Fear of Flying (well if you can call it flying)

Sam had never understood where Dean's profound fear of flying came from. When did his fearless, older brother have the chance to develop this odd phobia? His brother wasn't afraid of anything; Dean fought demons, werewolves, vampires, angels, hell even Lucifer himself on a daily basis without flinching and yet the idea of sitting on an aeroplane for a couple of hours could make him go weak at the knees. Sam comprehended the idea of being afraid of things others found trivial and even humorous. Clowns, to him, were terrifying but most people loved them, cheered for them and travelled miles to see them at a circus. However, Sam was fully aware of where his fear of clowns came from, Plucky Pennywhistle's Magical Menagerie. All those nights Dean had abandoned him in the chain pizzerias to care for himself, while fending off creepy clowns and trying to keep down inedible cardboard that they called 'pizza' the phobia slowly crept its way into the subconscious of Sam's child mind.

But Dean had no reason for being afraid of flying. They've only travelled by aeroplane on a handful of occasions (and granted they weren't the best experiences, what with the whole demonic possession or post freeing Lucifer, but Dean's fear developed prior to these events); they always used the impala if they wanted to go anywhere, or another stolen vehicle, so when did this fear have a chance to manifest. Sure, he may have watched scary movies about plane crashes as a kid, but that wouldn't have caused the intense anxiety he felt when encountering planes. So what did?

This was a question Sam asked many times, and every time he had received a response along the lines of "Drop it, Sammy," or "Well, at least I'm not terrified of a bit of face and a rubber nose!" and on rare occasions a flustered Dean babbling endlessly about films such as 'Snakes on a Plane' and once even 'Airplane' claiming, "Only bad things happen on planes, Sam. There has never been a movie about a plane where nothing has gone wrong!" All these responses simply irritated Sam and gave him no useful information about the origin of the fear itself. So, like anyone would do, Sam had abandoned all hope of getting a straight forward answer a long time ago.

Giving up, however, did not mean that Sam had stopped thinking about the various possibilities that would explain the origin of Dean's irrational fear, spending hours concocting elaborate stories within his head. On the rare occasions Sam did sleep and he wasn't having nightmares, Sam would dream about the possibilities testing there credibility and whether or not they were realistic or not, of course most of them had made no sense(they were dreams, how often has your dreams made any sense) and wouldn't explain Dean's fear of flying but they did make Sam question why Dean wasn't afraid of pretty much everything after thinking about the things they had both seen during their lifetimes. Each possibility Sam thought of was more insane than the last, ranging from talking aeroplanes to demon flight attendant babysitters.

Despite all the possible reasons Sam had thought of over the years, none of his ridiculous and irrational theories had prepared him for when he found out the truth, the answer he had been anticipating for over a decade. This long overdue answer didn't make any sense what so ever to Sam, it probably didn't make sense to anyone except Dean and possibly four other people on the planet. It wasn't movies, it wasn't tales or documentaries he had seen, or heard, about planes breaking and crashing to the ground, it wasn't the motion of flying, it wasn't even aeroplanes themselves that Dean were afraid of. No, Dean developed this irrational fear all because of a madman. A madman with a box.