[Only first he'll need to change. It'd be weird to sleep in his clothes when this is his place, but it's weirder still to get changed with her in the room. It shouldn't be, she's seen more than this, but it still makes him uneasy — not enough to retreat to the bathroom, but enough to keep his eyes on the floor and the closet door open. It gives him some shelter, even if it's not perfect. Don't look, Kitty.
He undresses quickly, unraveling the tie with a silky swoosh before making short work of the buttons in his shirt, and despite knowing fully well that he's a boy he doesn't leave himself uncovered for long. T-shirt, and then the pants are next to go which is awkward and noisy but thankfully they require enough focus that he doesn't think about it too hard. Pajama pants and then he's all set.
He closes the door. Fidgets a little. This is so far from the first time they sleep together, but it's still awkward. At least for him.]