Hello
I too never wear underwear. The freedom of having no encumbrance under my clothes is liberating. My problem is that at a venue I volunteer at its totality inappropriate to be nude and since I've lost some weight my shorts don't stay up very well. I'm constantly pulling them up and hoping that they don't fall off before I can pull them back up. LOL
Oh go on! I have lose shorts like that. I san feel them slipping down my waist and then my bum with every movement. Then they suddenly and unpredictably fall to the ground. I look surprised and hoist them up. Nobody gets blamed for "accidental" exposure. I never wear underwear either.
My chosen cover when going to and from the beach is a flimsy cover. It barely covers my bum or my bits which is fun on a windy day. It is also see-through when close. That causes friendly amusement amongst the ladies. Now I have got myself a C-string. It's like a G-string but without the tapes - no visible means of support.