How Should a Keyholder Approach it?
This is one place where the Internet seems to get it wrong. They seem to think that you, as the Keyholder should make all the rules, and be as mean and evil as you can possibly be. Go ahead and try that approach. I'll wait...
I didn't think it would take long for you realize that that is the WRONG approach. I will admit, there are a few men out there who would relish that type of a Keyholder. If that is what he really wants, then by all means, give it to him.
I will admit, many times the “Dream” of a guy who wants to try chastity, is quite often of a Keyholder ( a woman) that is mean and cruel and won't give him and inch, much less an orgasm... EVER! But faced with reality, most men will back off from that kind of relationship. It just won't work for them. I agree. It won't work for most men. And I don't think most wives or girlfriends, for that matter, could be that mean and cruel.
It would be better to start out nice and easy. Take things slowly. You may find some things that you like and you can include them in your regular activities. You may find some that just don't fit what you (or he) had in mind. There is one area in which you should be strong-willed, stubborn, hard-headed about, and that is not giving in when the pleading starts. Yes, there will be pleading. But whatever rules you have starting out concerning ejaculations and how often they should be allowed, you need to stick to them. If you said one a week for the first month and then “we will see” for the time after that, be sure to allow him one ejaculation per week (for that first month).
Having said that, there is something you should commit to memory right now... NEVER say you can have an orgasm on this day or that day. NEVER be definite about that day. Instead, what you want to do is to promise him that he can have a “chance for an orgasm,” or “a chance for an ejaculation.” Putting it that way, opens up the door for you to extend his lack of ejaculations for as long as you would like. Maybe indefinitely!?
Now, repeat after me, “I am giving you a chance to ejaculate today.” Very good. Why are you not allowed to say, “I am granting you an orgasm today?” Because, unless, for some strange reason, you have decided that it IS time to allow him to ejaculate, you don't want him to. But you want him to think that he has a CHANCE to cum! You can play a game, or give him a task to perform, or a time limit, or just about anything you can think of that will make it almost impossible for him to achieve his goal.
One last thing... Before you begin this journey into male chastity, you should sit down and talk with your partner and discuss things like release dates, amount of teasing he is to get, and limits. Limits are something that your partner (or you) flatly refuse to do. There may be a lot of them, but you should know what they are before you begin. Also, you will need a method of signaling that something “new” falls under a limit he had not thought of. Remember, safety first!
Have fun and remember the word, “Chance!”