Title: Dead Man's Chest
Rating: NC-17
Pairing: Captain Jack Sparrow, Will Turner, James Norrington and various permutations thereof
Warnings: character death, violence, non-con, spoilers
Summary: 15 men on a dead man's chest, yo ho ho and a bottle of rum!
Disclaimer: At no point do I claim any form of ownership of any of the characters depicted in this piece. My representations of them are not necessarily indicative of the intentions of their original creators. The plot in which I place these characters holds no relationship to their original context. I make no profit from borrowed characters. Don't sue me.
Word Count: 2004
Notes: Don't overlook the warnings. I implore you, for the love of all that is holy, do NOT overlook the warnings. If you have an inkling that this sort of thing will rub you the wrong way, now would be the time to stop, before you're reading this like one watches a train wreck. And then you'll be mad at me. But I warned you.

III Proper Training

"Get up, you lazy dog," Will prodded, roughly shoving Jack's shoulder.

Jack murmured some nonsense in reply and fished his hat from the night table to put over his face. Will lifted it off and frowned when Jack pretended not to notice.

"Damn it, Jack," Will muttered.

"Mrmmm… Haven't had enough of me training yet, Mr. Turner?" Jack grumbled teasingly.

"Is that all you ever think of?"

"No…" Jack said, picking his brain for something else he might think of. He reached for his flask and shook it. Empty. "Why is the rum always gone?"

"Ah. And rum. How could I forget?" Will said, eyes rolling good-naturedly.

Jack sat up gradually and hung his feet over the edge of the bed.

"My effects, please," Jack extended his hand for Will to give back the hat. "We'll be needing more rum before this night begins." It was already midday, their midnight romp having tired them out more than expected. No one had come calling and so neither were roused by the cock crow.

Jack took the hat and dressed himself quickly, flashing a lopsided grin in Will's direction before dashing out the door to trade God-knows-what for more rum and oil. Will shouted after Jack not to get into any trouble and Jack waved him off indifferently, trotting away down the road. Will worked during the day to keep his mind busy, but ultimately was too concerned to work very hard. Jack returned a few hours later with a seemingly uncharacteristically large jug. Will squinted his eyes and looked carefully, but could find no evidence of what Jack had traded. Better not to think of it.

Will approached Jack who was gleefully humming a little tune and shouldered the jug to take inside.

"What is it you need to convince me of with all this?" Will asked, only half joking.

"Bilge," said Jack, "the Commodore has done all the hard work already. I won't be bothered convincing you of anything."

Will frowned dramatically at the mention of the Commodore. He would have protested Jack's remark, but Jack cut him short.

"Again with your worrying. You vex yourself. Come inside and have a drink with Captain Jack. Unless, of course, you find my company less than pleasurable." Jack did an exaggerated mimicry of a seductive woman and Will couldn't help but laugh, in spite of himself. His mood lifted immediately and he followed Jack inside.

Will thumped the jug down on the table and produced some mugs from a cabinet. Jack sat down and invited Will to join him with a charismatic wave of his hand. The pair drank until they were quite bawdy, but carefully avoided the motivations for their flirting. Finally, Jack leaned back in his chair and adjusted himself.

"I say, Mr. Turner, are you about ready to begin your training?" Jack asked roguishly.

Will blinked. Suddenly, he wanted to jump ship, but he tried to calm himself and think of his purpose. This, of course, turned his thoughts to the night before and his reservations were considerably diminished.

"Aye," Will bellowed, drink coloring his cheeks. He puffed up his chest and did his best to look dignified. His expression wavered for a moment when Jack sat watching rather than responding. Jack laughed when Will faltered and the chuckle turned into a full belly laugh, which cheered them both.

"Come on," Jack said, "let Captain Jack show you the ropes." With a nod of his head, Jack motioned charismatically for them to begin. He didn't wait for Will to respond, but immediately began to take off his boots and belts.

Jack took the bottle of oil he'd procured and placed it on the table. He took off most of his extraneous clothing and reclined back on the chair, watching Will move through the room. Will anxiously avoided Jack's eyes, removing his jacket and shoes, and seated himself on the chair closest to Jack.

"Don't fret, luv," Jack spoke softly, motioning for Will to approach. Will scooted his chair over. Jack sat up abruptly and made as if to kiss Will, but instead, left his lips tantalizingly close without touching.

"Jack," Will breathed, almost inaudibly.

Jack didn't know what he was waiting to hear, but he decided that was adequate. Jack rose to his feet, grabbing Will by the collar and pulled their faces close.

"Let me have you, Will," Jack growled, hot breath spilling onto Will's face.

Will said nothing in reply, but let his eyes fall closed.

Again using Will's clothes for leverage, Jack pulled Will so close that their knees knocked together. Jack's eyes scanned Will's face for signs of... Well, signs of whatever might impede progress. Finding only bated breath and beads of perspiration, Jack kissed him fiercely. The force of Jack's sudden kiss and the resulting arousal almost knocked Will off his feet. He leaned heavily against the table with his hip as Jack pressed against him. Clumsy with drink, Jack leaned back to breathe.

"Mr. Turner," Jack spoke theatrically, voice deep and hoarse. "I am the teacher this evening and I could begin your training right here."

Will stared dumbly, one eyebrow raised.

"Right on this table," Jack paused for effect.

Will's eyes widened in surprise. He tilted his head and looked quizzically at Jack.

"Right... Now." Jack pronounced in an exaggerated parody of seduction.

With a gilded grin, Jack shoved Will backwards onto the table. Will grunted when his back hit the surface and he pulled Jack down by his shirt. Not one to be put off by a little horseplay, Jack put considerable force behind the grinding of his hips. Jack mounted the table expertly and straddled one of Will's muscular legs. This activity very much reminded Will of their last and he moaned in anticipation.

Jack, however, had ideas in mind quite different from the excursions of the previous evening.

"Mr. Turner," Jack spoke between heavy breaths. "I implore you to prepare yourself for something wholly different from what you imagine."

Will nodded. He didn't know what Jack meant, but he was used to that... That and trusting Jack anyway. Jack saw the uncertainty in Will's face.

"Have I ever given you reason not to trust me?" Jack asked.

Will gave him a warning look, but Jack ignored it and stole another kiss. Jack's tongue was probing and hot as he extended it past Will's lips. Will breathed heavily through his nose and tangled his hands in Jack's hair.

"You never answered me," Jack said, pulling away a few inches.

"What?" Will asked, hardly able to think. "Trust you?"

"Let me have you," Jack whispered, more demand than request.

"Aye, Jack," Will bit his lip nervously.

Jack smiled and without making a sound, sat Will up and removed his shirt. Will slumped back down onto the unforgiving wood of the table and Jack stood up to remove what remained of his clothes. As usual, Jack had no reservations about nudity and did not think to pause in removing Will's pants. Will tried to hide his blush as Jack undressed him fully, but he didn't worry long about Jack watching him. Jack bent his head down to lick the salty summer sweat on Will's neck and sighed.

He climbed back up onto the table, wiry limbs straining artfully as he balanced himself over Will's prone body. Jack kissed Will gently to distract him from the finagling of the bottle of oil. He poured some of the oil into his hand, rubbing generous amounts of the slickness over his fingers. Jack put down the bottle and used his clean hand to rub the front of Will's body, the slick hand moving ever-so-slowly back. Will must have known what was coming, but he still twitched when Jack pushed a digit in. He squirmed but didn't wince.

Jack tried to be soothing in his motions and he moved his finger very slowly. Carefully, when Will seemed to have relaxed some, Jack crooked the finger. When he did this, Will gasped, having felt no other sensation akin to it before. The muscles in his legs and back clenched and he arched upward, whining for more. Jack raised a sculpted eyebrow at Will's response. Absolutely fascinating. Undeniably arousing. With a half-stifled groan, Jack slid a second oiled finger in.

This time, Will drew a sharp breath. He whimpered when Jack twisted both fingers, stroking him gently. Poised gingerly on the table, Jack hovered over Will's softly undulating frame. Will's eyes were closed, but the lids fluttered gently and his mouth hung lax, breathing deeply. Jack tried to control himself and he scissored his fingers slowly, taking the time to let Will adjust before adding a third finger.

After a time, Jack decided Will was ready to proceed to more satisfying endeavors. Jack knelt between Will's thighs and coated his own groin with oil. He continued to use his hand on Will, to distract him. Leaning down, Jack kissed him on the neck and slid forward, removing his hand. Will felt Jack's hardness press against him and he shuddered. Jack pushed forward, meeting minimal resistance. Will visibly tried to calm himself and grunted with the effort of allowing Jack entrance.

Their progress was slow and Jack had to remind Will to breathe more than once, but he turned Will's attention frequently, rubbing him with his hands and kissing him. This did at least for much as Will as it did for Jack, who was frequently overwhelmed by the heat and pressure of Will's body. Jack pushed slowly and steadily forward for what seemed like forever until their torsos were joined. When Will realized Jack could push no further, he let his head fall back and he heaved a sigh, relaxing himself.

"That's it, luv," Jack said. "It will get easier."

"Don't talk," Will breathed. "I want you. I want more of you."

Jack didn't need any more convincing. He groaned with arousal and pulled backward, preparing to thrust. Jack shifted his weight and adjusted his hips, searching for the same spot he stroked in Will earlier with his finger. He knew he found it when Will gasped and latched his hands tightly to Jack's shoulders.

Jack considered this an encouragement and he pulled back, thrusting again at the same angle. He repeated the motion until Will was panting with exertion. When he was certain that Will was adequately fervent, he pushed harder, using a hand on Will's hip for leverage. Then, realizing he was quite close to Will's arousal, he ran his hand down. At Jack's unexpected touch, Will breathed in sharply. His exhale was shaky and Jack could feel in the muscles of Will's body that he was close to finish.

"Ah, Jack..." Will began. "Jack, you feel... Ah, you feel..."

"Gods, Will, say it!" Jack spat.

"More, Jack," came the breathy reply. "You feel so good."

"Aye, Will," Jack half shouted.

Jack leaned against Will's chest and thrust with all his force. Will wrapped his arms around Jack's back, pulling him close and entwining their legs. He flung back his head and moaned Jack's name, arching into every thrust. Then, Jack felt the spasms of Will's body as he sped toward climax. The pressure around Jack's hardness increased unbearably as Will rocked back and forth almost violently. Finally, Jack cried out his completion as Will spilled over his hand. Jack slowed to a stop and kissed Will tenderly before untangling their limbs.

Getting up from the table, Jack carelessly handed Will a piece of someone's clothing from the floor to clean himself with. He helped Will off the table and sent him to bed, saying he would need the rest for his engagement with the Commodore. Will rubbed his tailbone and did as he was told, leaving Jack alone with his thoughts. Little did he know, Jack would be spending the rest of the evening contemplating his course of action in acquiring Will's precious compass without the unpleasantry of sending his innocent mate into the hands of a decidedly not-so-innocent Commodore.