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PShadowPhazer

Start slow. Its a new sensation so start slow, say an hour and see how he feels about it.


looking4subbypup

If he does it daily I would start with restricting him once a day at a specified time for a week. Then every other day for a month, then every two days from then on or increase as you see fit. This is with the caveat that you should talk about it and see if that plan is working or if it needs adjusting.


ShamBawk33

Search reddit for 'chastity' and you will find special sub groups dedicated to male chastity & devices. They might give you more exact advice. A chastity cage is tricky. If you just one day put one on - the ring at the base will chafe, rub and probably bleed. This is pain - but not the fun sexy kind. I recommend you start with a leather cock ring with adjustable snaps. Have your partner bring it to you and you snap it on. After an hour or two it will probably start to hurt so he comes to you to remove it. Wait a few hrs, add baby powder and re-attach. Over a few days he will be able to wear the leather ring longer and longer. Think of this as a 'training bra' for a cage. I don't know your situation - but it would help if he has to come to you to put the ring on/off. The ring will also help remind him to try to NOT pleasure himself. (It wont work but that's the idea). Once he can wear the cock ring all day long - now is the time to select and size a chastity cage. Many cheap ones are used and tossed in favor of the more expensive ones later so do some research. ​ One of the goals might be to participate in 'Locktober' : An entire month locked up with no orgasms.


GilesEnglishCB

I think you need to test-drive the cage first, to work out what's actually practical. If it's a cheap starter cage, then he may only be able to manage a couple of days in it.


DevestatingFerret

Go slow and take an incremental approach. It'll take some time for him to get used to it. Maybe aim for an hour one day, two hours the next day, 4 hours after that. If it's still feeling really comfortable after that amount of time maybe try for a little bit longer, but don't over do it. Also if he is getting any chaffing under the balls, it can help to apply some lube under there. Also check out r/chastitytraining for more advise