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.
If he had any thoughts that his family would learn that Sir Edmund Dolman had sold him off and would come to his relief, he was sorely mistaken. His family in London--at least the members of the family now in control of the family’s fortunes, knew exactly what had happened and not only approved, but had instigated the betrayal. Jim wasn’t the first son in the merchant family. When his father had died, not only did that erase Sir Edmund’s obligation to protect a friend’s son, which he wasn’t doing anyway, but it also prompted the heir to the family fortune to cut out any threat to that inheritance. Jim truly was all alone in the world. His brother and sister-in-law didn’t know he had been transferred to a ship going to the Caribbean and they didn’t care. They would not have cared if Sir Edmund had dropped him overboard off the island of Madeira.
Jim almost made an appointment with the cat-o’-nine-tails the night the ship first got a sighting of the island of Hispaniola. The boy was assigned to the night watch that night. When the warning was hailed from the crow’s nest that land had been sighted an hour before dawn, and the topman midshipman, the senior sailor responsible for the rigging, Lem Bordan, came around to ensure those on watch were alert to the need to look for obstructions in the water, he found Jim Caldwell fast asleep. The boy had been worked day and night for two weeks and could not stay awake on his night watch.
This was a serious offense at sea, and punishment for offenses by sailors, especially the junior sailors, was strict and painful.
Bordan nudged Jim with his foot. Thus far the topman midshipman had nearly watched the other sailors using Jim from a distance, although the eyes of the two had met from time to time, and Bordan understood that Jim would welcome his attention. Bordan was a tall, well-built blond, with a handsome face. He stood out from the other sailors as he, like Jim a second son of a wealthy family, had better breeding than most on the ship.
“You weren’t asleep, were you sailor?” he asked, his voice low and calm.
“I’m sorry, sir ... I couldn’t...” Jim stammered.
“I said I did not find you asleep, sailor, and won’t find you asleep when I come this way again.”
“Yes, sir, thank you, sir.”
“You may thank me tomorrow, in the rigging. Just because I have not taken my privilege to fuck you in the forecastle with all the men watching does not mean I do not want to poke you.”
“I had wondered, sir,” Jim answered, denoting his willingness to lie under the man, even though the man didn’t require his acquiescence. Jim’s smile, though, denoted willingness and anticipation more than mere acquiescence, though.
The next day, Jim was climbing up into the rigging to help secure the ship’s sails, as the ship lay at anchor off the island of Tortuga. Tortuga was a haven for pirates, and the Chatham was moving to likely locations in the Caribbean to watch for pirates. None came out of harbor while the Chatham was standing off from Tortuga, but that in itself was a reason to be there--to keep the pirates from going on the prowl. Looking down, he spied the topman midshipman, Lem Bordan, climbing up into the rigging behind him.
High up in the rigging Bordan took his reward from not having turned Jim in for sleeping on his watch. He covered Jim from behind, pushing Jim’s tunic up to his waist and pulling his underdrawers down to his knees, penetrating the boy’s anus with a hard cock, and holding the boy’s wrists in his hands, while, acrobatically, he swung them together in the rigging, his cock moving inside the boy with the motion of the swing. Moaning at the words of encouragement in his ear and kiss of the man in the hollow of his throat, Jim turned his face to the man’s and they went into a tender-to-possessive kiss such as none of the other sailors taking their pleasure with Jim had done.
The topman midshipman didn’t fill and stretch Jim’s passage as the boatswain could and did, but his cocking was much more melting. His bulb kissed every square inch of the boy’s passage walls, which responded in kind by rippling over the hard shaft and grabbing it and pulling it ever deep into boy’s core, squeezing and releasing it, squeezing and releasing, until the man flooded the boy’s channel with hot cum.
The fuck completed--for both of them--and Bordan, still inside Jim and swaying the two of them languidly in the rigging still, the senior sailor whispered in Jim’s ear, “I do not like to share my boys. If you are willing I will declare you as mine and the other sailors, save the boatswain, who I cannot control, will leave you to me. What say you?”
What could Jim say, With a sigh, he pulled himself off Bordan’s cock, which he had felt was on the rise again, turned in the rigging, grabbing rungs of the roping over his head, and wrapped his legs around the senior sailor’s waist. Laughing and hanging onto the rigging with one hand, Bordan positioned his cock with the other hand, slid back up inside Jim’s channel, and fucked him again.
The topman midshipman’s move to deny the forecastle of its sailors’ poke didn’t set well with the boatswain, and he made it his business to keep a very close check on Jim. Jim hadn’t had time to recover completely from working in the rigging during the day and keeping his legs open for a succession of sailors at night. Being protected by the topman midshipman didn’t mean he wasn’t been constantly fucked by Bordan during the night.
The next time Jim was found sleeping during his night watch, it was the boatswain, Peter Chaffin, who discovered him asleep, not Lem Bordan--and the punishment meted out to him for this serious offense when it was reported to Captain Thomas Dickinson, who had no taste or time for fourteen-year-old junior sailors, was to kiss the gunner’s daughter and be greeted by twelve strokes of the cat-o’-nine tails.
The boatswain, who got off on torture, was pleased to carry out the punishment.
Much of the mental torture of being flogged with a cat-o’-nine-tail whip was that the one being punished had to make the whip himself. He had to weave a strong rope handle and then pick out at least twenty cords of the same length, sew them into the handle, and wax them. The boatswain then took the whip, selected nine of the cords, and watched as the one being punished tore out the rest. If the boatswain wasn’t pleased with the whip or the one being punished took more than the allotted three days of preparation to make the whip, he had to make it again--taking three more days of anticipation of the punishment to come while he remade the whip.
The boatswain had Jim take six days to make his cat-o’-nine-tail and he left twelve cords in the final whip.
On the day of the whipping, Jim was brought out, naked, and stretched over the barrel of a cannon, his wrists tied to his ankles. This was the “kiss the gunner’s daughter” part of the punishment. He was whipped, with all of the ship’s crew watching, salivating, and cheering the ceremony on, bound over the cannon.
Peter Chaffin did the honors, applying the whip twelve times, in four different intervals, to the tender back of the boy. The boatswain did not lay all of the power of his swing to the whipping, as he wanted the boy dominated and submissive, not dead. And then. after the flogging, because Jim was the sailors’ poke, the three senior sailors with the biggest cocks saddled up behind him and fucked him while he was bound to the cannon and while his back was opened up in bloody strips.
The topman midshipman, Lem Bordan, should have done the honors as one of the three, but he refused to and had to be restrained by other sailors as the punishment was being inflicted.
When an nearly unconscious Jim was carried back to the forecastle, Peter Chaffin attended to his wounds himself, cooing and clucking at the boy like an indulgent mother, while he applied salt to the wounds--which was done not only because they brought on more pain, but mostly because they warded off infection. After he was finished, he bent the boy over the side of his bunk on his belly, saddled up behind him, and fucked him.
Jim was left alone to heal for a week and then he was sent back into the rigging by day and laid on his back with his legs opened and fucked by a succession of sailors by night.
Lem Bordan hovered off on the fringes of the men, stewing and giving Jim looks of sympathy.
When Jim next was nudged by a man’s foot while on night watch, he was fully awake.
They were standing off Kingston harbor in Jamaica, where the ship had been docked for a week, taking on supplies, and were now preparing to set sail again to cruise the Caribbean on pirate watch.
Jim grunted with relief when he saw that it was Lem Bordan, the topman midshipman, who had nudged him.
“Sir,” he said. “I’m glad to see you. You’ve been standing off ever since ... ever since...”
“I did not want to make matters worse for you, son,” Lem murmured. “It was largely men’s jealousy that I was keeping you to myself. I see the sin of it now--and the danger for you in it.”
“I have missed you.”
“You have missed me or my cock?” Bordan asked.
“Yes,” Jim answered.
There was a moment of silence and then Bordan asked, “Do you want me to cock you now? Would you risk us being discovered?”
“Yes, whatever the risk,” Jim responded.