Good morning team, and happy Thursday! For today's treat, please enjoy Ch. 2 of my epic pirate drama/romance, The Black Flag! Warning: this chapter does not end well for Captain Black. Pay attention to the tags, please! This story is a Harbinger96 original and is not to be shared or reposted without my permission. All characters involved are 18 or older. All characters are fictional and any names in relation to real people are coincidental.

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The next morning, Hailee woke to the sound of gulls and the happy cries of a crew that were as loud as any cannonade could be.

The brunette captive opened her eyes and saw that Captain Black was already gone. The only sign that she had been there at all was a single orange on a small writing desk. The Captain didn’t strike Hailee as a writer or reader per se, but Hailee was going off of stereotypes here. She didn’t know the captain. Had she taken a minute longer to snoop, she would have discovered that notorious Victoria Black was a gifted poet.

Hailee slowly got up and rubbed a hand over her pussy, trying to pick up residual feelings of last night to see if it had really happened. The images and sensations from the previous night were fresh in her mind, and the recall available to her made her all tingly again. She was a proper lady. She wasn’t supposed to like what had been done to her, let alone been a willing participant. She told herself she didn’t have any choice in the matter, but she had to admit to herself… she did like it, and that alone made her cheeks flush.

The wayward lady picked up the orange and went back to bed, wishing to enjoy her tasty fresh citrus in peace, but also a little more than frightened to leave the safety of the cabin. She was under the captain’s protection, but a ship full of dirty, violent pirates was still a daunting thing.

Hailee wasn't alone long, for the stately wooden door quietly opened and Victoria slipped inside, quiet as a mouse. She could be a ghost on her own ship when she so wished.

"Oh good, you're awake," the little war criminal said, closing the door behind her with a pleased smile on her face. Her long and silky brunette hair was down and caressing her back, her Spanish ruffled shirt only half-way buttoned, exposing cleavage Hailee had to make herself look away from. She was a proper lady, after all. Or, still trying to portray one. The more time she spent with the captain, the more she was having second thoughts about who Hailee Hartman was actually supposed to be.

"Good morning, Captain," Hailee said shyly, aware of her nakedness, and remembering the captain's order from last night. She wasn't to hide her nakedness from the captain, and if one of them was undressed, Hailee was to use Victoria’s proper title.

"You found your breakfast as well," Victoria observed as she sat on her bed next to the taller girl, her brown eyes flitting from the fruit to Hailee’s mouth. "We're making port at Nassau today."

"Nassau?" Hailee asked, her eyes widening. I'm staying on the ship, right?" Hailee had heard rumors of the notorious pirate fortress and “society.” It was a den of corruption, villainy, sin and all kinds of deeds that would land you squarely in Hell when you died. Hailee was curious to see if it fit the legends, but she was not interested in risking her safety to see it.

Victoria laughed. "No you are not. Also, I and God only know when we'll dock again, so you best come with us," she said as she ran a finger along Hailee's chin and bottom lip, collecting some dribbling orange juice left from Hailee’s first dainty bites.

Hailee opened her mouth to speak, but Victoria slid the juicy finger into Hailee's mouth like a practiced lover. The act along with the sweet citrus taste made Hailee close her eyes and moan. Hailee wasn’t proud of the way Victoria could so quickly unravel her, she was quite mortified by it, in fact.

"Good morning, Princess," Victoria purred, running her fingers through Hailee's tangled bedhead, a gleam in her eyes, falling just short of a promise, but conveying what she would like to do to Hailee if only they had the time.

"Good morning, Captain," Hailee dreamily responded once Victoria had slid her finger, now clean, from Hailee's lips. The governor’s daughter’s cheeks flushed crimson and she looked away, having heard how needy and vulnerable she sounded just then. By God, what was Captain Victoria Black doing to her?

"I've a friend in Nassau I want you to meet, anyway. She's a skilled musician by the name of Rachel that I know will adore you. She's the only proper lady on the entire fucking island, and unless I am by your side, you are not to leave hers."

"I'll be happy to meet her, then," Hailee nodded curtly.

"I also owe her a debt which I'll be paying."

"May I ask how much you owe her?" Hailee ventured. “What’s the nature of the debt?”

"It's not a monetary debt, my dear.” The wolfish smile that overtook the captain’s face was enough to stop any kind of helpful thought Hailee had been trying to have. “I'm paying her back by giving her a night with you."

Hailee's jaw dropped. "You're whoring me?" she asked incredulously. Was Hailee to be passed around and used for turning tricks? What happened to just sitting tight and waiting to be ransomed, she wondered.

"Only to Rachel," Victoria said in a nearly defensive tone. "And besides, I promise you'll love her. She's more of a giver than a taker anyway." Victoria smiled a little softer this time, but she was still enjoying the fluster and frustration running along Hailee’s pretty face.

"It's not like I can say no, regardless," Hailee said, giving in to her fate. "If I don't do what you'll say, you've told me every person on this ship will have me, and that is not something I care to endure. I’m not sure I could. The chance of me passing away from pain, fright, or humiliation are all very real," she said in a chuckle, but in her breast she felt it to be true.

"I promise, Princess, you'll enjoy yourself. I will never whore you out to someone I think would hurt you," Victoria assured her new pet, kissing her forehead. "Do this for me, and you'll be even less likely to sit on a cock at my command. Unless you find yourself wanting one, that is," she laughed, pulling the sheet away from Hailee’s nude form and running her index finger around Hailee's opening a single time in teasing, but it was enough to make the heiress moan. Hailee hated how responsive she was in that moment, and all the moments from last night as well.

As the crew of the Gambit secured her to the docks, Captain Black, Hailee, and Mr. Lucious prepared to go ashore.

"Listen to me carefully, Hailee," Victoria said, grabbing the young woman by the shoulders. "As soon as we touch land, I have some business to take care of. Mr. Lucious will escort you to the White Hall Tavern to meet Ms. Hardy. I will rendezvous with you there. It may take me a while, but Ms. Hardy will make you feel at home." With that, Victoria took a head start and took off, leaping from the safety of the Gambit with a rope, and landing expertly on the dock. Victoria did like her entrances to have flourish.

Victoria was barely out of view from her own ship before she was roughly grabbed by two hulking Black men. She knew immediately who they were, who they worked for.

"Well well, if it isn't Captain Victoria Black," a smooth like brandy but still teasing voice said from behind the struggling captain.

Victoria relaxed and shook her head. "Good noon, Ms. McIntyre," she said calmly. "I was just on my way to see you."

"I've no doubt," the criminal mastermind said with a laugh. "The Gambit doesn't look too low on the water, Victoria," Katherine McIntyre whispered in the captain's ear, the task made easy by them being the same height. "How are you supposed to pay me back for the Gambit if you're not bringing in prizes?"

"I'm really close to getting you a massive prize, Katie, I promise," Victoria tried to convince the older Irishwoman, who had just snapped her fingers and began leading the trio to a warehouse just off the beach. The McIntyre family owned half of this particular wharf. "Oh come on, Katie. I just need a bit more time. We don't have to do this!"

"I do, Victoria. I need to remind you what happens when you don't pay your debts," Katie scolded the elusive Puerto Rican. "If you don't pay me in gold, I'll pay myself by taking delight in your flesh," the smuggler queen said, pushing open a pair of large wooden double doors, and then closing them once everyone was inside. "Boys, over there," Katie instructed, pointing to a large hook hanging from the ceiling.

The massive Africans tied her hands together with a hemp rope and tugged her slender arms over her head, hanging her to the great hook.

"Can't we talk through this, Katie? Up my interests or something?" Her pleas fell on deaf ears as one of the Africans tore her blouse right down the middle, exposing her firm tits and mocha colored nipples.

"My God, I forgot how good you look naked," Katie said, licking her lips as she stepped forward and cupped Victoria's pear shaped tits in her hands, admiring her flat stomach and the flare of her hips under her signature black leather pants. "I've missed this body," she said as she dropped a hand to cup Victoria's crotch. "I'm going to taste this pussy, and we'll take a few pieces of eight off the tab, yeah?"

Victoria spat, but Katie knew her prey too well, opening her mouth and catching the spit, only to spit it on her own fingers and spear them past Victoria's waistband, feeling her soft lower lips.

"God, I hate that I like your fingers," Victoria groaned, torn between trying to pull on her restraints or whether she wanted to hump the fingers that were slowly working their way into her dampening, squishy core. This situation was a reminder to the captain that not so long ago, she was far more like her soft Hailee than she was now.

"I know you do, darling," Katie said soothingly, kissing her neck. "Don't forget who first showed you how to use that sweet mouth, who first spread your legs, who taught you to eat pussy." Katie snapped her fingers, and in seconds, Victoria's boots, pants, and britches were all cast aside without Katie's finger leaving Victoria's sweet cunt.

"How could I forget?" Victoria asked in a breathy voice, giving in to base needs, rolling her hips into Katie's hand. Katie was all too happy to grind her palm into Victoria's clit, making herself smile at how wet she had already gotten the notorious pirate captain.

"But unfortunately, I'm not here to slowly draw you to orgasm, my pet," the green-eyed goddess said, slowly drawing her fingers out of Victoria's tight hole and rubbing the wetness on the pirate’s cheek, leaving a glistening streak on her soft skin.

"What? Why not?" Victoria asked, pretending she didn't know why Katie brought the biggest men she could find with her. Her having been stripped and (mercifully) warmed up was also a pretty telling sign.

"Because these gentlemen here are going to discipline you for not having my fucking money," Katie told her, sucking what was left of Victoria’s taste off of her long, slender fingers. "Do whatever you want to this Puerto Rican bitch, boys."

Katie took a few steps back and opened her own shirt, playing with her rosy pink nipples with one hand, and undoing her cotton slacks with the other to pleasure herself as she watched the two bulls strip themselves.

They added slack to the rope, pushing Victoria down to her knees, but had the decency to ball up the discarded clothes beneath her.

"Gents, please, you don't have to do this!" Victoria begged as she watched them stroke their massive, dark dicks. Victoria was far from a blushing virgin, but she wasn’t a fan of getting lockjaw.

"Shut the fuck up and take it, Vicky. This was a normal Saturday afternoon for you when I set you to work in that Barbados whore house," Katie scolded, two fingers as deep in her own pussy as she could get. Katie wasn’t much in the business of doing the dirty work herself anymore, but watching scenes like this was where she took her pleasure. It being that arrogant Victoria Black made it all the more delicious for her.

Victoria rolled her eyes at her former mistress as the two men were finally fully upon her, giant, rod-stiff cocks right at her mouth, pushing against her cheeks and lips. "Get a good eyeful, because you're about to learn that this Puerto Rican bitch still has it," she spat defiantly as she opened her mouth wide, taking the first dark purple tip into her mouth, her soft lips stretching to accommodate the sheer size of it.

Victoria immediately began moaning around the mouthful she had taken. Tears shamelessly filled her eyes as she swallowed down as much thick meat as she could. She gagged and pulled on her restraints, not in fight, no, but begging to be released. If she was going to do this, she wanted to do it right. A twisted part deep inside her wanted to prove she could still fuck and suck from the bottom up. The best weapon she had to piss off Ms. McIntyre would be to actually enjoy this.

"Let her down, boys, she's already lost in the cock," Katie said, flicking her clit from her viewing chair. “This is your lucky day, gents,” she laughed.

The hands did as ordered, and the one with the unsucked cock untied her hands. As soon as they were free, Victoria wrapped both small but practiced hands around the pillar of man in front of her and started jacking with all she had.

The first man pulled out of Victoria's mouth with a groan, already missing the golden throat, but knew his partner needed a turn. His spit soaked cock would feel better in her hands than the dry stroking his friend had started out with.

"Gimme that cock," Victoria ordered and sucked in the dry cock with ferocity, her hands going fast and forcefully on the precum and spit covered staff she had just been gagging on. She didn't try to control the wet, lewd sounds emitting from her face and throat.

After a few moments, Katie clapped her hands together. "Enough foreplay, boys. It's time to stretch that pussy. Don’t be gentle, either."

"Yes, Ms. Macintyre," one grunted, and yanked up Victoria by her wrists. “I’m going to enjoy fucking this bitch.”

"Wait a moment," Katie groaned. "We don't want to kill the bitch. Make sure she's properly wet for you monsters. I’m pretty sure she is, but you two aren’t here because you’re average sized."

"Aye, ma'am," the one holding her wrists said. Without any effort, he picked the girl up and flipped her over, and dropped his mouth onto her snatch, slurping greedily and making Victoria moan uncontrollably.

"Fuck, he's got a mouth on him. Oh God, that tongue!" she groaned and her eyes rolled back. She grabbed his muscled thighs for dear life as she was slobbered on and eaten out like she never knew she needed. It was loud, messy, wet, and completely without control or focus. Victoria decided not to slouch and sucked on the cock right in front of her.

The large Black man fell prey to Victoria's wiles, and fucked her tight throat, thrusting and pounding her airways until he came, which Victoria happily drank down, bobbing her pretty head in time with the spurts of cum shooting out of him.

Cursing to himself and trying to keep his footing, he put Victoria back on her feet, her own knees shaking, a sadistic and pleased smile on her spit-sheened lips.

"Thank you very much, sir," Victoria said with a laugh, giving his dick a goodbye tug. “That was tasty. Such a good sized load!” she teased, and Katie snarled. She underestimated the depraved slut that Victoria could be.

"Now that you've spent your load, get over here and put that mouth on me, you stupid git," Katie ordered, standing up long enough to strip herself bare and then taking her seat again. Victoria had to steal a quick glance at her mistress's body. Katie was ten years older, but still had a gorgeous frame, like a painting of Aphrodite, and a sweet Irish accent that betrayed what a cunning and cruel bitch she could be.

The last cock still standing got to his knees and pointed to the clothes pile before him. "If you'll get on your hands and knees, Captain, I'd be happy to bust your guts."

"If you must," Victoria sighed, doing as ordered, spurred on by Katie's moans coming from the side.

Victoria took position and waited to feel a swollen cock at her entrance, but her eyes went wide and she cried out "OH CHRIST!" as the giant slammed into her in one harsh thrust, filling her up. Katie laughed heartily as she enjoyed the enthusiastic pussy eating she was receiving on the sideline of the action.

"That's some tight fucking pussy, Ms. McIntyre," the man groaned as he dropped his hulking body on top of Victoria's petite frame, fucking her hard and fast like a dog as Victoria fought to stay on her forearms, crying out as she was taken on no terms of her own, that part of the battle lost. The man on top of her was too big, too strong for Victoria to do much of anything except take the vaginal beating.

"Fuck that pussy good, Mr. Moreau. Make her want to pay me," Katie growled as she humped the Black man's mouth between her legs, easily getting off on Victoria's punishment.

"Please! Please slow down!" Victoria begged as she fell down, her face pressing into her own leather leggings. "Stop, stop!" she cried, trying to use her hands to push the man's thighs away from her reddening, round ass. "Katie, please!" Victoria pleaded, her eyes widening with the fear of being bred. Having a Black man’s child, any child, while doing her line of work was something she could not risk. This was no longer a game for Victoria, and she was acutely aware she had lost this round. “You win, Katie! You win! Please make him stop!”

"Fill her up, Mr. Moreau. Feel free to empty your balls in that cunt. Remind her that she still belongs to me!" Katie shouted, now viciously thrusting her hips into the drowning face before her. Hearing Victoria surrender, listening to her beg was sadistic bliss to the jaded business woman, and she came hard, screaming herself from the harsh release.

"No! No!" Victoria tried, knowing she was well and truly fucked in all possible ways. "Cum in my mouth, on my ass, tits, whatever. Just not in me! Please!"

She couldn't see it, but the beast atop her shook his head vigorously. "Pussy feels too good, Captain. I gotta fill it up," he grunted as he released, filling Victoria with a full load, making the once-proud captain cry out in horror, pain, and despair. Victoria’s eyes shot open and gasped for air as the sensation of hot, thick seed filling her pristine pussy made her feel like the air in her lungs had been evacuated to make room for the copious load that had been deposited.

"Fuck you! Fuck all of you!" she bellowed as the Black man on top of her slowed his hips but kept them forceful, making sure she was good and packed with his seed.

"Maybe pay your debts on time and I won't have to make this happen again," Katie said, pushing the man in front of her away. She walked to Victoria's used and spent, sweaty body as Victoria went fetal on the ground, cum pouring out of her. "I'm sorry, little bird, but you have to learn," she said sadly before dressing herself and ordering that Victoria be left the room. “If you come back to Nassau without a payment for me, there’ll be more.”