Down the Rabbit Hole (20 page)

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Authors: Holly Madison

BOOK: Down the Rabbit Hole
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When we got back to the mansion, I went out to the room in the guesthouse where Kendra was staying, holding the new blue dress. I told her it was hers to wear if she wanted and that Bridget was wearing a pink one and I had a pale orange version.

“Oh my god, girl!” she said, I could see the relief on her face as a big toothy grin emerged. “You have no idea. I was going nuts.” She thanked me profusely. For the first time in a long time, I felt as though I could relax. I had a good feeling about this one. Just because Hef didn't want another Bridget or Holly didn't mean we couldn't all be friends. I wanted her to feel welcome.

Realizing that the opportunity might soon present itself, Kendra began asking questions about life as a girlfriend as she changed into the dress. She had already hooked up with Hef, so that part was no mystery.

“Can I bring my dogs when I move in? I have to bring my dogs,” she stated. “I have two dogs. I need a really big room.”

“I don't know what room you will get if you move in,” I said. “That's up to Hef.”

I have to admit, I envied Kendra's sense of entitlement. I had felt so lucky just to scrape by when I moved into the mansion, and here was a rookie who had just gone all the way with an old dude and her only concern was how big her room was going to be.

Though she wasn't as cunning or sophisticated as the other girlfriends who had inhabited the mansion in recent years, she seemed to have that same hustler mentality. Kendra was a stripper but had told Hef she was a college student, because the body painter gave her the heads-up that Hef didn't like strippers and preferred college girls. When Hef put a caption under one of the first photos of her that entered his scrapbook, he referred to her as “Hef's new sweetheart: a 19-year-old coed from San Diego.”

“I need a car, too, if I'm gonna live here,” she barked. “I don't have one. And I want to get my teeth fixed. They are the only thing about me that I don't like.”

The balls on this girl,
I thought.

“Oh, you'll have to talk to Hef about that,” I responded, shrugging my shoulders. I barely had the nerve to ask for anything for myself—I certainly wasn't going to ask for her.

The Easter ensembles worked. About a month after Hef's birthday, the Mean Girls were finally given the boot and Kendra was officially asked to be a girlfriend. After three years of misery, which at the time I felt was largely due to those bullies, it was over. They were gone—and I'd never have to see or hear from them again! It didn't really feel real. I actually went down the hall and peeked into each of their former bedrooms to make sure they were really gone.

“What did you say to them?” I asked Hef when he told me the girlfriends were leaving. I couldn't be certain that my prompting actually had anything to do with Hef's decision, but I silently congratulated myself either way.

“I told them that Kendra's moving in and Kendra had confided to me that she used to have a drug problem,” he said, nonchalantly thumbing through a file folder he had in his hand. “Kendra told me they took her out to a club and offered her drugs. I told them I couldn't have that around her.”

Of course,
I thought. I wasn't sure how they managed to sneak out of the house with Kendra, but according to her story, they did. If the story was true, the Mean Girls must have seen exactly what was happening and made a last-ditch effort to save their asses and sabotage Kendra's chances. Thankfully, it backfired.

Kendra's arrival was the best news I had in a while! I was ecstatic to have those days of drama and backstabbing permanently behind me . . . or so I thought.

J
UST AS HE HAD
done with me when I first arrived, Hef quickly made Kendra his “golden girl.” After all, she was the youngest and newest member of his harem.

Immediately, Kendra acquired a black Escalade that she “pimped out” with rims, speakers, and every extra accessory possible. She also snagged the room she wanted, Bedroom 2. It was the largest, most luxurious, and most plush of all the bedrooms—and she would instantly trash it. Kendra's room turned into a junk-dump of possessions and reeked so badly of dog urine that you could smell it down the hall. I always tried to avoid staying in her room longer than a few minutes.

Since the house was virtually empty, I decided to ask Hef if I could use Bedroom 5 again so I could have more room for my things—and a little privacy when I needed it. Living in the “Vanity” made me feel on edge. Hef's secretaries were constantly in and out of there throughout the day, adjusting his calendar and wooden box full of pictures. I liked all of Hef's secretaries, but I would have liked a little solitude, too.

“Absolutely not!” Hef squawked, setting down his reading glasses. “Do you have any idea how much those rooms cost to rent?”

Actually, I did. Playboy Enterprises (a public company at the time) owned the mansion. Not Hef. In order to live there, he had to pay a monthly rent on every room he and his girlfriends occupied. People may find it surprising that Hugh Hefner is nothing more than a tenant renting his room at the mansion, but that's exactly how it is. At the time, he paid approximately $25,000 a month for the master suite, $12,000 a month for Kendra's room, and $10,000 a month for Bridget's room (Bedroom 3). The three smaller rooms were priced between $5,000 and $7,000 a month. Should any of the rooms be vacant, Hef wouldn't be charged for them.

So Kendra's worth $12,000 and I'm not even worth $5,000,
was what I took away from the conversation. Since I lived in the “Vanity” corner of Hef's closet, he didn't have to pay any rent on my account.

Despite these little annoyances, things were actually going smoothly in the house between Bridget, Kendra, and me. To my great relief, Hef mentioned to his immediate circle that he was “downsizing” to “just” three girlfriends. Just when I thought this new “quality over quantity” arrangement might mean less drama, Hef decided to drop a bomb on us all.

During a Fun in the Sun pool party, Bridget and I were reading and sunning ourselves on side-by-side lounge chairs while Kendra sat on a floatie near the edge of the pool. As Hef shuffled along the flagstone walkway between us carrying his backgammon board, he paused and looked around at each of us.

“You know,” he began, taking a swig from his bottle of Pepsi, “I've decided I'm going to do a pictorial on the ‘Painted Ladies,' featuring you and Tiffany.” He nodded towards Kendra, but spoke loudly enough for us all to hear.

“Oh, wow!” Kendra shouted. “Thanks!”

Pretending we didn't hear a word, Bridget and I kept our noses buried in whatever we were reading. We didn't know what to say.

“I just want to put my book down and leave,” I said defeatedly. “He knows how badly you and I want to be in the magazine and he just had to make that awkward announcement in front of us?”

“I know,” she sighed.

We knew that Hef was trying to make us jealous and feel like shit, but I felt helpless, like there was nothing I could say.

One particular day, Kendra appeared a little more somber than usual. Like all of us, she had her rough days—especially in the beginning—and we tried to coach her through, but that day she seemed really depressed. Bridget and I were desperate to win Kendra over and create the “happy family” we had always wished we had at the mansion.

“We're going out tonight,” I declared, popping my head into her room. Immediately, Kendra's eyes lit up. Clearly, she needed a night away—even if only until 9
P
.
M
.

Hef was hosting his “manly night” at the mansion, which meant the girlfriends were required to make themselves scarce. Bridget and I thought it would be fun to take Kendra out for dinner. She was still new to Los Angeles, so we thought taking her out on the town would be just what she needed to lift her spirits. We decided on Nic's, a popular martini lounge in Beverly Hills, for appetizers and cocktails.

When evening finally rolled around, Kendra seemed elated to be outside the mansion gates
without
Hef's parent-like supervision.

“Girl, do you think there's anyone famous here?” she sort of shout-whispered in my general direction, craning her neck to see if she could spot a celebrity tucked into one of the restaurant's dark corners.

“I'm going to get a cocktail,” I suggested, thinking we should toast our first-ever girl's night out. Nic's was known for their creative cocktails with their cleverly punny names, like “Last Mango in Paris” and “Coco Cabana.” Bridget and I each ordered some fruity concoction as Kendra pored over the menu with a furrowed brow.

When it came her turn to order, Kendra announced that she would be having the “Sake to Me.”

“Excuse me?” the waitress asked, clearly not understanding the order. Kendra had mispronounced the Japanese rice wine by saying “sake” as if it rhymed with “take.”

“The ‘Sake to Me,' ” Kendra repeated, the same way she had pronounced it the first time, only slower and more aggressively. I felt myself wince.

The waitress appeared generally perplexed. I shot Bridget a look, but she was already making herself busy with the cloth napkin. One of my biggest pet peeves is people who are rude to servers. I could sense Kendra's frustration getting the best of her, but before I could intervene she groaned and snapped the menu off the table, pointing firmly to the drink.

“The ‘Sake to Me,' ” she barked, once again mispronouncing the main word.

“Oh, the ‘Sah-keh to Me'!” the waitress echoed, clearly relieved that she finally understood what Kendra was getting at.

“Yeah, that's what I said,” Kendra jeered, looking back at the table.

Unfortunately, the Playboy Mansion was a breeding ground for that kind of arrogant behavior—especially among Hef's girlfriends. And shortly after, Kendra's began to take off.

One day when I was out shopping, I fell in love with these adorable skirts at Bebe that I knew Bridget and I would both love. They were mid-length, flowy, and dripping in sequins. I picked out a pink one for Bridget and a cream-colored one for myself. I wanted to make sure that Kendra didn't feel left out, so I picked up the baby blue version for her.

When I got back to the mansion, I found Kendra in her room and handed her the bag.

“I found these really cute skirts today and picked them up for us in different colors. I thought we could wear them out to the club tonight if you want to,” I said, helping myself to a seat at the edge of the bed.

Kendra lazily pulled the skirt out of the bag and ripped the tissue off from around it. She held it up for a moment before shoving it back into the bag.

“Yeah, I don't really like it,” she said, wrinkling her nose and handing it back to me.

I ignored the glossy black bag being shoved at my face. Sure, I didn't want to be a clone, either, but couldn't she just have said thanks and tucked it into her closet? Up until this point, Bridget and I hadn't been on the receiving end of her snotty remarks, so I was a little surprised at the direction this conversation was taking.

“Well, I got it for you because I didn't want you to feel left out,” I added.

“I won't wear it,” she snapped back, dropping the bag to the floor and turning her attention back to the TV that so frequently occupied her hours.

“You don't have to,” I said finally and walked out her door, leaving the bag on the ground. Honestly, my feelings were hurt. I went out of my way to do something nice for her and it came back to bite me in the ass. I felt like I was damned if I did and damned if I didn't. I'm not sure if she ever wore the skirt. It's probably still sitting in Bedroom 2's closet.

Later that evening, after spending roughly 45 minutes twiddling our thumbs in the great hall waiting for Kendra to grace us with her presence, she finally emerged from her bedroom looking like a petite sex kitten in a red spandex dress, Lucite platform heels, large blond barrel curls cascading from her head, and bright, candy apple red lipstick applied with perfect precision.

Immediately I cringed.

Oh shit,
I thought.
This was going to be bad
. Bridget quickly shot me a knowing glance, her eyes wide with concern. As Kendra sauntered down into the foyer, I braced myself for impact.

The last time I had tried to wear red lipstick was two years earlier, the day I had cut my hair and Hef had bit my head off for it. It was such a memorable moment that when Kendra appeared in the main entryway with her lips painted bright red, my entire body tensed. It had been two years since Hef's reprimand, but the humiliation still burned inside me.

I could tell that Hef was already irritated that she kept us waiting this long and now seeing the red lips . . . he was
not
going to be happy.

Slowly he made his way to his newest girlfriend to more closely scrutinize her face. My jaw clenched as he inched toward her.

What horrible thing was he about to say?
I thought. I looked down at my hands and squinted my eyes. After what felt like an eternity just waiting for him to erupt, he finally let out a big guttural laugh.

My eyes sprang up to make sure I was hearing this correctly.

“Why, that red lipstick looks absolutely
wonderful
on you, Kendra!” he boomed, grabbing her arms and kissing her on the cheek. “You look like you just stepped out of a 1940s movie!”

I looked over to Bridget, who had the same surprised look plastered on her face that I was sure I had on mine. Surely he was being facetious and was about to unload on her, right? Not only did he not despise the look, he thought she looked “wonderful.”

My head was spinning. Kendra and I were not
so
unlike that red lipstick could have looked that much better on her than it did on me. What about Bridget? Tina? Vicky? April? Or any of the other five dozen girls who were told never to wear the hue?

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