisa readied herself for the day and led me down to her car, my mind was in turmoil. Was my time here almost over? I had barely been at the mansion two weeks and already I didn't seem to be making the cut. What would I do now?

As it turns out, I wasn't the only one with these kinds of anxieties.

As we wound our way through L.A. traffic down to Target in Culver City, Lisa kept babbling about herself. I found her stream-of-consciousness narrative fascinating, as her anxieties mirrored mine. The only difference was that she had been here longer and had a centerfold under her belt.

“See this?” she bragged, holding up her checkbook for me to see the balance, which hovered just above $25,000.

“It's the money I earned doing my Playmate pictorial!” she exclaimed proudly. “I haven't touched a penny! You know, the other girls aren't even thinking. They have Hef leasing them cars they could never afford and they spend money like there's no tomorrow.”

She looked pleased with herself.

“Everyone made fun of me for getting this car,” she said, patting the steering wheel of her brand-new Toyota RAV4. “But I want something I can afford after I move out. I don't need a Porsche.”

Smart,
I thought. In fact, it was the first sensible thing I had heard out of any of the girlfriends' mouths so far.

As we roamed through Target, she filled her shopping cart with everything from a nose hair trimmer to dog toys. “I always spend so much at Target,” she sighed. “You always walk out of here with more than you need.”

I smiled and nodded my head in agreement. Before another pause could pass, Lisa started babbling again.

“You know, I don't know if I could ever go back home,” Lisa continued. “One of my guy friends from home, the other day he got real rude with me on the phone and said the only reason I got centerfold was because I fucked Hef.”

I wasn't 100 percent sure if she was even talking to me anymore—or just thinking out loud.

She shrugged her shoulders and tried to offer a halfhearted smirk, but I could tell the comment bothered her deeply. I could certainly relate. Like me, I think she got into this situation without quite realizing what a public decision it was.

“It's not true. You're gorgeous,” I offered, trying to cheer her up. “You could have become a centerfold anyway.” And it was true. She was curvy, cute, and baby-faced, resembling a petite version of Anna Nicole Smith.

“Thanks,” she sighed, offering a weak smile. “But I can't go back home. I mean, what am I supposed to do? I'm not above working a real job, but, like, if I'm working at a counter somewhere everyone I know is gonna come up and be like ‘ohhhhh, Lisa, look where you are now after posing naked.' It's embarrassing.”

I was just as anxious as Lisa was about the life that waited for me outside the mansion gates. So many things seemed to be grounds for dismissal that I was petrified to step out of line. While becoming an actress was still a passion of mine, it was always best to keep any auditions quiet. After Brande Roderick had left Hef for
Baywatch Hawaii
, he kept a much closer eye on any acting work the girlfriends tried to pursue. I secretly hoped to land a role big enough that it would allow me to leave the mansion after a few months, but those kinds of dream jobs are few and far between. Eventually I would receive offers for smaller parts in music videos and low-budget films—but the hours often went past our curfew and the jobs rarely paid much, so they hardly seemed worth it. If anything, they would only land me in hot water with my boyfriend who, as the weeks passed into months, appeared more and more controlling. It seemed my acting dreams were stalled for the time being. I felt caught between a rock and a hard place. I thought having a rent-free roof over my head would make chasing my dreams so much easier, but that wasn't turning out to be the case.

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