I got mine done about 20 years ago. . there is little pain when getting it. Just a pin prick, basically. The person doing the procedure, will insert a small rod into the penis, so that when the needle goes in, it will hit the rod and not go further. The whole thing takes less than 30 seconds, once you and the percer decide where the ring should exit the penis under the head. . Some say, the first time they pee, it hurts. So I was told to drink a lot of water for the first time I peed. It didn't hurt at all. The whole thing heals up quickly. I have had anal sex with men since having the piercing. I do not know if it brings them pleasure or not. I like the ring. Its very popular at parties. Men and women like to see it. . One cannot wear underwear with the piercing. Well, maybe boxers. But it is difficult to wear underwear as it will twist the ring in odd directions. This is what I have been told, you may have a different experience. I've never wore underwear since I was a kid, so it wasn't a issue for me. I ride a sport bike, and it can be uncomfortable as there really isn't any place for a penis on a sport bike. It gets pushed up against the fuel tank, and that can be uncomfortable at times. . . You have to learn to pee again. . First pic, is of a guy with a small ring, which would not effect peeing, but second pic shows how the urine flows with a ring. Third pic shows a guy with a large ring. So you have to decide what you would want. Usually one starts off with a smaller ring. And remember, if you decide you don't like the whole thing, you can take the ring out. . . So, do your research, decide if this is for you. You may decide its not for you, and that is OK.