Hello lovely people. So this idea came to me and wouldn't let go. I was planning on waiting to start it for a while and finish off some of my other stories. But, I didn't so here you are. I hope you like it.

Disclaimer: I don't own Supernatural.

Castiel Novak had wanted only one thing in his life. He wanted to fly. And so at the tender age of 18 he joined the United States Air Force where they paid for him to study at university so he could become a fighter pilot. Which he succeeded in doing, gaining the call sign Angel. He in fact became one of the best there was, with his natural ability to feel at one with whatever aircraft they placed him in. Everyone said he would go far, or well they did until he opened his mouth. See while Castiel could fly like no other, he was rather socially awkward (and by socially awkward I mean he said whatever he was thinking and screw the consequences). As such he only made it to major before he was forced to retire from flying and become an instructor. Oh he could and would still fly, he just couldn't do the dog fighting. He only lasted a year of training the new generation before he could hack it no more. He hated having to sit on the side-lines while the people he trained went and risked their lives for his country. And so it was with that that Angel hung up his wings. Or at least the Air Force ones.

So Castiel returned home only to be confronted by his brother looking for his latest project. See Gabriel Novak collected companies and businesses like most people collected dvd's (not that Castiel knew this). He had a whole portfolio of them and as of yet not one of them had ever failed (though whether that was down to him or the shit hot teams he employed to run them was debatable). So anyway Gabriel claimed he was looking for something to do, and Castiel was the perfect solution to his boredom. And so was born Heavenly Wings Flight Training Company.

And of course the true reason for Gabriel's involvement was not because he knew his brother would refuse to take a cent from him, even if he did tell him that he was a millionaire (honest). So instead Gabriel created work for his brother that involved flying and thus making Castiel's world better. What he hadn't taken account of, of course, was that his brother would not be just flying the planes, he would be training the people too. Which meant he would have to communicate with them. Which might not have been the best idea he had ever had.

Dean Winchester also only wanted one thing in his life, and that was for his little brother Sam to be happy. They'd had a pretty crappy childhood with their mother dying when Sam was still a baby and their father having to travel around the country for work before dying when they were young too. They spent most of their time with their 'Uncle' Bobby, who was in fact their fathers best friend and had taken them in in an attempt to give them some sort of stable home life. It was there that Dean learnt to work on cars. And he was amazing at it. By the age of 14 he was in Bobby's scrap yard fixing up all the broken cars he could find. Once fixed he and Bobby sold them, Dean keeping the profits and saving them. It was with these savings that he managed at the age 25 buy his own auto-body shop. Dean never went to college, no that was Sammy's thing. But he could fix anything you asked him too.

He was proud of his little brother. He had become a great lawyer and returned to their home town to practice, bringing with him his college girlfriend who was now his fiancée and soon to be his wife. And this is the point our story begins, because as much as Dean loved Jess and thought she was great for his brother he did not agree with all her ideas. Namely the one in which said that getting married on the beach in Hawaii would be soooo romantic. Because Dean Winchester did not fly. Ever. Period. Not going to happen.