Fun game: After denying him an orgasm for a couple days (with chastity or otherwise), have him undresses for “inspection”. Upon making sure he’s properly groomed and clean, tell him to get hard for you.
Have your cane or whip ready.
Tell him to stroke himself and when you tell him to edge he should get to the edge and tell you when he’s there.
Tell him to “ride” the edge until you whip / cane him; then it’s hands off and a rest until you tel him to start again a few seconds later.
Keep going until he’s properly frustrated, properly whipped or both.
Then lock him up again and maybe have him “service” you.
Bonus points for pros if you can have him ruine an orgasm. Be ready to restrain his hands though if that happens, he won’t be able to make himself stop.