Hi @Shy_Wife
A lot to unpack here. Rockstart has given you some solid advice, I would just add, go at your own pace, don’t let hm “top from the bottom” with demanding teasing sessions or releases etc.
How long is it normally between his releases? If its say 2-3 days, perhaps start by stretching that out to double the normal time.
You could set up some sort of ratio (in your mind), he’s not allowed to cum until youve achieved x orgasms?
You could make him earn releases in other ways (back rubs / massages, housework, cooking etc).
There really are no rules around chastity, it is up to each couple to create their own journey.
Mrs Sen was apprehensive about the device itself (and even moreso since I showed her the short cage) over concerns for the physical well-being of my penis, how it squashes into the cage, the ring pulls on the testicles when an erection forms etc. For the most part, they are pretty comfortable, only becoming uncomfortable when aroused (which is the point of them) and overnight when you don’t have any control over erections.
I’d suggest starting him off during daytime, he will take time to get used to wearing a cage, a few hours at a time, then perhaps during a working day, then all day / evening and finally overnight. If he does wear it in the evening, use this time to become familiar with how it looks on, how it feels to touch / hold him in it etc.
There is another forum, chastitymansion that has a dedicated area for females (the men can see but not post) and the ladies are very helpful as many of them have been in your shoes.
When reading out your post to Mrs Sen this morning, she simply said “you just bought it”, which I guess I did, but when I bought my first cage, I had no idea what path I/we would go down. Even now after 3 months or so, we are still learning.