Punishments and Privileges

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2 of Ridgewood Elementary Tales The second installment in the Ridgewood Elementary Tales. This time featuring a student who's an unfortunate victim of the perverted principal, and Gareck's son, who gets a little bit of a reward for all his hard work ;)

Update: Special thanks to Aogami for the pic!


Cigar smoke hung in the air as the gruff bear stroked back his long grey hair. He was a bit older but still had that attractive charm about him. He leaned back in the comfortable leather chair, kicking his pants to the floor as a cute little wolf pup reluctantly grabbed onto his thick shaft. The pup shuttered a bit as he felt the warmth of the slick moist pecker, now realizing he wasn't the first detention of the day. "Your sister was in before you," the proud principle said with a hint of contempt, reaching for the back of his student's head before he could back it away, "She was very cooperative...let's hope you're the same, unless you want more of these detentions?"

The pup shuddered a bit, tapping the head of his principle's cock with his tongue, wincing as he did, "N-no Sir, I don't!" As his mouth made content with the cockhead the pup gulped anxiously. The warmth of the bear's cock had a musky aroma that was partly hidden by the inclusion of sweet cherry lube. Even though the musk was enough to give it away, the pup always knew it by the cherry lube. It was like a sick calling card his principle used to make sure the pup knew, the hard bear cock had just been up his sister's ass.

"She's getting good at that" he moaned out, telling his tale to the pup as he forced his shaft up into his little mouth. "Even remembers to thank me now, unlike you!" The cub coughed and gagged, barely able to swallow the thick shaft, let alone breathe with it in his throat. The bear leaned back, letting his length drop back a bit, a long trail of gooey saliva stringing between his junk and the pup's lips. He looked up, eyes watering already from choking on his principle's meat, before wincing at another blast of cigar smoke in his face.

The bear bit back down onto his smoke, using one hand to force the pup's head back down, the other pulling away his pants. He stroked his paw against the cub's rear, scratching hard against the fur before smacking his palm down hard on the boy, "C'mon Jacob, I know you can do better than that!" The boy whimpered, choking down on the thick prick as quickly as he could. The principal groaned and sighed in reaction to the boy's obedience but slapped his palm down hard again nonetheless. "Obedience kid, that's what you gotta learn!"

Smack after smack, the wolf's little rear began to show the rough outline of the bear's palm, the pup clenching as he forced himself not to bite down on the dick in his mouth. "No no no!" he scowled, pushing the boy off his cock and pressing his lips down onto his balls. The wolf groaned in disgust as he wafted in the sweaty musky sack, actually preferring the blast of cigar smoke that hit him suddenly. "Act like you love it, and I'll make things quick!" his voice snarled, watching the wolf take a deep breath before suckling onto the salty firm sack.

The boy placed his mind elsewhere as he played along, tongue lathering the pouch of skin in nervous saliva. "Mmm there's the whore I'd expect," the bear added insult to injury, "I can see the relation between you and Amy now!" Jacob fought back a bitter look, disgusted at the tone the bear bastard used as he said his sister's name.

Fate temporarily saved him as the door suddenly opened, the principal's secretary, a busty young doe with glasses, entering with a long agenda sheet. "How much longer ya gonna be sweets?" she spoke in her Boston dialect, tone sweetened as if all was well as she watched the brutish bear abuse student after student. "Ya got other appointments and if ya keep taking this long ya ain't gonna make it through 'em all!" The bear smiled to her casually, turning his chair to face her, letting the rest of his pants drop to the floor. Jacob's eyes widened as he saw the bear's big ass on its way down, back up as quickly as he could. He had just barely made it out before the bear reached around to grab his head, reeling him back into his backside as he muffled out a stiff "Please god n-"

He could hear the two adults talk, but didn't bother trying to catch any of their words as he rubbed his tongue unenthusiastically against the fat pucker of musky flesh. "Ok," the doe droned out as she turned to leave, "You boys have fun!" Jacob swore in his head, the volume piercing if it were aloud. The principal simply turned around, much to the wolf's relief, hissing out an ungrateful "We will!" He tossed his finished cigar into the ash tray on his desk, twirling his finger in a circle to motion the cub around. Jacob sighed in depressed frustration, reluctantly turning around as he heard the cherry lube gap pop open. He let his tail raise in the air as he begged in his mind, 'Please be over quick!"

Outside, the doe sat at her desk going through her paperwork until a young male boar cleared his throat. She looked over to see him leaning against her desk, wearing a bored frown as he waited to be acknowledged. "Ah," she muttered out indifferently, "Gerick's boy, Ms. Windle said you'd be up here soon" she watched the little snot's mouth curve into a cocky grin that Ms. Windle had told the doe about, the same look his father gave. "Follow me please" she walked to an empty room next to the principle's opening the door and ushering him in. As they both entered she closed the door behind them, locking it behind her before taking off her glasses and unbuttoning her blouse, "Ok, Ms. Windle says you get 'extra credit'...you have ten minutes!"

Jacob howled out back in the principal's office, his arms hugging the table's legs as the bear's thick cock pounded his insides. The principal held the pup's tail up as he smacked painfully into him, grunting out as he felt the tight ring of flesh resist his every thrust. "That's right!" he growled out, humping harder as the wolf whined, "Whimper louder and I'll finisher faster!" Jacob followed his command, not by choice but out of desperation as the large brute dominated his little hole, refusing to add any extra lube.

Next door, the young boar leaned against the door, hands behind his neck in a relaxed state as the naked secretary lathered his junk with saliva. He was fair sized for his age and the doe took appreciative notice, lips suckling at his length heavily as she gently caressed his backside. "Seven minutes left," she spoke between slurps, "...but I'll give ya, mmmf, fifteen if you promise not to tell!"

The boar groaned lustfully as she sucked him off, panting out a gruff "Lips are sealed mam, but wh-why are you holding my ass like that?" The doe stopped for a second looking up at him as she hummed out a "Hmmm..." She grabbed the boy's waist and guided him the other way, spreading his cheeks as she answered, "Some guys like it when gals do this!" The boar let out an almost silent "Oh", breathing heavy as he felt the doe's tongue on his backside. His erection throbbed, the taboo act overwhelmingly satisfying.

"Je-sus lady!" he cheered out as he bounced his bottom, riding her tongue. She 'Mmm'd out on his butt as she worked at the musky button of flesh. "Warm and musky back here boy, definitely mot a dainty boy!" The boar grinned at her words, caring little about how pleasant the act was for her, "Too much flavour for ya babe?" The doe laughed at his player attitude, but made no effort to stop. "Nah, it's fine, I know another guy with a butt like this" she thought about the principal, remembering the night's he would make her 'work late' next door.

In reality, Jacob continued to pant and whine, the principal slapping his waist against the boy's rear as his entire length dove in and out of his tight little rump. "God damnit Jacob you got a tight little end on ya!" he boomed out, stretching the hole painfully by pushing heavily on both cheeks. It practically gaped now, Jacob murmuring insensibly as a long trail of drool poured from his mouth to the carpeted floor. His body was in such a mix of pain and pleasure he had lost sense of his feelings, becoming a mindless slut as he lay down on the office floor.

"Almost there kid, hang tight!" the principal said cheerfully, sitting down with the boy on the floor. He pulled him up back onto his lap and gripped his hair, holding him in place as he bounced his tight little butt against his prick. He smacked several times, ignoring the agonizing cries from Jacob as the hits to his prostate caused his small little shaft to make several squirts. As the cum hit the floor, the bear to emptied his load of seed into the cub's ass, a trail of it pouring out as he tugged his cock out with a loud pop.

His student lay on the floor, panting in a heap as he felt the damp squish of the principal's cum inside him. He reached up with his lips to clean away the tip of the bear's prick, glowing with the joy that his horrible punishment was over. "There, wasn't so bad huh?" the bear faked caring, patting the wolf on the head as he cleaned off his cock. He sat back in his chair and grabbed another cigar, lighting it up as he lazily told Jacob, "Ok go home, and tell your sister I said 'hi'..."

A few resounding thuds echoed on the floor as the doe and boar romped around in the other room, the office staff chuckling out as they heard a thick Boston voice cry out, "Hot damn!" The doe lay on the floor, breasts bouncing as her body was rocked back and forth from the viscous thrusts of the horny student. His entire cock was deep inside her damp sex and he ravaged her with surprising force, the boy in a sex crazed fever.

The doe curled her legs against his back, locking him in place as he worked his young body. "Are you s-s-sure I don't need a condom" he voiced sudden concern, his reply a stiff laugh from the doe. "It's alright, I'm prepared...boss don't use 'em either!" The boar was easily convinced, snapping right back into action. The boar's back tightened as his breath increased, and the doe knew his little body was ready to erupt.

She gripped his ass with her paws, pulling him into her harder with each thrust. He could tell from the brief look in her eyes that she needed this. Somewhere deep down she was unhappy with something, probably some neglectful husband, whose distance must have kept her here, locked into this constant routine of mindless sex. The boar had never been in a girl so wet before, all the girls around the school getting 'a little damp' at most. He could tell she wanted it, wanted it bad!

His legs slapped against her thighs as he ploughed in, his entire length buried in her as gave in to ecstasy. She kept him routed to her as he suddenly began to whimper, warmth filling her insides as he sprayed his young seed. He lay with her for a second, enjoying the gentle scritching of her nails before she pushed him off with a thud, stepping over to her clothes, "Ok go home...oh and make sure you remind your father of his next appointment, I think both Ms. Windle and I should talk to him this time. The boar swallowed hard as he gathered his clothing in a daze, mumbling out a quiet "K..."

The doe calmly left her office when they were both decent again, ushering the boar out before making her way back into the principal's office. She was suddenly speechless as she walked in, seeing the hot poodle, Abby Windle, massaging the principal as he lay against his desk both completely naked. The poodle looked up as she entered, clawing into the principal's back as he nuzzled into her breasts, winking seductively at the doe.

The bear turned to give the doe a grin, puffing the cigar in his mouth as muttered out, "Shouldn't you be working?" The poodle giggled at his statement as she reached down, spreading the bear's ass cheeks. She licked her lips, her gaze returning to the doe as she waited anxiously to watch her. The secretary set her glasses down carefully on the shelf next to her, leaning down on her knees as she nestled into the bear's ass, sighing out, "Right away sir!"