Patty's Tutorial on How to Train a Man
For the ultimate in feminization, emasculation, and humiliation, I suggest you train your sub to suck off other men on a regular basis.
After all you've put him through already, it's the next logical step, girls. And in my experience, at this point, he won't offer any resistance at all.
You can start with transvestites at a cheap bar, and progress to places like washrooms in public parks and glory-holes in pornographic bookstores.
Put the icing on the humiliation cake for him by calling him a "good little cock-sucking whore" and encouraging him to "swallow every last drop of the spunk" he milks out of the guy's dick with his lips and tongue.
(You'd like to suck this tranny cock for me, wouldn't you, jerk-off? -Admit it. Think about sucking cock and swallowing huge mouthfuls of splooge as you slowly stroke your dick right to the edge for me.)