I hate wearing underwear of any kind. As a young child, about the age of 8, I started to go without underwear.
During a gym class, I had forgotten to bring my gym shorts. When I told my teacher, she told me that I had to just participate in my underwear. I discretely told her that I did not wear any. She told me not to make a big deal out of it and to take my pants off, or end up in the principle's office.
Right in front of her I un did my pants and right away popped out a partially erect penis. My class mates cheered me on. I was told to just put my pants back on, but by now refused to do so. Since the gym was several km from our actual school, she could not take the time to drop me off at the principle. That day I participated in gym class totally nude. I enjoyed myself and impressed to other boys with my boldness.
I had a very unconfortable female teacher. It was her idea to take off my pants.
Later that day, I was called into the priciple's office, class room. He told me that my actions were unexeptable and that he would talk to my parents. My mom did not have to say much. She was a kindergarten teacher and was quite familiar with seeying little boys nude.
My dad told the principle and teacher that he would not punnish me for what I had done. He tought it was a brave act on my part. He also let the teacher know that she was unwilling to believe me when I told her that I did not wear any underwear.
Both parents did encourage me to wear shorts under my pants. I did it for a few weeks, but decided that I hated the feel of any underwear, briefs or boxers.
I had another occasion later on while I was in my teens. I ripped a seem of my pants while sitting down in a class room. The split was on the sides, but did reveal a lot. From the side my penis and scrotum were visable.
After class I had several girls making comments on me. I did go home to change, but enjoyed the attention.