The Tail End of the Night

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#44 of Ridgewood Elementary Tales

Here is the final of the three stories detailing Ridgewood's parent/teacher night. This one is M/M so all the boy and men fans out there rejoice!! There is so much smutty awesomeness going on in this one, all male teacher on male cub so hopefully that's up your alley.

The middle section is cut off a little short but I figured the nature of the flashback would make it so, that and adding the last part would seem redundant in relation to the other two sections.

Enjoy :)

Kevin belongs to Kevinsnowpaw

Lance belongs to VerbMyNoun

Thumbnail by the awesome DizziMorhlis, made from the image based on this story here: https://www.sofurry.com/view/698916


Mr. Thibault walked calmly down the hallway as he awaited the start of the annual parent/teacher night. He had no plans until the parent's arrivals, so he thought it best to get a little stroll in. He yawned as he looked at his wrist watch, noting the remaining time before the whole event began. He was about to head back to his classroom until a sudden tapping grabbed his attention.

His ears perked to the sudden sound as it rasped out again, like little fingers tapping from the inside of the nearby maintenance closet. The serval rolled his eyes as he walked over to the small room, the school's janitor notorious for his occasional forgetfulness. "Ok get out of there!" he said sternly as he walked in, about to grab whichever student had come in early to cause him trouble.

As stepped in, the fur on his back shot immediately up, the teacher gulping as a small white paw shut the door behind him, locking it. "Mr. Thibault... I-I've been thinking about you..." the marble fox whispered as he leaned against the serval's crotch, the young cub entirely naked, his clothing strewn about the shelves above him. "I know, this... could get you in a lot of trouble," Aiden continued as he pulled the serval's jean zipper down, "...but I promise..." he slipped out the feline's hard cock, gasping as he saw just how big it was.

He sucked on the head tip for a moment, lathering it in saliva as the adult just moaned, still overwhelmed but clearly turned on, "I promise I won't tell anyone," Aiden continued, "...an-and you can do whatever you want with me!"

The serval looked around anxiously as he tried to skim his memories, unable to recall rather the young fox was on Isaac's 'approved list' or not. After a few more sucks however, he gave up, holding the back of the cub's neck gently as he thrust into the warm muzzle, "Ok kid," he groaned, pulling his shirt off, "You got thirty minutes... make it count!"

Aiden sighed lustfully as the serval's length slid down his muzzle, filling up a good amount of his throat. The marble fox cub couldn't have been happier, in his own form of heaven as he knelled down on his knees in the janitor's closet. He would work take turns between pushing his throat down over the shaft and letting it drop it to give it soft kisses, his lips literally worshiping that cock of the man he fancied.

Lance leaned back against one of the closet's shelves as he gasped and groaned, the cub showing such expertise despite his lack of experience. He didn't know how the boy had been practicing but the look in his eyes told him that the boy had prepared it precisely for him. "Damn, that's good kid!" the serval sighed as he reached down, his paw stroking the cub's hair.

The marble fox cooed softly in return, letting the teacher's cock bounce out over his forehead, spraying a few shots of pre onto his forehead as he sucked on the teacher's firm, somewhat musky balls. "I've wanted this for a long time" the fox spoke with a bashful chuckle, sliding his tongue up and down between the serval's balls and shaft.

"Heh, I can see that!" Lance said as he scritched the fox's ears, "Does that mean I don't have to limit my enjoyment?" His eye raised a little curiously, fingers snaking under the cub's tail to prod at his pucker.

The fox smiled as he raised his feet a little, letting the serval's fingers slide in a little as he sucked the feline's cockhead, "I'm all yours!"

"Alright cutie," the teacher grinned as he pushed his fingers in deeper, wiggling them around, "Let's get you stretched out!" The cub grunted as he felt the slight invading sting in his rear, the lack of lube not too much of an issue yet. His saliva was already dripping to the floor under the pair, the marble fox still swallowing down the serval's length needily. "Mmm, you're really good at that," Lance moaned as he thrust up into the student's mouth, "Can't wait to get in here!" As he spoke he kept sliding his fingers around in the tight warmth of the cub butt.

"L-Lance..." the fox said, looking away slightly, "C-can I kiss you?"

The serval looked down at the boy as he looked so charming and unassuming, chuckling to himself as he lowered himself a little. "Sure kid!" he said as he pressed his lips to the fox's, their tongues meeting in a smooth, sensual slide as his fingers kept working their magic on the boy's backside.

Aiden's heart hammered in his chest as he rubbed his smaller tongue affectionately against the adult's larger one, their lips pressed against one another as he felt the dull, fullness in his rear, like he had practiced feeling so many times on his own. He leaned into the teacher, hugging him with both arms as the kissed continued, his breath staggered and panting as their embrace broke. "Th-that was nice..." Aiden blushed, crying out again as the serval attempted to sneak in a third finger. "H-here," he stuttered as he reached behind one of the boxes on the nearby shelves, revealing a bottle of 'EZ-Glide', "I brought this."

Lance grinned as he saw the little bottle of lube the cunning fox had brought with him, "Eager is definitely an understatement with you huh?" As he snatched the bottle from his companion, a thought occurred to him. "Tell ya what, ummm..."

"Aiden" the fox giggled, realizing all this passion had occurred before they had even been on a first name basis.

"Lance," the serval offered before continuing, suddenly laying down on the closet floor, "Sit up here!" he offered as he patted his chest. The cub followed his instructions, carefully resting his legs on the adult's chest as he heard the cap to his lube bottle flick open and the squishing sound of some of its contents drain out. He let out a loud whining pant as three cool, slick digits probed into his rear, spreading him open good and wide as the serval's lips wrapped around the boy's modest cubhood.

Aiden whimpered and moaned as he felt the serval's tongue rub against his shaft, the adult easily fitting his entire length down his muzzle, even getting some of his little knot in. At the same time, the spreading tingles of his backside were no longer painful, instead just tickling, the deeper they got the better he felt. The young marble fox's body tensed up as a strong flutter filled his body, the teacher stopping just in time to allow the cub only a small cum shot, his young knot barely satisfied.

He groaned out as he swallowed the salty, youthful release, his fingers slipping out of the cub's rear. Just as the fox had begun to shake and shiver, Lance gripped his cock, pressing it against the boy's pucker, teasingly poking the tip in, "So Aiden... how far do you want to take this?"

The marble fox looked back at the teacher with almost a glare, the teasing tickle of his cockhead a cruel form of torture. A more dominant side seemed to well up in him as he was denied more of the desirable feline's manhood, and he leaned his smaller body back, pushing his tush down, until his prepped pucker swallowed a good half of the offered shaft. "I'm taking this all the way Lance, don't think you're getting away with any less!"

The serval was already panting himself, as he felt the intense tight warmth that gripped his cock, his hips bucking gently as he plunged more of himself into the eagerly accepting rump, "God Aiden, y-you feel wonderful!" He looked up, mesmerised as the cub had begun to ride his shaft, nearly every inch of him swallowed up by the bouncing pup, "Ok Aiden, brace yourself!"

Before the fox could contemplate the nature of the teacher's words he had raised the boy up a bit, his hips thrashing as he slammed his cock down deep, the head of his prick punching the fox's prostate. Aiden could barely breathe as the dull, tense feeling in his bowels overtook him, a pleasure unlike any he had ever felt causing his mind to go numb. "H-harder Lance, t-ahh! Take me!"

The serval grunted and groaned as he continually buried himself into the boy's backside, his thrusts growing faster and harder as his partner had begged for. He reached suddenly for the back of the boy's head, doing all the work to push their muzzles together, his tongue invading the boy's mouth as they shared a sloppy, feral kiss. Lance could feel Aiden's heart beating frantically as he kissed him, his cock still slamming into the boy's prostate.

The serval coaxed the boy to stand back up as their muzzles parted, his hard cock flopping out, leaving him a momentary view of the overly stretched hole. "Lean on that shelf!" the teacher commanded, the fox eagerly obeying, holding his rump out as he gripped the shelf beside him. The serval aimed his cock carefully back into place, hot-dogging the boy's tailcheeks a few times before finally sinking back into the warmth of his ass. Both males sighed out in unison as everything just felt right again, Lance's paws holding Aiden's hips as he bucked wildly into the cub's tight rear.

"Mmmf-harder!" Aiden moaned out as the serval growled out behind him, his thrusts became wild lunges as he stopped holding back, realizing the young marble fox could easily stand all of what he had to offer.

The feeling engulfing his manhood and the appearance of the adorable pup in ecstasy was far too much for Lance and he soon groaned out, "G-gonna cum, want me to pull out?"

Aiden panted as he began to paw himself off, body tightening as he whimpered, "F-fuck no!" The serval couldn't help but laugh as he gave one final, heavy thud into the boy's backside, his spines gripping the canine's inner flesh tightly as the throbbing tip fired volleys of thick seed. Aiden winced as he felt the harsh stinging of the feline's barbs, able to push past it as he stroked out his own cumshot, catching it in his palm. It took several agonizing minutes until the serval's cock finally simmered down, releasing its hold on the young fox.

Aiden sort of staggered before falling back into the teacher's arm, Lance gently rubbing the boy's forehead as he whispered, "Damn kid, I'm impressed!" Aiden smiled weakly as he caught his breath, slowly getting back to his own two feet without support. As his orgasm subsided, he had become shy again, falling silent as he looked away with a slight blush. Lance had already begun to dress himself again, and was clearly muttering to himself as he looked at the time.

"I-I umm, guess you should get going to your parent/teacher thing..." the marble fox said shyly.

"Yeah," the serval replied, patting the cub on the head as he turned to leave, "Tell ya what though... why don't you stop by my classroom sometime?"

The fox looked up with a rather cheerful smile as he seemed to bounce on the balls of his feet, "Really, you mean it?!"

The teacher laughed as he nodded his head, "You make a very convincing first impression," as he left he gave the student one last parting statement, "Oh, and next time, I'll pick the location... some place a little nicer for us."

As the door closed Aiden lay in a warm heap, his body and mind in triumphant afterglow. A grin remained on his muzzle as he rubbed his belly, slightly bloated as his rear ached rom the onslaught. All was well in Aiden's world as he let his body recover from the best experience of his life.

...

Later in the night, Chelsea and Kevin had reunited and were roaming the halls to find their favourite sheep. They had already roamed what seemed like half the school aimlessly with no signs of her. They decided to stop by the school's office, hoping Isaac was on a short break on the off chance he had seen her.

The pair entered the office quietly, in case there were still visitors inside, Chelsea taking the lead to knock on her father's office door. She was greeted with a tired but warm smile as her father looked down at her, "Hey there sweetie, what brings you back here?"

Chelsea couldn't help but smile at her father's warm tone, "Just looking for Allie, have you seen her?"

"Nope, sorry dear," the older bear said as he looked over to Kevin, "Isn't bunny boy enough to keep you occupied though?"

Chelsea blushed as her father made his vague sexual comment, "Oh shut up dad!"

He chuckled as he kept talking with his daughter, Kevin's attention however drifting as the vague insinuation brought up memories from just weeks ago.

...

Kevin let out a low whimper as he lay against the carpeted floor of his principal's office, the gruff but passionate bear sliding his fingers along the inside of the rabbit's muzzle. His free paw had roamed down over the cub's erection, both males already having stripped down. "I see my girls taught you well, didn't they?" he asked as he removed his fingers from the rabbit's mouth, sliding them over the boy's pucker, before plunging the two digits in.

Kevin shook a little as he was continually felt up, the little sting from the bear's probing fingers causing him to grip the adult's arm in a supportive hug, "Ahh, mhmm, th-they did!"

Isaac grinned triumphantly as he watched the boy melt into his embrace, the bear shifting a bit so his cock could lay over the rabbit's cheek, "Have you ever wanted to suck a cock before Kevin?"

The little white rabbit nodded enthusiastically as he looked over the sizable shaft, his tongue affectionately sliding into the bear's foreskin to drag along the inside of his length. "It t-tastes really good Mr. Berkeley," Kevin said gently as he moved his muzzle down, fitting a couple inches of the hard cock into his mouth, "I th-think I really do like boys too!"

"Mmm," the principal groaned as he pushed a little more of his shaft down into the boy's throat, the rabbit's eyes looking up excitedly as he did his best to fight the odd gag reflex, "You wanna be a good little cock sucker for your principal Kevin?"

He could hear little gulps sound out under him as the rabbit swallowed down some of the bear's precum, the cub panting for breath when Isaac removed his shaft, a long line of saliva connecting his lips to the principal's cockhead. "I wanna be a good cock slut for you!" the rabbit groaned out obediently, using the words Chelsea had told him to. He remembered being curled up in her lap, pleasuring her orally as she explained all the ways to make her father happy.

All that information had been made useful now as he lay under his principal, the strong natured bear holding the cub's cheeks as he guided his length in and out of the rabbit's warm muzzle. Kevin sighed out in an anxious whisper as he was pushed back, Isaac burying his fingers deep inside the boy's rear. His young cock throbbed as a little bit of precum squirt out, the rabbit getting harder with each rough push into his backside. "How does that feel Kevin?" the bear asked in his deep, powerful voice.

"I-it feels really good!" Kevin murmured out, squeaking suddenly as the bear's tongue trailed over his shaft, and up his chest to give his neck a little nip. "Mr. B-Berkley..." the bunny boy whimpered as the bear's tongue slide back down, his lips sucking on the cub's shaft for a moment.

"Please," his principal said as he got back up turning the other way to raise his rump up, "Call me Isaac... you know what comes next, right Kevin?"

The rabbit gulped as he nodded anxiously, already having been warned of this by Chelsea. "Uh... Uh-huh..." Kevin stuttered as he crawled up to the presented rump, his little nose sniffing at its musky scent. He wasn't totally taken aback by it, and his cock was still standing at attention.

After a moment's hesitation, Isaac spread his cheeks apart, showing off his pucker as he growled, "Well, what are you waiting for then?!" The young rabbit let out the slightest little meep as he was rushed on by his principal, his lips slowly pressing against the warmth of the bear's backside. He let his tongue slowly slide against the ripple of flesh, allowing his taste buds time to adjust to the new flavour. He got used to it quite quickly and began to lap at a faster pace, finally working up enough courage to probe his tongue into the tender hole.

"Mmm that's nice!" Isaac moaned out as he felt the smooth dampness of the rabbit's tongue plunge into him. Kevin kept pushing his tongue deeper into the bear's backside as he groaned out for him, a smooth "There we go!" escaping his lips. The rabbit sucked and slurped at the tight hole, circling his tongue around until it began to sink in deeper.

"Y'know I taught Chelsea how to do that," his principal murmured out, reaching back to push the rabbit's muzzle deeper, "...and I like it nice and deep!" Kevin pushed his tongue as far as it could go, forced to breathe through his nose as he pleased his principal. He reached his paws forward, stroking the bear's hard cock that lay over his chest. "Mmm, that's nice!" Isaac growled, reaching carefully to push his fingers back up the cub's tailhole. Kevin spread his legs to allow the invading paw easier access, Isaac's other paw reaching down to stroke his modest cubhood.

"Let's keep looking!" Chelsea called out suddenly, Kevin jumping with a little twinge of shock as his friend snapped him back into reality. He nodded to Isaac with a little blush as the bear cub pulled his arm, the two shuffling off to continue their sheep hunt.

...

As the night winded down, Isaac was in his office, a low comfortable murmur escaping his lips as he made out with the middle aged canine, his light coloured fur an almost pale purple, and his body firm, well taken care of, lined with masculine tattoos. Small sucks and slurps sounded out underneath as the canine's son Bradley held both their cocks, moving his muzzle back and forth between the two. Jason leaned into Isaac's ear whispering to him, "Missed you stud, Bradley and I have been thinking of you quite a lot!"

"Mmm, have you?" he replied in a groan, pushing his muzzle against the canine's in a kiss, while at the same time Bradley worked his tongue into the bear's foreskin. Bradley sighed comfortably as he worked the shaft deeper into his muzzle, suckling tightly onto the musky shaft.

Jason let out a loving murmur as their kiss broke, fingers caressing the bear's back, "Mmm, that was nice stud," his finger slid down suddenly, pressing gently against the bear's warm pucker, "Mind if I put my tongue elsewhere?"

Isaac murred out as he stood a bit straighter, the younger cub still working his cock with his muzzle. "Be my guest!" he growled in a sultry tone, gripping Bradley's shoulders as the older canine knelled down on the floor behind the bear. He sniffed at the tight ring of flesh in front of him, groaning out as he sampled the clean yet musky details of his scent. His arms wrapped around the bear's waste as he buried himself face first, nestling into the furry cheeks.

Slowly he began to slide his tongue around the tight flesh, pushing inward with expert precision. Isaac grunted as he felt the slick wetness sliding inside him, the canine clearly knowing what he was doing. "God you have a nice ass!" Jason moaned out in between licks, his lips pressing tightly against the bear's tight rear.

At the same time Bradley had swallowed down most of Isaac's shaft, gulping down precum and slurping at the shaft's surface, his eyes watering by the sheer size. "I need to spend more time with you two!" Isaac said, gently growling in pleasure as more salty pre slid out into the boy's mouth.

Jason was delicate and precise as he pushed his tongue up into the bear's ass, at the same time his son working his muzzle down almost too well on Isaac's cock. Isaac grunted as he gripped the wall, a menacing grin filling his face as he shot a partial load of cum down the pup's throat, "Damn kiddo, almost made me blow it all!"

Jason stopped quite suddenly as he withdrew from the bear's rear, panting and groaning as spurts of pre cum hit his legs, his knot thick and aching. "Fuck, you're telling me, if I spend any more time on your backside I'm gonna blow!" Jason sighed, wiping sweat from his forehead.

"Here daddy!" Bradley called out to his father, stepping over to him and kneeling down, he sucked on the first few inches of his father's aching shaft, just enough so a small amount of his cum buildup could shoot down the boy's throat.

"Yeah, that's it kiddo, ease up the pressure!" Jason moaned. As the two shared a little family time, Isaac stepped back over to his desk, grabbing a bottle of personal lubricant before returning.

As Bradley slurped down on his father's shaft the bear returned, already squirting a glob of lube onto his paws. The cub suddenly shuddered as the cool liquid made contact with his rear, Isaac gently slipping his fingers over the tight little tailhole. Bradley squeezed his father's legs with his paws, cuddling up to him for support as the bear's fingers slid in with a gentle little sting. "Shhh, come on Bradley, be a good boy and relax your asshole for us" his father whispered, petting his son's cheeks as he kept gulping down his hard length.

Isaac growled out a deep moan as he finally slid two fingers deep into the boy's butt, the soft warm flesh hugging the smooth digits tightly. At the same time Isaac reached forward with his dry paw, squeezing the boy's balls gently as he saw Jason reached forward, stroking his son's cock. "You like that Bradley?" Isaac asked in a low hiss, his fingers thrusting hard against the boy's prostate.

"Yeah kiddo," Jason moaned as he watched his son suckle on his cocktip, pre spraying over his tongue, "You want us to fuck you, don't you boy?!"

Isaac's paw left the cub's balls as he smacked his right butt cheek firmly, the cub whimpering a little before gasping as a third finger was slid into his pucker. He lifted his leg up as if to pee, letting all three fingers sink as deep as they could. The faster Isaac forced his fingers in, the more slobber would fall from the boy's lips onto his father's lap, the look on the cub's face one of true happiness as constant pre leaked from his smaller cock.

Jason laughed as he got up a bit, his cock dropping from his son's muzzle as he reached to pinch both the boy's nipples, he fell to his side in submission, tears welling up in his little eyes as his chubby stomach shook, the bear literally finger fucking him. Bradley cried out in a high yip as he was engulfed in somewhat painful stimulation, howling out "Ahh, Please, f-fuck me, fuck me, fuck me!"

He was quieted suddenly by his father's lips, Jason burying his tongue into his son's muzzle as Isaac slid his fingers back out, quickly opening the bottle again to lather his prick in lube. The incestual pair kept kissing, even as Isaac began to shove the first inch of his stiff prick into the overly inviting backside. Bradley fell back into a missionary position as the bear slid a good half of his length in, his young body stinging, shaking, and tingling all at once. He moaned out with a tone of lust and need as his father moved his lips away, the older canine turning to lift his tail up before kneeling back down in a squat, "So proud of my little slut, eat daddy's ass!"

The puppy murmured out an unheard response as his father's warm, somewhat musky rear hovered over him. Leaning up just a little so he could run his tongue along it. Its scent was clean but manly, each detail intimate and strong, lighting the puppy's passions ablaze. His little licks quickly became furious laps as slowly he edged his tongue up into his father's ass, sliding it around as it probed in and out.

In tandem with Jason's actions, Isaac had begun to slide in and out of the pup's tight ass, holding the boy by both legs as he buried himself in deep. He had been with Bradley multiple times and knew the cub's limits. Despite how deep and hard the bear was going, the cub experienced no pain or trauma, the silent rhythms of his body allowing the cock inside him as much as his body would tolerate.

Bradley smooched and slobbered at his father's pucker as he took pound after pound from the principal's prick, his own cock aching hard as he serviced the two older men. "God you're so good at that!" Jason moaned as his son sensually slid his tongue along his backside, the damp tickle keeping him hard and enticed.

The wonderful display and constant warm, tightness around his shaft pushed Isaac off the edge, his paws gripping the boy as he roared out, "Get ready Bradley!" The boy nodded as he continued giving his dad's rump gentle kisses, a squeak escaping him as Isaac slammed in, bursting a heavy load of cum inside him. Jason go to his feet as he heard Isaac's grunting, all the telltale signs of a cumshot easily audible. As he got up, his son gave his balls a quick lick, clearly sad his rim time was over.

Bradley flopped over onto his stomach panting, poetically posed in a doggy-style position as he reeled from the orgasmic twinges in his body. As his father crept towards him, he reached back with both paws, spreading his cheeks apart so his cum dripping tailhole was on display. Jason growled a deep murr as he gripped his hard cock, rubbing it against the pool of bear cum until it was slick and sticky, moaning as he pushed the tip into his son's abused hole, "God I love sloppy seconds!"

Bradley simply murmured inaudibly as he let his father slide into him, sighing out happily as he felt the canine's knot smack against his aching hole, the older canine thrusting wildly into his son. Jason grinned to Isaac as he rolled on over in his desk chair, sitting beside the pair as he enjoyed the show. Jason leaned over as he kept fucking his pup, giving the bear's balls a firm suck, "Did my boy do a good job for you Mr. Berkley?"

"He did!" the bear smiled as he pet the dog's chin.

The canine's grin was wider as he confirmed how pleased the boy's principal was, his right leg raising up as he humped his son harder. His breath was tight and staggered as he hammered his cock wildly against his son's prostate, a gleam in his eyes as he growled out, "Ready for daddy's knot?!"

The pup cried out as his father thrust into him so relentlessly, the thick bulb of flesh pressing against his plump ass, "I-I'm ready dad!" He whimpered out again as his father nipped his ear, tongue sliding down the side of his face before he began to suck on the boy's neck. Isaac grumbled out an appreciated mumble as he watched the father take his son with such passion, the dynamic reminding him of himself with his own daughter.

It didn't take long for the older canine to deliver as promised, a few more smacks all it took to hammer his orgasm home, a few shots of cum joining the pool of bear seed just before the knot forced its way in. Bradley cried out as his pucker was stretched uncomfortably wide, a rough sting emanating from his rear as a dull fullness welled up in his gut. "God you're tight boy!" Jason spoke as he sucked on the pup's neck, awkwardly positioning his legs so he could face the bear, the dog's facing away from each other as Jason fully locked in.

Isaac grinned as he looked down at the father in his afterglow, stepping over to scritch behind his ears. "Mmm y'know Mr. Berkley," Jason said as he kissed the bear's finger, "You should really take my ass sometime... I don't usually submit to anyone, but a fine specimen such as yourself..."

"Shh!" Isaac said as he reached his paws back, fingering the older canine's pucker as he pulled on his knot, causing Bradley to whine out uncomfortably until a loud pop and squishing sound of escaping cum told him that the boy was free. "My wife will be back soon, and so will my daughter... now you two run along home and treat each other really good, then tomorrow I'll give you another treat Bradley," the boy nodded, "...and next time you are free Mr. Oaks, I'll eat your son's ass while I tear yours in half!"

Jason shivered as he took in the principal's words, the parent silently getting to his feet as he gather his clothes. Isaac looked away as he enjoyed the triumph of such a dominate stance, his ears flickering as he heard Jason whisper, the statement to his son a fitting end to the night, "Be good and listen to your principal Bradley, he's a good man, if he ever needs you to do anything for him, you do it!"

Bradley giggled as he kissed his father on the lips, "As if you could stop me!"