I've had no experience with this, but I've thought about it. Im usually a top, but my mind has delved into the realm of orgasm denial/chastity for myself. Here's what I came up with:
Be slow, but firm. Make him realize that his orgasms are now yours to give out as you like. This means he cannot touch his cock or balls except to wash them. Push him to new boundaries, but realize everybody is different in how they respond to pushing, so you're going to have to gauge it. If he likes to be challenged, maybe start with a few days of constant teasing, but no orgasm. If he doesn't like too much of a challenge, make it one or two days. Make the orgasm enjoyable, because that's what he'll crave.
Now, and this is just me, maybe try to have him connect the idea of an orgasm with the act of being a good sub. The better a sub he is, the more likely it is for him to get an orgasm. This should almost be the premise of the chastity: If you're good, and you're always good, you might get an orgasm. You need to enforce this at all times.
But don't jump into weeks of chastity and denial right away. For some men this may work, but I doubt it'd work on all men. If it were me, I'd get aggressive and tactful. After you give him his first orgasm while in training, do something like "Now in order to earn your next one, you must clean the whole house" or something like that. I'm not sure what your dynamic is, but try something like that. Make him do something to earn it. And knowing guys, he'll probably do it right away. If he does, tell him "I never said that it'd happen right away. The house is going to be clean the next time you cum." Choice of words is key here. Notice how the house is going to be clean the next time he cums. It doesn't matter if it's in an hour or three days. He will keep the house clean.
Tease him constantly for about a week, but then lay off it. No person, male or female, can stand being 100% horny all the time. He needs to live his life, and just make sure you can incorporate that.
By the time he gets to going 3 weeks per orgasm (all of these should be fulfilling and enjoyable orgasms), start milking him. There's tons of literature on it, and I'm not confident on it, but yeah.
Up until now he should not have touched his penis in quite a while. You may have, but I hope he hasn't. And now that he's started to be milked and understands the frustration of not being able to cum, now he should experience not being allowed to cum. I'm not too sure on this part, but it's teasing and getting him to hold his orgasm as long as possible before going back to "sorry, no more for tonight."
Hope this helps, keep us updated!
