I've had a number of these sightings, but here are three specific ones that I remember. All from my college days in the mid/late '90s:
1. College roommate lying in his bed--reading a book, just wearing boxers. I was sitting at my desk chatting with him. The boxers in question were rather short, and I could easily see one of his balls when he spread his legs and hung one leg off of the side of the bed. Nothing fell out per se, but everything was on display. Guy was an athlete and hot. I'd seen him dressing before (obviously, since he was my roommate), but this was somehow more fun, since he had no idea.
2. Over the summer, I went sailing in a small boat (the kind where you sit on the floor of the boat and bend your knees to fit). One of the guys I was sailing with was wearing short shorts and loose boxers (longer than the shorts), and one of his balls was clearly visible. Again, he had no idea.
3. While visiting a friend at a different (nearby) college, I did some reading in the library. They had four couches set up in a square, facing each other, with a table in the middle, so people could be comfortable while reading. Random hot guy decides to sit on the couch opposite me and put his feet up on the table. He was wearing short shorts, and was obviously not wearing underwear. This was actually what kind of put into motion my idea of giving up underwear entirely, since he seemed so confident and comfortable.
Also, there was a time in the early 2000s, after I had graduated from college, when I think that I gave a bit of a show unintentionally. I was wearing jeans with a hole (1" or so in diameter) just below the zipper, which I had not noticed, and not wearing underwear. No one said anything, and I didn't notice the hole until that night, but I had been all over the city that day, on public transportation and doing errands.
1. College roommate lying in his bed--reading a book, just wearing boxers. I was sitting at my desk chatting with him. The boxers in question were rather short, and I could easily see one of his balls when he spread his legs and hung one leg off of the side of the bed. Nothing fell out per se, but everything was on display. Guy was an athlete and hot. I'd seen him dressing before (obviously, since he was my roommate), but this was somehow more fun, since he had no idea.
2. Over the summer, I went sailing in a small boat (the kind where you sit on the floor of the boat and bend your knees to fit). One of the guys I was sailing with was wearing short shorts and loose boxers (longer than the shorts), and one of his balls was clearly visible. Again, he had no idea.
3. While visiting a friend at a different (nearby) college, I did some reading in the library. They had four couches set up in a square, facing each other, with a table in the middle, so people could be comfortable while reading. Random hot guy decides to sit on the couch opposite me and put his feet up on the table. He was wearing short shorts, and was obviously not wearing underwear. This was actually what kind of put into motion my idea of giving up underwear entirely, since he seemed so confident and comfortable.
Also, there was a time in the early 2000s, after I had graduated from college, when I think that I gave a bit of a show unintentionally. I was wearing jeans with a hole (1" or so in diameter) just below the zipper, which I had not noticed, and not wearing underwear. No one said anything, and I didn't notice the hole until that night, but I had been all over the city that day, on public transportation and doing errands.