This is it guys, it's finally time to take a look into the past. But first, formalities are in order. This story has reached 100 reviews, and that's so amazing! Thank you DeerTopus C. (I hadn't actually heard that song before so I checked it out while writing this chapter, and you were so right. Reminded me very much about how I wrote Dean 0.o), Kather-Swine(Well, let's just say this chapter will be an example for others to follow, I guess. Happy and sad go hand in hand), lindsay16(Do not fear, I was hoping you'll could at least hold out for a couple of days; I hope the wait wasn't too long, or at least long enough for the suspense to set in), Akayuki Novak(It's always a pleasure, being the writer has its perks; especially when dropping subtle hints of not-so-nice things happening later on), and Air Guitar Pixie(Yesh, fluff :3 thank you, it just kind of came out and now I'm really glad it did. And aye, this be a land full of those awful...cliffhangers *shudders*). Thank you especially to those who are my regular reviewers, those who have been around since Day One. Seeing those names time after time, well I really appreciate it. Also, thank you to those who have followed and favorited, I send my love to you as well :3 Now, I guess it's time to finally approach one of the many elephants on the ship, here you go!


Out of nowhere a familiar smirk appeared on Dean's face, and Castiel felt his shoulders slump in relief.

"Sure pretty boy, I think I can manage that." His voice was soft as Castiel gradually let go of his shirt.

The former sailor wanted to smile. At this point, he wasn't even upset about the nickname anymore.


"Alright, first you should probably get your hands back; they won't give us too much time before they come down here to get us." Dean spoke, his position as a captain evident in his voice when he talked.

Castiel gave a nod, and Dean watched as the former sailor backed away from the pirate. Appreciation coursed through Dean, although it was polluted with the feelings of shame and guilt.

How could he let himself fall into despair when Castiel needed him? How could he let the monster inside of him deal the winning blow when the fight wasn't even over?

Not again, Dean growled to himself, One time is good enough for this lifetime.

Drawn out of his thoughts, Dean's attention was brought onto Castiel who now stood with his hands where they had been originally. He picked out the determination that roared in those familiar blue eyes, and it seemed to boost his own.

Straightening his shoulders, Dean took a step towards Cas. The back of Dean's neck burned as he and Castiel both froze, hearing approaching footsteps.

"Look," Dean hissed hurriedly, "Meg's a bitch and what she's got planned is going to suck for the both of us. The bonus is that she'll have to remove the cuffs; don't ask me why. But you try and stay as close to me as possible okay? Do that and we should be-"

Dean's words were cut short though as the door to the brig opened, revealing the familiar smug form of Ruby; her arms crossed while she grinned. Behind her was another woman, her eyes narrowing at the two in the cell.

"Time to go, boys." Ruby sang as she made her way over to the cell and unlocked the door.

Dean forced himself to breath, to calm the panic that was wanting to rise out of him. Yet somehow he kept himself collected, and with narrowed eyes and decisive footsteps Dean made his way out of the cell.

Immediately the woman who was standing in the doorway stepped forward, reaching out and grabbing hold of Dean's arm.

Ignoring his hammering heart, the pirate tried to push against the beast, who in turn shoved at the crack in the steel trap.

Leaking out, small glimpses from behind the wall escaped through the breaks that were forming in the crack.

Hands bound, a cold hand wrapped around his arm tightly while the own kept on a cold smile as they walked down the corridor.

The demon pirate began to lead him through the hallway, her face like that of a canvas yet to be drawn in.

Eyes, watching his every step as he tried to remain confident, his face stone and his stare only looking at what was in front of him.

As they made their way across, it was becoming more evident that all of the crew was most likely gathered on their deck. Footsteps and chatter growing louder and clearer as they continued on silently.

Silence was instantaneous as he was brought onto the deck. So many faces looked at him, the majority of their expressions the cold joy that was so common among them; but some almost wore a face that expressed a kind of sorrow.

Dean clenched his jaw as he and the demon made the ascent up the stairs and onto the deck of the ship, he could feel himself beginning to shake; though it was light and barely noticeable.

A dense forest sat on the formation of land which the ship floated nearby. The forage was thick and wild, the calls of animals and birdsong faintly carried through the breeze.

Unable to avoid it, Dean turned his head and couldn't help but freeze where he stood with a sharp intake of breath. The shaking grew stronger, his breath hitched in his throat as he couldn't take his eyes away from the familiar formation of sand and forestry.

The demon pirate that had kept a firm grip on his arm gave an exasperated sigh as she yanked the pirate away from his rooted position; causing him to stumble behind her. But Dean could still feel the island's presence, it never leaving the corner of his eye.

Faintly he could make out the sound of footsteps behind him, and Dean twisted his head barely to see that both Ruby and Castiel trailed a few steps in his wake. Quickly he turned his head around, green eyes scanning across the gathered demonic creatures that all stood at the bow.

A crew of many at the bow, their silence deafening to Dean as he was not used to pirates, especially demon pirates, being so quiet. The air grew cold as he came closer, able to see his own breath.

Stop it! Dean screamed at the monster, who shoved harder at the crack. The reinforcements were giving away, tiny holes expanding into much larger empty spaces. Pouring from them were dark, filthy forms of corruption. Polluting Dean's mind, clawing at him and dragging him away from the real world.

He grimaced as he was assaulted with the poisonous darkness, the way it seemed to swirl and coil around him. Sparsely, he could hear the cold laughter coming from inside the steel trap. It was manic and cold, somehow it even sounded pure to Dean's ears.

Being drawn out of his thoughts, Dean brought his attention back to reality as he was stopped by his holder. He tried desperately to calm his shaking hands with tremulous, deep breaths.

The crowd shook as a form moved its way through, making its way to the front. Watching with narrowed eyes, the familiar figure of Meg now stood at the head of her crew. Tightening his fists behind his back, Dean dug his fingernails into the palm of his hand to try and cease his quivering.

"You should appreciate the effort I put into this little send away, Dean. I figured you would enjoy a little bit of nostalgia before we part of ways."

"How thoughtful," Dean replied through gritted teeth, and he felt the grip on his arm tighten.

"Glad you think so," Meg replied with a smile and a slight tilt of her head. She turned to face the gathered demon pirates, some of their eyes switching between the chilling orbs of black and those which were deemed normal.

"As you all might know, this lovely gentleman is Captain Dean Winchester. Lucky for us, he has been so gracious as to donate his ship for our use, along with his presence for a short period of time." Meg looked back and flashed a grin at Dean, in turn the pirate jerked against his holder's grip; although she held strong.

"Sadly," Meg slumped her shoulders in mocking as she turned away from the crowd and took swaying steps towards Dean, "His time with us has come to an end. So we shall part ways with him here; at his final destination."

Meg's face seemed to light up as Dean continued to glare at her, but he tensed as she raised her hand up towards his face.

Instead, she patted his cheek, "It's been fun, all of this reminiscing, Dean."

"Oh it's been great," Dean snarled before pulling against the demon pirate's grip as he leaned close to Meg, "but if you still have my ship when I get back, I'm gonna be pissed."

Meg smirked, "Wouldn't have it any other way, Dean-o." She jutted her chin out at the one who held him. "Go ahead and take him to the edge."

He watched out of the corner of his eye as Meg walked up to where Castiel stood behind him.

"Hey there, Clarence," Meg drawled out as she stopped right in front of him. Dean panicked for a moment after forgetting to mention to Castiel about his fake name; and he could only imagine the former sailor wearing his confused look.

Turning his head, he saw that Castiel did indeed look confused, and his eyes glanced towards Dean. The pirate nodded rapidly several times, hoping that somehow the former sailor would understand. He watched anxiously as Castiel's brow furrowed.

"How do you know my name?" Dean gave an inward sigh of relief as his message seemed to have been understood by Cas.

"Little birdie told me," Meg replied slowly. She stared at Castiel in a moment of thought before walking back to where Dean now stood, the heels of his shoes on the edge of the ship.

"Now, if memory serves me, you were standing right where you are now." She walked back to where Castiel stood, and grabbed hold of a fistful of his coat. Tugging him forward, Meg led the former sailor away from his previous position, "and he would've been around right here." Placing Castiel a few meters to Dean's right; close to the gathered demonic beings.

Dean stared where Castiel stood, although it wasn't Castiel that he saw.

Standing to his right was a man who stood tallest among all of the specimen on the ship. Brown, shaggy hair that was longer than Dean remembered it being sat on the man's head. His face was blank, save for the look of resolve on his face. As if the man was victorious, somehow. Dean couldn't stop himself from cracking a bit on the inside, thin lines snaking around his portrayal of confidence. He allowed himself to deflate as the two stared each other down; words unable to escape either of them.

Dean's eyes sank to the wooden boards, his hands beginning to quiver. No longer could he block the escaping pollution; and from the darkness in the inside of the box he could see a cruel smile.

In front of the rest of the demon pirates stood a few of the supreme, the most loved of the crew. One of them was a woman with curly dark hair that surrounded her face, watching with both a curious and malicious gleam in her eyes.

"It's too bad that he isn't here, I think he would enjoy seeing you like this," Meg nodded towards the pirate who had remained by his side. Barely he felt the removal of the cuffs, but at the moment Dean's connection to reality was fading; he found himself drifting back towards that awful memory.

The crowd's attention was drawn away from the two though as a man clad in white stepped out of the captain's quarters. He approached slowly, dominance and authority shouting at everyone from the way he made his way down to the gathering. Both Dean and the tall man gave a sharp intake of breath, and for a moment the Winchester glanced at him before his gaze was drawn back towards the sharp dressed man.

His cold blue eyes drilled into the form of Dean Winchester; but the pirate did not back down from the challenge. His stubbornness brought a small smile to the dominant figure as he stopped in front of Dean.

"Hello, Dean," the man with the short blond hair greeted, the bottom of his face decorated in stubble which shared the same color. Tense, Dean kept his whole body stiff and confident as he replied with a smirk.

"Wow Old Scratch, you dress that nice just for me?"

"Although last time it was just one person that departed, so it makes sense for you to go." Dean blinked, unclear as to what Meg was implying while she stood next to Castiel; who wore the same expression as the pirate.

"But you see, this one right here could be a keeper," Meg dragged out before looking directly at Dean with a wide grin. "Just imagine all the fun I could have with this one."

Both Dean and Castiel's eyes widened, the former sailor looking to Dean who stood speechless, save for the feelings of anger that overrode all others.

"Meg-" Dean growled, but the demon captain interrupted as her eyes flashed black.

"Hell, give him a couple years and then we would have some real fun, right Clarence?" Meg batted her eyes at the former sailor, whose eyes narrowed at the demon as he continued to wear a look that carried both a frown and panic.

"Glad to see that even at the end you haven't lost your humor," Lucifer commented as he continued to adorn a small smile. "I will miss that most, I think." The captain rested a hand on Dean's shoulder. Turning to face the crowd, Lucifer's grip on Dean's shoulder tightened, a feeling of cold spreading throughout the pirate's body.

"As you all know, we are gathered here today to say goodbye to the soon-to-be departed; the charming Dean Winchester. Lord knows we've had to put up with him for awhile," a couple of snickers and cackles escaped the crowd of demons.

"Now, personally I'm bittersweet," Lucifer turned to face Dean once more, "you were such a pleasure to have around." Dean could feel his stomach churning as he looked into the devil's face, both of them thinking back to their history with one another.

"But it's okay, because even though today we lose a crew member, one is gained as well." Lucifer raised a hand, gesturing towards the tall man that stood to Dean's right. The tall one was silent, his face blank and unaffected.

Satan shrugged mockingly, "Guess he's not much of a talker."

Lucifer turned his attention back to the younger pirate, whose eyes were locked onto the taller of the two. It was easy for Lucifer to identify the way that Dean was looking at the other, he had been the recipient of such a look many times in his childhood.

Leaning in close, the devil whispered into Dean's ear.

"This may pinch," he warned before his hand shifted towards the back of Dean's neck, and he began to chant with a low voice.

"Te solutum fuerit debitum. Et dimittetis evasit. Tenet noctis mundavero vos ab illo vinculo animus. Et nunc absolvo vos. Ego te absolvo. Rursus in arma proficiscor humanitatis; daemonem."

"So you just going to stand there, or is someone going to have to push you; again?" Dean's heart hammered in his chest as he brought himself back to focus again, eyes locking onto the forms of Meg and Castiel. Meg's entire face was confident, glowing with pride and sarcasm.

Castiel stood near, his whole face illuminated by the sheen of panic and confusion. His eyes were wide with alarm and fear, unable to decide on a course of action. For a moment, the world was silent as they both stared at each other.

And it only took that one moment where the world seemed to stop spinning for Dean to decide.

He.

The back of Dean's neck burned as he felt the black smoke that had tainted the very core of him release its grip.

Promised.

All of the corruption it carried was locked away, and within the steel trap sat a monster. A monster that welcomed the feelings of cruelty. A monster that would later on pound at the walls, wanting to taste freedom again, to put its dark skills to use in the real world.

That.

He felt his balance slip away as he tottered back and forth. With a grin Lucifer released his hold on Dean after pushing him.

"Bye bye," the devil whispered as he watched the falling form of Dean Winchester.

He.

Time seemed to slow as Dean's feet left the floor, and suddenly he was a feather caught in the breeze; the lapping of waves cheering as he descended.

Would.

The tall figure leaned over the railing, emotions breaking through the stone mask that he had worn for so long after being weathered by such events of despair. Dean felt a piece of his heart break, something that he hadn't felt in ages, as he caught sight of the face.

Keep.

Eyes that he had only seen through a filter of cold and heartless now seemed to be free, drinking in everything with a new perspective. The sun was shining, a blue sky that was much more tame compared to its darker counterpart.

Himself.

Locking in on the face, Dean stared at it; drinking in all of the details that he hadn't bothered to notice moments before. He could almost make out the eyes, almost make out of what they were screaming that the tongue refused to share.

Together.

Before he was enveloped with the waves, Dean felt as if he had finally woken up. And after waking up, despite the damage that had scarred and changed the look in those eyes and that face, a day wouldn't go by that he wouldn't recognize it.

His back met the brutal ocean as he found his voice, his first word as a freeman escaping from his lips.

"Sammy!"

"No, I've got it covered," Dean uttered before he lunged forward, his hand finding a fistful of a surprised Castiel's coat. Meg began to drew her pistol, but Dean was quicker as he threw his foot into her abdomen and the demon captain was launched away from the two.

Immediately the entire crew had their weapons drawn, and bullets were launched at the two.

Dean pulled Castiel behind him, the former sailor lost in a whirl of confusion as he tried to find his footing while trying to avoid getting shot. It only took a bit for them to reach where Dean had stood, and blocking his escape was his holder.

The pirate stopped short as she held her blade out, battle-ready. Quickly, Dean threw Castiel against the railing, the former sailor in a complete state of shock. Dean held him by the front of his coat with two hands.

With both of their eyes wide, Dean couldn't help but give a grin of reassurance to the baffled sailor.

"Don't drown," Dean ordered, and before Castiel could reply the pirate shoved forward. Yelping in surprise, Dean watched as the former sailor fell to the waters below.

Looking back at the others, he saw now that they surrounded him, Meg standing in front of the others. Even with her black eyes Dean could easily tell she was pissed.

"You're lucky that I can't tear out your throat," she hissed. Dean didn't reply, instead his eyes taking in all of the pistols and swords drawn and pointed at him.

Focused, Dean smirked at the angered demon, "Come on Meg, I'm Captain Dean Winchester. Luck's got nothing to do with it," Dean replied before turning and jumping over the rail. His leap of faith was quickly followed by the sounds of multiple pistols firing in his general direction.

He bit back a scream as his right leg was hit by ammunition, his eyes watering before he impacted with the ocean's surface. The water didn't help his leg as he drifted underwater for a moment, wrapped in the arms of a peaceful calm that did not mirror the surface.

Resurfacing, Dean looked around to try and find Castiel. Doing his best to ignore the throbbing pain in his leg, the pirate began swimming immediately towards the familiar form of the former sailor.

"Cas," Dean tried to call out, but he was only met with the water's repetitive noises. He watched with a slight horror as the figure seemed to be still, and Dean desperately swam closer.

Finally reaching Castiel, Dean grabbed the former sailor's face. His eyelids were shut as he stayed on the water's surface, floating. Relief washed over Dean though as he felt the familiar throb of a pulse on the former sailor.

Coming to the conclusion that Castiel must have landed on his head when he fell, Dean cursed as he grabbed hold onto the collar of his coat, "Frickin' concussions man," he muttered in between strokes.

Tugging Castiel along, Dean was exhausted once he managed to reach the shore of the familiar island. Breathing heavily, Dean pulled both himself and Castiel away from the water before he collapsed onto the beach next to the former sailor.

"We're okay, pretty boy." He whispered to the unconscious man before he too drifted off into the comforting, thoughtless void.


Wow, this chapter was certainly one of the larger, more complicated chapters that I've written. I hope you guys enjoyed it, now that you got a peek behind the curtain with Dean. Then again, there's still much more to tell about all of them! Please review, follow and favorite if you enjoyed; it means a lot! See you for the next installment!