When specifically speaking about rings, the key function the size of the ring plays is how much it constricts blood outflow from one’s penis. A smaller diameter will allow less blood out. Knowing your sizes in advance allows you to decide in advance how much you want to constrict (and how hard you want to get). This is all part of the balancing act - an act that is influenced by your mood and your intentions when you put the ring on.
The level of comfort for an adornment is influenced by a number of factors - some are obvious while others are a bit more surprising to hear. In fact, some of the things that I prefer for a comfortable wear are in opposition to days where I prefer my adornment to… um… do a little more than look good.
In my experience, the absolute most important factor for comfort is the shape of the adornment. It is all but guaranteed that a steel tube with crisp 90 degree edges is going to pinch while wearing. The most common item for comfortable wear is a typical cock ring, so put that on as the general mental model of our discussion here - but don’t only think of rings. Many of the things that make for a comfortably shaped ring apply to other types of adornments.
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