Home
 

Tutelage


by Justawench


Pairing: J/W
Rating: NC-17
Disclaimer: These characters do not belong to me no matter how much I might wish it.
Originally Posted: 10/16/07
Note: I'm plunging into the deep end here. I make no claims to be a professional writer, but I hope you enjoy it anyway. A multitude of thanks to naotalba for her patient beta.
Summary:Will seeks Jack out prior to his wedding, and Jack is of a mind that he needs some instruction. Really just a PWP.



The Faithful Bride was just as Will remembered it. Trying to look as if he belonged there, he worked his way around the common-room, searching for a familiar face. Due to the low light and smoky haze, he recognized the expansive gestures before he could see the sartorial details of Captain Jack Sparrow. Now, so close to his goal, he was suddenly seized by a fear that Jack would laugh at him or turn him away. He was still hovering a bit off to Jack's left when Jack glanced past one of his female companions and spotted Will.

"Well, if it isn't Will Turner!" he grinned.

His fears allayed, Will grinned in return and took the facing bench Jack had indicated with a shove of his boot. The women flanking Jack smiled sweetly at Will in greeting, but there was a predatory look in their eyes.

"I knew the governor would commute your sentence; Elizabeth has him wrapped around her little finger. So, just banishment, then?"

"Not at all, Jack. Elizabeth and I are to be married the week after Whitsunday."

"That calls for a celebration, then—drinks all around!" Jack fair shouted the last bit as he waved his mug, sloshing dark rum onto the table. He leaned forward to speak in over-loud confidence. "I know you didn't travel to this den of iniquity just to share that bit of information with your one-time acquaintance Jack Sparrow. What business brings you here?"

Will shifted nervously in his seat. "I was hoping I could join your crew for a bit. I'd like to set aside enough money to buy Mr. Brown out of the smithy."

"This is certainly a surprise, considering your recently, fervently-held beliefs. I suppose you are your father's son, after all." His eyes roamed over Will as he seemed to consider the matter.

"Could always use a good sword-arm. Welcome to the crew!" Jack extended his hand and they shook on it. Jack cast a meaningful glance at his two companions and continued, "That'll have to do for now; I don't have any intentions of returning to the Pearl tonight to retrieve the Articles." Will couldn't restrain his flush as he caught Jack's hint, and he awkwardly stood.

"I suppose I'll leave you to your evening's... entertainments, Captain."

"Nonsense, we haven't even toasted your upcoming vows!" Jack objected, as a serving girl placed a timely tray of mugs on the table.


*****


Several rounds and wild stories later, Jack observed: "William, your pretty blushes seem to indicate that you have little experience with the charms of a female. Was I correct in my initial assessment that you lack the proper equipment?" He looked pointedly at Will's crotch and the women tittered.

Flushing now in anger, Will replied, tightlipped, "No, Captain, everything is in working order."

"Then there's only one other reason—Will, never say you haven't lain with a woman."

Will found himself closely studying the slip pattern on his mug.

"Dear William, this situation must be remedied immediately! I cannot, in all good conscience, send you to your marriage-bed an inexperienced fumbler. Come, you can join me in my room upstairs and one of these fine ladies will teach you the necessary skills straight away!" Jack offered earnestly.

"Jack, I haven't waited all these years for Elizabeth's hand just to sully myself when my goal is finally within my grasp! Apologies, Miss." Will dipped his head at the proffered whore.

Jack sniffed, "Well, it will be a sad state of affairs when you find yourself joining the ranks of the Cuckolds, as is so common these days." This thought inspired Jack to break into a drunken and slightly off-key song:

"There's neither Lord, nor Gentleman, Citizen, or Clown,
That liveth in the City, or the Country Town,
But may carry horns about them, tho' they them never blow,
For Gallants are like other Men, Cuckolds all a-row..."

To preclude the aural assault of other verses, Will scoffed, "I assume this is a subject you'd know much about? No doubt you've cuckolded many a man in your travels. However, I am secure in the fact that Elizabeth loves me and would never—"

"Aye, you say that now, but she has not experienced the disappointment of less-than-fulfilling sport. The skills you use to please yourself are akin to those needed to play a pennywhistle; you'll find Elizabeth is more of a spinnet."

"Well, even if that's true—"

"It is," Jack interrupted.

—I'm sure it's a skill that can be developed in the future. With Elizabeth." Will frowned as he reasoned out his argument; his mind felt hazy.

"And how do you propose to learn this skill if you turn down the lesson I've so generously offered? You didn't become a blacksmith without a... helping hand, as it were."

Will snorted into his mug and nearly choked before he was able to reply, "Are you offering to take me on as an apprentice to learn your trade?"

Jack grinned back, "Aye, and I'll not release you from your obligation until you're a Journeyman of Swiving!" The girls at Jack's side found this especially funny, and they all dissolved into a fit of hysteria for a few moments.

Wiping the tears from his eyes, Jack turned serious. "I feel badly that you've not had a father to teach you these things, and that could even be construed by some to be partly my fault. Why don't you let me make it up to you, eh?"

Will was softening, but he still had objections. "Can these lessons not be explained? Surely they don't have to be performed. I'm sorry, Jack, but I refuse to sleep with another woman."

Jack sighed with the air of one much put-upon, then pronounced, "Aye. Why don't we retire someplace more private; no need to embarrass you publicly. Darlings, I regret to inform you that you'll have to find another cull for the evening, but maybe this will take the sting out." He slipped each of the women a coin and they disappeared remarkably quickly. After a couple of tries, and disentangling his coat from some splinters on the rough bench, Jack managed to get to his feet and around to pull Will up. They paused for Jack to procure some liquid provisions and stumbled up the narrow stairway.


*****


Will seems grateful both to have Jack as his confidant and to be away from the rowdy crowd downstairs. With an untrusting glare at the rickety chair, he propped himself against the headboard. Jack removed his coat, hat and baldric and draped himself bonelessly across the foot of the bed with a crunch of straw.

Jack was already aroused thinking of the things he could teach the boy, and he had to surreptitiously rearrange himself.

"I suppose we should start with anatomy. Are you familiar, dear William, with the primary differences between the male and the female of the species? You've surely seen animals mating—the principles are the same." Will's face turned red at the image this apparently conjured.

"Of course!" he blurted. "But if that's all that's involved in pleasuring a woman, there wouldn't be any of those cuckolds you mentioned."

Jack rolled his eyes. "I didn't say that was all that was involved. I'm just trying to get you up to speed."

"Oh."

"And anyway, there would still be cuckolding; not every man is endowed enough to pleasure anyone." Seeing an opportunity, he added, "Hopefully you are not one of those men who are lacking, eh?"

"I'm not a eunuch!" Will shouted.

Jack held up his hands placatingly . "Didn't say you were! I was just asking if the equipment was adequate, 'cause if it's not, you'll need to learn other... skills."

"Oh. Um, I don't know. How can I tell?"

Schooling his features into nonchalance, Jack innocently offered, "I could take a look." At the boy's frown, he added, "As a friend, of course." Will considered this for a moment, and apparently the rum he had consumed made this seem like a reasonable offer. He unbuttoned his breeches and lowered the flap to reveal a half-hard prick of impressive size, the sight of which sent another rush of blood to Jack's.

Clearing his throat, Jack continued, "That's all well and good, but I'm going to need to see it full-size to make my determination." This was met with an agape stare from Will. "You do know how to get it hard? I should hope a boy of your age has had the urge to relieve himself, otherwise, we've got a bigger problem." Still the recipient of a horrified look, Jack changed tactics. "William, there's nothing to be ashamed of. It's completely natural. I'm a well-practiced onanist, myself!" He flashed gold and ivory as Will jerked the cloth back over his bits and put his head in his hands.

"Yes, Jack, I know what you're talking about, but I am not going to demonstrate it for you!" came the muffled reply.

Jack frowned, then replied brightly, "I know what's making you uncomfortable." After a moment, rhythmic rustling and swaying of the bed caused Will to raise his head.

"Good God, Jack!" Will exclaimed. Jack's hand was gliding smoothly up and down the shaft of his prick, the foreskin revealing and obscuring the glistening head. Will quickly clapped his hands back over his eyes.

"Calm down, Will. It's just a friendly frig between mates—no cause to get bent out of shape. I thought you'd spent some time shipboard in your youth? Surely you don't expect to discuss this kind of subject and us sit around chaste as nuns in a nunnery? It gets a fellow's blood fired up, it does." Jack punctuated that with a thrust of the rum bottle into Will's ribs, causing him to drop his hands and take it in surprise. Obviously needing some Dutch courage, Will took a deep swig, but kept his eyes averted.

With Jack sitting still beside him, Will risked another glance in his direction. "No doubt I'll curse myself for a fool tomorrow, but let's get this over with." He sighed his concession. "Race you? First one fully hard gets the rest of the rum."

The smile that was forming on Jack's face abruptly crumbled. Oblivious, Will set to work and had himself at full hardness in a short time. Noticing the still form next to him, he inquired, "Jack?"

Jack's jaw was clenched and he was about to stare a hole though the floorboard. Finally, nostrils flaring, he managed to part his teeth enough to utter, "It. Is. Hard." It seemed the awkwardness of the situation conspired with the alcohol to cause Will to fall backwards laughing. Now it was Jack's turn to jerk his pants up.

"It's not funny, you virginal bastard," he griped as he turned his back on the shaking form.

"I know!" Will cackled.

"No, I'm serious. Just because you're extraordinarily endowed doesn't mean my tackle is small."

"I'm sorry." Will became contrite upon seeing the slump of Jack's shoulders, but he was exuding a newfound confidence. Jack's desire to continue pouting was trumped by his desire to lay eyes on the boy's "endowment" again. He relented, and subtly scooted closer to Will as he turned back to him.

"Back to your lessons."

"What? I thought we'd established that my 'equipment' was sufficient?"

"Could you make a horseshoe just because someone handed you a hammer, some tongs and an anvil?"

"Well, I'd need some metal. And I'd hope no one ever handed me an anvil—"

"Shut it. What I mean is, you need the tools and the knowledge."

"Teach on, great professor." Will leaned against the headboard still exposed, looking more relaxed, or at least more inebriated.

"That's "Master" to you, Apprentice." Jack retorted.


*****


After much vivid and graphic description, only occasionally interrupted by a question from his student, Jack noticed Will's earnest expression was becoming strained. For his part, Jack had been slowly stroking himself throughout the lesson, but Will had refrained. Judging from the weeping tip, he was painfully hard. While he had talked, Jack had positioned himself at Will's side and slung a friendly arm around his shoulder. He could feel the boy's rapid breathing.

"You know, a strange hand feels very different than one's own. You should acquaint yourself with this sensation to ensure you don't fire prematurely and put an early end to your wedding night."

Will groaned, "Jack, for the last time, I am not going to retain the services of a whore."

"I wasn't suggesting that. Why don't you use my hand? Put yours over it and guide it like your own."

"Are you being serious?" Will sounded skeptical, but was that a note of hope Jack detected?

"As can be. Here, I'll close my eyes if it makes you feel better." Jack cupped his hand around the boy's prick, but didn't touch. He itched to, though, and fancied he could feel the heat radiating from it. Peeking through one cracked eye, he watched Will's hand hover indecisively, then close both their fingers around his hot length.

"Ah!" Will's exclamation covered Jack's sharp intake of air. It was all Jack could do to leave his arm lax for Will to guide; he wanted to run his hand up and down the pulsing shaft. Both hands, actually, for they would have fit. He ached to touch himself similarly, but he needed to keep his free hand still lest the other join its rhythm.

After some slow, awkward strokes, Jack felt Will's fingers entwine comfortably with his. As Jack reveled in finally touching this carefully guarded treasure, he felt Will speed up and heard Will's breath coming in quick gasps. After a few more seconds, Jack tensed his arm and stilled the movement, earning him a strangled sound.

"What..." was all Will managed.

"The point of the lesson was to teach you some control," Jack chided, thrilling inwardly that he still had his hand on the prize. The lad's eyes were dark and his lips looked wet and swollen as if he'd been biting them. "Lean back and close your eyes, and I'll give you the advanced lesson." So worked up was the poor boy that he cooperated without even questioning Jack this time.

Jack had to put his hand back on his own straining prick as he leaned forward and enveloped Will's in the wet heat of his mouth.

"Jesus, Jack!" The boy bucked uncontrollably, forcing Jack to pin his hips with his supporting arm. Jack's sensitive lips brushed against silky skin and he tested the firmness gently with his teeth. After a full exploration of the weight, scent and texture, he fell into a steady rhythm—up and down, in and out. He didn't get to enjoy suckling on the swollen cock for long; he sensed Will was approaching his climax, so he pulled off with a dramatic slurp.

"Gahhh!" Will cried, his hips uselessly thrusting his prick into the air. The lad was all thrashing, straining muscle, and Jack felt assured that his assessment of the boy was correct: his self-inflicted deprivation had left him with a short fuse.

"Now comes the true test, if you're up for it." Will was stroking himself desperately and unashamedly, and Jack batted his hands away, lest the boy spoil their fun. "Demonstrate what you've learned."

With a practiced motion, Jack's clever fingers brought forth a bottle of oil from a hidden pocket in his waistcoat. In seconds, he was working two fingers inside himself and biting back a moan. Realization dawned on the lad's face, and Jack was surprised by the fierce manner in which the boy grabbed him and spun him around. The force aroused Jack; it had been longer than he'd care to admit since he'd had anything other than manufactured passion, bought and paid for.

Jack felt the blunt head of Will's cock pressing against him. With a sudden thrust, the head pushed inside, nearly splitting Jack in twain. At least, that's how it felt.

"Ah! Hold up there, boy!" Jack gasped. Twisting his head afforded one eye a view of Will's distressed expression.

"Sorry, Jack, sorry," he sputtered.

Feeling Will start to pull away, Jack hurriedly said, "No, it's fine, I just need a moment to adjust. Ol' Jack hasn't been breached by such an impressive cockstand in quite a while." He added under his breath, "Maybe never."

After a few painful seconds, Jack felt himself relax and he began to rock his hips a little, taking Will bit by bit. They groaned in unison until he was finally pressed against Will's hips. He told the tense figure, "All right."

Jack was surprised again by the speed at which Will reacted to this cue. He was pounding into Jack with the wild abandon of a rutting animal, his girth dragging across Jack's pleasure center with every thrust. Will grunted with exertion as Jack's babbling curses rose in crescendo. All pretense of education was thoroughly forgotten.

"Oh, fuck. Oh, Christ—harder!" Jack was overwhelmed by the furious pace. "Bloody fucking hell youbuggeringBASTARD!" he heard himself shout, as his untouched cock pumped hot seed across the sheet. The sudden clenching of internal muscles overcame the dampening alcohol and Will spilled himself in Jack's sheath. Easing his sensitive organ out, Will collapsed on the bed.

Jack's arms gave out, and he caught his breath with his cheek pressed into the bed and his bare arse in the air. Eventually, he stirred and frowned at the wet spot below him. He gingerly got out of bed to retrieve a rag, feeling liquid dripping down the inside of his thighs. By the time he and the bed were fit for slumber, Will was asleep.

Jack laid beside the still form. No doubt they'd have other encounters before Will took his leave of the Pearl, but eventually he'd return to the girl's arms, and Jack would be returned to paying for his sport with partners who would forget him by their next customer. It was a good thing he was Captain Jack Sparrow or he might be jealous of an underdeveloped governor's daughter. He fell asleep secure in the knowledge he'd never be jealous of some undeserving, flighty slip of a girl.



  Leave a Comment


Disclaimer: All characters from the Pirates of the Caribbean universe are the property of Disney et al, and the actors who portrayed them. Neither the authors and artists hosted on this website nor the maintainers profit from the content of this site.
All content is copyrighted by its creator.