What do you say when your partner says, “I'll do anything if you will just let me cum!”? Try saying something like this:
- “Go masturbate on the front porch.”
- “Stand naked in the middle of the back yard and masturbate.”
- “Go masturbate on the neighbor's porch.”
- “Stand in the middle of the highway and masturbate.”
- “Masturbate in the neighbor's coy pond.”
If he doesn't want to do it, then tell him that he doesn't really need to cum, yet. Tell him he has an extra week in chastity just for asking. Or give him a choice, do what you asked or spend another week in chastity. The point here is, he doesn't “need” an orgasm. If he wants one badly enough, perhaps he will do as you requested.
- “Call Bob and ask him if he wants a blow-job. Give him one and I'll let you cum.”
- “Let your friend Steve fuck me and I'll let you cum.”
- “Text your mother a photo of your genitals and maybe I'll let you cum.”
- “Knock on Old Lady Simpsons door and ask her to give you a blow job.”
- “Ask me again and I will flush key down the toilet.”
Or simply offer to remove his chastity device and never replace it... And he will never get any kind of sex from you again. You see, it is all a game. How you play the game is what matters. As long as you are teasing him, frequently, then he has nothing to complain about. But if you ignore him, it is no longer a game that you are both playing. It's like playing poker by yourself. It's just not fun any more. So remember to tease him as often as you can, find reasons to move his release date back a few days (even if it is only because you want to) so that he will never quite reach that date. Ruin and orgasm of two, or milk his prostate and tell him that's is for the month.
My point is, it is up to you to keep the game going and to keep him aroused and denied. Once you allow him that nice, full orgasm, you have to start the game all over again. And just when he was doing so well, too.