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When Castiel first entered the barn, Dean was a little scared. He didn't know what he was and the bullets Bobby and him shot through him didn't even make him flinch. He was also intrigued by this handsome man who didn't look like much of anything in terms of power, especially with this trench coat he was wearing. Dean couldn't help but be a little aroused by the way the stranger at the time simply removed the knife from his chest and let it fall to the floor. Their first meeting was still a great memory for Dean. He knew nothing about Castiel and he had trouble believing anything he was saying, but there was already something between them. The way they talked and looked at each other, the way the angel read him, "You don't think you deserve to be saved". Dean never could've imagined their relationship becoming what it was now, but reliving their first encounter, he could see the base for their profound bond was there right from the start.
Sam couldn't believe his brother was gone. It had happened so fast. Sam had ran but it was no use, by the time he got to him, Dean was already dead. All that was left of him was the lifeless body of a man who'd spent his years saving and protecting people, most of all his little brother for whom he would and did give up his life. Sam was holding his brother's body, tears streaming down his face, taken by overwhelming sobs.
After a while, Sam calmed. He took his heavy brother in his arms and carried him to the impala. He laid him on the back seat and started driving. He didn't know what to do, how to deal with this loss, and he stopped several times on the way to summon a crossroad demon, trying to work out some sort of deal, but it was useless. He spent the entire two-day drive home struggling to figure out a solution, some way to reverse this, to make it go away. But when he parked in the bunker's garage, Dean was still lying dead in his baby. Sam left his brother in the impala and went to the library to call Castiel. When the angel appeared, he immediately saw the grief in the hunter's eyes.
"What's wrong?"
"It's..."
Sam swallowed. A few tears escaped down his cheek. He couldn't bring himself to say the words.
"It's Dean. He's..." He made sure to look directly into Castiel's eyes before continuing, so he'd know it was real. "Cas, he's dead. The monster we were hunting killed him. I couldn't get to him on time."
Both men stayed like this for a long time. Staring into each other's eyes, letting out a sob every now and then. None of them wanted to face reality. Sam knew he had a life to get back to, the monster who killed his brother was still out there and he needed to go back and slay it, but then what? For the moment, he just wanted to stay there and feel the pain.
Dean often complained about Castiel being in his personal space and suddenly appearing right behind him, but, truth is, he actually liked that. The proximity was nice and he felt safe with the angel standing close. Which made no sense. Dean was a hunter, a great one at it too, and he didn't need anybody's protection, except there was something comforting about not being alone. Dean had a great time going after Raphael with Cas. The angel was so ignorant of human customs, like lying, and it was kind of adorable when he presented his fake badge upside down. Of course, the hunter couldn't help looking up in exasperation every time Castiel did or said something that exposed his lack of social skills, but it was one of the things he appreciated of the angel. He was an old and powerful being, but there was this child-like innocence to him that warmed Dean's heart. When Castiel told Raphael "you're my little bitch", Dean was so impressed and taken aback he temporarily lost the ability to form a sentence. That night was when Dean first realized he was falling in love with the angel.
They burned the body that night, gave him a traditional hunter's funeral. After all the crap he had endured, Dean more than earned his peaceful rest, he deserved it. He had died doing his job, like many before him, and Sam couldn't help but wish the world would know about Dean. About how he gave his soul and suffered hell for a little brother who didn't bother looking for him when he ended up in purgatory years later after he saved everyone from the leviathans. How he gave up everything to avert the apocalypse, how he let go of a normal happy life to get back into the hunter life, how he never even had a childhood because he was taking care of a brother who abandoned him for a better life, how he was always loyal to a father who never found him good enough, how he spent his entire life thinking he was worthless when he sacrificed everything to save people, how after all the good he did he couldn't believe an angel would rescue him from hell. How he lost everyone he cared about and still kept getting up in the morning to save other people's friends and family. Yes, losing Dean hurt Sam, but he knew his brother had accomplished his purpose and the best way to honour him was to let him go.
Dean was in the Roadhouse playing pool with Jo and she was kicking his ass, Ash thought it was hilarious. Bobby and Ellen were casually holding hands over the bar, deep in conversation with Pam. They were a big happy family and Dean couldn't have asked for a better way to spend eternity. His mother wasn't there, but with the help of Ash, he was able to visit her every once in a while. It was peaceful and it was a relief after the life he'd led. Dean never hoped for anything more than this, but he got it anyway. Cas materialised before him and kissed him before the former hunter even had time to say hello. The angel promised to never abandon him and to visit every day. And then, Dean's Heaven was complete.