Painful Plundering

Story by Joshiah on SoFurry

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#11 of Bondage stories

Anything goes on the open ocean, and in this story for a private commissioner, one cat burglar discovers that there's no honor among thieves...and they aren't afraid to punish their competition!

Millie is a literal cat burglar that has made a name for herself all over the city of Westfall, and with that infamy comes the struggle of staying hidden. To escape the heat of the local law enforcement, she decides to try something a little different: stealing from her worst competition!

She infiltrates the dread ship "Lupengard" after they finish their own haul at the docks, and with the cover of nightfall to keep her hidden, she gets her paws on a crate of gold...but she isn't fated to escape with it. Dumb luck stops her from getting off the ship at all, and she's barely conscious when she finds herself bound to a wall and surrounded by furious pirates.

They're curious about her skills, but the greater interest is in her body; tight fabrics are ripped away before the pirates take a very personal, sensual revenge...but as their assault on her body continues, the cat burglar proves not only resilient, but quietly eager...

Commissions are open! https://docs.google.com/document/d/1M4k7uyTIRESrkmEhcuQPtznK7qDFrDH358Vk9-bYrGY/edit?usp=sharing The word block has been expanded to 75,000 words, so come get your share!

If you enjoyed this story, please consider supporting me on Patreon! https://www.patreon.com/Joshiah Every dollar helps, now more than ever!

As always, read, comment and enjoy!


To infiltrate a pirate ship on the open sea was a nigh impossible task, but putting the boat in a harbor didn't make it all that much easier.

As a professional cat burglar who made the bulk of her best hauls off of docked pirate ships, Millie would have been able to tell you that, when she wasn't silently creeping around the deck. In that moment, her voice would be as silent as her steps; even the swish of her tail as she turned corners and mapped her way down to the belly of the beast was completely drowned out by the occasional babble of waves breaking against the side of the ship.

Once she was in, it _should_have been easy to make her money back, but plundering from a pirate ship was a full scale investment.

In town, she had to find privateers with loose lips and cheap loyalty to buy the secret passageways of the vessel from.

In practice, her skills had to be sharpened down to a science, so that she couldn't create any faults of her own en route to the location of the treasure.

Of course...

"Haven't hadda bloody piss 'ike dat in years..."

WHUMP! All of the time, skill and finances in the world couldn't make up for one stroke of bad luck. Though her eyes were better than the average burglar in the night, she couldn't see the seam of the door to her right as it opened, slamming into her face and leaving her dazed before a drunk and disorderly pirate.

That he didn't exact his will on her right there and then was merciful, but as he leaned over her shaking form, the rum on his breath wasn't the most pleasant thing to come around to.

"Well, ain't ye a pretty li'l sight! 'Fraid we ain't got much inna way o' riches on this here ship, li'l lady. We'll have ta see what the cap'n wantsa do witcha..."

Still reeling with pain and trying to get her focus, Millie found her greatest weakness being exploited as she was gripped by the shoulder. From the tight fabric of her sneak suit, she was easily and unceremoniously dragged through the hall of the ship, splintery wood tearing gashes in the fabric and leaving her back almost completely exposed before they even neared the captain's quarters.

Really should have brought something on board to bargain with. I've gotta stop making that mistake, Millie thought, trying to contemplate anything that she could offer in exchange for her freedom. There would be other ships to steal from if she was able to get free, but if the captain didn't take mercy on her...

She gulped as the pirate who was lucky enough to snag her knocked of the door of the captain's quarters and stepped inside.

"Aye, cap'n! Found us a li'l bilge rat in the hall here!"

The rest of the ship was pitch dark, but there was a tall, solemn figure sitting at an oak desk, his expression illuminated by a plethora of candles.

The shadows that danced over his muzzle darkened the bags under his eyes, turning his smile from a friendly curl to a devious grin.

"A bilge rat, you say? Even I can see from here that you've found an alley cat."

"Well, it's a smidge dark out 'ere, cap'n."

"It certainly is," the captain agreed, his voice notably smoother than the grinding tone of the pirate who'd captured her. "Why don't you bring our little intruder into the light? I'd like to see who was foolish enough to board my ship without my permission."

With a mask covering her muzzle and the darkness of her sneak suit covering her fur, it would have been hard to identify Millie even with the aid of the candles, but a single gaze into the ferocity of her expression caught the captain's full attention.

A single lock of her hair popped through the small gap of her mask and dangled over the chocolate brown of her irises, and in the warm glow of the quarters, the curvature of her body was unmistakable.

"Now... this , I wasn't expecting! We're blessed with the company of the fairer sex this evening," the captain immediately stood from his desk and kicked back his chair. "Forgive me for not introducing myself sooner. I am Captain Velgard of the dread ship Lupengard...and you, whatever your name might be, are now a prisoner in my charge."

Whether or not she liked the arrangement, Millie didn't have a say in the matter, even when the captain stepped forward and tugged down at the front of her mask, exposing her whiskers and giving her muzzle a better avenue to breathe.

"Might we have the name you go by in the ports across the world? Perhaps if you're a burglar of great renown, we'll hold you for a ransom instead of giving you the usual treatment."

A wolf that was polite, charming and well-spoken would have been quite the desirable combination for Millie, if he wasn't dangling her world from a proverbial string.

"I'm Millie...cat burglar of the towns of Portsmarch, Westfall and Seafair. Surely you've heard of me before?"

Being auctioned wouldn't have been her first choice, but compared to what she could only assume was being forced to walk the plank, she decided to play up her reputation.

In the last way that she expected, it completely backfired.

"Millie? Just Millie?" the captain asked, his brow cocked as he released her mask, letting it rest under her chin. The exposure of her muzzle seemed an innocuous thing as he stood and examined her, but there was something bothering the feline already, beyond the obvious fact that she was now a prisoner. "Are you keeping your last name from us because it'll get you in deeper trouble? Or is it because you're the only Millie that's ever been caught wandering around on pirate ships before?"

His tone was sarcastic; he was toying with her, and she gulped when she realized it.

"A small case of our goods went missing the last time we were in Seafair...given how choppy the waters outside their port are, we assumed it to be the work of the ocean and a tiny crack in the hull, but I thought that it looked suspiciously perfect to have been made by nature's chaotic architecture," Captain Velgard explained his forgotten theory to Millie as means of venting, while providing an excellent distraction. "Seems you've confessed to the crime without us having to torture it out of you, but think of all the fun that we'll miss if we stop here...wouldn't that just be a shame?"

"W...Wait, you don't have to do this!" Millie started to plead. She didn't realize how deeply she'd become entranced by the captain until she heard snickering behind her, and her arms were yanked back firmly. "I've still got that crate! I...I can return it!"

She never saw the shackles on the wall, but when she felt large, thick cuffs of iron slam closed around her wrists, she became very familiar with them. Chains rattled, the sound forcing her ears to flatten as she was pushed back by her shoulders, the seemingly gentle Captain Velgard quickly shifting to a sinister attitude.

"In time, you will," he growled, his thick, heavy paws pushing down against her shoulders and keeping her on her knees until the shackles were locked into place. She leaned forward, but her arms were tightly pulled behind her, and even if she dislocated them...she'd just be hanging on the wall, utterly helpless. "But first, you've to pay interest on your stolen income!"

The pirate who was lucky enough to nab her in the first place invited the first mate into the Captain's Quarters, and with that, the door was locked behind them. Four paws flew to Millie's tight fabrics, and immediately, claws began to rip through her sneak suit. She felt the jagged tips scratching her flesh as tatters of cloth fell to the floor of the cabin, and right before her eyes, Captain Velgard presented her with a sight that struck chords of both fear and excitement within her.

"Y-You can't be serious," Millie looked up at him with pleading, quivering eyes of delicate brown, her expression downright glassy as the hefty flesh of his cock hung before her. It was already stiffening before it was given a single touch, prompting Millie to waste a gulp as she watched; it would have been better served around his shaft, but there was no taking it back, and no way to prepare for it.

Without arms or paws to slow his approach, Millie kept her muzzle closed, even when the tip pressed firmly against her lips. She tried to turn her head to the side, but a large, thick set of digits caught the side of her head and tugged hard at her ear, forcing her to meet with her fate.

The first mate gripped her lower jaw and tugged it open, and with a grin, Captain Velgard took his newest treasure by force.

"Have your fun with 'er, boys. Not every day we get a treasure we can actually have some fun with," the captain wasn't afraid to reduce Millie to the shackled object she'd become. Her glare narrowed on him as she still found herself locked with his gaze, but it was drawn away for a moment as the last bits of her sneak suit were ripped away.

Her breasts were only able to enjoy a moment of freedom before the first mate, a feline himself, caught them in his grasp and squeezed them tightly. "Awful generous of ya to share the booty with us, Cap'n!" he sneered, his digits eagerly pinching at her nipples and drawing a wince from her as his eyes shamelessly gazed upon her exposed womanhood.

Millie found her knees spread just by the virtue of her pose, but where it made for a more comfortable stance, it left her no way to hide herself from the lecherous grasp of the man responsible for her capture, no matter where he decided to grope her.

He started with the curve of her rump, and the sudden, unexpected squeeze forced her to lunge forward, her already busy maw getting stuffed further with the warm, throbbing flesh of the captain's cock.

"Can't believe she's so eager for it! It's already rubbin' the back of her throat," the captain complimented her skill, even when he knew she was being forced to act. Her eyes were glaring up at him as she turned her attention back to his voice, but a pair of paws settled on her ears and tugged them forwardly harshly, until her nose bumped right into the fuzz upon his crotch.

She was forced to drink in his scent as her muzzle savored his warm, pleasant taste, but no matter how she tried, she couldn't help gagging just a little bit as the cruel, sadistic captain swabbed his member against roof of her maw.

To be so completely exposed in front of the crew was degrading enough, but a part of the feline wondered if she might have been enjoying herself as the captain stared down at her with eyes that were more than eager: there was a hunger in them that frightened her, but she wasn't able to focus solely on that, or the oral delight of his length, throbbing against the flat of her tongue.

Tight, random squeezes at her breasts and a lewd, sneaky pair of paws that explored her rump without shame made it difficult for her to focus on any single part of the experience, but she had a feeling that this wasn't going to be the only session of torture she endured.

"Me thinks she took a li'l ocean water up when she got on the ship," her original captor slipped his open palm over her womanhood and cupped the delicate warmth, rubbing the heel of his wrist against the base of her folds. "Awful wet down 'ere..."

The first mate snickered at the joke as he gave Millie's breasts a final grope, her flesh giving way to the force of his digits. "Got some perky li'l nips, too. You're treatin' her too nice, Cap'n!"

Gagging still and nearly choking on the plentiful length of his manhood, Millie swallowed reflexively as she struggled to keep air coming in her nostrils, but the presence of something warmer at the back of her throat created a new, greater challenge than she'd anticipated.

Cum was gushing right down into her gullet as Velgard released her ears, only to curl his digits into her long, brunette tresses. Her hair twisted up into his hands as he yanked her head forth, and as tears welled up in the corners of her eyes, she strained to swallow down an impressive, canine yield.

How fucking long do these guys go without cumming?! Even her thoughts were panicked as she felt another thick, spreading gush of seed against the back of her tongue, but even with the deep pulses in his member, Captain Velgard didn't show even the slightest wince of delight.

"I certainly am," he agreed, his wrist tilting back to force Millie's head to tilt, showing the impression of his thick, hearty length against the front of her throat. "Especially when she's wasting my mess! I thought you little robbers were downright greedy for treasure, and here you are, letting it spill over your chin!"

Her chin, lips and even the side of her cheek were stained with the plentiful volume, and finally, a last strand landed between her eyes as Velgard pulled out and stood back, staring down at his handiwork.

Despite her tears, her stained muzzle, and the pawprints upon her body...the captain wasn't satisfied.

"We'll leave her here for the night, then," Captain Velgard declared. "In the morning, we'll see if we can't come up with other ways to get her to reveal the location of our stolen treasure."

His crew was snickering gleefully at the thought, their final touches fading away with the last of the flames as the candles were blown out. In the darkness, a panting, dripping feline hung from her shackles and whimpered...

...Because the fun had come to an end.