Hello, this is based off of a post on Tumblr suggesting this AU, thought I'd give it a go!

Castiel watched as the various sailors of various crews entered and exited throughout the large port of the seaside town, Darton. He sat on the beach, listening to the waves clash with the laughter of the sailors and the commanding voices of their superiors. Flashbacks of his adventures and his former mates began to gather in his mind, he shook his head to try and lose them

With a sigh Castiel sat up from his spot in the sand and headed towards the small pub on the edge of town.

It may be early, but he needed a drink.

His hat was tipped down, casting a shadow on Dean's face as he strode through the crowded street, everyone bustling and advertising their lovely merchandise. One woman, Dean didn't bother to look to hard at her after noticing the absent space where her fingers should have been, tried to pull him over, begging with a desperate look in her eyes.

Dean pulled away from the old hag, speeding up his pace as he tried to increase the distance from him and the strange woman. His coat danced a bit behind him, the dark brown cloth fluttering a bit as it caught on to the breeze his movement created. It wasn't until Dean reached the Town's Notice that he stopped, a certain face catching his eye on the large board.

"What a handsome devil," Dean smirked. He couldn't help but feel a puff of pride as he observed the wanted poster hanging on the board; his wanted poster. He grinned a little bit wider as he read the several charges he had collected from his career option.

"Well this calls for a celebration, after all they did such a good job on my face!" Dean rubbed his chin, trying to imitate the face they had drawn of him. Smiling he looked around, and walked over to one of the various vendors in the crowded street. He stopped in front of a large, stout man.

"Excuse me sir," Dean cleared his throat as he gave a charming smile to the man behind the stand. The man raised an eyebrow, Dean cleared his throat again before muttering "not one for chatter, I see."

"What do you need, kid?" The man spoke gruffly, waiting for Dean to answer him.

"Well, I was wondering if you could point me out to any good drinking establishments in this town?" Dean was mentally kicking himself in the head, drinking establishments?

The man stared at Dean for a second before answering the strange guy.

"There's a nice pub out on the edge of town by the port, small place but good service." Dean nodded and thanked the man before turning around and walking away from the vendor, a grin forming on his face among the shadows formed on his face.

Castiel sat in the dark pub, watching the few who were there mingling out of drunkenness while he sipped casually from his own drink. A rather large woman walked by him, casting her eyes across him. She winked at him, and Castiel quickly looked down and stared into his drink.

He waited until the lady had swaggered away that he looked back up, he had been focusing on trying to not let his cheeks burn too much while the woman had feasted her eyes on him.

Castiel quickly downed the rest of his drink of liquid courage before raising his glass to the bartender, who smiled. He walked over, bottle in hand to Castiel's table.

"How's the weather, sailor?" The bartender asked as he refilled the glass before taking the chair across from the dark-haired man. Castiel grimaced, and he took a sip of his drink before replying to the scrawny, blonde bartender.

"No longer a sailor, Alfie. I was discharged a couple months ago." Castiel stared into his drink, once again he began to remember the adventures, the ship and the crew. He quickly downed his drink and set the glass down a bit harshly.

Alfie smiled, his eyes sad and concerned as he poured the former sailor another drink.

"This one's on me Castiel. But you might want to take it easy, friend."

Castiel raised his glass as a sign of thanks, "It's okay Alfie," he took a sip and sighed as he put the glass down. "Okay, now I'm starting to feel something."

Laughing, the bartender pulled the glass across the table and downed the rest of Castiel's drink. He winked at the former sailor.

"I'm sure you'll figure out something to do, Castiel." Alfie knocked on the wood with his fist before standing up and heading back to the bar. Castiel sat in his chair and closed his eyes, the liquor in his system making him feel all fuzzy inside. But at the sound of the door opening, the former sailor opened his eyes to see who also found the need to have a drink while the sun still shone.

Eyes wide, Castiel's jaw almost dropped at the sight of who walked through that door.

Dean walked into the small bar, breathing in the various smells that wafted from its walls and people. He noticed that one man in a long, tan coat was staring at him. He raised an eyebrow at the strange man, who in turn looked down at his table. Dean began to feel odd vibes drifting from the guy, but he shook them off and headed towards the bartender.

"I'll have whatever's good," Dean told the bartender, smiling at the blond server. The bartender nodded, "Sure, pal. Go sit wherever and I'll- George! Leave the poor guy alone!" Dean smirked and nodded several times before turning around and choosing a table near the guy who had been eyeing him earlier.

Dean looked around the small pub, but his eyes kept getting drawn to the dark-haired man who sat a table across from him. The man kept his head down, although Dean noticed his eyes flicking around, most of the time towards the pirate himself. Dean was so distracted by the strange character that he jumped slightly when the bartender set his drink down in front of him.

He nodded and thanked the bartender who smiled, but was drawn away from Dean when he turned to settle the now growing quarrel between George and his target. Once again Dean smirked, but he found himself staring once more at the man. Deciding that he didn't like the growing pit in his stomach, Dean finished his drink and placed some of the coins on the table, calling out a thanks once more to the bartender before rushing out the door.

Castiel watched as the infamous Dean Winchester left the pub. After the cursed pirate stepped out Castiel stood up and followed, calling out a farewell to Alfie. The former sailor stood by the door, looking around for any sign of Dean.

Immediately his eyes lit up as he spotted the hat the Winchester had been wearing, so he ran. Castiel rushed through the street, pushing past the bustling crowds, his eyes trained on that one hat; that one dark hat that bobbed up and down.

He was cutting the distance, but watched as the hat turned a corner. Castiel raced towards the alley and stopped as he reached the corner. He lay against the wall, his heart racing with excitement as he slowly looked around the corner.

It was then that a hand reached over and grabbed the front of his coat, pulling him into the alley. The former sailor was thrown onto the ground, and he looked up to the face of the infamous Dean Winchester.

The pirate held his sword against Castiel's throat, staring down at the sailor. Castiel's hand inched towards his own blade, though his eyes remained trained on the infamous pirate.

"Ello," Dean said, smiling down at his prey, "now I assume you know me, so who are you, good sir?" The pirate tilted his head, watching as the man's eyes were wide, yet surprisingly calm.

"Um," Castiel glanced down at the blade pressed against his neck, "my name's Castiel."

"Hi Cas, can I call you Cas?" Dean smirked as he continued to watch the strange man under his blade.

"Uh, I don't really enjoy being called that," Castiel answered, his hand now wrapped around the hilt of his blade.

Dean shrugged and pursed his lips, "Cas it is," he was silent for a bit as they both stared at each other.

It was then that Castiel unsheathed his sword and lashed out at Dean, who jumped out of the way. Castiel rushed up to his feet, sword now ready in his hand as he faced the Winchester.

Dean smiled slightly, but now he was excited, the adrenaline pumping through him as he locked eyes with Cas.

"Not bad, Cas. You do this often?" Dean wiggled his eyebrows a bit, and almost laughed as Castiel tilted his head in confusion.

"If your asking if I try to capture infamous pirates such as yourself, then no."

Dean shrugged, "Just trying to make small talk." The Winchester thrusted his blade forward, Castiel blocked and soon they were a dance of calculated steps and blows. They were weaving through the alley, until Dean managed to force Castiel into an abandoned shop.

Once again they were a whirlwind of swords, until Cas caught Dean off, and he managed to land a small blow on the pirate's leg, slicing through his flesh. Dean cursed, but Castiel maintained his advantage, and finally with the flick of his blade he cast out Dean's sword from his hand. He held his blade near the infamous Winchester, confidence in his eyes. But Dean's eyes were also confident as he pulled out a gun.

Cas lowered his blade, frowning. "You cheated."

Dean smirked, holding the gun level while he tried to stay off his injured leg.

"Pirate."