A/N: Hello, my dear readers. As a way of explanation, I thought I might inform you now that I am not, in fact, on crack cocaine or any other mind-altering substances. I did, however, come up with the idea of writing a Supernatural-meets-Pirates-of-the-Caribbean-meets-the-Odyssey AU comedy fanfic, and this happens to be it.

Yeah, I don't know either. Maybe it's a chemical imbalance?

Anyhoo, basically, it's the characters we know and love plopped down in the Golden Age of Piracy and sent on an archetypical adventure-journey with some Greek gods thrown in. I could've just had Sam and Dean go through the Odyssey in America, but that would make way too much sense! And I do intend for this to be a screwball kind of adventure. I've been way too dark and serious lately and I wanted to write something that feels more like "It's A Terrible Life" than "What Is and Never Should Be," you know? Less angst, more stripey shirts and vampire bobbleheads. This first segment isn't that funny because I'm trying to set up a hell of a lot of stuff, but I promise it'll get sillier. Aaaaand of course, as with all good fics, the REAL appeal is DEAN AN' CASTIEL 4 EVAR NO - 5 EVAR BECUZ 5 IS MOAR THAN 4!1!

I should be banned from the English language.

Please review and let me know what you think - the more nice things you say, the more compelled I will feel to continue the story as fast as my pudgy little fingers can type! If you say terrible things, I will just cry and eat cookies and my fingers will get pudgier. AND, as a SPESHAL BONUS, anyone who reviews will get a one-time-only Imaginary Pirate Dean in the imaginary mail! As they say on the high seas, yo ho ho and a bottle of sexy, sexy manflesh.

And no, without further ado, the story!

P.S. I forgot to mention, this is in no way intended to be an accurate representation of pirating or sailing or any marine-related activities. This is the euphemistical fantasy version of all that. So please, if I have my characters hoist the mainjib to the sailbarge or whatever, don't worry about informing me of my nautical inaccuracies. I also am not even TRYING to make Sam and Dean sound piratical, so yeah. Thanks! I LOVE YOU ALL SO MUCH.

London, England

Lisa Braeden had met the love of her life, and his name was Dean Smith.

Dean was a handsome sailor, much better kept than the other ruffians who came to port in London. He parted his short hair to the side and had a reddish-brown beard that he kept cropped close to his ruddy face; he still had all his front teeth, and lively green eyes that danced and darted. Lisa was defenseless against his charms. A poor seamstress, she had seen many men come and go in her shop, and none of them could hold a candle to him. Her father had warned her about sailors, but Dean was different. Dean was honest.

He was only in London for a month, and when he had to set sail again Lisa wept bitterly. "Please," she begged, "take me with you!"

Dean tutted softly and held her close. "Women are bad luck aboard a ship," he reminded her. "Besides, I won't be long. I should be back in a few months."

"Return to me," she said, taking his hand in hers. "Promise me you'll return."

He kissed her hand, and smiled. "I promise. And when I do…" He kissed it again, but slower, more deliberately. "I'll make an honest woman out of you."

And Lisa believed him, heart and soul.

….

A week after he lost his wife to scarlet fever, Dr. Samuel Wesson apprehended a burglar in his bedroom.

It was just after midnight. He was lying awake, staring at the ceiling, trying and failing to forget how large and empty the bed was, thinking of her pale hand in her coffin and how cold her forehead felt when he bent down and pressed his lips to her, when he heard a noise.

A rustling, at the window. The distinctive metallic click of a blade sliding under the latch.

Dr. Wesson sat up in his bed and quietly slid off into a crouch.

Moonlight shone through the gap between the heavy curtains and outlined the silhouette of a man, just as the figure worked the latch open and slowly swung the window pane outward, bringing one foot over the sill and stepping into the room.

Braced for an oncoming knife, Dr. Wesson lunged.

The intruder put up a good fight, though for some reason he didn't use his weapon. He stank of cheap rum and mildew and salt. He sparred with Dr. Wesson and jabbed in all the right places, too right, too familiar, and by the time he had the good doctor winded and pinned to the floor, Sam gasped aloud, "Dean?"

Dean grinned, a glint of white teeth in the darkness. "Sammy." He pressed the cold metal of his knife against Sam's neck. "Just like old times, huh?"

Sam pushed him off and sat up, rubbing the spot where the back of his head had smacked the freezing hardwood floor. "What are you doing here?" he hissed. "You could be hanged!"

Dean stood up. "So could you." He offered his hand.

"No I couldn't," Sam retorted, pushing himself up, ignoring the hand. "I'm legitimate now."

Dean smirked. Sam couldn't see it, but he knew he was smirking. "I know. Doctor Wesson. A pillar of the community."

Sam sat down on the bed, suddenly feeling the weight of his bones and the entire night's fatigue, and he asked wearily, "What do you want, Dean?"

Dean paused. "I'm sorry about Jessica. I heard what happened."

Sam clasped his hands. "That's not why you came."

"It's part of why I came." Dean stepped closer. Now that his eyes had adjusted, Sam could see his face better, the serious set of his eyes. "I came to ask for your help."

Sam rolled his eyes. "What, some whore give you the clap? I'm not treating that."

"It's Dad." Dean wasn't joking around anymore. "He's gone missing."

There was a small icy stirring in Sam's heart, but he had grieved too much lately to really feel it. "He's a pirate," he said. "They tend to do that."

Dean reached into his pocket. "He left one of his maps. And this note." He handed Sam a scrap of paper.

Sam took the paper and inspected it in the moonlight. The map game was one he knew intimately – when they were boys, their father would maroon them on an island with a map he'd made himself and a compass, and an X to mark the spot where the crate of food and supplies was hidden. He'd return in a few days. Sam hated the map game.

On the paper was scrawled Olhos Amarelos.

"Portuguese," Sam said.

Dean watched him. "Then you know what it says. And why we have to follow him."

Sam folded the scrap and set it on his bed.

"He left me the ship," Dean said.

Sam's eyes darted to Dean's instantly. "You brought her to England? Are you insane?"

"She's tucked away," Dean assured him. "A dock in Wales. I don't care what empire it is, nobody cares in Wales."

Sam flopped back on the bed. "Dean," he moaned, "please, just – go disappear in Jamaica or something. Dad will turn up eventually."

"You should really shave. That mustache makes you look like a Frenchman," Dean said. "And you're getting pale. You practically glow in the dark. You need some sun."

Sam ignored him and just closed his eyes.

"Is that your plan?" Dean asked. "You'll just sit in the dark and rot? Get whiter and skinnier every day?"

Sam tried to ignore how correct he was.

"I haven't asked you for anything," Dean said quietly. "Ever. And I'm asking now." He cleared his throat. "Please come with me."

Sam exhaled, and accepted what he'd known since he recognized Dean's face. "I don't really have a choice, do I?"

Dean smiled.

"Just one journey," Sam said. "Just to Portugal and back. Just to see if he's in trouble. Alright?"

Dean smiled wider.

Sam was already getting a headache. "Promise me we'll be back in a few months. That we'll go as quickly as humanly possible."

Dean nodded quickly. "I promise."

…

São Luís, Brazil, Five Years Later

"Faster!" Sam shouted. "We need to go faster!"

"This is as fast as she goes!" Dean shouted back. "She's a friggin' ship, you idiot! She only goes as fast as the friggin' wind!"

The crew frantically fretted at the rigging, yanking the sails as wide as they would go, all the while cannonballs whizzed about their heads. Every so often one would find its target and send a chunk of the boat splintering, and Dean shouted, "STOP BREAKING MY SHIP!"

Finally they outdistanced the heavier Portuguese ship, Ciclope, which was loaded down with spices and silver and had one sail in flames. The hold of the Impala was woefully empty, but at least they were out of firing range, and the burning frigate shrank mercifully in the distance.

"And now," Dean announced loudly, "We set our sights for England!"

A cheer went up among the crew, most of whom were not English at all – Sam and Dean included.

Sam wiped his brow and exhaled. Tanned like leather and the size of a bull moose, he wondered if any of his colleagues would recognize him now. He barely recognized himself. Meanwhile, the crew began to clean up the ship the best they could, making repairs that would hold until they could make port again.

Dean stood at the wheel, grinning and proud. He flipped open his compass and consulted the horizon.

"You make it sound like we'll be in Britain tomorrow," Sam commented. "But I assume we're sailing up the coast?"

"Of course," Dean said. "Yeah, we'll have to make a few stops along the way, but I did promise you, Sam. We'll get there." He glanced back at his compass. "Besides, I've got a pretty girl waiting for me." He raised his eyes dreamily over the seas, a far-off look in his face. "She's beautiful, Sam. And flexible. Limber like a ballerina. She could do this thing where she puts her legs behind her hea-"

"I get it," Sam interrupted. He joined Dean at the wheel, and looked out over the prow of the Impala, the glistening blue waters sparkling in the late afternoon sun. "It's been a long journey. But we did good, didn't we? We killed Yellow Eyes, found Dad…." He swallowed against the lump in his throat. "Gave him a burial at sea."

Dean's hands tightened on the wheel, and he nodded.

Sam sighed. "I guess what I mean is, it's been quite an adventure." He scratched the back of his head. "So… thank you."

Dean smiled. "You're welcome." Then he raised his voice so the other sailors could hear him. "Now go patch up the crew, Doc. I know there's at least one of these bozos who's stupid enough to get in the way of a cannonball!"

"I'm peachy, Cap'n!" Ash hollered from somewhere above him in the rigging. "But thanks for the concern!"

The other sailors laughed heartily.

"You know, I think one of those cannonballs looked at me funny," Henrickson called. "You better prescribe me some bed rest, Doc!"

They laughed again, and the Winchester brothers laughed with them, and Sam felt a great relief and peace in his heart that this was all finally over, and he was on his way back to his old life once again.

He had no idea how wrong he was.

It was just the beginning.

….

Belém, Brazil

The crowded tavern teemed with sweaty patrons, tradesmen and sailors alike; the oppressive humidity of the bar hanging in the air like a dank fog, and mingling with the curling wreaths of tobacco smoke, and clinging to skin and hair and damp collars. Jolly prostitutes tickled and grinned gap-toothed smiles, while drunken men leered and sloshed their watery drinks in approval. But out on the stoop of this fine establishment, there sat a man who did not seem to belong.

He sat quietly, in a long leather coat much too warm for the thick summer night. A small mouth and a blank gaze. His dark hair had been ruffled by some long-absent breeze, and eyes were a startling shade of crystal blue.

One particularly inebriated customer stumbled out of the tavern and nearly tripped on the man. He swore and did a double take. "Well who're you?" he demanded in Portuguese.

The man turned his head slowly and looked up at him.

The drunk shivered.

"I am a servant of Poseidon," the strange man said.

"What're you doin' out here?" the drunk asked.

The man turned his gaze back to the night beyond, out towards the docks and the beckoning dark sea. "I'm waiting."

The drunk blinked. "Fer what?"

The strange man stared out to sea, patient and silent and implacable, and said, "Dean Winchester."