Hoist the Colors

by Dark Apostle

Copyright© 2018 by Dark Apostle

Historical Sex Story: James William Smith in Nassau 1715, at the height of the Golden Age of Pirates. Based on the popular Black Sails and Black Flag series, respectively.

Caution: This Historical Sex Story contains strong sexual content, including Ma/Fa   Lesbian   Heterosexual   Celebrity   Fan Fiction   Historical   DoOver   Time Travel   .

Time travel. Through out science fiction there were many ways to do it, the first was obvious: create a time machine and go back in time. Others included magic or alien interference, sometimes, rarely even heavenly interference. For James it was magical: his deus ex machina had been a genie in a lamp just like Aladdin.

James William Smith had leapt into a new body and in a new era; this marked his fourth jump and fourth change. His previous body had died and now he was in a new host.

This time he had found himself in Nassau in 1715, at the height of the Golden Age of Pirates. His host was of a devilishly handsome young man. Upon arriving, he found he had had nothing, but then he had become a sneak thief, making a meagre living.

He met a young woman called Eleanor Guthrie and it was love at first sight - for him not her. James had become enamoured with her vivacity, humor and charm. However, despite her pulchritude, Eleanor was a formidable force in the local business scene. She was not just another pretty face. While James appreciated those attributes, it was Eleanor’s veracity that he found refreshing and the two had struck up an easy friendship.

At first the pirates of the era had ignored her but her cunning and ruthlessness had earned their respect. Wooing her had not been easy. In fact, it required a true long con. In the beginning, he had to find what she wanted and provide a tease for her, making her come to him first. James had sought out secrets, secrets that men wanted to keep quiet and that he could use to lure her in. She had learned through the grapevine about him. He used well timed discussions and the odd flip of the coin to ensure that word filtered through to her in dribs and drabs ... no grand gestures ... subtlety was required here.

She came to rely on him for information, whether she needed leverage on a pirate or if it were someone that needed to be handled in some way. And over time, she found herself relying on James more and more, just as he intended. Anyone who got in the way of his prize either found himself out of business or dead. James had no issue with killing; he was as cold blooded and heartless as many of the men who worked and lived in Nassau and he didn’t kill anyone of note, those who would change history he left alone.

He had recently ended up with a target, a man that was causing problems for Eleanor and the other captains as well. She refused to deal with them until the leak was plugged and James was tasked with finding said leak. It took weeks of work and subtle observation to figure who among them was selling secrets to the British. When James was absolutely certain, he located the man in question and followed him. His target was a middle-class, middle-aged man who was heading towards the docks. James followed this man with murderous designs. He moved through the dark and noisy streets of Nassau, brothels littered haphazardly along with bars and hotels. On the decks stood women with their tits thrust out, shouting at any potential passer-by who might be looking to get their dicks wet and lose some coin. The bars were full of drunken sailors, some pirates, some soldiers, some just guys looking for a good time, singing loudly in a tune only they understood. Tonight, they were all the same. There were no borders here, no skin color or religious differences, they were all out to get drunk and get some cunt.

He walked past a window and saw his reflection in the flickering light. Looking at himself, he couldn’t help but admire what he saw. At five feet eleven he was built like a sailor, lean muscle mass, fine features, dark serious eyes beneath messy dark blond hair. He smiled at his reflection showing perfect white teeth that made many a woman swoon. He turned away and headed down the street.

James had chosen a specific dress code, it was subtle and yet at the same time intimidating. He reflected the culture and idiosyncrasies of the time. He wore boots that had knives in them, in the soles of the boots as well. He had dark trousers and wore a white shirt. Over that he wore robes with a hood that was pulled over his face, keeping it indistinct and anonymous. The robes retained a white hood and included leather padding and metal bracers. They also featured blue lining along the torso and a brown shoulder belt, which held two pistol holsters at the front. He had a wide red sash which was retained and was fastened by a loose hanging belt, which held two pistol holsters on the back. On his right arm he had attached a hidden blade which was properly concealed from spying eyes, he flexed his wrist feeling the device tighten; it was ready to use.

The smells of vomit, piss, and shit assaulted his nose which he wrinkled. Men barfing in corners or lying in their own faeces made him grimace. While this might seem characteristic of the era, he knew the truth of it, in his time, men and women would be doing exactly the same thing. He paused as a young lass with big natural breasts was being fucked by some drunk shit head, her tits bouncing around as he fucked her while holding a bottle of Rum and drinking out of it. He marked the area, vowing to return and fuck her himself when he was done with his task, he took in her pale ass and big tits, before continuing.

His dillydallying had caused him to lose sight of his target for a brief moment, his prey was getting away, he smiled and moved with alacrity, the person he had been following must have twigged that he was on his tail because he was seen talking to two men. James moved into the darkness and one of them followed.

James quickly climbed up a building and knelt crouched, waiting like a bird of prey surveying its dinner, the man moved into position as James quietly pulled out a rope dart, he stood and with precision threw the dart expertly. It wrapped around the man’s throat, he grabbed at it and James leapt onto the ground, his weight acted as a counter weight and lifted the man up, James tied the rope to a secure wooden frame and left the man struggling. Soon the struggle stopped and the man went limp but James was already away from that. The second man went towards James in an attempt to slow him down, James disappeared into another dark alley and he followed, cracking his knuckles.

“What the shit?” The man paused, not seeing James anywhere, instead James moved out of the darkness and rammed his sword through the man’s throat. It poked out and he wrenched it out. The man fell to the ground, spurting blood onto the sand, James cleaned the sword and moved again.

Finally, his target took a chance and disappeared into an alley, but James had anticipated this, the man was if anything predictable and James stood there blocking his way.


James smiled, rather looking like a shark.


James moved toward the man, engaged his hidden blade and thrust it into the man’s torso. James watched as the man’s eyes opened wide in surprise, frozen like that as James let him down to the floor, keeping the blade in him, holding him there as blood filled the man’s lungs and the life began to leave him.

The man sighed as he was laid down.

As the man died he heard James speak, “This death is far better than you deserve, you fucking traitor. Had any of the other captains found out, your life would’ve lasted weeks and not mere seconds. May you find peace in death.”

His life left him and James pulled the blade out, wiped the blood off and disengaged the blade, got up and patted the man down. He found the expected envelope, pulled it out, and pocketed it before disappearing into the darkness.

James took it back to his place and then back to the marked area he had in his mind, he walked into the bar and spotted the big titted whore.

“Hey,” her companion said as he walked over. James slapped him across the chops and grinned, daring him to do something, he didn’t and James grabbed the whore and tore open her top, her big tits spilled free and he pinched her nipples. He nodded and dragged her outside, he paused at the bar, pulled out a coin and flipped it at the barkeep while grabbing a bottle of rum. He dragged her out back and thrust her over to the wall, he got his cock out, sought out her pussy and penetrated her. She grunted loudly as he started thrusting, while he did so he bit the cork and pulled it out and spat it on the ground, took a swig and got to work.

The next morning, James stood at the harbour watching the stretch of the purest blue ocean he had ever seen. He smiled at the captured ships that littered the shores, English flags flying from their masts. He smiled at the palms, the shanty houses, the huge Fort Nassau towering above it all. He actually chuckled at the fort’s Jolly Roger flag flapping in the easterly breeze as a warning to other’s who dare to try and take their freedom, it had been earned and wouldn’t be given up so easily.

He turned and headed to the local tavern where he knew Eleanor to be.

James made his way inside and to her ‘office,’ the back room with an ornate table where negotiations were discussed. Her black manservant, Mr. Scott, opened the door then looked him up and down before allowing him inside. Not that Scott could’ve stopped him if James had wanted in, and both men knew that.

Mr. Scott was an assistant of sorts, although Mr. Scott acted more like Eleanor’s servant, obeying her every request in an obsequious manner.

She stood in the room looking at him, her breasts providing overripe grandeur in the wash-faded shirt she wore. He walked past her and slumped into the seat next to her desk.

“James,” she said. “I take it that the mission was a success?”

James pulled out the envelope with the details on it and chucked it on her desk and slumped lazily onto a chair and grinned, “Easy as pie.”

She inclined her head, intimating her follow-up, “Is he?”

“Taken care of,” he waved his hand dismissively.

“Good,” she nodded grimly. “He was causing me loss of income.”

James smiled.

At least she had her priorities right.

‘A woman after my heart,’ he thought. Aloud he said: “I’ve held up my end of the bargain.”

He looked at her and she nodded, “Fine. Let’s go.”

James got up and followed her. They went to her house and once there, up to her bedroom. She closed the door behind him and studied him.

He helped her out of her clothing, untying her dress and then her corset. She had firm, pert breasts that seemed to defy gravity and pointed heavenly with delicious puffy nipples that made him groan at the sight of them.

He pulled off his shirt revealing his broad, muscular chest, which Eleanor slid her hand up, squeezing his pectorals as she shifted her body against his, her nipples pressing against his chest. James ghosted his hands down her sides to her hips before moving them back to his own waist to push off his trousers.

They kissed gently. Eleanor moaned into their kiss as he stroked her nether lips, a finger slipping amongst them to tease her pussy, almost- but not quite entering her channel. He could tell the walk to her house had been foreplay enough. Her sex was swollen and moist.

Eleanor ended their kiss and shifted away, removing her pussy from his hand as her own hand came down to grasp his cock. She moved back toward the bed, maintaining her hold on his manhood, pulling him with her. She let go of him once she came against the mattress and moved onto the bed.

James got onto the bed to join her. She grinned while reaching up to wrap her hand around the base of his shaft, while her other hand began to fondle his balls. James paused a moment as he enjoyed the feeling of her playing with him. His knees were resting outside her legs so they had to shift around to get him between her thighs. They kissed again as he slid into her, her fingernails biting into his shoulder blades as one of his hands cupped the side of her face, the other one grasping the back of one of her thighs just above her ass as she curled that leg around him.

“Fuck, you’re tight,” James gasped as he pressed his pelvis down into hers, his entire length buried inside the soft, pulsing walls of her sex.

Eleanor only responded with a low grunt and a look of concentration, rocking her hips against him, shifting his cock around inside her. James moaned, then slowly started thrusting in and out of her pussy, gradually picking up speed and force.

She pressed her head back against the pillow as she closed her eyes, pushing her hips up to meet him thrust for thrust. One of her hands slipped between their bodies, moving down to lightly tease her clit.

James kissed her as he slid his hand up from her leg and along her side to palm a delightful firm breast. Eleanor pressed her chest into his hand as his thumb circled a long, hard nipple, she brought both her hands up to pull his face from hers, arching her back as she tried to push him down to her unattended breast.

After a moment he complied, bringing his mouth down past her right nipple to lick the lower curve of her breast, dragging his lips up against her soft mound of flesh to its waiting, turgid peak.

Eleanor gasped as his mouth suckled her breast while his hand fondled its twin. The awkward twisting of his back to bring his head down to her breast robbed his thrusting hips of some of their smooth precision, but by now they were both close enough to the end that it didn’t matter. Eleanor brought her hand back to her clit, her fingers abandoning their previous coyness to firmly rub her sensitive nub, her fingertips occasionally brushing against his cock as it drove in and out of her pussy.

Eleanor came first, jaw clenched tight in a strangled cry to avoid screaming out. She had actually been that noisy once, and the sound brought her maid, Savannah, knocking on the door. She was still relieved that she had managed to warn her off before the girl actually came in.

James followed her a few seconds later, burying his cock inside her one last time as the violent orgasmic convulsions of her vagina pulled him over the edge with her.

They lay entwined for several moments before James rolled away to her right with a satisfied groan. He stretched, then sat up and swung his legs over the side of the bed. He rested on the side, his hand moving up and down her body, stroking her breasts, she smiled at him and he her as they rested in the post-orgasmic bliss.

Eventually, though, James got out of bed. He kissed her and she purred into his mouth as he pulled off the bed, he dressed and tied the red sash into place. Next was his holster for his pistols and his various weapons. He put on his hidden blade, flexed his wrist to make sure it worked properly and finally grabbed his coat and pulled it on.

He walked over and leaned down, pressing his face against her dark, triangular bush and breathed in her scent, he kissed it, moving up her body, to her breasts and her mouth, his tongue sinking in as he stroked her bush, he reluctantly pulled off and pecked her nose.

“Don’t be a stranger,” she said fluttering her eyes at him.

James nodded, kissed her again, and left.

He walked out into the afternoon street. The markets were picking up and business was booming. He needed something to eat so he went to a favorite brothel. His preferred place wasn’t quite so teeming with pirates and men today as usual, so he headed inside.

A dark-skinned beauty walked over to him and moved into his arms, she studied him, looking him up and down before guiding him over to the bar.

“How was Eleanor?”

James blinked and looked at her and laughed loudly, “How is it that you always know?”

“You have the swagger of a man who has just had cunt,” she said in her clipped tone that drove him wild. She sat on a stool and spread her legs, his eyes riveted on her dark cunt.

“I do?”

“It’s in your look, the intensity of your stare, the twinkle in your eye and certainly the swagger of your walk,” she smirked. “I’m a whore James. I see it a million times a day.”

He sighed.

“Fair enough.”

“Flint wants to talk to you,” she slipped off the chair and started unbuckling his trousers.


“Something about a job,” she reached in and grabbed his shaft, still slick from pummelling Eleanor. She grinned and fished it out. Many of the whores looked, even those with customers. His lunch was brought out, a different whore served it up for him and placed a bottle of rum in front of him, James thanked her, stuffed some notes in between the server’s tits and then bit the cork and pulled it out, he spat the cork out and before he could drink a swig, he paused, enjoying the feeling of her mouth on his member. And shortly he was blurting, “God!” as he came, mostly in her mouth, but she wasn’t too particular and his load was visible in a couple of spots of her visage.

The whore lifted up and wiped her face.

“Eleanor tastes good today,” she smirked.

“I’d better, Max.” The two started and turned around to see Eleanor standing in the doorway. James grinned at her, not bothering to hide his wilted cock. She walked over and looked at the dark skinned beauty, her eyes moving over the woman’s breasts, taking in her body, practically fucking Max with a look.

James and Max exchanged looks, well this certainly made things interesting.

“So, what was the job?” James asked.

“Captain Flint is going after a Spanish Galleon, he believes it has a large sum of gold in its cargo and has a map to an even larger sum of gold.”

“So why does he need James?”

“He reads Latin.”

James grinned.

“Take Anne with you.”

He looked at Eleanor, “Are you sure?”

“Yes,” the blond nodded. “She’s getting twitchy. Like you, she needs to see battle or she’ll get weird.”

James inclined his head.

“I’ll go see her.”

“Send her my love.”

With that Eleanor primly walked out.

“Well, I guess that’s settled then.”

Max nodded her head and ate some of his food before meandering off.

James finished up and went out to find Anne. He located her readily. As he expected, she was skulking around and saw him coming. She grinned a welcome as he walked over to her and she moved into his arms. He lifted her off the ground. James had found Anne working on a pirate ship dressed as a man, she was a tough broad but once he got past her barriers and into her heart (and knickers), she was all his.

“So I hear Flint wants to talk to me, eh?”

“Aye,” she nodded as he put her down.

“Let’s go then.”

“You don’t have to run it by the wife?” Anne said sarcastically, meaning Eleanor.

James slapped her ass and she gave him a cheeky grin, “No. Besides Eleanor is already aware and agrees to it.”

“See? You are just a henpecked bull elephant with a dick attached.” James stared at her and laughed and she grinned cheekily, “Aye, let’s go.”

The ship was easily located at the docks. James and Anne walked up to it openly. She had long since dropped the man guise at James’ urging and was just herself, not that anyone dared have an issue with it. Once she pulled her sword, she was a match for anyone in a fight.

They got to the dock and the bosun walked down to greet them. Billy Bones was a young lad, certainly younger than James. He was tall, muscular and bald. He studied James and James returned the stare.

“The Captain wants to talk to you.”

“So I heard.” James nodded, “It is why I’m here, after all.”

“Fair enough. Follow me.”

They were taken in to see the Captain. The man looked up from his charts and grinned. He was taller than James and muscular as well, with short ginger hair. He shook James and Anne’s hands, treating Anne like a man and offered them seats.

The two sat down.

“We’re attacking a Spanish Galleon,” Flint said cutting straight to the point without preamble. “I have two reasons for doing this. The first is obvious: gold and lots of it. The men have been complaining lately that we haven’t had any decent raids in a while.”

“Okay. The second reason. I’m guessing, is me?”

“Yes, I’ve heard of your unique talents,” Flint grinned. “You read Latin and are good at deciphering clues that may come in handy if this ship is carrying what I suspect.”

“A map to more gold?”

“Aye,” Flint nodded and sat back. “A rumoured treasure map, but we’ll wait and see.”

“Nice.” James scratched his face. “Okay I’m in, but I have a stipulation.”

“Name it.” James looked at Anne questioningly and Flint laughed, “Sure, if Anne wants to come.”

“Aye,” she smiled.

They left that night. James stood on the quarterdeck with Flint and Anne as the Captain barked out orders at the crew. The majestic ship creaked and groaned as it moved forward out of the docks with the man at the helm guiding her safely to open sea. The sails rippled, fat with wind.

Flint turned to James.


“Famished,” James answered with a smile. He looked at Anne, who rolled her eyes and chuckled. The three retired below. Food was prepared and brought to the Captain’s Cabin, where they dined with the officers. They ate, chatted, drank and sang before Anne begged off and dragged James back to their cabin with the officers hooting after him. He laughed it off.

Once in the small cabin, the two stripped off their sailing togs.

“God, you are beautiful,” James whispered at Anne. She flushed, obviously not used to compliments about her looks, particularly because she had been hiding as a man for the better part of a year.

“Thank you.”

He got onto the bed and she on top of him, she took hold of his cock and grinning, started to suck him off. She took her sweet time doing it and helped build him up. He moaned when she stopped but she moved her cunt over his face and started sucking again.

He came into her mouth and she swallowed most of it, she went to move but he grabbed her ass and held her in place as he sank his tongue deep into her pussy.

“Oh God,” she shivered as she came. She moved back over him then looked down at James and kissed him as she lowered her pelvis to his. One of his hands found the small of her back while the other gripped his cock, guiding it between her folds to plant himself at the entrance to her channel. From long practice he thrust up at the same moment she pushed down, joining their bodies in sex.

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