Can an enemy fall asleep in your arms?
When you shoot an ennemy with the Wu Silent Pistol or the Mk-22, he falls asleep after a short time (except for headshots).
What happens if you shoot an enemy, and grab him before he passes out ?
Solution 1:
I can only answer for Peace Walker, but if you tranq a enemy before CQC holding him, he can fall asleep on you, you'll automatically let him go.
Solution 2:
In MGS 5, this can happen with Quiet as buddy.
If you're grabbing an enemy right before Quiet shoots him, Snake will let that enemy go. This has happened to me with both lethal and non-lethal Quiet, so whether they sleep or die, Snake will let go of them in any case.