Yarrr! The Legend of the Black Spot

Aye! Sit 'round, me hearties! The night is cold, and the mulled wine we took from those wussy merchant landlubbers is not yet warm. Aye, sit 'round and I tell ye the tale of the dreaded Black spot. O' course, we all seen the Spot; I gave it t' Bosun Scurvy just before I shived him fer cheatin' at blackjack, last month. But none of ye, I wager, ever heard tell of the first Spot, and who gave it. Eh?
This be a tale of Cap'n Jack, the first ever Pirate King, long before Jonah and Noah and not long aft' Adam hisself. You may know Jack from the legend of Jack-o'-lantern, but them scurvy Irish never knew of Jack's piracy, so it be not in their legend. Oi! Shut up back there! I be tellin' my story. Anyway, where were I? Ah, yes, Jack. Jack was the first, an' probably the greatest, of all the Pirate Kings. From the Mediterranean to Atlantis to the New World; Asia, th'Subcontinent, and nigh the Ends of the Earth, he pillaged and hoarded. All o' the ancient marvels of the world, now broken and forgotten in the Flood or such, were at one time in Jack's holds. His ship was like unto a beast of legend, fast and virile enough to put to shame the Flying Dutchman, the Nautilus, and mighty Vingilótë, all in one blow. Hard and, er, leathery were his crew, and with them he collected the wealth of the gods themselves.
He discovered, in that frozen hell beside the southern pole, a hidden city o' wondrous strange folk. Fer a while he stayed there, gaining their confidence. Then he took their great treasure: a fell sword, black as obsidian, fallen from the heavens, like the black blade of Lucifer hisself. It was made not of iron or any metal, but the hungry Void, and there was naught it could not cleave in twain. Then he slaughtered them all, and their secrets died with 'em. With this blade he was become like a juggernaut, and he took what he wished, from even the greatest empires.
From Persia, he took the Cup of Life (that would become the Grail). Other treasures he got too, gems and jewelry and tricksy devices, and unlike stories not told by pirates, this booty did not make him miserable at all; Jolly was life aboard Captain King Jack's worthy vessel. But always chief among Jack's treasures were his black blade and the Cup of Life. They were his left and his right hands. With them his empire stretched from sunup to sundown, and his enemies despaired of ever seein' the end of it. But despair is an evil trick, quite un-piratical; there's always hope o' movin' up in the world, isn't there boys? Arrr, yes.
When Jack reached the comfortably robust age of Three hundred and Thirty Three, Ol' Davey Jones, the Devil, grew tired of waitin' for a man as incorrigible as Jack to give up his kingdom and enter into Jones's, you catch my drift? Upon his inverted throne Old Scratch turned to his good friend Mephistopheles and asked a kindly favor of him. So up went Mephistopheles to pay a little visit to good Jack.
That night, King Jack woke up in his fancy rooms, sweating like he was bein' boarded, (which hadn't happened for two hundred and ten years!) with a sound like thunder fillin' his ears. So he sat up and noticed that there was lava pourin' out of a hole in his lovely Persian carpet, and that the woman beside him (his 4,732 lay) slept as if she were dead. "Mighty odd," thought Jack. "This be an uncanny dream." Then up from the hole stepped Mephistopheles, and his hooves made frost on the lava. He spoke, saying: "Jack, king of all pirates, emperor of the world, hero among mortals, I bring tidings from my master, the true ruler of the World. He bids ye welcome and entreats ye visit him anon." For a time Jack thought, weighing his weariness of the world, the same tired routine, and considered the possibilities of piracy in the Underworld (for what more suitable place for a pirate than Davey Jones's Locker, eh boys?)
Then he thought of all the merchants he had yet to loot and all the grog he had yet to drink, and all the scarlet pirate maidens whose acquaintance he had not yet had the pleasure of ... attaining. And he spoke unto Mephistopheles saying "Ye may thank your master for me, but tell him that I am disinclined to acquiesce to his request." Mephistopheles seethed and said, "Vain mortal! Today I shall personally oversee your torments!" and leapt forward, meaning to drag Jack, body and spirit, to Hades.
But Jack seized up his black blade from the crystal scabbard he kept by his side at all times and swung it, just as the demon clutched a hold of his arm. The fell blade clove through Mephistopheles's unholy bracer, and the hand fell from Jack's arm, leaving a foul scar; Thus Jack became the first pirate to be branded. And a great dollop of black demonblood shot from the wrist of Mephistopheles and landed in the palm of Jack's left hand. The fiend shrieked "Curse you, impudent lout! None defy the fate of Cain! Curses be upon you. I shall see you anon, puny one, and ye shall receive payment for this, and more." With that he sank back into th' Abyss, clutching his stump.
For the rest of the night Jack kept watch, gazing at the black stain upon his palm. He tried to console himself with the thought of his Chalice of Immortality, which had served to keep him from the Locker for three centuries, but doubt's cameo was etched in his hand, so t' speak.
He went to sea with his most trusted men and slept little, but in a month, on his Three hundred and thirty fourth birthday, he was betrayed foully by a cabin boy and slain in his sleep. It almost came to pass that the boy succeeded Jack as emperor, but by fortune's stroke the evil blade fell from his hands point-down and cut through the hull to sink to the depths. Perhaps now Davey Jones has taken it back unto himself, or perhaps it cut even into the heart of the Earth, and is lost 'till the breaking of the Foundations. Anyway, with that bloody great hole in their boat, Jack's men put ashore in Wales, where the Cup of Life passed into other stories. Thus the buckaneers of Jack the Pirate King passed his tale along, and whenever one had a score to settle with another, he made a Black Spot in memory of his king of old.