Want a piercing but have many questions:

Hey there!

I've been enjoying chastity for a while but my KH and me want to make it more secure with a piercing. I have a few questions:

1. How much does it hurt?
2. When can I wear a chastity device?
3. How do I stretch the piercing? By "overstretching" it with a sound or just by putting in a larger diameter piercing after some time?
4. I'm uncircumcised and many people say that uncircumcised piercing will be bad or not even possible - how are your experiences there?
5. I'm a bit worried that it will irritate my urethra - I tried sounding a few times and it always stung afterwards when urinating - did I do something wrong or could my urethra be sensitive to contact and could that also happen with a piercing?
6. Some people say that a pa piercing was the best decision they ever made, others tell horror storys about nerve damage and people fainting when getting the piercing - what about that?

I hope you can answer my questions and help me with my decision and get rid of my worries ;)

Best regards :)

EDIT: Can you recommend any good beginner cages for uncircumcised people?