Disclaimer: None of this is mine, much as I wish monkey!Jack were...
Jack Sparrow was a happy man.
True, he had lost the Pearl and was currently sailing the seas alone in a dinghy. But the map in his hands more than made up for all of that. Even the freedom that was the Pearl paled in significance next to the prospect of immortal youth.
And once he had immortality, he could always take the Pearl back. It wouldn't be the first time, after all.
No, Jack Sparrow was a happy man because his greatest desire was within sight, drawing closer with every swell of the waves, and there was nothing that could possibly keep him from it. Not this time.
The sea erupted in a sudden violent whirl of water and wind before him, and Captain Jack Sparrow began to have the sinking feeling that he may have thought too soon. But as a ship emerged from the maelstrom's center and the waters began to subside around it, he allowed himself a slow smile. He had nothing to fear from the Dutchman. He had always been able to talk his way around her captain, and he knew that had not changed now.
Will Turner appeared at the rail, and Jack sketched a rather clumsy seated bow, flourishing his arm a bit more than was perhaps necessary. "Well, if it isn't young William," he greeted, reaching behind him for the flask of rum. "What brings you to these strange and deserted waters?" At this, he tossed back the last of the rum and threw the bottle overboard for good measure.
"You owed a debt to my predecessor, Captain Sparrow." Will's voice was calm, devoid of any emotion, but he was smiling. Jack didn't like to admit that it was one of the most unnerving things he had seen in a long time. And he had seen quite a bit.
"Damn," he muttered. Suddenly, his current lack of a ship seemed a much greater source of distress than it had moments ago. His dinghy didn't seem likely to outrun the several rowboats that were already moving to surround him. (And where had they come from, anyway?)
"One hundred years, Jack," Will greeted him as he was brought aboard. "It really isn't that long."
"It'll be only ten for you," Jack grumbled. "If your distressing damsel is still waiting for you, that is." He tilted his head and grinned. "Think she will be?"
"She will. And if you can see your way to following orders, Jack Sparrow, perhaps it'll be only ten for you. And then you can come back to these 'strange and deserted waters,' and find your water of life."
Jack started. Really, how could the boy know about that? Unless…
"Barbossa," he cursed in disgust.
"But the ten years come first, Jack," Will said, ignoring his outrage entirely. And then he grinned. "Well, Captain Sparrow, what do you say? Can you sail under the command of a pirate?"
Jack looked back at him for several moments, a new found respect forming in his mind. Perhaps the boy had finally grown up.
"I suppose I'll have to, mate," he said at last, with a theatrically resigned sigh.
The Captain of the Flying Dutchman turned to his crew. "Hoist the sails," he ordered, "and Mr. Turner, take the helm please." And then he turned back to Jack, laughter and revenge mingled in his eyes, a mop held in his outstretched hand.
"Mr. Sparrow, swab the decks."