probable misrepresentation of how airports work
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Cas has a problem. He's becoming more human every day, and he's worried Dean won't have much use for him without his powers. He's been savoring every road trip he's taken with the Winchesters over the last month, because the only time he's been able to get a decent night's sleep has been when he's forced to share a bed with Dean.
Dean has a problem too. Since Cas told Heaven to suck it and moved into the bunker, he's grown more and more accustomed to the nights (way to few and far between) when he's had to share a crappy motel bed with Cas. It's gotten to the point where he looks forward to lumpy mattresses more than sleeping on his own memory foam if it means he's got an excuse to share with Cas.
Luckily for both of them, Jerry Panowski's got a problem too... only looking into his problem means spending some quality time at an airport Dean doesn't have the fondest memories of. At least he'll get to spend a few more nights sharing Cas's bed before he has a long overdue talk with his best friend.
Dean can't decide which he's more terrified of-- airplanes or confessing his feelings to Cas.