The Wager

Title: The Wager
Author: Hellborne (the_ferret_mom@yahoo.com)
Age Rating: 18+

Disclaimer: Characters, if you saw them in the movie, not mine. See the Mouse. Story, mine, but I make no money. He does, but not on this.

Typing convention: / is used for thoughts. * - * - * is used for scene changes and passages of time.

Summary: Will and Jack make a interesting bet...Who wins?

Warnings: M/M

Betas: The two greatest BetaGoddesses in the world, Pendragginink and Littlebird! You're both truly magnificent, and I wouldn't be able to write half as well without you!

Admin Note: Hellborne wrote this before she passed away. It is posted now for you enjoyment. I'm sure she can read reviews where ever she is.


* - * - *

Will continued licking Jack's manhood like a lollypop: dragging his tongue
languorously up and down the vein, lapping up Jack's precum, and sucking on
Jack's balls one by one, humming; tickling them with his tongue.

Jack lay on his back, propped on his elbows in order to watch his lover
work, but presently, the pleasure was just too much for him. His eyes closed and his
head thrown back, mouth open with desire. His nipples were as maddeningly hard as his
member, his undulating hips moving of their own accord, yet Will kept him at bay, moving,
working his lover at his own, slow rate despite the older man's futile attempts to speed
him up.

The boy had been worshipping his length in that agonizing way for the longest;
many times letting Jack get oh, so close, yet wouldn't allow him to complete. Jack
TRIED to chastise the boy, his tormentor...he really DID...but every time there was a
lull and he opened his mouth to complain, Will would start in again, driving him mad with
passion, and his mind would be too far gone to form words quickly enough.

After bedeviling the pirate by alternately sucking and blowing cool air on
his member for what seemed like hours, the younger man suddenly moved his head off Jack's
now suddenly dry, shuddering shaft and licked his lips. He grinned as Jack recovered
enough to look daggers at him.

"Jack, I want this to LAST: to be memorable, and now it will."

He pulled out the small vial of sweet oil they kept for their
lovemaking and coated Jack's aching member, then climbed to a position above the panting pirate captain's squirming hips and aimed Jack's straining manhood at his opening. Ignoring the suffering man's pleas, he lowered himself unbearably slowly, one torturous inch at a time, finally burying the organ within his body to the hilt.

Then, he began to move.

Will slowly raised himself up until only the very tip remained at the
opening of his heat, then lowered himself anew, slowly...so painfully slowly...until he was filled once again.

Jack tried to thrust his hips, but Will's legs held them down, motionless. Jack begged.
He pleaded. He threatened the boy's life -- twice. But Will kept that excruciatingly slow
pace, building a pleasure so intense that Jack was afraid he would burst.

Then, he was more afraid that he wouldn't.

Finally, the dam broke: furious with lust, Jack's beleaguered body took
over: almost bucking Will off as it struggled for relief.

But he was robbed.

Will had stolen his completion by teasing him...forcing him to dribble
out his essence till until now, he was dry. It would take many long minutes to create
enough for release. The pain was excruciatingly exquisite: achingly wonderful. Jack
wanted to kill the whelp. He vowed he'd get even...after he came!

But in the meantime, Will kept driving him wild: the relentless pleasure
built higher and higher, his over sensitized balls, aching to give him release. But there
was no release. He found that as fast as his body built up his essence, it would
dribble out just as fast, thanks to the ministrations of Will's tantalizing tongue, still denyinghim climax.

"WILL PLEASE!!!"

Will smiled gently and stopped, Jack's manhood half-immersed in his heat. "Yes, Jack?
You want something? Perhaps this?" He slowly lowered himself an inch, leaving
the old pirate in blessed agony.

"NO!!! HELP ME!!!" Jack writhed.

Will smirked. "Oh! HELP you! Perhaps like this?" He started bucking wildly
on his lover, taking his own member in hand and fisting himself, moving to the same delicious rhythm as his hips. It didn't take long before he came, shooting his cum high onto Jack's chest, neck, and even face.

Jack screamed, keening as the boy moved. Finally, blessedly, Will
stopped. With tears in his eyes from the torture he'd gone through, Jack collapsed, freeing his arms. He grabbed Will and threw him on to his side. Out of breath but far from
satisfied, Jack rolled on top of his lover.

"Love, you are so going to pay dearly for this. You can't drain a man thus,
deny him completely and expect to live through it unscathed."

Will kissed Jack on the nose and rolled them both on their sides. "And just how shall you make me pay for it, hmmm?"

Jack chuckled softly, yawning. "I'll tell you in the morning, whelp. But
believe me, young William, you shall not enjoy it." He rolled over, murmured contentedly, "You are in SO much trouble when I wake up," and went to sleep.

Will cuddled against Jack's back and drifted off to sleep wondering what
Jack could possibly do to him that he wouldn't enjoy.

* - * - *

Will woke up alone.

Jack had apparently gotten up before him and not awakened him. He
dressed quickly, rushed out of the cabin and looked towards at the helm. The wheel had
been tied off; no one was there. He looked around and saw that the ship was anchored in a
small, natural harbor; a longboat was pulled up on the beach. He could see Jack on
shore, relaxing against a tree, drinking from a bottle: no doubt rum.

At that moment, Jack saw Will and waved enthusiastically, motioning for him
to come ashore. Will found Gibbs and had him help lower a boat, then climbed down,
cast off, and rowed to the beach.

Jack helped him drag the boat up onto the sand. "Beautiful little beach,
don't you think, love?"

Will took the bottle from Jack and risked a small swig. It was a flavored
ale, which made the younger man smile in surprise. "Where are we, Jack? It's gorgeous, but
I've never seen this island."

Jack grinned, taking back the bottle and corking it. "Aye, ye have,
William. This here is Jamaica, and Port Royal is no farther than sixteen miles yonder over those hills." He pointed. "And since you were OH so NICE to me on our way here, I have a little job for ye. I've made a deal with Captain Tom Davidge, and YOU are going to go do our part. You see, he and I made a little wager that he could get the Duchess of Bradbury's wedding ring from her finger and bring it to the Faithful Bride in thirty days. He's got five days to go. In return, I'm to bring him the lovely Miss Swann's corset and petticoats to the same place when we meet there. Now I KNOW the young Miss Swann would rather see me at the end of a rope than to allow me to remove anything from her person. YOU, on the other hand, could woo yon fair maiden and get those little pieces of frilly
cloth FOR me."

Will blanched. "Me? Elizabeth's underclothes? You're a pirate! Why can't
you just break into her room and steal them?"

Jack grinned. "But that just won't do, lad. I can't think of anyone more
qualified to take them right off her body, and, as a matter of fact, that's the wager. He
gets the ring right off the Duchess' finger, and we get the underclothes right off the
Governor's daughter. So I'd hop to it, if I were you. It's a full sixteen mile walk, and
I need you back by tomorrow night."

Will harrumphed. "Very well, but I want something if I can do it."

The pirate captain raised an eyebrow. "Aye? And what would you like? An
extra share of the next haul? I can arrange that."

"No, Jack. I don't want money for it. If I can manage to get Elizabeth's
corset and petticoats and deliver them to you, you'll WEAR them until we get to the
Faithful Bride."

Jack looked shocked. "You'd LIKE that, wouldn't you, whelp? You're insane!
Me? Wear a woman's undergarments?"

Will giggled. "Yes, yes, I would. For the entire time it takes to get
to Tortuga."

"And if you can't get them, you'll wear a sailcloth breechclout and
leather collar...be my slave until we get there. If we fail, I have to give the blighter m' boots. If he fails to do his part, he has to give me his greatcoat. You've seen the one, 't is the grandest coat I've seen, and mine is getting a bit threadbare. And if I have to give that son of a whore m'bloody boots, YOU are going t' find me a suitable replacement, even if ye have to MAKE THEM, savvy? So I'll expect you to get me the clothing in question, young Mr. Turner."

"And you'll wear the underclothes until we get there."

"Aye, and it'll be worth it, t' keep m' boots."

Will grinned. "I'll get them."

Jack grinned wickedly. "Oh. I forgot to mention. There's a high-toned and
fancy ball at the Governor's mansion tonight." He picked up a rather large pack. "This is for you to wear so that you'll fit in with the nobs. Wouldn't want you to get arrested and
hanged over a little bit o' fluff, now would we?"

"No...what is it?"

"Just a little something to wear so that you'll blend right in. Now off
you go." Jack shooed him off in the right direction.

Will picked up the bulky pack, which after all, turned out to be quite
light and set off toward Port Royal.

When Will arrived in town, he found everyone in a tizzy getting ready for
that evening's Halloween ball. He rented a room for the night and got himself
settled in, then opened unpacked the pack and grimaced in dismay.

/So, that's what was in the pack there! At least I'll be able to talk
to Elizabeth without being recognized./

* - * - *

"The Bird of Paradise!"

Will thought that he would die of embarrassment when he'd unwrapped the
bundle that Jack had given him, but now he felt that he'd be more embarrassed in a
proper dress suit. There were exotic birds everywhere! Live birds, stuffed birds, and
everyone was wearing feathers. All in all, Will felt quite comfortable in his elaborate plumage.

Governor Swann sported a very regal-looking ensemble suit with an
incredible peacock feather periwig. It was only by recognizing the sword at his side that
Will knew the large seahawk with the drink in his hand was Commodore Norrington.

Then he saw Elizabeth. Breathtakingly beautiful in a feathered blue gown
and headdress, she stood next to her fiancé, the "Blue Bird of Happiness" to his
dour hawk. Dour wasn't the half of it: upon closer inspection, the hawk's beak had a
small bird in it-- a sparrow.

/Wishful thinking, Commodore!/ Will chuckled to himself as he made his way
over to the couple. Disguising his voice as much as he could, he asked Elizabeth to
dance. Once on the dance floor, he told her how beautiful she was.

"I beg your pardon, sir, but I am engaged, and I doubt my fiancé would
look kindly on a stranger taking the liberty of making advances to his betrothed."

Will laughed. "Elizabeth, I know you are engaged, and I am not making
advances. And as to the Commodore, I don't doubt me he would be very happy to see
me...bleaching in the sun out at Deadman's Cay. It's Will, Elizabeth. Will Turner."

Elizabeth stared. She hadn't seen Will since he ran off with Jack Sparrow
the night before they were to be wed. "Will? You scoundrel! I've missed you so! When I
heard you left with Jack, I was positively furious! I mean...how could you do such a
thing without even a word?!"

Will's shoulders drooped. "I'm sorry, Elizabeth. I truly am. But Jack
didn't give me a choice in the matter. He slipped laudanum into my dinner, had me trussed like a grouse and carried to the Pearl then set sail. It took me a full six long months to
even consider THINKING about forgiving him."

"But it's been two years! Why didn't you return before now? I had given you
up! James and I are to be married tomorrow!"

"At first, Jack kept me in the brig whenever we were docked, but after a
while I got used to being aboard. Jack called it 'my blood getting the best of me'. And he
kept bringing me things: new clothes, jewelry, even a gold timepiece--French even.
Later, he started making advances at me. That was when I realized that all the gifts were
his way of 'courting' me. I resisted for a long while: several months, but, well -- just
six months ago, I finally gave in to him, and we've been together ever since. I'm first mate on the Pearl now."

Elizabeth was careful not to grin at Will puffing out his chest in manly pride.

"Then why are you here, now?"

"I need something from you in order to really humiliate Jack."

Immediately, Elizabeth wanted in on the deal. "Oh? How do you plan on
accomplishing that?"

Will grinned wide enough that his mask moved. "Elizabeth, I need your
corset and petticoats. If I can get those, Jack will have to wear them all the way to the
Faithful Bride tavern, and that's dead center in the town square in Tortuga."

The bluebird giggled. "Now THAT I really MUST see! And James as well."

"I'm afraid the only way to see that is if you go to Tortuga. I doubt your
fiancé will want to go there."

"To see Jack Sparrow in corset and petticoats? You must be joking. Of
course, we'll be there!"

* - * - *

"I am NOT coming out, William! Not until we dock in Tortuga!"

"Jack, I won fair and square! Now you unlock that door at once!"

"The deal was I'd WEAR them, William, NOT that I'd come out of m' cabin
before we arrive! And There is NO WAY in Heaven or Hell that I'm leaving this cabin! Are
you sure she was wearing these?"

"Yes, Jack. She was wearing those in particular. You can always ask her
yourself. So, if you're not coming out, at least unlock the door and let me in!"

*Click*

Will slowly opened the cabin door, peered in, and started giggling
uncontrollably. He quickly entered the cabin as an eye-rolling Anamaria slipped out, closing the door behind her.

There, in the middle of the room, was Captain Jack Sparrow. The corset was
an incredible confection: blue, with a feathered bust line of fluffy white
maribou. It was heavily boned and tightly laced, cinching his waist to wasp-like proportions. The wide petticoats sported a full seven hoops and were deeply ruffled, frothy with lace. Anamaria had shaved his face clean and apparently ransacked the hold to find sundry toilet articles including a very ornate, lady's wig. The kohl around his eyes had blossomed into the elaborate makeup of a grand lady: cheeks rouged to perfection, lips pouted and quite red. A black beauty patch highlighted the curve of his cheekbone. A diamond choker, clocked silk stockings, black velvet garters and blue satin shoes with high silver heels completed the ensemble.

"Not one word, whelp." Jack somehow looked less dangerous as a woman. And a
young lady at that! The lack of beard and the makeup made him look half his
age.

Will goggled, then forced his mouth closed and smiled pleasantly. "I wasn't
going to laugh, Jack. I was going to say you look beautiful."

Jack frowned. "That wasn't quite what I was hoping for, William."

"Well, I think you're beautiful: much prettier than Elizabeth. You thought
you'd look ridiculous, didn't you?"

"The thought HAD crossed my mind."

Will stepped forward and took the somewhat disgruntled pirate in his arms.
"You do NOT look ridiculous. You look beautiful. Ana will find a suitable dress in the
hold, and you, Captain Sparrow, will be the most beautiful lady in all of Tortuga."

Jack broke away, falling off the high heeled shoes and stumbling about
until he caught himself on the huge bed. "I'll be the closest thing to a lady IN
Tortuga! But I'm NOT a woman! And if Scarlet or Giselle see me like this, they'll immediately turn me into a eunuch...like YOU!"

Will moved in and took Jack's hand, bringing it to his own
crotch. "Does THIS feel like the gaff rig and tackle of a eunuch?"

Jack cocked his head with a sly smile. Will thought it was VERY fetching.
So did his manhood.

Jack smirked. "I'm not sure. I suppose if you merely got snipped, it might
APPEAR that you still have use of your goods."

Will had had enough. He planted his feet akimbo, hands on his hips. "Can't
tell, can you? Nothing for it then, I'll have to prove to you once and for all -- I'm
no eunuch!"

He shoved Jack back onto the bed, lifted Jack's legs over his shoulders, hiking
up the petticoats past the pirate's hips; he tossed the hoops over Jack's head,
exposing his manhood. He quickly unbuttoned his own breeches, letting them fall to his
ankles, took his rock hard member in hand, and without preparation or warning, but not
hurtfully, plunged hard and fast to the hilt into Jack's entrance.

On the first thrust, Jack screeched in protest, but then Will took hold of
the older man's organ and began fisting him in time with his thrusts; Jack moaned his
pleasure as his young lover pounded into him.

Will shifted his angle; Jack's pleasure intensified to the point that he
began babbling unintelligibly, his hips moving wildly in time to Will's thrusts. Will grinned evilly and thrust faster, bringing himself very close to completion. He sensed Jack was ready to cum, so he stopped and pinched the pirate's cock firmly to stop him. As Jack gave him a deadly stare and warning growl; Will plunged home again repeatedly, sending himself over the edge. He came hard, Jack's name on his lips.

As soon as Will finished cumming, he pulled out, his cock still dripping
slightly, and sank to his knees. "I love you, Jack Sparrow, and you are the most beautiful
person, man, woman, or sea creature in the ENTIRE Caribbean, no, in the entire WORLD." He
dipped his head, sucking Jack's entire manhood into his mouth and down his throat, nearly
cumming again at Jack's sudden gasp of delight.

As the boy bobbed his head up and down, Jack felt his tongue everywhere.
The onslaught was relentless. A few short minutes and Jack screamed his climax, the
creamy fluid shooting down the ex-blacksmith's throat, but the talented tonguing STILL
went on!

With the hooped petticoats up over his head, Jack couldn't see what Will
was doing, but he could feel himself building fast toward another roaring climax.

"Love, please! 's too much all at once for an old man! I give up, William!
You win! You are young! You are virile! You are myyy--ieeeee!!!" Jack came hard again, and
Will sucked him dry, savoring his taste on his tongue. Finally, after Jack had floated
down from his heights and lay dazed and twitching on the bed, Will lifted the flummoxed
pirate's legs yet again, positioning himself at Jack's entrance. Using only the cum from his previous climax, Will pushed in, using short, quick thrusts to bring himself quickly
over the edge once more. Fast.

When he finished, Will pulled out of Jack's heat and cleaned them both up,
slipping his lover out of the petticoats and corset, setting them carefully aside so as
not to crush the hoops and feathers. He repositioned the now sated and very sleepy Jack
onto the bed, still tricked out as a lady in make-up, wig and stockings. Then he kicked
off his own boots and breeches, and lay down next to him, cuddling in as best he could
without crushing the pirate's elaborate coiffure. Jack sighed happily, quite
contented, snoring softly into the pillow. Will was asleep in mere moments, as well, a gentle smile on his face.

* - * - *

"I guess he's not coming, gents! No doubt the coward couldn't even steal a
slip of a girl's corset and didn't want to face the consequences." The huge pirate
captain stood, setting the lovely wench on his lap down on the seat next to him and addressed the entire tavern. "Jack Sparrow is--"

"--Right here, you overstuffed Christmas goose!"

All eyes turned to the demure and previously soft-spoken beauty that
Captain Davidge had entertained on his lap all evening. Shocked expressions adorned
every face in the building except those belonging to the crew of the Pearl. Quiet muffled
explosions of sniggering ran through the room.

"I've got Elizabeth Swann's underthings, and I saw earlier that you do
indeed have the Duchess of Bradbury's wedding ring. So we're square, eh, Davidge?"

"And what proof do you have that the underthings belong to Elizabeth Swann?
And why are you WEARING them?"

Will stood. "That was due to a side-bet I won against Captain Sparrow. As
for the clothes being Elizabeth's, I--"

"--Because they are MY underclothes, Captain, and I AM Elizabeth Swann."
She turned to Jack. "And I'd like them back now that you're finished with them, Jack."

Jack stared. Elizabeth was wearing men's clothing much the same way
Anamaria did. She was clinging to a tall man next to her. Jack knew that face, even if it WAS attached to a rather scruffy and decidedly dirty man who was barely able to keep his
laughter in check. "Jamie, isn't it? Jamie wot I made such GOOD FRIENDS with in Port Royal
three years ago? Jamie wot worked in the stables shoveling manure? I see your situation has improved considerably! Jamie, it's so great to see you again, sweetheart!" Jack
sashayed over to Norrington and gave him a smacking kiss on the mouth, leaving a large lipstick mark, then nibbled his ear, whispering softly.

"You and Mrs. Commodore had better leave, RIGHT now, before one of these
sons of o'whores recognizes you. And if anyone has heard that dear Elizabeth married
YOU, the jig is up. Make your way out slowly with the missus, and skip off to your ship. My men will follow an'hang back t'make sure you're safe. Set sail immediately, and go EAST
around the island, NOT directly back to Port Royal. Then hightail it home. We'll return
dear Elizabeth's clothes at another time."

Norrington nodded ever so slightly.

Jack turned to Elizabeth. "Perhaps you and your man should leave. Your
father will be worried if you're gone for too long, and I don't want to be held to blame for your absence. And don't worry about your things, luv. We'll return them as soon as we can. That is, if we can sneak in without that mad dog Commodore `Noosance' Norrington catching us."

The entire tavern laughed. Elizabeth blushed furiously, but Norrington
started moving her toward the door. Two men slipped out a moment after they were gone,
followed closely by Will and Anamaria.

A small band of musicians started playing a quick chantey and Captain
Davidge grabbed a VERY surprised Jack and dragged him onto the dance floor.

"Jack Sparrow, I swear, you are the prettiest lass in Tortuga, and I
mean to keep ye!"

"But I have a ship to run, luv. I simply have no time t'be your whore." He
danced with Davidge, subtly moving the two of them toward the musicians. "Although it IS
tempting...you ARE one handsome mountain of a man."

They got very close to the musicians and Jack sneezed, Davidge letting go
of his hands for a moment as the pretty pirate captain doubled over from the force of
the sneeze. As he straightened up, Jack grabbed a fiddle from one of the musicians,
clobbered the giant man over the head, knocking him down, and then ran as fast as he could
in the high heeled satin slippers.

Jack barely made it to the door when his huge ex-dance partner roared, got
to his feat, and started for Jack. Jack lifted his hoops and petticoats and kicked the
shoes off one at a time, hitting Davidge square in the forehead, then took off running for
the Pearl, holding his skirts high.

After leaping over two familiar-looking bodies from the tavern, he galloped
up the gangplank of the Pearl, skirts falling as he ran. He tripped, and went tumbling
forward, flying arse over teakettle, landing in a heap on the deck. Pulling himself up,
Jack looked up at the helm. Will was already shouting orders, and the men were casting off in a hurry and in no time at all, they were underway.

The Pearl pulled out of the harbor, sails full of wind and the sweeps going
strong. Jack staggered into his cabin and began pulling the clothes off, finishing up with a face wash and reapplying his usual kohl.

When the pirate captain strode out of his cabin, once again in full pirate
glory, he was surprised to receive myriad whistles and catcalls. He glared at the
perpetrators, but then he heard the explanation news from Will at the helm. "Jack! Your wig!"

Jack laughed. "'s not a wig, whelp." He pulled the pins out of his hair,
and it fell straight and silky, no braids in attendance. "I just combed it out and put it
up all nice and proper." His hair flying free in the wind, he bounded up the steps to the
quarterdeck and took over the helm from Will.

"Jack, you still look very pretty...like a young lady trying to 'play
pirate'."

"Whelp, I may have t'take ye over my knee now, just for saying that."
Jack shrugged. "Truth to tell, in m' youth I was often mistaken for a lass. I've always been a bit on the slight side for a man. In fact, my boots are specially built t'add an extra two inches on the inside, so that no one notices how short I really am. I'll be re-braiding my hair tonight. I'll be back to my regular fetchin' self in a month or so, though I won't have m'beard braids for some time. Now, could you please find me m' scarf and hat?"

Will nodded and went to get the items, returning in only a couple minutes.

Jack put them on, sighing with contentment. He shouted orders to head north
at full speed, all the while making course changes to accommodate wind and current and
keeping a sharp eye for sails behind them. When he was sure they had left behind
any pursuers, he ordered the Pearl turned toward Port Royal.

* - * - *

Commodore Norrington brought the Lady Swan into Port Royal safely, and made
fast, helping Elizabeth off the yacht onto the dock. They made their way up the lane
to their house and went in.

Exhausted, Elizabeth made her way to their bedroom and gasped. There, on the
bed, were her hoops and petticoats, all laid out neatly. On top of the petticoats,
there was a note and a small package. The writing was Jack's frilly script.

"My dear Mrs. Commodore,

"Thank you for the use of your darling underthings. I must, however, keep
the corset as I have grown quite fond of it and Will especially thinks I look especially
adorable in it.

The little package is a poor trade, I'm sure -- just an old string of perfect
pearls we had lying around in the hold, but please accept it as a wedding present anyway.

I'm glad that you and your lovely new husband got away safely. Perhaps
the next time the Commodore and I meet, it can again be on pleasant terms, such as this
last time.

"Yours , most sincerely,
"Captain Jack Sparrow of the Black Pearl out of Tortuga"

P.S. I do hope he kisses you often and as pleasurably as he certainly did me.

Elizabeth smiled wistfully. /Yes, Jack. He does. MOST pleasurably./

* - * - *

End