Title: Meet the Bootstrap Bill

Disclaimer: I do not own the characters or the franchise, merely the situations I put them in and such. And title inspired by a NewsRadio episode name.

Note: Pre CotBP

Warnings: M/M, sex, alcohol consumption, brief violence

A/N: Bootstrap is a bit...darker?...in this than what I usually imagine him to be. But please, enjoy! bwhahaha. It's kind of a weird exploration of his character. .

Comments are extremely welcomed and encouraged. :) Thanks for reading!


The night air was crisp and clear; a perfect companion to Jack Sparrow's mood. He had recently become the captain of a new pirate threat in the Caribbean; rightly christened the Black Pearl. It made port at Jack's favorite spot: Tortuga. He came, for the most part, in search of good strong men to crew his ship. The decent amount of alcohol consumption he would participate in was a close second.

He swaggered down the crowded paths, keeping a watchful eye for any man who looked worthy enough to be a part of his crew. There were not many, to his disappointment, but he had expected that. He reached the edge of the town, rolled his eyes in annoyance for having wasted good time that he could have been drinking rum, and turned to head back. As he did so, angry shouting caught his attention. Normally, he would simply walk away and think nothing of it. But it did not seem to him that this was the typical kind of fight likely to occur in the area. The ones he was used to seeing and taking part in himself were stemmed from drunkenness and stupidity – They were never over anything of importance. He drew closer to the four-man brawl and even though they were all drunk, it was also apparent the situation was rather serious. Three of the men were teamed against the fourth, beating him violently in the darkened alley. Jack watched him fight back pathetically before he altogether gave up and slumped to the ground against the building wall. The three advanced on him like vicious animals, and Jack turned away as he treaded lightly on the street once more. He did not get far before he stopped and contemplated. There was something about that man - about him fighting until he had no more, severe determination – that Jack knew he would benefit from having on his ship. There was an unknown quality that Jack could not place, but he knew that man would make a fine addition to his crew. He was not able to pass it up.

He went back to the alley, drew his sword, and sauntered over to the gang. None of them realized his presence, causing him to yell, "Oiy! What's the purpose of continuing to pound him senseless now that he's giving no sport? Where's the fun in that?"

"He done us wrong!" one of them hissed, and Jack leaned backward and made an unpleasant face due to the man's horrid breath.

"Alright, that may be, but it seems to me that you gentlemen have already won the argument, so why waste more of your precious time when you could be spending it getting much more drunk than you already are along with some better company than this scoundrel, ay?"

He removed a small bag from his inner coat pocket and tossed it at one of the men. The three huddled, peeked inside at the coins, and without any other coherent words, they trotted off in zigzag lines toward the nearest tavern.

Jack sheathed his blade and stared at the bleeding, battered male sitting on the ground. He could not tell if the pirate was still conscious. Slowly, he started to kneel, but the bruised man quickly lifted and cocked his pistol at Jack.

"Whoa, easy there mate," Jack spoke rapidly. "I wasn't the one that made you look like that."

"Then what do you want?" he responded in a very low and gruff voice.

"Well, now that you ask, I thought you might be interested in joining me crew."

The man laughed hoarsely and lowered his weapon.

"What's so funny about that?" Jack asked, sounding insulted.

"Why would you want me? I'm of no use. A pirate's life isn't lookin' as good as I thought it would. I've been kicked off of two ships for getting into too many fights with crewmates; I steal almost anythin' I can get my hands on-"

"And that fight just now?"

"That - I had taken his boots and cut them down to nothin' more than leather straps to wrap around my own for a good joke. He just found out about it." He chuckled at this, as if proud of himself. "He didn't find it as entertainin' as I did."

Jack squinted and pondered before speaking. "Boots. That was all about boots?"

"Aye; boots."

"I see……" He suddenly smiled brightly in his most charming way. "Well…..Bootstrap, I would like to have you as one of my crewmen. You sound perfect. What say you?"

He was quiet as if turning the proposal over in his mind, sighed, and responded, "Aye."

"Aye! Now! Let's get you up, savvy?"

Jack offered his hand to the fallen pirate and hauled him to his feet. He swayed and staggered, and Jack kept his grip on the man's shoulder to steady him.

"We should do a proper introduction," Jack said casually and held out his hand. "Captain Jack Sparrow."

Taking the offer, he shook and replied, "William Turner."

"Welcome aboard, Mr. Turner. Or should I just call you Bootstrap?"

William laughed a little as he responded, "Call me what you like, Captain."

Gold teeth flashed as Jack grinned. "Bootstrap it is."


Jack flung the door open and strode in, shedding his coat right away to hang on a rack nearby. His fresh crew member stayed behind uncertainly.

"Come," Jack commanded and pointed to the bed.

William obeyed the order and moved to sit on the piece of furniture. His captain closed the door, then went to the curtains and sliced a portion of them with his sword. William observed him suspiciously, but said nothing. Jack fished out a little bottle from his inner vest pocket and poured a small amount of the liquid onto the fabric. He at last sat down next to the other man and gripped his chin firmly. When he touched the wet cloth to one of the bleeding cuts, William attempted to jerk away, but Jack's hold tightened. He hissed as the dark haired pirate dabbed at wounds and wiped the blood off of his face.

"Oh, it can't be that bad," Jack voiced in an amused tone. "Stop dramatizing, mate."

"Easy for you to say."

"It had to be done. You'd make me look bad. I can't have one of my men looking like a rumpled raisin now, can I?"

"Apparently not. What did you put on that?"

"A special remedy I borrowed from a special lady I happen to be close with. Thick as thieves, we are."

"I see." He swallowed, and the sourness in his voice was gone as he muttered, "Thanks, Captain."

"You're welcome."

There was a period of silence before Jack announced, "There. All done. Much better."

He stood and sashayed to the dresser to fetch two bottles of rum. Upon returning to his crewmember, he handed over one and uncorked his own. William simply held it as if immobile for a moment before opening it, causing a wide grin to spread across Jack's face.

"Cheers, mate," Sparrow voiced happily and tapped his against the other pirate's, then took a large drink from it.

"Cheers." William mimicked the action without hesitation.


"Now tell me, my good Bootstrap Bill, a little more about yeself."

Jack's words had slurred more so than usual as he drank down yet another container of his favorite alcohol. He finished it off and rolled it across the floor to the decent pile they had started of empty ones.

"What would ya like to know?"

"Any dear, sweet, bonnie lass you left behind to go pirating?"

"Aye…..A wife. Left her in England with one son."

"Ah, a family man you were."

"More or less. What about you?"

"Just me ship. She's all I need."

"Where you headed?"

"Wherever we want to go. My compass…..It's unique."

William smirked and took a large swig of his liquor. "Well Jack, I suppose I should let ya have the rest of the night to yourself. I'm sure ye can find better company than me."

He made to get up, but Jack stopped him to sit once again beside him.

"Nonsense!" Jack said as his palm inched upward on William's thigh. He was close to reaching his maximum amount of rum intake, making him much friendlier than his usual flirtatious self. "You provide fine company, Will Turner," he spoke in a low, sensual tone. "All you need is more to drink and you have the makings of-" He rocked forward; close enough to where the other man could feel the warm breath against his skin. "-an opportune moment."

Bootstrap leaned back just as Sparrow was about to follow through. They searched each other's eyes for a moment, and Jack made a noise of disappointment.

"You think it's appropriate for me to sleep with my captain on my first night serving under you?"

"Well, I am the captain, and I see no harm in it. Besides, I could serve under you tonight if it makes any difference. How do ya like it?"

Without another word, Jack pressed his lips to the man's in a heated kiss. This time, William welcomed it completely. He placed his hands on Sparrow's tanned chest and slid them slowly downward to the pirate's belt. Carefully, he removed the compass and was about to put it in his own pocket, but Jack's slender fingers curled around his own firmly. Their mouth contact was broken as Jack pulled away and gazed at him with interest.

"You think it's appropriate to steal from your captain?" His handsome smile was present as he spoke. He released his grip and held out his hand, waiting patiently for Turner to return it.

"Sorry, Captain. It's habit," he said quietly, the first time sounding frustrated with himself. He gave it over and Sparrow put it to the side.

"You steal from all your bed partners?"

"Just the better ones."

"I knew I'd like you."

Jack assisted William in taking his coat off and kissed him hungrily once more; making sure their lips would not be separated unless there was a necessary reason. Turner worked furiously to remove the belt and striped sash from the shorter man's waist, flinging them to the floor to begin a heap of unwanted accessories and clothing. There was never a time when he had experienced such a need as he did then. The lack of sexual encounters due to being at sea for the past month had taken a greater toll than what he had originally believed. He found himself absolutely ravenous; already fully addicted to the person he was undressing at the moment.

Sparrow almost ripped Turner's shirt when he frantically pulled it over the pirate's head and discarded it to join his own shirt and vest on the floor. His flesh tingled incessantly from the rough caresses William provided. An insatiable lust was present within him, an exceedingly rampant thirst, and he sought to fulfill it wholly by the rather attractive male in front of him.

A muffled grunt came from Jack after he was pushed firmly onto his back. His head spun from his growing desire, not to mention the consumption of rum as well, and his nimble fingers took upon the task of undoing the buttons on his crewman's trousers. William's hands flew through the chore of unfastening Jack's and tugged them down the slim hips of the captain. Sparrow did not lie naked alone for long; his partner for the night got rid of his own and threw them to their mound of clothes.

Turner glided his mouth over the smooth contours of Jack's face, then his neck, and was about to move further downward when rowdy squeals from a prostitute and grunts from her customer intruded on William's progress. He lifted his head and met Jack's demanding stare. Sparrow rolled his eyes in aggravation and clicked his tongue.

"Well, go on. Finish me off," he huffed irritably, raising his hips off the bed for a brief stint to meet William's.

"I can't if I have to listen to that."

"Make you lose your concentration or somethin', ay?"

"Yes, as a matter of fact."

Jack sighed in exasperation. "Pretend you can't even hear them, alright?"

Turner's expression gave away that he would not be continuing anytime soon unless the ridiculous noises spawning from the other room ceased. Jack muttered something quietly in displeasure before he turned onto his side and pounded on the wall behind the bed with his fist.

"Keep it down, will you! It can't be that good!" he yelled. The couple's commotion faded and Jack moved to rest on his back once more. "Satisfied? Now, if you please, go on."

With an entertained smile and shake of the head, William's hand traveled Sparrow's leg; gently squeezing his calf and the tender underside of his thigh every now and then. Jack's calloused palms roamed over the broad shoulders and dorsal side of the stern man above him as he continually shared breath with him.

After a long while, the carefree commander of the Black Pearl shifted his lips to Turner's neck; licking and biting it playfully. William returned the gesture, though he sucked rather fervently, creating a blotch of darkened skin on Jack's throat. As he did this, his hands ventured over the other's form and found Sparrow's hardening member. Jack squirmed and let out a quiet sound of content when he felt the fingers clasp around him. A warm tongue slid over his torso and caused him to close his eyes briefly and grab a fistful of Turner's dark hair. The sensations made him dizzy; within several minutes, he was tottering on the brink when suddenly –

The touch was gone. All of it.

He growled dangerously, expressing his immense disapproval.

"Do you have some?" William questioned in a tone Jack heard as mocking.

"Of course I have some. I've got what ya need. All that's left for you to do is take it." He smiled wickedly. Turner cocked his head and gave him a serious look, and Jack sighed as he responded to what his shipmate had actually meant. "My coat pocket; right side," he grumbled.

William got up to get the slick substance, and Jack snuggled into the bed to become more comfortable. The tall lad returned on top of his company and rubbed the oil on his arousal, while Sparrow separated his legs and crossed them on Turner's back with his knees kept high. No more time being spared, Turner penetrated Jack with more force than the beaded-haired pirate was expecting. A loud groan escaped Sparrow, and William continued pushing himself into the man's welcoming body. He stilled after he was wholly within the heated cavity. Sparrow's breathing had quickened slightly, his heart thumping powerfully, and he swallowed several times before a subtle tightening of his legs around Turner signaled him to go on.

William brought his hips back, then cautiously rocked forward. He repeated the motion a few times, making Jack perturbed and anxious.

"Oh, for God's sakes, man!" he exclaimed hysterically. "You can afford to be a bit rougher than that with me. This is hardly the first time."

A wide grin spread across William's face, and he heeded the words. He shoved himself in again violently; Jack cried out gloriously. He was about to do it once more, but the couple in the next room started their clamor again.

Turner ceased and muttered, "Good Lord."

"You're going to let a little noise ruin our enjoyment? You know, if you'd like, I can be just as loud…..drown them out; might help you perform better," he ended with a sly smile.

"Oh really?"

"Find out for yeself, mate."

The caged madness set itself loose. William began thrusting fiercely without anymore hesitation. Jack moaned boisterously between his panting; taking the liberty of embellishing the sounds he made for his own delight. They apparently had an effect on Turner, for he joined Sparrow's trembling vocals and sped his pace.

Neither acknowledged the banging on the wall from the other room, nor the enraged shouting that accompanied it. They felt no reason to quiet themselves now.

Jack closed his eyes tightly and arched his back as a coarse palm explored and groped his perspiring body. He latched onto William's shoulders and dug his nails into the soft skin. William responded with a bruising kiss, and bit Jack's lip strongly before pulling away. Jack whimpered slightly and licked the blood that was trickling from the wound.

Sparrow gave one final moan before he spilled himself freely. Turner climaxed soon after, shutting his eyes and bowing his head when he did. The room was filled with the sound of their ragged breathing as each recovered from the exertion. William shifted to lie beside his leader and gazed at the ceiling. His anatomy tingled pleasantly, and he sighed deeply. When he at last averted his stare, he looked to Jack and found the pirate passed out completely.

With a small laugh, his eyelids fluttered closed and he fell asleep.


The next morning Jack Sparrow woke slowly, snarling at the bright sunlight that met his frazzled hazel orbs. He yawned, stretched, and glanced behind him to discover William Turner resting tranquilly. His eyebrow arched and a broad, mischievous grin formed as an idea formed in his mind.

Silently, he got up, dressed hastily, and retrieved Turner's boots.


"Decided to finally join me this morning?"

Bootstrap focused on the person sitting in the chair watching him from the other side of the room. He exhaled a breath, shrugged, and lazily clothed himself. Jack observed with faint interest.

"That was too much for me last night," Bootstrap croaked with a smile.

"Too much rum or too much me?" Jack replied in a rather cocky voice.

"I'm not sure."

"True enough. Now, what say you about getting off this island and heading for the open water? The crew's probably waitin' on me already."

"Aye. All I need are my boots." He searched around for the missing items for a minute before he was enlightened as to where the lost belongings were.

"Yes, those." Jack stood and crossed over to his deckhand. "I'm deeply sorry to have to tell you this, Mr. Turner, but through an entirely uncontrolled set of circumstances….your poor boots happened to become these."

He presented several strands of leather to Bootstrap, showing just what the man's shoes had been made to be.

"Couldn't resist, mate," Jack said cheerfully.

Bootstrap chuckled and wrapped what was left of the material around his feet. "That's a good joke, Captain."

"Isn't it? Though I suppose we should find you a pair of new ones before we set sail, Bootstrap Bill."

"I would appreciate it."

Jack grinned, gold teeth glinting dimly. "Good man; good pirate."