I'd like to answer this question through my own experience. It is still fresh in my mind as from only 10 days ago. Others may have different experiences but here is mine.

Bottom line is "no" it really doesn't hurt. I had a lot of apprehension leading up to this. I keep asking myself "is this really going to be what I want long term?" If I hadn't had the firm conviction/commitment of my wife that this is what I needed I could have easily backed out. It is after all a very personal thing to have a hole cut in your dick. I had been through the endless questions one has during the investigation stage. I'll cover all of those under another post. My final thoughts before the process were really that my wife wanted this, I felt it was beneficial to me and no matter what I was going to try it.

I had selected the shop. They do both piercing and tattoos. They didn't take appointments so I had one earlier aborted attempt when they were backed up with customers. This time for sure. I had carefully planned this for a Friday so that I would have the weekend to deal with whatever may come. I went in during my lunch from work because they opened at noon. Rats, already backed up with two piercing before me and a woman with endless questions but not commitment. Wait and wait, the empty butterflies in my stomach. An hour and a half later, it was my turn. Quick final questions and then we went into the private room. He has me drop my pants and lay on the table. Looked a little like an examination table in a medical doctor's office. First embarrassment, maybe I should say second after dropping my pants was that my wife makes me shave my pubic hair. He doesn't say a word, I'm mortified. I think to myself, I'm sure he has seen a lot in his line of work. He had even talked about learning how to pierce from a doctor who was "into" bondage. Well, no time to think about that. He's rummaging around selecting the instruments of pain. This particular piercing is done by inserting a tube into the urethra of the penis and then when it is appropriately positioned the needle is poked into the tube. He is measuring and marking to be sure he has the right spot to pierce. All finished and I feel the tube being pushed and manipulated into my pee hole. This is strange. This for me was the most "uncomfortable" part. The tube has edges and as he inserts and then lifts/aligns the tube under the appropriate spot to be pierced, it is borderline mild pain. Finally it is in position. He tells me to take a big breath and let it out. As I let it out he pierces me. It feels a lot like getting a sliver in your finger only probably not quite as painful. Piece of cake. THIS IS NO BIG DEAL. It's a little bloody but rather painless. This part of the anatomy has a lot of blood supply but that is also what makes it heal fast.

Insertion of the jewelry is fast and easy, no pain. All done. I don't wear any underwear so the whole "feminine pad" discussion doesn't apply, but he puts some paper towel under the piercing and then pulls his whole glove off inside out to give me a nice neat way to prevent a bloody mess in my pants. The psychological effect is amazing. I'm thinking to myself and later tell my wife "I feel like a real stud muffin." The whole idea of having a ring in your dick is similar to one in the nose. The subordination to the wife is subtle with this piercing but it gives me a glimpse at what it will be like to be locked into chastity.