Ahhh, here we are once more, back for another installment of Pirates! I'm looking at these reviews and can see that you all keep asking for a certain younger brother ;) Well, don't worry your pretty little heads; Sammy will definitely be in this story! I won't spoil the fun though for you about his own whereabouts just yet. Thank you to Kather-Swine(Happy Belated B-Day!), Deer Topus C. VonZenHousen, Akayuki Sawada, fictionfairytalesfantasy4921, Air Guitar Pixie, and Daughter of Rhea for reviewing. A thanks as well to those who have followed and favorited! Well, now that I've shared my two cents, better get on with what you came here to read, no?

"It's complicated. Charlie, could you get Balthazar to handle the wheel for a bit? I need to talk to Bobby."

The curiosity was blatant in the pirate's green eyes, but she nodded. "Aye, aye cappy," giving a fake salute she jumped down the staircase leading up to the wheel and searched out the active first mate.

Once more Dean sighed and released the wheel after noticing his white knuckles. Descending the staircase, the pirate captain made for his chambers. He held onto the doorknob for a moment, realizing how long it's been since he was last inside. Slowly his hand turned the knob.

Dean pushed the door open, taking a moment to look around at his redecorated room.

"Awesome," the pirate muttered as he looked at the various red and white banners that were scattered about his walls. One by one the captain ripped them from the walls, until he reached his desk with a fistful of wasted banners.

Upon his desk was a map, but Dean had no such use for this map. With a sweep of his hands he cleared his counter of assorted official documents. He watched as they flew and scattered about in the air before settling onto the floor.

Pleased now at the fresh look, the pirate captain tossed the banners on top of the fallen papers, watching as they slowly unraveled while remaining crumpled. Dean's fingers traced the edge of the desk as he walked behind it, pulling out the chair. All at once he slumped down into the old chair, appreciating that the navy hadn't messed with his father's furniture.

His eyes slid down the sides of his desk until they landed on a familiar set of scratches. Lightly his hand ran over the marks, rubbing his thumb over the carved letters that he recognized; sloppy as they were. He traced them with his finger, fluently following his familiar signature of D.W, but he froze when he moved onto the next set of initials. Subconsciously Dean began to chew the inside of his lip, his mind was at a standstill as was his hand.

"Dean?" An old gruff voice pulled the pirate captain out of his silence, jumping at the sound of Bobby's voice.

"Jesus Bobby, knock first before you want to give a man a heart attack." Dean joked, telling his heart to slow down while he drew his eyes away from their first target.

"You're the one that wanted to see me, idjit." Bobby's voice was Dean's anchor as he tried to shove away the boiling feelings inside of him right now. As Bobby closed the captain's door Dean walked over to the front of his desk, leaning back on it with arms crossed.

Bobby raised an eyebrow inquisitively as he approached the Winchester, stopping just short of the younger pirate before crossing his own arms.

"Are you waiting for an invitation, son?" Dean locked eyes with the older man, trying to figure out how he wanted to ask the father-figure. Finally the captain gave up, and instead spoke plainly.

"How come Cas recognized you, Bobby?"

Gabriel brushed his hands together, pulling Castiel out of his thoughts. The younger Novak brother watched as his brother sat up. Castiel slowly unravelled from his previous position, having drawn his knees to his chest and had his chin resting somewhat on his kneecaps. He looked at his older brother expectantly.

"Any ideas Cassie?" Castiel's gaze swept over the entirety of the room, eyes wide as he tried to notice every little crook and board.

"Possibly," the younger Novak replied, "how do you think Bobby knows of Dean Winchester?"

Gabriel grimaced, "I never really liked Singer." Castiel arched an eyebrow at his brother before smiling slightly.

"You only say that because he managed to catch you off guard." The older sibling muttered a retort, instead trying to bring back Castiel's attention.

"Focus Cassie, any way out?"

"Of course there's a way out Gabriel. But then what?"

"Improvisation," Gabriel suggested, and smirked as he watched Castiel shake his head, "would you rather stay here so you can talk to Captain Winchester, you flirt?"

Castiel narrowed his eyes at his brother, arms crossed now as he stood up. "Seriously, Gabriel? The man's a criminal and you want to talk about flirtation?"

"Just saying, I saw you two and you were definitely in the heat of the moment back there." Gabriel's smile remained as he watched his brother turned away with anger in his eyes, along with a flicker of something else.

"If I get us out, you think you can get us back to Darton?"

"Don't want to pursue your boy toy, Cassie?"

"Gabriel," Castiel warned, his voice low as he continued to look away from his brother.

"I think I could come up with something, I don't just stare at the sky in deep thought like you brother dear" Gabriel replied, shrugging his shoulders even though Castiel couldn't see. The younger sibling glanced back towards his brother before releasing a sigh.

Castiel approached the front of the cell, and turned to face Gabriel. His eyes locked onto the bench that his brother still sat on.

"Get up," Castiel ordered. Gabriel stared at Castiel curiously, wanting an explanation.

The former sailor pointed back to the door on the cell.

"Those are half-pin barrel hinges," Castiel's blue eyes flicked back towards the bench, "with the right kind of leverage and the proper application of strength, the door will lift free."

Gabriel's gold eyes filled with understanding and he immediately sat up from the bench. His eyes twinkled with pride as he looked at his brother. Together the two picked up the bench and Castiel commanded how the bench should be set. Two legs of the bench went through the gaps made by the crisscrossing bars, and with a cooperative effort the two shoved the bench down, and were met with a gratifying metal on metal sound as the door popped free.

"We better hurry, someone could've heard that." Castiel stepped out from the cell, casting his blue eyes around the room.

"Yeah of course," Gabriel began as he walked towards the door before turning around to face his younger brother.

"Hey Cassie, if you're so observant, why didn't you see how Winchester was going to get out?" Mischief danced in Gabriel's eyes as Castiel's eyes narrowed, although his younger brother's face turned red slightly.

"Bigger problems here, Gabriel."

Bobby was silent for a moment before walking over to a chair that sat against the left side of Dean's room. With a sigh Bobby sank into the chair, resting his elbows on the chairs arms while his hands settled on his stomach; fingers intertwined.

"Well like I said earlier, Castiel was a former sailor for the Royal Navy. I used to sail for the Navy too boy, if you can recall. Wasn't always assisting pirates and Lord knows what else I've done with you boys."

Dean's eyes were focused on Bobby, whose gaze was drifting between the captain's eyes and his own boots.

"Look kid, Castiel sailed under my command for a bit. He was a good kid, young and respectful. Nothing like either of his brothers; real quiet-like."

Dean nodded, his eyes distant as he thought about the former sailor.

"Definitely an oddball," the pirate captain muttered, and shook his head before making Bobby the focus of his attention once more.

"So, guess this is like the old times all over again; you back on the Impala."

Bobby smirked. "Sorry for the sudden intrusion kid, wasn't really my call either. Noticed those two running down the street and figured you could appreciate the help, savvy?"

"Aye, we're savvy," Dean replied, looking at Bobby. The man looked tired, as always, the way he sagged into the chair along with the darkness that collected under his eyes.

"Anyways, why don't you go rest up or something Bobby? You look like you've been avoiding sleep."

"I'm old boy, I'll sleep when I'm dead," Bobby countered as he stood up from his chair and began to head towards the door. Dean chuckled, but the feeling of concern lingered on the captain.

"Just take it easy, okay?" He watched as Bobby turned around to face the Winchester, a seriousness that wasn't present before came to his voice.

"Kid, I ain't the one who should be-" Dean intervened before Bobby could finish.

"I'm fine, Bobby. Okay? I'm fine. Go take a nap or something." Bobby stared at Dean silently, his eyes lingering on the pirate's green eyes; trying to convey all of his silent prayers and questions to the boy. Wordlessly the older man returned back towards the door and left, leaving Dean to his own.

The pirate captain stared at the door long after Bobby had left, his mind working through his scattered thoughts. Faintly he felt it stir, the dark spot in his head. With panic Dean jumped from inside his head and back out into reality.

Walking back over to his desk, the pirate captain slumped into his chair. Eyes were locked once more onto the carving on his father's desk, but he began to feel drained. After all of the day's excitement, Dean couldn't help but begin to close his eyes; his energy had been spent. Knowing that Balthazar should be able to get the others situated for now, the Winchester collapsed into an awaited slumber.

Cautiously Castiel walked ahead of his brother, wooden board in hand. The object was solid, and the Novak brother felt better having some sort of weapon. The stairs creaked slightly at the pressure that was put down on them by the Novaks' feet, and every time both brothers paused; waiting for someone to hear the now free siblings.

The two were surprised when they managed to get to the top of the stairs, and began to slowly embark down the long corridor that followed.

"You think they're all up top?" Castiel paused as he whispered to Gabriel, who shrugged before realizing his brother couldn't see him.

"Who knows, that would be something good for us for a change," Gabriel quietly replied, his eyes occasionally flicking up towards the sound of pirates walking on the deck. The younger Novak nodded, his eyes glancing up as well at the sound of footsteps above them.

Soon the two reached the end of the hallway, and a door stood before them. Gingerly, Castiel pressed his ear against the door, listening for anyone to be in the room. Quietly Castiel listened to the rhythmic snoring that came from the other side; he looked back towards his brother.

"There seems to be someone sleeping, other than that I assume everything else is coming from the actual deck above us."

"Assume?" Gabriel quizzed, eyebrow raised while his eyes flickered to the wooden boards above him.

"No one's perfect brother," Castiel snapped with a hushed, low voice. Gabriel shook his head, trying to hide his small smile from his younger sibling.

"Fine. Just continue; quietly would be favorable."

"I'm not a moron Gabriel." The younger Novak narrowed his eyes at his brother as the older sibling snorted. But they remained silent as they continued to hear the constant footsteps above them.

Gently Castiel rested his hand on the doorknob attached to the start of their way into the main room. Gradually he turned his hand at a painstakingly slow pace, both were silent as they subconsciously held their breath. The click as the doorknob reached the end of its rotation seemed to shout in the hushed air.

Castiel winced as he pushed forward on the door, and it responded with a faint creaking noise. He could almost see Gabriel's facial expressions as he proceeded to slowly open the door, his grip on both the doorknob and the board in his hand iron-tight.

Finally the doorway was wide enough, and Castiel cautiously peaked through the crack, his eyes scanning the empty room save for the sleeping man in a hammock. Recognition flashed in Castiel's eyes and he turned to alert his brother.

"It's Bobby," the younger Novak told his elder brother in a hushed voice, noticing the slight narrowing of eyes that Gabriel responded with. But it disappeared in a flash as Gabriel transitioned back into his usual smirk.

"Since when does Bobby Singer sleep? I thought that man was an insomniac." Castiel tilted his head in response before turning around to face the nearly empty, spacious room once more.

"Now is the time for silence, Gabriel." Pleased by the quiet that responded to Castiel, the younger sibling began to step out of the hallway and into the sleeping quarters. Striking blue eyes remained locked onto a sleeping Bobby as Castiel left the cover of the hallway and its doorframe.

Just as Gabriel began to follow, the two boys froze at the sound of laughter and approaching footsteps descending down the open stairwell.

As always thank you for reading and I hope you enjoyed this chapter. I'm starting to form a schedule, I would probably post three times a week; as soon as I get it completely figured out I will let you all know! Please review, favorite, or follow if you enjoy this story!