My wife doesn't always like my thin shorts, as I have a pronounced ridge on my head, but I do it anyhow. There are times when she wants me to show off and wear as little as possible, so that other women may look too - I enjoy when she's in that mood!
I never wear underwear on weekends. Ever. I do on weekdays while I'm working. One of my friends never wears undies when we go out for drinks or dinner and she always wears a skirt and she always flashes. Big tease and she loves to see me squirm knowing that in a few hours she'll be on her back screwing her bf while I'm stroking off having just seen her bald, cute pussy up her skirt.
Nice but I am mostly NAKED, unless I have to go to town, but the no pants (under wear in the UK), The hospital and my GP Practice all know I am a nudist.
I didn't wear underwear alot, then I got a cyst on my ball and the Dr. said I needed support. I am trying without again to see if the pain from that is gone. If so, I won't wear underwear anymore. I really don't like them.
I plan on going a week without any underwear. If that works, I will just keep going. I haven't really liked wearing underwear since I was 13, and even in my teens I was going all day most days with no underwear.
It's looking good for not wearing underwear. 2 days ago, while I was doing it, I thought: "I'm too old for this" but now I am perfectly fine with it mentally. Also, the testicle pain is not returning so far. Actually, I feel normal without underwear and overdressed and uncomfortable with it. I will start another thread in a different forum if I continue. It will be about freeballing and where I go and what I do in public with no underwear on. To me, underwear feels like I am wearing sandpaper.
Depending on where I am going. No underwear going to the clothing optional beach. None when going to a bar I am a regular at. No underwear and snug jeans at an art gallery got me squeezed gently and propositioned.