If you've completely taken the bottles away, I'd say to not give him one again. He'll not become mannourished w/in the time period that it'll take for him to become accustomed to taking it from some kind of cup. It sounds to me as if he already realizes that you'll do just about anything to get him to take milk (buying all kinds of cups, trying to slowly transition him, etc), and he's having fun with manipulating you! Some kids have this tendency innately -- especially if their mama is a 'pleaser' (Phlegmatic temperament person, as it sounds as if you are. I'm NOT! LOL I'm partly a 'choleric' - domineering, powerful personality!)
Quit making such a big deal of it. Just give him yogurt or cheese until he decides that he'd like to drink some milk from some cup. Let him tell you which cup and when he wants it. Give him water and/or juice or whatever healthy liquid he'll consume until he gets bored with trying to 'pull your strings'.
On the other hand, I nursed all 4 of our kids, and the 2 boys both nursed for 15-18 months (girls were pretty much done at a year). As long as they'll sit or lay still and DRINK it -- not walk around with it as their 'side-kick' -- they may still need to nurse for their healthy emotional development.