I was just about home free with the tasty wench the lads had brought on board for me from Kingston when the attack started. After some mouth play, she hadn't objected in the least when I'd unlaced her bodice and started giving her ripe melons the attention they deserved. We were entwined together in the window seat of my vessel's fantail, and, forward lass that she was, she had unbuttoned my codpiece herself, fished out my Johnny, and was making it thick and hard with her stroking hands. I bunched up her crinolines, was delighted to find she was wearing no undergarments, and dove to her luscious pink clit with my lips. When she was wet and wild, I stood away from her and stripped off my breeches. I was now standing completely naked before her except for my black leather boots, and she was admiring my manhood. She entreated me to come into her quickly and deeply, and I was making my final approach when all hell broke loose on the deck above me. It was clear that we were being boarded in the night, and it seemed equally clear that my men were outnumbered.
I had no time to do more than grab up my short sword and turn to the door, when the door burst open and Black Ned, my Nubian cook and valet, spun into the room. My slight but well-formed and flinty Nubian companion was being closely engaged in hand-to-hand sword combat by a swarthy pirate twice his size. Spinning in behind Black Ned's assailant was one for me too, a muscle-bound Scandinavian giant twice the size of Black Ned's opponent, stripped to the waist and covered in tattoos. A black giant of a man tried to swarm in behind him but was stopped in the doorway because the cabin was hardly big enough to hold the combatants and petrified lady already in attendance.
Black Ned ran his opponent through the gut with his sword, leaving no doubt that the man had been dispatched. At the same time, my sword tip found a soft spot near the abdomen of the Scandinavian. As both men fell, the black giant found room to enter and pierced Black Ned's side with his sword. I pulled my own sword out of the Scandinavian and sliced at the black giant's sword arm just as he was preparing to finish Black Ned. This assailant turned to me with a look of surprise and malevolence in his eyes, and I was about to run him through when the doorway was filled with yet another figure. We now were joined in company by the apparent pirate band leader, a magnificent figure of a man, dressed fancier and more ruffled than his compatriots and honored with the benefit of two flintlock pistols rather than cutlery. I heard a loud noise and saw a puff of smoke enveloping the visage of this late-arriving figure, and all went black.
When I became half conscious again, my first sensation was of a burning sensation in my scalp above my ear, where the ball had grazed my head and laid me out cold. My next memory was of the screaming from the adjacent cabin of the wench I'd nearly won. Clearly someone else was reaping what I had carefully sown. My third memory was the most painful of all. My hands were tied off with rope above my head around a leg of my captain's desk in the center of the cabin, and I was stretched out on the desk, belly to wood. I felt an excruciating pain in my intestines and soon became aware that the fancy pirate chief had his cock up my ass and was churning away inside me. He and his men had caught me in a distinct disadvantage of total nakedness other than my leather boots when they had penetrated my cabin, and the pirate chief must have taken a instant liking to what he saw, obviously preferring me to the woman other members of his crew were playing with in the adjacent cabin. Now he was penetrating me deeply, and I was not at all accustomed to being used in this way. He pulled my head back toward him with a grip on the hair I had tied off in a tail, arching my back. With his other hand, he brutally turned my head to him and possessed my mouth with his churning and searching tongue until I was near unto gagging. He continued to pump away madly at my ass. At length, he let loose of my head and moved his hands down to my pecs on either side, and dug long fingernails into the aureoles surrounding my nipples.
To try to block out the pain from my brutal taking, I looked into the corner of the cabin, where the black giant, a rough bandage around his sliced arm the only clothes he now was wearing, was force-feeding a long and hard, but not terribly thick cock into Black Ned's mouth. Black Ned was on his knees, his chest was covered in blood from his own wound, and the black giant was holding a knife under his chin to encourage Black Ned to give him good suck.
I screamed and writhed back and forth, successfully causing the pirate chief's long and thick cock to dislodge from my ass, but the struggling served me not. The pirate chief turned me onto my back on the table and rendered me unconscious again with two heavy fist blows to the face. When I regained consciousness, he was fucking me in the ass again, but this time I was below him on my back and he was wish-boning my legs out and up from my body. When he saw that I was conscious, he pushed my legs down along my body, my toes point toward my head, and brought his own torso down on top of mine and attacked my nipples and my mouth with his teeth. He was looking into my eyes and grinning a silly grin and clearly enjoying the yelp I gave with every deep thrust he made with his cock.
All I could hear from the other cabin was weak sobbing and boisterous laughter from more than one male voice. But then I heard a piercing scream cut off at its apex, and I started to struggle once more to get out of the clutches of the pirate chief and to do whatever I could, albeit belatedly, to right this wrong being done to the woman I'd been dallying with.
The pirate chief's fist went to the wound in my head and I saw fireworks, felt maddening pain, and fainted once more.
This time when I awoke, I was out on the open deck, strung up with rope around both wrists, which were tied off on the rigging of a mast overhead. Black Ned was similarly tied off, facing me, not more than twenty feet away. The pirate chief stood between us, at a right angle to us, his legs splayed out a wide stance, a satisfied smirk on his face, and his arms crossed on his chest, a flintlock in each hand. He was stripped to the waist, showing a magnificent barrel chest, and his horse-hung cock still dangled from his open codpiece. I wondered that all of that had been stuffed up me, but the searing pain in my ass canal left me little doubt that it had been.
I watched in horror and fascination as the black giant fucked the slight Nubian, Black Ned, from behind with his long, long cock. With their disparity of size, I thought that surely the cock was making its way into Ned's stomach. The black giant was bent at the knees and was swinging Black Ned's butt back onto his battering ram of a cock with beefy hands lodged unto the smaller man's thighs. Black Ned obviously wasn't enjoying this treatment nearly as much as the black giant was.
Seeing that I was awake again, the pirate chief came around behind me and entered me again with his cock, sliding in to the hilt and sending ripples of pain - and, yes, of pleasure too - around my ass walls. Two of his men held my legs out while the pirate chief plowed me yet again. The pirate chief wrapped his arms around me, buried his lips and teeth into the side of my neck, and his hands, now bereft of his flintlocks, locked onto my manhood. I was greatly embarrassed that my cock hardened up for him and that I spilt my seed on the rough planks of the vessel's deck.
While this was going on, I saw a bundle of petticoats, which I recognized as having recently draped my earlier female near conquest, carried out of my cabin and thrown over the side of the ship. The splash they made told me that more than petticoats had been in the bundle.
The black giant grew bored with his fucking of Black Ned and pulled away from him. The pirate chief suddenly tensed and bathed my insides with his cum. He then pulled out of me as well and returned to his stance between us. Waving a reacquired flintlock in Black Ned's direction, the pirate chief declared that Black Ned had killed one of his best men. 'What then,' he asked his assembled men, 'should we do with him?' The word 'death' rang around the deck.
'How about death by belaying pin?' the pirate chief asked in a ringing voice, and boisterous assents were given all around.
At a signal, one of the other pirates brought out a belaying pin that was well over a foot long and several inches thick, and, at the pirate chief's command, he started forcing the wooden phallus up Black Ned's ass and rotating it around. Black Ned screamed for several minutes as the belaying pin twirled up his ass. Blood streamed down his thighs, and then I saw his eyes roll back into his head, his body give a shudder and the life drain out of him.
The pirate chief's flintlock then turned to me, and he told the two men I had wounded and who now were naked except for the dressings on their wounds that they could have at me together if they liked in compensation for their wounds. They obviously liked, because the Scandinavian approached me from the rear, with his long, thick manhood at attention, and the black giant, with his longer but thinner cock, also at attention, approached me from the front, other ruffians lifted and spread my legs wide apart, and two assailants I had supposedly wronged both entered my ass with their ram rods and began fluttering their hands all over my body and each other. The cocks of the two pumped me in counter piston action until both pirates had cum, almost simultaneously.
I thought I had been stretched and filled to the limit, but when the two were finished with me and had pulled their dicks out of me with a sucking sound, the pirate chief asked his crew what should be done with the captain of the ship they had just taken. I once more heard the sickening word 'death' being proclaimed to the winds. The pirate chief looked around the deck, obviously searching for something, and then all eyes, including mine, went to the railing around the bridge over my cabin. Each separate section of the railing was topped off by a newel post. Each post was topped with a round, wooden ball of some four inches in diameter that was commonly used to contain tie offs of ropes from the rigging.
'Death by post ball,' the pirate chief declared in a ringing voice, and all voices but mine agreed with a great deal of mirth. I had no illusion how they planned to use one of those four-inch post balls, and I began to jabber and sob.
'Or perhaps you would prefer this,' the pirate chief announced with a laugh. He then walked back over to me and slid the cold barrel of one of his flintlocks up my ass. With a sickening sensation, I heard him pull the trigger, which was followed by a dull click. The pirate's crew roared with laughter at this excellent joke, and my knees gave way and I almost fainted again.
The black giant and the Scandinavian were untying my ropes from the rigging and starting to manhandle me up the stairs to the bridge, when there were new shouts heard at the far side of the ship, and we all turned to see yet more sailors, armed to the teeth, coming over the sides.
The harbor master must have noticed the earlier attack on my ship and sent out the Kingston marines, I reasoned, as I tore myself from my now-elsewise-occupied tormentors and backed to the far railing.
Looking down into the murky nighttime water, I saw that there where other small, open boats on this side of my vessel. Reinforcements were preparing to come up this side as well, I thought.
I climbed up on the rail and dove into the water, my presence now completely ignored by the pirate chief and crew who had raped me and killed my companions. They had themselves been caught by surprise and were now fighting for their own lives.
The water was cold, and I was weak from the recent assaults on my body, but I managed to dogpaddle to one of the open boats, where strong arms pulled me up into the boat.
There was only one sailor in the boat. He must have let off his comrades on the other side of my vessel and been sent around on this side for safety and to pick off any of the pirates who had tried to escape this way. He was even bigger and more heavily muscled than the Scandinavian pirate had been. And he was stripped to the waist; was covered in tattoos, including a prominent death's head; had a big ring through one ear; and obviously was ready for action.
Boy, was he ever ready for action! It hit me instantly that this was yet another pirate. He leered at me, and chortled a, 'And what do we have here, my lovely?' as he quickly tied off the ropes still around my wrists on hooks at either side of the bow of his open boat. He pulled my pelvis up onto a wooden seat of the boat, allowing my shoulders to hit the bottom of the boat and my head to bounce off the bow's gunwale. Through the piercing pain this head bounce caused in my head wound, I saw him standing above me, unbuttoning his codpiece, and rolling out the longest, thickest cock I'd seen that night - already hardening fast. He knelt down below my butt, and I felt a thick finger roughly entering my ass.
The sailor grunted in surprise and pleasure. I needed no preparation for him; my ass was already swimming in the cum of several who had gone before him, and I was lathered up enough to accommodate him. He grabbed my legs in strong hands and hung them over his shoulders, and I screamed in surprise and pain as he thrust himself into me, plowed his engorging dick to the depths of my ass canal, and started a relentless deep fuck that went on forever as the din of battle roared over our heads.