Why does it work? When urinating, gently squeezing the penis with two fingers to remove any remaining urine from the glans creates a slight stimulation, allowing the local nerves to become somewhat "accustomed" and less sensitive. This is similar to the concept of "desensitization." On the other hand, it helps keep underwear dry and clean. This is actually what is medically known as urethral milking (urethral compression/...