What Vexes All Men

A/N: Aside from knowing the tale of Davey Jones, Jack Sparrow's answer to Tia Dalma's question: "What vexes all men?" was quite the assured one. Perhaps our beloved captain was a vexed fellow himself, leaving him prepared to answer such a question. Maybe Jack wasn't always the heartbreaker, maybe he was the heartbroken!

Chapter One

"Ladies. You have standing before you, a prime example of manhood. All you must do to attain said manhood, is speak the word."

Jack Sparrow stood, hands clasped ahead of him in an almost pleading manner, golden teeth glinting gallantly in the flickering light of the street lamps. Before him stood two ladies of an obvious profession, both with arms crossed over well-endowed bosoms. Neither seemed impressed with the young, dreadlocked pirate—despite his desperate smile. One of the ladies gave a cackling laugh.

"A prime example 'o all the poor blokes comes thou'h here expectin' us to be friendly." She said to her fellow lady. The counterpart snickered in agreement. Jack was not swayed by their nay saying and attempted again.

"My dears, I can assure you, payment can be made early tomorrow—tonight I find me pockets empty and my arms lacking that of a touch most feminine." He said pitifully, moving to take one of the women by the waist. She however, was having none of it, smacking Jack hard across the cheek, his head swinging over his shoulder the charms and beads in his hair clinking together like chaotic music. The prostitute, pleased with her work, turned on her heel, looking over her shoulder at Jack as she did so.

"If ye can pay tomorro', then we ain't givin' no feminine touch till tomorro'!" she crowed, flipping her hair back over her shoulder with a "hmph", her friend mirroring the action. Jack on the other hand, rubbed his jaw, testing to see if it was still on its hinge.

"A man's not likely to find much femininity in that particular hand," he muttered, waving after their retreating backs with his free hand, "don't worry lassies, many women are overcome with a sudden unsteadiness when in the presence of such a specimen…" he said, finally waving them off with little care. As the sting of rejection and hand crawled across him, Jack heard a familiar chuckle and turned, finding himself face to face with Joshamee Gibbs.

"Looks like ye'll be spendin' the night alone, Jack." He said, the laughter in his voice evident. Giving the older man a pained look, Jack turned away from him, beginning the short journey to an even longer night of loneliness.

"What's yer headin' Jack?" Gibbs asked, hurrying to catch up to his fellow pirate. Jack threw his hand in the air as though to brush the elder's question away.

"Mr. Gibbs, I am making berth at the nearest tavern to drown my latest sorrows in the golden graces of that most ineffable brew known as rum." He answered, knowing full well the old sailor would most likely ask more questions.

"I thought ye told those two ladies ye've no currency to be had." Gibbs pointed out, despite its obviousness. Jack stopped, turning slowly to face his friend.

"Mr. Gibbs, if everything that passed my lips was truth—how could I possibly maintain the title of the Caribbean's, most fearsome and notorious pirate?" He asked, not surprised when Gibbs gave an understanding shrug. As this point Hack turned again, back on his current course. Gibbs jumped to attention and followed.

"Mind if I join ye, Jack?" he asked as their booted feet kicked up puffs of dirt from Tortuga's filthy streets.

"I'm not buying yer drink, savvy?" Jack replied as their silhouettes shrunk into the shadows of the night.

When they reached the tavern, the nightly brawls had already begun. Gibbs, hands full with mugs of rum, swung to and fro attempting to avoid being hit with bodies being flung every which way. He was too slow and found himself drenched in the inebriating liquid. After the initial shock of the spill, Gibbs looked into the mugs; realizing one was half empty while the other remained nearly full. Without much hesitation, Gibbs dumped the contents into the nearly empty mug, withholding it as his own. As he sat down, he handed Jack his drink, the gold-toothed man eyeing the mug and its mysterious emptiness and noting the obvious fullness of his shipmate's mug.

"Mr. Gibbs—" he began, the elder pirate's mug stopping just short of his lips.

"Yes, Jack?" he answered with little zeal.

"Why is there an apparent deficiency of rum in this cup?" Mr. Gibbs swallowed and gave a weak shrug.

"The barman must've forgotten to fill it." He answered, though from the look he was getting from Jack, it wasn't exactly passing. The younger man's eyes narrowed and fell to the large wet spot on Gibbs' shirt.

"And yet, in his forgetfulness, he found it appropriate to give you a parting gift?" He asked, slightly humored by his friend's discomfort. Gibbs rewarded him with a simpering smile.

"Jack, let me explain…" He began only to find the other pirate's attention elsewhere. He followed the man's gaze to the door, seeing what Jack was looking at. At the end of the room a young woman with brilliant red hair was leaning against the worn bar. She was dressed in a calf length skirt, embroidered with flowers and a white linen shirt that slipped off her shoulders in a most pleasing manner. She was speaking intently with the barman who was gesturing to the back of the tavern where Jack and Gibbs were sitting. Gibbs looked back at Jack and saw the man's eyes glaze over. He shook his head, taking a gulp of rum and looking to his suddenly enthralled friend. He reached across the table and set a hand on the man's shoulder.

"Careful Jack, she looks to be Irish, and the Irish can be fiery tempered—so I've heard." He said, not entirely sure if the man had heard him. From the look on his face, Gibbs was fairly certain the he hadn't. He patted Jack's shoulder and sat back in his chair once more. As long as the rum held out, he would wait until his shipmate snapped out of his sudden enamourment.

On the other end of the tavern, the red-headed newcomer turned from the bar, her face set in a frustrated line until her light green eyes met Jack's dark brown ones. Her frustration seemed to dissipate slightly. The barman caught her attention as he added more to their previous conversation; he also slid a piece of paper across the scarred wood to her waiting hands. She read it quickly, shoving it into the bodice of her shirt and stalking to a table off in a dark corner. As she slumped back in her chair, Jack suddenly shook his head and looked at Gibbs.

"Mr. Gibbs, as much as I have enjoyed are little chat this evening—I find myself inextricably pulled to this damsel's most distressed side. I bid you a—" he looked at the older man looking for the right word for someone who was in most likeliness going home alone. "Well, whatever it is you'll be doing." Gibbs lifted his mug in toast to Jack's words and took a swig with little offense. Jack took this as his cue and picked his way across the tavern—side-stepping several piles of passed out bodies on his journey.

As his shadow fell across the table, the woman he had seen from across the way looked up from her hands, her eyes traveling up a torso well furnished in belts and the effects of a pirate, to a chin bearded with tiny braids and beads, a smile checkered in gold and hair rolled into long dreadlocks. Finally coming to rest on the chocolate brown eyes she had seen earlier.

"Hello, love. What might your name be?"