Busy Weekend

Sam's night had been a restless one, as had been most of his nights ever since his dad had started to fool around with him, grooming the young boy to become the perfect little servant and sex slave to the chubby man. The little wolf's Friday afternoon had been filled with nothing except lewd and taboo acts of increasing intensity, with all of his holes being used one after another, tied up and pinned down, helpless as he took his father again and again until he could barely even keep his eyes open let alone stand up, and the wolf pup loved every single second of it. Though he'd been more than a little hesitant at the start about the drastic direction that the relationship between him and Philip had gone, Sam couldn't think of a single thing that'd bring him more joy than pleasuring his dad in any way he could, wanting to give his body over to the man, to be used and abused at Phil's discretion no matter what. That did however mean that the quality of his sleep usually wasn't great, what with the aching of having all of his holes knotted several times in a row and getting stretched out to his absolute limits. The discomfort of the rough playing only grew worse after it was all done, as the high of the poppers slowly faded away and left the boy without the cushion of the drugs to ease his pain, leaving him to quietly moan and squirm throughout the night. The situation wasn't made any better by the large buttplug stuffed in his tailhole, holding in several loads of cum that had been pumped inside of him the day before, his fur drenched in the dried spunk that hadn't made it into either his muzzle or pucker. 

Writhing around under the blanket, trying for some time to get back to sleep and catch just a few more minutes of sleep, Sam finally gave up and poked his head out from under the covers, groaning quietly as he squinted at the window, spotting that the sun was only barely starting to peek up from beyond the horizon. Laying next to the little wolf was his dad, still in deep sleep after all of the hard exercise he'd been through last night, snoring loudly, still dressed in his leather harness and sporting a massive case of morning wood. Watching his father's bulge throbbing and moving around under the blanket, Sam couldn't help but to crawl right up against the chubby male's side, hungry for more even though his body wasn't even close to getting over the last round of fun that the pair had had. Biting his lip and letting out a tiny whimper as he felt his tailhole clenching around the plug shoved into his ass, the boy slowly reached a hand under his dad's blanket, groping around in the dark until his fingers wrapped around a meaty girth, feeling the knot pulsing against his palm. 

Stirring from his deep slumber little by little, starting with a snort, then a small moan, before finally prying open his eyes, Philip lifted up his head to see his little son curled up under his armpit, the cub's tiny hands feeling around his crotch, stroking and massaging at his morning wood. The man groaned sleepily, pushing aside the blanket as he cupped the boy's rear, rubbing Sam's ass and thighs as he nudged the puppy closer towards his crotch, 
"Hungry for breakfast~?" 
Sam smiled and crawled over to his dad's cock, laying belly down on top of the larger canine, his feet resting on Phil's shoulders as he gripped the adult's dick, only barely able to wrap his hands around the entirety of the girth even when using them both. Philip let his son play with his shaft for a few minutes while he woke up, watching the young wolf's tailhole twitching around the large buttplug, his deep and relaxed breaths getting slightly more rapid as the cub rubbed at his knot like it was a magic lamp. Quickly getting too worked up for foreplay, Phil decided to take matters into his own hands, grabbing the back of Sam's head as well as his cock, angling his tip towards the kid's muzzle. He grinned at the boy immediately opening up wide in response to him offering up his manhood, pushing Sam's head forwards and moaning as he felt the kid's wet and warm maw starting to envelop his cock, the pup's tongue gliding across the underside of his knotted length until he was completely hilted. Sam tried not to struggle as his dad's tip teased the back of his throat, the spurts of precum almost triggering his gag reflex as his hands trembled slightly, his face going a light shade of red as he strained to get any air past the thick slab of meat crammed into his mouth. He knew that the man wouldn't stay buried up to the knot for long however, having to wait for just a few seconds before the thrusting and grunting began, his arms wrapping around Philip's thighs as his dad fucked his throat, making it even more harder than before for him to try to stay still, though he couldn't move his head more than a few inches even if he tried. Keeping his son pinned against his dick, Phil ploughed into the boy's tight muzzle without mercy, huffing as he made the bed squeak, bucking up while simultaneously slamming Sam's head down against his crotch, using his free hand to play with the buttplug hidden underneath the puppy's tail. Squeaking out muffled whimpers as he felt his dad tugging at the large plug in his asshole, Sam endured both the toying as well as the muzzle fuck, bracing himself against the man's legs until Philip had finally had enough, one last push into his throat causing the thick red rocket to release its load right down his gullet, gushing down into his belly while his father moaned behind him. 

With his lungs screaming for air and his jaw aching as his dad's knot threatened to tie his muzzle, Sam did his best to stay calm and just guzzle down the man's seed, the overflow of the load seeping from the corners of his maw as he quivered, having to stay hilted for nearly a minute without the chance to breathe before Phil finally let go of his head. Pulling his mouth off of the adult's cock, Sam quickly covered his muzzle with his hands to hold in all of the cum as he coughed and sputtered, a few last stray ropes of the larger wolf's jizz draping themselves over his face and head as the dripping wet shaft throbbed in front of the boy, unleashing the remainder of his dad's load all over him while he swallowed what remained in his mouth. Panting for a few moments, Philip felt the leather harness tightening around him as his chest puffed up with every breath, lifting his head after he'd recovered from his orgasm, watching with a grin as his son was trying to clean up the mess he'd made all over his own crotch and the cub's face. Spent for the time being, but still eager to continue playing with the boy, Phil decided that it was time to train his little servant's skills at self control, licking his lips as he grabbed the pup's tail and yanked Sam up towards him, tugging the cub away from his cock. Giving a startled squeak, Sam didn't try to fight back as his dad tossed him onto the bed on his back, climbing on top of him, their muzzles separated only by a hair as the large man smirked while cupping his family jewels, teasing his sheath and balls at the same time with a gentle massage, 
"No matter what, you're not allowed to cum, do you understand~?" 
Shivering and covering his blushing face, Sam nodded, getting a sly smile from his dad, 
"Good~" 

Pressing his chest against the boy's and pushing his cock on his son's crotch, Philip began to slowly and gently hump the little wolf, his hands resting on either side of Sam's head as he panted into the kid's ear, feeling the canine's sheath starting to stir and swell as his own girth rubbed against it. Squirming underneath his dad, Sam was fully erect within just a few moments, whimpering with his head tucked under the man's chin as Philip's cock frotted against his dick, their knots grinding together as his hips began to move almost all on their own, forcing the puppy to hump his father. Feeling his son's smaller shaft throbbing against his, Phil began to thrust against the little boy more aggressively, pinning Sam in place as precum from both of their tips sprayed all over the kid's belly, soaking into the light grey fur until it was fully saturated. Getting dangerously close to disobeying his dad's orders, Sam whined as he hugged the leather-clad canine, trying to pull his nethers away from Phil's incessant humping, getting nowhere as his father only pushed against him twice as hard, forcing the boy to resort to begging, 
"D… daddy, stop! I… I can't… I'm gonna…" 
"Don't you dare cum, or I'll have to punish you~" 
Disregarding the cub's pleading, Philip bucked against the kid's cock even harder than before, both wolves huffing and sweating as he continued without pause, feeling Sam trembling against his chest until finally the pup's entire body went stiff, a warbling howl coming from the little wolf's muzzle as drops of cum showered both of their bellies. Philip rose up off of Sam, leaving the gasping and blushing boy to look down at the strings of cum that he'd splashed all over them both, gulping as he noticed the smirk on his dad's face, 
"Oh, that won't do at all~!" 

Though nervous about what his punishment might be, Sam dutifully waited for it to be doled out onto him, still squirming gently as his dad rose off of him, experiencing the aftershocks of his intense orgasm. Philip rolled to his side and reached under the bed, pulling out a box of toys that he liked to keep close at hand, digging around for a moment before turning back to his son with a large buttplug in hand, bigger than the plug that the cub already had stashed in his tailhole, 
"I think it's about time you graduate to a bigger plug, you've just about outgrown the first one~" 
Gulping anxiously as his dad brought the thick toy right up to his face, spotting his own faint reflection in the shiny pitch black rubber of the plug, Sam took the hefty sex toy into his hands, sitting up with a shiver as he felt the old one in his tailhole. Philip gave the cub an expectant look, telling the boy that he should be getting to work sooner rather than later, getting on all fours and reaching under his tail, letting out a tiny moan as his fingers gripped the base of the toy stuck inside of him. Sam would've preferred the help of his dad's stash of poppers when changing out buttplugs, but he could see from the man's grin that he wouldn't be receiving any kind of assistance, expected to tough it through his punishment all on his own. Taking a deep breath, the puppy began to pull, feeling his tailhole stretching wider and wider as the thickest part of the toy gaped him open, a strained groan echoing through the bedroom as he yanked until the plug finally slipped out with a satisfying pop, providing the boy a split second of immense relief before the sting of his stretched out hole registered properly, the old loads shot inside of him the day before leaking down his thighs.

Grimacing and panting, Sam carefully set the first buttplug aside before reaching for its bigger brother, holding it in his hands for just a moment, staring at the tapering and girthy monster with dread before his dad hurried him along, the man's arms crossed in impatience, 
"Are you going to do it, or do I need to do it?" 
"I… I will…" 
"Good boy~" 
Sam set the plug down onto the bed, rising up on his knees and lowering his rear until he could feel the tip nestled against his gaped and dripping asshole, taking one last deep breath before sitting down on the toy, using all of his weight and momentum to force it inside of himself. With a drawn out grunt, the pup felt the plug stretching his ass even further, thankful that his father's old cum was gushing out and helping to lube up the girthy toy as he whimpered, almost giving into the pain and giving up when the thickest part finally lurched past his clenched pucker, the rest of the toy shooting right up inside of him in the blink of an eye as the kid howled, leaving only the base outside of him. Trembling and gasping, feeling the weight of the sex toy inside of him, Sam laid nearly motionless on the bed for a few seconds before pulling himself up, getting a kiss from his dad as reward. Almost choking on the man's tongue as it slithered down his throat, the cub returned the kiss, clinging to the older wolf as Philip pulled back with a grin, 
"And now, for the punishment~" 
"Th… that wasn't m… my punishment?!" 
"No, that was a reward for barely spilling a drop of my cum when you were sucking me off. Now c'mon, follow me."
Though already exhausted, Sam forced himself out of the bed, waddling behind his dad as the man led him downstairs. 

Struggling to walk straight with the thick toy shoved up his bottom, whining quietly with every step that he took, Sam tried to keep up with his dad, his tail standing up straight. The cub's tail wasn't the only one sticking up towards the ceiling however, with the boy's dick likewise pointing up, hard as ever even after the load he'd busted just moments previously, as the buttplug that was stretching out his hole was large enough to rub up against his prostate, teasing and massaging it with every step that the kid took, forcing him to stay hard even as the throbbing length was starting to become uncomfortably sensitive. Doing his best to focus on best serving his dad rather than the toy embedded in his tailhole, Sam followed his dad into the living room, expecting the man to relax on a sofa and make him put his holes to good use, as he'd gotten very used to doing. Philip however surprised his son by walking straight through the living room and over to the backdoor, opening it up and glancing back towards the unsure cub, nodding towards the backyard as he grinned, 
"Don't keep me waiting~"
With no intention of disobeying his father, Sam limped behind the adult as both naked wolves stepped out into the backyard, only a waist-high wooden fence and a few scattered bushes here and there separating them from neighbours or anyone else who might randomly be strolling past. Gritting his teeth anxiously, the pup fell behind by a few steps, slowed down more by his nerves rather than the aching in his rear, peeking around the seemingly empty yards before taking a careful step off of the back porch, his tail giving a twitch as the grass tickled his bare feet. Sam might not have been a complete stranger to getting lewd in risky situations, he'd blown his dad in the man's car just about daily after all, but most of the risky situations that he'd been in so far had still been fairly safe, with avenues of escape, some anonymity, and a good hiding spot to ease the cub's mind. Out in their backyard however, just about anyone could easily see him or his dad, and also most likely recognise them both, instantly landing the pair into a whole heap of trouble, something that the kid was less than thrilled with. Having to wave for his son to follow him faster once more, Philip walked ahead with a wide smirk on his face, seemingly much less worried about the prospects of being spotted molesting his son, his red rocket thumping up against his belly as he adjusted his leather straps, growling in anticipation as he looked around the backyards. 

Grabbing his son by the shoulder and walking the shy pup over to the fence, Philip hummed as he rubbed his chin and looked at a small shed sitting in the corner of the backyard, 
"Wait here."
The man stepped into the shed, disappearing for a moment before hopping back out with a length of rope in his hands, grinning as he walked over to his kid. Sam already knew what to expect, his eyes scanning the quiet yards anxiously as his dad shoved him against the fence, 
"Hands on the fence~" 
Doing as ordered, the boy put his hands up onto the fence, grabbing onto it and allowing the older wolf tie them both to it, tightening the knots until sure enough that the cub couldn't go anywhere without first being untied by someone else, no matter how much the puppy might have wished otherwise. With his son strapped in place, Phil pushed the canine's head down while simultaneously giving the boy's tail a hard yank, bending the cub over against the fence, leaving Sam's flank completely exposed,
"Better hope you can keep your mouth shut, because some of the neighbours might just peek out of their windows and come out to investigate what's going on otherwise~" 
Shifting his weight around from one foot to the other, Sam waited with bated breath, unsure of what exactly was going on behind him as he tried to prepare for anything he could think of. Suddenly, his dad's hand landed onto his right ass cheek with a hard slap, the beginning of a shrill squeal slipping out from his mouth before the boy was able to suppress it, shaking from head to toe as the man chuckled and gave his ass another smack, watching his plump backside jiggling around as a red imprint of a hand appeared on the tender flank,
"Keep it up, would hate to see what that nice old granny two doors down would say if she saw you tied up and stark naked like this~" 
Biting his tongue and squirming, Sam endured his father's spanking, his muffled whimpers getting louder every time Philip's open hand connected with his butt, the smacks causing his tailhole to flex and squeeze around the buttplug buried in his pucker. 

The wooden fence shook slightly every time Sam received another whack on his flank, gasping as he desperately tried to keep his mouth shut through both the spanking as well as the generous amount of fondling and squeezing sandwiched between the slaps, wriggling against his bindings as the man grabbed onto his cock and milked him like a cow while massaging his sore ass cheeks with the other hand. The teasing quickly caused Philip to regain his vigour, his dick standing stiff for all to see as he parted his son's cheeks, watching the pink ring of the cub's asshole twitching around the base of the buttplug. Hungry to bury his bone and toss his seed into more than just the boy's muzzle, the father gripped the base of the plug and slowly began to work it out with tugs and twists, making the boy softly bleat as he tried to see whether anyone was coming, trying to carefully crane his head over the fence he was tied to while trembling as his tailhole was stretched wide. Popping the buttplug from his son's pucker like uncorking a bottle of champagne, Philip quickly shoved his tip to replace the toy before the boy's asshole could close up, dropping the plug onto the grass as he grabbed hold of the pup's hips, bucking deep inside of the cub. Yipping quietly, Sam was jostled forwards by the force of his dad's thrusting, gasping as the man's girth tore into his tailhole, not stopping even as Phil's knot threatened his pucker. Grunting and ramming forth with no mercy, the older wolf forced his knot inside of the little canine, reaching a hand up towards Sam's muzzle and shoving his fingers into the whimpering puppy's maw as he tied his kid, staying knotted for only a second before yanking his hips back. Letting his dad's fingers gag him, Sam squealed as the man tried to pull out, his legs lifting off of the ground for a moment before his tailhole finally let go of the knot, nearly causing the cub to black out from the pleasure and pain. Philip continued to repeatedly tie and untie his son, panting and grunting like a feral wolf as he went to town on the boy's donut, shivering every time he felt his bulbous knot parting the canine's asshole, managing to last for almost ten minutes before the feel of Sam's tailhole milking him was too much for him to take. Slotting his knot into the trembling pup one last time, the man unleashed his load and filled up his kid, the familiar sensation of his pucker being pumped full of warm cum making Sam howl softly. 

Staying tied to the panting cub for a few tense minutes, stuck in the middle of their backyard, Philip was eventually able to tug himself free from the tight hug of Sam's tailhole, putting the boy's buttplug back in before finally untying the exhausted puppy, walking his kid back inside for an evening of fun and debauchery, leaving a trail of cum on the grass leading from the fence to the backdoor. The two wolves spent the entire rest of the day with one another, only stopping their orgy a few times for naps and some food, falling asleep in one another's arms on the couch as the sun was starting to fall, the man's knot still stuck inside of his son's ass. Shook awake by the sounds of the Sunday morning garbage collection, Philip gave a snort and a groan, lifting his head up from the sofa to see the boy sprawled out on top of him. His cock had gone soft and retreated back into his sheath sometime during the night, leaving Sam's tailhole open to leak the several loads of cum pumped inside of the puppy all over the sofa and them both, the cub's fur dotted with smears of dried jizz, smelling of his father and owner, though the young wolf had never minded the manly musk. Grinning, Phil gently moved his son off of him, able to slip off of the sofa without even waking the cub thanks to the rigorous pounding he'd put the young wolf through the day before, silently sneaking off as the red tip of his dick began to peek out from his fluffy sheath. A few minutes later, the man returned with some goodies in his hands, setting aside a few toys before opening up a bottle of poppers, taking a deep whiff before going to work. In deep sleep, Sam had no idea that his father was looming over him before it was too late, suddenly woken up by a pair of hands prying his muzzle open. Startled, the cub tried to yell and thrash free, pinned belly down as a ring gag was slipped inside of his mouth, fastened in place before he could even grasp what was going on. He felt cold shackles tightening around his wrists as his arms were yanked behind his back, hearing handcuffs clicking shut as his still-sleeping brain tried to catch up to everything that was happening, moaning against the gag. Still kicking and trying to speak, drooling as his teeth dug into the hard rubber of the ring gag holding his maw wide open, the boy was flipped onto his back to see his dad standing there, grinning and dangling a set of particularly intimidating anal beads on his finger,
"Morning~" 

Mumbling incoherently through his ring gag, trying to get into a comfortable position with his arms cuffed behind his back, Sam eyed up the thick set of anal beads that was swinging back and forth in front of his face, each bead larger than the last, a mix of worry and thrill brimming in his chest as his dad smirked. Phil revealed a small remote that he had in his other hand, showing it off to the tied up and gagged cub as he pressed a button on it, causing the beads to suddenly jolt to life, buzzing and wriggling around as an intense vibration travelled through them, 
"I bought a little something extra while I was picking up some more poppers the last time around, just caught my eye~"
The man shut off the vibration, wanting to conserve the batteries since he knew it'd go through some heavy use, setting aside the remote for the time being as he grabbed his son's chin, lowering the dangling set closer to the boy's held open maw, 
"Don't worry though, I won't go in without lube, you'll just have to provide it yourself~"
Blushing as his dad threaded the beads through the ring gag keeping his muzzle open, Sam took in the handful of large balls, feeling the last one sinking deep into his throat as the last and largest ones were making his cheeks bulge out, doing his best to use his tongue and coat the entire set in his slick saliva, hoping he could make the next step as smooth and painless as possible. 

Quickly dipping the beads in his son's mouth, Philip pulled the sex toy out and tossed the pup around again, flipping Sam onto his belly, shoving his head down and his ass up, spreading the kid's ass cheeks and nuzzling the first bead against his abused pucker. With his eyes rolling back and drool seeping onto the couch cushions, the boy moaned as he took in one hard orb after the other, groaning and tensing up every time another one rolled into his tailhole. The first few slipped inside of him with little difficulty, but the last few were starting to give his poor hole some trouble, feeling close to his dad's knot in size as the man rammed them against his clenching asshole, the young wolf's toes curling as his hole slowly opened and swallowed them up as well. With the last bead shoved inside and only the circular handle dangling out from between his buns, just as he thought he might have a moment to catch his breath, Sam noticed his father reaching for the remote from the corner of his eye, mumbling through the ring gag as Philip grinned, clicking the remote,
"I'm sorry, what's that? I can't quite understand you. Turn it up even higher? What a great idea~" 
With the anal beads turned up as high as they'd go, Sam could feel the vibrations travelling through his entire body, causing him to squeal as his tongue lolled out the side of his muzzle, unable to talk or move much with the gag and the handcuffs, watching his dad's erection growing to full size as he shivered helplessly. 

Wriggling around on the sofa, switching between curling up in a fetal position and sticking his legs out as the anal beads buzzed against his prostate, Sam didn't get much time to acclimate to the beads in his tailhole before his dad decided to take advantage of the ring gag, grabbing handcuffs like a convenient handle and yanking the cub up to his knees. Clutching his son's folded over ears, Philip shoved his cock into the boy's face, accidentally giving the pup's cheeks a few pokes with the wet tip of his red rocket before managing to aim his shaft at the opening, sliding his dick right past the little canine's lips and sinking it deep into Sam's maw. Unable to do much besides letting out a muffled moan and pressing his snout deep into his dad's crotch fur, the cub swallowed up the man's throbbing rod, feeling his throat bulging out as his father rammed inside of him, using his tongue to work the bigger wolf's manhood. Unable to fit his knot past the ring gag, and unwilling to waste his morning wood by not knotting the boy, Philip knew he needed to move to the other hole as he rapidly approached his climax, shoving the cub's head into his lap as he reached behind the pup at the same time, snatching the handle of the anal beads and giving it a hard tug. One by one, the beads shot out from Sam's tailhole, each accompanied by a pleasing plop sound as the kid howled against his dad's dick, managing to taste the first rope of cum, still shaking as the man pulled out of his muzzle and shoved him down on the sofa. Quickly lifting up the little canine's tail, trying to waste as little of his seed as he could, Philip jammed his cock into the gaped asshole, punching his knot into the pucker while in the middle of his orgasm, grunting as he unloaded his balls, still humping the cub's ass through the entire climax. 

Staying hilted in his son until he was drained to the last drop, a few of the stray ropes he'd sprayed out while trying to make it into the cub's tailhole soaking into the puppy's fur, Phil huffed and slowly rose up, reaching for the bottle of poppers he'd left sitting right next to the two. Twisting open the top and taking a sniff, the man offered the bottle to the kid as well, shoving the brightly coloured bottle right underneath the softly whimpering cub's nose as he moaned, feeling Sam's asshole slowly loosening with every inhale that the boy was taking, 
"That's it, breathe deep now~" 
Getting lightheaded and feeling like he was in heaven as he took a heavy hit from the bottle, Sam groaned against the ring gag as his dad pulled out of his rear, leaving him leaky once more as the man took off his ring gag and tossed it aside, finally letting him rest his jaw as he panted. He knew he wouldn't have much time to relax however, proven almost immediately right as his father spun his head around, holding the still-throbbing knot and wagging it around with a smirk, 
"I didn't get to knot your maw back there, but this isn't going down anytime soon, so open up~" 
Giddy that he still had the entire Sunday afternoon to mess around with his dad, Sam opened wide, an excited, if not slightly winded, smile on his face as he took Philip's cock back in his muzzle.