I've always loved to go without underwear. It feels great. But it can lead to trouble!
I discovered the pleasure of going without underwear at a very early age. When my mother would hand me my clothes when I was little, I dutifully put them all on, which included tight little briefs. But when I dressed myself, I sometimes just didn't bother with the briefs, and just wore my shorts without any underwear. I found I liked the feel of being free inside the loose shorts, and that was my preference. Even when my mother dressed me, I would often sneak into my room and take my underwear off and put my shorts back on.
I had a playmate the same age as me, and I can remember one day we were sitting out in the back yard playing with trucks or something, and my shorts rode up enough so he could see I didn't have underwear on. He asked me why, and I simply told him I liked the way it felt to not have underwear. So he got up and went behind the shed and took his off, and we spent the rest of the day playing without underwear and flashing each other with giggles. After that our play almost always involved going free, and when we went into the woods, we'd pull down our pants and play naked. Sleepovers were great, as we'd sneak our pjs off after mom said good night, and we'd wrestle around.
The only time I got caught in an embarrassing situation because of this was when I was around 13. I had been into masturbating since I was 8 or so, and by now was ejaculating. The most aggravating thing about that was that I would dribble afterwards. No matter how much I would wring out my softening penis after jacking off, little bits of semen would dribble out for a long time afterwards. I called it my leftovers.
Well, this day I had been in my room jacking off, and right after I came my mother came running upstairs yelling for me to hurry up -- I had my swim team physical and she had arranged for the doctor to wait in his office until she got home from work so he could see me. With her running up, I didn't have time to put on underwear, and just threw on a pair of shorts and ran to the car.
We got to the office, and the doctor was ready to see me. He told me to strip to my underwear so he could examine me. I was really embarrassed, and blurted out that I didn't have any underwear. He said that was OK, just strip down and it wouldn't take long.
He sat me down on the edge of the exam table and did the reflexes thing with his little hammer on my knees and ankles, and I realized with horror that my penis was leaking my 'leftovers.' My penis was laying flopped over on my thigh, and there was an obvious little pool on my thigh with a little ribbon of milky white semen coming out of my piss slit. The doctor had me lay on my back on the table to do his stomach thumping and stuff, then the moment came that I had been dreading. He asked me if I always leaked like that. I knew he was worried that maybe I had a problem, so I told him 'no, only when I......' I couldn't finish the sentence. He said, 'oh, after you masturbate?' I gulped and said yes. He asked how long ago I had done it, and when I told him it was less than 15 minutes ago, he chuckled and said that was OK.
Of course by that time I had an erection, adding to my discomfort. The doctor handed me a paper towel and said I'd better wipe up before putting my shorts back on or I'd have a stain. I thought I'd die.