Young Jim Caldwell gripped the brass rungs of the captain’s bed headboard overhead, his head and tail lifted, his mouth set in a silent scream and his eyes trained on the diamond-glass windows in the bay window at the stern of the HMS Royal Sovereign, now off the island of Madeira. The Royal Sovereign would rendezvous with HMS Chatham later in the morning, as the latter sailed off for duty in the Caribbean. The captain of the Royal Sovereign, Sir Edmund Dolman was mounted on the fourteen-year-old cabin boy Jim’s hips, his hands gripping the boy’s waist, his cock stroking the boy’s channel hard and deep.
Jim’s replacement as cabin boy to the captain, Sandy, a reddish-blond-haired boy half a year younger than Jim, but also fourteen, lay there beside them in the captain’s bed, on his back, legs spread and bent, cum dribbling out of his hole, and head turned toward the captain and the departing cabin boy. His eyes were tear stained and there was a dazed look in him eyes. Before moving over to Jim, Sir Edmund had dispensed with Sandy’s virginity.
It was a good night for Captain Sir Edmund--two boys holed, and one a virgin, in a single bedding.
Sandy was a sweet, vulnerable-looking boy, which likely was what found him here with the captain’s cock inside him. The same could be said for Jim, a comely dark-haired boy, with a naturally sultry look about him and arresting sky-blue eyes that attracted a man’s attention, and a lithe, perfectly formed small body that put the cock of a man who was attracted to fourteen-year-old boys at hard erection.
One thrust, then two, three, and four, and Sir Edmund flooded Jim’s passage with his cum. With a sigh, Jim moved his hand under his raised hips and stroked off his own need, as Sir Edmund rolled over between the two boys and began to snore.
Jim slept too then, after taking care of his own need, and didn’t waken until prompted to do that by Sandy’s little cries and sobs. It was growing lighter in the captain’s cabin. Jim looked over his head through the glass wall at the stern of the ship to see that dawn was near. It would be a dawning of a new life for him. He turned his head toward the beleaguered boy next to him in the bed. Sir Edmund was on his knees between the boy’s spread thighs. With strong hands the captain was pulling the boy’s pelvis hard into his groin, then releasing, then pulling the boy onto his cock again.
Sandy’s face was turned toward Jim, a pleading look in his expression. He held a hand out and Jim took it, but otherwise he just lay there and watched the large-bodied, but virile and strong British naval captain fuck his new cabin boy for the first time--well more than once in the first bedding. There was nothing Jim could do to comfort Sandy. It was 1790 and they were on the high seas. Fighting vessel captains in the British Navy at the close of the eighteenth century were gods on board their ships. They could do as they liked. The world of men isolated on the sea with only each other for comfort and release encouraged the practice of captains fucking their cabin boys and senior sailors fucking junior sailors. It was more common than not.
Sir Edmund had initiated Jim when the boy became his cabin boy--six months previous when the lad had turned fourteen, a bit late in life to become a cabin boy. And Sir Edmund has fucked Jim almost nightly since then. Now it was Sandy’s turn. Such was the world of the British Navy at the end of the eighteenth century. And thus, as far as Jim, Sandy, or Sir Edmund knew, was as it would be for evermore.
The captain was asleep and snoring once more, this time stretched out on top of Sandy’s chest, his cock flaccid but buried in the boy’s channel, with Sandy whimpering and sobbing quietly when Jim woke again. It was an hour later and the light of day having stolen into the cabin through the diamond-shaped glass window panels. There was a stirring at the cabin door, and the ship’s senior lieutenant came into the cabin and motioned for Jim Caldwell to slip out of bed, shrug into his “slops”--the loose, shapeless tunic that provided the foundation of his cabin boy uniform, and come onto deck.
“Almost time for you to transfer to the Chatham,” he whispered.
Almost time, Jim thought, but then he took another look at the lieutenant and caught the look the lieutenant gave him. There was time enough that look was telling him.
The lieutenant fucked Jim on top of the captain’s map table, Jim perched on the edge of the table, his legs hooked on the sailor’s hips, and the lieutenant standing on the deck, his hips insinuated between Jim’s thighs. Jim’s tunic was bunched up around his waist, his arms were flung around the lieutenant’s neck, and his face was buried in the sailor’s muscular chest. He moaned and groaned as the ship’s first officer thrust his thick cock up inside him. He was younger, more virile, more vigorous, and thicker than Sir Edmund was, and Jim would miss him the most.
The transfer ceremony was brief, without much fanfare, and without the presence of the ship’s captain who Jim had served and serviced for six months. Sir Edmund remained in his cabin, breaking in his new cabin boy.
The move from the 183-foot long, first-class, 100-gun ship-of-the line HMS Royal Sovereign to the 147-foot long, third-class, 50-gun naval ship, the HMS Chatham, was a move down in ship’s class for Jim but a move up in status. He was old enough now to move from service in the cabin to a place in the rigging. He was to be trained to be an ordinary sailor. It was a progression his father, a prominent London merchant and an erstwhile friend of Sir Edmund’s, had planned for him, although his father had thought that Jim would train to be a sailor on board the Royal Sovereign under the protection of Sir Edmund and hadn’t foreseen that Sir Edmund would take the boy to his bed for a different kind of training.
After six months under Sir Edmund, though, who had refined and expert tastes and techniques with which he explored his fetish for fourteen-year-old boys, Jim was an expert in pleasing older men. This had been briefed and became part of the negotiation procedures when the deal was struck for the boy’s transfer to the Chatham. The Chatham had recently lost its “sailors’ poke” to scurvy and had been shopping for a replacement for the sail to the Caribbean.
The deal had placed a good deal of money in Sir Edmund’s hands. Of this, the lieutenant paid out 12 shillings to Jim as his due last monthly wage as he turned the boy over to the Chatham’s boatswain, Peter Chaffin, at the gangplank linking the Royal Sovereign to the Chatham off the island of Madeira.
Peter Chaffin was a giant of a man. He knew the Caribbean well, as he had come from there, his father a British sailor and his mother an ebony, mixed-breed Cuban. Peter was swarthy of skin and menacing of looks and demeanor, having had a hard time of it as a sailor, working his way up to boatswain by his muscular strength, determination, and the ability to beat down any man in his way.
Receiving Jim Caldwell onto the Chatham as an ordinary sailor, Chaffin immediately took the boy to his bunk, in a preferred corner of the forecastle and fucked the shit out of him. Jim got his first taste of a Caribbean bull’s black cock. The boatswain’s technique was direct and forceful, his approach primeval and dependent on beating his prey into submission, filling them to splitting, and pounding away. Sir Edmund and the lieutenant had been refined and patient in comparison. Sir Edmund also had a connection to Jim’s father; Chaffin did not.
Three backhands and a cruel wishboning of his legs and penetration before he had been given a chance to adjust to a black monster cocked had completely cowed Jim. The stretch the cock had required his passage and the depth the giant reached awed Jim. Once the boy was completely subdued, the boatswain just knelt between the boy’s spread thighs, palmed the small of the boy’s back, and pulled Jims passage on and off his stretching cock as Jim panted and moaned. The stamina, virility, and total possession of Jim’s body of the giant both satiated and exhausted the boy as no other man had. When the boatswain had finished him, Jim didn’t know whether to smile or cry--so he did both, while still be a bit frightened that he had been aroused by the brutality of the sailor.
As the days went by of the Chatham’s sail across the Atlantic to the entrance into the Caribbean, Jim learned how to work in the rigging during the day and lay on his back on various bunks in the forecastle and relieved the sexual tensions of the senior sailors at night. He learned what it meant to be a ship’s “sailors’ poke.” They worked him both day and night to exhaustion and he learned why the previous sailors’ poke had been weakened to the point of being taken by scurvy, which few were succumbing to anymore since the Navy had learned the disease-fighting properties of lemons and limes.
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