Down the Rabbit Hole - Holly Madison

early days of Hef’s seven girlfriends, it was standard practice for the girls to call in the Playboy glam
squad before evenings out and large parties. By the time I arrived on the scene, these were the kinds
of lavish expenses that Hef had cut back on. Sure, we would occasionally head to the salon before a
red carpet event, but we had never yet experienced the crème de la crème. The Playboy glam squad
was legendary. It comprised some of the best artists in the industry—and they didn’t come cheap.
The ultra-talented Kimberly Ex did my hair and makeup: full, barrel-curled platinum locks with
a bronzed face, defined cheekbones, thick black eyeliner, and carefully drawn lips. From the neck
down, we were expected to be in top physical shape. The only help we were given in that area was
some baby oil mixed with bronzing lotion to give our skin a smooth sheen. I was over the moon with
my reflection. I mean, I actually looked like the girls on the pages of Playboy! First, we shot a series
of clothed setup shots, which included a shot of the three of us hula hooping on the great lawn in
bathing suits. It was mostly intended to warm us up before diving into the deep end (naked), but they
ended up coming out great and one of the shots was published. The next setup had us in sexy cocktail
attire standing in front of Hef’s limo in the mansion’s main driveway. After a few minutes of shooting,
Hef appeared on set to join us for a few snaps.
How cute, I thought, he wants some behind-the-scenes shots of our shoot for his scrapbook.
Finally, it was time to begin shooting our nudes. By that point we’d each become considerably
more relaxed in front of the camera. As Arny positioned each of us along the rocks in the mansion’s
infamous grotto, we were all laughing and goofing around. It was easily the best time the three of us
had had together in what felt like months. When Hef came out to check on the photos, he was so happy
with the results that he added a last-minute setup for the three of us in the bathhouse shower. It was
already pretty late in the day—the shoot had gone longer than intended—but I couldn’t get enough.
The crew began setting up a final shot, but Bridget was scheduled for school. She had a final exam for
one of her classes that she couldn’t get out of. Apparently her professor didn’t qualify shooting a
Playboy pictorial as an acceptable reason to miss class. After a few minutes debating whether or not
she should just skip (which would have resulted in a failing grade), Bridget dashed off to campus for
her test.
Truthfully, it didn’t feel odd shooting without her. I knew they wanted a lot of content to choose
from and we still had the rest of the week to finish our pictorial. As far as any of us knew a
“Bridget/Kendra” or a “Holly/Bridget” setup could have been on the books for the following day.
Plus, shooting with just two girls was much easier than trying to arrange three. With wet hair and
perfect makeup, Kendra and I playfully lathered each other up with sponges and bubbles in the
tropical rock shower. Because it was one of the easiest sequences, it resulted in some of the sexiest
shots of the entire pictorial.
The following day was hands down my favorite. The photographer and crew buzzed around the
mansion’s second floor preparing for our individual photos. Set in each of our bedrooms, the shoots
were designed to showcase our unique personalities, which was refreshing. To reflect Bridget’s
sweet and playful demeanor, her pictorial featured her swathed in a delicate see-through negligée
surrounded by plush pillows in her pink-on-pink-striped room. Kendra looked absolutely amazing in
a scrap piece of football jersey with knee-high athletic socks and straddling a bunny head chair in her