into boxer briefs nowadays

I had my frenulum pierced few years back, and happy with it. Frenulum piercing does not interfere with the urethra lining and doesn't really hurts.

Id say you definitely need help with the kit ( my kit explicitly said have a partner help you with the measuring , timing , etc.) being the DIY, independent type i am found out that you really SHOULD have a partner. I have friends that have a collection of their most endowed fiends on display on their mantle, however they are completely tight lipped as to who is who. (whew!)