It's one of those 4am's when I just sit up and have to write something, no matter how crappy and fluffy it is. Well, I had fun writing it. Hopefully you'll have fun reading it, tell me what you think! :) x
There are so many ways to how this could have happened.
Dean could have actually passed that note to Cas during History, the one where he wrote 'wanna go see a movie today? x' instead of the one that said just 'wanna go see a movie today?' and it would have made Cas blush a little because oh my god Dean just signed the note with a kiss what does that mean do you think he likes me why are you laughing at me Gabriel you are not helping! And Dean would have blushed a little too because he knows Cas always over thinks everything and yeah, it means that he likes him. Yes, Sam, like that!
It didn't happen like that though, because Dean knows Cas over thinks everything but he doesn't know that Cas likes him like that too.
It could have happened in that party at Jo's house when they were all sitting in a circle in the basement, playing spin the bottle and if that bottle would have moved just a little bit more to the right and landed on Dean instead of Meg, and Cas would've kissed Dean, his best friend, not Meg, the bitch from Biology whose lips taste like cigarette smoke and too much cherry lipstick that doesn't actually taste like cherry. Cas would've found out then that kissing Dean tastes like beer (well, maybe that had to do with the party) and cherry pie, that does actually taste like cherry.
But it doesn't, because Meg stops it with her magic evil powers, or at least that's what Dean likes to think.
Maybe it could have happened that night when they were drinking strawberry milkshakes on the hood of Dean's Impala at the shore of the lake that's only 8 minutes away from their houses, if John hadn't called when they were just starting to lean in towards each other, and screamed at Dean for not being home to watch over Sammy, even though he's a big boy, he's 14 dad, he doesn't need me to watch over him all the time and Dean wouldn't have had to apologize awkwardly and drive Cas home while blasting AC/DC to avoid any uncomfortable silence and they would have actually closed the gap between them and made out on the hood on the Impala until Cas would have accidentally spilled his milkshake and Dean would have thought for a minute it was something else and it would have been kinda awkward but then they would have started laughing really hard.
Nothing like that happens though, because of John and his stupid rules and the stupid bar he goes to every freaking Tuesday (and Wednesday, Thursday, Friday, Saturday, Sunday and Monday) night, leaving Dean alone with Sam.
And it could have happened that time Cas came over to Dean's house shaking uncontrollably, because his father, after being missing for over ten years, was found dead this morning, and even though Cas hated the man for leaving him and his siblings alone like that, his death still came as a shock and Dean held Cas in his arms and comforted him and if he would have just lowered his head slightly and turned it to the left, his lips would have touched Cas' and they would have been kissing.
They don't though; because Cas had a rough day and Dean's scared he'll upset him even more.
It does happen two days after high school's over, and Dean and Cas are in Dean's rooms, just laughing and talking about everything and nothing. Cas makes a joke and Dean thinks fuck, I'm so in love with you and leans in to kiss Cas, and although for a moment Cas is shocked he kisses back with everything he has, and when they pull back, gasping for air and Cas is on top of Dean, who is lying down on his bed, they start laughing because it took them so damn long, but hey, at least it finally happened!