On the whole idea of waking him up with a blowjob, we have never tried this before. I am not really sure how it would really work, but I guess we could always experiment and find out huh? He's a deep sleeper, so I don't even know if he would even wake up haha.
I would never try something sexual with someone who was sleeping, and if someone did it to me, I would fuck them up. It makes me super uncomfortable. If we talked about it beforehand, and it was something they really really wanted, then I would MAYBE do it. But otherwise, it just doesn't seem like a good way to make sure that what's happening is consensual.