It was just another contest, but Lynn really wanted to win this one. Her favorite pub, The Rusty Nailed, had a different contest every Monday night along with “Ladies Night”, where all the ladies drinks are $1. She never missed a Monday there.

She had entered several contests within the last year including a wet tee shirt contest, a slut writing contest, a beer chugging contest, a topless Hula Hoop contest, a pepper eating contest, a homemade bikini contest, and a Twerking contest. She fared ok with the beer and the peppers, but she always seemed to come up short on the others. It was usually because some bimbo with bigger boobs or a plumper ass would show up. Lynn had a pretty nice rack, as far as titties were concerned, she’d been complimented plenty of times by men and women. Her ass always drew whistles at the beach, so she just chalked it up to bad luck.

Tonight, she was entering the “Floppy Titty” contest. Sizing up the competition, Lynn felt like she had a pretty good chance of at least making it to the finals. She was up against twelve hot ladies, but only four others had a set of tits that were equal to or better than hers. Most of them were pretty drunk already, so when two of the four were eliminated because they threw up on the judges, she felt like her odds increased exponentially.

The premise of the contest was that the contestants had to remain in place, always touching the floor with some part of both feet, and shake their tits while the music played. They each got thirty seconds before the next contestant took their turn. The music they used was house trap 120 bpm, so it went by pretty fast. Some of the contestants had zero rhythm, so they had to use other forms of sultry and sexy moves to try and win the crowd over.

That was what Lynn loved about The Rusty Nailed. Their judges had rules and they never bent the rules, no matter what. She saw a girl get completely naked one night in a wet tee shirt contest. She was clearly the winner, she didn’t need to get naked, but she did. The winner got $1000 and up until the moment she got naked, the money was hers. The judges disqualified her! They even tried to warn her three times before she did it, but because she violated the rules, she lost.

Lynn loved the rule system, no matter what platform, place, situation, or setting, she was a stickler for rules. If she knew the rules, she always respected whatever they applied to. The rules gave everyone a chance. She liked taking chances, as long as there were rules.

She had exactly three Margaritas before she stepped foot on the stage. The bartender was stingy with the tequila, so she knew she needed three to knock off the edge and free her up to enjoy the stage without making a fool of herself. When it came her turn, she did not disappoint. She stood her ground and made her all natural titties dance like nobody else on the stage. She slipped her pink tube top down below her tits and bounced them until the judges were literally sitting with their mouths open. She had practiced in front of her mirror for the entire week and even recorded herself and watched it to make sure she was undeniably hot and sexy.

The finals were literally just a formality, albeit painful. It was between Lynn and the other two, just as she had suspected. The finals required the three contestants to compete with the same rule, but this time a wooden hanger with spring loaded clamps would be attached to their nipples and the first contestant who shook the hanger off would win. The judges even had a video camera set up in case there was a tie for instant replay! The Rusty Nailed was serious about their contests and integrity.

The first contestant bowed out gracefully and forfeited her place, knowing that the pain would be far too much for her poor nipples to take. They placed the hangers on Lynn and the second contestant and started the music. They both began bouncing and whipping their torsos from side to side attempting to fling the hangers off their nipples. Exactly one minute in, the other girl stopped, with tears streaming down her face. She physically removed the hanger using her hands. She couldn’t take the pain, so she essentially forfeited as well. Lynn was declared the winner by forfeit, but Lynn was not in it to win by forfeit. She demanded that they keep playing the music until she jumped in place and shook, and bounced so hard on the heels of her feet that the left side finally gave way and she was able to shake them both free. She was a sweaty, worn out, aching mess when she finished. The crowd went crazy and all three judges gave her a standing ovation, a first for The Rusty Nailed.

“This is the hardest $1000 I’ve ever made!” she said as she took her bow and the cash. Again the crowd went wild with applause and whistling and cat calling.

They escorted her backstage to where her clothes were and allowed her to change. She was in the middle of getting dressed when there was a knock at the door.

“Just a minute, I’m getting dressed in here,” she said, trying to hurry.

“Another thousand if you let me in right now,” came the female voice on the other side of the door.

Lynn quickly opened the door, standing in nothing but her panties. The woman was a tall blonde dressed in high heels, fishnet stockings, a black micro-dress, a black bra with cutouts for her big boobs to enjoy freely bouncing about, with a white short midriff leather jacket tied at the top. Her makeup was immaculate with bright red lipstick, perfect eyebrows and eyeliner, big eyelashes, and large framed glasses with big lenses, obviously fake. Her hair was long and parted in the middle with a red rose on the side of her head. She held a white vape pen cupped in her hand and there was a large man standing behind her dressed as a chauffeur, or at least Lynn thought he could be a chauffeur.

“You are Lynn, is that correct? The owner said I could find you here,” she said as she took a hit from the pen.

“Yes, and I believe there was mention of a thousand dollars for me if I opened the door immediately? As you can see, I did,” Lynn answered, not wasting any time with chit chat.

The chauffeur handed the woman a wad of cash and she handed it to Lynn who counted out the twenty bills, all fifties. She looked closely at one.

“They’re all real, and there’s a lot more where that came from. I represent an important gentleman who would like to possibly retain your services, if you are open to certain acts that are, let’s just say, lewd in nature? Possibly hinging on the extremely lewd end of things, actually. He pays extremely well for the right individual to perform certain, shall we say, interesting duties of the sexual nature. Does that sound like something you might be interested in?” the woman asked.

“I don’t think so, but thanks for the offer. I’m doing ok in both departments, thank you,” Lynn explained, with just a bit of haughtiness in her tone.

“Would $100,000 for a month change your mind?” the woman asked.

“Well, no. I really don’t think this is something I’m interested in, seriously,” Lynn said with a fair amount of hesitation this time.

“How about $500,000? Would that be something you’d be interested in? Think how many bills you could pay off. You could pay cash for a house if you wanted. Get whatever car you’ve dreamed of. Seriously, you should give it some thought. How about this, here’s my card. Think about it overnight. If I don’t hear from you by 10:00 am tomorrow, we’ll just forget the whole thing ever happened. Plus, you keep the extra $1000 for letting James see you naked, ok?”

That wasn’t part of the rules, Lynn quickly recalled. The rule was to open the door quickly and she gives me the money. Still, it was a lot of money to open the door. She looked at the woman and then at the chauffeur, then took off her panties.

“What are you doing?” the woman asked? “Why are you stripping?”

“I know it wasn’t part of the rules, but for $1000, I feel like I could bend this one rule,” Lynn said, smiling at the chauffeur.

“Another $2000 if you let him take you right here, right now, while I watch,” the woman said quickly.

“Make it $3000 and you can video it if you want,” Lynn said, thinking she’d made quite a deal for herself. She’d just worked her ass off bouncing around and torturing her poor tits for $1000. However, watching the crowd get all worked up over her bouncing and sweating had gotten her wet. She wasn’t looking forward to going home to her Hitachi wand and the big black dildo mounted in the shower. She needed to be manhandled and fucked proper. Those were her rules tonight. Besides, if he lasted five minutes that would be enough for her. She was quite ready.

The chauffeur quickly stepped inside and began undressing as the woman closed the door and took out her phone.

“On the floor. All fours,” the chauffeur insisted.

Lynn quickly assumed the position as her reddened tits swung below and her drenched pussy glistened from his vantage point. The woman started the video, trying to capture the moment with Lynn, now posed and ready to be taken from behind.

Lynn looked up and gasped. The guy was huge. Probably only 9” long, but thick as a soda can.

“I’m not sure my pussy is wet enough for that,” Lynn said with a slight tremor in her voice.

The man mounted her from behind as Lynn closed her eyes and prepared to be annihilated by the massive dick.

“It’s not going in your pussy, dear,” the woman smirked.

The chauffeur immediately pressed his cock against Lynn’s ass, grabbed her hair, pulled her head back, and rammed his thick cock directly into her ass.

She momentarily blacked out from the pain and brute force the man used to overcome her tightly puckered ass. Her arms went limp and her head hit the floor with a thud. The man grabbed her hips and continued plowing into Lynn’s ass as she came and went out of consciousness. She had never felt so violated and used as he pounded away at her defenseless rear-end. She had also never felt so alive.

Evidently, while she was out at some point, the man flipped her onto her back. She awoke with her ankles next to her ears and the massive cock was banging her pussy with extreme prejudice at a rate that she couldn’t keep up with. She was quickly cumming in a wave of orgasms that took her out of her mind with ecstasy as her eyes rolled back.

“I think she likes that,” Lynn heard the woman say as she attempted to open one eye. The woman was licking her lips and holding the phone as she smiled at Lynn’s predicament.

“Now take her to the wall, James,” the woman ordered.

The man stood and reached down and grabbed Lynn under her arms. He simply lifted her up, like a rag doll, and dropped her onto his cock. Her pussy was completely filled and gaping, but she could feel the muscles in his cock as he walked over to the wall, still stuffed inside of her.

He pinned her to the wall and began pounding her, like some kind of mechanical robot bent on fucking her to death. Again, her eyes rolled back as another wave of orgasms washed over her. Her face went pale and she passed out cold. The man continued fucking her until she came to once again. This time she got her bearings, wrapped her legs around his back and began fucking the man back. She caught his rhythm and matched it as she forced herself to grip his thick dick with her inner muscles. She was determined to hang on and outlast this maniacal creature of brutality.

“Nicely done, Ms. Lynn. Of course, you’ll never get him to cum. You might as well quit if you’ve had your needs filled,” the woman said as Lynn continued to fuck the chauffeur harder and harder. “I’ve let him fuck me for two hours straight and he never came. Even after I tried sucking him off, which left my jaws hurting for two days after I completely underestimated that little mistake. I tried using every toy I had at my disposal to get him off. Somehow, he finished me off and walked away without so much as one drip of pre-cum.”

Lynn suddenly lost her focus as she looked at the woman. Something told her she wasn’t lying.

Lynn returned her focus back to the matter at hand and attempted to use everything she knew to get this guy to cum. She licked his ear, she whispered “fuck me harder”, which he somehow was able to do, she pinched his nipples, she even tried tickling him. Nothing changed about the man’s continuous and constant pounding of her pussy. She was beginning to run out of things to try and her poor pussy was paying the price.

“Flip her,” the woman instructed.

Immediately, the man flipped Lynn around into a standing sixty nine. His tongue began licking her cunt like it was the last meal before his execution. She tried sucking the massive cock, but she wasn’t even able to fit the large mushroom head past her teeth. Her face looked freakish as she strained to open her lips even one more hair. Her mouth was stretched to the hilt, and she still couldn’t get past his cockhead.

“Honey, you might as well give up on that, before you hurt yourself. If he decides to fuck your mouth, well, you saw what he did to your ass. Best just to let him lick your pussy until you’ve had all you can stand and I’ll tell him to stop. Or, I can tell him to go back to fucking your ass and I’ll come back tomorrow to check on you. Your choice,” the woman said, smiling.

Lynn allowed the man to bring her to orgasm one more time before calling it quits.

“You may stop, James,” the woman said rather nonchalantly as she turned off the camera app.

The man gently turned Lynn right side up and sat her on the chair by the dresser. He quickly dressed and stood at the door waiting.

“Do you still want to think about it? He’s always ready and waiting,” she said, nodding toward the chauffeur.

“I don’t need to think about anything. It’s one month of doing this for $500,000? I’d be an idiot not to,” Lynn said scoffing.

“Well, I never said it would be just this. What I said was, if you would be open to–”

Lynn cut her off. “I know what you said. I still don’t need to think about it. Where do I sign?” Lynn asked, ready and willing.