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Harry doesn't cry often, he had learnt at a young age that allowing the tears to fall and showing someone he was hurting was just a way of inviting more pain to himself.
But, despite what some people had thought, just because he didn't allow people to see his tears didn't mean he didn't cry at all, it didn't mean he didn't want to.
While others could break down and allow themselves the escape of their own sadness, Harry didn't have such a luxury. Harry had to be everything that was expected of him for a hidden world that only wanted him if he was useful in their plans. Harry had long since grown accustomed to harsh words and bitter glares and the wizarding world, for all its wonder and magic, was no different from the one he left when he was eleven. He no longer allowed the words to hurt him as badly as they once had, that isn't to say they didn't hurt him, because they did, but he knew that if he allowed himself to pause and listen to what the whisperers said it could only be worse.
It was only when he met a demon king that he allowed himself to be weak.
He knew that it was okay to lose himself in his sadness and cry for what he had lost and what he had never had the chance to have. He cried for his loss and he cried for what could have been, he cried for his friends and he cried for the family he never had the chance to be raised by, he cried for the war and he cried for what it had cost.
Crowley allowed him to break, no one should have had to be so strong for such a long time in an attempt to please others. For a demon that found himself being summoned by person after person after person to grant their wishes and push them to amazing success and positions of power, it was an urge he was sure he would fall in to and lose himself to, if it weren't for the fact that he didn't feel emotions like humans did, if he felt anything at all. When he looked at the green eyed wizard he felt a smile tug at his lips even ad he watched him fall apart, if being human was the warmth he thought he felt when he looked at Harry then he was sure that it was something he could get used too, no matter how inconvenient.
When the king of hell looked at Harry he thought he would gladly embrace all parts of human emotion even if he would break apart, he would gladly cry for his love. He would all too willingly, for a demon with a sense of self preservation like he had, allow himslef to be lost like he was when he was human.
Crowley may have known that crying achieved nothing and would not help him with anything, he knew he would still be the king of hell and Harry would still have been cast aside like a broken and unwanted toy by the wizarding world.
But he would try, for Harry he would try.
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