Hi. We are a married couple in our late twenties. My husband and I love the game of tease and denial, that is I decide when he can orgasm. He always wanted to be put in a chastity belt so finally I got him one to wear a few months back. Initially he wore it off and on for a few weeks with him holding the key. Finally about 3 months back he handed over the key to me and I now wear it around my neck in plain sight of him.
Although it was consensual there were periods when it was very hard for my husband to lose control of his penis and I had to be very strict with him and refused him permission to take it off several times unless it was causing some sort of pain or swelling or some other medical issue. When it does come off for cleaning or inspection or for a 'tease and denial' session his hands are restrained behind him. Both of us are glad that we got through that period and now it seems we have settled into a nice pattern.
I have also reduced the frequency of his orgasms from once a week to once a month now and want to reduce it further over a period of several months. We generally don't have penetrative sex with his penis but he satisfies me with a strap on dildo. Both of us want and desire long term denial for him and since we are doing this for the first time, I would like to ask you for some advice. Is it safe for my husband to go say 3 months without orgasm or wear a belt continuously for 3 months with the belt coming off only for an occasional inspection and cleaning and of course for T&D sessions? Also I want to ask you about when I should release him. Sometimes during an intense tease and denial session he is literally crying while begging for an orgasm. On a couple of occasions when I have felt bad for him and have allowed him to cum he later got a bit upset with me saying that he actually wanted me to refuse him. Usually I am strict but sometimes I don't understand if I should agree to let him out and cum or keep playing and refuse.
Although I have no medical background, I would say that 3 months seems a fine amount of time to go without release. I would, however, suggest that you look into milking, which is the process of "milking" him of semen without him actually having an orgasm. This will allow him to go longer periods without any pain and/or swelling.
As far as understanding his cues, that will take time and more experience. You can also put in place a safeword (if you don't have one already) that he can say. Good luck!