Suggestion number one is shave your balls the lower part of your dick and the lower part of your pubic patch. Getting a cock ring on and off can be problematic when you have a lot of hair.

Suggestion number two is start out with a set of at least three different sizes of neoprene rings. Here in San Francisco the sex toy shops on Castro Street and elsewhere have these multi ring sets for a very low price. That way you can determine the right size for you without spending much money. Also, if you get one on that is too small for you and you cannot get it off again, you can easily cut it off. After you determine the size that is right for you, you can consider surgical steel.

I've worn a cock ring 24/7 for more than ten years now, so if you want further information send me a Private Message.