Author's Forward: Any characters, people or places mentioned from Disney's Pirates of the Caribbean: Curse of the Black Pearl are property of Disney Enterprises Inc. and their respective owners, and are being used in this derivative work without written, oral or otherwise granted permission.

Jacques of All Trades

Chapter One: Ladies' Night

"Jack!" Clutching a ladies' brassier in his callused blacksmith's hands, Will Turner grimaced at his companion. "You've gone absolutely daft if you think I'll be caught up in another one of your-"

"Brilliant an' foolproof plans?" The substantially tipsy and equally as notorious pirate captain, Jack Sparrow paused to look back at Will, before digging through the old weathered trunk he had kept in his cabin for such an occasion.

Rolling his eyes, Will gazed down at the lacey undergarment in hand. "I was thinking something more along the lines of... harebrained and reckless."

With a grunt of satisfaction and amusement, Captain Sparrow rose to his feet and shoved a wrinkled blue dress and matching lace parasol in the blacksmith's hands. Will stood aghast. "You can't be that desperate, can you?"

Jack smiled, somewhat wickedly. "Brilliance is born of desperation, m'good boy. Consider this... invaluable reconnaissance." He then spun to face the full-length mirror to his rear, holding up two swatches of fabric against his chest and alternating between them. "Green? Red? The green brings out me eyes, but... red's me signature colour." He muttered at his reflection. "By God, did I ever tell you what a handsome and dashin' bastard you've become?"

Will froze in place, nearly dropping the parasol in hand. "J-Jack, I... err, while I'm flattered-"

"Not you, boy!" Jack let out a hearty laugh as he tossed the green dress back in the trunk, kicking it closed with a booted foot. The pirate captain sloshed back the last contents of a small flask, grunting in disapproval as he came up with little more than a few drops.

"Why me?" asked Will, casting his head up to the powers that be, praying for an answer. But there was no clap of thunder nor bolt of lightning, only the incessant flapping of an idle pair of lips of which one too many yards of rum had passed.

"Well, Anamaria refuses to have anything to do with this. An' Mister Gibbs... I can't -nor will I ever want to- picture that man in a dress." Sparrow stumbled slightly against the wooden trunk, but recovered with a flourishing bow. "As for the rest of the crew-"

"I just don't get it." Will grunted, exasperated with his colleague. He collapsed in a well-worn chair, leaning forward to rest his elbows on his knees. "There's got to be another way. A way that doesn't call for wigs, lipstick and these bloody..." He grabbed a fistful of underskirts on the table beside him. "... lacey things!"

"Petticoats." Jack shrugged his thread-bare shirt over his head, shaking his head like a rain-soaked hound to get his knotted hair out of his face. "They're called petticoats, not that I'd expect you to know that... being a eunuch an' all." He mumbled the last words as he began the task of stuffing the cups of his bow-riddled corset with handkerchiefs.

Will leapt to his feet. "I'll have you know, my wife and I have a very healthy relationsh-"

"Will," Jack stepped behind a changing curtain across the room, his face alight with amusement. He yanked the corset up around his torso, sucking in a deep breath. "If you're worried about your fair Lizzie, I promise not to make her jealous..." Jack exhaled. "...much."

"Dear God, Elizabeth! Heaven help me if she finds out!" His face was now firmly planted in the palms of his hands. "Or worse yet, her father!"

"The ol' Gov'nor?" Jack snorted in amusement, pulling a wrinkled red dress three sizes too large over his head. "I doubt he'll be much of a problem. I have the feelin' he knows far more about wearing ladies' undergarments than he's letting on. He's got an unusually well defined waist for a man of his-"

"You still haven't answered my question." Will stood next to the curtain, wringing his hands together, agitatedly. "Why me?"

"Let's face it, love." Jack emerged, drowned in a whirlwind of scarlet fabric. He perched a limp wrist against his hip daintily and gave Will a once over. "You're what they call a pretty boy."

Hissing through clenched teeth, Will gave his friend a sharp look. "Am not!"

"Are too."

"Am not!" Will cried, his defiant stare unwavering. As the blacksmith shook his head in protest, a few errant wisps of honey brown hair fell to frame his face, accenting his stubborn, but handsomely chiseled jaw and flawless baby face. A soft sea breeze swept through the cabin, ruffling his hair and his open shirt.

The room fell onto utter silence as the two men were caught in a staring standoff.

Jack broke the silence with a cough, his tanned face trembling with suppressed amusement. He managed only a pitiful nod towards the mirror before he collapsed on the floor in rum-fueled fit of laughter.

With nothing more than a brief glance at the polished silver, Will stared back at his own reflection with great contempt. "Damnit."

After a concise introduction on maintaining a proper female falsetto and a personal consultation on the application of eyeliner, Will stood before the full-length mirror, the model of high fashion. Or so the pirate swore to him. The wrinkled blue dress only made Will's pale complexion look even more pallid, and accentuated the fact that he was as flat chested and broad shouldered as a man could get. Jack had used all the handkerchiefs the Black Pearl had in order to attain what he called 'essential feminine assets', and now resembled something comparable to a beached whale, decked out in crimson silk. Meanwhile, without any padding of any sort, Will had begun to itch in places he never knew possible and on a number of occasions attempted to vanquish the irritation with a letter opener while Jack's back was turned. A mountain of platinum blonde curls lay in an unruly pile on Will's head, threatening to topple over at the slightest move. While Jack maintained blind faith in nearly two dozen hair pins he'd stuck in the wig, Will remained as stiff and still as a board as the pirate applied a heavy coat of rouge to the boy's cheeks and lips.

"Remind me once again, Jack, why I let you talk me into these things?" Will grumbled aloud as he smoothed out the skirts of his dusty blue gown, only to have the stubborn wrinkles reappear. Unfortunate for him, no one was impervious to Jack Sparrow's warmth and charm, if and when he employed it. Not even him.

"You'll thank me one day, boy." As Jack smeared on the last of the rouge, he gave Will a firm stern pat on the back, as if to reassure his masculinity. "Not everyone has such legendary stories about the one an' only Captain Jack Sparrow."

"Donning wigs and corsets, then parading around Cuba in the dead of night is a sound foundation for a legendary story?"

"With a little... embellishment, anythin' can be if Jack Sparrow is nigh." Jack piled his own hair under a dark wig, pinning back the renegade locks. "Y'know, add a few vicious buccaneer sorts here, maybe a mystical knick-knack there an' you've got yourself one smashin' bedtime story!" He waved his hands around, orchestrating his own fantastic ideas.

Will would have buried his face in his hands again, but feared smearing his makeup would do little to dissuade the crossdressing pirate's 'foolproof' plans.

"Give over, mate!" Jack pleaded. "It'll do you some good to get your land legs back, if only for an evenin'." He rose, tucking his dark knotted hair beneath a massive hairpiece of auburn curls that could have easily been mistaken for an Irish setter.

"But, what about...?" Will leaned forward and gave a quick tug on Jack's braided beard and then indicated to his own unladylike fur. Unless the locals would believe ladies with extensive facial hair was all the rage in France, which was entirely unlikely, Jack would have to abandon his outlandish idea. Finally, a loophole in his favor!

Jack's eyes lit up with youthful innovation, as he shoved a colorful folding fan in the whelp's hands, garnishing his own outfit with one as well. "I've got that all covered, me boy."

Will slumped against the door, his nails digging into the handle of his parasol. "I was afraid of that."

The sun had long set, and Will kept a watchful eye as they exited the captain's cabin. If the crew caught sight of this, Will couldn't imagine surviving the trip back to Port Royale. He'd die of embarrassment. Sneaking along the main deck, the lights of the port town of Baracoa flickered at the end of the pier only a couple hundred yards from the ship's harbor. As they came ashore, Jack took to a lady-like gait like a fish to water, while Will stumbled a few feet behind his companion, cursing words he saved for only the most ripe of occasions.

Trekking further into the small Cuban villa, he tried his best to ignore the muffled grunts of passing merchants, several of which gave the two 'women' disturbingly drawn-out looks.

"Where are we going?" Will hissed, fluttering his fan tentatively to hide his face.

"Keep up appearances, love." The pirate squawked back in a well-crafted falsetto as he led the march. "We're off to the King's Arm!"

The narrow winding streets of Baracoa offered little shadow and shade for a young man dressed in women's clothing to sulk in. The well-lit and overall friendliness of the town, while usually would have been welcoming, presented Will with an entirely different set of concerns. Meanwhile, Jack pranced along, occasionally giving Will's arm a rough, rather unladylike tug. They were nearly half a mile into the city, and Will realized he'd gone too far to turn back now. Silently and solemnly, he deemed an empty wheelbarrow laying on its side on the road the official point of no return.

"I don't know how they do it, Jack." Will grunted, adjusting his whalebone corset as he attempted to make small talk to ease the uncomfortable silence. "How a woman, let alone man, is supposed to function properly in this iron maiden is beyond my comprehension."

Jack gave Will a hollow pat on the back, his eyes fixed on the road ahead. "You'll get used to it after the first few times, boy."

Will recoiled behind his fan and lace parasol, his brows knit together. His mind wandered and wondered all the while if Jack habitually dressed up like this for other various... reconnaissance missions.

Oh, God. The thought was as unsettling as it was intriguing. True, the man is remarkably well versed in the delicacies and fineries of women's undergarments, but-

Jack yanked Will's arm, roughly, pulling him onto a poorly lit narrow side street. Struggling to keep his balance, Will nearly dropped his fan in a shallow puddle of rainwater.

"Nearly there." The pirate whispered, nodding furtively to a doorway, lit only by a swinging lantern. A weathered old sign, written in bold serifs that had begun to peel away with age was the only indication that they had arrived at their destination.

Clearing his throat with a cough, Jack began to bat his eyes, preparing to spread on the coquettish charm as thick as possible. Only one more obstacle lay between them and the front door. Jack could almost taste the rewarding tang of freedom, while Will had to fight off the bile rising in his throat.

"Evenin', senoritas." A broad-shouldered man peered down at them from nearly a full foot up, his meaty arms folded across his barreled chest. From his thick accent and even thicker red hair, Jack surmised the guard wasn't a local, but imported muscle. His stare, a combination of suspicion and interest was just enough to churn Will's stomach inside out.

"Evening." Jack's high-pitched feminine bravado would have been side-splittingly hilarious, had they been under other (drunken) circumstances. "Would you mind moving aside so two respectable old women can pop inside for a nip? It's frightfully dark out here."

The guard cast a curious look down at them, his scarred face obscured in the shadows. "Respectable old women, eh?" His suspicious beady eyes combed over them, probingly. While Jack continued to flutter his lashes at the man, Will could hardly keep his knees from knocking. An overwhelming feeling of impending doom filled the well of his chest. A man couldn't be hung, drawn and quartered for impersonating a lady... could he?

The guard cracked a near-toothless smile. "Why, neither of ye look a day o'er... sixteen."

Exhaling a breath he hadn't known he was holding in, Jack coughed behind his fan. "How... very kind of you, you dear, dear man."

Suitably pleased with himself, the man pushed the narrow door open with a thick hand, showing off more than just an impressive set of muscles but numerous explicit tattoos as well. Will's hands trembled with anticipation, as he held back the urge to reach for his trusty blade, which he conveniently left in his other corset.

A lazy smile curled the guard's sullied mouth as he gave Will a wink. "May ye drink yer fill an' merry-make not unto ruin, fer tonight, ladies drink free."

Author's Note: As they say, idle hands are the devil's playground. And these hands had a keyboard at their disposal. (No internet/phone/cable for a month and a half can rearrange one's priorities rather quickly. In turn, I shall take this moment to curse the Deutsche Telekommunists and all their wretched subsidaries. Damn you, TKS/T-Mobile/T-Online! Damn you all to hell!) I've got well over half a dozen chapters, awaiting a final light polish before I post them, so fear not! Questions? Comments? Public verbal floggings? Review at will, maties! If inspiration fuels the mind, then surely praise fuels the pen!