Even as hunters they were still a little bit different from the rest. Too far into the dark dealings of the things they fought. Now especially. Sam and Dean both had gone too far in to be counted as just a simple "lapse" of judgment on their parts. Dean knew what he was doing, not to an extent where he'd be some law firms superpowered bitch boy but to an extent where he was trying to keep his brother from turning into something he didn't want to become. It was an endless fear that rolled like an incoming storm inside him. What would happen if he failed? What would happen if Sammy was lost? The questions he knew his father asked himself up until he put that weight on his shoulders and died. There was no going back from that. No matter what spell was cast or deal was made -- the result would still be the same even if he wanted to say it wasn't. Winchester blood would always be spilled and there would always be one standing...feeling the guilt and the weight of the lives that had been lost.
It was heredity. He was sure of it. His father couldn't amount to the self hate that he pushed on them. Dean's own actions weren't dictated by what he wanted. They hadn't been since he was a kid. They were actions that were dictated by the mentality his father had slammed into his mind while he was growing up. Be the good soldier, fight the good fight. Up until your skin is falling off your bones and the blood was pooling at your feet and even then still fight. Keeping up with the fight would be the only thing to keep him from losing himself even though he didn't exactly know what he was fighting for anymore. His father? His brother? Both of them. Whatever it was, he knew it was for all the wrong reasons because it was always someone else he planned to die for. Not himself. He hadn't been told to think for himself; he hadn't been ordered to.
Sam didn't understand. He knew that he wouldn't understand because the younger Winchester just had the look about him whenever Dean spoke of giving up anything for the sake of his family. He'd breeze, a far distanced look in his eyes whenever Dean went on his spiel of how they were family and family needed to watch out for each other. Dean believed it. Believed that in the end they wouldn't get by without each other but they still were struggling to do so. The elder Winchester didn't want to tell his brother, what he had done in the name of keeping up his safety. He didn't know how Sam would look at him and he knew that he wouldn't understand it. He wasn't even sure if he understood it all that much when he was pressured into thinking that this was the only way. Even though the pressure only came from himself.
He didn't want to sell his brother out on the belief that he was going to go darkside. He needed to take the precautions that John had left up to him when he whispered those words to him. When he made him swear against everything he believed in that he would. There was no way that he could sit there and say that he wasn't afraid. That he was sure he'd have to go through those steps to ensure that his brother was still in the prime of his life. He didn't want his baby brother to die a monster. He didn't want him to have that hanging over his head even though he, himself, would have his hands caked in his blood at the end of every 'Sammy does darkside' scenario in his mind. The world they knew wouldn't end in flames. The only thing that would was him. Dean Winchester, despite being the "good guy" even though he was warped now. The hero of the story wasn't going to be him anymore. He knew that the moment he signed the papers and did the little monkey dance to give him a guarantee that everything will be put to the test to make sure Azazel's plans for Sam didn't pan out.