Should a cock ring be painful?

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Some people like pain and go for tighter things but it seems he doesn't. So I would say that you need to find a different one for him. Measure his girth. Get something stretchy, smooth, soft.

I don't understand how the rabbit and cock ring are inter acting?

I have some metal cock-and-ball rings that can hurt when my girl is on top - the metal presses on my pubic bone. This doesn't happen with my silicone ring or my stainless steel Omega.

A cock ring should not cause pain, unless that is your intent. Pain is the body's way of telling you something is wrong. If the pain is from the start then it may be to tight, if the pain comes after some time (no more that 30 minutes is recommended) then it needs to be removed. If it only hurts in certain positions (Like Gunsmoke is saying) then try a different position.