I discovered putting my cage on in the shower is by far the easiest way to get it on. Does anyone else do this? I lather up my package and the ring slips on with ease. Then the cage slips on so easily it is almost as if it is automatic. I use to have to put a finger hear and my thumb there to prevent getting pinched. In the shower it just slides right on with amazing ease. When my KH requires long term lock up she allows me to remove the cage but not the ring in the shower to wash up
Your Keyholder sounds like a Lovely Lady. Your ring is like your wedding ring, it shows your commitment to her and shouldn’t be removed very often. Your cage could also be the same. Time will tell
The ring only comes off for haircuts but the cage comes off every few days for cleaning until we can get a good 316 stainless one made that can be left in place much longer.
If you are thick, the Stocking Method will help a lot. http://www.tickleberry.co.uk/male-chastity/stocking-method/
If you have a problem with a runaway ball, you know the one that retract inside the body when you pull on the skin through the ring... I tie a piece of rope around the base as a cock ring then do the usual pull skin then 1 ball through, pull some more skin then pop tge second ball through then push the dick ubder the ring and finally remove the rope...
Regarding getting back in. The shower works but I guess I have been doing it so long no all I need is a little lube and a shoelace or something through my PA to pull it on. I recall that i took me an age to consider trying putting my left one in first, I've no idea why it did... and its so much easier, I guess its because its the lower of the two. Maybe its because when my then wife and I got our first one she was the one that used to put it on me, because it turned her on so much and she always went with my right one first.