Angelica's Pirate Booty/Story

The waves lap at the side of the rugged wooden ship as it emerges from the thick fog wafting lazily over the water. Black sails billow out, propelling the craft forward as the pirate crew sets them loose. The heavily-laden merchant vessel was not prepared for their surprise attack as they drifted slowly towards the nearest port. As the black-haired pirate captain held his curved sword aloft, he cried out to his crew. "Take all their booty! Break their sails - pillage and conquer!"

The nimble pirate galleon swung up alongside the larger, less well-armed ship as the crew of scallywags cheered and drew their sword and flintlocks, the cannons below deck firing. Wood splintered as the merchant ship's mast crashed overboard, taking their primarily sails with it into the unforgiving ocean waters. A gangplank was pushed overboard, motley pirates raced over to engage with nicely dressed merchant guards. "It's the pirate ship, Dread Anchor!" One of the merchants cried, an older looking man wearing a powdered wig. He grabbed his well-dressed daughter's hand and dragged her below deck with him as the badly outnumbered merchant guards tried to hold back the flow of pirates.

The imposing captain watched, laughing as his crew swarmed over the gangplank. Stepping onto it himself, he confidently stepped on board himself to run through a merchant guard as the young man ran at him. Kicking the body overboard, he held his bloodied sword aloft. "This ship belongs to Captain Dread Beard now!" The pirate captain walked over to a finely dressed man holding a fancy cane out like a sword and swiftly disarmed him, impaling him through the chest. Grabbing him by the shirt, he tossed the body aside, seizing the young woman that had been cowering behind him and throwing her towards a cluster of his pirate crew before turning back to them. "Find the booty! Find the slaves! Find the captain and bring him to me alive!"

Below deck, the old man drug his young daughter after him, her long blonde hair escaping her hair net as the bonnet flew off her head. "Father, what do we do!?" The little girl stammered as the nimble old man pulled her past barrels of supplies and into a small bunk room, tears welling up in her bright blue eyes. "You must hide, Angelica! The stories of what Dread Beard does to those he captures... I could not bear it if he found you!" At only 10 years old, Angelica had trouble keeping up with her father as they ran full-out. This was her first time out at sea. It was supposed to have been a holiday for her in the next town over with her father, and she'd been looking forward to it all season. Now all the stories of mean, evil pirates raced through her mind as they ran past a barrel of potatoes that had spilled over during concussive blasts of the cannons.

The old man pulled his daughter into an alcove between two stacks of crates, fumbling at a large ornate wardrobe lashed to the side of the hull with heavy ropes. Behind them they could hear footsteps as pursuers ran after them. "Damn clasp...!" Gasping, the old man fell to the floor as the wardrobe popped open, though he quickly scrambled to his feet. "Inside, Angelica! Quickly!" He pushed the little girl inside, slamming the door shut behind her and leaving her in pitch blackness, broken only by a thin outline of light between the crack in the door. "No matter what you hear, you mustn't make a sound! Promise me, Angelica!" The little girl sniveled as her father did up the latch on the outside of the wardrobe. "I p-promise, father..!"

Outside, the sounds of battle drew closer, the sound of men fighting and dying as the merchant crew tried desperately to hold back the pirates. The old man stood, dusting himself off as several pirates ran through the doorway. "Well, what do we have here? The captain?" Asked the largest of them, grinning to show naked gums. "That I am, the captain of this ship." The old man straightened up, trying to look more dignified than he felt. The mangy pirate grinned at him, grabbing him by the arm. "The captain wants to have a word with ya, yer majesty." he said mockingly, before turning to bellow behind him. "I found him! Get Cap'ain Dread Beard!"

The little girl stashed away behind him whimpered as she heard the struggle and death throes of the last of her father's guards. She could hear the sound of more pirates coming down the hallway, their boots echoing in the empty corridor. She's heard tales of the terrible Dread Beard, a man who'd killed thousands, burned entire cities, and sold the survivors to slavery - or worse. His heart-stopping laughter sent a chill down her spine, as the running footsteps grew louder and louder. Dread Beard walked in, flanked by several of his scurvy crew as Angelica watched through the crack in the wardrobe door. "So, ye are the captain of this here fine vessel? The merchant ship, Seabreeze, if I don't miss my guess. I be most pleased. Yer cargo will fetch a nice price, indeed."

"Take my goods, if you wish, but cease harming my crew!" Angelica's father demanded with all the iron in his voice he could muster. The black-bearded pirate captain stepped forward, leveling his sword at the old man's throat. "Ye got serious brass, merchant lord, ta threaten me with swords out. Why should I not take all yer booty, and sell yer crew at the nearest slave port?"

Angelica held her hands over her mouth to stop her sobbing from getting out, she was so scared. "You'll never find the gold cashes without my help." Her father said calmly, though inside he was very afraid. "Do you think this is my first run-in with pirates? They'll well hidden." Dread Beard let out a throaty laugh that sent chills down Angelica's spine as he pulled his sword back. "Brass indeed! I respect ya, captain. Yer not one of those lily-livered merchants, are ya? Do ya have a name, bold brass?" The old man made himself stand up straighter as he stared down the pirate captain. "Gregory Harrison, Captain of the Seabreeze."

"Very well then, Captain Harrison. I'll make ya have a deal. Show us the gold, and I let ya keep six of yer crew." The old man blanched. "Th-That's not good enough..! I demand all of my crew be left unharmed..!" Dread Beard stepped forward, kneeing Captain Harrison in the belly. As he fell to a knee with a wheeze, the pirate pressed a flintlock up against his neck. "Six crew, Captain. Take it, or I blow yer brains out here and we take our chances finding the gold ourselves. Ya won't be getting a better offer from me."

Angelica's breath caught as she watched her father. She was terrified for him, and for herself, but she couldn't do anything but watch. "You.. We have a deal, you filthy pirate." Dread Beard let go of the old man and grinned, showing shattered teeth replaced with gold studs. "Wise of ya to comply. Take us to yer caches." His head went back, and bellowed out: "KEEP THE REST OF THE CREW ALIVE! TIE THEM UP!" Looking at the pirates flanking him, he pointed to three. "Start takin' what's down here up and loading it up. The rest of ye, come with us."

Angelica watched as her father was led away, left alone in the room with the three mangy pirates. "What do we grab first?" One looked at the others as they looked around. "That." The tallest of them pointed his cutlass at the wardrobe Angelica was hidden away inside, making her flinch. "That looks valuable. Let's get it above deck!" The girl's heart raced as the pirates moved towards her hiding spot, cutting away the heavy ropes tying the ornate mahogany wardrobe to the wall, before using the remains of the thick ropes to tie the wardrobe shut, making her even more trapped than before.

They pulled it away from the wall, scraping it along the floor as Angelica got jostled around inside. A tiny yelp escaped her lips as her hands got banged free of her mouth, making the pirates stop. "What was that?" One of them called, the bulk of his body blocking the door crack and leaving the little girl in complete darkness. "I didn't hear nothing." said his counterpart, whacking him on the leg. "Keep dragging, if we get a good enough haul, cap'ain might let us play with the slave girls during the celebration!"

The little girl's mind raced as she tried to think of something - anything she could do as the three burly pirated dragged her hiding place above deck, sliding it over towards the ship's railing with a pile of expensive goods - fancy rugs, tapestries, paintings and crates of expensive soaps. More and more pirates came over the gangplank as Angelica watched, her eyes flicking to a small group of survivors tied up by the destroyed mast. She recognized one her father's oldest guards, badly bleeding from a wound to the belly, and a handful of others. Screams drew her eye to the railing by the gangplank, where the few other female passengers were being gathered up. These were young women on their way to meet their new husbands in the next town over, Angelica remembered. The girl watched as some of the pirates tore away at their blouses, stripping off their corsets to bare their breasts. They laughed as they fondled them, the woman screaming and pleading for them to stop.

A few minutes later, men carrying heavy chests ladened with gold and jewels walked by, and Angelica almost breathed a sigh of relief as her father walked into view with Captain Dread Beard. "Ya have been a man of yer word, Captain Harrison." The old man looked up at the imposing pirate, and Angelica saw that his eye was blackened, wincing. "Yes, you have your gold. Now I shall choose my six crew to be spared." Dread Beard turned to look the old man, a grin crossing his wicked face. "Choose? I never said ya got to choose the six." Her father sputtered and blustered at this. "B-But we had an accord!" Dread Beard laughed bawdily. "Ya should have chosen yer words more carefully then, dear cap'itan! Allow me to educate you!" In one swift motion, the pirate drew his cutlass, sending it chopping down toward the old man's wrist.

Her father screamed in agony as his hand flew off, sliding several feet along the deck where it lay as blood squirted from the stump. He fell to his knees as Angelica screamed, her shrill voice drowned out by the cheers of the pirate crew. "Here be something ta remember yer lesson by!" Captain Harrison tore off his outer coat, wrapping it around his stump as he shuddered. "Y-You filthy pirate!" He cried out as Dread Beard cackled. "Looks like ya got yer six crew right there!" He called, pointing his cutlass at the remaining tied up guards. "Oh, my mistake." He drew his flintlock and fired it at the group, the pewter ball piercing one of the guards in the chest as he screamed. "Ya had seven there, my mistake. My boys don't count so good." The crew dragged the screaming young woman over the gangplank, tossing them over their shoulders as they laughed. Several other pirates came to collect the rest of the bounty pulled from below deck, including the wardrobe Angelica still hid inside.

The little girl was still too much in shock to say or do anything as they began to drag the heavy piece of furniture towards the gangplank. "Wait! You can't take that!" she could hear her father shout as her wooden box scraped across the wooden plank towards the pirate ship. Angelica couldn't hear anything else as the wardrobe thunked down onto the pirate ship's deck, slamming her against the side. The side of her head was on fire as she reeled, her vision going blurry as the wardrobe was drug below deck in the pirate galley. She could dimly hear the pirate captain's bellow of "CAST OFF!" and the sound of several heavy cannon shots before her world went black.

---

The sounds of laughter swam into Angelica's consciousness as she slowly came to, feeling a sharp pain in her neck and an even worse throbbing in the side of her head as she tried to pick herself up from where she'd laid jammed up on her side against the wall of the wardrobe. Memory flashed back to her as she remembered what had happened. The screams of the dying guards filled her mind again and made her whimper as she stood up inside the wardrobe, feeling something wet on her scalp. Reaching up to touch it, she look at her fingers in the dim light filtering through the crack in the wardrobe door - it was blood. She felt queasy looking at it, but was quickly jerked back to reality by a scream from outside. Angelica gulped, steeling herself before edging up against the door and pressing her eye up to it to get as good of a look as she could.

Her eye went wide at what she saw - she saw one of the young woman from her ship.. what had her name been... Veronica? The young woman was crying out in pain as a large pirate held her down on the dirty floor, tearing her skirt as she tried to kick at him. "Wha's the matter, luv? Don't fancy a roll in the hay?" The watching gang of pirates laughed and passed around frothing tankards as he tore off her ruined skirt, leaving the young woman naked on the floor. Angelica's breath caught in her throat as the big pirate pulled his trousers down, his erect penis flopping out as some of the onlookers pressed booted feet against Veronica's tender flesh to hold her down, pinning her to the floor as the pirate who's spoke first forced her legs apart. She tried kicking at him desperately, but it was no use. "Noooo! That p-place! I saved it f-for my fiance!" He jammed his cock inside her, laughing as she screamed, her hymen tearing as he forced his length all the way inside the young woman. "Yer fiance don't own ya no more, we do!" the burly pirate snickered as he raped the sobbing woman.

Angelica shuddered, knowing at least vaguely what was happening. As a proper young lady, she had been told the importance of protecting her chastity from those who would take it from her, and the importance of saving it for her husband, as Veronica had just said. She gulped, watching the long meaty stick between the pirate's legs slam in and out of the hold down between the older girl's legs, taking that most important thing from her as he grabbed and fondled her average breasts. "Not enough meat on these melons, but she be tighter than me old ma's coinpurse!"

One of the other pirates grabbed the young woman's chun roughly, yanking down his own trousers. "Use that pretty lil' mouth o' yers fer som'thin other than yelpin' like a wounded pup'!" Her forced his member down her throat, making her gag as the woman was forced roughly to deep throat his manhood. Angelica was shaking as she watched, fear trickling down her spine like lightning. Would they do that to her, if they found her? How would she get away? She couldn't stay in here forever!

The pirates took turns raping the young woman as Angelica watched on in terror, unable to peel her eyes away from the horror unfolding just outside her wardrobe. The watching men got out and jerked their penises over the woman, coating her in a sticky white substance that the little girl has never seen before. It wasn't pee, but it came from the same place. Perhaps they were sick? Pirates were dirty, filthy men, after all!

The gangbang party went on for over an hour, mead being passed around and consumed heavily as the pirates satisfied themselves inside the poor young woman on the floor. Eventually they tired of her and left her there, leaking semem from every hole as her glassy eyes stared at nothing. Was she... dead? Angelica craned her neck forward to look, breathing a sigh of relief at seeing the woman's chest rising and falling, her modest bosom flopping as it did.

"To the haul!" One of the pirates raised his tankard in a toast and the others echoes him. "To the haul!" They drank them down, hooting and laughing. "So what of this junk do ya think will fetch the best price?" One of them asked in a heavily slurred voice. The pirates began looking around the room at the chests and crates piled up from Angelica's ship. "Maybe that thing there." A man with a missing left hand pointed his hook at the mahogany wardrobe, sending a jolt of panic through Angelica. "Da' thing looks f.. f-fancy! Hic!" Several of the pirates stood up and walked shakily over towards the wardrobe, eyeing it up. "It does look mighty fan. fanc... fac-if-i-cal." declared a red-headed man with a massive beard. "Bu't wait! Wha's inside it?" Added a scrawny man, leaning forward and squinting at the thing. "Wha't if it have jewels inside? Did nobody check it?" There were murmurs from the group of pirates as they asked around. "Who brought.. it there, erm, onboard?" Asked one. "Jimmy the Quick and his lot, I.. think?" Said another, and the group turned to look at the three men who's dragged Angelica's wardrobe over. "Did ya three bums check wha' be inside the pretty?"

"We had no orders ta look in it, just ta grab it." Said one of the three. "Then we shud' check wha't be inside!" declared the red-headed pirate loudly. "The cap'tain would want ta know." The other men loudly agreed with each other as Angelica began to panic even more. They were coming closer, unsheathing belt knives and starting to cut away at the heavy ropes. She kneeled down, curling up in a ball with her arms over her head in a blind panic as the thick ropes fell to the floor, and the drunk pirates fumbled at the door catch. "Nah, ya too drunk, lemme!" Said one voice. "Ya, let Henry the Pick do it, ya idgit!" called another pirate, and Angelica whimpered hearing the click sound of the metal catch coming open. The wardrobe doors opened wide as dim lantern light filled her dark hiding space. "It be empty! Wait, no it's not! There's one of those big dolls down here." The red-haired man shoved the lanky lockpick aside as he scoffed at him. "That be no doll - that be a girl!"

Fear electrified Angelica's sore limbs as she tried springing to her feet and running away, but there were too many large pirate men in front of her. Large hands grabbed her arms and her hair as she tried to flee past them, pulling her back as she screamed. The red-headed pirate snaked an arm around the little girl's waist, hoisting her up into his arms as he held her tight, her little legs kicking uselessly against the big man's thighs. "L-Let go of me!" she shrieked, before his other hand clamped over her mouth. "We got us a stowa... stowaway!"

Tears leaked down her cheeks as the men crowded around to look at the kicking girl, one of her fancy thin dress shoes flying off to hit a man in the arm uselessly as they all peered at her in stunned, drunken silence. "Too young - throw it back." One of the pirates declared, brining a wave of chuckles from the others. "She's dressed all fancy-like." said the hook-handed pirate who'd first pointed to wardrobe. "Her family's got money. That's silk she be wearin', and lace around the sleeves and collar." The other pirates looked at the man. "Ya'd know best 'bout that, Gregory the Fence." The red-haired pirate holding her slug the girl over his shoulder, ruffling her white petticoats. "We shud bring 'er to tha captain." one of the pirates declares. "Aww, can' we at least break her in first?" said the man with the hook for a hand. "Whaa, ya like yer woman this scrawny and bosom-less, Shady Carl? No accountin' fer taste." The hook-handed man looked offended as his friends laughed at him. "Wha? I like playin' with the tiny ones is all. They scream' more, and can-not run away so gud." His friends heckled him some more often this as Angelica sobbed and tried breaking out of the meaty hand over her mouth with no avail.

"Doesn't matter, the captain will know what to do with her." said the one holding her. There was a wave of agreements from the group as Angelica got carried through the musty underbelly of the ship. She saw other pirates passed out as they bobbed past, along with a few of the other young women from her ship left naked and leaking like Veronica had been, making her shudder. A cool sea breeze made the little girl shiver as they walked above deck, the clear night's sky above them dotted with hundreds of stars. The group carried the little girl over towards the large above deck cabin typically reserved for the captain. Two guards stepped in front of the door as the group approached. "What do ya lot want?" demanded the larger of the two. Angelica's captor pulled her off his shoulder and held her up for their inspection. "We found this one hid'in in that big fancy wooden thing we brought over earlier today. Thought the captain would want ta' know." The two looked at Angelica up and down as she shivered, before sharing a look. The smaller of the two slipped quietly inside the cabin as the door shut. "If the captain wants ta see her, ya leave her here with me. Otherwise, she goes right overboard." Angelica went still as some of the pirates chuckled, more tears filling her eyes.

A moment passed before the smaller guard reemerged from inside the captain's cabin. "He be very interested in meeting the little miss." The larger guard nodded and sheathed his cutlass, holding hands out towards Angelica. "Give her here, and be about yer business." The red-haired pirate reluctantly handed her over. "F-Fine, but I want captain ta know that I was the one who caught her!" The big guard spat on the deck as he took hold of the shaking little girl, one hand about her neck as he held her by the thighs. "Ya get yer credit if I be in a good mood, now - clear out!" The group of pirates grumbled to themselves as they lumbered back below deck. The big man looked down at Angelica, his hand squeezing hard on her windpipe, cutting off her air. "I dun like brats. Ya don't scream nor cry loud in the captain' presence, or I make ya hurt. We clear?" The pressure let up on her throat just enough for the little girl to weakly nod. "Gud."

The big door guard carried the little girl as if she were a feather as they walked into the captain's chambers. Angelica's eyes flicked around the room at the fancy maps and charts on the walls, along with colorful rugs like those she'd seen in high-end markets back in her home city. Captain Dread Beard lounged behind a long ebony desk, staring intently at Angelica as the door shut behind them. A steaming cup sat in front of the scary-looking man, with a fancy porcelain teapot on a decorated platter sitting next to it. Her eyes widened at the sight of a delicate red-silk couch placed in the corner of the room, on which lay two very scantily clad girl chained up with gold-plated chains. They looked around Angelica's age, which made her shudder even more.

"Where was the little mite found?" His harsh voice sent shivers of fear down the little girl's spine as the big man holding her answered. "Red-Belly Pete and his crowd found her in that fancy wardrobe we brought over from the Seabreeze." The captain stared at Angelica for a long moment, his eyes roving up and down her body, taking in her white silk dress and fancy lacy petticoats. Finally, he sat up straighter, and indicated a comfortable looking chair with a lime green cushion in front of the desk. "Set the young lady down, Jeric. Ya be frightening her." The big man let go of Angelica's throat to salute his captain. "Eye, captain." He roughly pushed Angelica into the chair, where she immediately pulled her legs up to her thin chest and hugged them, still shaking. Dread Beard grabbed a second cup off the platter and poured a cup of tea for the little girl. "Leave us, Jerik. And ensure that master Pete and his friends get an extra barrel of mead on this fine night." The big man inclined his head towards Dread Beard. "I'll take care of it personally, cap'ain."

The pirate captain watched the big guard leave, only speaking after the door closed behind him. "My first mate. A fine, devoted man. No doubt he scared ya before he brought ya to me. Please." He reached inside his fancy red coat and pulled out a hip flask, tipping a small amount of liquid inside the cup of tea before sliding it a little closer to Angelica. "A refined lady should know it's impolite to refuse' a cup." Angelica hesitated, before letting her legs drop back down to the floor and reaching out a shaky hand for the cup. As she put it delicately to her lips and tried to take a sip, her shakes ended up sloping some of the tea onto her dress. The pirate captain swiftly flicked out a handkerchief from inside his sleeve and offered it to her. Angelica set the cup down and reached out with shaking fingers to accept the napkin, wiping up her spill by dotting at it daintily.

"I see now why the old penny-pincher surrendered so easily, and wanted ta keep that gaudy wardrobe so bad." Angelica looked up with a start, setting the handkerchief down on the table. "Yer his own flesh and blood, I take it? Granddaughter?" Angelica swallowed the lump in her throat, trying to work up the courage to answer the man. "D-Daughter..." she managed to squeak out, her voice sounding rough and hoarse from all her screaming. "Ha, I knew that old cook's had brass. Fostering, at his age, I respect that." The girl looked up, meeting Dread Beard's nearly black eyes with her shockingly bright blue ones. "Y-You cut off his h-hand..!" She stammered out.

Dread Beard sighed and pushed his chair back, getting out from behind the desk as Angelica cowered, hunching her shoulders high. "Ah, ya saw that, did ya? It was just business." A large hand laid itself on her shoulder, making her flinch as her shakes resumed. "I be sorry such a refined lady such as yerself had to witness such a crude act." A second land laid itself on the little girl's other thin shoulder as the pirate's fingers began to knead at her knotted muscles. "What be yer name, child?" Gulping, Angelica tried to answer. "A-Angelica... A-Angelica H-Harrison..." The large hands on the neck pushed down more, kneading deeper into her muscles. "Nice ta be makin' yer acquaintance, Miss Angelica. Why so scared, sprout? I know I be a mean pirate on the field, but I have'ta put on a fierce face fer my men, ya know. I'm bein' nice in here. Why ya bein' the timid cat?"

Angelica shivered, but the fingers kneading into her shoulders actually felt nice. "I.. I..." she stammered, her throat paper dry. The big pirate held the cup up to her lips, and she drank a swallow of the tangy liquid. "Take yer time, little kitten." Setting the cup down, Angelica saw his hands reaching over her to grab the handkerchief and pour more liquid from the little flask onto it, before bringing it up to her forehead. "This will likely sting." The little girl winced as the wet cloth pressed against the wound on her scalp. "Oww... U-Ummm... I'm s-scared c-cuz you took me from my f-father, k-killed people... a-and..." She gulped, thinking about what she'd seen below deck as her eyes flicked to the two girls still lounging perfectly still on the couch in the corner. They hadn't so much as moved an inch since Angelica had been brought in, and would not meet her eyes. "Y-Your men... did things t-to th-the... w-women."

The drabbing at her temples stopped as her chair was spun around to face Captain Dread Beard. "Ahhh. I get it. You see, when my boys do good work, they get to have some fun with the spoils." A large hand underneath Angelica's chin forced her to look up at Dread Beard. "Ya saw the worst of it, did'gya little Angelica? Then I suppose I can skip ahead a bit." Angelica gasped as the pirate roughly reached out and pulled off her petticoats, tossing them to the floor. "Wh-What are you..?" She squeaked out, but his imposing bulk filling her vision made her close her mouth. "Quiet, luv. I want ta get a proper look at'chya."

Angelica shivered as Dread Beard grabbed her by the biceps and pulled her to her feet, finding the buttons along her back and undoing them swiftly. Before long, her expensive dress dropped to the floor, and Angelica was roughly turned back to face him standing in only her bloomers. She blushed shivering in the cold room as the man eyes up her young, thin body, up to her tiny nipples perking up in the cold. "Near flawless skin... An' still washboard-flat." He grabbed her small head, peeling her lips aside to get a good look at her teeth. "Got all of em' in there. A real lady, I see. You bled down there yet?" He pressed a knee against Angelica's groin, making her gasp. "B-Bled..!? I..." The hand around her head squeezed just enough to be uncomfortable. "Answer me, lass. I tolerate no disobedience from them in my care." She blinked, but something about the intensity in his eyes made her resistance fall away, and the little girl swallowed hard. "N-No... I h-haven't had m-my first b-bleed yet. M-Momma said she thought it would b-be soon..." Tears welled up in her eyes as she thought of her mother. A knot in the pit of her stomach told her she was never going to see her again.

"No man ever stuck in here, neither?" Angelica's eyes widened as Dread Beard yanked her bloomers down to her petite thighs, her milky white skin now completely on display for the big pirate captain, along with her bald, childish vulva. "N-N-Nooo...." Angelica shuddered, her mind showing her images unheeded of what the men did to Veronica earlier that night. Dread Beard forced her to turn around, bending her over the chair as he grabbed and pried her butt cheeks apart. "And how many years of age, be ye?" Another tear rolled down the little girl's cheek as she answered mechanically. "10 years..."

"A tender age for a young lass. Most of my men don't appreciate little treasures." Angelica began to sob as the big man held her down, shifting behind her to unbutton his trousers. "Me, I like em the most. The tender, small things that most people overlook. The smallest jewels often the things most folk value the highest." She felt something warm and long flop against her lower back. "P-Please... I don't want to..." she sobbed. "Quiet down, lass. I ain't going to take yer father's greatest treasure, that he tried so hard to protect." A large finger pressed against her vaginal entrance, teasing along the tiny slit. "Not yet, at least. But yer not broken yet, an' we can't have that." Angelica felt the pirate's thumb press against her tender plucker, her eyes going wide as he pushed it past her delicate ring piece. "But there be other small, tight places in ya that I can find pleasure in." He pumped his thumb in and out of her anus, losing her up a bit as Angelica sobbed.

"Calm yerself, child. I won't be throwing ya to my men, if that's yer worry. Ya won't have ta worry about them if yer mine." The finger withdrew from Angelica's quivering butt hole, as the captain pried her cheeks further apart. She shuddered, feeling him pull back and the head of his cock press against her tender opening. "C-Captain, p-please noooo...." Angelica wanted to run away, but there was nowhere for her to go. As if sensing her intentions, a big hand pushed down on the small of her back, pinning her in place more firmly. "That's good... ya call me captain. I'm yer captain now." The thick head of the big pirate's cock forced its way past her plucker as Angelica sobbed, stretching out her rectal passage as he forced more of his length into her. "Bounties of the flesh like yers are what I be most interested in." The intimidating pirate grunted as he bottomed out in Angelica's tiny bum, his balls slapping against her hairless pussy as her knees trembled.

"It h-hurts..." she sobbed and a big hand slapped her on the back of the head. "Ya call me captain, brat!" Angelica squeaked and shivered, her face pressed hard into the lime green cushion on the chair. "Y-Yes, c-captain..." she sobbed as he began to pull his length back out of her. "And as yer captain... I get what I want from ya." The cock slammed back into her tight rectum, making little Angelica cry out. "And I get it, when I want it. We clear, miss Angelica?" The little girl nodded weakly into the course cushion as he began fucking her ass, his huge adult cock stretching her tight little hole out painfully. "Y-Yes, c-captain... Sob..." The big pirate grunted, squeezing her little rump with one one big hand as he rammed into the little girl, her bare knees thumping painfully against the wooden chair legs with each hard thrust. "Ya know yer place, and I don't have ta hurt ya. Ya get fed, a place ta live, and ya get to be grateful 'fer it."

Angelica's small face screwed up as the pirate captain picked up his pace, giving her pale bum a light spanking every now and then as his cock continued pistoning inside her bowels, rubbing her insides in a way that made her feel odd and squirm. "I keep a tight grip on my little treasures, so don't even think about tryin' ta run away. I will make ya sorry if ya try." Angelica shuddered, feeling the thick meat in her ass starting to throb as it forced its way inside what was normally a one-way tunnel, her brain blocking out some of the intense pain she was feeling. "Y-Yes.. c-captain..." she sobbed under her breath. A hand on her hair made her yelp, bringing her back to the pain in the present as her head was yanked back painfully, the cock in her anus convulsing as Dread Beard came hard up her little butt, pumpint it full of his warm, sticky cum. "Glad we can come to an understanding, little Miss Angelica." He whispered in her ear as he pumped against her a few more times, more hot cum gushing into the little girl's rectum.

He held her there for a moment longer before letting go of her hair. Angelica's head thumped back down onto the chair cushion as the pirate yanked his cock roughly out of her bottom, her gaping anus oozing semen as he grabbed her by the neck and forced her to sit in the chair. "Stay." the man commanded, meeting her eyes and squeezing before letting go. Angelica gasped, her butt still throbbing painfully as Dread Beard went behind his desk and opened a drawer near the top. Walking back over to her, he held out the gold-plated chain and clasp to her intimidatingly, before grabbing the little girl by the hair and pulling her over to the red-silk couch in the corner. Angelica stumbled and nearly tripped as she tried her best to follow him quickly to lessen the pain in her scalp from the hair pulling, but the bloomers around her thighs almost proved her undoing. The two girls on the couch suddenly moved as they approached, the one on the left sitting up and opening her legs wide to spread her tiny pussy while the other girl bent herself over and spread her ass cheeks towards them.

"See how obedient they are?" Dread Beard sneered as he pushed Angelica down onto the couch, grabbing one of her hands painfully and locking the golden manacle around it, before kneeling down to chain the other end to a metal loop underneath in the couch. "These two are proper broken, and know their place. You will learn ta be like them." Pushing her down with a hand on her belly, Dread Beard grabbed Angelica's little legs and tugged her bloomers off over her small feet, following by removing her thin socks and the one slipper she had left. "Clothes are a privilege for my little treasures, and one you do not get until you earn it."

The big pirate got up onto the couch, kneeling over Angelica as his manhood hardened again. As it poked into her cheek, her nostrils flared from the strong musty smell coming from his groin. "Open that pretty little mouth of yours." He smacked her on the head, bumping her wound and making Angelica cry out. She opened her mouth obediently, and Dread Beard thrust his thick member inside, grabbing handfuls of her head to yank her little head forward with. "Clean it off with yer mouth, brat." His cock slammed down the little girl's throat, cutting off her air. She gagged, and he pulled back and slammed it down again. "This be what yer good fer, Miss Angelica. Do ya think that husband yer father had planned fer ya in yer future would do any different?" She cried again, thinking of her father as the big man raped her mouth, grabbing her chin to yank her head painfully forward. She had just enough time to get a little air in between his savage thrusts, her little head jiggling in his grip as he pleasured himself with her tiny mouth.

The big pirate captain fucked her mouth for a good while in silence, forcing her to look him in the eyes as he did it. Angelica's mind felt hazy as she stared into his scary face, barely even registering when he began cuming down her tight little throat until she reflexively swallowed his load. The big man let go of her hair as he yanked his cock out her mouth, letting Angelica gasp for air and cough for a moment before grabbing her chin again. "Now lass.... I trust I made myself... as clear as the sea be dark." Angelica didn't respond right away, but weakly nodded after he gave her head a little shake. "Good. Now..." He let go of her chin and picked the little girl up, sitting down on the couch and placing her in his lap.

Angelica flinched as his big hands went back to her shoulders, but he began to massage them again as he'd done before as she sat naked and shaking in the pirate captain's lap. "Ya did good... Not a hard break, so ya get ta walk away mostly unbruised. This one..." he nudged the girl still spreading her ass on their left, and she let go of her bottom scooted over towards him so he could grope her rump. "...This treasure took a week to break, an' sadly I had ta break her some." He made Angelica look at the whip scars on her back, and she shuddered. "Ya won't give me that kind of trouble, now will ya, lass?" Angelica shook her head quickly. "N-N-No, c-captain..!" She stammered, fear spiking through her once again. The big pirate cupped her chin and kissed her lips softly for a moment.

"Good lass. Ya listened well, so I will reward ya." He placed a finger on Angelica's petite slit, and she tensed up again. "Relax, child. I meant what I said earlier, I not be shoving it in there fer now." His big finger traced the line of her little pussy up and down gently, sending a different kind of chill shooting through Angelica as she shuddered. "Yer flower has other ways ta reward you." Pinching at her folds, he pried her tiny pussy lips apart, revealing the little girl's underdeveloped clit. "Now this here be a key... a key to opening many pleasures." Dread Beard pressed his thumb down on her little bean, making Angelica gasp as a shock of unfamiliar emotion raced through her body.

"Ya see, me treasures that be good get a nice little reward." The girl next to Angelica began to quiver, making her look over at her. The girl's slit between her legs was dripping wet, and little whimpers escaped her mouth. "She was not good." Dread Beard told Angelica as he pressed his thumb firmly against her little clit and began to rub, making the little girl let out a high pitched moan. "This treasure down here... it belongs to me. If I catch you tampering with it... well, there are consequences." He roughly spanked the bottom of the girl beside them, making her yelp. "She doesn't get to feel the pleasure till she pleases me again, though her body craves it." The big man rubbed Angelica's little bean in circles, sending waves of unfamiliar pleasure shooting into her young mind. "Y-Yes, c-captain... I... u-understand..." Angelica whimpered, her little hips starting to buck unconsciously.

"If yer good, ya get to feel the pleasure. And if yer bad..." He reached out and slammed his palm down on the other girl's bare ass as hard as he could, making her sob out in pain. "...Ya get to feel the pain. Remember that, lass." Leaving the other girl trembling, he brought his free hand back to Angelica and up to her childish chest, pinching gently at one of her tiny erect nipples. “C-Captain..?" Angelica whimpered, feeling something building up inside of her that scared her as much as it excited her young mind. "Yes, my dear. You're getting close..." She could feel his hot breath on her neck as he whispered in her ear, making her shiver. "Don't deny yer pleasure: embrace it." Angelica let out a squeal as she felt something pop inside her, waves of intense pleasure washing through her as a liquid squirted from between her legs onto the cold deck planks. Her little hips bucked as she had her first orgasm, bucking against the captain's hand. "That's a good little lass... now ye have experienced the greatest treasure in this rotten world of ours - the pleasure of the flesh."

Captain Dread Beard gave Angelica's flat belly a few pats before wiping his wet fingers dry in her hair and pulling her off of his lap. "I must attend to the crew, Miss Angelica. Ya will be safe in here. Do as you have been told, or I will know." He tossed her bloomers back at her, picking up the rest of her clothes and putting them away in a cabinet up against the far wall. "Ya may wear those, if ye wish, but nothing else." The captain walked over to lightly slap the other two girls on the couch on the backs of their heads. "You two. You may give her pleasure." He grabbed the disobedient girl by the hair and drug her up to eye level. "Your ban on pleasure is off. And you misbehave again, the next thing I cut won't grow back. I grow tired of coddling you, brat."

Angelica stared at the clothes in her hands as the captain left the cabin, before slowly sliding the bloomers back up her thin, pale legs. She stopped at her groin and stared at it, seeing her little slit looked looser than before as it continued twitching and giving her little jolts of good feelings. Blinking, she pulled her bloomers back up over her bottom and sat, shivering in the cold room.

As she pulled her thin legs up to her equally thin chest, the two girls chained next to her sat up with her. Angelica blinked as the girl to her left plunged her fingers inside her pussy and let out a lewd moan, sliding them in and out for a few moments before she shuddered and squirted as Angelica had. Withdrawing her fingers, she licked them before letting out a sigh and finally looking at Angelica. "So you're his new one?" The girl on her left that the captain had beaten drawled. "Lucky you. I'm Irina, by the way, 'Miss Angelica'" her deep voice dripped with sarcasm as she said the girl's name. The girl had heavily tanned skin dotted with freckles, and a stockier frame than Angelica's lanky form, and looked to be maybe a year older. Her dark brown hair was cropped shorter just under her earlobes, framing a mulish face set with emerald green eyes. Scars and whip marks covered her arms, legs, back, and even a few on her chest, belly, and groin. The only clothing that she wore was a thin green wrap that sat about the shoulders, leaving every modest bit of her bare and exposed.

"Don't be so hard on her, Iry. It's not like she had a choice." The girl on her left put a comforting hand on Angelica's shoulder. "Irina was his favorite before you... just as I was before her. I told you he'd find a new 'treasure' eventually, Iry." The disobedient girl stuck her tongue out at the kind-hearted one. "I'm Haley, nice to meet you, Miss Angelica." Angelica looked over at the girl with her hand on her shoulder, whose voice carried a hint of an accent she could not place. She looked to be maybe two or three years older than herself, with skin less pale than her own, and long black hair, framed around a round face and stunning amber-colored eyes. The girl's skin was mostly unblemished, save for a mole on her left hip. Gem-studded piercings thrust through nipples on budding breasts. An onyx belly button stud drew the gaze to her navel, and the girl had several words etched onto her flesh in black, tattooed ink. Angelica, educated as she was, could read the one over her groin as "Dread Beard's Little Treasure" and shuddered.

"Hmm? Oh right, you're a proper lady - that's what captain said. Does that mean you can you read what it says?" The girl Haley spread her legs open and turned her torso to give Angelica a better look. "He never told me what he had written on me." The little girl swallowed, seeing how battered the girl's pussy lips looked. "Y-Yeah. It says... Dread Beard's Little Treasure". Haley slumped back a little at this. "Oh... Is that all? I always imagined it was something more... special." Irina snorted. "You think too highly of yourself, Hal. We're just his toys, you know."

Haley frowned at her counterpart. "Why can't you just accept what the world has given you, Iry... Captain wouldn't hurt you so much if you stopped trying to escape." Angelica looked over at the older girl, swallowing a lump in her throat. "Y-You tried to escape...?" The mulish girl sat back on the couch, putting her arms behind her head. "Yeah, plenty of times. He always catches me, though... I dunno how he does it." Angelica's heart sank at hearing this. "A-And how long have you two b-been his... treasures?" Irina spat on the floor. "I don't remember. I think... two years maybe?" Haley scratched an itch on her belly, making the gold chains clank. "I think it's been four years for me, but it's hard to keep track out at sea." Angelica felt more and more defeated with each word from the two girls. How would she ever get back to her father if these girls hadn't managed to escape in several years?

"You might as well get used to being here." Irina said with a smirk, making Haley put her hands on her hips. "Oh? Does this mean you're finally done trying to escape, if you're telling our new friend here to not try? You know how much I hate watching him hurt you..." Irina shook her head, sticking her tongue out at Haley. "Nope. Not me. But this delicate little lady here, she's got no chance of getting out. He barely even put it in her before she broke. Sooooo weeeak!" Angelica puffed out her cheeks in annoyance at the remarks. "I just lost my father and saw a lot of people die, okay? He cut off his hand! I was scared!" Irina snickered at the younger girl. "Oh, is that all? You lost your father? That's not nearly as bad as what he did to my family." Her sarcasm was almost palpable. "Having them burned alive in front of me and making me watch while he shoved it inside me." Angelica sat back in shock. "I... I'm sorry, I didn't mean..." Her voice trailed off as Irina stared at the ceiling. "I'll get my revenge some day, you'll see... He'll get what's coming to him..."

"I was lucky then..." Haley announced after the silence grew too long. "He picked me up off the streets of a town he was burning. I don't remember my family. This is a much nicer place to live..." Angelica shivered again, looking down at her hands. The gold-plated cuff drew her gaze, and he put a hand over it. "I'm surprised he didn't just... you know..." Haley's voice broke Angelica out of her daze. "Didn't what?" she asked, looking into the girl's eyes. She reached down and touched Angelica's groin through the thin cotton of her bloomers. "Didn't shove it in there. It's the captain's favorite hole." Angelica flinched as the older girl's finger touched her reddened slit. "Yeah, so 'little miss special' over here didn't get her pussy stuffed. So what? He'll probably do it tomorrow." Irina sneered, making Angelica shudder. "D-Do you th-think he w-will...!?" She stammered, and Haley leaned across her to give Irina a light swat on the thigh. "She's been through enough, Iry. Give her time to get used to things, stop trying to scare her more."

Irina rolled her eyes. "Well anyways, no sense in getting in trouble when I can't try to escape." She suddenly reached over to Angelica and grabbed the waistband of her bloomers, yanking them down. Angelica yelped, trying to cover her groin. "Wh-What are you d-doing..?" Irina gave a hooked smile. "You heard the captain. We're supposed to 'give you pleasure'. Lucky bitch." Angelica tried to pull her bloomers back up, but Haley laid a gentle hand on hers. "Iry is right, we do not defy the captain. He will know..." She gently eased Angelica's hands away from her groin. "I will go easy... come here, let me teach you some things." Haley cupped Angelica's cheek before she could protest, and planted her lips on the younger girl's, sliding her tongue inside Angelica's mouth. The little girl blinked, feeling her cheeks flushing with warmth as the older girl kissed her softly, her lips working against the other girl's. "Well I'm not going on easy on her." Irina's gruff voice cut through Angelica's poleaxed state as she climbed on top of her, kicking her bloomers down to her ankles as Irina stradled Angelica. The little girl gasped as Irina began to bounce up and down in her lap, smooshing their pussies together in a way that sent a jolt of pleasure up through her.

Haley broke the kiss to scowl at her friend. "Iry, why must you be so mean... she's not going anywhere for a while, you should make friends with her." Irina grunted as she humped away at Angelica's groin, making her feel weak and breathless. "I'm not being mean... I'm teaching her. You think HE will be gentler?" Haley sighed and held out her index and middle finger, putting one of Angelica's tiny nipples between them and squeezing them closed gently. "There are several places to feel pleasure... The one down between your legs, your breasts here... and kissing is another." She kissed Angelica again, tilting her head back. "Yeah, yeah. Pleasure here, pleasure there." Irina grunted, Angelica shuddering at feeling wetness between their smooshed together groins. "The least the new girl can do is get me off if she's gonna be sharing our couch." Irina grabbed one of Angelica's legs and bent it up at the knee, sliding her own leg over her belly so she could grind their pussies together closer and harder. Angelica let out a moan as Haley broke the kiss, gently licking down her neck towards her nipples before beginning to suck on them. "You know, you're pretty fun to squish against. Hal doesn't react enough." The older girl looked up from her nipple sucking to scowl at her counterpart. "As if it is not my fault I do not have much.... sensitivity down there anymore..." Haley's mouth went back to Angelica's nipples, sucking more aggressively this time.

The little girl let out a squeak just as the cabin door opened, and Dread Beard walked back in. Angelica froze, and Haley looked back at the door, a thin line of drool still connecting her mouth to Angelica's chest. Irina did not so much as slow her scissoring attempts as their captain entered.

"I did not tell ye to stop when I enter." Dread Beard drawled, making Angelica shiver as Haley quickly went back to sucking on Angelica's swollen nipples. "Ye had orders - finish them." Angelica let out a squeal, feelings that same building sensation inside her as Dread Beard walked over to them, unbuttoning his trousers. Pulling out his cock, he gently stroked it as he watched his two older pets fuck his new one. Angelica let out another squeal as she felt her orgasm hit, waves of pleasure crashing over her as she came hard. Dread Beard roughly grabbed Irina by the neck and pulled her back, shoving her face down into Angelica's crotch. "Drink." he commanded, and Angelica shuddered, feeling the girl's tongue lapping at her folds while she squirted into her mouth. Letting her up when she was finished cumming, Haley pulled her head back from Angelica's nipple and gave her one last, lingering kiss before sitting back on the couch. Haley looked up at Dread Beard, hesitantly asking, "Captain, may I...?" Dread Beard leaned over and traced a finger up her belly to her chin, making her shiver happily. "Ye did good, Haley. Ye may finger yerself once." Haley bowed her head, reaching for her groin to slide two fingers inside, moaning happily.

As little Angelica pulled up her bloomers and lay back panting, Dread Beard reached down with a tiny key and unlocked her chain from the couch. Lifting her in a princess carry, she looked up at him with wide blue eyes. "Ye will sleep with me tonight, treasure." He told her as he walked over to a hole in one of the walls covered in drapes, ducking inside. A four poster bed with silky red sheets and a small drawer next to it were the room's only features. Angelica gulped and squeaked out, "Y-Yes c-captain..!" Kicking off his boots, Dread Beard set Angelica down on the bed, before locking her chain to the headboard. Unbuckling his weapons belt, he hung it up on the far wall out of reach. Shrugging off his thick coat, he climbed into the bed with her.

Leaning down over her, Dread Beard pressed his face into her belly and inhaled loudly, raising goosebumps over the little girl's pale skin."C-Captain..?" Angelica stammered, unsure what he was going to do with her. Pulling his face away, the pirate grabbed the waistband of her bloomers and tugged them down to her ankles, tossing them off the bed as she blushed. "It's time to finish yer breaking in." Angelica shuddered as he pressed a big finger against her plump little pussy. "B-But..." Angelica stammered, wincing as she saw a look of displeasure contort the man's face. "I'm s-sorry, captain! I'm s-sorry!" A pat on her belly was the only thing that followed her outburst. "That's more like it. Ya get it now. I don't proper care whatch’ya want, treasure. Yer mine." He unbuttoned his trousers once more, shifting so the big man could pry the little girl's legs apart, rubbing his cock up and down along her tiny pussy. "Yer never going to see yer family again. This be yer life now, Miss Angelica. And so..." He pushed the tip of his cock down, the tip of his manhood parting her tiny lips as she shuddered. "...I take from ye what no one can give ye back. Yer chastity." Angelica's knees trembled as he sank and inch his throbbing member into her tiny cunt, spearing her open as her pussy stretched open wide to fit his girth.

Sweat formed on Angelica's skin as she gasped, feeling a pain in her groin as he pushed before bottoming out as something blocked his way. Staring the little girl directly in the eyes, the big pirate grinned. "And now, it's mine." With a single forward thrust, Angelica's hymen tore, making her scream. Dread Beard kept pushing past her popped plug, until the tip of his adult cock kissed her small cervix, the bulge of his manhood on her tiny belly plain as Angelica looked down at where he'd speared into her with tears in her eyes. She could see a little blood flowing out from around his member as she began to sob. "Yer mine now, Miss Angelica. My little treasure." Dread Beard began to piston in and out of her battered pussy, sending shuddering waves of pain mixed with pleasure shooting through the little girl. "And few tonight, yer my bed mate."

The big pirate's thrusting became faster as he forced his cock inside her, Angelica shuddering from the feeling of being so thoroughly stuffed. Dread Beard leaned in close to her face, not ceasing his pounding of her little womb as he stared wide eyed at her. "I'm going to mark yer insides, little lady." He grunted, his dick throbbing inside her. "Ye will spread your legs fer me like this anytime I ask, ye got it?" Angelica nodded, her vision blurred with tears as Dread Beard grabbed her by the waist and began slamming even faster, his cock stuffing in and out of her tight little hole. With a howl, the pirate captain came inside his little treasure, thick, hot semen gushing into Angelica's tiny womb as he filled her belly up. "That's my treasure... ahhh!" He gushed a few more strands into her, before pulling his cock out and shooting one final string onto her belly.

Angelica only lay there on her back, panting hard after the brutal fucking. Cum oozed from her pussy as her belly muscles convulsed, dripping onto the bed sheets to join the other cum stains there. Dread Beard pulled her tight into his arms and spooned the little girl, rubbing her head like a child with a favorite dolly as she finished sobbing.

"Ya did good fer yer first time..." Her whispered in her ear a few minutes later, making Angelica shiver. she could feel his thickness hardening again already as it pressed into her bare bottom. "But I not be satisfied yet...!" With a shudder, she felt him put a hand on her thigh and pull it up so he could slide it cock between her little legs. "Ye can take another load." The large rod forced its way back inside her little pussy, making Angelica groan. Dread Beard began fucking her fast and hard almost immediately, his stamina ridiculous. Angelica gasped as he nibbled on her ear with his cock still slamming into her belly. "Yer going to be in my bed every night from here on out. Tell me, how does that make ye feel?"

Angelica sobbed, feeling so dirty and used like this. "C-Captain..." she stammered out, not sure what she could even say to that. "I know, luv. It makes me want to..." He spasmed again, beginning to paint her insides once again with his semen. "...fill yer belly full of my seed. Again, and again. And Again..." Angelica squeezed her eyes shut as she felt him inseminating her again. The big man's mouth clamped on the flesh around her tender nipples where he bit hard enough to leave a bite mark. "I luv marking me treasures."

His cock yanked out of her again as Angelica's eyes glossed over. She lost track of the time he held her before getting hard one more time, and pushing her down onto the bed to lay flat on her belly. Dread Beard lay on top of the little girl, grabbing his cock and forcing it inside her little butt again. Angelica could barely feel the cock bottoming out in her tight rectum, she was so out of it at this point, and as he began pumping in and out of her tight rectum as her bottom jiggled, she only had one thought in her mind. A voice echoing over and over in her brain, saying one thing: "This is my life now."