AJ, I suggest practicing with a banana. Peel it, and shove it down your throat as far as you can. Keep doing it until you can do it over and over (and over) without puking. You will loose a lot of weight in jail, if you do not get rid of your gag reflex right away. And stretch your anus every chance you get. The bigger the better. It will probably still get torn and ripped from the force of repeated penetration, but the stretching will definitely help ease the pain.