Well... as a Domme, I'm gonna go with, NO. Granted, I'm female, and if I perform anal sex on my male sub, well... obviously the "penis" in question is not actually going to cum. I absolutely love that Wellbehaved likes to be humilitated if that's what I so desire-but I don't think I'd want to go that far. I don't think he'd like that particular act either.
And as far as I'm concerned-he's the perfect sub for me!
But like many have said, to each his own.