A/N: Back writing serious angst again…So I've wanted to write a story with Alastair for a long time because I thought he was a seriously awesome baddie who had a lot of potential and died too soon in my opinion. So I decided that I would make the story an AU of "On the Head of a Pin" 4x16. Pretty much it's a direct tie in with the episode, but Sam is not on demon blood and he's working with Cas instead of Ruby. I really hope you all enjoy the story because I had a really fun time playing with the characters, especially getting to explore some of Castiel's inner struggles. I hope I did justice to his character, this is the first time I've written him from Season 4 and he was a lot different back then, but I hope I was able to portray what I wanted to and still keep him in character. And also I hope my Sam turned out okay too, because I was trying to balance the same angst he had without the added demon blood. Anyway, hope you all enjoy and I look forward to hearing what you think of this!

Rated T for violence and torture, because you kind of have to figure that's going to happen with Alastair. And again, this story is NOT slash.

Disclaimer: I do not own Supernatural; some of the dialogue in this chapter was taken directly from episode 4x16

The Breaking

A Supernatural Fanfic

Chapter One

The First Seal

Dean's knuckles whitened on the blade that he held in his hand, his back to Alastair before he slowly turned around, forcing a smile onto his face. No, it was impossible; he couldn't have been the one to break the First Seal.

"You're lying," he said, advancing on the trapped demon again.

"'And it is written that the first seal shall be broken when a righteous man sheds blood in hell,'" Alastair quoted with a satisfied, sadistic smile on his face. "'As he breaks, so shall it break.'"

Dean's stomach clenched at the words, a chill taking hold of his spine as he forced himself to stay calm, to turn around again before Alastair could see the fear in his eyes. It wasn't true. It couldn't be. If he had actually been the one responsible for starting the freaking apocalypse of all things, then why would the angels have rescued him? It didn't make sense. It couldn't.

"We had to break the first seal before any others; only way to get the dominoes to fall right," Alastair continued, obviously enjoying the fact that he was getting into Dean's head. The hunter couldn't allow that, he knew he had to keep his head, but realized he couldn't. Alastair had hit a sore spot and he just kept digging. Just like when Dean had been on the rack in hell, and truth be told, he still hadn't gotten over that. "Topple the one at the front of the line." He chuckled as Dean still refused to turn around. "When we win," Alastair continued, mocking. "When we bring on the apocalypse and bring this earth down, we'll owe it all to you…Dean Winchester."

Dean swallowed hard, his throat constricting with fear. No, he tried to tell himself. Alastair was lying to get under his skin. Demons lied all the time, he knew this. He forced himself to get his head back in the game but it seemed too late now. He was a mess, he knew it, and he also knew that he couldn't do this. Not now. Maybe a break would help…

"Believe me, son," Alastair said as Dean closed his eyes, trying to calm himself, to ignore the demon. "I wouldn't lie about that. It's kind of a…religious sort of thing with me."

Dean swallowed hard again, opening his eyes. "No," he said with sudden, terrifying conviction. "I don't think you are lying. But even if the demons do win, you won't be there to see it."

He turned around, ready to finish the job despite what the angels wanted, but saw Alastair standing right at his back, out of his chains and grinning. Fear gripped Dean as his mind tried to process this new development past all the other things it was processing at the moment.

"You should talk to your plumber about the pipes," Alastair told him before he swung a fist and slammed it into the side of Dean's head before the hunter could make a move. Dean dropped, the knife clattering from his hand as he sprawled on the floor and Alasdair was on him before he could regain his feet, hand gripping in his shirt, several more severely punishing punches to the head. His vision was already blackening, but Alasdair bent and gripped him by the throat, hauling him up to his feet and slamming his back against the iron trap the demon had previously been chained to. Dean choked, trying to gain at least one breath as he felt his feet leaving the floor, Alastair's face close to his as he continued to choke the life out of him.

"You've got a lot to learn boy," Alastair whispered. "So I'll see back in class bright and early Monday morning." Then he snapped his fingers and Dean completely blacked out.

Castiel had just gone out to watch Anna leave, his mind in turmoil over what she had told him. It had only been for a second, but then he felt something….wrong. With trepidation, he entered the abandoned factory once again and pushed through to the room they had been keeping Alastair in, finding it empty, the chains on the demon trap hanging loose and blood spattered outside the ring, which he could tell was human. Dean's.

"No," he said quietly, casting about for some clue, trying to locate Dean but couldn't sense him anywhere. He was either far away, or Alastair was concealing him from the angels.

Castiel felt a foreign darkness inside of him, in the pit of his stomach. Regret? Remorse? Something he wasn't used to feeling, or rather, something he didn't allow himself to feel, especially after he had already been demoted because of his all too human feelings regarding the Winchester brothers. He couldn't afford to let his emotions get away from him again. But yet, this was his fault and he couldn't help but feel remorseful about what had happened. Dean had practically begged him not to make him do this but he had to follow orders.

Everything Anna had just said to him came into sudden sharp focus. Maybe they weren't God's orders after all, maybe… but no, Castiel couldn't afford to think that. He couldn't.

And yet it was something that would eat at him until he was forced to think on it seriously, of that he was certain.

But right now he needed to locate Dean Winchester before Alastair broke him for a second time.

Dean woke blearily, cold, sore, and with a certain dark hollowness inside of him that he couldn't remember the reason for. He groaned and shifted against the hard surface he was slumped on, realizing he couldn't move very well. He forced his eyes open, and saw he was lying on the floor of some dark room, likely a basement or something from the cold wetness of it. Memories came flooding back then, of Alastair; Castiel and that douchebag Uriel had made him torture his old master for information. Then something had happened and Alastair somehow managed to get free, beat him up. Then he blacked out, or at least had no memory of what had happened after.

But there was something else. Dean closed his eyes against his aching skull and tried to remember it. And then he did, and wished he hadn't.

And it is written that the First Seal shall be broken when a righteous man sheds blood in hell…

He forced himself to forget again, squeezing his eyes tighter, unable to think about that and worry about his current situation and how to get out of it. Instead he focused on how cold he was and the fact he was in a very bad position. He had been stripped to just his t-shirt and jeans, even his boots and socks had been taken off, his bare feet adding to his chill. His hands were bound tightly in front of him and his legs at the ankles, making it difficult for him to shift around, not to mention the ache in his body. He pulled against the ropes, but only really managed to chafe his wrists.

He was startled by the creak of a heavy door opening at one side of the room. A light was turned on, and he realized that he wasn't in the same room he had been torturing Alastair in as he had thought at first. This room was smaller and there was a table off to one side and a covered cart like the one he had carried the implements to torture Alastair with. Dean swallowed hard, knowing where this was likely going to go as he looked up finally at the man who entered the room.

"Well, well, well, look who's finally awake," Alastair said in his nasally lisp, The wounds he had sustained had healed already and he had changed into clean clothes without bloodstains.

"Why don't you just go back to hell," Dean growled, his voice hoarse from the strangling he had sustained.

Alastair crossed to him and reached down to grab the ropes that bound his wrists, pulling him up and pressing him against the wall.

"We can have just as much fun here as we can there," the demon assured him with a sadistic grin, reaching up to pat Dean's cheek. "I'll just have to be more careful of your mortal body."

Dean tried to struggle, but Alastair held him tightly, getting close to his captive and chuckling as Dean finally turned away. "Oh, come on, my son, tell me you don't miss it? All the good times we had together. My apprentice, and a damn good one too. It was a shame the angels took you away."

"I don't know," Dean replied, finding some of his old bravado. "They ended up making me torture too, after all. Go figure, right? But I don't know why you want me. They'll just find me eventually, and then kill you. Trust me, it's not easy to hide from Heaven's hit squad."

"I've warded the place against the feathered annoyances," Alastair assured him with a grin. "We won't be interrupted, don't worry."

"What do you want, Alastair? What can I tell you that you don't already know?"

"Oh, Dean," Alastair chuckled and shook his head. "This isn't about information. This is just for old time's sake. A little…reunion, so to speak." He reached into his pocket and pulled out a razor, always his favorite implement, and Dean suddenly felt weak in the knees. "Remember our old friend, Dean? She remembers you. We're going to have, oh, so much fun."

Sam paced the hotel room, anxiously biting his knuckles and trying to figure out what the hell he was going to do. He hated sitting idle, but there was nothing he could do until he knew…well… something. Anything at all, really, would do. The angels had just whisked Dean off to parts unknown without a by your leave, and to what purpose? To act as their torturer? Obviously they were too good to dirty their own hands so they had to force the job upon his brother who was trying to forget what he had gone through in hell, what he had done, because apparently that was all Dean was good for anymore. Sam was beyond furious about the whole situation, and wished he could do something, anything, to at least find out where they had taken Dean.

"Castiel!" he cried finally, thinking maybe praying to the angel would get his attention. He had seemed a little more lenient than the others, even though he seemed to be under Uriel's thumb at the moment for whatever reason. "Castiel, answer me, you bastard! I want to know where you took my brother!" After nearly half an hour shouting uselessly, he finally ended with, "At least tell me when you'll bring him back!"

He slumped onto the end of one of the grungy hotel beds and lowered his head into his hands as he sighed tiredly. He didn't like anything about this situation. The angels obviously had some plan for Dean but they weren't willing to tell him about it, and on top of that, they didn't seem to see, or care, that Dean was in a bad place right now. Sam knew his brother better than anyone, and he saw the damage hell had done to Dean. His heart still ached when he remembered his brother's strangled confession about breaking in hell, torturing souls in his place for Alastair. It had broken him in more ways than one, and Dean was only half the man he had been before. Sam had been trying to put his brother back together again, but the angels and their crusade with these stupid seals weren't helping. They were only making it worse, especially if they kept making Dean do these kinds of things. They may as well throw him back into hell like they threatened.

Sam started to call to Castiel again, when the angel suddenly appeared in the room, startling him.

"Oh, now you show up?" he demanded, standing and glaring down at the shorter figure. "I've been calling for hours!"

"I heard," Castiel told him blandly. "I couldn't come."

"Not even to answer my questions? Where's Dean?"

"Sam I need you to listen to me carefully," Castiel said slowly, but Sam cut him off, too angry to care about any excuse the angel would make.

"You know what, Cas? No, you listen to me. You may not be able to see it, but Dean is broken, I don't know what exactly is going on with him, but he can't do things like he used to. Whatever happened to him in hell broke him and if you keep forcing him to do little tasks for you like torture people, especially a demon who will drudge up the worst memories possible for him, I will take him away and hide him where you will never find him. Good luck stopping your apocalypse then, if we're really that important to you."

Castiel stepped closer to Sam, his gaze intent upon the younger Winchester, something in his stance finally making Sam go quiet. "I am following orders like everyone else, Sam, none of us have the luxury to sit this out whether we're broken or dying or otherwise. This is the end of the world as you know it that we are talking about. I wouldn't have had him do this if it hadn't been necessary, especially if I had known…" he stopped suddenly, casting his eyes away from Sam.

"What happened?" the hunter demanded, not liking the look on the angel's face or the way he hesitated. "Did something happen to Dean? Cas?"

The angel faced him again. "Our trap was not as secure as we thought. Alastair managed to free himself during the interrogation."

Icy coldness spread in Sam's stomach. He reached out and gripped the lapels of Castiel's trench coat, shaking him slightly. "What happened, Castiel? Is Dean…" he couldn't bring himself to say the word.

"He's still alive as far as we know," Castiel told him. "But he's been taken by Alastair and it is imperative that we find him as soon as possible." He barely blinked when Sam slammed him back against the wall, his hands trembling where they were still clutched in the coat.

"You're saying he's with the one person who could destroy him completely? When were you planning on telling me?"

Castiel gripped Sam's wrists and forced his hands to let go as he drew himself up to his full height, staring the young man down. "I'm here now, because I knew you would want to and deserved to know what happened, and also tell you that we are doing what we can to find him right now. Alastair seems to be concealing him from us. Now you will let me go if you wish your brother to be found before Alastair does too much damage to him."

"Wait a second," Sam growled, gripping Castiel's sleeve as he turned away, as if that would actually stop the angel from leaving if he wanted to, but thankfully Cas seemed to be willing to hear him out. "I'm going with you, or I will never let you see Dean again even if it means the world will come to an end, do you understand me? You got him into this mess, and I'm going to make sure you get him out."

Castiel glared at Sam so darkly that the younger Winchester actually took a step back. "You are experiencing high anxiety, so I will forgive your impudence. But I would prefer you show me some manner of respect since I am doing what I can to find your brother. If for no other reason than to practice when around the other angels who will not take such insults in stride."

Sam swallowed hard; more in fear of a refusal to let him come than of his own life coming over him. "Please," he said more quietly. "I can't just sit here and do nothing. Besides, if he is warded against angels, you might need a human to get him out."

Castiel was silent then nodded. "That is true. Besides, I know you will not rest until your brother is safe, so I shall let you come so you won't get in our way and impair the operation, but only if you agree to follow my orders."

Sam clenched his jaw but nodded, knowing he had no other choice. "Fine."

Castiel furrowed his brow, but seemed to see the hunter's conviction, because he nodded back once. "Then we have no time to waste."

Hope you liked the start :) I have a sort of prequel one-shot that goes along with this story that I hope to post later this week, and I hope you'll read it because it will give you more insight into Castiel's inner struggles. Please leave a review if you are so inclined :)