I got a Prince Albert piercing (a penis piercing which extends from the urethra to the underside of the glans) to use as an anchor point for my chastity cage, as I live a permanent chastity gay bottom lifestyle. God, it hurt so bad, lol! It’s considered one of the least painful penis piercings, so maybe I just have a low pain tolerance…
Probably as a child when I cracked my head open on a rock garden, that hurt so badly that I can’t even properly remember it