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Generally they're worn around the base of the cock and behind the balls. The easiest way to measure the circumference is to use a cloth measuring tape (or a piece of string/yarn). Just wrap this around the spot where you want to wear the ring. As a rule, a cock will swell once the ring is in place, so an overly tight ring might become uncomfortable as the penis grows. Since a solid metal ring can be difficult (or impossible) to remove once the cock swells up, a ring made of a flexible or stretchable material might be a good choice to start, if you're new to using a cock ring.

it helps to measure around when you are limp, not hard. use a string and have it so it just adds a little pressure. this is around scrotum and shaft. the length of the string divided by 3.14 will give you a diameter. when in doubt, go slightly larger until you know what is comfortable