Disclaimer: Jack and other wonders belong to the mouse. Not mine, no profit, no harm intended, savvy?

Note on connection to the movies: This entire story series was started after the 1st film (obviously), but before the 2nd film. You should basically assume that it goes alternate-universe after film 1. Nothing from the 2nd film has any bearing on anything that happens here. Or, you can think of it like any legend- there are multiple versions of the same tale. This is just a different version of the Jack Sparrow legend. :D

Note on "Where's Jack?": We're starting outside of the Pearl to make it more fun when we do get to meet one of the best characters ever, Captain Jack Sparrow. Stick with it through the perspective of the dorky, uptight outsider's eyes and you'll get the pay-off of admiring Jack afresh when he appears at the end of this chapter. ;)

Chapter 1: The Black Pearl

Gwen stretched languorously as she awakened and groaned as her stomach reminded her that even after all this time, it still wasn't sure it liked being on the open sea. It was getting better, at least. She hadn't actually lost her lunch, so to speak, in several days, and she had even developed a fair semblance of the rolling gait that keeps seamen from stumbling about their ships. Yet she still felt a bit queasy from time to time. Thankfully, her trip was nearly over. Just the night before, Captain Johnson had promised her that they had only four or five more days at sea, if the weather held.

Gwen permitted herself a huge yawn, stretching once more before she forced herself out of bed. Almost instantly, her two maids appeared out of thin air (or so it always seemed to her) to attend to her. As they helped her out of her nightdress and into a corset and sage-green silken gown, she silently wished to be rid of the meddlesome pair of maids. They were too... solicitous, too... something. Too present when she wanted them to be absent. She almost wondered if her aunt had purposely given the pair of them instructions to watch over her, much like spies, to see that she didn't do anything rash on the crossing. It certainly wouldn't surprise her. Her aunt was a strange, almost eccentric, middle-aged widow with ample means in the world from the bequeaths of her late husband. Though she hadn't been quite willing to take Gwen in herself when her brother (Gwen's father) died, she had spared no expense or trouble to ship the young lady of nineteen off to her only other relatives, her father's and aunt's brother and his wife in Port Royal.

Exiting her cabin, she slowly made her way up to the main deck and then forward to the bow of the ship. She clung to the wooden rail, as though she thought she might anchor her stomach this way, and gazed out across the water. She stared off toward the horizon, watching the early light from the just-risen sun dancing on the water. Not for the first time since her journey started out, she began to think about her current situation.

She had been raised by a governess hired by her father. Gwen remembered her mother as a very kind lady who had doted on her to no end. She had had a very rough time of bringing her daughter into the world, both in carrying and delivering the babe (which came early), which perhaps excused her near-eccentric devotion and love for the small child. Anything young Gwen could have possibly wanted was given to her before it had even occurred to her to ask her dedicated mother. Her father, however, who sorely desired a son as his proper heir, had never really approved of his wife's spoiling of the child.

Then, when she was barely seven years old, her mother had at long last conceived again. This time, though, she wasn't quite so lucky as she had been before to pull through with both herself and her daughter. She went into labor close to three and a half months early, an ordeal that neither she nor her son survived. Gwen's disappointed father had seemed to blame his daughter, if not directly for the loss of his wife and stillborn son, for being born first when his young bride had only been capable of bearing him one child, which should have been the son, in his estimation. She had never felt unloved, exactly. In fact, she never considered the concept of her father as being either a loving or hating creature, simply as a provider of material needs. That was all she ever expected from him, and it never occurred to her to hope for anything more.

When her father had died, not so very long ago, her aunt had taken her under her wing, outfitting and equipping her to the life of a young Caribbean lady, and bought her passage to Port Royal where she would be met by her at least respectably wealthy aunt and uncle and three cousins, all of whom she'd never met. Her English aunt had assured her that she corresponded with the Caribbean couple several times a year and that she knew they would certainly be most pleased to take her in. So a letter had been sent along, and despite the impropriety of a young lady traveling virtually alone, a few months later, Gwen was on her way on board the Graymere. She had with her a wardrobe of gowns suitable for her new climate and a pair of meddlesome maids whom she fervently hoped could be absorbed into a part of her uncle's household where she wouldn't have to come in contact with them too often.

She was just wondering, for the hundredth time, what her Port Royal relations were like (she had been led to believe they were very friendly and kind) and whether she would get along well with her cousins, two boys and girl all younger than she, when she heard a shout from a sailor somewhere behind her and at the same time noticed a toy boat floating along on the water before her.

Or so it appeared at that distance. Far off on the horizon, a dark smudge had appeared, and without taking note of it at all, as she had been thinking, she'd been staring at it while it resolved into the form of a ship. Clearing her wandering mind with a small shake of her head, she squinted her eyes and stared at the approaching vessel. Odd, she thought. The entire ship, even its sails, was a deep black with so little shine to it that it seemed to suck light out of the air around it. At this distance, the little figures she knew had to be its crew resembled spiders scuttling across the deck and through the web-like system of the sails' rigging. She was startled as she realized how quickly the ship was drawing nearer. She almost thought it was purposefully heading straight for the Graymere. Of course, that couldn't-

Her mind clamped down on those thoughts as the ship, which had been on a course that would bring it at the closest within a league of the Graymere's starboard side, changed its course. Gwen watched in detached confusion as the ship reoriented itself so that it was heading directly for the Graymere. Are you mad? she thought vehemently at the spiders.

Of course they were mad.

She turned to tell someone, to make sure the crew realized the black ship was out there and approaching recklessly at high speeds and insanely heading directly for them. As she turned around, though, she again realized that she had been so lost in her own ruminations that she had missed something. She'd failed to notice all the frenzied activity already going on behind her. Sailors were scurrying to and fro across the deck and up the masts in much the same manner as the spiders on the shadowy craft headed for them, though from her vantage point, these looked nothing like graceful, cunning spiders, but like nervous men scrambling about erratically.

"Miss Webster!" She skimmed her gaze over the deck, trying to pinpoint the source of the call. The first mate, whose name she still couldn't remember, was running towards her.

"Miss Webster." He paused, catching his breath and bearings for a moment. "It's the Black Pearl. Get below deck, get to your cabin, somewhere safe. Don't open the door for anyone, Miss."

"What's the Black Pearl-what's wrong about it?" Gwen asked, turning to look back over her shoulder at the ship that was rapidly closing the distance. She was unfamiliar with the particular legends of this part of the world.

"Pirates, miss," he said shortly. "Go lock yourself away, now."

"Pirates?" she repeated in disbelief, turning fully to face the ship, which was now disturbingly near. However, even as she watched, she saw the unquestionable Jolly Roger rising among the black sails like a raven from the dark, the eerie grin of the skull on its crossbones familiar and almost exciting to her in tales and legends, but foreign and frightening first-hand. In the same instant that the Pearl showed its true colors, it had begun to swerve about, presenting its starboard side to the line of approach of its prey.

"Get below!" the first mate yelled at Gwen, springing away like a startled rabbit to yell orders at the crew nearest him while the captain frenetically called out his own instructions to the crew.

Gwen did as she was told, having seen all the proof of the imminent attack she ever cared to see, and began hurrying across the deck towards her cabin. Her flight was impeded as the Graymere veered hard to port to avoid crashing headlong into the pirate ship. As Gwen caught herself and struggled to maintain her footing on the wildly tossing deck, she realized with horror exactly what the Pearl had been trying to do with its outlandish and maniacal maneuvers. The Graymere was now lining up perfectly alongside the Black Pearl, starboard to starboard, and even as Gwen scrambled toward the relative safety of her cabin below the main deck, she caught glimpses of the greasy hands and faces of the crew on the enemy vessel and of grappled ropes being flung out to lash the two ships together, while the pirates yelled and jeered.

Somehow, Gwen made it below and reached the door to her cabin and gratefully latched onto the door-handle, eager to hide herself from the dirty horde that was surely boarding the ship already. Relief melted again into horror, settling in the pit of her already-uneasy stomach like liquid mercury when the door steadfastly refused to open. Frantically, she pounded the door, perfectly aware of exactly how lady-like she wasn't being. Hang those meddlesome, foolish maids! she thought fiercely. The small room the two pesky girls shared adjoined her own but this was the only door in the suite that opened into the narrow corridor. They had apparently gotten drift of the danger the ship was in and had locked themselves in- and her out!

Desperately searching her mind for another safe-hold, Gwen turned and rushed down the corridor, grabbing up handfuls of her skirts so as not to trip. She could go down into the cargo hold, perhaps... No. Think like a pirate, she coached herself. Surely a pirate would go straight to the hold, wouldn't he? She tried to run over what little she knew about what the ship was carrying, wondering whether a pirate would have any knowledge of the same and whether that might influence his decisions. Realizing that her limited time was stealing by her, Gwen shook her head. No, pirates most certainly wouldn't go to as much trouble thinking about things as she was, would they? They would rapidly seize control, take whatever they wanted, and then...well, hopefully, they would then leave. So where would be the best place for her to go to escape their rapacity?

Up. Unable to justify her conclusion beyond a somewhat-less-than-logical impression that she felt the thieves would concentrate their efforts to getting down within the ship to find things to steal, Gwen started making her way upward, anxious to escape the corridor which she was sure would soon be swarming with covetous men, looting and taking anything in sight. Praying for whatever divine intervention or shreds of luck that she could possibly hope to be granted her, she headed up a claustrophobic set of steep steps near the stern of the ship. As she reached the top of the short ladder-like flight of stairs, she took stock of her options with what glances she dared to cop of the open deck before emerging. The clash of blades rang in her ears and when she peered over the lip of the stairway's square hole in the deck, several pairs of boots danced by an uncomfortable distance from where she was concealed.

She was about to abort her hasty plans and make new ones when she heard rowdy voices and heavy footsteps farther up the corridor she'd only just fled from. She was about to be trapped here with pirates above and below if she didn't do something rash.

Steeling herself for the worst, Gwen drew a deep, shaky breath and counted backwards from five. As she reached zero, she flung herself up onto the deck, stealing for the mizzenmast with a speed and unlikely grace that was derived from the same rush of adrenaline that flows through the veins of a gazelle who has discovered the tall grass all around it to be full of lions. Her flight took her unnervingly close to dueling pirates and sailors, though she scarcely noticed in her wild haste.

Hardly pausing to take note of her extreme luck thus far, she found herself faced with another problem as she amazingly reached her immediate goal of the mast unharmed. She almost wished she were given to using oaths just so that she might curse herself. She hadn't been entirely sure exactly what she was planning to do. She had simply been fleeing, a rather primitive response, with admittedly primitive thought processes accompanying the action.

Gwen had had a rather indefinite idea (though it was accompanied by a very clear and convincing mental image of herself, safe) that she could find herself free from danger perched atop the mizzenmast, high above the chaos on the deck below. Now, faced with the ladder-like protrusions in the mast and the inhibiting skirts of her own gown, she was at a loss. The crew could scurry easily up and down this very spar, but as she experimentally attempted to get her feet onto the first rungs, she felt that her now-cumbersome dress would brook no argument about this with her.

Later she would not be able to recall exactly how she had managed it, although she could certainly point out why she'd been able to scale the mast. Her racing heart didn't take much to spur the rest of her body into action by this point. So when a tubby-looking, grizzled man bedecked in mismatched articles of worn clothing, at odds with gold rings in his ears and a few gleaming chains about his neck, lurched towards her, it was enough. Somehow she didn't think that her being a woman was a reasonable protest to make to the glinting cutlass he brandished in one hand. The concept of a decision far beyond her at this point, Gwen took the only option her adrenaline-crazed mind could fathom and began scrabbling up the mast. Between the unwieldy nature of her apparel and the man's fatty bulk, the contest would surely have been ludicrous in any other context. As it was, however, between a terrified young woman fleeing from her pursuer, it wasn't funny at all.

Some huge expanse of time later (or perhaps it had really only been a minute or two), Gwen was safe at the highest point she could reach on the mast, her relentless pursuer having turned out to be more haphazard and less vicious than her fear-clouded mind had assumed. Apparently not having noticed any jewelry on the lass, the pirate had abandoned her for more profitable (and less troublesome) capers elsewhere on the ship. As far as she could tell, even if someone else had seen her, no one had paid her enough heed to care that she was hiding above them, only partially obscured by the billowing white sails. So, from her new vantage-point, Gwen watched the rest of the proceedings with relative ease of mind.

She could see that the crew of the Graymere were gathered around the mainmast, along with about half of the ship's passengers. The group was being patrolled by half a dozen pirates or so while their comrades foraged through the ship, seeking out treasures and wealth. Gwen noticed a few of the crew bleeding from various wounds received while trying to fight off the raiders, but she was surprised to find that the pirates were now using only threat of violence to keep their victims at bay. They weren't merely leering and slaying as she had always heard and believed pirates were "supposed to" do. Rather, they were laughing raucously and apparently enjoying good-natured banter and joking amongst themselves at the expense of their law-abiding counterparts of the Graymere's crew. Apparently, this was merely sport to them, not a killing ground.

Somewhat nonplussed, Gwen allowed her gaze to wander over the entirety of what she was able to see through the sails. Pirates were merrily returning to their own ship bearing heavy rucksacks of items stolen from passengers and crew, and their cabins and quarters, as well as food and supplies from the main hold below. The disgruntled crew looked none too happy about this, but none were willing to test the reflexes of the swaggering men whose duty was to guard them. Gwen's fellow passengers all seemed more shocked and fearful than the crew, which merely appeared resigned to their fate.

Gwen spotted the first mate among the number, but not Captain Johnson. Flicking her eyes from one side of the ship to the other, she finally caught sight of him, his hands and arms securely tied behind him to the rail along the port side of the ship, his own coat tied in a very undignified manner about his head, much like a scarf, by the sleeves. He was evidently being taunted and teased by a bizarre man she could only assume was the captain of the Black Pearl. This man was bristling with a sheathed cutlass at one hip, a sword in its scabbard at his other hip, and two guns tucked into a sash tied about his waist. She was certain he probably hid still more weapons within his coat and perhaps some were even tucked into his unpolished boots. She couldn't make out much of his face from her point of view, but could see well his great mane of dark hair, matted into dreadlocks in some spots, braided in others, and adorned with beads and trinkets sporadically throughout. This mass was topped by a well-traveled three-cornered hat that very well might have been buried and unearthed again at some point for all the dirt and grime it boasted.

So lost in her consideration of the pirate-captain she had been, she hadn't realized that the rest of the pirates were evacuating back into their own ship. She watched as a couple of pirates, apparently the last of the looters, stepped from the polished wooden rail to the black rail and down onto their own ship with bags and crates of stolen goods. Turning back once again to the maned man, she saw him signal to the last of his men, those guarding the Graymere's crew, and then leap back aboard his own vessel. The lines binding the ships together were released by a few pirates as others stood at the ready to fight off any gallant fools who tried to board their ship and reclaim the treasures now that they were unguarded.

Feeling it safe to return to the deck now, Gwen cast about for some way to get down. There was the obvious course of going down the same way she came up, but her gaze alighted upon a nearby rope which somehow seemed easier to her. As she had an unfortunate habit of doing, she grasped the line before she put too much sensible thought into it and prepared herself for the swooping trip she was about to make. As was wont to happen, however, something slipped, whether her hold on the mast or the rope itself, she wasn't quite sure. She found herself flying through the air holding desperately to her rope much earlier than she had been prepared for. The world spun about her, sea and sky and deck and sails. Gwen was aware of nothing but swinging past the deck and out over the sea again for several long breath-stealing seconds. Then, her grip on the rope failing, the line none-too-gracefully flung her into an undignified heap on the deck of the ship with a great thud and whuff as the wind was knocked from her lungs.

In the few moments that dragged by immediately after she regained her breath, she experienced great relief as she saw the ships were moving further apart by the second, then confusion when the faces surrounding her were mostly unwashed and unshaven, then appalled shock as she realized that the other ship was moving away under the power of pure, brilliant white sails, while the deck she lay on was the unmistakable midnight-black of the Black Pearl.