This is just a side note on my experience.... but if you are struggling putting a ring on that seems to small... try the other testicle first. I had always put the right one in first and I figured I would try the left one first the other day. 100x easier, figured I would post it here since it is a noob topic.
I just think it should never be removed so as to avoid all these problems. No reason to remove the ring.
Well one of mine is hinged, so once you remove cage it sort of falls apart. I like being able to hold both balls out and slipping ring in behind them. Avoids choosing which one goes first.