Castiel whimpers as Sam just barely presses in, because it's borderline uncomfortable - but not quite there, they've done this often enough that Castiel knows how to relax for this little push, this barely-there-breach.

If anything, it makes him want more.

"Yes. I'm up for this, Sam. Please."

Always. It's been too long since he's felt Sam, though he deserved the long break in their intimacy.