Be Careful What You Wish For
Ask him to tell you the names of three women in his life who he would love the most to "come out" to about his chastity...
After he has been denied his orgasm for a few months and is so desperate he is nearly out of his mind, restrain him. Blindfold him. Gag him. Tease him for as long as you want. Tickle his nipples. Stroke his balls. Make him so hard inside his cage that pain radiates up into his belly and he's begging for mercy.
Then, remove his chastity and tease him mercilessly for another good long time, but never let him cum. After he is whimpering, begging, in tears, drooling uncontrollably al over himself and dripping in miserable sexual frustration, tell him that you will allow him to cum -- under one condition.
He's gagged, so he won't be able to speak to ask you any questions, but tell him that the only way you'll allow him relief is to agree to your terms. Warn him that once he agrees, there is no turning back; if he reneges on his agreement, then he gets a suitable number of slaps in the balls and then gets locked back in chastity with no relief. If he chooses to decline your terms, then he gets to spend another few days/weeks/months in his cage with no release, just with no slaps.
If he agrees (and he probably will), tell him that you will unlock one of his hands so he can finish himself off, but he's not allowed to touch himself until you say. Also, remind him of the consequences if he refuses once he's agreed.
Unlock his hand. Tell him to grasp his cock, but tell him he is NOT allowed to stroke. He must remain perfectly still or there will be consequences.
Once his hand is in place, remove his blindfold.....
....which is when he will realize that the three women he named have been sitting there watching the whole time, and the only way he's allowed to cum now is by jerking off while they watch.
