Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny

Home > Other > Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny > Page 15
Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny Page 15

by Holly Madison


  “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?

  I was waiting for the other shoe to drop when the house photographer gestured for us all to line up for a photograph, but nothing more was said. Did I somehow manage to stumble into an episode of The Twilight Zone?

  “Are you kidding me?” I whispered to Bridget when we finally piled into the limo. I could feel the hurt boiling inside me.

  She just shook her head.

  “So he just loves red lipstick now?” I asked sarcastically. How could his decades-long opinion transform so suddenly with one girl? I was crushed. That was the reaction I had thought I would have received years earlier. Over such a minor thing, I was belittled and made to feel like trash. But Kendra did it and gets praised? I didn’t resent Kendra; it wasn’t her fault. It was Hef who made me mad.

  All the Playmates who were waiting to go out with us noticed how taken aback I was. That’s one of the things about Hef: when it came to humiliating his girlfriends, the larger the audience, the better.

  “I think he was trying to get to you,” one of the girls whispered, pretending to search through her purse. “I don’t think he really likes it.” It was he
r way of trying to comfort me.

  Seriously? I thought. Sure, Hef had a habit of pitting the youngest girl against his main girl; that tradition had been going on since the days of “Mama Hen” Tina and “Baby Face” Buffy, but this was sick. Was he really trying to stir up my feelings of inadequacy by praising a 19-year-old? I was only 25, which was hardly ancient (unless you’re talking to Hugh Hefner).

  “There’s no way he remembers,” I said, only half believing my own lie. “It was like two years ago.”

  “Holly,” she said, taking a moment to meet my eyes. “You know he remembers everything.”

  I stared back at her and let this sink in. She was right. He knew exactly what he was doing. He catalogues shit like that for just these types of moments. Men don’t achieve his kind of power and success by being idiots. He didn’t want a big, happy family of girlfriends that all got along. He wanted multiple women frothing with jealousy and animosity towards each other. It was a part of his control game. I could never accuse him of doing it on purpose, because he would simply brush off my accusation by declaring how preposterous it all sounded. And he’d be right. It does sound insane, but that didn’t make it any less true.

  Quickly I shut off my pride and put on the biggest smile I could muster. If he can pretend he doesn’t remember, I can too. I can’t let him believe he succeeded; he wouldn’t use Kendra as a pawn to get the best of me. But believe me, he would end up trying.

  DESPITE MY ATTEMPTS TO befriend Kendra, she continued to push me away. Hungry for her own “team,” Kendra desperately tried to make each new Playmate who arrived at the mansion her friend—and her friend alone. Kendra’s plan rarely worked, though. Most of the new Playmates were nice girls who were eager to get to know all of the girlfriends. And, let’s face it, Kendra wasn’t the easiest person to have a conversation with. When the new Playmates would make an effort to spend time with Bridget or me, they were confused when Kendra suddenly lost interest in being their friend. A girl was not allowed to play both sides of the fence, so Kendra would toss her aside and find the next person to entertain her.

  And as is true with any caged animal, it was dangerous when Kendra grew bored.

  Her frustrations had been mounting for a while. She had been at the mansion for a few months, and Hef hadn’t asked her to be a Playmate yet. Even though she was well aware that Bridget and I had never been in the magazine, she thought she was somehow different (perhaps because of the “Painted Lady” pictorial she posed for in the September 2004 issue) and couldn’t understand why she wasn’t already on the cover.

  “I’m locked down,” she would frequently say, referring to her new life behind the gates. It’s no secret that Kendra was a pretty hard-core party girl before coming to the mansion. She battled drug addiction throughout her teenage years and eventually became a stripper to make extra cash. When Hef finally asked her to move into the mansion, Kendra thought she hit the jackpot. After all, wasn’t Playboy all about excess? Money, parties, and sex.

  But, as she quickly realized, those nights were few and far between—and rarely as much fun as you’d think. The public’s image of the freewheeling leave-your-inhibitions-at-the-door atmosphere of the Playboy Mansion was not a reality for any of Hugh Hefner’s girlfriends. The atmosphere resembled the court of Versailles, with each guest obsessed with rank and standing. There was even a hierarchy among Hef’s friends when it came to seats at the dinner table. At 19 years old, Kendra was stuck with a 9 P.M. curfew, a 78-year-old boyfriend, and a stricter set of rules than she had ever had at home. And now, adding insult to injury, she was finally realizing that she wasn’t as special as Hef made her believe. She was just another blond girlfriend—and life at the mansion wasn’t all she imagined it to be.

  Much like the battle I endured—and ultimately lost—years earlier, Kendra was desperately searching for an identity of her own. Being a clone was soul sucking; you were simply another blond number on Hef’s arm.

  In the beginning, Kendra was very quiet. The raucous deep-throated cackle that became her trademark on GND was something she affected in order to stand out. I know I have no place to talk when it comes to annoying laughs, but with Kendra, it was clear she was just being as loud as possible in order to make sure every head in the room turned her way.

  “Why is Kendra laughing like that?” one of the visiting Playmates had asked me, unaccustomed to the new sound. “She’s so annoying! If no one is paying attention to her, she just screams out of the blue!”

  I just shrugged my shoulders, hoping it was just a passing phase. But Kendra wouldn’t shut it off until she was certain all eyes were on her. The laugh never did vanish, though. Even today she still adopts that cackle. I bet by now it’s almost natural. Almost.

  Eventually, these sort of exaggerated antics became her trademark. For example: flying. She claimed to be so terrified of flying that she would put on a massive show in front of Hef during takeoff that resembled a loud, prolonged, frightened orgasm. It was embarrassing to witness. And wouldn’t you know, when we were finally able to fly with Kendra on our own (read: without an audience of men for her to perform for), she was remarkably calm during the entire flight.

  Kendra had been living at the mansion for close to a year when my patience finally started to wear. We were all out at the nightclub of the moment in Hollywood with some potential Playmates. Bridget and I flanked Hef in a corner booth while the other girls danced and partied around us. Always trying my best to be as attentive as possible, I remained seated next to Hef the whole night, drinking and watching the clock.

  Immediately, Kendra hoisted herself to the top of the banquette. Surrounded by the Playmate posse (all of whom were her BFFs on this particular evening), Kendra put on a show dancing as provocatively and wildly as she could until she was certain every set of eyes in the nightclub were focused squarely on her. In all of her theatrics, Kendra didn’t notice the large candles near her feet. One minute she was shaking her ass and the next a cascade of hot wax was scorching down my leg.

  I jumped to my feet and began swiping at my thigh. Kendra took a brief moment to take in the situation before turning her attention back to the other Playmates and letting out a long, loud laugh, not even taking a moment to apologize.

  Hef was oblivious to what had just happened—recognizing that something was wrong only when I stood up and started peeling the wax off my leg. He finally asked what had happened.

  “Kendra dumped hot wax all over my leg,” I said angrily. “She knocked that candle over while she was dancing, looked right at me, and didn’t even apologize.”

  “I’m sure she didn’t mean it,” Hef said, ignoring how upset I was and turning his head back towards the crowd dancing in front of us. He decided it was time to leave a few minutes later. Thank God, I thought. I just wanted this night to be over so I could forget about this latest humiliation, just as I had tried to forget all the others I had experienced since joining the mansion fold.

  As we navigated our way through the sea of gawkers, we were stuck in an absolute traffic jam. Picture Hugh Hefner, roughly 10 girls, and a handful of security guards trying to push their way through this dark, tiny, crowded nightclub. It was a nightmare. Not only was I angry and irritated, but my skin was still burning from where the wax had landed.

  Kendra was bouncing along behind me, laughing and dancing with the other Playmates as we made our way to the door. She must have sensed my irritation (how could she not?) but still said nothing. Instead, as soon as our group stalled, she threw up her hands and screamed at me: “Move, bitch! Get out tha’ way!”

  I whipped my head back around and screamed right back. “Shut up!” I yelled in her face. “You spilled hot wax on me, don’t say anything, and then call me a bitch? FUCK YOU!”

  Kendra’s smiled faded and the Playmates got quiet. I never lost my cool like that, so everyone knew I was seriously pissed.

  “What?” she said, her eyes like saucers and looking from side to side at the other girls, gras
ping for some kind of support. “It’s a song.”

  It hurt enough to have to be constantly humiliated by Hef, but now I had to take it from a 19-year-old bimbo who I had been nothing but welcoming to? I was losing my patience. When we finally made our way to the door, I turned to Hef.

  “She’s totally inconsiderate,” I grumbled. “How could she not even say she was sorry?”

  I took my seat in the back of the limo, and much to my surprise, Hef finally opened his mouth.

  “You know, Kendra, you really should apologize to Holly,” he said, in a sort of fatherly, condescending tone.

  That’s when the train went off the tracks.

  Kendra burst into tears—a hyperventilating, sobbing mess of tears.

  “You guys are my family,” she wailed, reaching for the bottle of vodka from the limo bar. “I’d stick up for any of you guys no matter what!”

  She pulled off the cap and started downing the vodka. The entire limo fell silent. In between swigs, she cried and blurted out some mumbo jumbo through sobs that no one really understood.

  One of the girls tried to calm her down, but Kendra was either too drunk or too crazy to control herself. Hef, Bridget, and I fell silent before telling her that we would be there for her, too. The whole display was shocking and kind of sad.

  It simply wasn’t normal. It seemed as if Kendra, finally finding herself on Hef’s bad side, broke down and retreated into a drunken fit. Like a toddler throwing a temper tantrum, she guzzled down the vodka in hopes that Hef would feel that urge to rescue her or care for her. It was both manipulative and incredibly sad. From that night forward, I was always a bit more cautious with Kendra. A woman who allows herself to enter into a situation like the one we were in must struggle with personal demons—I know I did. Kendra was harmless, sort of like an annoying kid sister. Our relationship would have its ups and downs over the next few years, but I learned to pick my battles and appreciate that she was just as damaged as the rest of us. She just had a different way of showing it.

 

‹ Prev