You weren’t a trusting person. It was a thing, that you’d grown up in an environment where you couldn’t trust anyone but your family, and it’d taken a damn long time for you to trust Sam and Dean considering you lost your family. God, he got that, he understood all of how you didn’t feel like you could trust anyone but those close to you, so he’d taken it in baby steps. First it was pouring a beer out in front of you so you’d know it wasn’t roofied. Then it was showing you your room in a motel or in the bunker so you’d feel safe. Checking the locks with you. He was willing to do all that, cause he had all those habits when he took care of Sammy.

It was work, sure, but it was work he was willing to do, considering how he knew what you felt, he understood it, since he wasn’t one either, so he could relate. It’d become second nature to let you know everything, and now he was one of the only people you trusted.

That’s more than fucking ideal.

“A cold one.” He chuckled, sitting down next to you in your shared shitty motel room, opening a bottle so you’d hear the fizz— he’d safety checked it beforehand. Just so you’re comfortable— no, he wasn’t bitchin’. He wasn’t a little bitch, you needed the reassurance.

Again, he was happy to help.

Dean passed the beer to you, stroking your hair once, since it’d always helped in soothing you to entertain what he was putting out for you. Your old man was one sick bastard for training you like that. “D’you want it, sweetheart?” If not, that’s ok.

Did he know what he was doing? No. He didn’t exactly get training on how to deal with women, with Sammy he could just say ‘go get laid’ if he was being a prissy ass. But with you, he didn’t push anything, you were in control, which wasn’t such a bad thing.

That sounded more sexual than intended.