You rascal, you. One of the 6% (1 in 16) who rarely wear them ('cept now and then when needed). BTW, welcome to the site! Explore awhile, check with CandyGal for questions.
All depends on who's here. I live alone, except when I have my younger daughter here Friday thru Sunday. Alone, I'm either naked or just a light pair of comfies on if I get chilled. But the weekends I make sure I wear underwear.
What does underwear look like? Haven't wore any since . . . . . well since about 50 or more years. Not to the doctor. Not for surgery. Not at all. Ever. What's the point behind wearing underwear anyway?
I always wear them because I tend to get my penis find an inconvenient position and it gets hard frequently when I get aroused If I knew women to be receptive and appreciative I would have no problem letting them see a happy bulge. But not everyone is the same so I play on the safe side.
Only if someone request me to wear them prior to sending naughty photos which is rare that it's requested. Other then that. No.
I used to have this friend loved playing with my penis so much when she came she wants me to stop wearing underwear when she came over. It only took a few minutes for her to take it out. And it came a time I had PJ pants, it was easy to take it out, we watched a TV show while she stroked it. Once in a while she would finish me with the handjob and I took care of her the rest of the evening until I got hard again. Most other times we would go to the bedroom when I started leaking precum and we started having our fun.
I get the feeling it is cooler for women not to wear underwear. I'm certainly in favor of women going panties free as it were, but you know what they say, if there isn't a picture, it didn't happen.