Benny's Brother

Chester shut off his car and glanced over at the clock, leaning back in his seat to relax for a few more minutes, having gotten to the place a little bit earlier than he had planned to. The old donkey glanced out the window, adjusting his glasses as he smirked at the small parking space just off the main road, nestled in the depths of the forest. The spot was a very famous hookup location, having been used for dogging and cruising for at least as long as he had been in town, his weathered jeans already starting to bulge as the equine snorted and thought back to what must've easily been the hundreds of times that he'd been here. The man stroked his growing cock through his jeans, shoving the shaft down one of the pant legs when the tightness was starting to get uncomfortable, a small string of drool running down the corner of his mouth as he checked the time, huffing impatiently. After waiting around for five minutes, Chester decided to head out, hoping his partner had already arrived. He peeked over his shoulder to make sure the small lot was empty before stepping out, scanning the edge of the forest until he spotted the start of a small trail, throwing on a jacket over his tank top and disappearing into the woods. Unlike most of his other meetups at the cruising spot, his partner wasn't looking to get busy at the lot, instead asking if they could get together deeper in the forest and outside of the view of the road. The donkey walked for a couple of minutes, eventually spotting a sliver of a yellow hoodie peeking out from behind some trees, stepping into a tiny clearing to see a 14 year old wolf boy and a feral Australian shepherd waiting for him. Chester smiled at the teen, getting him to blush lightly as he gripped the leash of his dog, studying the old man from head to toe, paying particular attention to the outline of the juicy girth peeking out from the equine's pants,
"Hey there, you're the boy I'm s'posed to be meeting with, right~?" 
The wolf nodded with a mix of apprehension and fervour, unsure of whether to look the donkey in the eyes or to keep his stare at the gently throbbing bulge as his throat ran dry. 

Chester had gotten in contact with the young teen through the same channel he'd often use to meet up with little boys: online chatrooms and forums. His perversions were actually the main reason for the old man to properly learn how to use a computer and all of the oh-so complicated Internet malarkey, but he was very happy with the results of his endeavours, often getting compliments and questions from the other people his age about how he was so good with technology, having to hide his smirk as he made up some lies about his true reasons. The wolf had come across Chester a few weeks back, starting a back and forth chat that quickly intensified from simple dirty talk to swapping pictures, with plans for a meetup coming soon after. The boy hadn't yet gotten his wick wet, though his colourful imagination had left him out of breath and sweaty in his bunk many times, a pack of napkins lying ready at his bedside ever since he reached puberty. Chatting with the donkey had certainly helped him empty his balls into his own hand a dozen times already, but he knew that he wanted more than just some sexting and swapping pics, something that the man quickly picked up on, saving Chester quite a bit of time on trying to manipulate him into meeting up in real life. The wolf was left slightly confused when the equine had asked him for pictures of his faithful hound after casually mentioning the Australian shepherd during one of their chats, becoming even more befuddled when Chester told him to take the dog with him to the meetup, though it did at least give him a very good excuse for why he was going into the forest, his perverted excursion simply seeming like him innocently taking his pooch out for a walk to his parents and anyone who happened to spot him on the way. The wolf tied up the dog's leash around a small tree before turning back to the old donkey, still feeling shy as Chester's perverted eyes ogled at his lithe body, the man slobbering nearly as bad as his canine companion while grunting, 
"Take off those pants, and I'll show you a good time~!" 

The older male watched close as the wolf pulled down his pants and briefs, exposing his furry sheath, half of a canine dick already poking out. Chester was just about to also undress when his phone vibrated in his pocket, rolling his eyes as he pulled it out and realised it was Benjamin's mom who was calling him, pinning the phone between his ear and his shoulder as he continued undoing his belt, 
"Chester here, how can I help?" 
"Hey Chester, this is Christa, Benny's mom."
"Oh, yes, I remember. How's little Benny doing?" 
"He's doing really well, can't stop talking about how much fun he had while you were looking after him. Actually, that's kind of the reason why I'm calling." 
"Oh?" 
The donkey opened his fly and let his cock hang down to his knees, a vibrating rubber cockring already fastened just above his nuts, precum oozing from the tip and soaking into the ground, leaving a thin trail as he took a few steps closer to the obviously impressed and slightly intimidated wolf, still sounding completely innocent on the phone, 
"Yes, my boy had so much fun at your place that you just had to be my first call: I'm in need of a babysitter again next week, you see. Except this time it'd also be his younger brother, Elijah. Is there any chance that you'd be able to handle them both?" 
"Well, I can't make any promises right now, but I believe I should be free for most of the week. I'd be very happy to take in your boys, I'm very confident I could… handle them both~" 
"Oh, you're such a gentleman! I can't believe I'm so lucky to know you, if only everyone could be half as wonderful as you are!" 
Chester chuckled, grabbing his shaft and giving it a slow stroke, squeezing a big glob of pre from his flaring tip as he grinned, staring the teen right in the eyes, 
"What can I say, I just love little kids~" 
"Well, I'll call you back with the specific details a little bit later if that's alright, I'll let you get back to whatever you're up to and stop taking up your time. Thank you again!" 
"My pleasure, Mrs. August~" 
The donkey ended the call and slipped the phone into his pocket, watching as the wolf's erection reached full mast, the teen taking a nervous gulp as his glistening tip rose up,
"Wh… what was the call about?" 
Chester ignored the question, in a hurry to ease the annoying heft weighing his ballsack down. 

With the phone call finally done, Chester stepped next to the cub and grabbed his hand, a ravenous smile on the donkey's face while helping him step out of his pants and underwear, his knot nearly puffed up to its full dimensions. The man gently nudged the teen up against the same tree that the feral dog was tied to, the aussie's playful barks and tail wagging making him smirk as he put a hand around the back of the wolf's neck, bending the boy over. The kid tried to control his rapid breaths while the man spread his legs, both of his arms bracing against the tree, his claws digging into the soft bark as a hand grabbed one of his ass cheeks, pulling them apart. Though he probably didn't need the added lubrication thanks to the waterfall of precum streaming from his tip, Chester still gathered a wad of saliva on his tongue before spitting it into the cub's ass crack, spreading it with his fingers, smearing the slobber up and down against the boy's perfect donut. He could immediately recognise that the hole probably hadn't seen much use besides the occasional fingering, maybe a little bit of toying with some tooth- or hairbrushes as curious teenage sluts like to do, still entirely virginal for all intents and purposes. The wolf whimpered quietly as he was fondled from behind, grinding his teeth against one end of the hoodie string that he had sticking out of his maw, the other end already fraying from his previous nervous gnawing. His whining intensified as the man pushed a thumb into his ass, his knees buckling slightly as a big drop of precum gathered onto his tip, glinting for a second before falling onto the ground, his Australian shepherd sniffing the musky blotch. Chester pulled his thumb out, but quickly replaced it with his girth, sticking the head of his cock between the teen's buns and pushing hard until he felt the tight ring giving in. The donkey slid almost halfway in with just one good thrust, dragging out a sharp yelp from the wolf as he moaned, his spittle spraying down the boy's back as he wrapped his hands around the cub's belly. He pushed deeper, feeling a lump moving around in the canine as he began pounding the kid with passion, making the tree shake while the boy panted, pushing back against his shaft whenever he was ramming into the snug opening. Humping hard, Chester drooled and groaned until he finally came deep inside of the little grey wolf, creaming the teen and glazing the now-gaping donut with his cum as he pulled out, several stripes of white decorating the cub's thighs and ass cheeks as he gripped his length by the base, his balls pulsing as the first half of his load oozed out of the teenager's tailhole. 

The cub gasped and hugged the tree as he felt his filling trickling down the insides of his legs, his stretched asshole winking and squirting one glob after the other while his rock hard dick pointed straight up along his belly, his soft whimpers nearly buried under the sound of his pet lapping up the cum leaking all over the forest floor. He thought that the encounter would be finished with his pucker being packed full, but the donkey had other ideas in mind, still left with plenty of seed to sow and another untouched hole sitting only a single step away. Chester glared down at the Australian shepherd, watching the pup hungrily licking up the contents of his ballsack, tickling the boy while cleaning up the wolf's thighs. The teen staggered to stand up straight, quickly limping to sit down on a log, clutching his erection as he watched the donkey's interest turn to the other canine much to his shock, his eyes going wide as he watched the man probing the dog's flank with a few fingers, 
"Wha… what are you doing?!" 
"I'm gonna fuck your dog, of course~" 
The boy stared in disbelief, but didn't move a muscle to stop the equine as he knelt down behind the feral, lifting the aussie's flank to get a better look at the goods. The dog was panting happily, his wet tip poking from his sheath after sniffing the two male's horny musk, seemingly not minding the fondling of his flank too much, his leash still tied around the tree. Chester drilled both of his thumbs into the feral's tailhole, pulling the tiny hole open as he squealed and whimpered, shuffling around and tugging at his leash. The old man ignored the whining, prying the asshole wide enough to fit his tip inside, still rock solid after tossing a load inside of the owner, grunting and leaning over the dog's back as he felt the cramped hole taking his girth, the tight band of the feral's rim squeezing hard on his shaft. 

The wolf couldn't pull his stare off of his pet being violated, unsure of how he felt about it, almost accidentally grabbing onto his dick and giving it a couple of fast pumps as he hunched over, his legs shaking as he watched the man disappearing inside. Chester forced himself deeper until he bottomed out, reaching under the aussie's belly to grip the red rocket, discovering that the canine was fully hard, 
"Oh, good boy, you're loving this~" 
He glanced over at the cub, seeing the knot grinding against the teen's fingers, the redness of the kid's cheeks nearly matching the shade of both canines' lengths, 
"And it looks like he's not the only one~!" 
Chuckling, the donkey began fucking the dog, the tightness of the tailhole causing the shepherd to be dragged back along the ground a few inches whenever he pulled out, a sharp yip coming from the pooch like a squeaky toy whenever he rammed in. Clutching the feral's knot in one hand and massaging his tip with the other, the man felt his canine member quivering and squirting a sticky load all over the grass and Chester's palm after only a few minutes of rutting, his back arching and his fur standing up as he came. With the unbelievable grip of the dog's asshole, the old man blew his second load of the day, frothing at the mouth as he bucked with every shot, driving his seed deeper into the whimpering aussie, feeling his milkshake sloshing around in the tunnel with every jab. The equine waited for his girth to stop gushing with his sperm, finally coming to a standstill after a few moments of humping against the soft bottom, his cum seeping out and soaking into the dog's fur. Panting, he looked to his side to see the wolf still desperately pawing, grinning as he pulled out and grabbed the dog's tail, turning the feral canine's flank towards the cub, showing off the admirable amount of cum that he had dumped deep inside. The teen moaned at the sight of the creampied hole, howling as he kept kneading himself while letting loose his load, blanketing the ground with thick white ropes. Chester sighed with satisfaction, taking a look at his wristwatch and noticing just how long he had spent fooling around with the eager pair, standing up and wiping off the dirt from his pants, zipping himself up and turning around, leaving the two leaky canines to huff and puff as he waved, 
"If you want more where that came from, you know how to reach me~" 

Through the following few days, Chester and Benjamin's mother continued exchanging the occasional text message as she confirmed the exact dates and times, placing his babysitting gig on the next weekend. Making sure he had his calendar clear for the couple of days, the donkey continued his usual routines through the workdays, the anticipation in him growing with every passing day until Friday finally rolled around. He had been spending the morning on getting ready to welcome the two boys over, cleaning up the mess in his basement dungeon from his last guests, making sure the rest of his house was neat and entirely innocent just in case the woman decided to step inside rather than simply leaving the cubs at his door. The old man was getting fidgety as he kept checking the time, almost getting symptoms of withdrawal, idly massaging his crotch through his jeans as he sat on the couch, two wet spots appearing on the front of his pants: one from the fountain of precum trickling from his dick and the other from the drool he had to keep wiping off his chin. Finally, after what felt like hours of idle time, he heard a knock on the door, sighing as he relaxed himself and tried to tuck his half-chubbed shaft so it'd be as inconspicuous as possible, straightening his shirt and glasses. Walking over, the donkey put on a warm smile on his face just before grabbing the door handle, trying to look as virtuous and gentle as he could, leaning into the character of the neighbourly grandpa that he had carefully cultivated. Opening the door, he was greeted by a trio of foxes, with Benjamin quickly jumping to hug his leg, the mom of the two boys cradling the 2 year old Elijah in her arms,
"Good morning, Chester! And thank you so much once again, I really can't thank you enough for this." 
"Oh, it's no issue whatsoever!" 
The equine took the bundled up toddler into his arms, looking down at the snoozing cub as the woman passed him an envelope with a small stack of cash inside as payment for the babysitting, turning to leave almost as soon as he had grabbed them money, 
"I'm sorry, but I'll have to run to catch my plane, just call me if anything comes up. Mommy loves you both, be nice to mister Chester!" 
The donkey and Benny both waved at the vixen as she jogged back to her car, slipping inside as she drove away. 

With the mother of the siblings out of the picture, Chester was free to drop his facade, his innocent smile replaced with a deviant grin as the older of the foxes giggled and jumped up against him, the boy's tail wagging in excitement, 
"Can we play the fun game again?! I wanna go into the secret place downstairs! Are you gonna put it inside of me again?" 
The equine chuckled and let the kit wrap his hands around his right arm, lifting him off the floor and dangling him a few inches in the air while cradling his younger brother on the other arm, 
"Calm down, you'll get your turn on my cock, just like your adorable little brother will~" 
"Are you gonna play with my bro as well?" 
"Mhm, of course~" 
Benny smiled with barely contained enthusiasm, suddenly turning much more pensive as he dropped off of the man's arm, glancing at the tiny toddler in the equine's arms before turning his gaze to the babysitter's crotch, trying to remember just how big the package hidden underneath was, 
"But wait… isn't it not gonna fit, 'cause Eli is real small, and your peepee is really big?" 
"Don't you worry about that, I'll make it fit~" 
The cub looked at the donkey's diabolical smirk, feeling a twinge of worry for his sibling but quickly brushing it off, thinking that the adult knew much better about these sorts of things than he did after all. Chester looked down at the still napping toddler, gently pulling Elijah's blanket open slightly to get a better peek at him while walking towards the staircase leading down. The tiny kit had blazing red fur unlike his grey brother, taking more after his mother rather than his dad, his tail curled around his legs, shivering softly as the rocking steps of the donkey began stirring him from his sleep. Chester cooed down to the yawning kid, grinning as he clicked on the lights, illuminating the path to his dungeon, 
"Wakey wakey, little slut~! It's high time for you to learn how to make a man very happy~" 

The trio stepped down into the hidden dungeon, flicking on the lights to reveal the large bed blanketed by a soft plastic sheet to help with cleanup and shelves filled with perverted toys. The filming equipment had been tucked away into the corner for this visit, since Chester wanted to take his time and get to properly explore the new boy's every nook and cranny before having to worry about getting good angles of everything for his loyal audience. The ecstatic Benjamin skipped ahead of the man and his little brother, dashing past the two and jumping onto the bed with a giggle, letting the bouncy springs come to a stop before rolling onto his belly, stretching his arms and legs. The donkey laughed, gently setting the waking toddler down on the bed as well, 
"Can't wait to get torn open, huh? Well get out of those clothes and go get my equipment from the closet, and we'll get started~" 
Nodding, Benny hopped up to his feet as quick as he could, simultaneously pulling off his shirt and trying to kick off his pants as he stumbled towards the large closet holding most of the toys, leaving a trail of discarded clothes as he disappeared out back. Chester smirked at the fox's eagerness, understanding perfectly why Benjamin and Trevor were such good friends, snickering for a moment before turning his attention to the tiny kit laying in front of him. The old man peeled back the blanket that Elijah was swaddled in, slowly uncovering more of the adorable baby as he giggled cheerfully, curiously peering around the weird looking room while the equine panted inches from him, a few drops of drool soaking into his fur. With the blanket completely removed, Chester moaned quietly as he rubbed the front of the boy's diaper, undoing his pants as the cub's flustered coos mixed in with the crinkling. The donkey ripped off both pieces of tape holding on the diaper, folding it open and grinning in delight, the kit's teeny sheath and plump ballsack dangling right above his ass, his tailhole flexing gently as he kicked his legs around, enjoying the freedom of being naked. With a relieved huff, Chester let his jeans drop to his ankles, his boxers already nearly soaked through as he pulled them down, his cock twitching at the view in front of him. The man laid the quivering shaft right on top of Eli's belly, interested in seeing how he might react to it, his curious eyes instantly focusing on the leaky tip of the equine girth. Folding both his arms as well as his legs around the large member, the toddler began playing with Chester's manhood, giggling as the pliable pole squirted another dollop of musky precum onto his chest, his own cocklet starting to see sunlight as the warm slab of meat rubbed against his ticklish sheath and balls. 

Getting more horny by the second, the old donkey couldn't take the teasing, the hunger to get much more physical with the boy pushing him to his breaking point as he panted, his tongue hanging down to his chin. He pulled his cock away from the kid's clutches, hunching down over the kit and shoving his face against Elijah's belly, kissing and licking at the giggling toddler. The man grabbed both of the cub's ankles, lifting his feet up above his head while pinning his tail against the bed with the other hand, leaving his flank utterly exposed to the equine's maw. Chester ran his wide tongue over the baby's family jewels a few times, dragging out Eli's little dick as the boy moaned and fidgeted in his hands, getting a taste of the young fox as the boy's cocklet let out a tiny drop of precum. Not content with just sampling Elijah's frank and beans, the donkey dipped his muzzle into the full spread of the kit's ass, using his lips to pull the kid's cheeks open before shoving his tongue into the untouched tailhole waiting within, his drool soaking into the diaper as the toddler whimpered louder than before. The man heard the other canine stepping back into the room, just barely able to pull himself off of the juicy backside for long enough to grunt out a few words to the brother, his glasses fogged up and crooked, 
"Get your mouth in my ass~!"
Benjamin watched the greying equine getting back inside of his sibling's tailhole in a hurry, the man's own asshole waiting for him as he dropped the gear he was hauling onto the ground, crouching down behind the older male and sliding his snout against the already open hole. Elijah gasped and heaved as he was eaten out, a heavy blush on his face, his mouth hanging open as he stared up at the ceiling, his hands grasping at the donkey's ears. Grunting against the toddler's squeezing asshole, Chester pulled his head up again, his frantic gaze staring down at the winking and gaping mess that he had left the little kit's tailhole as he shouted back to Benny, 
"Get the plug in me~!" 
Blindly feeling around for the large buttplug while his entire face was stuffed between the old man's ass, Benjamin finally found the rubber toy, lifting it up to the man's pucker just as he popped his tongue out, his spit making the bulbous plug easily slide in without any resistance, the donkey's trained muscles squeezing his donut around it to keep the toy inside while he grunted like a feral hog in rut. 

Chester tongued the toddler as his cock leaked a pool between his legs, finally pulling back and wiping his lips with a huff, turning to the other fox as he pushed himself to his feet, 
"Get on your brother, let him suck you off while you play with him~"
Accepting happily, Benny jumped onto the bed and got into position on top of his little sibling on all fours, his shaft fully erect as it dangled right above the smaller kit's face. He aimed his puppy dick and gently lowered it into Elijah's maw, getting the toddler to nurse on it as he nuzzled his muzzle between Eli's legs. The baby was mostly hard, his knot still trapped in his sheath, a soft tug letting it pop free as his brother took it inside. While the boys were busy 69-ing one another, Chester pulled off his clothes and grabbed the rest of his gear from the floor, donning the leather straps around his chest and slotting the rubbery cockring around his base. Feeling much more comfortable, the donkey thought that a little bit of background audio might help set the mood even more, taking a detour to the computer nestled in the corner and kicking it on, firing up the projector attached to the ceiling likewise. With the computer's image projected to the wall facing the bed, Chester browsed his private collection for a few minutes until finding exactly the right piece, clicking on it with a smirk. The wall lit up with a video of a fox nearly identical to Benjamin, as well as the kit's older sister, both cubs stark naked and sitting on a bed. The sibling seemed a few years younger than the boy, both slightly nervous as the mother of the pair giggled softly from behind the camera, the view dipping down from just a moment to show her fingers embedded in her pussy as she filmed her kids. The mom cooed out to the pair, 
"Go on, give your sis some love, just like you did with mommy~" 
With slight hesitation, the boy crawled on top of his sister, angling his excited manhood towards her slit with some difficulty, requiring a helping hand from his mother until he was able to push inside. The equine stood up from his computer chair as the sounds of inexperienced moans and perverted giggles filled the dungeon, his shadow cast on the naughty video as he stood at the foot of the bed, stroking himself while watching the brothers sucking each other. 

Chester crawled up onto the bed, slipping behind Benny as he kept pumping his shaft while panting, the cockring keeping him rock hard as his dripping tip left a trail on the bedsheets. The man grabbed Benjamin by the waist, flopping his girth against the cub's backside, accidentally giving the younger canine underneath his target a few soft slaps with it as he tried to finagle his tip between the boy's ass cheeks. Finally finding his target after a few false starts, the donkey moaned as he felt his pole being swallowed up by the kit, Benjamin giving him a muffled whimper as he let the kid's hole stretch over his cock, thrusting in all the way after letting the fox get used to being gaped wide once more. The donkey pulled the boy's buns open as wide as he could, making sure that the toddler underneath the kit's flank could see his girth drilling into the tailhole the whole time. Elijah's eyes were wide open and his face was cloaked in red as he watched his older brother being fucked, still squirming and huffing with his legs wrapping around Benny's neck, shivering every time the older kit's tongue glanced against his cocklet. With his shaft being nursed on by the baby beneath him and the giant equine nailing him from behind, Benjamin did his best to keep sucking on the tiny dick in his maw, humping his crotch against his brother's face as he veered towards the finish line at breakneck speeds. Gripping the toddler's legs, he finally lost all control and squirted his small load into the kid's mouth, Eli drinking down the first few shots of his cream before spitting out his canine member and letting the rest of his load drain down the cub's chest and belly as he moaned. With Benny's hole clenching hard, Chester gritted his teeth and ploughed into the fox one last time, his balls resting on Elijah's forehead as he opened the dam and emptied his heavy sack into the boy's guts. Making sure to squeeze out every last drop he had to give, Chester huffed and looked down with a grin, gripping his base and planting a hand on Benny's ass, slowly unsheathing his cock, using his flared tip to pull out as much of his cum as possible with it. Still smacking his lips from his brother's orgasm, Elijah's face was suddenly buried underneath an avalanche of sticky seed, more pouring down from the older kit's asshole as he wriggled around, nearly his entire head buried underneath a thick layer of steaming hot cum. 

With the equine girth no longer holding him up, Benjamin flopped off of his little brother, rolling to the side with a gasp, panting hard and holding his puffed up belly as the remainder of his creampie gushed out of his asshole, leaving his thighs painted white. Chester likewise took a few deep breaths to steady himself, though he didn't stay still for longer than a few seconds, a perverted smirk overtaking his exhausted look as he grabbed onto the utterly drenched toddler lying in front of him, turning the cub around so that the boy's hole was facing him. Eli was still coughing and licking at his muzzle as a result of the sticky surprise he had received, peeking over his belly as he felt the man lifting up his legs, a finger tickling his taint as it tried to find his asscrack. With one hand keeping the writhing baby's ankles together and up, Chester swiped up a glob of his cum from Elijah's belly, using it as makeshift lube as he stuck a finger into the toddler's tailhole, having to wriggle and twist his digit for some time while pushing hard until the cub's tight ass finally let it inside. Benjamin woke up from his tired daze as he heard his little sibling crying out in pain, quickly jumping up to see Eli squealing and groaning as the old man's thick finger slid deeper into the toddler's flank. Worried about his brother's wellbeing, the boy quickly crawled over to Elijah, trying desperately to soothe the whimpering kit, petting the young fox's soggy chest, 
"Shhh… it'll feel really good! Don't worry!" 
Getting slightly nervous as the cub's crying only intensified as Chester added another finger into the mix, Benjamin tried the last way he could think of to get the boy to quiet down, leaning over Eli and wrapping his lips around the toddler's muzzle, mimicking the way that the old donkey kissed him as he slipped his tongue into the screaming baby's throat, managing to muffle Elijah's squeaks.

Getting the toddler open enough that he could eventually fit a third and even a fourth finger inside of the boy, Chester was starting to get erect again, most of his mottled length still slimy and slippery from the other fox's hole. Pulling his fingers out, he grabbed Eli and lifted the cub up against his belly, hovering the whining and sniffling kit right over his manhood as he snorted down to the brother, his tail flicking against the bed, 
"Get me inside of the slut, would'ya~" 
Benny stared the huge cock resting between the baby's thighs, only now realising how small his sibling truly was, a bit hesitant as he grabbed the man's tip and guided it between his brother's cheeks, sliding it right against waiting hole, the toddler's pucker still slightly red and puffy from the stretching exercises. With the help of the older canine, Chester slowly and carefully worked his half-flared dick into the tiny kit, licking and kissing Elijah the whole time as he moaned furiously, his drool running down the boy's front as the cub squealed. The donkey kept grinding and humping up into the toddler's tailhole, feeling the tiny hole stretching out little by little while Eli's bawling worsened, his hands squeezing the fox's small body as he tried not to let himself flare up all the way before getting in. Eventually, after several minutes of sweating and moaning, the old equine managed to pull the cub down onto his cock, spearing his shaft nearly halfway into the toddler as Elijah screamed and broke down in tears, his girth instantly flaring up full as the boy twitched around his sensitive member, locking him in tight as he held his breath, feeling his balls tensing up until a giant wave of cum flooded the virgin boy. Knowing he had no hope of moving even an inch until his flare went down, Chester laid the whimpering kit onto the bed, letting Eli squirm and milk him dry as he leaned back in bliss, massaging the little kit's bulging belly as it filled with his seed. Benjamin sat on the side and watched his sobbing brother, rather obviously worried, the donkey noticing his concern and alleviating his unease by grinning and pinching the toddler's rock hard cocklet, Elijah's high pitched howls intensifying as Chester rolled the miniature knot between two fingers, 
"Don't worry, he's young and real flexible, he's not gonna get hurt. He'll get used to it, the next time around he'll be begging to be gaped twice as wide~" 

Huffing and puffing as he felt his balls draining into the toddler, Chester relaxed and let his shoulders slouch, his tail twitching with every squeeze the tailhole gave him. Elijah's weeping had calmed down to an occasional whine and sob as he got more accustomed to being skewered by an equine shaft, laying down completely limp with his eyes closed, his chest heaving up and down, only occasionally squirming around as the pressure of the load inside of him grew to uncomfortable levels. The donkey gave his cock a careful tug, feeling it starting to come loose as his flare slowly deflated, turning to the older sibling with a grin, 
"Go and get me another plug, I want your brother to keep my cum in his ass for a bit longer~"
Benny scampered to the closet, fetching a buttplug a few sizes down from the one that the donkey had up his ass, looking around for a moment before finding a perfect one from the rather large collection of different toys and other deviant playthings. The boy grabbed a bright red rubber plug almost resembling a dog's chew toy, a series of growing balls linked by a stiff rod, something of a mixture between a buttplug and anal beads. Benjamin brought the toy over, handing it to the donkey before curling back around his little brother, comforting the kit as his own tail end still continued dribbling. 

Chester held the plug at the ready as he yanked his girth out, grunting in delight while Eli yelped sharply, a deluge of cum pouring from the boy's abused hole. He quickly shoved the plug into the tailhole to stem the flow, the smallest first few beads of the toy flying in without even touching the rim of the cub's gaped hole, only the largest and final bead managing to seal in his sperm while Elijah whimpered softly. Letting out a content sigh, the old man wiped his forehead, as he looked down at the messy state he had left the two siblings in, able to admire his handiwork only for a second before he heard his phone vibrating. Bending over to simultaneously grab his phone from the pocket of his pants as well as to pop out the buttplug from his own asshole, Chester casually motioned towards Benny while focusing on his phone, 
"Get on your back and open your mouth."
He clambered up onto the bed, squatting down over the cub and shoving his hole against Benjamin's snout, pushing the boy's entire muzzle deep inside of his pucker as he opened up the message, moaning softly while Benny lapped at his flank. Letting his half-hard shaft drip onto the fox's belly, the donkey read the text he'd gotten from the wolf he had met a week ago, 
"I kinda wanna meet up again."
"I could arrange that." 
Chester glanced over at the panting toddler filled with his cum and down at the kit rimming him, imaging the pair both stuffed with feral cock as he chuckled, quickly typing a follow-up to his last text message, 
"But you're gonna have to bring your dog along again."