A Stern Stuffing - Commission for Sparkx Falcon

Story by Stinkdog on SoFurry

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#9 of Story Commissions

The first in my round of commissions set in Port Crow, this story features a lot of anal action. Hope you horndogs enjoy!

Not only did Sparkx Falcon ( https://www.furaffinity.net/user/veem0n ) commission the story, he also commissioned SpelunkerSal for the artwork!

Also, Terribadger lent me his editing assistance once again.


A harbor bell rang out over the din of morning work on the docks of Port Crow. The sharp clanging warned dock workers of an approaching ship that would need to be moored to the wharf and unloaded. Jay Bayson, a burly and imposing humpback whale, released the bell rope as he saw his workers scurrying to meet the incoming vessel. He sat back down at his table and began preparing a cargo manifest for the ship. Every vessel that arrived in Port Crow had to be properly accounted for and it was the wharf manager's job to ensure that cargo was sent where it was supposed to be. Jay had held the position for several years now, and he enjoyed it despite the occasional hiccup.

The whale tapped his gut idly as his feather quill scratched over the parchment on his table. As he finished drafting the manifest, he heard a commotion outside. It seemed like another "hiccup" was brewing even now. Jaw stood quickly and rushed out the door of his small office. The incoming ship was tilted to the left, drifting away from the clamouring workers who were trying to bring it back to the proper pier using the ropes thrown to them by the alarmed sailors on deck. Jay realized that his lads were short one man. The humpback ran down the pier, sliding into place next to a muscular wolf.

"Toss me a line!" he shouted to a bull sailor above. Jay caught the rope and yanked it around the large, steel cleat at his feet for extra leverage. He gave the rope a few wraps around his wrist and pulled, digging his heels into the wood of the pier below him. The other dock workers did the same as the ship drifted dangerously close to the opposite dock.

"Heave, lads!" Jay yelled, muscles bunching from exertion as the ship gently swayed back toward them until it was close enough to moor. The large humpback turned toward the panting wolf after he made sure his line was properly secured. "Hey, Kirk, where the fuck is Joshua?"

"No idea, boss. He was here when shift started this morning, but I haven't seen him since we packaged that last delivery for the monastery."

Jay frowned as he folded his arms over his chest. "Go help the other lads with unloading. I'll look for Josh-" The whale's eyes caught sight of the captain of the ship, a female tiger, angrily stomping down the gangplank seconds after it had hit the dock. "After she's said her peace."

The captain pushed past the dock workers as she marched up to Jay. Though short compared to the whale's imposing stature, she fixed him with a glare that could topple giants as she thrust out the cargo manifest for him to take.

"Are you in charge here?" She demanded. Jay nodded and she continued, spitting the words from her lips in a furious staccato. "My poor Dragonfly was almost damaged coming into your dock!"

"I apologize, ma'am," Jay replied, "We were a man short and only realized it at the last minute."

"Well I hope you find your missing worker and discipline him accordingly," The captain said, her anger cooling, though her eyes remained dangerously narrowed.

"If you wish, I could put you in touch with the Harbormaster and you could issue a formal complaint, Captain." Jay said. Most ship captains knew of the Harbormaster's reclusive, intimidating nature and many wouldn't risk their shipping rights being revoked over frivolous complaints.

"N-no, that's quite alright," the captain stammered. "There was no actual harm done and the Harbormaster is... probably busy enough as it is."

Jay nodded as he glanced at the manifest. "Very good. Now then, supplies for the carpentry and leatherworking guilds, is it?"

The captain nodded. "There's also two other boxes on board, one for someone named Guerrin and the other for the Harbormaster."

"My lads will see your cargo gets to where it needs to be. Come to my office so we can get you paid and you and your crew can start to enjoy a bit of shore leave in our fair city."

As they began to walk away, Jay could already hear some of his dock crew chatting jovially with the burly sailors who were helping to unload the ship's cargo. He briefly wondered if he might see some of those same sailors at the Sword & Scabbard later that night. After all, several of his lads were regulars at the secretive establishment, as was Jay himself. When they arrived at his office, the whale sat at his table and tallied up the total cost of the goods along with the delivery fees.

"Did the Alsam Navy give you much trouble?" He asked, removing a key that hung on a cord around his thick neck.

"None, actually," the tigress replied. "There were a few unmarked vessels following us for a while, though. Do you have any problems with pirates?"

Jay knelt down and unlocked a small door on the wall behind his table. "We have some. But they usually give our ships a wider berth than the navy's." The humpback chuckled as he pulled out a sack of coins and counted out the captain's pay into a pile atop his papers.. He scooped the pile into a different leather bag and handed it to her.

"Paid in full, ma'am. If you would just sign the bottom of my manifest there, you may begin enjoying your stay in Port Crow."

"Thank you, sir," the captain curtly replied as she scrawled her name in a cursive so elaborate that Jay couldn't decipher it. "If my ship remains intact while I'm here, I will."

Once she was gone, Jay made sure to lock the money back up in the storage space in the wall. He briefly sorted the papers on his desk before walking out the door himself. He hung a well worn sign on a metal hook, informing subsequent visitors that 'The wharf manager will be back soon'. He had to find out if Joshua had left the docks. The whale made his way to the entrance to the city proper and approached one of the guards stationed there.

"Afternoon, gentlemen," Jay said. "Have you seen a short, wiry, male fox with blue-green eyes leaving earlier this morning?"

The guards spoke among themselves for a moment before shaking their heads. An orca guard rivaling Jay's own height and build spoke up. "No, sir. A fox matching that description entered the harbor early this morning, but he hasn't left."

"Thank you, er..." Jay noticed the carved wooden name tag around the orca's neck. "...Akamai. I'll keep looking then." At the very least, that meant Joshua hadn't completely abandoned his job. Perhaps a reprimand would be all that was needed. The fox had been recommended by Theodore, the master of the Blacksmith Guild, and it would put a strain on their working relationship if Jay were forced to fire Joshua. In any case, Kirk had mentioned the monastery shipment. Usually, after a shipment was completed and sent, the wharf crew moved on to other jobs and the area was vacant for a while. Perhaps that was where Joshua was hiding; he could be napping or slacking off in some other way.

Jay snorted through his nose, annoyed by the thought. As he made his way over to the east side of the harbor, his mind conjured up various things he might say to the shirking vulpine when he found him. His crew was busy packaging the Dragonfly's cargo on the opposite end of the harbor so, as he expected, the eastern side was mostly deserted. The humpback casually strolled through the stacked boxes of packaged cargo, moving slowly so that he didn't make too much noise.

Near the very end of the wharf, where the wooden docks gave way to sea waves gently lapping against the stone walls of Port Crow, a different sound drifted into Jay's ears. To anyone who frequented the Scabbard, it would have been immediately recognizable. Firm slapping noises accompanied by hissing, guttural whispers and barely audible whimpering floated on the sea breeze past Jay's alert senses. The whale blushed at the sound, heat rising to his cheeks. But he had to know whether or not it was indeed Joshua, and who he was with if so.

Jay moved silently, a miraculous feat for one of his size, through the stacked boxes of paper and book bindings; quills and ink, as the sounds grew slightly louder. He could now make out the whispered words no doubt spoken into a scruff of someone's neck, or hotly into the bottom's ear.

"That's it, lad," the whispers said. "Loosen up for me."

Jay's stomach rolled over and his cock swiftly began to thicken.

"I've got much more to fit into you," the whispers continued. "I know you can take it, boy."

The whale crouched and cautiously peered around the corner of the boxes, and his eyes widened with sexual hunger. Joshua was bent over, supporting himself by gripping the top edge of one of the shipping boxes as Theodore, the blacksmith guildmaster himself, firmly gyrated his hips behind the fox in an attempt to fit a massive, black, girthy polar bear dick into Joshua's backside. Anger and jealousy fought for control inside Jay's gut. The humpback rounded the corner with a mixture of shock and fury on his face.

"What the hell are you two thinking!?" He hissed.

Both Josh and Theodore looked shocked, but the expression didn't remain on the polar bear's face for long; quickly shifting into a sly grin as he recognized who had caught them.

"Oh, hello, Jay," Theodore said. "Just thought I'd check in on Joshua here to see how he's acclimating to the new job."

"You shouldn't be doing that here!" Jay replied, trying not to raise his voice too much.

"Don't act so high and mighty, JB." Theodore roughly pushed three more inches into the quivering vulpine in front of him, which drew a pleasured moan from Joshua's lungs. "I've seen you at the Scabbard many times before."

Jay sputtered. "T-that's different! This is a public place! What if it were a guard who found you?" Despite his posturing, the whale's eyes remained locked onto that thick bear meat as it slid in and out of Josh. He found himself wondering how that monster would feel up his own asshole.

"Oh come now, the risk is what makes it more fun," Theodore said with a grin, gesturing to the humpback's prominent crotch bulge. "Besides, I can see you want it. Why not join us? I bet Joshua's snout would look good between your cheeks."

Jay's butthole gave an involuntary, hungry clench at the thought. How did Theodore know just what to say? The whale couldn't deny that he found most of his dock workers attractive, but he had never acted on it outside of the Sword & Scabbard. Joshua's eager groans and blissful expression pushed all of the humpback's buttons though, and before he could properly think about what he was doing, JB had unfastened his belt and let his trousers fall. He approached the gasping fox and turned, spreading his ass cheeks for the vulpine.

"Oh yeah, Boss," Joshua moaned as he inhaled the whale's masculine musk. "I've had a crush on you since I started working here, you know." The fox dragged his soft tongue along the back of Jay's sack, sliding it upward to tickle the humpback's taint as he gripped JB's fat nuts to gently tug on them.

Theodore grinned as he watched Josh lick the rim of Jay's asshole, deliberately throbbing his polar bear dick inside of the whimpering fox. He pulled two inches out and shoved four back in when Josh's nose poked JB's ass. The force sent the fox's snout a good inch up the whales butthole and JB gasped, clenching and groaning as he felt the sudden stretch. Josh's tongue didn't skip a beat, and he lapped eagerly at JB's inner walls as the older whale bit his lip and shuddered.

"Oh fuck, that's good!" Jay moaned as softly as he could.

Theodore chuckled. "See what you can get if you're just more straightforward, Jay? This fox has been wanting you for weeks!"

The bear's black dick pistoned back and forth, pushing deeper and deeper into the fox's loosening ring, which in turn pushed Josh's snout deeper into JB's asshole. Both fox and whale moaned when JB's ring slid over Joshua's whiskers, almost completely swallowing the fox's muzzle. JB panted from the intense stretch. It made his knees weak and his legs quiver when Joshua's tongue flicked over his prostate. His own cock throbbed, half hard, drooling precum onto the wooden dock below. JB wondered if he could get Joshua even deeper, but his desire for a dick overrode that question. He gently, reluctantly pulled free of Joshua's muzzle and Theodore hilted, making the fox's ass spasm in protest from the immense girth of the base of the polar bear's cock. JB chuckled as he regained his own breath and noticed the bulge in Joshua's stomach made by Theodore's cock tip.

"Lift that boy up, Theo." JB said lustfully. "I wanna feel his dick in me."

Theodore laughed and obliged, easily pulling the smaller fox off of the ground. JB slid into place on his back under the fox and lifted his legs. Joshua could scarcely believe that he was going to get to fuck his boss. The girthy polar bear shaft inside of him throbbed and made him groan as Theodore guided him into place. JB's hole swallowed his dick to the base with almost no effort, and Joshua groaned as he lay over his boss's throbbing dick and belly.

"Now, fuck me," JB commanded. Joshua couldn't move with that massive bear dick in his gut, but Theodore had no problem setting into a fierce rhythm that quickly had the fox moaning like a whore. Josh was mashed between the two larger brutes, huffing and grunting around him, and his whole body shuddered from the exquisite physical contact from two stunning, older men. His eyes even rolled up in his head when JB guided his muzzle into one of the whale's musky armpits and trapped it there with a headlock.

Theodore groaned as his cock was squeezed tight by the living fleshlight under him and he gazed into JB's eyes with lusty hunger, his thrusts increasing in ferocity. The whale grinned up at the polar bear and moaned, "Fuck me, Theo!" before pulling the polar bear into a passionate kiss. It was as if the two older men had completely forgotten about the young, shuddering fox sandwiched between them as Theodore's sexual gyrations were quickly becoming more and more erratic. JB huffed into the polar bear's mouth as their tongues wrestled with each other.

Joshua could only inhale his sweaty boss's armpit musk as he quivered and shot spurts of hot cum into JB's hungry, clenching hole. The increased tightness sent Theodore over the edge and he pulled JB into a tighter embrace as he let out a muffled grunting growl and erupted a flood of thick, virile polar bear spunk into Joshua's abused asshole. Jay's hard dick throbbed against Joshua's sweaty belly fur, and the whale couldn't deny that he wanted more. Theodore's softening dick slid free, leaving Joshua's ass gaping for a moment before the fox managed to clench it closed.

"Well it's been fun, gents, but I really must get back to work," The polar bear said as he fished his clothes from the pile behind him and tossed what wasn't his at Joshua when Jay released the fox from under his arm.

The three dressed in relative silence, but as Theodore was leaving, he looked back over his shoulder. "I almost forgot. I've received word that a few of my shipments haven't made it through to their destinations outside Port Crow. Any idea why, dock manager?"

Jay shrugged, tugging his trousers on and stuffing his nine-inch dick into them as best he could. "We shipped everything correctly. Maybe the navy or pirates interfered."

"Perhaps," Theodore said. "It won't do to have shipments waylaid. I'll have to bring it up to the Harbormaster if it continues."

"That is an excellent idea," Jay replied curtly, clapping a hand on Joshua's shoulder as the fox attempted to slink away. "Where do you think you're going, boy?"

"Er, back to work, boss..."

"Oh no, I ain't done with you yet," Jay said with a scowl.

Theodore grinned. "I'll leave him in your capable hands, then." The polar bear turned and took several steps toward the exit of the wharf.

"Theo!" Jay called after him, lowering his voice when the master blacksmith turned his head. "Do not distract my workers during their shift ever again or I will make sure all of your fucking shipments are delayed."

Theodore shot him an angry glare before turning around and mumbling 'hypocrite' under his breath as he sauntered away. Perhaps he shouldn't have goaded the whale into being more blunt after all. Jay put a gentle arm over Joshua's shoulder and guided him back through the vacant area of the docks toward his office. Kirk gave a cheerful wave as they passed, glad that the dock manager had found the mischievous fox. Most workers knew that JB wasn't a harsh employer and that any punishments he chose to dole out were fair. However, most of them didn't know about Jay's perverted side. The humpback pushed Joshua through his office door and closed it behind them.

"Drag that bench behind my desk and lay down on it," Jay ordered.

Joshua glanced nervously at his boss as he removed his shirt and did as he was told, though his heart raced in his chest from anticipation and the perverted possibilities swirling through his own head. As Joshua laid his head back on the bench, Jay tugged his pants off and kicked them into a corner, stroking his quickly stiffening dick and licking his lips. If he had known that Josh wanted him from the start, he would have done this a lot sooner.

"Had your eye on me for a long time, eh, boy?" Jay asked, shooting the fox a stern glance as he rounded the desk and stood over him.

Joshua nodded sheepishly as he looked up at the whale he lusted after and admired. Jay held his cock over Joshua's face, slowly stroking it while he felt pleasure slowly begin to rise. A bead of precum slowly formed at the tip.

"You're gonna lay there while I do my paperwork, boy," Jay said as the drop of pre fell into Joshua's waiting mouth, leaving a clear strand from the vulpine's tongue to the whale's piss slit. "In fact, you're gonna lay there until I'm satisfied that you've learned your lesson."

"W-what lesson, sir?" Joshua asked.

"That next time, you'd better tell me when you want a dick in you instead of whining to Teddy behind my back." Another heavy drop of precum slid from Jay's erection, this time splattering wetly on Joshua's nose.

"We-" Joshua's tongue darted from his muzzle to lick the delicious, musky fluid from his nose. "We're not supposed to call him that."

"Do I look like I give a fuck?" Jay said as he turned around and squatted, planting his ass on Joshua's nose. "Teddy ain't here, so who cares? Get licking, boy. I know you want to."

The fox's cold nose and hot tongue felt good on Jay's asshole, but speaking his mind freely for the first time felt even better. Teddy was absolutely right. Being forward about what he wanted was much more rewarding. Joshua's tongue obediently dragged along Jay's soft anus and it still amazed him that the whale's asshole could loosen up so readily with minimal lubrication.

JB huffed above, grinding his teeth from the exquisite feeling of a set of soft lips against his butt. Despite the pleasure, he dutifully scratched his pen over the papers in front of him, making sure all of the cargo and shipments were catalogued.

"Oh fuck yeah," the whale murmured as Joshua's cold nose pushed inside of his butthole. Joshua was in heaven. His boss's anal folds gently squeezed his snout, and the fox flicked his tongue out to taste the bitter, musky flavor of JB's asshole. The whale sank another few centimeters down and his anus spasmed from the stretch as he let out a low moan. His legs shook as he lifted himself off of Joshua's muzzle. The fox licked his lips and reached a hand into his pants to stroke his rigid cock. JB opened the desk drawer on his left and removed a bottle of oil from it.

"Close yer eyes and mouth, lad," JB said as he uncorked the bottle and drizzled some of the oil onto one of his meaty hands. Joshua did as instructed and felt JB roughly smear the slick fluid over his face and muzzle. The whale made sure to not get any up Joshua's nose, but the fox was slightly concerned that Jay was lubing up his brow and forehead as well.

"I'm finally gonna get a decent stretch from you, runt," JB said. "You might wanna hold yer breath until you get in there."

Joshua nodded and sucked a few large, deep breaths through his nose before holding it. The massive whale above him turned once more and sat down for real this time. Joshua's entire muzzle disappeared into JB's asshole and the whale let out a contented sigh. He continued his paperwork with his clean hand and his cock throbbed, spitting precum onto the floor under his desk every time his asshole sank lower, sucking more of Joshua's head inside. Jay's anus shuddered when it stretched around the fox's brow and he could feel Josh's adam's apple moving against the other side of his puffy ring when the vulpine swallowed.

Joshua was stroking himself furiously, muffled moans and whimpers barely audible through JB's ass flesh. The whale grunted and pushed with his anal muscles, trying to loosen up further. With a sudden squelch, his asshole widened and Joshua's ears and entire head slid up into him. JB shuddered at the abrupt entry and then tensed up when his office door opened and one of the Harbormaster's personal guards sauntered in.

One of Joshua's hands shot up to grip one of the whale's ass cheeks as JB's asshole clenched firmly around his neck. The fox pulled his cock from his pants, oblivious to the fact that they had been caught. Jay was silent, but couldn't deny that being watched was hot. The guard, a well built male doberman, raised an eyebrow at the scene he had interrupted. JB gasped suddenly as Joshua's nose nudged his prostate, but he tried to keep his climax in check as he started to sweat and pant from the intense, blissfully full feeling the fox's head gave him.

"C-can I help you, sir?" Jay stammered through the pleasure of the fox's muzzle purposefully nudging his prostate as Joshua obliviously pleasured himself, "I-I've seen you a couple of times at the Scabbard, haven't I?"

The guard tapped his chin, making a show of trying to remember something. "Hm, perhaps you have. Maybe you will again, but that's not the reason I'm here."

"G-go on." Jay said, his asshole spasming frantically around Joshua's neck as the humpback clenched his teeth and bit his lip with every ounce of effort he could muster. The fox inside of him was trying to get him off, rubbing his vulpine chin right up against JB's gland. The whale's fist clenched around his feather pen and he screwed his eyes shut while his erection twitched and throbbed, spitting precum into the quickly forming puddle under his desk. Fuck, it felt so damn good!

"Are you quite alright, Wharf Manager?" The guard asked and when Jay frantically nodded in response, he reluctantly continued. "The Harbormaster has need of one of your more discreet docks for a special delivery-"

The doberman trailed off as JB drew ragged breaths through his nose and mouth. "Oh fuck yes!" the humpback gasped. He couldn't hold back anymore and he no longer cared if the guard dog saw him cum. He filled the office with a loud moan as Joshua's prostate rubbing finally became too much for him and a powerful orgasm shook his body. His cock erupted long strands of cum onto the floor under his desk as he panted, sweat dripping down his sleek body.

The guard leaned against the wall as he watched the whale finish laying pipe all over his office. The bulge of his own doggy erection in his trousers would have been visible if his armored crotch plate wasn't obscuring it. Jay groaned, sucking in gulps of air as he waited for his asshole to stop spasming in post-climax. Joshua arched his back and gave a loud moan of his own inside of the whale's ass as his shaft throbbed and spat a good amount of cum onto his chest and belly. Jay glanced over at the guard as he slowly lifted himself from the fox's head, giving the doberman a tired, wry grin.

"Do you do this with all of your employees, Mr. Bayson?" The guard asked.

"Heh," Jay chuckled. "Only the ones that stare at my ass."

Joshua gasped as his snout finally came free and then he yelped when he noticed the guard dog gazing at him with hungry, predatory eyes. The ashamed fox quickly tucked his shrinking cock back into his pants and grabbed his crumpled shirt from the floor.

"Clean yourself up in the workmen's quarters before you resume your shift," Jay said. "And don't abandon your post again or you will be fired, understand?"

Joshua nodded and scurried out the door.

"Interesting way of punishing someone," The doberman said as Jay peeled his shirt from his sweaty torso and used the few remaining dry spots on it to wipe his brow. The whale stood, dick still pulsing and oozing some of his cum as he meandered around the desk. The doberman took a step forward, taking the base of JB's dick in his hand as he knelt in front of the dock master and pursed his lips at the tip of the softening erection. He squeezed the length, dragging his hand toward his face and was rewarded with almost a mouth full of the whale's potent, musky semen.

The dog made a show of rolling the cum around in his mouth, groaning in approval at the taste before he swallowed and huffed through his nose. "Delicious." The doberman said with a grin. Jay chuckled, his cheeks flushing at being complimented by the handsome guard. He grabbed a few rags from a cabinet on the wall and bent over to begin cleaning up his mess.

While Jay's back was turned, the doberman slid his crotch guard to the side and fished his throbbing cock from his trousers. He slid up behind the whale's ample rear while Jay gathered up his spilled spunk in the rags. The guard gripped one of Jay's ass cheeks and squeezed it as he hotdogged his thick shaft against the slick butthole in between them. Jay pushed back when the doberman was at the lowest part of his thrust and the lubed ass sucked the doberman's cock right inside to the hilt.

"Fuck, that is an exquisite anus," the doberman cooed as his cock throbbed against JB's silken inner walls.

"You gonna tell me the rest of the job or just waste our time?" JB asked gruffly, continuing to mop up his cum.

The doberman reluctantly pulled out and slipped his erection back into his pants, but he knelt down behind the whale. "Maybe you'd prefer this instead." He said wryly as he shoved his entire muzzle inside the slightly gaping asshole in front of him. Jay gasped and couldn't stop the slutty moan that erupted from his lips at the feeling of a much larger head than Joshua's trying to forcibly gain entry. His cock immediately shot back to full mast as the guard pushed forward, trying to get his head to pop inside.

"S-stop!" JB whined. "Y-you're too big!"

The doberman pushed a bit more before reluctantly pulling back, licking his lips and JB's puffy anal ring as his snout exited the twitching hole. "Have it your way, but don't expect me to leave an ass like that alone next time I see you at the Scabbard."

Jay grinned as he stood up on shaky legs and tossed the soiled rags into a basket near the door of his office. "I-I welcome your girth, mate. Bet you'd feel great shooting a load deep in there. B-but if you want more than your shaft in me, we'd need a lot of oil."

The guard chuckled as he changed the subject, pulling a wax-sealed envelope from a pouch at his hip. "Specifics of the job are in this envelope. All I know is that you're to meet someone later tonight to nail down the details. Make sure you keep it hush hush. The Harbormaster wants as few people to know about it as possible."

Jay took the envelope and turned it over in his hands. "To keep it secret from Alsam no doubt."

The guard shrugged as he turned toward the door. "Take care, Dock Manager. Might want to lock your door next time you decide to punish one of your workers."

"I'll keep that in mind. Thanks, genius. Before you go, there's a package for the Harbormaster that arrived today. You might as well pick it up from my boys on Dock Four and take it back with you."

The doberman nodded as he slid out the door, and Jay tugged his trousers back on before peeling the wax seal from the envelope to remove the folded paper inside. The humpback unfolded it and scanned the Harbormaster's unusual handwriting that lined the page.

It read: "Hello, Wharf Manager Bayson. I hope this missive finds you well. It would be in both of our best interest for you to meet a man named Max tonight to broker an agreement. Max will fill you in once you arrive. The meeting will take place at Barrowman's Table on Avon Lane at nine pm. Please strive to be on time. Your friend, The Harbormaster."

Jay stuffed the paper back into the envelope as Nero, one of his workers, entered. The rat's nose wrinkled before he spoke, no doubt from the musky smell of masculine sex that hung in the air.

"Hey, boss, there's a package for Master Guerrin that came in on the ship that almost crashed into the dock earlier. Should we send one of the usual boys to deliver it?"

Jay shook his head. "No, Nero, I'll take it over there myself. I've been meaning to speak to Guerrin about a few things anyway."

Nero raised one of his eyebrows. "All right, boss. Don't have too much fun when you're there, though. Might wear yourself out that way."

Jay rolled his eyes, "Who are you, my mother?"

"If I was, I'd be very disappointed in your sinful interests, I'm sure," Nero chuckled as he opened the door for his employer.

"Careful, ratty. I still pay your wages, remember," JB replied as he hung the 'Office Closed' sign on his door and locked it.

Nero grinned. "I'm sure you'll remind me in a more personal way some night at The Scabbard, boss."

"Keep up that arrogant attitude and I might avoid doing that on principle," Jay replied with a smirk as Nero pouted like a scolded child and led him to the dwindling pile of cargo from the Dragonfly. Guerrin's awkwardly shaped box was easy to pick out among the other, mostly square parcels. The humpback lifted the box under one of his massive arms and waved farewell to his employees as he made his way out of the harbor and into Port Crow's cobbled streets.

***

It was a short walk to the main entrance of the Sword & Scabbard. Due to the secretive nature of the place, one had to know what he was looking for in order to know which door to enter. The sign was tiny and affixed to the wall next to the door rather than jutting out into the street like most other stores and bars in Port Crow. JB rapped his large fist against the wooden door and waited. He hoped it would be late enough in the day that Guerrin would be in the common room, getting the Scabbard ready for the night's patrons.

After only a few moments, the door opened a crack and one of the brown wolf's eyes peered out from within. He looked like he was about to turn whoever had knocked away, but his expression changed as he noticed Jay. Guerrin swung the door wide for the burly humpback and ushered him in, closing the door behind him afterward.

"Jay Bayson! What can I do for one of my most esteemed and popular customers?" Guerrin said with a grin.

The wolf was only dressed in a pair of trousers that had been cut off at the knee, and the outline of his flaccid shaft in the fabric made it very apparent that he wore nothing else underneath them. It was an odd fashion for Port Crow, but JB suspected that such a thing would only be worn within the Scabbard or Guerrin's own bedroom.

"I just stopped by to deliver this for you," JB said, offering the box to the wolf.

"Ah, very good! I've been waiting to add this to my collection," Guerrin replied as he took the box in both arms.

"What's in there anyway? Something fun?" JB asked with a horny twinkle in his eye.

Guerrin looked the humpback whale up and down with an appraising glance. "I suppose I could show you. It's the least I could do to repay you for delivering it and we do have some free time before opening. Follow me."

Guerrin led Jay deeper into the empty Scabbard. The place had a very different feel when it was vacant. They walked past the lonely bar and large rooms filled with soft cushions meant to accommodate groups of men of varying size; they felt barren without the writhing, moaning bodies to fill them. Jay ducked through a doorway at the back of the building, near the anonymous stalls, and found that Guerrin had led him into a modest bedroom. The wolf set the box on the floor and Jay pried the lid from it, revealing the exquisitely molded head of a thick dildo. It must have been five inches across, and Jay found his shaft quickly growing hard at the thought of that thing being shoved deep inside of him. Guerrin gently lifted the toy from the box and lovingly brushed it off. He set the heavy base, a pair of hefty, molded testicles, on the floor and turned to Jay with a predatory expression on his face.

"Strip," Guerrin commanded, the wolf's voice washing over the humpback like a powerful tidal wave. It was such a simple word, but it seemed to echo through JB's head with intense authority that was worthy of one with the title of 'Master.'

Jay couldn't help but comply, lifting his tunic over his head and dropping his trousers to the floor. His shaft pulsed, fully hardening to its nine inch length and four inch thick girth. Guerrin slid forward, gently rubbing the humpback's belly.

"Wh-what was that?" Jay asked.

"Just a trick I picked up back in my adventuring days," Guerrin replied.

"You don't gotta use trickery on me," Jay said with a chuckle. "I'm more than willing to get stuffed by that thing."

"A fair point. I'll refrain from such action from now on. Please, bend over, my friend."

Jay grinned and turned around, his belly bunched up as he bent at the hip and grabbed his own ankles, which hiked his tail over his back and revealed his somewhat still loosened hole to the horny wolf. Guerrin licked his lips and pressed his muzzle against JB's taint, kissing it with his lips before he dragged his tongue up the backside of the humpback whale's hefty sack. Guerrin gripped Jay's throbbing shaft firmly as his cold canine nose poked the whale's asshole. Jay sucked in a breath and then moaned as the wolf's warm tongue slid along the puffy anal ring. The whale could feel his heart racing in his chest from the intense pleasure of Guerrin's tongue flicking against his soft, tender butthole. Jay sighed as he felt his anus loosening even further and Guerrin's cold nose slipped inside. The wolf's other hand gripped one of the whale's meaty ass cheeks and pulled it away, giving him more room to nudge and lick the rim of JB's supple butthole. As the anus loosened, Guerrin's tongue began to slide further inside, tasting Jay's inner depths up to his second sphincter. The humpback leaned farther forward, pushing his hands against the wall and shoving his ass back toward the wolf's talented tongue. For the most part, Guerrin kept his snout outside of JB's anus, merely teasing the pulsing, hot flesh with his cold nose as his tongue thrust in and out of the tender ring. He steadily, slowly stroked the whale's thick erection, grinning each time JB let out a gasping moan of pleasure, and flicking his tongue against the whale's anal walls whenever the asshole loosened a bit more.

Guerrin only withdrew his lips and tongue when Jay's asshole glistened with his spit and hung open in complete relaxation. The wolf dragged a chair into the middle of the room and placed the dildo onto the seat of it with a soft thud. Producing a decanter of oil from some unseen place, he drizzled a healthy amount over its head, and then proceeded to oil up his own palm as well. He smeared the slick fluid over the whale's loosened asshole.

"Alright, Jay, have a seat," Guerrin said with a grin.

JB was suddenly acutely aware of how empty his asshole felt, and that thick toy certainly looked like it might be able to give him the stuffing he craved. He stood over the fake dick, teasing himself with the fat tip for a moment before sinking down and taking nearly half of it at once. Jay couldn't stop the deep, whorish moan that erupted from his lungs as the toy's girth rubbed up against his loosened anal walls and slid over nerves, electrifying them with pleasure. Breath caught in his throat as Guerrin gripped his shaft with that oiled up hand and slathered Jay's length with the slick lubricant.

"Keep going," Guerrin said to the panting, sweating humpback. "You can take all of it, can't ya?"

Jay grunted and managed a grin through his blissed out expression. "Hell yeah, just- oh fuck!" He groaned as his asshole swallowed more of the toy's length until his hefty posterior was planted firmly on the seat of the chair, the fake nuts on the toy pressing tightly against his taint. JB's burly body shook from the constant pressure on his prostate that the toy provided, his cock drooling precum as Guerrin squeezed it gently. The wolf lifted his greasy hand from JB's cock and smeared the oil over his own ass before he climbed onto the whale's lap and faced away from him.

"I... ain't gonna last long if you ride me, mate," Jay gasped as he watched Guerrin's practiced asshole devour the head of his throbbing, thick erection.

"Don't think you'll only be getting off once with me," Guerrin said, groaning in bliss as he slowly sank down on JB's cock. The whale wrapped his arms around Guerrin as the wolf sank down, taking all of Jay's nine inches with surprising ease.

"Didn't know you liked this kind of thing," Jay whispered into the wolf's ear, deliberately throbbing his cock inside of the smaller man's butthole. Guerrin gasped and leaned back into JB's chest, bearing down and pressing his rear back as best he could to get that thick cock as deep as possible.

"Shut up and fuck me," Guerrin hissed.

JB was all too happy to oblige. He grabbed Guerrin's thighs from underneath and moved his own legs to the side in a squatting position, moaning as the movement put more pressure on his prostate. He lifted himself a few inches off of the toy and held Guerrin in place as he set into a quick, squatting rhythm. The room was swiftly filled with their grunting moans as Guerrin's hole spasmed around JB's pulsing, drooling shaft and the whale's ass clenched against the unyielding firmness of the fake dick. It only lasted for a few moments before JB gasped with impending release.

"C-can't hold it back any-!" His erupting cock interrupted him, and he firmly sat on the dildo as his words trailed off into a hoarse moan. He filled the wolf's clenching asshole with hot ropes of potent whale cum and Guerrin huffed in pleasure at the heat spreading thickly inside of him. JB's thick dick spasmed against his prostate, but it wasn't quite enough to get the wolf off. Still, he greatly enjoyed the feeling of that heavy load of semen firing deep into his guts. JB rested his head on Guerrin's shoulder as he shuddered through the final clenching throes of his orgasm. The wolf gently slid free and held out a hand to help his friend off of the dildo. Jay felt sweat running down his back despite the short time he had been fucking, and he gladly took Guerrin's hand, sliding up to the tip of the toy. However, the wolf wasn't quite done with him, and Guerrin moved faster than JB thought he could. The wolf grabbed the base of the toy and lifted it until it was snug against JB's asshole once again. Jay whimpered hungrily as Guerrin led him to the bed, gently guiding him down onto his back. The wolf smiled kindly down at thim as he wriggled the toy inside of JB's twitching anus.

"You want more, right?" Guerrin asked.

JB nodded in response. "P-please!" He moaned. Guerrin grinned and pulled the toy out to the tip before slamming it firmly home. Jay's cock remained rigid under the wolf's anal assault and the whale's slick asshole yawned wide around the fake cock as the swift thrusting rhythm steadily opened him up even further. It wasn't long before the wolf lined up his own cock with the toy and pushed them both in at once. Jay saw stars from the electric bliss that fired up his spine. This is what he wanted. This was how full he wished his asshole could always be. Guerrin pounded his hips against the whale's ample backside, smashing the dildo's molded nuts repeatedly into JB's taint as his own slapped the underside of the whale's thick tail. Heavy, musky scent filled the room as JB's cum began to leak out of Guerrin's ass, but it only increased the lust swimming through both of their heads as the wolf mated with the whale's asshole.

The wolf fucked like a Master should, firm and forceful, but not overly abusive. Guerrin growled as he leaned over JB's panting torso and licked the salty sweat beading on the whale's slick skin. JB lost track of how long they had been having sex, but he started to notice the familiar tickle of climax building again in his gut. He groaned and clenched his hole around that girth, his mind swimming with intense fulfillment as Guerrin hilted again and again inside of him.

"G-getting close, Jay," Guerrin grunted, his cock throbbing sporadically against the toy.

"Yeah? Fuckin' do it! Fill me with your pups, Master!"

Guerrin growled, gently gnawing on one of JB's nipples as he hilted and shuddered. The sudden increased girth that the base of the wolf's cock spread his hole with sent JB rocketing over the edge yet again. His dick pulsed between them and his asshole clenched wildly as a small amount of cum oozed from the tip of his shaft. Guerrin's cock fired a volley of his own thick cum, painting the dildo and JB's inner walls white.

They both panted heavily, laying against one another for a good while before Guerrin reluctantly slid off of JB's sweaty body. Jay stayed on the bed for a while after, his asshole twitching feverishly around the dildo still hilted in him. Guerrin opened a drawer in the wardrobe next to his bed, pulling out a good sized buttplug, which he sat on before wiping the dribbling cum from his ass and legs. He gave the dildo in JB's ass a gentle tug, chuckling softly as it flopped free with a gasp from the whale.

Jay once again felt empty, but this time, he was satisfied. His hunger had been sated for the moment. Guerrin helped him to his feet and also helped him clean up before the two dressed and headed back out into the Scabbard.

"I've got much to do before opening," Guerrin said. "But please do come back soon so we can do that again!"

Jay blushed and scratched the back of his head. "Are you kidding? I might want to move in if you can stuff me like that on the regular!"

"Did I miss someone being stuffed?" A voice called from the corner of the tavern area next to the bar as JB and Guerrin entered. A skinny river otter with brown headfur, grey eyes, and unusually large tusks was tuning a lute on the small stage there.

"Yeah, it was very fulfilling," JB said with a laugh.

"JB, meet Jon, the Scabbard's bard," Guerrin said.

"I'm pretty sure I've seen the little guy around before," the whale replied. "I should be heading out for now, though. I have a meeting to attend."

"Alright. See you soon," Guerrin said.

"Later!" Jon waved from the stage as JB stepped out the door.

***

Barrowman's Table was more crowded than Max would have liked. He sat in a corner booth waiting for his contact from the docks. He was technically early. When the large whale he had been waiting for entered, Max waved him over.

"Max, I presume?" JB asked.

The massive, blue megalodon shark seated at the table nodded and Jay gingerly sat down on a sore rump across from him. The two ordered food and then Max leaned in when he was certain that the waitress was out of earshot.

"Mr. Bayson, The Harbormaster is under the impression that the Alsam Navy is our common enemy and we may be able to help one another. So... tell me what you can do for the Bloodwake Pirates."

END