Pirate on the High Seas

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Shemale & female sex.
10.3k words
4.73
30k
51

Part 1 of the 2 part series

Updated 06/07/2023
Created 02/03/2016
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The westerly winds had been blowing steadily for the last three days as the old barque stood out to round the headland, the casual eye would not notice her stained sails were in fact quite new and only the briefest glimpse of copper showed that she had been careened recently. Salt stained timbers gave the ship a tired and dilapidated air, though the crew jumped smartly to the sheets to haul the yards around, holding the ship to her course to enter the sheltered bay. Hands were ordered aloft to trim sail, bringing the way off her as the water shallowed, a hard eyed helmsman eyed the distance to the nearing shore awaiting instructions.

"Helm alee, Drop anchor," ordered the captain, 'Bell' Drover.

The instruction was shouted to a couple of hands in the eyes of the ship, who promptly cast off the anchor lashings and lifted the capstan ratchet, allowing the heavy wood and iron anchor to splash overboard, the cable played out until the anchor hit the seabed. The cable slowed as the anchor dragged, the capstan ratchet was dropped once more and the ship then hove to, answering to its anchor lodged in the seabed. This motley crew had handled her perfectly, thought the 25 year old captain, this exalted position was the result of a vote, subsequent to quick wits and a lot of luck. This last was predominant when dealing with 18th century seamen and cut throat pirates to boot. Drover, as navigator, had directed their ship away as they were about to board a 'merchant vessel' an action which saved most of the crew as the 'victim' lifted her camouflaged gun ports and ran out 30 cannon. Ordering Reno to ring the ships bell, to warn all hands of danger they had sheered off, suffering little damage. On retelling the events, Reno had said that it was the navigator that had rung the bell and initiated the nickname 'Bell', knowing of a secret held by the young captain he was happy to establish that name in the crew's mind.

Even though most had escaped, a volley of musket fire from the merchantman's tops killed their previous captain, 'Flogger' Harris, killing and wounding many others gathered on the small raised poop. The helmsman had died at his station and yet again 'Bell' responded, thrusting the dead body into the gap between the deck and the spinning spokes of the huge, heavy wheel. Such action, though pummelling the dead man until the wheel had lodged fast, prevented the ship from returning to it's previous course wherein lay only death and destruction. They were lucky to have escaped with a butcher bill of three killed and four injured in the ragged fusillade.

Captain Drover was not one to be drawn into a discussion of tactics or indeed general conversation, other than with the large, dark, ex Jamaican slave, Reno. Now it was he, as first mate, who bellowed the captain's orders. The slightly built captain had been a newly appointed navigator only weeks before, a quiet, thoughtful loner, who approached logistical problems with ease, displaying seamanship skills sufficient to keep the small barque safe as they plundered their way around the Caribbean.

After a hard run South and gaining safe anchor, the men were tired, the sun was dropping lower in the sky. The wooden hull of the 10 gun barque, 'Harrier,' rocked in the heavy swell, sounds carried from the ship as a weary crew ate their supper, some sang a shanty, winding down from the day's toil.

The captain had waited until supper had been cleared before locking the door and stripping to wash. First the long sleeved broadcloth shirt was removed, distinctive because of the two large patch pockets on the chest. These held thin square silver cases, one a mirror, the other serried ranks of fine flints. A boarder needed good working pistols in each hand before the close quarters work with cutlasses. The obviously masculine bulge in the narrow breeches was flattened as the tight waistband was drawn over it, only to spring out as the restraint was removed following the further downward progress of the breeches as they joined the stained shirt on the floor. The captain's cock swung with the act of throwing down the clothes, firm breasts also swung briefly, medium sized, they sat jauntily high on her chest, relieved of their hard silver coverings. A girl with a cock, not the obvious place to be, with a crew that would fuck anything that they could find. The rough baggy clothes had disguised her slim shapely body but it was Reno who instinctively protected her and with good reason. She had argued with the previous captain against flogging the big, dark man when he broke up a fight, not having taken part, as the captain had previously thought. It seemed he too had a secret, whilst on the plantation he formed a close friendship with the master's young daughter, the strong man could have her ride on his shoulders as he worked but more often they played chase together. One day when running, she stumbled and he picked her up, her dress rode up the slim youngster's body, revealing she had not bothered to wear knickers on such a hot day. Not that Reno would have noticed from his perspective but the master had seen the incident, and, outraged at the flaunting of her sex. had ordered Reno's cock and balls to be removed, just a small stub of his once huge cock remained, in order to piss. His secretive passing of water had the same furtive nature as Drover's privacy when naked. Once, when drunk, they had each confided their problems, she had told him that at birth her cock protruded quite distinctly from above the small split of a vagina like orifice, thought by those present to be a deformed urethra, her breasts were also puffy. She was deemed to be a girl and given the name Belle, it was for that reason Reno had contrived that the crew called her by her true name.

She washed, standing naked in the small cabin as the hard soapy water sluiced over soft bouncing curves, cascading down long shapely legs to wet the deck. In the hot evening it didn't take long for the water to evaporate from her body, her nipples hardened as they cooled, her cock rose slightly in response to new found freedom and the tingling in her nipples. Her hand found its way to her shaft, easing back the foreskin, revealing the bulbous head and the groove of her glans, her other hand drifted to her breast stroking a nipple, swirling around the areole hardening the whole rose pink peak. Moving on, she proceeded to stir sensation in her other breast, whilst her right hand continued rhythmically stroking back and forth. The cool air on her naked body was inflaming the feelings she was stirring in herself. Licking her hand she spread the cool saliva on the head of her cock, lubricating the sliding foreskin as she masturbated. Standing in the last dying glow of the sun shining through the stern windows, her body was bathed in an orange glow, every sculpted curve was exquisite. Her breasts jutting proudly forward, heavy globes pushing full pert nipples into the cooling air, her cock thrusting out from a taut belly and her delicious ass curved full and firm above smooth thighs. Her head went back, the sexual feeling sweeping over her was taking her to the brink, faster now she wanked, trembling knees bent, her climax approaching. A growing sensation as she ascended toward the peak of her orgasm, her whole body shaking as her trembling thighs pivoted her hips forward, thrusting out lewdly with a solid cock, until, suddenly she came. Long ropey strands of cum jetted from her cock to fall twisting onto the bare chart table, her body jerked with the spasms of ejaculation. Finally she stood panting, body covered in sweat, breasts heaving, looking through the damp hair plastered to her face, as her dick lowered, dripping.

Taking up the soap once more she started over with her ablutions until they were cut short by the rattling of the handle and a knocking at the door. Reno stood outside, calling to her,

"There's trouble with the crew, Mathews and Carey are fighting."

Normally she wouldn't bother with it but something in his voice suggested that she should. Hurriedly she threw on fresh clothes and strode barefoot to the crews quarters, it seems there was rivalry for the position of second mate and the issue was being settled with fists and knives. The first ever true democracy was aboard pirate ships, where each man was already under sentence of death so had an equal voice in every venture. Each position, even that of captain, was down to a show of hands. Fights to establish the 'credentials' of candidates were common but could lead to bloodshed amongst rival factions, she already had a seriously depleted crew. Belle pulled apart the trouble makers and asked for a vote there and then. The overwhelming majority for Mathews settled the row but she had them vote for chief gunner, knowing Carey would be voted in and was the best for the job anyway. The crew grumbled as they settled down but the altercation was quickly sorted.

Walking thoughtfully, barefoot, back to her now lighted cabin, she saw a naked Reno, his trousers around his ankles rubbing the small stub of his penis and starting to lick the messy chart table she had left covered in cum. He looked up, startled, the joy on his face fading as the implication sunk in,

"Sorry Belle, he said using her first name correctly, "I was imagining you naked, wanking and cumming and, well, I was overwhelmed."

He hung his head in shame, his dark body glistening with the sheen of sexual passion as he had licked at her ejaculation. She gazed at the tiny piss tube,

"Do you get any feeling from it at all?"

"I do get a nice feeling but obviously I can't cum." he shook his head, "I'm sorry, you should flog me for insubordination."

He turned showing the livid scars on his back but also the smooth dark cheeks of his ass, dark velvet globes above sturdy thighs, the crease of his ass appearing a darker hue. She gazed upon his body, it only served to inflame her passion, she turned back to the door and locked it.

"I've never have thanked you for looking after me so well, perhaps I should let you see, just this once, what you should be wanking over."

She removed her fresh shirt and stepped out of clean breeches, there by the door, in the gloom, the single lamp gave tantalising glimpses of parts of her body as it swung in the gimbals rocking with the ship. Here a full breast, there the curve of her ass, a brief view of her cock, Reno was rubbing his tiny appendage whilst he gazed avidly upon the vision in front of him. Her naked body moving to the rhythm of the sea, while dark animated shadows shifted on the wooden bulkhead behind her. A jigsaw after image, her softly lit body with sculpted thighs, jutting breasts and a large cock was all too much for him. Eyes still on Belle, he knelt to suck at the tasty nectar she had left on the table as he masturbated harder, to suddenly halt, breathing heavily and drooling her cum from slack lips, the peak of his sexual feelings finally reached.

"I am your unworthy servant," he mumbled, through sticky lips.

"You are no more my servant than anyone else who serves me as captain but I wanted to show my thanks for your particularly loyal service to me."

She dressed and Reno left the captains cabin, his mind full of memories that would keep him warm on dark nights, when standing watch alone on deck.

It was autumn and low, early morning mists were a feature of this marshy region, the long spit of land they had rounded shielded this small bay somewhat, from storms and of ships beating down the coast bound for Port au Prince, which lay many miles to the South east. The passage between Cuba and Hispaniola was on a direct route north east from Jamaica to the Atlantic and, via Bermuda, to Europe. Rumour had it that the merchant ship 'Carmine' was ready to leave Kingston for the long voyage to England, loaded with cotton and some valuables belonging to its ruling businessmen and even the governor, Sir Henry Moore. The pirate captain was not interested in cotton but the valuables and the sale of the ship could bring in a ready profit. It was probable that Lloyds of London insured the ship's bottom, so not all would be lost by the Jamaican businessmen. The intention was to use the mists to shroud the ship whilst lookouts in the tops could spy any shipping sailing north, possibly to Europe. It was two days before the winds were favourable for a trip north from Jamaica,

"Sail Ho!" Came the cry,

"Where away," shouted the first mate peering aloft.

"Fine on the port bow, half a league or more, steering north."

Belle relayed her orders,

"Bring the anchor up short."

The creaking sound of the capstan pervaded the deck, the clank of the ratchet a measure of the anchor cable slowly being drawn back aboard. Before long a cry from forward,

"Up and down." The ship was stood directly over its anchor.

"Secure the capstan, all hands to make sail," yelled Reno.

A rush of bare feet as the hands ran along the deck to the black tarred shrouds, racing aloft to let loose the heavy, damp sails. With the surrounding mist, there was little breeze to catch the canvas and the yards were not yet addressed to even the slightest airs The mizzen sails were hoisted but there was still no steerage way on the ship. Men scrambled down from the rigging, a mismatched lot, they were too few to handle the ship properly what with three dead and four struggling, either one handed or limping along the deck.

"Wheel amidships. Weigh anchor."

The capstan clanked as the scruffy crew laboured to pull the heavy hook out of the seabed, slowly and surely it arose dripping, to be secured by lashings.

"Steer west, nor'west. Brace the foreyards, trim the mizzen."

Orders were relayed and sluggishly the ship felt its head, turning in answer to the helm.

"Brace the mains'l."

The huge yards were turned in order that the slight wind filled the canvas, they billowed out but drew listlessly yet. In the light airs the sails were drawing but the vessel was sluggish in the thinning mist, a tortoise, beginning the race to catch her prize. The captain was thinking furiously, imagining the encounter, what would the merchantman do? Would the loss of some rigging stop her? Would she fight or run?

As Harrier gained the channel the light wind was over her port quarter, not the best point of sail for the old barque but the captain reasoned that if they pursued this heading and crossed the course of their quarry, it would firstly seem they were not following and secondly, though they would fall behind initially, they could keep her in sight and later use the wind to their advantage when they had cleared coastal waters and any ships that clung to sight of the coast.

"Serve breakfast, starboard watch first."

The hands didn't take long to chew on stewed salt pork and biscuit and even less time to drink the watered down rum which was the main sustenance in the region.

Late in the morning the order came to change course,

"Helmsman, steer north. Brace the yards," soon followed by,

"Gun crews to stations, load with chain."

Days earlier when under plain sail, she had bade them cut up canvas, using small kegs as formers they sat and stitched bags to hold enough gunpowder to fire 'chain shot.' These were two balls held together by a short length of chain, designed to take out the rigging, such missiles could stop a ship in its tracks. Even though all sailors made their own clothes on board, it did not sit easy for grown men to sit with needle and thread making bags. When loading the cannon, as now, with plenty of time in hand, the procedure was to use a damp swab, tip in a small keg of powder, ram home thick cloth wadding, one heavy ball, pile in the chain, then the other ball, more wadding and ram the whole lot home. After the first round was fired, however, the enemy would be very close, their return shots breaking through the ships planking and the sounds of shipmates screaming all around. It was far simpler to forego the swabbing and align a curved wooden trough, loaded firstly with wet wadding, then powder bag, 'chain and more wadding.' Get it lined up and ram everything in at once into the elevated muzzle. In practice, several ramrods have preceded their charges as the whole lot occasionally fired prematurely but nobody had been injured other than a few burns but it gave a second, devastating, round of gunfire.

They were now closing with the Carmine, her name readable with a long glass, though her decks were quiet, her officers had noted Harrier bearing down on them. Glasses were trained over the aft rail, Harrier's canvas was purposely badly trimmed and occasionally she was allowed to pay off to leeward, looking like she was crewed by badly trained islanders, especially with Reno and two other ex slaves on view. She kept a long gun's distance astern but always to windward of her intended victim, the afternoon wore on, lookouts had reported they were clear of any other ships, the strong sunlight was now behind them making any change in heading difficult to see by those aboard the Carmine.

Belle gave her orders,

"Helmsman, steer to place us alongside her larboard beam. Hands forward, brace all yards."

The ship quickly raced forward, taking the weather gauge and before long 'stealing the wind' from the heavy merchantman, her full sails blocking the wind from their prey, as she swept close.

"Open the ports, fire as you bear."

The five starboard gun ports were raised, the two ships were probably evenly matched, if only the bigger ship had time to run out her guns. One by one the Harrier's cannon fired, the elevated barrels sending tethered shot tearing through the other vessel. As they drew near, so the crew employed the curved troughs. Their second, unexpected volley, from scant yards away blew enemy spars and rigging apart, killing many of those lining the side about to repel boarders. The pirates swarmed aboard, their captain to the fore, into a charnel house of broken bodies and a thoroughly beaten crew.

"Bind them," ordered Belle, "Search for those hiding and bring any valuables you find."

The merchant sailors, all decked out in white duck trousers and blue shirts were not about to fight for a cargo of cotton which couldn't even be sold hereabouts. They were taunted as 'bluebottles' by the Harrier's crew, who swatted them alongside the head as they were herded into lines.

"Johnson, Carey, pick out any volunteers for our ship, then put half the Carmine's company to work, secure the rest of the prisoners in the hold. Mathews take the helm and appoint a replacement to relieve you on the alternate watch."

Meanwhile the loose rigging was cut away, the sails made good and some sort of order returned.

"Once under way, get the prisoners to dump the cargo then sail her to Tortuga and get the highest price you can."

Just then, Old Jim, a pirate for most of his life, brought a young woman from the cabin, wriggling in his grasp, she was too slim and dainty to offer much fight.

"What have we here?" enquired Belle, noting the golden curls and heaving bosom of the spirited youngster, clutching the torn neckline of her gown.

"I demand you let me go," cried the woman, I'm daughter to Mr Owen, the Governors right hand man."

"Here my beauty," said Belle, in her masculine role, "You can sit on my right hand," placing her clenched fist beside her, thumb uppermost. Her men roared with laughter, crude humour always went down well with sailors.

"Take her aboard our ship, we'll accompany you towards Tortuga, after all we don't want you being beset by pirates."

Later in the quiet of her cabin, Belle had chance to look properly at the young woman she now held captive. No more than twenty years old, she was beautiful, her creamy white shoulders were bare, such was the latest fashion, her heaving breasts were visible as she held together the torn bodice of her dress, a result of the struggle earlier.