Last night was his closest he has come to winning.
By now he has figured out that if his dick is hard he will lose. Of course, I do my best, after his CB-2000 is off and we put a fresh pair of royal blue boxers on, to make sure his dick gets very hard by undressing slowly and sensually in a way that really pushes his buttons. I can almost hear him moaning when I do this. Last night he was trying desperately to look at the floor when I undressed.
In any case, the men out there who have actually gone two weeks without release know that an erection is followed very quickly by pre-cum. And guys who are wearing chastity devices 24/7 generally pop a boner as soon as you let them out. Plus, when your device does not let you become erect, just having an erection is intense pleasure.