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Damian's balls swung heavily between his legs as he scrubbed back and forth on all fours. The foxes Master, a racoon called James, had given him a drug 2 months ago that made him totally numb down stairs and prevented all orgasms - a type of cage-free chastity. James had often teased Damian with the antidote to the drug - saying if he completed all his household chores he would get a reward.

So here he was, hand and foot paws in leather mitts and a large ball gag in his mouth, trying to scrub the wooden floor of Master's bedroom. He was making a clumsy job of it, due to the mitts, but it was getting done and he was looking forward to his reward!

"Are you done up there yet pet?" called James as he came up the stairs

"Hummm , phhhmmum! Eeeess!" Damian tried to reply inspire of his gag

"Yeh I'd say your done there" confirmed James as he walked into the room "Is that all your tasks done?"

Damian sat back on his knees, his leather clad paws covered in bubbles and cleaning foam, and nodded happily.

"Good boy!" James chirped happily "Get in the middle of the floor on your hands and knees"

The fox scuttled off to the large soft rug in the middle of the bedroom and assumed the position - his chubby butt presented high in the air. James went over to his toy box and took out an aggressively shaped Aneros prostate milker and a shot glass with a suspiciously peculiar symbol on it.

"Get to work pet" he said as he threw the Aneros down in front of the presenting fox

Damian struggled to pick up the small toy with his mitted paws, but he couldn't even lift it off the ground - never mind get it to his tailhole. James laughed and then walked over and scooped up the toy. He squatted in front of the fox and taunted him with the toy, tapping him on the muzzle.

"You want this bitch, want this in your tail?"

Damian nodded furiously.

"Well ok, but you are going to have to do something for me" said the racoon, unbuckling the fox's gag

"Yes Sir, anything" Damian said after spitting out the ball in his mouth

James reached back over his slave and placed the shot glass underneath him, then he put the toy to Damian's tailhole. It slipped in easily, the fox's rear pulling the toy in until its base struck his perineum. Damian immediately began to move the toy in his ass with his muscles - seeking the hands free milking that was allowed by the drug.

"Ah, ah, ah, wait until I tell you pet" said James as he turned around, his plump coon ass in Damian's face "Now you may start, and you know what to do. Oh if you miss the glass you will be licking it off the rug - and you will be punished!"

The fox did indeed know what to do, nestling his muzzle between his Master's cute cheeks - his tongue flicking out to caress the coon's soft rosebud. James moaned, stretching his arms out like a cat in the morning as the canine's rough tongue dragged across his tender flesh, the soft fur around his tailhole dampening. All the while the familiar rhythmic motions of his rear moved the milker within Damian with the effect of it rubbing his prostate - a gland the drug didn't affect.

As the fox continued to pleasure his Master, the pleasure in his rear built up and up until he felt the first drops of milk emerge from his still flaccid furhood. The sticky, silky white prostate fluid dribbled from his cock and straight into the shot glass. It was not like an orgasm; the pleasure simply came to a maintained head and the milk came in small but repeated bursts - filling the small glass fast.

"Stop" called James "Every time the glass fills you will drink it and then continue pleasuring me, I want to feel your milk on my hole so don't swallow it all - I want a sloppy rimjob!"

With great mental effort Damian stopped the rhythmic movements of his ass and the last strand emerged from his floppy cock - almost causing the glass to over flow. He looked down at his mitted paws in confusion.

"Sir how do I..."

"Shut up! Drink it, get on with it - my ass is getting cold"

Damian blushed at his scalding and tried to pick the glass up with his mitts. He managed it, but spilled some of the fluid on his leather-clad paws. He knocked back the shot - the familiar salty-sweet taste quite a delicacy. It was hard to drink the slime but that just meant that a lot of it remained in his mouth or around his muzzle.

He put his noose back between his Master's rear and his sticky tongue flicked out again - spreading his own milk around the coon's rear-end. As his Master started moaning in ecstasy again, his sensitive flesh under assault from his loving pet, Damian got into his stride moving the toy with his muscles again.

He began to cum milk a second time, filling the glass very quickly and without being told slurping it down (and getting even more of it on his paws). He repeated the process a third time and a forth - each time the pleasure getting more and more intense.

After he had filled and glugged down five glasses James stopped him once again and got to his feet.

"Good boy, but how about a challenge! You fill 5 more glasses without spilling one and you get to cum finally" he waved the antidote and Damian's heart raced "But spill one and you will have to pleasure me again... and you wont get to cum... and then you will be punished... oh and did I say 5? I meant 50!!!"

Damian's heart dropped with his jaw. It was impossible, it had to be, but he needed to cum so bad! Milking was good but it didn't reduce horniness at all - it only raised it. He had to do it.

He hunkered down over the sticky glass again as James sat on the bed and watched the show. His rhythm kicked in again and the pleasure was immediately apparent but he had never done more than 10 milkings in a row and he was surprised he hadn't spilled a glass already.

He approached his first of the 50, his milk shooting into the glass again familiarly. The fox tried to pick the glass up again with his restrained paws, but the leather combined with his shaking prostate orgasm lead to a horrible mistake - the glass falling to the carpet, its contents spilling.

Damian looked up to see the response of his Master, but before he could raise his head the coon over him and pushing down on his neck, forcing his head down into the floor.

"Worthless little shit, can' even drink from a glass - well if you can't act properly, you won't be treated properly. Get on you back NOW!" James said harshly and uncaringly.

Damian did as told with a whimper - physically shaking from the threats of his Master. The coon then slipped a very tight elastic band over the fox's flaccid cock and it snuggled up behind his un-engorged knot. Rapidly the fox's cock swelled as blood was trapped in it by the band - however he felt no feeling, no arousal, nothing. It was like it wasn't his cock, just a shaft of warm meat bobbing between his legs.

"Is that good pet?!?" James teased as he rubbed Damian's numb cock

The coon then got on all fours on the floor and raised his butt high - his tail flopping over his back.

"Pleasure me pet, then you will be punished like the bitch you are."

Damian mounted his Master, a usually privileged experience, but with only his numb shaft between his thighs. He put the tip of his furhood to the racoons waiting tailhole and sharply thrust the head in.

"Give it to me hard pet, give me all you got."

Damian began to fuck the coon roughly and without feeling - after all the only thing he could feel was his crotch slapping into James's butt. James hollered and moaned in pleasure as the fat fox cock pounded in and out of his rear.

"Harder, Faster!"

James responded to his pets thrusts, toughly enjoying his rough yiff, and eventually after pawing himself at the same time he came - his seed spraying the floor and a howl of ecstasy emitting from his mouth. Damian felt no such pleasures.

"Stop now pet, lay on your back." James said standing up "That was good, but you still need to be punished!"

The coon wasted no time in securing the fox's calves against his thighs with leather belts - all four of his paws still mitted in locking leather. A rubber bone was then forced into Damian's mouth and its custom straps tightened. Finally a collar was secured around his neck - a bone shaped tag dangled from it.

"You want to act like a little bitch you will be treated like one! Now get up boy, walkies!" called James smirking and holding a leash

Damian blushed as he struggled to comply.