He's grateful, if he thinks about it, that there's already a sort of pattern laid out for this. He's never doubted that Crowley trusted him, but the rare moments when the demon shows it are nearly always the times when it's both of them together.

(This really is meant to be all about you.)

He feels so unprepared.

But Crowley is slowly relaxing - or at least is less actively fighting him - and this intense, solo focus slowly begins to feel less foreign. He uses a light touch across what he can reach of the soft underside of the wing, here working deeper into tense muscles, combing his fingers over and over through long, long feathers at the wingtip, and here the short, downy ones closer to the shoulder. It would be easy to lose himself in it if he wasn't focussed so intently on Crowley's reactions.