Chastity and orgasm denial discussion

Could use some guidance on the “stocking method” for inserting the penis into the cage section of a trapped ball device. Here’s my process: I cover my penis with the stocking, pass it through the cage from underneath up out the tip, and draw the penis in until it hits its limit. That part works fine. The issue is that the stocking gets caught around the penis inside the cage, making removal quite troublesome. Any tips on handling this? How do you remove the stocking after using it to insert the penis? Do certain types of stockings perform better—maybe thinner ones or those that slide off more readily? For context, my device is a Jail Bird from Mature Metal. It’s excellent for hygiene, allows good airflow, looks nice, and offers comfort and security when sized correctly. My initial sizing attempt resulted in both the base ring and cage being too big. Now I might have swung too far to small. The large fit was comfortable but tended to slide down, allowing me to slip out the back. The smaller fit is very secure (even without a pullout pin), though harder to put on and take off, and causes discomfort when not flaccid. Not sure if my stocking issue stems from the cage being too tight or if there’s another fix. Thanks for any advice, experiences with getting the penis into a snug cage via the stocking method, or other methods that worked well.