If tentacle porn squicks you, you may want to turn back now!

Title: The Bargain for the Whelp
Characters/Pairings: Jack/Will (kind of), Jack/Davy, Jack/OCs
Warnings: Rape, M/M
Summary: "What can I give you to ensure the safety of young William Turner?"
A/N: This was inspired by a doujinshi of Jack/Davy I recently got. It looked so hot, I just had to give it a try. :) I don't know if I like the ending, but nothing else came out.
Bit of fluff between Jack and Will; maybe that could be a warning. ;)
AU; takes place during DMC when Jack and Davy are agreeing upon the 99 souls.


"I keep the boy – a good faith payment. That leaves only ninety-nine more to go." Jones laughed before adding quietly for only Jack to hear, "Best begin quickly, Sparrow. Who knows what I can do to the lad in three day's time?"

Jack opened his mouth, but he found himself speechless. It was the first time he had been completely silenced during his conversation with the captain of the Flying Dutchman. Jones grinned mischievously from witnessing the uncertainty that sparkled in Jack's eyes. Apparently, the boy meant more to Sparrow than he let on.

"You wouldn't do anything to seriously harm him, would you?" Jack said as he frantically thought up a plan. "What good would that do? Here he'd be – a fresh, temporary member to your crew – and you'd have to waste time takin' care of him afterward."

"What's this about temporary?" Jones inquired, amused.

Jack clenched his teeth and stared at the deck. After a minute, he chirped optimistically, "Why don't we go into my cabin and strike a deal, eh?"

"Not yours; mine."

Jones grabbed the pirate's arm strongly and began walking to the railing. Before they went over, Jack suddenly found himself aboard the derelict Dutchman in the captain's cabin. He glanced around curiously, and as if it were his, he wandered about the area casually.

"What can I give you to ensure the safety of young William Turner?" he asked as he ran his fingers over the slimy organ keys. He pressed down on one, creating a loud tone to sound that made him jump. "And to keep you from press ganging him to swear an oath?"

"What could you possibly offer? You already owe me your most important possession."

"Ah yes. My life, right? Or, lack of a life seeing as how I'll be bound to this forever. But surely there's somethin' on me that suits your fancy, ay?"

Jones looked at him blandly while he studied Jack from head to toe. Sparrow was distracted by the unknown growth on the organ pipes. He made disgusted faces, though continued his inspection like a child would. As Jones observed him, a notion formed in his mind. This man needed to learn that he was not powerful; he was not in control of the situation like he thought. It was apparent that Jack had no respect for the bargain he had struck thirteen years ago, and he played off the position he was in now as if it were nothing.

"I've come to an idea of what you can exchange."

Jack snapped his head up, grinned, and sauntered toward the captain. "Ah! Have you? What do you want?"

"You."

The pirate's brow furrowed. "Pardon?"

"Did ye not hear? You are the trade; your body to be used twice."

Jack swallowed and the color from his face drained. An overwhelming sense of anxiety and nausea washed over him. From the deviant glint and firmness in Jones' blue eyes, Jack knew he would not be exploited simply for the captain's pleasure. It was an assertion of dominance.

Sparrow rapidly concealed his insecurity and stated with utter seriousness, "Surely there's somethin' else? How about another hundred years of servitude, ay? Besides, I'm really not as good as you think, mate."

"It's not like you to say something that does not flatter yourself."

"Well, in this case, I'm just tryin' to prevent you from terrible disappointment."

"Even if ya are, that is my offer. Take it or you will come to find him looking nothing like the way you left him."

Jack's expression faltered to intense uneasiness. He chewed nervously on his right forefinger as he debated with himself. It was an enjoyable sight to Jones, witnessing Sparrow overcome with worry for someone else and undoubtedly for himself.

After several minutes, Jack lifted his head to gaze directly at the captain. His usually lively eyes were fraught with unwanted helplessness.

"We have an accord," he spoke vaguely and held out his hand. He winced from the cold, slimy, half-tentacle hand that grasped it.

"Start undressin', Sparrow. I'll summon for the boy."

Jack's eyes widened in alarm. "What for?"

"To watch. He should be here to witness what has been sacrificed for him."

Jones chuckled wickedly from the crestfallen look Jack had. Yes, this was the perfect deal, he thought.

Jack removed his effects with no problems, though he had difficulty stripping his body from the protecting clothes. His hands shook as he willed himself to discard his garments. When he was entirely naked, he bowed his head as if ashamed and attempted to cover himself with his palms; he soon gave up and let his arms dangle at his sides.

In a corner as if abandoned, a few crates were stacked together. Jones dragged one to Jack and said nonchalantly, "Something for you to sit on while you fulfill your end of the bargain."

"What, no bed?" Sparrow questioned as confidently as he could.

"I prefer this."

Just then, the door opened. Maccus and Palifico entered with a struggling Will Turner in their grasps. They stayed a decent distance away from the two captains. Will immediately ceased all movement when his brown orbs landed on Jack's quaking, exposed frame. His mouth fell open in astonishment, and his features clouded with fearful puzzlement. A sense of indecency sprouted in him for gawking at the man's body. He hurriedly looked away, though continued to steal unabashed glances at Sparrow every now and then.

"Why not fill the lad in with what's been done," Jones prodded with a devilish grin.

Jack raised his head and met Will's stare for the first time; it made the young man breathless from the frailty within the eyes. "I value you as a crewmember, William," Sparrow began softly. "That's why I've offered myself to satisfy a deal to guarantee your safety while you're here."

Will turned his attention to Jones, rage flaring in his eyes. "You heartless bastard," he said harshly. "Let him go!"

"Rest assured, Master Turner. He will be once he's upheld his end."

Jack inhaled sharply from the sudden feeling of tentacles inching down his shoulders from behind. They forced him to sit on the crate and started to explore his torso and abdomen. He grimaced as the circular suckers feasted on his flesh hungrily; they were unexpectedly prickly, creating a number of tiny cuts to adorn his tanned skin. Two sticky tips toyed with his nipples, wrapping around them when they were stimulated enough to harden. Sparrow shut his eyes tightly as if everything would go away if he did not look. His slender fingers latched onto the edges of the crate and increased their grip with every gentle tug on his sensitive areolas.

He gagged as three slipped into his oral cavity. They played with his tongue, causing a repulsive taste to fill his mouth. The suckers caressing his lips made them incredibly dry; they cracked, and trickles of blood ran onto his chin. He resisted the aching urge to bite the eager feelers, knowing it would only bring about more discomfort for him from Jones.

Will watched in horror as Jack became covered with the tentacles of Jones' face; they had grown, making them approximately the length of Jack's entire being. The indescribable, quiet noises that came from the intruders on the pirate's frame made Will nauseous. They were crawling everywhere on Sparrow's body, inappropriately molesting depravedly. A low chuckle came from Jones as Sparrow released a strained groan. Several of his appendages traveled to Jack's manhood, making the pirate emit a quivering moan as they wound about it. They pulled and fondled the flaccid member until it became erect. Utter mortification started to cloud Sparrow's tense face; a stab of pain went through Will from seeing the change.

Jack's legs were parted, permitting the tentacles to venture between them as well as wrap about them to hold the slender limbs in place. Will made to help him, but was not strong enough to break free of the crewmates' grips. He suddenly found himself angry with the Black Pearl's captain as he watched the misuse of the man's being. Jack gave no fight, and it disgusted Will to observe him submitting himself to Jones' domination. The disapproving feelings were quickly quelled by an abrupt wave of compassion.

The sight that met the former blacksmith's wide eyes next made him want to vomit. A tentacle made its way into Sparrow's body, causing Jack to throw his head back and whimper helplessly. Another one soon forged itself into Jack's opening, followed by another. Jack trembled and moaned in pain. The three feelers pumped in and out of the pirate's thin frame as the others continued to grope him elsewhere; two were still focused on Sparrow's arousal, working diligently to bring him to climax. The scream that came from Jack made Will feel as if he had been hit powerfully in the stomach. A fourth and rather large appendage shoved its way into Jack's warmth. They twisted and stroked deep within him; Sparrow writhed about in agony. Slowly, they retracted, allowing Jack a short break to catch his breath. He wailed loudly when they violently penetrated him again with great speed. He panted heavily and was drenched with sweat; the perspiration hid his scorned tears.

Despite the torturing pain, Sparrow did not once ask or beg Jones to stop.

One last caress made Jack spill himself onto the captain's limbs. The abuse was not over, however. The feelers inside of him carried on with their task. Blood leaked from the pirate's opening, and he attempted to smother numerous cries from experiencing his tender muscles tear.

At last, they withdrew from him and were dripping with red liquid. Jack collapsed back onto the crate, gasping for air. Gentle sounds escaped his parted lips as he lay limp. Jones' tentacles returned to their normal length, and he laughed from Jack's sheer exhaustion and torment.

"That be one," he cooed above him. He turned his head sharply to view Will, who was hunched over and vomiting. "A just reaction, Master Turner. Can't look at him the same. Vile, is he not?"

Without warning, he struck Jack's visage powerfully with his sharp claw. Sparrow fell onto the ground with a wounded groan.

"Return the boy to his duties then come take care of this wretch," Jones stated and kicked the pirate strongly.

Will called Jack's name, but the man did not move. He yelled again, yet it was silenced from the slamming of the door.


The gentle rocking of the ship would have lulled him to sleep had it not been for the lingering pain snuggling his body. He did not care that the decrepit wood was damp and sprouting bits of sea wildlife; he was content with being allowed to rest at all. The blanket he was supplied with covered his nude frame up to his chin. The pathetic pillow cradled his head as he stared unblinkingly ahead.

The sound of graceful footsteps perked his interest, and he looked to see who was coming closer. Will sat down beside him and forced a reassuring smile onto his countenance.

"Hi, Jack," he said tenderly.

Jack grinned, hoping it would put the young man at ease. "Hello William. Curious findin' you here. I figured you'd still be hard at work on deck." He winked, arousing a small laugh from his company.

"They sent me in here to take care of any injuries you acquired that may be serious. Especially that one." Will pointed to Jack's left cheek, which sported a long, jagged, grotesque gash – courtesy of Jones.

"It'll be fine. Ya don't have to waste your time."

"It's not a waste of time, Jack. I want to make sure you're all right." There was more to the statement other than referring to the laceration.

The confident glint in the pirate's alert eyes was snuffed. His expression lost any sort of joking, playful persona. "I'll be fine, Will," he voiced faintly.

Will turned the wet cloth over in his hands, pretending to study it as he gathered the courage he needed. When he felt he had it, he cleared his throat and cast a quick glance at Jack.

"Why….Why did you-"

"Offer myself?"

Will nodded. "Why not barter with something else?"

Jack released a weary sigh and said quietly, "There was nothin' around I could barter with. I'm on his playing ground now. Besides, I'd rather give up meself instead of somethin' that has any sort of real value or importance. It's not like this old body hasn't been through it all. The unpleasing aftermath will go away soon."

"And the….shame?"

Jack shot him a threatening look, warning him to say nothing more. Will mumbled an apology and stared at his hands once again.

"May I ask you another question?" Will inquired after a period.

Jack shrugged, though remained silent.

"Why do you care so much for me? Why put yourself through something so horrendous such as that? I'm capable of taking care of myself."

The pirate shook his head and closed his eyes for a moment. "You'd be eaten alive on this ship, Will. They're a rather blood-thirsty bunch. Believe it or not, I really do have a heart. Just takes the right kind of something to make it work. After what he told me, I had to make the deal. Couldn't risk anything happening to ya. I know you're capable, but you don't understand what he's capable of. And I couldn't take the chance of him forcin' you into an oath to serve aboard this hideous ship either."

Will frowned, confused. "Why? You were going to leave me here to settle your debt anyway. Why bother?"

"We would've come back for ya, mate," Jack answered with a genuine smile. "Eventually, of course. You don't belong here, nor do you deserve to have that or somethin' equally as awful done to you. You're an honest, good man; and I'm sure you've never committed any sins in your lifetime. Me, I've committed a number of them – probably can't even be counted. I'm used to being used or using, but someone such as yourself should never be exposed or endure something like that."

"So you truly did sacrifice yourself for me," Will said, baffled.

"Yeah," was the quick reply. "I guess you could put it that way."

Will raised a slightly tremulous hand to the pirate's cheek and dabbed the cloth against the cut. Jack hissed and stiffened, but leisurely grew accustomed to the intense stinging. The blood and black grime was wiped away in a short amount of time; Will touched the rag to Jack's other cheek, forehead, and neck before resting it in his lap.

"Thanks, mate," Jack voiced graciously.

"You're welcome."

"Can you do another favor for me?"

"Of course."

"I need to get this revolting taste out of me mouth and my lips were sucked dry."

"I'll get you some water."

"No, not water. I don't trust it's….cleanliness," he finished and waved his fingers as if to emphasize a point.

"Then what can I get you?"

Something shifted in Jack's gaze, and Will was surprised to see a hint of embarrassment. "Never mind. Nothing."

It took the young man a moment to come to the conclusion of what Jack wanted. Hesitantly and full of apprehension, he leaned down to where his face was mere inches from the pirate's. Jack stared at him with uncertainty, but it did not last long. Will pressed his lips to Jack's, who responded ravenously. The intimate kiss made Will tingle with rapture and an unbelievable amount of pleasure. He did not even realize that his tongue had slipped into Jack's mouth until a passionate moan sounded from the older man. It caused him to come to his senses, and he pulled back hurriedly. Jack's eyes opened in disappointment and dejection? Will shoved the notion aside. A beguiling smile formed on Jack's face and he sighed in satisfaction.

"Ah, much better," he said casually. "Thank you."

"You're welcome." The young man's voice quivered. "When are you returning to the Pearl?"

"I think he wants another romp with me. After that, I'll be free to go."

"I'm sorry, Jack."

"For what? I'll just be glad when it's done with. Nothin' to worry about."

The cabin door abruptly opened, letting Jones and four other members of his crew enter. The wicked grin on the octopus man's visage made Will uncomfortable, though Jack did not seem to notice it. Jones nodded, and the two crewmates dragged Will away from the pirate and held him strongly. Jack caught on and sat up quickly.

"Once was quite enough for him," he stated sternly, though with slight fear. "Let him go."

"He should see the deal completed."

A nod was given by the captain, and the other crewmen hauled Jack to the crate he had been sodomized on the first time. Will had a side view of the pirate this time, and he stared unblinkingly as Sparrow was bent over the box.

"Stop this!" Will shouted madly. "Let him go! Haven't you done enough?!"

Jack rested his turned head on the coarse, wet wood and gazed sorrowfully at the young man. There was resignation in his once obstinate and charming eyes; Will wanted to weep from the sheer misery the man allowed to show.

"Jack," he whispered almost inaudibly.

A tear dripped from Sparrow's eye, over the bridge of his nose, and splattered onto the wood. Silently, he said, "I'm sorry, Will."

At that instant, Will wished he could disappear, melt into the deck; it did not matter. The guilt suffocated him.

A weak grunt sounded from Sparrow as Maccus penetrated him with a barnacle-encrusted erection. It was an excruciating sensation due to the rough texture and tiny movement from the growth on the arousal. Jack concealed his face in hopes that no one would know he was crying from the anguish. Alas, Will saw the shuddering of his shoulders and quick intakes of breath. He knew.

Jack's hips were constantly slammed against the crate as Maccus thrust vigorously in and out of him ceaselessly. The pirate hugged the sides of the box tightly, mostly to keep his legs from crumpling. A clammy hand snatched the long braid in his hair and pulled hard. A pitiful whimper was heard as Sparrow's head was forced up. His glistening chest heaved up and down as he breathed heavily. His breath hitched when he felt another hand close around his manhood. It commenced rubbing him incessantly, causing him to moan uncontrollably. Eventually, his member became firm and throbbing; white liquid leaked from the tip.

The propulsions stopped at last as the creature ejaculated within him. It was not long before the next crewman was conquering his body. He imitated the ministrations Maccus had used, bringing Jack to orgasm minutes later. Sparrow could not hear the mocking laughter or encouragement from the oceanic spectators. He could only focus on Will's pleas for them to stop and the thumping of his own pulsating heart.

The third one defiled him brutally and leisurely and then the fourth followed suit. Jack was in a daze; fatigue engulfed him and the pain made his head spin. Nevertheless, the maltreatment was not over. The familiar feeling of slithering tentacles brought about vomit in his mouth. He swallowed it and forced himself to think of something else – to detach himself from the situation. They shrouded his body, and four weaved themselves into him. Everything was being ripped within him. He did not believe that the hoarse, wounded shriek that resonated throughout the area came from him, but the entertained, sadistic looks on the four crewmembers faces told otherwise.

After an eternity, they pulled out and were once more colored with blood. Jack was shaking incessantly as he laid himself on the ground. He refused to meet Will's eyes, knowing that the young man was staring at him.

"Take him out," Jones ordered.

Will fought against the two holding him, but it was to no avail. The cabin door shut securely behind him once they were out.

"Good to do business with ya, Jack Sparrow," Jones said with malice. "I suppose you don't want to return to your beloved Pearl like this." He threw the pirate's shirt and breeches at him. "Get dressed and I'll return ye."

"He's safe, yes?" Jack asked breathlessly.

"Safer. He may bring punishment onto himself, but it will not be as severe as it could have been."

The creature exited, and Sparrow remained where he was for a lengthy period as he sobbed freely. Not until he could control his emotions did he begin to put on his attire. When he was fully clothed – effects and all – he left the room, discovering Will waiting for him. His heart sank; Will was the last person he desired to see or speak with.

"Jack, I-"

"Don't pity me, Will," Sparrow growled ominously. "I don't need your sympathy. It's done with."

A brief moment passed before Will broke the silence. "Do you have hidden feelings for me, Jack?" he inquired somewhat shyly. "Is that why you went through all this? All of this for me?"

Jack shrugged. "You're a….friend," he stated warily. With a bit more conviction, he said, "Yes, a friend. That's it."

"Do you wish we were something more?"

Jack stared at the young man for a time with utter vulnerability conveyed in his defeated eyes. He said nothing and after a brief period, he walked away, grimacing from every step. Will watched him stroll to Jones and in seconds, the two were gone. The captain returned shortly, and Will regretted not being provided with an answer.


Gibbs rushed to Jack's side and caught the pirate before he fainted. He slung Sparrow's arm across his shoulders and placed his own about the man's waist.

"Jack, what happened?" he inquired worriedly.

"Nothin'." The captain smiled, though Gibbs saw right through the mask. "Just tired, that's all."

"I'll get ya to your quarters."

Jack groaned as he treaded with Gibbs to the cabin. When they arrived at his bed, he eased himself onto the piece of furniture extremely slowly. A quivering whine escaped him as he stretched out on his back. Gibbs had an idea as to what occurred, though he did not ask again. Sparrow obviously wanted it to be unknown.

"Where we headed?" he questioned instead.

"Set the course for Tortuga with all speed. We need ninety-nine souls, and he was mum on the condition in which these souls need be."

"Aye. Tortuga."

He left, leaving Sparrow to stare aimlessly at the ceiling. His mind drifted to Will and the young man's inquiry. He sighed exhaustedly and closed his eyes.

"He's safe, just like I promised," he muttered. "He will be. And he'll be able to be with his dear bonnie lass again. They cause me too much trouble, those two."

If all went well, Will would acquire the key to the chest and his own freedom would be guaranteed. It would be repayment for the Hell he went through for the young man.

"All that matters now is that damn heart….And he'll be fine, I'm sure."

Everything depended on Will. His well-being was quite assured, and Jack hesitantly put his faith in him because of that.

He surrendered to the belief that the bargain was not made in vain. It would help him attain his own ends, and his heart was content from knowing the person he had unwanted feelings for would be unharmed.

Nothing could go wrong.