Several years ago I lived in a large apartment complex with a swimming pool. One day after work when both the temperature and me were feeling a bit hot, I went down to the pool wearing very short Dolfin white running shorts knowing that they could become semi transparent when wet. I had seen another guy at the pool a week earlier with white shorts, but with underwear and liked the look. The short barely hid anything when dry, however I didn't expect how transparent they would become. When I got down to the pool there was just the life guard (who checks your ID to make sure your a resident) and two other people at the pool. As required I left my ID with the guard and went down to the pool and jumped in. When I came up for air, I looked down and realized you could see everything. I swam around for awhile and then sat by the side of the pool. One of the other guys just smiled at me, as obviously he could see everything. The other guy was too busy swimming laps to notice. As I sat at the side of the pool I kind of pulled the shorts away from my body to be a little more discrete.
Anyway, I stayed for about 45 minutes swimming and sitting on the deck with my feet in the water. When I went to get my ID from the life guard, the only thing he had to say was "Next time wear something under those shorts." I just smiled and left the pool area, walked across the parking lot to the building (pretty much in full view) and went into the building. I decided to take the elevator. At this point I wasn't quite as transparent as I dried off a little plus standing up made the shorts pull away from my body somewhat.
I thought I was going to be alone on the elevator, but at the last minute a woman gets on. At first she didn't notice, then I saw out of the corner of my eye that she was looking down and then up at me (I was only wearing the white shorts and no shirt or shoes)l She just smiled, and got off on her floor.
It was actually a lot of fun
The only time I don't freeball is when I have to dress up in a suit, but that's pretty rare or if I have to do a major presentation in front of a lot of people (I don't need anything but the presentation on my mind...) But always freeball in shorts and jeans. Particularly shorts. I haven't worn underwear with shorts since before I was about 12 or 13 when I know I gave up UW for the summer and only wore shorts.