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The first time he knew the angel would be a pain in his ass would probably have to be when he appeared in the motel room in the middle of the night. When the hunter had startled awake from a nightmare and the bastard asked him what he was dreaming about. Naturally he was not going to answer, and if he did, he would not give him an honest one. Why should he?
Though something in Castiel's expression told him that the angel already knew. He had touched Dean's soul after all, he knew every inch of the hunter and that terrified him a little. To know that someone knew everything he kept hidden from the world. His fears, his regrets…everything. Especially everything from hell.
He kept the conversation short and quick, but it still bothered him after that, rolling in his mind. Wondering how much of his dreams the angel knew about. If he knew how Dean dreamt of being on the rack again…
How he dreamed of holding the knife and slicing into another soul. Listening to Alastair's praise being whispered in his ears as the demon held him. Just dredging up the memory had him shuddering and Sam sending him questioning glances. He did not like thinking about how tender the demon had been with him when he came off the rack and took up the knife.
How he had been treated more like a lover than a pet.
And in a way he was thankful for the angel clearing his mind of dreams that night so he could sleep peacefully.
It had been the best nights sleep he had had since his return from hell.
A return that he wished had not been done. There were so many souls who deserved saving more than his.
But somehow God saw his worthy enough of sending an angel to pull him from the darkest depths of hell.
An angel who saw into his soul, who saw someone that deserved to be saved, and gave him a second chance.
Somehow despite how hard he would fight with the angel, Castiel still fought for him. By his side every step of the way. It infuriated and surprised him. He had never thought of himself as someone worth fighting for, and every time someone he loved died for him he felt a piece of himself slip away.
But still Castiel kept fighting for and with him. Trying to prove something.
And still Dean kept pushing him away, shoving his love back at him, trying to maintain his barriers. Because he was a hunter. An animal. A monster. Something unnatural. He should not even be alive. It was because of him so many people died.
In no way was he worth fighting for.
Yet Castiel still tried. He died time after time, and was brought back, still moving to the hunter's side and trying to put the pieces of Dean's broken soul back together.
Every damn time.
Somehow that hurt more than the sad looks Sam would give him, or the looks from Bobby. It shattered him more than even knowing those who had died fighting for him, or how he could not save Adam.
Because no matter how bad he treated this angel, how many times he kicked him down, told him off. How many times he shoved his words in his face, or treated him like shit.
No matter how many names he called him.
He still came back.
In a way it was funny.
His Mother always said 'angels are watching over you'. He thought it was just something stupid, that they did not exist. If they did, why would they take her away from him?
And now he knew why…
Because in exchange, even if it was almost too late…
They gave him his own guardian angel.