Forever A Pirate

From Thief to Pirate
An Intro to Jake’s Life on Tortuge

Jake was a born thief, in a city full of rogues and pirates. Being a thief took a certain amount of daring in Tortuga. The port had clear lines of acceptable behavior and iron clad territories. Unspoken guidelines that even the fiercest pirate obeyed. One didn’t play hawk when sitting in the nest, that was for the open sky.

This meant, for those who lived in the harbor, that Jake could pick pockets along the wharf, but not near the rooms he and his mother shared. And he avoided the tavern where she waited on tables and helped in the kitchen.

There were several free zones, one being the narrow streets where the whores spent money. Those merchants with the daring to bring product to the port knew the risk they took, for the rewards were great. But the lad never stole from the ladies who plied the pleasure trade. For two reasons. Number one, the whores always knew the best gossip, the plumpest targets and who to avoid. Number two, he liked the ladies.

He may have been but ten years old, more or less, yet…he found the women tempting. And they liked him. Jake practiced his charm on them, and won confidences no ten year old (more or less) could be expected to keep.
Yet, he kept them, despite the offers to trade gossip for coin. Jake kept his word and he expected those around him to follow his code.

Unless he already knew them as liars, for some took pride in their ability to mislead. The ladies took delight in making certain he understood the ways of women, talking to him of ways to win hearts and more. They guaranteed he’d grow to be a man women would flock to.

His mother despaired of his chosen profession. She held high hopes of seeing see him take service with a profitable trade ship and become a clever merchant himself. But Jake didn’t care for ships. Filthy, leaky, full of foul tempered captains and too many men in charge, telling him what to do.

Jake preferred being his own boss.

This is the story of why this boy of ten (more or less) changed his mind and became a legend of the high seas and a man to be feared, admired and able to pick from the best, or worst, Tortuga had to offer.


“Hey, Jacob!”

“I told you not to call me that, Murphy. I’m Jake. And quit whispering, you’ll draw attention.” The dark haired lad, clearly in command, cocked an eyebrow at the taller boy.

“Sorry, Jake. I just…did you see the size of that purse?” Murphy bent close and Jake shoved him back to the rickety wooden bench.

“Nonchalant! And yes, I did. I also saw the three knives on his belt, the size of his biceps, and how his eyes roamed the street. That’s not a man to cross.” Jake eyed the passengers climbing from the merchant vessel. He’d know when the ripest plum rolled ashore.

The night before, Tiffany told him about a repeat customer from Hispañiola, expected on the next ship. “He promised me a pearl necklace last visit, and then I found he’d given it ta that cheap tart down at the wharf. Do yer best, Jake. He’s a bit round, wit’ blond hair he likes ta style in long curls.” She’d stroked his arm. “His keeps his purse in a secret pocket at the rear a’ his coat.”

He smiled at her and gallantly took her hand in his, pressed his lips to her knuckles. “I’ll bring you a pearl necklace, Tiff. Or enough gold to buy one on yer own.”

The sweet coffee colored girl curtsied to him, her glance wandering down his thin frame. He’d shivered and she laughed.

But she’d been right. The man in question sauntered down the gang plank.

Jake nudged at Murphy. “That one.”

“Really, he don’t look like much.”

Jake stood. “Just do it like we practiced. Be clumsy and make certain that pie ends up all over him.”

“I know what to do.” Murphy lifted the berry tart from the seat next to him. “You buy me another?”

“I’ll buy you two. Go!”

The taller boy climbed to his feet, and lowered his mouth to the delicacy, taking one bite, making certain to spread the berry filling all over his lips and chin. Then he sauntered into the street, taking another bite, not paying attention to the passengers, scattering in all directions down the road. One more bite and he ran straight into their pigeon, dumping the sweet desert over the rich merchant’s chest.

Jake ran out, chastising his friend and apologizing with all sincerity to the furious man. “Get out of her, Murph! You idiot! Can’t you tell a man of importance from a common sea rat?” He shoved his friend out of the way. “I’m so sorry, sir! Let me help you.” He danced around the mark, insisting on removing his coat. “I’ve got a clean rag, we can wipe this away. But we don’t want to damage this fine brocade!”

Flustered, the mark allowed Jake to drape the coat over his arm, and then the lad gingerly wiped at the red mess, actually making a fair amount of progress in clearing the man’s vest. Then he gallantly assisted the man to redress.

“Thank you, lad. Here.” He reached into his small vest pocket and handed Jake a small coin.

“Why think you, sir! And a fine day to you!”

Jake watched the dandy stroll down the street, the large wallet from the secret compartment tucked into his jacket. He’d also palmed what felt like a strand of pearls from the inner lining. Knowing the man would catch on quickly, he dashed down toward the water, turning into a dark alley.

Murphy leaned against a wall, eyes narrow. “He have anything worth taking?”

Lifting the heavy bag, Jake jiggled it, and the taller boy grinned.

Squatting, they emptied the bag on a large stone and divvied the contents. Jake took a few extra, explaining he had to pay his informant. “Now, you have enough to buy a dozen pies!”

“You said you’d buy me the pies.”

True, he had promised. The boys rose and wandered to the baker’s shop.

After, they parted, slapping each other on the back in congratulations. Jake wandered up the lanes to Tiffany’s hunting grounds. He hadn’t looked at the necklace yet, not wanting to flaunt the wealth where other brigands might be tempted to go after him. Jake was quick, but he knew when it came to strength he fell short in comparison to the gangs of older kids.

No one knew the alleys and byways as he did. He could climb like a monkey and knew the best places to reach the roofs, and which buildings would hold him, and which would send a pursuer falling between rickety rafters.

When he spied Tiffany, he nodded and winked. She grinned widely and kicked away the would be gallants trying to convince her to give them a feel for free. Taking Jake’s hand, she led him up the stairs to her small room.

He emptied what was left of the purse upon her sheets and split the take with her. Yes, this meant he took less than Murphy, but without her help he’d have nothing. She all but squealed when he pulled the necklace from another pocket.

“Jake! That is…oh! Boy, I wish you had a few more years on you!” She lifted the pure white strand to her neck and turned to admire herself in the mirror. “What do you think?”

His breath quickened more than a lad of ten, more or less, should. They gleamed against her deep cleavage, reflecting the richness of her mocha skin. He swallowed, and shifted on the bed, suddenly too aware of how the room held the heat of the Caribbean.

“Help me fasten them, lad.”

She backed up to him and lifted the hair from her neck. The fine line of soft curls, as it met the bare skin, caused another shudder to travel up his frame. He steeled his hands to not tremble as he worked the clasp, lightly stroking the cool beads.

“You shine, Tiff. You should be covered in pearls, just like these…” He surprised himself with the timbre of his voice, both soft and deep at the same time.

She stilled and slowly shifted to look at him. “How old are you, Jake?”

He wanted to lie, he wanted to lie. Oh, god, he wanted to lie.

“My mother says I’m about ten, but she’s been saying that for far too long. I think she’s intent of keeping me at an age she thinks manageable.” There, that wasn’t a lie. It was what he believed. Honestly.

The whore glanced down at his body. “Old enough for your first kiss.” She lowered her head and with infinite care, brushed her lips against his.

He clenched his fists, wanting to touch her like he’d seen other men. But she hadn’t said he could. When she pulled away, a sigh escaped her warm mouth. “Jake, yer gonna break hearts.”

“I only want one heart…”

“Oh, and such a romantic.” She slipped from the bed and put a hand at the doorknob. “I need ta get back to work, love. I’ll keep an eye out for any deserving targets. You get back to your dear mother, and share that purse with her.” With a look he thought held regret, she slipped from the room.

He groaned and fell back to her bed, inhaling the perfume he stirred from the sheets. He knew not to linger and grudgingly left the room.
He’d see his mother got her share, even if he had to spare the truth to do so. In the end, he told her he’d earned it running errands for the ladies and though she crooked an eyebrow at him, she took the coins and tucked them into her purse.

His dreams that night were full of bare skin and pearls. And berry pies.

For several days, all seemed the same as ever. Until he realized he hadn’t seen Murphy for two days. He went searching for his friend, but he was gone. Just gone. It wasn’t uncommon for boys to sail off, looking to learn the trade of the port, but Murphy had never shown an interest in sailing. Jake thought it odd, but wasn’t worried.

He sat, eating his dinner in a corner of the tavern, watching his mother fending off the advances of a few drunken sailors. He didn’t worry, she knew how to deflect without offending. Glancing up, he blinked as the rich mark from several days past entered the room, followed by the dangerous merchant Murphy had commented on. The two men stood for a moment, searching the room. Instinctively, Jake ducked down, hiding his face.

A deep voice boomed into the space. “I’m looking for a slight, dark haired lad, with a fine tongue and fast fingers. Sharp featured, ‘bout yay tall. I’ve got the coin for the man who points him out. Been told he’s known as Jacob.”

Oh, damn.

Jake hit the tavern floor, underneath his table. He heard his mother reply. “There be no young boys in this tavern. They all prove too fast fingered. I got a son name a’ Jake, but he’s been at sea for the last month.”

God, she was too brave. One of the regulars kicked at him, nudging him to the back door, left open to encourage air flow. The tavern owner provided a shadow for him to hide behind. Those who knew him wouldn’t betray his presence to a pair of strangers, no matter the reward.

“Then it must be another lad of the same name. I’m offering five full doubloons.”

Too much. Someone would spill. Eventually.

Jake scurried out the back door, only to hear a shout from someone left to lookout. With lightning reflexes, he slipped from the grip of the watcher and dashed for one of his favorite routes to the rooftops. The pursuit followed from the streets, as he jumped from one building to another, knowing he was close to running out a place to hide. He paused, considering his next move.

A fleeting thought for his mother tried to take root, but he shook if off. Mr. Hallow would let her be hurt. The populace treasured her for the quick needle she wielded and her willingness to nurse the sick. And Sebastian was in town, that bear of a sailor would take on an army for her.

He squatted on one of the sturdier roofs, contemplating where to go next. The buildings to the east were older, the wood rotten and worm eaten…

“Now, lad. All I want is the pearls you stole…”


The man stood eight feet from him, a knife held ready to throw in one hand. Jake stood and backed up, toward the roof edge.

“I don’t got them. Traded them ta a captain fer ready cash!”

A crooked smile greeted that lie. “Least you ain’t trying to lie ‘bout taking them. But no captain be willing to cross me and those strands be mine. Now, the truth. Or I’ll split you wide open.”

One more step… Jake felt the brick crumble beneath his foot and with a cry, spun, diving for the roof to the east. It was a leap, but he made it and didn’t stop. A crashing thump from behind him let him know he was followed. He zigged and felt the breath of a knife kiss his cheek.
Bastard was good.

And he was fast. Jake had to take chances, half a block later, he dance along the edge of a boarding house he knew came near to falling down during the last storm. The far wall leaned toward the warehouse beyond.
In desperation, Jake snatched at the line he’d left ready for a last ditch escape and swung to the middle of the sagging roof. A curse sounded behind him.

“Damn you, scurvy ridden street rat! Take one more step and I’ll split your mother in two!”

Jake froze, and slowly turned, his heart gone cold.

“Now, toss that line back here.”

His mind spun, trying to find a way to see this monster take a fall. He took a step forward and grabbed at the rope, hearing the faint groan of the wood beneath him. Another step and he felt a beam beneath his heel.
“You leave my mother out of this.”

“Up to you, lad.”

He set his other foot at on the beam, and braced himself, flung the braided hemp to the big man. And took another step backward, slightly off the beam. The roof sagged a tiny bit. He bounced, gauging the strength, remembering the system of braces below him. Another step back as the big man gripped the line, preparing to swing over.

He didn’t have much time. The brute put his weight on the rope and, as he began his descent, Jake threw himself forward and down. The man swung above to land behind him with a crash. The planks split and the roof took a deep cant to the center of the building. A bellow signaled his prey was caught off guard.

Jake scrambled to reach the frame, praying it would hold him. The continual snapping of wood and falling timber caused him to glance behind his shoulder. The bully dangled from one hand, his other held a knife.

He was a bloody target! He let go of the solid beam and fell, hearing the solid thunk of the blade sinking into the beam he’d been clinging to. With all his strength, he twisted in the air and caught the end of the line from before. It slowed his fall just enough. And he clambered to another bit of framework.

The bully had landed on the plank, hanging by two bolts to Jake’s perch, and crawled toward him, even as the wood split. Jake held to the rope and jumped on the beam, throwing every bit of his sleight weight at it.
“I’ll see you in hell!”

With a final bellow the beam separated from the frame and fell, taking the brute with it. More wood fell, until all that stood was the wall he balanced on and the one kitty corner to it.

Jake listened, wondering if the rest had followed. He heard three voices, rising in disagreement regarding whether it was worth the risk to enter the collapsed building. The vote came out against it and they wandered away, bemoaning the chance to claim the reward.

He didn’t trust the man was dead. Nothing for it, but to make certain. Jake gingerly made his way down the support. And carefully stepped about, searching. He’d about given up, when a hand grasped at his ankle. He yanked free and lifted a flat bit of board. The hand fluttered, then went limp. Below the board, the man sprawled, a great splinter rose from his belly, blood painting everything below a deep black.

“You…cursed…brat! They’ll be others…coming… You’re already…dead!” A bloody foam bubbled about his mouth and he fell limp.

More would be coming? He needed protection…

He checked on Tiffany, but she had disappeared, her crib cleaned out. The next day he fought his way into one of the gangs, giving up the ideal of never taking orders. When Tiff’s crib was taken over by a new whore, younger but no less lovely, Jake made it his business court her and earn more than a kiss.

In a matter of months, Tortuga grew too hot as forces converged to see his mother out on the street. The next week, Jake boarded a ship, determined to earn enough to see her taken care of.

The rest is legend.


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