It took a long time for Dean to settle in. The introductory sessions hosted for all the freshman were ditched until Cas made him stay for fear of being by himself. They stuck together like glue, riding out the social pariah, getting curious glances and giving them at the same time. The summertime heat had Dean ditching his jacket and walking around in just a button up and jeans with Cas, in his usual faded t-shirt and jeans. Boots and sneakers - they were rarely seen without the other.
Castiel was from a city thirty miles away where no one knew anyone else, only who they went to church with and who they saw at school. All his life his folks worked two jobs each trying to support their small family, but when his sister died in a car accident his mother went into a deep depression. They went bankrupt. His father worked his fingers to the bone and Cas applied for all the scholarships he could handle, pushed by his dad to succeed so he didn't ever have to struggle like they were struggling. He confessed to never having many friends but having a good experience in school for the most part. Before they went bankrupt, they'd had plenty of kids over at one time - mostly friends of friends, but they'd all hang out together sometimes. Most days he was alone - drawing, as Dean came to find out. But afterwards everything seem to fall apart. Everything became hard to come by. He'd had to get a job to help his dad pay for bills. Through that, he had managed to keep his grades pretty damn far up, but he wasn't perfect. No one was. That kind of stress took its toll. Plus, Cas had only barely hinted his last two years of high school had been hell. What he meant by that Dean hadn't found out yet, but he wasn't asking. When the kid was ready he'd fess up.
Dean told him about the traveling. Said his dad was in pest control, their mom died when they were young and he'd been taking care of his little brother Sam ever since. He explained his friction with Sam, how their dad felt when he wanted to leave. Cas and him talked long into the night, Dean on borrowed sheets covered in baseballs, both of them staring at the ceiling and talking about their lives. Dean told Cas... everything. Almost everything. He left out the murdering demons and ghosts part. But he was finally, finally comfortable with someone. He had found a friend in all his mess of a life - something he hadn't thought was possible. Stuck at school, like he had always feared, was demanding and would get worse when classes started, but finding Cas made it all so much easier. He'd just go back to the room and find him there, pastels (not giant crayons) smeared on his face and hands, his eyes bright with worry as he looked up from his sketchbook, long legs crossed on his bed. He'd unload and Cas would sort through it all and, piece by piece, acknowledge and smooth away his worries and fears.
Little did he know, he was climbing Dean's dam of emotions. What, Dean wondered, what he think if he found the other side? It scared him to think of losing his first real friend outside his family. But... at the same time... He knew it would never end like that.