Feeling so cocky after the video shoot, Jessica had said, "I bet I could beat even a Playmate in a real wrestling match!!"
Word of her comments reached the ears of Hugh Hefner himself and he quickly had his daughter Christy, the CEO of Playboy Enterprises to find one of the girls who'd take up "The Challenge."
Christy, of course, only approached one woman, Karen McDougal and Karen said, "Yes!"
K-Mac issued a statement through Playboy, basically saying, "Jessica Simpson had better either Put Up or Shut Up!!"
Jessica couldn't believe she was being called out, especially by a Playmate nearly a half a foot taller than herself!! Still, despite her husband's pleading, Jessica agreed to meet McDougal in a pro-style ring but only after Christy Hefner and Playboy Magazine signed her to a lucrative contract to appear in the magazine...at some future date!
The match was held in an exclusive gentlemen's club in Las Vegas and as an extra inducement for those in attendance who had paid a hefty entrance fee - or were watching the special PPV telecast on the Playboy Cable Channel - both women would be starting the match topless!
Jessica walks down the aisle wearing a hot pink thong, already totally topless, her big breasts jiggling provocatively as she strides through the crowd with her head down, looking like she's going to a funeral - HERS!!
Next, the song "Hit Me With Your Best Shot" blares from the speakers as Karen McDougal appears and heads down the aisle to the ring and from the look on her face, it's clear she's intent on destroying Jessica Simpson!! K-Mac is wearing a black leather thong and when she steps into the ring, K-Mac fixes Jessica with a cold, hard stare!!
Both women are wearing black, low-cut wrestling boots and Karen's pair has a skull & crossbones on the sides! Jessica, looking worried already, peers around the ring and asks the MC, "Where is the ref??"
The MC looks at her and shrugs, "The man you pissed off specified there be NO referee for this match!!"
As soon as the bell rings, both women began to circle each other to feel her opponent out. Karen has a huge advantage in size and experience and she's hell-bent on making the blonde singer look silly so she stops the pre-action dance, places her hands behind her back and juts out her jaw.
"OK bimbo, I'm in a benevolent mood, so I'm going to let you have the first shot free of charge," Karen hissed.Jessica was a little apprehensive, she already felt she was in over her head from the moment the big Playmate entered the ring and removed her robe to reveal her tanned, and muscle toned body. "Let's go bitch I haven't got all night; I've got a date with an Irishman after I shower....assuming I even work up a sweat!" Karen demanded.
That must've hit an exposed nerve - or maybe Jessica figured this would be her only chance for success but while Karen was still posing, the petite blonde reared back and jumped into a punch aimed right at the side of Karen's face. (Hey, why look a gift horse in the mouth, right?)
Karen's head snapped to the side and everyone in the arena gasped at the explosiveness of the blow. Karen staggered and Jessica moved in, using her forward momentum to get everything behind a ripping right to the breadbasket that folded the dazed Playmate in half when it introduced Karen's belly button to her spine! With Karen jack-knifed and out of breath, Jessica grabbed two handfuls of Karen's perfectly coiffed hair, holding her head steady as she fired a knee up into the brunette's forehead. The Playmate of the Year pitched over backward and crashed to the mat flat on her back. As she lay there with her eyes slightly crossed, Karen wondered what the hell was happening...this was supposed to be a walk in the park! At ringside, Christy Hefner leaped to her feet applauding Jessica's unexpected success while Karen's eyelids fluttered and she tried to clear the fog from her brain. As soon as her baby blues began to focus, Karen saw Jessica looming over her ready to resume her attack.
Looking to regroup, Karen rolled out of the ring under the bottom rope, landing on her ass right at the feet of the grinning Chrisy Hefner! Karen's supporters were in a state of shock. Nobody had left their seats to use the bathroom or get a beer, figuring the 'one-sided' fight would be over in a heartbeat, then they could run off to take care of any personal needs before the next fight on the card. Apparently, the fight was going to last about a heartbeat, but not with the result they'd expected! On the other hand, Jessica's supporters - albeit few in number - were going nuts; including many who had expected Karen to easily dominate the match, but had still been unable to bring themselves not to take advantage of the near 100-1 odds. Like Jessica's die-hard fans, the punters too had felt their hearts drop the minute Karen disrobed and they saw her muscularity. Not that they feared for the safety of their favorite singer, they were just certain their 'sucker bet' had proven to be exactly that. Now, however, they were returning the ribbing they'd taken from the Playmate backers earlier - and in spades!
Karen's head was beginning to clear and she was about to make her way back into the ring to end this fiasco when she was grabbed from behind by the hair as she approached the ring steps by a brunette sitting in the front row with Christy Hefner sprang out of her seat and reached for her.
"You look a little lost, honey; here lemme help you!" the young woman said as she slammed Karen face-first into the corner ring post, stunning her. Then she rolled Karen's body into the ring under the bottom ropes.
"Thanks Sis!" Jessica yelled to Ashlee. "I'll take it from here!"
Karen was flat on her back and laying still as Jessica, full of confidence at this point, signaled to the MC calling for her music. Over the PA system "Arena Girl" began to blare while the sexy blonde vixen did a seductive little dance as she stood straddling Karen's body. Karen rolled over onto her stomach and slowly pushed herself up to her hands and knees, then began to crawl away from Jessica, who stepped back to let her up. But then Jessica yelled and made an animated slashing movement with her hand across her throat, a sign to the PA operator to 'kill' the music.
As soon as it stopped, Jessica screamed, "NOW THE OTHER ONE!"
She swaggered over behind the slowly crawling Playmate as "Hit me with your best shot" exploded out of the speakers!
"OK! Have it your way...you think THIS is my best shot?" Jessica growled, then fired a solid kick squarely into Karen's upturned ass that buckled her arms and sent her skidding painfully over the rough canvas on her bare breasts! She came to a stop at the edge of the ring, sprawled with arms and legs akimbo, her head just under the bottom rope where her disheveled long brunette hair hid the pained expression on her face. Jessica walked over to Karen with an exaggerated swiveling of her hips, paused and stared down at the skull and cross bones on Karen's boots.
"You're certainly not much of a pirate," the blonde mocked. "So you must be the pirate's wench!" She stared in undisguised admiration at Karen's long strong legs, her gaze slowly working it's way up the length of the Playmate's perfectly proportioned gams until her eyes stopped at Karen's ass, checking out the leather thong. "OK tough girl, let's see what you got!" Jessica grunted as she dropped her ass down on the back of Karen's thighs.
With Jessica pinning her legs, the Playmate was pretty much not going anywhere when Jessica began to rake her newly manicured-to-a-sharp-point nails along the back of Karen's legs from the bottom up to her thong! There, Jessica turned her hands palms up and slid her fingers under the thin leather, got a good firm grip, then pulled up harshly, forcing the tough material deep into the crack of Karen's ass and between the swollen labia of her pussy. The sudden violation caused Karen a lot of pain and although she'd had painful wedgies in fights before, in most cases the material failed and gave way - offering instant relief. But with a thong made of genuine leather, that wasn't going to happen...at least not anytime soon! The intimidation factor of wearing leather had long passed and now Karen was the one paying the price for making a fashion statement!
As Jessica reared back pulling, tugging and yanking on the thong, Karen lifted her head off of the canvas and let out a loud howl, reaching back and desperately trying to grab Jessica's hair to get the blonde off her and end the attack on her nether regions. A few times her hand came close and once she slapped Jessica's face as the singer tried to duck, but finally the brunette Playmate was able to latch onto the golden locks and she began to pull Jessica off to one side.
At ringside, Ashlee heard her sister's cry of pain and sprang out of her seat, reached between the ropes grabbing Karen by the hair and pulled her head down over the bottom rope, choking her as Ashlee put both feet against the ring supports and started hauling down on Karen's long, brown hair. Karen instantly released Jessica's hair to grab Ashlee's offending hands, digging her nails in and trying to force her to break her grip. Ashlee yelped in pain and dropped to her knees, but she held onto Karen's hair and as she dropped, she nearly decapitated Karen when she slammed her throat on the bottom rope.
Karen was in big trouble, and without a referee, nobody would be coming to her aid anytime soon! As Karen continued to gasp and gag trying to get air in her lungs, Jessica released her wedgie and scooted higher up Karen's body until she was seated on the Playmate's exposed ass cheeks. Seeing that sister Ashlee had Karen well in hand, Jessica took a moment to fondle her breasts and tweak her stiffening nipples. The sweaty, hand-to-hand combat with another beautiful woman was turning Jessica on like nothing had ever done before! Her heart raced and her sexual desire went through the roof! Jessica released her own breasts and her hands made their way around Karen's ribs and under her chest where she latched onto Karen's dangling tits.
"Definitely not as nice as mine," the blonde taunted. "Maybe later I'll let you worship your new Mistress's boobs!"
Karen felt Jessica's hands fondling her breast, and the thought repulsed her. The brunette was glad when Jessica's hands finally abandoned her tits, but the blonde only moved her hands long enough to lick her fingers before she returned to tweaking and twisting Karen's nipples playfully. Karen tried with all her might to command her nipples to ignore Jessica. But despite her best efforts, she could do nothing to prevent them from stiffening and assuming the position of attention.
"Oooooh!!!! You like this don't you, you dirty little slut? You really must be a wench!" Jessica taunted Karen. "You're not shy are you? I mean you posed naked in that nasty rag. How about showing my fans what my new Plaything looks like."
Jessica released Karen's tits and grabbed hold of the waist band of her thong and with one quick, fluid motion, she slipped the thong down Karen's legs and off over her feet; leaving Karen in nothing but a pair of boots. "You're not looking very Jolly..... Roger!" Jessica teased the Playmate about the hopeless position she found herself in.
As Jessica spun Karen's thong around her head in celebration, Ashlee let up just for a second to see why the crowd was going nuts. Karen felt the pressure on her throat lessen for just a moment and took in a deep breath. With Ashlee distracted by her sister, Karen reached out and grabbed hold of Ashlee's hair with both hands. Before she knew what hit her, Karen fired a head butt aimed at Ashlee. Her aim was perfect as her forehead scored a direct hit with the bridge of Ashlee's nose, breaking it with a sickening CRUNK! Jessica heard the impact of the two women's head and looked over just in time to see her sister flop to the ground with her face a mask of crimson red. Jessica let out a shriek and then got pissed. "You fucking slut! What'dya do to my sister?"
Maybe the head butt was not the best thing for Karen to have done, but it was the only thing. Striking Ashlee head first as hard as she did had an immediate effect on Karen as the effects were cumulative with the trauma her brain suffered when Ashlee rammed her head into the ring post. As Karen lay dazed, Jessica reached down and grabbed both of her ankles. With a sudden yank on her legs, Karen felt herself airborne, flying towards the center of the ring. She was a split second too late getting her arms into a defensive position, and the Playmate crashed down to the canvas directly on her tits, and then face first a moment later.
Jessica never released the Playmate's ankles, giving a quick twist to her body as she rolled Karen over onto her back. Moving in quickly, the raged filled blonde dropped a knee into Karen's belly driving the air from her. Jessica straddled Karen's waist and started wailing away at Karen's breast. "See I try and be nice to you and look what you did to my sister. I'm going to make you pay for that bitch!" Jessica screamed as she continued her never-ending windmill of punching to Karen's treasures until her fist began to hurt. Then Jessica switched tactics, looking to end the fight as she pulled Karen to her knees and wrapped her arms around the Playmate's body; aiming her larger breasts against Karen's badly battered puppies!
With a tight squeeze she started to crush Karen's tits as they were absorbed into her own impressive pair. Karen just moaned in pain and was unable to counter Jessica's assault. Jessica was smart enough to trap her arms at her sides when she locked the bear hug on, and there was nothing that Karen could do. When she felt that she had taken all of the fight out of Karen, Jessica released her hold and gave the Playmate a rough shove backwards, sending her crashing down to the mat, flat on her back.
"Time to end this wench!" Jessica proclaimed as she lowered her large rack directly onto the face of the Playmate.
“Uuummppphhh!!!!" Karen’s muffled grunt escaped from between Jessica's suffocating breasts.
As Jessica looked to snuff out the life of Karen, she glanced over at her sister. Ashlee had been helped back to her seat and was being attended to by the ring side medics. "This bitch is going to pay for that Ash! Don't worry about a thing!"
Karen's mind raced. "I have to do something quick!"
Feeling Jessica shift all her weight forward, trying to force her breast to envelope her face, Karen saw an opening. Karen fired a knee up that impacted solidly with Jessica's womanhood. The blonde gasped in pain as her mouth formed an ‘o’ as she went flying from her perch. Karen struggled to breathe and then quickly rolled over on her hands and knees.
"Shit that was close!" Karen thought as she saw Jessica favoring her groin as she crawled to the corner of the ring on all fours where she grabbed the ropes trying to pull herself back up to her feet. Karen knew it was now or never and broke into a sprint just as Jessica started to rise. The Playmate landed on the songstresses back, grabbed hold of the ropes, and began bouncing up and down in a perfectly executed bronco buster. Jessica groaned in pain until she was driven face first into the mat. Karen quickly slid under the bottom rope to the outside and grabbed hold of one of Jessica's ankles in each hand. With one leg on either side of the ring post, Karen pulled back hard driving Jessica crotch first into the unforgiving steel.
BONK! “AIIIIIIIIEEEEEGGGGGHHHHH!” Jessica shrieked in pain while Karen repeated the move several times. With the tide successfully turned, Karen crawled back under the bottom rope and dragged Jessica back to center ring.
Ashlee had regained enough of her senses to see that Jess was in big trouble. She shoved the medics out of the way and started to scamper her way up to the top rope, in the corner of the ring. Karen had been standing with her back to Ashlee, standing above the downed Jessica contemplating her next move. The Playmate never saw Ashlee and never knew that she was in immanent danger.
Suddenly, Danny Boy yelled, "Look out! Behind you Karen!"
Just in time Karen's head snapped to the jumbo-tron where she saw the image of Ashlee perched and ready to strike. At the last possible instant, Karen stepped aside and Ashlee crashed down on Jessica with no way to stop herself.
"Too bad you don't have air brakes like in the cartoons," Karen snickered as she looked down at the crumpled heap of woman-flesh that had been the Simpson Sisters.
Karen stripped the sisters as the crowd hooted, jeered and savored the sight, then she arranged their bodies '69' with Ashlee on top. Stealing a move from the Rock, Karen ran to the far ring ropes, bounced off and hopped over the Simpson stack, throwing herself against the near ropes which sent her rebounding once more at increasing speed toward the stack of singers. Stopping short, Karen drove her elbow down into the small of Ashlee's back!! Ashlee moaned as her head lifted in an involuntary reaction, then flopped back down.
Karen sat up straddling the two sisters, then began to thrust and pound her hips, grinding back and forth; riding the Simpson Sisters and forcing both sister's noses deep in her siblings slippery slit. When Karen finished her 'Ride of the Valkyries', she kicked Ashlee off of Jessica and leaned over her, brushing the hair back from Jessica's face so she could see her eyes as she slapped the blonde several times until she had regained some resemblance of consciousness. When Jessica opened her eyes, Karen cruelly dropped a knee down across Jessica's large breasts, mashing them flat against her rib cage.
As she maintained the downward pressure, Karen growled, "How was THAT for my best shot?"
Karen took a moment to soak in the cheers of the fight fans after her efforts in a long hard battle. She then slipped between the ring ropes and started heading back to the dressing room.
"Maybe those two will want to play again another day," Karen thought she hobbled back to her dressing room and slumped in front of her locker. Preparing to get in the shower, she slipped out of her last remaining clothing and her boots. Giving the skull and crossbones a gently swipe where a scuff had formed, she decided. "I REALLY do love these boots!"