My soon to be wife and KH and I have been doing male chastity for nearly a year. It's progressed to a long term thing and she's been getting more and more bold lately and I LOVE it! My last orgasm was June 22nd and even though we're getting married in just over a couple of weeks she's made it pretty clear that I'll probably be locked while at the altar and even afterward, an orgasm isn't in the near future for me. I'm very lucky!

Anyway, I've been using a CB6000S this whole time and, while I get used to it after a while, anyone who's worn one long term knows that they're bulky and require a certain amount of additional effort when caged for any length of time. We've talked about getting me a different cage that works for more long term chastity and I really like the Mature Metal Jailbird so that's where I'm leaning.
Now, we all know the CB-X rings essentially come apart. I'm currently using the one sized right in the middle and it seems to work (although I've thought of experimenting with the next down since I like it "high and tight". As an experiment, the last time I was allowed out for cleaning, I removed the cage while keeping the entire ring intact - No problem!
However, when I went to put it back on with the ring intact it wasn't gonna happen. I wasn't hard at all, but getting the entire package through there seemed impossible (at least, not without a fair amount of pain).
Is there a trick I don't know about? I really would love to go with a metal cage, but I don't want to spend the money if I can't even get the thing on after all that waiting..
Any advice you all have would be great. Thanks in advance!