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.
Being Locked up in a Plastic Chastity Device
Quite some time ago I purchased one of the all plastic chastity tubes for use with the Frenum piercing. I'm writing you to tell you that my wife absolutely loves it! She thought it was odd at first but soon grew accustomed to the peace of mind it gives her. I knew she had doubts because I have women friends some of whom are single. Once in a while my wife would ask me if I was having sex with any of them. I honestly wasn't, as that's not the way to make and keep women friends, but I could see why my wife would have doubts. Well since purchasing and using the tube she no longer has any doubts. I can meet a single woman 20 years my junior for a run in the park and my wife raises no objections. The tube allows me the freedom to have women friends, meet them for lunch, whatever and my wife is confident and content. All and all it has worked out well for us. My wife can see I've no intentions of wandering and it wasn't hard for me to get used to wearing the tube.
My Wife and I maintain a D/s relationship and have now for over 15 years. Early on we began searching for a way to give Her real control in our relationship. One day I saw an online add for a CB-3000 and I was immediately hooked and began wondering what it would feel like. I had no idea there is so much involved with male chastity and thus began the learning journey. We went through a CB-3000, a Steelworxx, and a Noesteel belt. The plastic CB-3000 seam broke within 4 months. The Steelworxx was excellent but I could pull out of it, and it also caused sleep issues. The Neosteel was amazing and I wore it for years but it had to be removed every few days to be cleaned. For me, full belts are not comfortable or practical enough for 24/7/365 wear. It was back to the Steelworxx and I wore that for many years. I had seen Lori’s devices by now and was intrigued but was terrified of getting a PA. My Wife did not want me to go this route either. Fast forward a few years and my Wife started becoming very serious about owning and training Her slave husband. After many discussions She decided that She wanted Her slave to be in real chastity with 24/7 security. We looked at Lori’s devices again but were not quite ready to order and so I emailed Miss Lori and she answered all our questions. My Wife finally made an appointment for me to get a PA and came with me when it was done. Years of wondering, months of worry, a few seconds of pain and it was done. It was not that bad at all. The anticipation of a PA is far worse than getting one. Days after I was pierced I emailed Miss Lori again and her detailed and quick responses really impressed us. My Wife decided to go with a 2A because it looked easy to keep clean yet provided enough coverage to prevent stimulation. As my PA healed and the stretching process began, a couple more emails with Miss Lori answered some final questions, and we placed the order. Reviewing the information and feedback on Lori’s website greatly helped us in our decision making process. When you get a Lori’s, you are getting the best. Her devices are completely custom to your exact specifications. She really knows how to make a device that will fit you perfectly as long as you know how to measure. I got a few extra details added into my device and she fulfilled my order flawlessly. The device arrived and was an absolute work of art. I was able to wear it with a Trapped Ball Ring until I was ready for the PA pin that came with the 2A. Months later I was finally down to a fully healed 6 gauge piercing. I went back to my piercer who removed the TBR and helped me install the device. The pin fit perfectly. When I got home I handed the key to my Wife and felt a change come over me. My Wife now has a slave in a chastity device that is inescapable, easy to keep clean, comfortable for long term wear, is hidden under clothes, and prevents all sexual stimulation. If you are serious about real chastity and wish to completely give yourself to your significant other, a Lori’s device is the way to go. When I gave my Wife the key, the feelings and emotions I had were beyond description. It was like my entire life had led me up to this point and now I had stepped through a doorway into real submission. Nothing gives a woman more control over Her man than real chastity. I am so fortunate to be completely owned by my Wife/Mistress and the love, devotion and closeness I feel in our relationship is now stronger than ever. Thank you Miss Lori!