As a boy I usually wore briefs and continued into my early 30's. Then, one night when I was cruising a rest area restroom, the attendant offered to let me suck him and I noticed he was commando. Afterward, I asked him about it and he said that underwear was an invention of the religious right and that he would never wear it. I gave it some thought and after that night I stopped wearing my briefs. Wonderful feeling immediately!
Then, many years later, I was nearly killed in a car wreck. My minivan was totally crushed and they had a terrible time getting me out. I never lost consciousness and I can remember the EMT, cutting away my cargo shorts and finding nothing underneath. Sadly, it was a gal and not a guy. That eliminated my last scruple about briefs. Now I go to physical therapy twice a week and my therapist pulls down my sweat pants and always knows that all she is gonna find is me. I used to worry bout it, but no more. I always hated underwear and for the past 35 years I have not worn it.
If you are afraid to try it, just do it once. That should prove the point.
In the days when I was out cruising restrooms and parks, I loved to see a guy going commando. It usually meant he was gonna be more fun than the guys with underwear.
Since COVID started and I had to work more from home, I decided to go commando all the time. My god, I thought I should put some underwear again one day (my gland was so dry that I got dead skin, thanks the baby Aquafor to cure it).
My god, was not comfy at all to wear what I used to. I used to wear some boxer brief. Today, Im 100% converted to be 200% commando.
If I need to wear something, will have to be something smaller than a brief, like the man store cheeky brief for example. Which uncover the butt cheeks, and feels good.
Since not long ago, Im owning a nice steel cockring easily 12mm wide. Love to wear it.