Chapter 4: Jimmy’s Prison Duty

Jimmy was quite nervous regarding the new prisoner that was being assigned to him to keep an eye on. The original guard had his pregnant wife to take care of so he took a leave so Jimmy being the only free substitute took over his position.

Coming back to the topic, the prisoner had been imprisoned for killing a bunch of men in a casino after losing to them in a bet. She was uncontrollable like a beast and was only captured after a dozen of bouncers overwhelmed her.

As her prison guard Jimmy was also responsible for cleaning her quarters because she was chained just like other prisoners. Jimmy slowly opened the steel door and entered the prison room. A muscled woman with scars on her face was staring right at him from the ground.

Jimmy slowly gulped but he felt as if his gulp was audible to the person as the moment he did a creepy smile appeared on her face.

Jimmy felt fear but the chains on her made him realise that he was worrying for nothing and started doing his job. When he was almost done and was about to go back the woman finally said "Thank you, now it's my turn to repay your kindness."

The chains on her broke off like they were made of clay as the the woman forcefully laid him down and started kissing him furiously her arms quickly entered his pants and started playing with his genital which due to fear was incapable of getting hard for the moment.

Her hands gently teased his genital unlike the furious rampage his lips were dealing on his face. She started by kissing and then shifted to licking his whole face as if he was a delicacy that she was tasting for the first time.

Jimmy's whole face was covered by her saliva seeing which she had a smile as she said "Good. You are now my person property." After saying that she inserted her tongue in Jimmy's mouth and started exploring his mouth while playing with his tongue from time to time.

Finally Jimmy's pleasure overtook his fear and he finally got hard but the moment he did the woman started stroking his dick harder. Jimmy couldn't help but moan in pleasure and taking advantage of it the woman spat in his mouth and slapped him which was followed by again ravaging his mouth with her tongue.

Jimmy gulped the saliva that entered his mouth and as he felt the hot saliva of the woman flowing down his neck he couldn't help but like the sensation.

The woman's light stroking had made Jimmy all wet down there making her hand wet with all his pre-cum. The woman finally stopped and removed her worn out pants. Followed by her stinky panties.

She then slowly lowered her hips as she expanded her asshole with the help of her hands. Jimmy's tip soon touched her asshole making her stop a little bit. 

"I wasn't expecting anal to hurt with just the tip touching my asshole...I can't wait for more....ahhh!" The woman said as forcefully sat on dick. The dick entered fully in her asshole. Jimmy was lost in ecstasy by the feeling of tightness his dick was experiencing.

"Eiiiiii"

The woman hissed out in pain as her asshole skin most probably tore because of her actions. She could only wait for the pain the subside while having Jimmy's dick fully inside her ass.

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The occasion squirming of the woman's muscles made it difficult for Jimmy to control himself as he blasted out his load inside the woman.

The woman still felt her ass burning felt the hot semen from the man on whose dick she was sitting on. The semen covered the inner linings of her asshole and reduced the pain.

Thinking that she was now ready she slowly lifted her ass. The pain was still there but it was quite less compared to earlier thanks to the sticky semen.

Realising this the woman soon started moving her hips up and down like crazy as she let out wild moans.

Ahh ahhh aaaaahhhhh.

She literally didn't gave a fuck about anyone hearing her as she bounced on Jimmy's dick wildly. Jimmy's dick which was out of energy hardened once again ready to be sucked dry by her.

The started stimulating her clits while moving her waist up and down making her moan louder by a decibel. Soon as if she could control herself no longer she orgasmed sprinkling all her fluids on Jimmy who was right beneath her. He was all covered up in her hot sticky fluids. Jimmy couldn't hold back anymore as he also came out again in that tight ass making the woman was still orgasming squirm even more.

After a while when both of them catched their breaths the woman slowly stood up as Jimmy dick fell out of her asshole. The cum inside her ass dropped down on Jimmy's body.

The woman look pleased as she bent down and whispered in Jimmy's ears "I'll be waiting for you tomorrow aswell. Don't be late my toy~" and with that she wore her clothes and went back to the place where she was shackled earlier.

Jimmy soon after exited the cell with his torn clothes on thinking of what cod happen to him tomorrow and whether he should leave his job or not.

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