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Make sure that your ring is tight and snug, but not uncomfortable to use for an extended period. For first timers, opt for a penis ring multi-sized set or adjustable band. These will let you experiment with a variety of sizes to help you find a level that is comfortable and effective. Stretch the ring outward and over the head of your penis. For fixed or metal rings, you can also add a bit of lube to the ring or your penis to make sliding on and off more comfortable.