So I already wrote a Oneshot similar to this but I changed a few things around in the first chapter. O.O. So here we go. This is a lot like the show, Prison Break.

This fic is kinda dark. My first time posting anything like this for SPN.

This is an A/U version with a SPN crew all in prison getting ready to break out. Sam, Dean, Castiel, Michael, Lucifer, Gabriel, Balthazar and Crowley are all in prison for murder when they have a plan to break out.

Pairings:

Sam/Gabriel

Dean/Castiel

Slight Dean/Michael

Implied Dean/Alastair

Warnings:

Violence, Torture, Blood/Gore, Swearing, implied rape/non-con, typical prison behavior, Character Death (not the main characters)

. . .

Dean didn't want to believe it. He just couldn't, not with the way things were going so well before. He took a shaken breath as he was shoved into the cell. He stood there for a moment before turning just as the cell closed and the guard glanced at him, "Good luck, pretty boy," he said before walking away.

Dean took that moment to scan around outside the bars where prisoners were sitting in their respective cells, each hooting and hollering, singing and shouting. Dean didn't miss the way several men whistled and cat called when he walked by.

He knew one thing for sure; he was screwed. One way or another, he was going to either get killed or take himself out before becoming someone's bitch. He knew he didn't stand a chance against half the men in the prison…not without his tools. Not without his dad or his teacher.

Dean let out the breath he was holding as he turned to place his stuff down on the bottom bunk but he was shocked to see someone already residing there. He almost sighed in relief at the sight of his cell mate. This guy was average sized with unruly, dark hair and piercing blue eyes. Scruff was light along his jaw and his expression was purely blank as he stared at Dean.

"Would you like to be on the bottom or top?" the man asked, surprising Dean with the gruff of his voice.

Dean swallowed thickly before just knitting his eyebrows, "Excuse me?" he asked, praying that the man was talking about the beds and not something else.

"Top or bottom?" the man asked once more, staring at Dean like he was stupid.

"Uh, top," Dean said when the man motioned at the two beds.

The man nodded before turning back to the notebook in his hands.

Dean bit down on his lip before placing his stuff onto the top bed. He then took a step back to examine his cell mate.

"Why are you staring at me?" the man asked after a moment, staring up at Dean.

"Just want to know who you are considering we are probably going to be roomies for a while," Dean said with a shrug. He knew to act nonchalant in order to stay strong.

"Oh," the man said before smiling. He placed his book down and stood up, holding out a hand, "My name is Castiel," he said.

"Dean," Dean replied, hesitating before taking the other man's hand. Castiel just smiled before letting go of the shake. He glanced at his wrist where there was a watch.

Dean thought about it and realized the name 'Castiel' sounded so damn familiar. He wasn't sure where he heard it before. It wasn't as though it was a common name but it definitely struck a thought from him.

"So…Dean," Castiel said, "How long are you in here for?"

Dean lifted his eyebrows, "Um…life."

"Are you guilty or innocent? I need to know who I'm dealing with," Castiel said firmly, staring behind Dean as a bell run and all of the cells opened.

"The court found me guilty," Dean said flatly, hoping it was intimidating enough.

Castiel nodded, "We have that in common," he said before walking out of the cell.

Dean just lifted his eyebrows in surprise. This guy definitely didn't seem like the type to murder anyone. It was just absurd from how innocent he looked.

It was silent in the cell as Dean climbed up to put his bed together. He paused when he sensed eyes on him. He jumped down and turned to see a man leaning against the cell, his green-blue eyes sizing Dean up.

"What the fuck do you want?" Dean snapped, noticing this guy wasn't too big. He was just a little taller than Dean and firmly muscled, not really a big threat.

"Well now that isn't the way you greet the man whose going to make your life a lot easier in here," the man said, his voice smooth and cool. Dean noticed a couple other guys standing behind him, each shaking their heads. Now Dean was starting to feel concerned, considering the size of these guys.

"What's your name?" the man guy asked, lifting his angled eyebrows. His hair was dark, almost black and just a little long.

"Winchester," Dean said flatly, now wondering what these guys wanted.

"You're first name," the man ordered.

"Listen, I'm not going to be anyone's little bitch so you can just forget it," Dean snapped, making sure to stand firmly.

The man smirked and shook his head with a light chuckle, "You can't be sure about that," he said, "Now tell me your name."

Dean felt something in his body urging him that this guy was dangerous. He took a deep breath, "Name's Dean," he said flatly.

The man smiled a warm smile, "Well Dean, my name is Michael."

Dean gave him a nod, "Who are your buddies?"

"You don't have to worry about them," Michael said before walking more into the cell. He gazed around, "You cell mates with Castiel?"

Dean just stared at him, feeling his blood start to rush as the hair on the back of his neck stood tall. He had a natural instinct for picking out the dangerous men and this guy was sending off vibes big time.

"I think you'd be safer with me," Michael said after a moment, "I can make sure you're nice and cozy here."

"Screw you. As I said, I belong to nobody," Dean snapped, "I'll be fine here."

Michael's expression was blank for a moment and before Dean could react, he felt himself slammed into the wall of the cell with Michael pressed up against him. Dean struggled to move but this guy held his wrists down.

Dean turned his eyes to where the two other men stood in front of the cell, blocking it with their massive bodies.

"Get the fuck off of me," Dean growled, trying to swing.

"I suggest you show me some respect. I can assure you that you do not want to be with the others. They will not hesitate to have their way with you," Michael purred against Dean's ear.

Dean felt his heart racing in his chest as this guy seemed a lot stronger than he looked. He took a deep breath, "I said no," he ground out.

Michael pulled back slightly to stare into Dean's eyes and he swore there was sympathy in them, "You will say yes, Dean because you will want my protection. The only thing I ask is that you be loyal to me."

"No," Dean snapped, taking all of his willpower not to finch when Michael lifted his hand. Michael grinned lightly before running his fingers over Dean's cheek.

"Leave him alone, Michael," another voice broke through and Dean recognized it as Castiel's.

Michael smirked at Dean before letting go and stepping back. Dean tried to take a swing but his hand was smacked away by Michael, who wasn't even looking.

"Castiel…I'd like to trade cell-mates with you," Michael said, "I can give you that favor you needed."

Dean felt a lump in his throat as Castiel's eyes sparked with interest. Michael glanced at the two men on either side of Castiel and they both gave a nod then walked a few feet away from the cell.

"Out," Castiel said to Dean, who shook his head.

"No way. You are not bargaining me away like some friggen horse," Dean snapped with annoyance.

"Dean, leave this cell right now or I promise you'll be Michael's new cellmate without another thought," Castiel said firmly.

Dean wanted to stand back but somehow he knew he had no say. He glared at Michael and Castiel before walking out.

Once he was outside, he felt another wave of hair standing as a bunch of other prisoners all stared at him in a way that wasn't entirely comfortable. Dean ignored them and leaned back against the wall beside his cell. The two men who were with Michael turned to stare behind him.

Just as Dean turned, he found himself being closed in by four more guys. He stood straight and stared defiantly down at the one closest to him. He had short blonde hair and ice blue eyes. He looked completely cold and emotionless.

"Aren't you just a pretty one," the man said with a smirk, "I noticed Michael eyeing you."

"Go screw yourself," Dean growled, "Get out of my face or I'll knock you out."

The guys just started laughing and shaking their heads and the leader, as Dean noted, just smirked a cruel smile.

"I see Michael has already come to you," the man said, staring blankly, "I can assure you that you don't want anything to do with him."

"Listen, I don't want anything to do with anyone so get the hell away from me or you'll regret it," Dean growled lowly, trying to stay intimidating. He was warned long ago by both his dad and his 'teacher' that if he ever went to prison, he was a dead man. He was said to be too pretty for prison.

"Lucifer, I suggest you back off," one of Michael's men said, shoving at two of Lucifer's men.

Dean felt his stomach turn at the name 'Lucifer' and he knew this guy had to be very bad to deem that name. He also thought of the irony of the names, Michael and Lucifer.

Lucifer backed away from Dean to turn to the others who looked ready to start a fight with his guys. Lucifer held up a hand to his men who both nodded and stepped back. Dean noticed other prisoners staring and starting to walk over as if a nice fight was about to break out.

Dean instantly went to move but one of the bigger guys placed a hand on his chest and shoved him back.

Michael took that moment to walk out with Castiel and his eyes darkened when they set on Lucifer, who also glared at him right back.

Dean could sense the dark atmosphere from the two men and he suspected everyone else did as well because it became scarily silent.

For a moment, the two men stood close, each staring defiantly before Michael turned and snapped his fingers. Instantly, Michael's men began to follow as he turned around to leave. Lucifer then did the same, taking his men with him.

Castiel stared at Dean for a long moment before giving him a nod and walking away.

Dean let out the breath he had been holding before swiftly sliding into his cell. He wasn't sure what he was going to do. All he knew was that he needed to get out and fast.

. . .

Dean sat alone on the bleachers when they got their time outside. He kept his guard up, watching as several others spoke amongst themselves and glanced in his direction.

"Hello Dean," Castiel said from the side.

Dean nearly jumped in shock at how this guy just came out of nowhere. He spun around to stare at blue eyes. Castiel was sitting stiffly with his overshirt slightly unbuttoned.

"Hi," Dean said after a moment, noticing how people began to look away once they noticed Castiel. Dean wondered if this guy was a big deal in the prison.

"You should know that I refused Michael's offer," Castiel said after a moment.

"I don't need any favors from you," Dean said flatly.

"I did it because I allowed Lucifer to be with my last cellmate and…well, as you can see, he is no longer here," Castiel said slowly, "He was a nice guy."

Dean was silent after that, realizing that Lucifer had to be a lot worse than Michael.

"You should know that you will have to choose a side or you will not last long in here," Castiel said firmly.

"Why are there sides…what is this, high school?" Dean said, shaking his head, "I don't like either of the guys who confronted me."

"I would normally suggest Michael for someone as pretty as you but he seems to have taken a rare interest in you," Castiel said.

"I'm not going to be someone's little bitch," Dean said, shaking his head.

"I am just trying to warn you," Castiel said, staring around.

"What about you? Who do you side with?" Dean asked.

"Nobody," Castiel said with a shrug, "I'm fine with both of them. I have a group of others. I'd say you could join us but I'm not entirely sure what you've done in the past therefore, I don't know how the others would take to you."

Dean just stared down, "I'm sure if you knew, you'd throw me out."

"You don't know anything about what I would do," Castiel said flatly, his expression blank.

"I used to interrogate people," Dean said slowly, finding it odd how he trusted this guy.

"Torture and kill?" Castiel asked, straight to the point.

Dean licked his lips for a moment before nodding.

"What reasons did you have?" Castiel asked, lifting his eyebrows.

"Yeah, they all deserved it if that's what you're asking. They had it coming," Dean replied smoothly, wondering if that information would be enough to pass around and get people to leave him alone. He pondered just letting the full truth come out and how he had a lot of connections.

"Dean Winchester, you have a visitor," a guard shouted, slamming his hand on the gate.

Dean turned to him and nodded as he stood up to walk down the bleachers. Castiel simply sat there, soundless as Dean began to walk towards the fence. He paused when his eyes set on another prisoner watching him from the corner of the yard. Dean felt his stomach turn with absolute dread when he recognized the man as the exact one who tortured Dean for months before he taught Dean all he knew about torture himself. This was the one man that Dean feared more than anyone or anything. The one man who was supposed to be dead; Alastair.

Alastair's eyes landed on Dean and the corners crinkled with the smirk Dean knew all too well. It was that moment that Dean realized how truly screwed he was.

"Winchester," the guard snapped and Dean took a deep breath before following him.

. . .

Dean took long, deep breaths as he was brought to the meeting room.

"You have friends in high places," a guard said before giving Dean a push.

Dean stared around for a moment before his eyes landed on a man he thought he'd never see again. He smiled and stood up, "It's nice to see you, Dean," he said, holding out a hand.

Dean stared wide-eyed, "Dad?" he asked as he sat down.

His father, John, stared around and shook his head, "No, it's Allen Carthen, you're lawyer," he said slowly.

Dean just swallowed thickly before sitting down with John. He couldn't even believe his eyes as he stared at the man he hadn't seen in years, "What are you doing here? Where have you been?" he asked, feeling somewhat angry that he had been looking everywhere and his father obviously didn't want to be found.

"I've been busy, Dean," John said in a quiet voice, "I am not far from finding your mother's killer."

"Then why haven't you had me help?" Dean asked, having the urge to punch the table.

"It's too dangerous," John said, shaking his head, "You were fine on your own with the little stuff."

"I got caught," Dean growled, "held at gunpoint by this wife beater's wife. They conned me so they could turn me in and get the money."

"Dean…I'm going to get you out of here," John said, shaking his head, "I'm sorry this happened."

Dean ground his teeth and could see the concern in his father's eyes, "How long?" he asked, "and how are you going to do that?"

"We got Bobby out, remember?" John said, "It's possible."

"That's because you managed to pay off the friggen cops holding him. He was in a holding cell…not a friggen prison!" Dean hissed, "It's not possible."

"There are already a group of guys trying to break out," John whispered as he fumbled with thumbs.

"What?" Dean asked, staring around but nobody was close enough to hear.

"I need you to find the mastermind of it," John said slowly, "when you find him, you need to tell him…" he took a deep breath, "just tell him 'the righteous man sheds blood'."

"What?" Dean asked, pulling back a little to shake his head, "What does that even mean?"

"Just tell him," John snapped, earning a few glances. He hushed down, "That's an order, Dean."

Dean took a deep breath then nodded, "Fine…so who is this guy?"

Dean could tell by looking at his father that he was hiding something, "His name is Sam…Sam Campbell."

Dean recognized the name at once, "As in, my grandfather?" he asked incredulously.

John shook his head, "No…he just has the same name."

Dean glanced at him skeptically, "You're leaving something out. I know you."

John took a deep breath, "Just do as I say. I'll be checking in every day to check on you."

"Okay!" Dean said slowly, "When is this going down?"

"It takes time. Talk to Sam," John said sternly.

"Alright," Dean said, defeated. He never disobeyed his father's orders.

"So how have you been here, anyways?" John asked slowly. For how little his father ever showed emotion, Dean was surprised to see the genuine concern.

Dean took a deep breath as he remembered who he just saw, "Alastair is here," he said.

In that exact moment, Dean saw the color drain out of his father's face. John composed himself a moment later, "Don't let him get to you, Dean, you hear me?"

Dean pressed his lips together and shook his head, "I can't do this," he said, "I can't face him like this."

"You aren't stupid, Dean. Figure it out. Whatever happens, don't let Alastair have his way or you will be dead in two days," John said and for the first time, his voice shook.

Dean closed his eyes and pressed his face into his hands, "I don't know how long I can last. I've already had two guys trying to get to me."

"Who?" John demanded, "Did anyone touch you?"

Dean shook his head, staring at his fuming father, "No, nobody has. They seem to care a lot about the opinion of my cell mate."

John nodded, "Okay," he said, "Well, I have to go make some arrangements. Talk to Sam…remember what I told you."

Dean stood up with his father and gave a strong nod, "Yes sir," he said before allowing the guards to pull him away.

. . .

I was going to post this all in a oneshot since I have a lot written already but I decided to do chapters that way I can change things up if you ask for it in reviews.

I know this is so strange and unlike my usual fluff…but I've been wanting to do this. Please leave a review for some support and what you think. :D