The idea that orgasms are not free is a nice way to add an element of fun to the forced chastity experience. For example, if a keyholder wants to train her male to quickly ejaculate when told, she can release him from his cage, then before letting him touch himself, she can set a timer; say for one minute. He must ejaculate before the timer runs out. If he doesn’t, he is locked back up until next time. By shortening the time he gets to squirt, he can be trained to become efficient for his keyholder.
Earning an orgasm is also a nice keyholder entertainment. Some “prices” are not voluntary. The keyholder may require the male to always eat the product of his orgasm. He doesn’t get to choose to come or not. Another post-orgasm activity is for the keyholder to vigorously rub the head of the penis immediately after orgasm. You may need to tie him down for this one. Earning an orgasm by consistently doing chores is also a nice way to integrate chastity into daily life. I would suggest that he not earn an orgasm by providing you, the keyholder, with pleasure. That’s his job and his joy. He doesn’t need a reward for that.
Games of chance are also entertaining. One could be as simple as a dice game. If he rolls a certain number or above, he gets to come. Of course before he rolls the dice, he should be stimulated right up to the edge. That way, if he misses the target, he gets stimulated to the edge again and has to try again. He will never know when you will decide he doesn’t get another chance and has to go back in his cage. A variant of this is to use the roll of dice to determine the timer setting for his masturbation. In that case, he gets no warmup. So if you are using two dice, maybe multiply the number rolled by five. So if he gets a twelve, he has sixty seconds. Poor boy that rolls snake eyes. You could play blackjack. You are the “house”. If he wins, he gets ten seconds of masturbation, then the next hand. If he hasn’t come and you get tired of the game, lock him up without his squirt.
This is all meant to provide a playful way to provide him with release without making it dull or routine. Solo caged males often use games like this, and sometimes chores to determine when they can play with themselves. Many keyholders find earning orgasm and sex games as an amusing part of forced male chastity.