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Shadow Sanction

Written by Nimrax. Characters by Lilith Games. Art by Zetaxen.

Freddy, the unruly, botched another Shadow Decree's mission which was the last straw for their fearsome commander, Sander, and with the help of his loyalist, Djoser, they enacted a punishment suitable for the mad wolf.

Disclaimer: This story contains some heavy kink themes such as bondage and torture--a friendly reminder to mind the tags and read at your own risk.

"Wake up, pup!" Familiar with how stubborn the wolf was, Djoser added a slap to Freddy's face in order to really get through to him. It was actually more of a light pat, not enough to cause smarting pain but annoying enough to wake anyone up. Furious at the interruption, Freddy exclaimed loudly in response. Until he realized where he was.

"GARH!! What gives?! I was-" The wolf's fury towards the Djoser quickly dissipated when confusion hit him when Freddy realized he was already in an upright position inside a dim room. The mossy and ominous atmosphere suggested that it was the Shadow Decree's private dungeon. That theory was strengthened when Freddy realized he was hanging on with his wrists bound in leather cuffs and forced overhead by chains to the ceiling.

"Wh- What is this?!" And when he tried to fix his position to stand with his legs, he was hobbled by a spreader bar connected to his ankles, with the middle of the rod anchored to the floor. In addition, he also noted how exposed he was with just a jockstrap as his piece of clothing, presenting his musculature to the whole room. Even his tail was forced upward, leaving his butt vulnerable without protection.

"Did you tie me up?" Freddy felt his anger boiling up again, especially when he was ignored. "HEY! I'm talking to you old man!" Djoser finally responded, but not verbally. Freddy tensed when the bull walked straight to him, bracing for what the bovine warrior was about to do. But when he stopped, Djoser did nothing but stare thoughtfully.

"Wh- What are you looking at?!" The wolf was worried when the bull's gaze was boring into Freddy's displayed body, trying very hard to dispel any unwanted horny thoughts.

Freddy was a proud exhibitionist. It was fairly easy to get riled up when someone else was watching one of his debauchery episodes. And this time it was no different when Freddy noticed the bull's eye gracing not just his face, but his whole trussed-up chiseled body. From his tensed pecs to his stretched thighs. The wolf felt the typical warmth centered at his groin and dreaded getting a boner in front of his senior colleague/captor.

Luckily enough, he was saved from an awkward situation when Djoser held his chin to push it sideways. The bull was staring at the lupine's neck, specifically the snug collar that Freddy had just taken notice of its presence. Djoser was not staring at Freddy per se but more checking the security of the bondage.

"LET GO OF ME!" Freddy snarled aggressively, breaking free of the bull's grip to face Djoser with his fangs. The bull was unfazed, well aware that he was just out of reach, thanks to the limiting restraint Freddy was subjected to. Infamous for his stubbornness, Freddy only continued trashing, only convincing the bull that the chains will hold.

Satisfied with the result, Djoser once again ignored the wolf, heading somewhere else. "HEY! Come back here!" Unbothered, the bovine continued his pace to a corner of the room behind the wolf, where there was a table. But the wolf was too angry to care. "I swear old man. If you don't let me go, you're gonna regret it!" Feeling his frustration welling back up inside him, Freddy gave out an empty threat. "I said LET. ME! G-"

"For heaven's sake... Do you ever shut up?" A familiar and intimidating voice pulled Freddy's focus from Djoser towards the dark corner of the dungeon.

Freddy did not realize the presence of another figure until he turned his gaze to the other side of the room, where the source of the frightening voice was coming from. Barely lit in the dim room, Sander stood with his arms crossed, brandishing his usual frown of disappointment. Despite the lack of his dark cape, wearing his almost normal suit, Sander managed to exude his usual threatening aura. It was probably the mask.

"Boss?" Freddy's aggressive demeanor quickly shifted into worries. "What's going on here?" The wolf started asking serious questions, knowing that when his serious boss was involved with something, it meant serious business. Sander perceived the wolf's respect when Freddy refrained from shouting for clarity, especially when the commander intentionally delayed his answer. So the mutt can actually learn.

"You are being punished." Sander pointed out directly. "Because of your impulsiveness, you ignored your instructions, endangered your teammates, and ultimately botched the latest mission." Sander made another pause to test the wolf. Freddy did not interrupt his boss' testimony, out of fear of making things worse for himself.

"Lord Hyde was very displeased." The mention of the councilor brought a sense of urgency in Freddy, a reaction that Sander noted. "This is not the first time you messed things up, and Lord Hyde would like it to be the last. He demanded that I fix this problem. By any means necessary." Another pause. "Even if it means disposing of you."

That last statement instigated Freddy to intervene. "WA- WAIT! YOU CA-" Which triggered a trap Sander had placed. A perverse trap.

"SILENCE!" It was not just authority or dominance in those words which rendered the whole room to obey. "That very impetuousness of yours is the problem! It has been a bane to the Shadow Decree and its cause." There was a hint of something else in Sander's tone. "I am left with no choice. But to punish that problem out of you." Something sadistic.

Freddy shrank with his ears flat on his head after that verbal bombardment. Even Djoser temporarily paused his preparation to witness a rare sight of his superior in action. After an explosive opening, the big bad commander was satisfied with his reprehension and proceeded to enact his well-thought punishment with another speech.

"Admittedly, I've punished you numerous times already." Sander listed. "I've sent you to the whipping post, left you in solitary confinement, and even considered confiscating your sunglasses." When the commander pulled out the custom-tailored eyewear from his pocket, that resulted in a gasping reaction from the wolf. Even though the commander was tempted to do it, he knew that it would not be enough.

Thanks to Freddy's masochistic traits, his fights would always involve him dishing out damage equal to what was inflicted on him. Unfortunately, this applied to his penalties as well which backfired with Freddy becoming even more unruly. "But then I realized I've been punishing you wrong." Djoser could have sworn he saw the commander smiling. "I've decided to heed Miss Cecilia's advice and explore a more... peculiar method."

Freddy managed to notice his boss gesturing an upward wave, finding out it was a signal for the bull behind him. A signal to start. "Put it in."

Djoser was swift, precise, and most importantly, powerful. Freddy could barely react when he felt the chains pulling his arm tighter and higher to the point of almost suspending him in the air if not for the spreader bar fastened to the floor. The wolf did not even have time to grasp what had happened when he felt a painful penetration between his buttcheeks.

"ARGH!!" The bull inserted an anal hook and quickly fixed the devious instrument to the same chains hanging the screaming wolf. Djoser finally let go of everything to see how the whole contraption held. When Freddy's soles touched the floor again, he was still recovering from the stinging pain of the penetration. But just as quickly as the pain came, it went away a few seconds later, leaving incessant cold metallic pressure in his ass.

"G- GET IT OUT!" No stranger to anal play, Freddy knew from the get-go it was an anal hook. But what he did not know was that it was attached to his wrist cuffs, until he instinctively pull his stretched arms which result in an unpleasant tug in his arse. Sander was impressed with Djoser's effective bondage when the chains jiggled to the wolf's every action, eliciting pain for every move.

"FUCK!" Freddy struggled to find a comfortable position, and as if on cue, he resorted to his impudence whenever he was under stress. But his furious thrashing only served to tug the anal hook harder or chafe his joints tighter, adding more agony to his misery. The bull took note of the dangerous loop of anger and pain recycling one another.

"Stop resisting, pup." Djoser felt the need to command the mad wolf from further injuring himself to point of permanent damage. "Yer making it worse."

"FUCK YOU!!" The wolf's outburst irritated the bull. Admittedly, you could not expect the impulsive Freddy to be in his right mind when strained. But Djoser still would not have any of the wolf's antics. The bovine walked up to Freddy's front, who was too distracted to see the incoming hand going straight for his throat. "GAAH-"

"Sit. Still." Without effort, Djoser raised his detainee with one hoof, relieving Freddy the trouble on his shoulders and anus, but also establishing dominance. The wolf instantly knew not to make a move just as one of his important organs was made vulnerable, especially when he felt those fingers slowly applying pressure.

"Enough Djoser." With that flip of the switch, Djoser's stoic demeanor returned, burying away the previous annoyance. The commander's commands had always been the loyal bovine's priority, thus he released the poor wolf's neck and spared him from asphyxiation. But the bull remained in front of Freddy who was now catching his breath after the previous tantrum. Djoser then contemplated an idea.

"Calmed down?" Djoser's words caught Freddy's attention. Djoser knew Freddy well enough that the bull predicted the wolf would flare up again after his short rest. Freddy's responsive snarl was a testament to that. "Don't resist." Djoser's finger slowly reached for Freddy's collar, which instilled dread into the wolf. Apparently, the collar was also attached to the chains suspending the wolf, thus any tugging would be translated in turn.

"Or else..." As Freddy grunted in discomfort, Djoser felt powerful knowing he had full control of the wolf. He pulled the collar harder, tasting dominance since ages ago.

Freddy scrunched his eyes in anticipation when the stinging pain in his arse was reaching an intense degree. But instead of a gradual increase into unbearable agony, he felt the forceful hoof pushing him backward and upward. "Back straight." Freddy heard the command and naturally, he followed the guiding hoof, composed himself, and felt the anal hook's pressure loosening.

"Legs spread." The spreader bar was already there, but what the bull meant, as he lightly kicked Freddy's knee wider, was to relax his thighs so he could stand easier. At the expense of unclenching his anus and accepting the cold metallic presence. "Face forward." Djoser did not need to force Freddy since he already knew how the collar would punish him if he twisted his neck. No choice but to limit his view to what was in front of him only.

Satisfied with how the wolf was arranged, Djoser finally left his field of vision, revealing to Freddy a one-way window, displaying a reflection of his circumstances. He saw himself in a compromising position and this reignited Freddy's frustration. But this time, with the lack of nagging pain poking his arse, he was calm enough to think of a proper getaway.

"I know I deserved to be punished." Freddy started voicing his opinions while concentrating on the divine power he received when he became an Esper. Being the same class of living beings, Djoser and Sander picked up the telltale signs of energy surging within the wolf. He was attempting to escape. "But I'm NOT having any of this bondage nonsense!"

Just as he released the pent-up energy to break the chains binding his wrist and ankles, he felt the same power fading away from his grasp instead. Still in subjugation.

"WHAT?!!" Freddy made a few more attempts, lightly tugging his bindings and pinching his rectum along the way. The bystanders in the room simply ignored him, knowing well enough that the wolf could not escape. When Freddy took a glimpse of the reflective window, he noticed the collar he was wearing glowed with Esper energy.

"That col- IS THAT THE INHIBITION COLLAR?!" Well aware of what it does, Freddy's fury reached new heights. This time, he did not flail his body nor gather ethereal energy, since the lupine prisoner had experienced the futility of those actions. "THIS IS MADNESS!!!" Freddy instead resorted to ear-shattering yelling.

"YOU CAN'T DO THIS TO ME!" With his remaining freedom only left to his muzzle (for now) he fiercely threw his words around. "FUCK YOU ALL!" Sander was slightly impressed with how Freddy's anger towards the situation overrode his fear of his superior. Freddy was angry, yes, but not because of the infuriating collar or visceral agony. He went through these things countless times prior and he survived each ordeal.

But something about the bondage, particularly the anal hook, incited worries in Freddy. Previously he was reprimanded with physical pain only, but the obscene elements of this whole arrangement scared him. In turn, for the lack of emotional discipline and inarticulated communication, those fear translated into volatile fury. "Let me go!" Sander noted how fatigue started to overcome the wolf, which cued him in for the next phase.

"Let's get this over with." Freddy braced himself for the worse but was not prepared when Sander pulled him by the collar, prompting the hook. And then kissed him.

Freddy had half a mind to bite his commander. As a matter of fact, with all the wrath egging him on, he was just about to do it. But the hesitation and weariness gave an opening for Sander to cast his spell. It was not your usual intimate kiss, particularly not when the canine was devoid of any sense of romance. It was just a means to punish.

At first, Freddy thought it was the dog's tongue sloshing around in his muzzle, but it felt nothing like it with its rough and sandy. At this point, the wolf was already biting out of panic, but to no avail, as the otherworldly yet granular material in his throat did not give under his jaw strength. The wolf's anxiety went up another level when he was forced to swallow those grains of Sander's ether (so Freddy concluded).

Unfortunately, Freddy could do nothing but stare helplessly with worries into Sander's eyes, who in turn reciprocated with a sadistic glare while securing his hold on the lupine. The canine commander always had a penetrative gaze, and when Freddy was the main subject of those pair of yellow glares, he could not help the rising heat inside his jockstrap.

When Sander was done with whatever he was doing, he distanced himself from the wolf, leaving Freddy with a small gift. Freddy could still feel the uncomfortable presence in his muzzle, and as he took a glimpse of his reflection, the wolf saw that he was wearing a ball gag with straps holding it in. He grunted once to express displeasure. But the new bondage equipment was the least of the lupine's worries. "Waff thid uu thoo...?"

Sander sadistically decided to respond to the muffled question. By not answering it. "You'll see." This time, Sander did not even try to hide his smile.

Right on time, the wolf felt the effect of those grains of energy spread throughout his whole body. It started with an invigorating warmth, washing away the self-inflicted lethargy, allowing the wolf to stand more firm. The soothing sensation was also comfortable and these enchanting effects left the lupine baffled. Was he not supposed to be punished?

His confusion got worse when he was left to his own device for the time being. With his limited field of vision, he could barely see Sander mumbling to himself by his periphery. And Djoser was too far into the dim room for the wolf to discern through the reflection. That leaves Freddy to stare at himself and contemplate his situation.

At first, he was trying to guess what kind of punishment awaits him. The sexual innuendos suggested lewd thoughts and that brought Freddy to examine his bondage. He was trussed up real good and the spread limbs left out so many vulnerable spots. Then the wolf had an idea of someone else on the other side of the window, looking at his displayed helplessness. The jockstrap felt a bit tight at the attention.

He closed his eyes, pushing out those horny thoughts. But the lack of sight only enhanced his other senses, or in this case, his perception of touch. The incessant pressure in his rectum planted the image of the wolf taking something under his tail. He was not a stranger to anal but to be on the submissive end instead of power-bottoming was a whole new territory. Freddy opened back his eyes, dreading the inevitable.

Freddy lost the battle of will, unable to deny his own perversion of being exposed for everyone to see. Right then and there, he was having one of his exhibitionistic boners.

"Am ready." Freddy's attention was pulled from his lustful stupor after he heard the bull's booming voice coming from directly behind the wolf. He remained still, hoping to mitigate the attention toward his groin. Through the pseudo mirror, the wolf was able to differentiate the bull's current attire. Or lack thereof, since Djoser was shirtless.

Despite the lupine's lean figure fixed as the centerpiece, Djoser's bulking silhouette was still apparent. This was further emphasized when the bulls' bodily warmth reached Freddy as Djoser gripped the lupine's waist and pulled Freddy closer to him. Freddy shuddered with anticipation when his backside was leaned against the bull's strong front. The wolf's eyes widened when he felt another hot flesh rest between his butt.

"You may start whenever." Sander's gesture incited one last struggle from the wolf, vainly hoping his reenergized version would be enough to break free. At least free from the impending penetration. But the bondage resisted his effort and Djoser's hold remained firm and unrelenting. The wolf felt the familiar sensation of a glans landing on his hole.

Freddy was conscious enough of Djoser's defining characteristics; thick, compact, and massive. It became even more alarming when he felt the pressure between his legs gradually seeping through. The shock of the anal hook being shoved into him was already bitter, and Freddy feared the pain of yielding to the monster behind him. The tension paused momentarily, and Freddy knew it was the calm before the storm. "Submit."

"HMMPH!!!" The penetration was definitely distressing as it sent an overload of sensation right up the wolf's spine. Informing Freddy that there was a big dick inside of him.

"Tight wolf." Djoser adjusted his position which brought out more grunts from the overwhelmed lupine. Freddy, too beaten from the shock, finally became passive to whatever ministration awaited him. "Not for long..." The wolf felt the hot rod slowly ebbing back and forth, steadily inserting more of it with each swing. Freddy stiffened for the incoming torment.

But to the wolf's surprise, there was no more pain after such a violent event. And when the wolf recalled back, there was actually minimal pain during the whole scene. The penetration was mind-boggling, yes, but it was just his prostate roaring in immense pleasure. Unlike his many experiences of bottoming, this one lacks the stinging of penetration and the soreness of stretching. There was instead a familiar warm soothing energy.

"So you finally noticed." Just as Freddy came to a deduction, Sander walked into his view and confirmed the lupine's suspicion. "It's not perfect, but my enhancement should do the trick." This does not make any sense to Freddy. Not only was he energized to be labor-ready, but also numbed of pain as his discipline. "Confused?" The canine commander picked up Freddy's signs of inner turmoil. "Good."

The wolf did not have enough time to figure out what Sander meant. Partly because Djoser was already balls deep. Fortunately, there was no unbearable agony. Just distracting pleasure. Under normal circumstances, Freddy would show more tact when it comes to sexual pleasure. But Sander's enhancement and Djoser's thickness were too much to handle, thus Freddy finally let out his first muffled moan of the night (or day).

"Mmph..." Freddy was losing himself in pleasure, with his tented jockstrap throbbing enthusiastically, convincing anyone in the room that he was having a blast.

Djoser let out a hefty snort, a sign of content from the successful break-in, forcing out a rewarding response from the stubborn wolf. The pleasurable feeling of a warm squeeze around his shaft was just icing on the cake. The bull adjusted his tight position and took note of how the wolf squirmed under his ministration. Djoser felt slightly tipsy.

Djoser was always the passive player when it comes to lovemaking. The bull had his fair share of sex when some of his subordinates fancy his thickness. But the large bovine always had to be gentle with his thrusts and comply with others' limits. But this time he had full autonomy since Freddy had no say in this punishment. And the plan where Djoser could do whatever he wants to do wolf... Excites him.

Much to Freddy's alarm, the omnipresent dick inside of him started moving again. And instead of gradually picking up speed so his partner could accommodate the size, Djoser mercilessly raised the tempo in mere seconds. The follow-up whines from Freddy signified he was on track and this only encouraged the usually calm bull.

The fucking was maintained at a constantly intense pace, pursued by the wolf prisoner's periodic gruntings. Djoser was savoring the experience, continuing his barrage until they reach the anticipated moment. In the meantime, the bull had an idea to indulge himself, where instead of pumping to pleasure himself, he changed the angle of his trajectory to make one thrust towards the acclaimed pleasure point for males. "HMMPHHH!"

"Gahhahaha!" Djoser let out a hearty laugh. To force feedback from his prisoner stirred his dick to throb harder, as it was more pleasurable than fucking ceaselessly.

Djoser switched gear from speedy mindless humping to strong precise poke. Without failure, each thrust strongly brought out meek moans from the otherwise assertive wolf. And steadily, Djoser could see Freddy's frantic struggle shifting into something less aggressive. The bull ceased his pumping to confirm his suspicion.

"Hmm..." A shaky whine, worthy of a lil pup, escaped the ball gag. The bovine dom also took note of how Freddy's motion was no longer focused on his bondage. But more accentuated towards his arse, as the wolf attempted to grind against the bull's dick. Djoser reciprocated with another thrust, before leaning his head to Freddy's ear to tease further.

"Puppy loves a big bone, don't yer." Freddy froze when he heard that, then he let out a strong grunt, indicating the state of his will. But Djoser had more tricks up his sleeve. Particularly one that involved changing his grip from the wolf's waist to instead grab what was at the front. "Yer fooling no one." To prove his point, Djoser squeezed the tented jockstrap, relishing the dominance of claiming the other's wolfhood.

This time, Freddy did not even try to hide his desire when he let out another whine. Djoser was amused when the wolf reflexively humped into his hoofs for more bliss. But the bull was one in control, and the only pleasure Freddy would get will be from his prostate. Djoser gave another thrust to stun the wolf and took the opportunity to roughly yank the jockstrap. Freddy realized a second late when he was stripped of his last clothing.

The wolfhood was finally free in all its erected glory and the bovine fingers returned to the wolf's waist, beckoning the continuation of his torment. "Yer mine puppy."

Dominating Freddy was fun, but Djoser had a job to do. The bull thrust was constant, slowly pushing the wolf to the intended goal, as per his instructions. Commander Sander only told him to fuck the punished lupine and slowly increase in tempo when signaled. Djoser saw his commander give out a wave and as a loyal servant, he did as he was told.

From the increased intensity, Freddy's muffled moans reverberated through the whole room, and in turn, the whole idea of discipline eluded the bovine. He thought this whole setup was meant to punish the stubborn wolf, not reward him with carnal satisfaction. Sander gave another wave, and Djoser followed, albeit begrudgingly.

As minutes passed by, things started to differ, especially when Freddy's pleasure moans turned into desperate whines. It just dawned on the bovine that the wolf was still holding on from climax despite the tumultuous stimulations. No, that was not it. Djoser could see how the vulpine's body language was concentrated on trying to get off. From swaying hips to anal clenching, just to add a little bit of pleasure to set himself off. But he could not.

"The spell actually works." Without breaking his thrusting momentum, Djoser listened to his commander. "I bet you were wondering why you haven't cum even though Djoser fucking your brains out." Freddy's frantic whinings failed to interrupt Sander's explanation. "The enhancement not only replenishes your energy and numbs your pain. It also increases your stamina. Particularly your threshold to climax."

"HMMPHHH!" Seeing the adamant wolf finally cracking, flared up the spark of dominance into a flaming desire for subjection. Djoser's excitement took over again.

"Yer been a bad pup, Freddy." The bovine stopped moving, making sure his prisoner could hear his perverse tone. "Very bad lil puppy." Freddy shuddering in anticipation only encouraged the bull to inch one of his hoove forward. "Do yer know what happens to bad pups?" Djoser did not mind when the fearful wolf did not answer him. Probably because of those rough fingers curled around his wolfhood. "Bad pups don't get treats."

Relentlessly, Djoser stroked the already stiff member to send intense pleasure that would push any male off the edge. But true to the commander's words, Freddy was unable to ejaculate, or to be precise there was not enough stimulation to do so. But it was definitely enough to convince the desperate vulpine of impending orgasm and witnessing Freddy yielding under the blissful pressure brought a smile to Djoser's face.

All those times when Freddy was chastened traditionally, Djoser had to be the punisher and he was always irked by the fact that the wolf was unfazed by it. The masochistic vulpine relished the physical torment and the bull had enough of vainly inflating Freddy's ego. So when a new form of pain proved effective to the wolf, the bull kicked off.

He was like a kid with his new toy and he celebrated by going full throttle. Maintaining his assault on the wolf's dick, Djoser used his free hand to sensually caress the vulpine's chiseled abdomen, before groping the hefty chest. The bull was even more delighted when Freddy reacted to his pectoral fondling evolving into nipple-pinching.

Djoser was slightly glad of the troublemaking wolf. For presenting him with the chance to re-live his dominant desires and do whatever he wants. "Let's have some fun."

"I'm happy to see you indulging yourself, Djoser." The bull snapped from the intoxicating power, realizing that he acted out of order. Sander noticed the bull's worries and quickly dismissed them. "Don't worry about overdoing it. I've made sure that Freddy here won't cum unless certain conditions are met. Feel free to let loose."

Hearing those words, the vulpine whined while the bovine chortled, confirming the punishment's continuance. The canine commander proceeded to sit by the sofa at the corner and enjoy the show. When he heard Freddy's whines, Sander was satisfied that Miss Cecilia's method had worked. But something else was troubling the commander.

This whole punishment was about using endless pleasure to torment thus the significance of his enhancement to increase his sensitivity and stamina. But the pain-numbing was counterproductive. Initially, it was meant to remove an element that may distract the wolf from blissful torture. But with a stroke of inspiration, Sander had a sadistic idea to turn the previous problems into solutions.

He stood up from his comfort to once again approach the wolf. The punished and the punisher saw this but they did stop their business (not that Freddy could anyway). Sander placed his paw on the wolf's chest and Freddy dreaded when he noticed the ethereal glow of the commander's power-taking place. Sander felt gleeful in seeing the anticipation behind the wolf's eye as they stared in helplessness.

"Djoser. Spank him." As swift as the command came, so does the bovine's hooves landing roughly on Freddy's arse, leaving it smarting and stinging with pain.

"MMMRGGGH!!!" Sander observed the wolf writhing in pain with his eyes closed and fang bared. A typical reaction, but not what the canine was going for. He signaled Djoser to spank, alternating between left and right, consistently powerful impact, making it as predictable as possible so that Freddy's mind will grow accustomed to it faster.

At one point, Sander smirked plastered on his face, when he heard the wolf's grunts turn into moans. His improvisation worked. The commander removed the analgesic effects of his spell to reintroduce pain back to Freddy, the masochist. The physical pain was just a different form of pleasure to the wolf. But now that pleasure was used to add more mental pain instead. Sander's paw was still touching the restrained body. Before he lowered it.

"HMMPH!" Freddy's eyes widened at the sensation of his wolfhood constricted by a grip, but instead of the rough hooves, this time he felt sharp claws dangerously scratching his precious tool. Sander locked eyes with the scared wolf, slightly entertained with the way Freddy's hopelessly pleading with a ball gag still lodged in his muzzle. But that was not enough to stop Sander from squeezing. Slowly and painfully.

"HHRRRGHH!!!" It probably felt like barbed wire entangled around his dick and slowly constricting. But in a good way. Sander confirmed that Freddy was drawing pleasure from the torture when the commander took note of the leaking pre-cum. With Djoser's spanking translated into painful anal and Sander's squeezing as a painful handjob, it did not take long to push Freddy to the edge of climax which he could not go over.

"SHTOOP!" When he heard the muffled pleas, the canine commander was reminded of something important. "PEESH!!!" Sander remembered how to have fun sadistically.

"PEESSH! LEE ME CUHHM!!!" The vulpine's pleading triggered something in Sander and he had no choice but to cease his part of the torture, in order to adjust his suddenly tight crotch. The commander had forgotten when was the last time he felt this way. As if being busy with work was not hard enough, the chance of finding a partner who could actually handle his abuse left Sander with no room to satisfy his sinister desire.

"AI DO ANIHING!! PWEESH!!" But the punished wolf right in front of Sander was luring him with screams and beggings. The punishment was already a success. There was nothing else to do but let the wolf marinate in his pleasure torture until the time was ripe. Then Sander thought, what was the harm of mixing business with pleasure?

"Mrrgh..." Freddy felt his dick in Sander's grasp again, and the wolf flinched out of fear of more pleasurable pain. Sander grinned and began slowly stroking the pent-up wolfhood. The commander could see that the wolf was skeptical of the gentle ministration. But when the canine's spell started to manifest and manipulate sandy ropes, Sander savour the slow twitch of discomfort when those rough threads intertwined intricately.

"Hmph?" Freddy could not see what happen, thus the commander candidly stepped aside to reveal the surprise through the reflection. Sander did not want to miss the vulpine's reaction as he stared in disbelief toward his ensnared cock. Black threads decorated his red erection from the glans all the way to the knot. Even his balls were stretched forward.

"Do you like it?" Sander tenderly caressed the adorned genital, eliciting doubtful moans from the wolf. "You're going to love the next part."

More glowing paws, and this time Sander reached for the vulnerable muscular chest that was begging to be played with. Freddy only grunted in sharp pain at the feeling of his hard nipples being clamped shut by an apparatus. The wolf felt the sting persisting especially when Sander demonstrated the connection of both clamps via a chain. But particularly, Sander was presenting a slim rod attached to the center of the chains.

Freddy's eyes could not follow the movement of Sander's paw when they went down out of his view. But the sadistic canine made sure the wolf knew what was taking place by emphasizing the gradual tugging of the clamps followed by the incessant poking on his glans. Freddy renewed his struggles as a response to the merciless invasion of the urethral plug. Sander licked his lips, purposefully seesawing back and forth, to extend the torment.

Once Sander was satisfied, the sounding rod was fully embedded, but not before the commander locked it into place. Freddy could feel tightening around his glans followed by mild shifting of the shibari on his dick. What was more apparent to the wolf was how his dick remained vertical while the chains connected to his nipples maintained taut.

This new predicament was further explained with the help of Djoser as he resumed fucking the punished vulpine's arse. The intensity of the thrusts was not even close to mind-breaking or orgasm-inducing, but the new sensation towards Freddy's wolfhood was. Every thrust, resulted in the bobbing of the pent-up dick, which the inertia will proceed to tug on the nipple clamps, eliciting erogenous pain and thus driving the wolf crazy.

The grainy shibari binds on his dick would also stretch and tighten in turn to the oscillation, stroking Freddy's member with its rough texture. Sander took pride in his torture.

Even though it was just a few dozen minutes, Freddy felt the torture had gone for an eternity. "Hmmphh!!" Another strong thrust from the bull behind him, crushing the wolf's sensitive prostate and sending pleasurable signals through his body. He was further convinced that he would climax from Sander's shibari torture. But still, he could not.

"Peeshh..." The enhancement conjured on him made sure the wolf had limitless energy, but he was already getting tired of pleading, figuring that he will be denied relief again. Freddy gazed with imploring eyes towards the merciless stare of his commander. The wolf realized that those glares, which were witnessing his salacious predicament, were also turning him on, making things worse.

"Pees. Leeh mee cuhhm..." The torture finally broke Freddy. At the mercy of his senior colleagues, he was ready to do anything just to cum right then and there. But as Sander mentioned, the vulpine could not cum unless they satisfied certain requirements. And only the commander knew what it was, further empowering the helplessness of the situation. There was nothing Freddy could do but take it.

"I'll let you cum." As sudden as the statement was spoken, so was the sudden squeeze of Freddy's testicles. But that was not enough stimulation to distract the wolf from what really matters. Freddy hopefully waited and listen to what the commander had to say, fully anticipating a catch to the previous declaration. "If you'll do what I say."

Sander sensually massaged the orbs, teasing his prisoner, while giving the ultimatum that the wolf will get his orgasm if he was obedient. Freddy nodded frantically.

With a flick of his fingers, Sander dispersed the ball gag, restoring the vulpine's ability of speech. But Freddy had half a mind to say anything, getting the hint that he was to play the role of good pup if he was to get what he wanted. So he remained silent for the most part (letting out occasional moans) despite the ball fondling and butt fucking.

"Repeat after me." The commander finally said something and Freddy gave his utmost focus in spite of the pleasurable distractions. "I, Freddy, am sorry for fucking up the previous mission while endangering my teammates' well-being." It was a fairly simple oath-taking, and Freddy complied without much interruption (Djoser was still fucking).

Sander resumed. "I also swear my allegiance to the Shadow Decree and dedicated my absolute loyalty to Lord Hyde." It was meant to strengthen the idea of submission, and because Freddy was motivated for his orgasm, he repeated the commander's pledge with full enthusiasm. But Freddy could see in Sander's eye that he was not done yet and that there was one more obstacle to overcome.

The canine commander was taking his time, alternating his teasing from ball fondling, to dick stroking. It felt especially possessive when those fingers curled against the engorged knot, promising sensitive pleasure if squeezed. "Last one." Freddy could not afford to mess this up. He was ready to say whatever the commander wanted to hear. But then dread overcame the wolf when he saw the commander's sadistic smirk.

"Say that you're a bitch whore in heat, who's desperate to get his ass fucked by anyone just to cum." And just like that, Freddy hesitated.

"Wait. Wha- ARGH!" Sander squeezed the knot in his grasp, knowing full well what most canidae would feel. Simulating a tie, it would feel like orgasm would be just around the corner, but the restriction he put on Freddy would only leave the vulpine denied, thus why he was screaming in agony.

"Did I stutter?" After squeezing for a few minutes, the commander finally gave the wolf some breathing room. Sander knew Freddy had quite the inflated ego and the fact that the wolf hesitated to do his last demand means that there was still some leftover pride to be snuffed out. And what better way to end his punishment than with proper humiliation.

"I- I..." Still dawdling, Sander gradually clenched his fingers, still holding the sensitive knot as his prisoner. That mild discomfort was more than enough to push Freddy to shame himself. "I'm just a bitch whore slut in heat! And I want a big thick dick to fuck my brains out until I cum! Please!! LET ME CUM!!!" The final edits the wolf added were not part of the script, but it was not bad either.

"Well done Freddy." The commander released the captive testicles and backed off from the centerpiece of the room. Both Freddy and Djoser took note of their boss' change in demeanor. "You've earned yourself an orgasm." If the signs were not clear before, seeing Sander unbuttoning his shirt now was like a beacon. As for his pants, he merely unfasten the zipper leaving enough breathing room to reveal his toned torso and hard-on.

"And here's how you could reach it." Sander kept the mask on. He knew most would fear his infamous mask, including the wolf. The dread on Freddy excites him.

It has been a long while since Sander satisfied his wanton desires, feeling slightly liberated, not just from his garments, but from his self-discipline too. Thanks to Freddy's natural masochism and the enhancement that was placed on him, Sander did not need to hold back his sadism. But Sander knew not to push it, so he decided on something tame.

Sander reapproached the bound wolf and made sure they were close enough to look each other in the eye, face-to-face. And also close enough, waist-to-waist, so that Sander could grasp both erected dicks in one paw. The commander began his explanation just as he started stroking the two members. "The spell I've put on you has multiple effects. But the important one that would allow you to climax is the hypnotic lock I've put in your mind."

Freddy tried to focus on his commander's words, but the stimulation he was subjected to was too much and he was already struggling to be as obedient as possible by moaning less and asking lesser. Alas, Sander continued without care. "So in order cum, not only do you need to be in a state of extreme pleasure already bursting for orgasm, but someone else needs to say the two phrases trigger words to set you off."

Sander could see Freddy was at his emotional breaking point, struggling between begging his captor for relief and staying in silent obedience so as to not mess things up. And Sander was about to push it. "Now... I just need to say the words. And you'll cum." Freddy's eyes widen, expecting the anticipated. "Or I could also not say it." Freddy was shocked. "And leave you here with Djoser for the rest of the night. Without any chance of orgasm."

That was it. The realization of hopelessness. The sweet despair in Freddy's eyes. When Sander saw a trickle of tears, that was when he pulled the trigger.

"Good boy." Sander made sure to time the trigger word with his incoming orgasm so that they both would climax simultaneously. The sadistic canine relished the look on Freddy's face, with his eyes rolled backward and tongue lolling forward, obvious extreme pleasures had struck the wolf. The commander knew the trigger words were just a key to unlock the dam, so the magnitude of Freddy's orgasm was all thanks to prior teasing.

Sander himself was in bliss of his own. When Freddy stared at him with those teary eyes, the canine commander could not contain his excitement at the sight of how cute the wolf was at that moment. The way that handsome vulpine muzzle frown in desperation. Followed by the pathetic whine, music to the commander's ears. But most importantly, the sincere pain he was under. Sander had to give credit to Freddy for an A+ puppy dog eyes.

The orgasm went on for quite a while. Sander managed to shoot about 5 ropes of cum before he started drizzling. Freddy was still going strong from all the pent-up punishment he was subjected to. Sander made sure to angle both of their dicks so that only the punished wolf would be drenched in semen. Some even got into his mouth.

Once everything settled down, Sander finally released both of their cocks and backed away from the mess. Using his ability to manipulate sand, he easily cleansed his body before he dressed into decency again. By that time, Djoser was also done with fucking the vulpine and started cleaning himself. Guess the bull got one off when they were having fun.

"Let's call it a night." The commander gave his last command for the night. "I'm satisfied enough with the punishment. Can I trust you to handle everything else, Djoser?"

"Yes, boss." With a don of his cape, Sander was ready to leave the dungeon after his loyal underling gave his affirmation. He made one last glance backward just to see Freddy still recuperating from the intense show, but otherwise fine and unharmed albeit still on bondage. Sander planned for another session with the masochistic wolf, maybe something more casual instead of business. Sander actually valued Freddy's company.

And just like, the canine boss had left the room right at the moment Freddy finished regaining his composure. He was still in less than a preferable condition with all the bondage and spunk spread over his body. Freddy could still feel some lingering effect from the enchantment, particularly the part where his wolfhood was still engorged and ready for another orgasm. At least the torturous equipment on his nipples and genitals disappeared.

Freddy took a minute more to struggle in his bondage before he realized Djoser had been staring at the wolf. "Hey old man!" The bull did not flinch. "You heard the boss. Punishment's over. So let me go." The bovine finally moved, but Freddy was too caught up in his predicament he did not realize the body language Djoser was expressing.

"ARGHH!" The wolf retaliated at the sensation of his dick being squeezed. "WHAT GIVES?!!! MRHH!" The pressure never relented. Actually, Djoser made it particularly tighter around the knot, coaxing another orgasm from the wolf. "Urgh... Arghhh!" As quickly as the sensation came, so does Freddy's emotion as it turned from shock into dread.

"Boss said I handle everything." The bull started as a matter of factly while looking straight into Freddy's eyes. "That means, I decide when punishments are over." Djoser locked his gaze on the wolf with a passionate stare. "And it's far from over."

Before Freddy could ask for clarification, the bull already started giving a brief explanation. "Boss only broke you. He did not fix you." The wolf was confused. "If I let yer go now, yer will be obedient, scared of punishment." Djoser could see that Freddy was following the conversation. "But yer still have no self-control. Yer will make same mistakes again even though yer learned yer lesson." The bull actually made sense.

"So I will train lil pup." The bull gave his conclusion. "Train until yer calmer. Better. Stronger..." The last adjective has a hint of desirous in it. "Now back straight, spread yer legs, and face forward." Djoser did give the wolf some time to adjust his position to brace for what was coming. And the bull did not hesitate to start when he saw Freddy dawdled instead. The grip on the knot tightened, pushing the wolf into the familiar wall.

Freddy let out a grunt before he started fidgeting around in discomfort, but it only made things worse by adding more stimulation to his already-edged state. "Yer struggle, this continues. Calm down. Take deep breath." Instead of snapping in anger like he always did, Freddy actually listened this time and obeyed. He breathed, then the grip felt softer.

"That's it! Now stay." The pressure from Djoser's hooves never relented nor strengthen. The bovine just kept a constant grasp that was more of a constant nagging bliss to Freddy's mind. Compared to the previous torture he went through, this knot-tieing simulation was just a mild push of his pleasure button. Freddy could still keep his cool.

Once Djoser deemed plenty, he uttered the words "Good boy" which triggered the wolf to burst out a moan simultaneous to the release of his second orgasm of the night.

It was not as intense as the first, due to the lack of pressure build-up. Nonetheless, it was still an orgasm that sapped away some strength. "Yer ok?" Freddy nodded in response. Thanks to the lingering enhancement, the wolf's stamina replenished quickly. Which also shortened his refractory period thus his wolfhood was primed for another climax.

Djoser noticed this and proceeded. "Ready for next round?" The bull's sudden interest in consent concerned the vulpine. But Freddy had half a mind to be disobedient now and decided to stay on the Djoser's good side while still being under his mercy. The wolf affirmed the bull, then pressure on his knot returned.

"Stay." Just one word to command the wolf on what to do, and Freddy obeyed despite the difficulty. This time Djoser took a longer time to edge the wolfhood while adding extra stimulations such as gentle stroking, ball fondling, and nipple pinching. But the stimulation was not overwhelming as it was meant to test the wolf's patience. "Good boy." The third orgasm came, surprisingly more satisfying, rewarding Freddy for good behavior.

"Wanna continue? It will be tougher." Even though Freddy will always be physically ready, Djoser had to make sure the wolf was also mentally prepared for what was coming next. As soon Freddy gave the green light, the bovine smirked before replacing the hooves gripping the ever-engorged knot. "Lick it." Djoser could see the disbelief in the vulpine's eyes, but also the willingness to obey. The struggle was there, but the lesson prevailed.

"That's it." Djoser was happy to see a strong warrior licking his own semen and Freddy himself also got a bit excited from the bull's gaze. They were enjoying themselves.

At some point in the night, it was no longer just about the training. After the fifth orgasm, Freddy started playing an active role of a desperate slut, moaning the bull's name, and hitting the right verbal button. Sometime after the eighth, Djoser could no longer repress his passion and stated how much the bull wanted the handsome wolf for himself.

It did not take long before both beastmen had their tongues interlocking one another, moaning and grunting into each other's throats. Djoser had forgone the wolfhood to instead make full use of both his appendages to grope every strong musculature. Freddy himself took the initiative to gyrate his own hips in hopes to frot with the thick member in front of his.

But in the end, Djoser was the one in control. So when the bull presumed that Freddy had too much fun, Djoser tugged the anal plug, forcing Freddy backward and upward in an arch, denying the wolf any pleasure. The bull even took the opportunity to whisper variations of the phrases 'good boy' just to tease Freddy of a possible orgasm.

"Djoser. Please..." The bull grinned, knowing he had successfully subdued the horny wolf, cornering Freddy into begging for another relief. But Djoser miscalculated. The wolf was not actually libidinous enough to want an orgasm (since he got plenty already). Freddy wanted something else and he laid off his trap by acting in his most seductive voice. "Please fuck me, daddy Djoser~! I want your thick juicy dick inside of me~."

Djoser was unable to resist Freddy's act of desperation. The bull did not even think of what he was about to do next. He removed the anal hook, only to replace it with his member.

The motion was swift but not painful. After the recent pummelling, there was no resistance between the bull's dick and the wolf's tail hole--just a quick penetration, followed by blissful stimulation. Freddy felt triumphant after winning the battle of salaciousness, and half expected the bull to go on a rampage at his prostate. But that did not happen. "Old ma-"

"Good boy." Freddy turned around in an attempt to see what had happened, only to be assaulted simultaneously by the sensation of a familiar tongue invading his muzzle and rough hooves squeezing his knot. The wolf could only moan into the kiss and climax, relishing the additional stimulation of his prostate nudged every time he clenched.

In the short afterglow, Djoser made quick work to release the anchor holding the spreader bar and unchained Freddy's wrist from the ceiling. But the bull had no intention of untying his prisoner. In fact, while Freddy was impaled and partially bound, Djoser managed to maneuver both of them to lie on a conveniently prepared dungeon bed, with Freddy resting above his senior's robust body. Those pecs make for good pillows.

The bull briefly broke their kiss and resecured the wolf's wrist and ankles to the bed's edge. The wolf also felt the bull's thick forearms hugging (and the juicy dick skewering), keeping him in place. Djoser forced the wolf to face him again for another kiss while his other hand ventured downward to take control of the excited wolfhood. There was no more aggressive fucking or torturous edging. Just passionate kissing and intimate cuddling.

The bull relaxed to the warm clenching while the wolf yielded to the prostate massage. With all the time, energy, and privacy that they had, they would remain detained in that dungeon for the whole night. Just the two of them.

Djoser rewarded Freddy with another "Good boy..."