Im the same - like to have a nice hairy pubic bush but also enjoy cockrings
I think they have to be tight to do their job
To help, perhaps just give your bush a slight trim to tidy it and shave your cockshaft and ball sac smooth
I find shaving my ball sac makes it very sensitive by the way
Using a little lubricant (the sort of stuff you use for anal sex or masturbating) helps get the cock ring on more easily and reduces chances of abrading youre delicate skin down below
Also helps not to be sexually aroused while putting on the cock ring if possible

At the end of the day there is a kind of trade off between the sensation and also visual impact of a cock ring and a pubic bush. I think a total shave gives a striking visual impact and nice tight fit.

But from your profile pics you are beautifully hairy and it seems rather a shame to shave and trim.

I think it is a dilemma.

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