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Old 15-May-18, 23:27
Stone Stone is offline
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Default Sharon's Side Job

[This was a custom story, if you have a request for one please leave me a private message].

Sharon's Side Job
By Stone

During the hours of ten in the morning to five in the evening, Sharon Jones is a wonderfully sweet woman. At forty years old, 5'7" 155 pounds, she's immaculately dressed in a fashionable white silk blouse under a dark wool blazer and tan skirt while working as an office manager. But as soon as the work day ends she gets on the freeway and heads to a seedy part of town; specifically a run down old dance studio where she fights other men for money. Al, the guy who runs the low rent studio, is already set up; he finds the men who are willing to fight an older woman in a no rules contest as well as recording the match to sell online.

"What little punk ass you got for me tonight, Al," Sharon says after entering the studio. She begins to undress, removing her shirt and blazer to hang them both up on the hanger provided near the entry; the room is brightly lit with dingy hardwood floors, a line of grey gym mats going from end to end with a mirror wall facing the cameras that are setup to capture the action. Sharon's opponent, Carl, is already waiting; standing at 5'6" 145 pounds in a pair of blue speedos he looks like a scrawny hipster to Sharon with his short goatee and patch work of tattoos. Even though she's only an inch taller and ten pounds heavier she practically towers over the diminuitive man as the two meet in the center; Sharon stripped down to her leopard print bra and panties after having folded her business skirt and left it over the hanger. The rules for the match were flimsy, it was implied that only slapping to the face was allowed but the match would only end when one fighter decided it was over, typically that was Sharon as she enjoyed dominating her opponents until they were begging her to stop.

"How old is this bitch," Carl smirked as he eyed up Sharon. "I thought you were going to give me a challenge, this fat whore isn't as strong as me."

"Where'd you find this little shit stain," the brunette said, marching up to look down at Carl; her hands on her broad hips. He tried to appear tough, standing with his skinny arms folded, he had a couple of piercings with his short dark hair gelled up to give him that bedhead look.

"You think you can beat me you piece of crap," Sharon asked, shoving the twenty two year old boy. He stumbled back, catching himself before he tripped on the mat as Sharon progressed, shoving him again before giving him a hard slap across the face which echoed in the small room. He started to swing at Sharon but she caught Carl with a knee to his balls, dropping him to the mat.

"Where's the big tough guy that thought he could beat up an old woman," Sharon said in a mocking voice as sat her plump ass down on Carl's face. The younger man was still weakened by the low blow and couldn't offer much defense as the heavier woman rode his face. "Since you're such a pussy I thought you'd like to be near one," Sharon laughed as she ground her pantied crotch against his face.

Carl finally started to get his energy back when she pulled the twenty year old up by his gelled hair. "C'mon tough guy show me what a man you are," she growled and punched him in the nuts; his legs completely giving out. Sharon fell back, trapping Carl's head between her legs, as the older woman squeezed him mercilessly; he tried slapping the mat but the brunette just smiled.

"You can't quit that easy bitch," she yelled, crossing her ankles to squeeze Carl so hard his face started turning red. She released the headscissors only to pull Carl by the hair into a side headlock so he could face the camera.

"You gonna tell everyone at home what a little pussy you are," she asked, grinding his face against her 32B cup breast encased in the leopard print bra. She held Carl's head with one arm while her left reached back and grabbed his nuts through his speedo; digging her claws into his sack as he squealed like a little girl.

"Tell everybody," she hollered, twisting her wrist to make him sob even louder, "tell them what a pathetic little wimp you are."

"Go fuck yourself, bitch," he groveled, trying to pry her hand off his family jewels.

She let go of Carl completely; he rolled into a fetal position while Sharon planted her heavy ass on his face again. Carl grunted as Sharon squashed him under her weight; the skinny young man tried to buck her off but Sharon caught his thigh when Carl went to kick up and grabbed ahold of his nuts while squeezing and twisting them.

"Do you hear a little girl down there," she asked towards the camera as Carl's high pitched squeals could be heard despite her plentiful cheeks covering his mouth. After she let go of his nuts, Sharon started gyrating her hips, using his face to get herself off while also bouncing her bubble butt on his head.

"Sounds like you're constipated little boy, are you trying to push out a poo poo," the brunette said in a baby voice, mocking Carl's repeated grunts as he tried to lift her weight off by pushing her butt. Sharon switched to a rear headscissors; grabbing a handful of Carl's hair to pull him mouth tight against her backdoor while she peppered his red face with slaps. The older woman asked if he was a wimp; Carl was facing the camera as he grit his teeth to try and withstand the pain.

"C'mon bitch, let me hear you tell me what a tough man you are," Sharon said as she reached back and slapped Carl hard enough so the blows echoed like gunshots. He tried rolling over to escape the headscissors but Sharon just laughed as he was barley able to budge her. "Is that all you got pussy," she laughed and started using his balls like a punching bag. Carl screamed and tried closing his legs only for Sharon to reach under his thigh and squeeze his scrotum in her sharp nails.

Carl started to panic and Sharon lost her grip on the scissors, allowing the small man to escape. The older woman was able to get up first and punished Carl with a kick of her manicured foot to the ribs. He rolled over as Sharon followed him, kicking and stomping the puny man across the room, until he was trapped against the mirror wall. She dropped her calf down, choking Carl as he slapped at her meaty leg, while Sharon turned his head so he could see himself in the reflection.

"Look at it, who is that," she asked, each question ending with a slap to his face. She held Carl in place with a handful of his hair while he gagged as her weight pressed across his throat. "Is that supposed to be a man? Looks like a wimpy little faggot to me. Well? I thought you were this tough guy, where's this macho man at, all I see is a limp dicked sissy," she continued berating him and slapped at his face with her left hand while keeping a firm grip of his hair with her right. When Carl would cover up she'd hammer a punch into his stomach, causing him to make wretching sounds. She finally got up, pulling Carl by his hair as he struggled to catch his breath, and fell back onto the mat; squeezing his head between her robust thighs.

Sharon enjoyed the muffled sounds of Carl's grunts as his mouth was pressed against her leopard panties; he tried to pull her thighs apart but the brunette grabbed his wrists and held his arms apart like he was being crucified as she crushed his melon. "Let's see you get out of this you little turd," she hollered and crossed her ankles, making Carl scream into her crotch as his face turned bright red. When he did try to extricate himself, trying to stand up but with his head bent over as he was caught in the headscissors, Sharon released her opponent's hand so she could reach out and grab ahold of his nuts. Carl started spasming like he was being electrocuted, trying to jerk his body out of reach despite the older woman having a firm hold of his grapes; crushing them mercilessly in her fist.

It had looked like Sharon might've made Carl pass out from either the headscissors or his tiny testicles being popped as she let him drop to the mat as he sobbed openly like a woman. She got up and sat on his face, pulling his nose into the crack of her ass, as Sharon asked where the big tough man was that was going to kick her ass. The brunette continued her abuse to her opponent's nether regions, punching him not only in the balls but clawing his prick with her nails. She also began pounding his stomach with rights and lefts until Carl was just a whimpering piece of meat.

"How's my ass taste, little man," she asked, grabbing Carl by the hair and pulling him deep into her rear until his head was almost obscured between her plump cheeks. "Oh ya sissy boy, at least you're good for something," she hissed and started grinding her clit against his chin and lower lip while using his nose to stimulate her rectal cavity. The heavyset woman moaned as she bounced on the younger man's face; Carl lay there with his arms at his side, if he ever tried to push Sharon off she'd punish him with a fist to the nuts or another round of belly punching that already left his stomach covered in bruises. After finally getting herself off she got up, dragging Carl by the hair--his face soaked with not only his own sweat but from Sharon's ass as well--and left him lying face down in front of the mirror wall.

She sat her full weight down on his back then pulled his his head up by his hair before locking her thick legs together around his head.

"Look at what a pussy you are," Sharon said while Carl groaned from the headscissors. "You said I wouldn't be a challenge, well was I bitch," Sharon asked, reaching back to pull Carl's speedos up his ass hard enough to make the boy squeal like a pig. "Look at that mirror what do you see," she yanked his speedos up higher until Carl finally said he saw a bitch.

"Not just a bitch what kind of man are you," she was yelling at him now; abandoning her wedgie to reach back and grab his nuts.

"Oh god I'm a pussy please stop! I'm weak, you're strong, please make her stop," he was openly weeping, afraid of how much more destruction this woman was going to do to his poor gonads.

"Don't ever show your pathetic pussy face here again or I'll make you my permanent ass-licker, understood?"

Sharon didn't wait for a reply, she switched to a figure four headscissors, using her own calf to once again choke the younger man out. He tried prying it off but one more squeeze to his testicles had Carl's eyes bugging out as he tried to scream but couldn't make any sounds other than strangled gasps. He finally passed out facing the mirror as Sharon told him to take one last look at what a pathetic loser he was. After he was completely out, Sharon waited to make sure he wasn't playing possum, the older woman got up and took one last ride of Carl's face; screaming as she made herself squirt from riding his nose hard enough to bloody it. She gave the boy one last parting kick to the nuts before collecting her money from Al. The boy was still unconscious by the time she had gotten dressed and told her benefactor to find her a tougher piece of meat to break next time.

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