Chastity and orgasm denial discussion

So I know there was a thread recently about base rings being too tight during sex but I didn’t find many tips about how you get the damn things off.:) I’m in a MM Jailbird with a pretty tight double base ring. It’s a half-size smaller than my previous ring which I found was allowing a lot of slippage. The new double ring is very comfortable and secure during normal wear. My cage is 2 7/8” long so it’s fairly heavy. I’d like to go shorter but I’m still working on it, not much you can do when you’re 3 1/2” flaccid. So this spawned because I’d never actually gotten erect in only this new ring. As a rule I really try to get the base ring off because I’m not fond of the feeling of having an erection with it on. Furthermore it’s almost impossible to get the cage back on again without having an orgasm and getting soft. Last night my keyholder was teasing me and decided she was going to allow me an orgasm. I mentioned the issue about the base ring (she’s still learning a lot about how the cage works, for me). Since I was already really straining in my cage I put a little bit of lube on my shaft around the base ring. I took the cage off and then tried for the base ring… that was a no-go. I think it was a combination of how excited I was and that the lube actually made it hard to grip the skin behind the base ring and pull the shaft out. And after 30 seconds or so I’m at a raging erection due to not having come for so long and the base ring acting as the tightest cock ring ever. So it’s absolutely not coming off at this point. Anyway we proceeded as normal. My cock was really purple and I only had maybe a 1/2” of play for stroking before the base ring pulled the skin on my shaft taught. When I was told I could come I did… but no semen. Apparently the base ring was so tight it restricted it and caused a retrograde ejaculation (when semen goes into your bladder). And I’m not getting soft. Yeah, it was so tight I wasn’t able to lose my erection, even after orgasm. So I’m kind of freaking out. I’m going to have to go to the fucking emergency room and have them cut this thing off. I sat down on the toilet and tried to pee. Eventually I figured out by pulling up on the ring and toward my body and pushing down on my shaft I created a little bit of extra room and I could soften a bit. After 5 minutes a little semen came out and after 10 minutes I was able to finally get the damn thing off along with releasing a (yes, very gross I know) piss/semen mixture. I’m considering going back up a half size and having that made into a double ring to see if it helps. Regardless I don’t think I’m comfortable having that happen again so I’m looking for a way to make sure I can get the ring off. tl;dr If you’re straining hard and take your cage off, how do you make sure you can get the ring off, too?