Stuffing the Foxhole 4

Eggman had decided it was time to break Tails once and for all. Fully and completely, so that the fox would remain nothing more than a fuck toy forever. And the best way to break someone, was to first give them a taste of hope. The doctor peered through the barred window of a cell Tails had been thrown into. "Fox boy... Hey! Look at me!" he shouted. Tails was slumped in the corner, and slowly lifted his head. "Now what, Eggperv..." he growled. Yes, he still had too much spirit for the doctor's liking. But he laughed softly. "I've a deal for you, Tails. I've prepared a gauntlet of old 'friends' for you. If you can manage to defeat one of them, you'll go free. However, I am certain you won't beat a single one. No, instead, you will be broken by the end of the gauntlet, so much so that you'll willingly accept MY dick inside your pitiful vulpine rear!" This did appear like the end of things, but Tails stood up, shooting the doc a defiant glare. "I'll win, Eggman! I'll never...NEVER let the likes of YOU fuck me!" he declared. Eggman chuckled softly. "Well, I hope you're ready to put your money where your mouth is, because the first round starts...now!

The cell door opened, and Nack the Weasel strode in, holding the brim of his hat. "Hey, runt... Long time no see." he said with a smirk. Tails realized he had to best the purple weasel in combat, so he quickly leapt at him, throwing a desperate punch at his head! Nack weaved to the side to avoid the punch, and then grabbed Tails' wrist. "Rude. Not very hero-like to punch first, either." he said, releasing the fox's wrist just before giving him a hard kick to the chest! Tails slammed against the cell wall, and was then struck with another swift kick for good measure, the wind being knocked out of him! Taking advantage of Tails' stunned state, Nack grabbed him into a headlock and gave Tails several punches to the gut! "Agghh!! Owww!!" Tails cried as Nack laughed. "Not so tough when there's no room to zip around, eh?" he grinned. However, Tails suddenly surprised him by wrapping his two tails around his shoulders, and then performing a flip that slammed the weasel to the ground with a hard thud! The battered fox turned slowly, and tried to hold Nack down with his foot. "I...win!" Tails huffed. Nack smirked under him. "Silly fox... You can't win!" he said, easily pushing Tails' foot off him and causing the fox to stumble backward! Nack was on his feet quickly, and giving Tails a hard roundhouse kick, he knocked the fox onto his back! Then, he sat himself on top of Tails' stomach, and removed his belt, wrapping his around Tails' neck. "Ohh, do I wanna squeeze the life out of ya... But what the doc told me'll have to do..." Tails gagged, and Nack removed the belt, tossing it aside. Tails' eyes glanced downward, and saw Nack's dick growing hard! "You lose, fox boy..." he sneered. Tails bit his lip nervously. He knew it was true; he'd lost.

The room, of course, had a camera watching and recording all the action. So, Nack lifted Tails into his arms while resting his back against the wall, both of them facing the camera. He hoisted Tails up from behind by the thighs, and held his ass over his dick. "There's a contest among us, twerp. Whoever breaks ya gets to have ya fer a week, all to themselves. Oh, the things I'll do to you...!" Nack said with confidence. Tails let out a desperate cry and Nack's dick impaled him, and the villain started to pound his length up into him while holding the fox for the camera! Eggman had been lacing Tails' food with a substance that'd keep his ass tight, so every first penetration was rough and painful for the fox. He grit his teeth, and tried not to show too much fear as his body was bounced on the weasel's cock. If he let Nack break him, the weasel might kill him just for kicks during his week. And Nack was giving it his all, grunting with effort as he slammed his shaft up into Tails' tight ass! "Sh-shit, thought ya'd be loose after takin' it from all yer f-friends!" he huffed, maintaining his grip on Tails' thighs, lifting him up and down. Tails' own cock had gotten hard, and was swinging along with his balls as he rode Nack's pole, his tails hanging limply under him while his head tilted back, sharp exhales escaping his clenched teeth now and then. Nack growled, pulling that ass down to his hilt! "C'mon, ya punk! Snap! B-beg fer my seed!" he shouted. But Tails never did. He did, however, start to moan as that cock's deep thrusts started to fill his body with that dirty pleasure. Yet his expression remained mostly defiant, and as Nack cried out, pumping that foxhole with its first filling of the day, Tails gave the camera a smirk. "C-couldn't...break me!" he huffed. Nack won the battle, but not the war.

The door opened to switch Tails' opponents. "I hope you didn't think you'd get a rest between rounds..." Eggman snickered, "Oh, Tails, you WILL be taking my dick by the end of the day...and you'll do it willingly!" the doctor laughed as the next opponent, Chaos, stepped into the room! Seeing that Chaos was next, Tails started to realize just how screwed he was. He threw a weak punch at the creature, but his fist simply stuck in its watery body. Tendrils suddenly burst from Chaos' back, scooping Tails up and swinging him around the room, slamming him against the walls as he screamed and yowled in pain! He didn't even have a chance, Tails had lost this round, too. Once Chaos had slammed the fight out of him, those tendrils began to play with his body, snaking all over him. One tendril coiled around the fox's dick, stroking it back to life. Two tendrils pushed into Tails' ass, stretching his hole open! "N-noooo!! Aah-aaahh!!" the fox cried, only to have his mouth stuffed by a wet tendril. He gurlgled a bit with the watery appendage in his maw, weakly struggling as his ass was stretched and his body abused. Chaos' tendrils snaked over his ass, rubbed into his chest fur to tease his nipples, and gave his balls a soft little slap, causing them to jiggle a bit. Through it all, Tails maintained his fighting spirit, even if his flesh was weak at this point. He weakly tugged his arms and kicked his legs in the tendrils' grip, knowing that he was Chaos' to use anyway. The creature finally tired of playing with him like this, and lowered Tails toward the ground. The fox looked at his adversary, and gasped to see that a watery cock had formed at Chaos' crotch. Even Chaos had designs on fucking and filling the fox's hole!

The tendrils didn't release Tails, they secured their grip around his arms and waist as they drew the fox closer to Chaos...and his cock. Tails tried to move his legs, to kick them or brace them on the ground, anything to resist, but he felt too weak from his beatings to do much...and then, Chaos' hands grabbed his legs firmly, hoisting them up as his ass hovered over that wet dick. The fox looked into his assailant's eyes, and saw only a monster, incapable of being reasoned with. He gave up squirming, hoping to save energy for the next battle. Thus, in a brutal motion, Chaos plunged his cock upwards into Tails' rear, causing him to cry out, a bit in surprise at how solid the watery shaft could manage to feel! The liquid of Chaos' body seemed to bubble a little in excitement as the beast began slamming that dick up into Tails' hole, his wet length sloshing as it conformed to his insides, while also driving deep, deep inside him! Tails could feel the aquatic appendage alternate between a mostly-watery state and a throbbing, solid state, almost starting to act like a vibrator inside him. "Oh, f-fuuuck! W-waaaaugh!!" he wailed, straining to hold on to his sanity through the rough pounding his ass was receiving. If this hadn't been part of a challenge, to avoid breaking and hopefully gain his freedom, Tails would likely be moaning like a slut now, not bothering to resist acting the part of the beast's fuck-toy. It didn't matter to Chaos, his liquid body churned excitedly as he held that fox over him and thrusted up inside him. Before long, the creature's lustful excitement came to a boil, and Tails yelped and moaned to feel a hot liquid seem to pump out of the different liquid of Chaos' cock! This was two rounds down... Tails had no idea how long this gauntlet would last.

The next foe to enter the cell was Mephiles the Dark. How Eggman managed to bring that villain back, Tails had no idea, but now he had to try to defeat him. Mephiles stood glaring at the fox. "Well, take your best shot. Just know that the moment you bore me, I will finish this." he warned. Tails was unsure of the best way to attack, but he couldn't waste time thinking about it. He leapt up, spinning to strike the villain in the head with his tails! He'd used all the strength he could muster...and it didn't do anything. Mephiles didn't even flinch. "And now I'm bored." the Dark sighed, raising his hands as he glowed with a purple energy. Tails looked at him, unsure what he was doing but certain it wasn't good. He tried to charge at Mephiles to throw a punch his way, but as he wound back his fist, a hand grabbed his wrist! "H-hey!" he yelped, "T-teaming up is cheating!" Mephiles simply laughed at him. "Fool, I work alone..." he said, and Tails looked to see who'd grabbed him, gasping to see a second Mephiles. "The wonders of time travel..." the Dark sneered. His second self held both Tails' arms, keeping him in place as the first Mephiles slammed his fist into the fox's gut! The wind was knocked out of Tails, but the pain didn't stop as Mephiles struck his chest, and then his jaw! Then, he was thrown to the floor, and both Darks pointed their hands, firing balls of purple energy at the fox on the ground, making him scream in pain as the energy overwhelmed him! Mephiles then hoisted Tails up by the throat, and pinned him against the wall. "Strange. I still see the slightest glimmer of bravado in your eyes..." Mephiles stated, "Let's see if we can't cure you of that... And when I break you, no time limit will save you... I will crush you over the course of eons!"

Tails was placed on his hands and knees, and looked up to see one Mephiles in front of him, plopping his dick against the fox's face. He also felt the cock of the second Mephiles rest between his ass cheeks, and he gulped, unsure if he still had the willpower to make it through a double-fucking. The Shadow-looking Dark certainly seemed confident as he ground his length into Tails' face. "I would ensure your breaking by putting both these cocks in your tighter hole... But I don't want to break your body, yet, only your mind!" he said, grabbing Tails' head and forcing his shaft into the fox boy's mouth! Then, the other cock slammed right between the tails and into his ass, making him whine in a muffled voice over the dick in his mouth! Mephiles' clawed hands clutched his waist and head as he started to thrust into Tails from either side, his diamond-hard shafts roughly boring a tunnel into his anal depths, and diving into his gagging throat as well! The fox's tails hung limp as he took these thrusts, much of his previous defiance having been beaten out of him at this point. He did raise his hands to push back against the Mephiles in front of him, if only out of desperation to breathe. Mephiles slapped his cheek on both ends, laughing at the fox's futile struggle! "You have already lost... It matters not if I break you in the next few moments. You will break soon... It is only a matter of time." the Dark taunted, pressing his dicks to the hilt as a muffled scream came from Tails! He realized at this point it was true. He might hold out this round, but he would almost surely break the next round, he no longer had the strength to win this wager. No, he never had a chance, he felt that was clear as he tasted the gross seed of the Dark, flooding his body from either side.

"I must say, you've lasted longer than expected..." Eggman stated as Mephiles exited the room, "But the deal was for you to defeat an opponent. And now we've come to the end, the final fight. After this...you are mine!" he sneered. Tails stood shakily, watching the door. He was nervous. He didn't want Eggman to fuck him, but at this point, he had to mentally prepare for it to happen. The final opponent stepped into the room, the masked villain known as Infinite the Jackal! "Don't bother attempting to battle me... You've already lost!" he declared, his Phantom Ruby glowing as energy burst from it and immediately struck Tails! The fox felt quite strange, but not in pain. He looked himself over, and gave a sudden gasp! The Phantom Ruby's power had changed his reality, transforming Tails into a gorgeous vixen, with a sleek hourglass figure and big, round breasts! The shock paralyzed Tails as she screamed, holding her mouth as she noticed her more feminine voice! Infinite stepped close to her, grabbing her boobs in his clawed hands. "Instant victory, as expected. Now I will finish softening you up for the doctor...and then we have a week to see if I can't impregnate you..." he said, giving her breasts a squeeze as his eyes glared lustfully at her through his mask. "Aghh... Y-you can't impregnate me... Your power is just an illusion..." Tails stammered, glancing down and gasping to see the size of the jackal's arousal. It seemed the Phantom Ruby had worked some magic on his dick as well. It was massive, the biggest the fox had yet encountered. Infinite took a moment to remove his mask, smirking at Tails. "Virtual reality is still a form of reality. I promise you, this will feel VERY real..." he said darkly.

Tails was very soon pinned to the ground, her frightened eyes looking up at Infinite as he lined up his giant shaft with her new pussy. As the jackal returned her gaze with a confident sneer, Tails knew she was about to be broken. She shut her eyes and let out a resigned sigh. "Bring it on..." she said softly. With a soft chuckle, Infinite clutched her hips, and slammed his mighty shaft into her pussy! Tails' eyes shot open and she cried out, her feminine scream filling the room! A brief glance down confirmed how she felt. There was a long bulge in her belly, in the shape of his huge cock. Infinite gave a light cackle, and began to roughly fuck her with his massive dick! He grunted, counting his thrusts briefly. "...two...three...four!" At the fourth deep penetration, Tails arched her body and wailed submissively! "F-fuuuuck!! Aghhh, g-go, break me, wreck me, aaahhh!" she cried, and Infinite gave a victorious laugh. "I have broken you, with a mere four thrusts!" he cackled. Tails took hold of his hands, and guided them to grope and squeeze her breasts. "Y-yeah, y-you big alpha dog, uhhnn!" she huffed, feeling his girth batter her body and hammer at her womb, "Y-you did it, haaahh, you destroyed Tails, he's dead now... I-I am...your slut now!" the vixen moaned, gasping lustfully as the jackal grasped her breasts tight in his claws. "Yes, good slut... You know your place now..." he huffed, forcefully kissing her as he slammed his huge cock deeper inside her! She purred into the kiss, her face reddening at the thought of take more and more cocks forever! Finally, Infinite sealed her fate, his cum flooding and stuffing her full, her belly swelling with seed! However, the Phantom Ruby suddenly flashed, and reality took over. The jackal's average-sized dick was stuffed deep in Tails' ass, cum leaking from his hole. But the broken, slutty look on Tails' face remained. He was at last, fully defeated.

Infinite left the fox on the floor, assured that he'd be spending a week with Tails soon. It was at this point that Dr. Eggman stepped into the cell, giving a diabolical laugh as he looked down at the defeated fox, pleased with himself. "At last, no one is left to oppose me. Look at you, you were so proud, so confident! Now, Tails... I will ensure there isn't a bit of heroic thought left in your mind. Beg me to do it...now." he sneered. Tails panted, exhausted from all the fucking, and looked up at the doctor nervously. "D-do it... Please, please... Finish me..." he said.

It was a bit of a blur for Tails, moving from the floor to where he was now. The doctor was seated in a sturdy chair, the zipper to his pants open, and his thick cock...impaling Tails' foxhole. The doctor's hands were guiding him, but at this point, Tails was riding that cock pretty much on his own. "No, ahh... N-nooo...!" he whimpered, looking into Eggman's wicked face and realizing that he had truly and completely won. The doctor gripped Tails' waist tighter, and started to move him more forcefully up and down his cock. "Nooooooo!! Ahh, nuhhgh... Aaaaaaaaahhh!!" Tails cried, sounding as desperate and defeated as he could. The doctor laughed. "Good, good... Keep wailing, just as I asked you..." he sneered. Even his cries of protest were Eggman's choice. It was over, any thoughts of escape and saving the world were distant fever dreams now. From now on, Tails would obediently act as the Eggman Empire's sex toy. There was no other future for him...

The....End...?