Wow! Can honestly say I was surprised and pleased by the initial reaction, thank you guys ^_^ A special thanks as well to Air Guitar Pixie and DeerTopus C. VonZenhousen for reviewing!

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."

Dean flicked the gun to his left, "toss the blade Cas," he ordered as he smirked, the pirate seemed to glow with confidence now that he was controlling the situation. Grudgingly Castiel obeyed, throwing his sword off to to his right.

"What are you doing here in Darton, Winchester?" Castiel asked as he stared down the gun in Dean's hand, his heart pounding in his chest.

"I'm here on business, you know. Being a pirate isn't all women and badassery," Dean squints his eyes and his grin widens a bit, "well at least not all the time." Castiel frowns at this, but Dean now walks back towards the door slowly, his pistol still trained on Castiel.

"Well Cas, I've had a grand old time with you. Now I don't make it a habit to kill pretty boy swordsmen, so I think it's time I make my leave." And with a tip of his hat the infamous Winchester turned towards the door and ran out.

Castiel quickly grabbed his sword that had been lying nearby, and rushed to the door. He reached for the doorknob, but the door wouldn't budge. Several times the sailor tried to open the door, until finally he began to throw himself against it. After several tries, the door gave way, and Cas landed painfully in his side back into the alley where his troubles had started.

He ran towards the crowded street, and desperately searched for the hat he had spotted not too long ago. His eyes scanned the people, but after not one sight of the hat he gave a growl of frustration and kicked one of many barrels strung across the alley. Castiel cursed, running one of his hands through his hair while he sheathed his sword angrily.

Pretty boy swordsmen, Castiel snorted at the thought, I'm going to find that fool.

Dean watched slightly afar at all the sailors buzzing about the port, leaning casually against a wall in an alley. He glanced down at his injured leg, he had managed to wrap it and was pleased that it wasn't severe. His eyes then began to take in all of the lovely ships, until a particular one caught his eye.

"There you are, baby." Dean muttered under his breath, his eyes now locked onto a particular sleek looking black ship. With a destination now set he got up from his previous position of leaning against the old building, and he began to make his way through the darkness of the various, crisscrossing alleyways he traveled through. He frowned, knowing he had to be careful now after his little meeting with Cas.

He was quite charming, Dean thought jokingly; smiling now as he remembered their confrontation that had only occurred a bit ago. Finally Winchester found the right building he was looking for, and he knocked on the back door forcefully with his fist.

"Bobby!" He shouted, and he heard the old fool curse as he eventually opened the door. Dean looked at the man, taking in his scruffy red and grey beard, and it wasn't hard to smell the alcohol that Bobby seemed to be soaked in.

"Hey boy," Bobby greeted, and he opened the door to make room for the pirate. Dean nodded towards Bobby as he stepped into the old house, it seemed to be in the same condition as the owner itself. The Winchester took off his hat and looked around the place before sitting down on a wooden stool, his eyes still sweeping around the house.

"So, Bobby," Dean began after the old man sat down across from him, " looks like you were right after all. She's here all right."

"Course I'm right idjit," Bobby replied before taking a sip of his drink, " don't you know I would've checked before letting you know?"

Dean smiled, a small chuckle escaping him after hearing Bobby. But his face grew a bit serious, and he looked at Bobby with a fierce look in his eyes.

"Do you have any new information on him?"

Bobby sighed, taking a moment to drink once more from the mug in his hand. He set the glass down and rested his hands on his stomach, his fingers intertwined.

"I've got a name for the ship he's on," Dean almost stood up with excitement, but something in Bobby's tone made him stay seated.

"And?" Dean asked while Bobby had remained quiet after his news.

"It's the Hellhound, Dean." The old man watched as the pirate's whole body seemed to freeze, Dean's jaw clenched as he closed his eyes. He almost immediately began to shake with anger, but he took a deep breath, and after several more he opened his eyes to look at Bobby.

"That son of a bitch," Dean muttered as he stood up and paced across the room, "of course it's the friggin Hellhound!" He stopped, hands on his hips as he looked down. His mind was racing as he tried to think of something, anything. But he shook his head, and walked back over to his chair before sitting back down with anger still burning in his eyes.

"So," Bobby said after watching Dean's reaction, "any plans on how you're going to get the Impala?"

"When there's a will there's a way Bobby, I'll figure out something and try to get out of here by tonight with her."

"Tonight? That's a little fast don't you think?"

"Well I kind of got made earlier by this one guy, but I managed to dodge him in the end."

Bobby frowned, "Happen to catch his name?"

"Name was Castiel," Dean replied, and watched as Bobby was now the one to begin to panic. The old man's eyes grew wide and he sat up, leaning forward in his chair now towards Dean.

"Boy, you just pissed off a former high-ranking sailor for the Royal Navy, you know what he's gonna do now that he knows you're here?"

It was then that Bobby and Dean both heard the ringing of the town bell, Bobby filled with dread when it rang five times.

"He must have alerted the guards that you were here," Bobby said as he now stood up and looked around the room before staring at Dean, "you need to get out of Darton now, boy. Trust me, these soldiers are thorough, and it's best if you're out of the town while they search."

Dean nodded, and quickly embraced Bobby, "thanks," he whispered to the old man before placing his hat back upon his head and racing out the door, Bobby watching as the pirate left.

"Good luck, Boy." He muttered before he sat back down and took a long sip of his drink.

Castiel thought hard, sitting once more by the beach after alerting the guards that Dean Winchester was in town. He couldn't help but smile a bit, he had enjoyed letting them know because they were rather thorough when it came to pirates; if Dean hadn't left town then he would surely be captured by the guards.

But Castiel decided he wasn't satisfied, he kept thinking about Dean and his encounter, the incident replaying in his mind.

"Pretty boy my ass," he growled and quickly got up before looking at the town.

The alleyways, Castiel thought while his head naturally tilted a bit as he thought, that's where I would go to avoid attention.

Castiel rushed to the town, he couldn't help but feel excited at the thought of capturing the infamous pirate. Finally he wouldn't have to the be the outcast, the sailor stuck on the land with the rest of these civilians when he should be out on the sea.

The former sailor weaved and raced through the alleyways, his eyes trained and focused in the darkness for any sign of humanity. Mentally he was doing his best to remember where he was, Castiel was searching just like the rest of the Royal Guards.

And he would find Dean Winchester, his heart was set on it.

Dean cursed as he crouched in the shadows the alleyway provided, observing the bustling crowd and the guards that weaved their way through the street and its people. He was at the home stretch, all he had to do was cross this road and he would be free of Darton until the alert died down, and then he could fetch his prize.

The Winchester glanced behind him, suddenly feeling a bit open from behind him, but there was no one there so he sighed and once again watched the street.

It was then that a guard noticed him, a young fellow whose eyes were bright and wide when he had spotted the Winchester.

"Damn it," Dean muttered as he turned and raced back into the web of alleyways, listening now as whistles were blown and footsteps were now following him.

"Not good, not good, not good," Dean kept muttering as he took turns and knocked over barrels behind him to try and slow the guards down. He took a sharp left, only to see a surprised Castiel. They both froze at the sight of one another.

"Oh come on, you again?" Dean shouted before turning around and racing back into the maze. He glanced behind him to see now that Cas was tailing him as well, and he growled.

"Really not good, really not good," he now muttered to himself.

Dean's eyes scanned for a way out, and then he noticed a nice little set of barrels that were stacked high enough to reach the roof, as well as staircase like. He risked one more glance at Cas, and couldn't help but smirk at the former sailor before he began to climb up the barrels.

Just as Dean made it to the top Castiel had begun to climb up the barrels himself, but Dean was a step ahead of the raven-haired man. He shoved the barrels, knocking a few over a long with Castiel who went down with them. Dean watched as the former sailor landed on his back, and managed to roll out of the way just as Dean launched another barrel at him.

The former sailor glared at Dean, who tipped his hat to the man, a grin on his face.

"It's been fun, pretty boy." Dean winked and turned around, and began to race across the rooftops. He tried to ignore the now stubbornly close whistles of both officers in the alleyways and those on the main street who caught a glimpse of the pirate on the roof.

Dean sprinted and jumped from one building to another, trying to stay ahead of the guards that were slowly surrounding him. His heart was pounding, the noise was almost consuming the rest of his hearing. He jumped once more onto another building, nearing the edge of town again. He ran to the edge of the building and froze. The next building was a bit of a distance, definitely greater than his previous jumping feats. Hesitantly Dean approached the very edge, and almost jumped at the sound of shouting guards. The pirate looked around and cursed, seeing that they too were on the roofs, and they were approaching fast. Dean stared at the distance once more, worry in his eyes as he tried to make a decision.

"Oh screw it," he growled, taking a few steps back before launching himself off the rooftop, reaching out for the next building's edge.

His hand grazed the wall.

Aren't cliffhangers (almost quite literally) great? I hope you enjoyed this chapter and I hope to post the next one in the near future! Reviews and the like are appreciated greatly!