In kindergarten I found out about boxers. I was at the urinals with for some reason when all the way to the floor and had nothing in between them and a classmate of mine came up next to me and put his pants done and I noticed the his underwear was differen then mine. so I asked what is that and he said it was boxers and that I should wear some. I said cool and we went on our own ways. I didn't mention it to my mom but in the back of my mine I could not get the idea of wearing boxers out of it.
A couple years later I meet this girl with blonde hair that was so cute and sweet I started hanging out with her after school and for birthday parties. She had a nephew that was the same age as me and one time we were at her house and we were changing into our swimsuits to use the hot tub and he had convinced me to wear my underwear under my swimsuit so I did, but as we were getting our clothes back on I realized either I would have to wear wet underwear home or go without so I when without. I think I changed back into underwear as soon as I got home but I can't remember. that was the most fun I had up to that point.
Within the next few years my mom had switched my underwear from white briefs to colored ones she also had got me a pair of 2 cartoony boxers that I could use to sleep in. It was great having boxers but I was told that I could only use them to sleep in which was better than what I had been wearing to bed which was a shirt, underwear, and pajama pants or a footie with underwear. I didn't wear them much only because I didn't want my penis coming out of the opening. Later on I realized that they were in fact boxers.
Over the years I had tried a few times to go without underwear but I just couldn't bring myself to doing that which in my head it felt as if I was breaking a law or something. I kept at it seeing how long I could go before I just had to put them back on.
My mom had then decided to buy some boxer briefs which was great they didn't cut into my crotch or anything. I had almost completely switched to boxer briefs. I loved the length of them and that if I wore them lower It was almost as if they were boxers but without the bunching of boxers.
When I was about to hit puberty I had tried to wear the boxers as underwear a few times and it was weird. they weren't soft like briefs but gave the coverage that I wanted. I would wear them as much as I could at home and around the house. I kept them for years I still have one of them in my draw but I don't wear it anymore.
During one summer I went on a week long summer camp for Boy Scouts and one of my friends was a swimmer one the swim team back home. I was not a good swimmer. During this week we had an triathlon of some sort which involved canoeing, swimming and running and each troop had their own team which any of the scouts could participate in a part of it. Now he had his swim jammer on which I thought was extremely cool and wanted one of my own and thought that if I was wearing one I could be as good as he was. Another time I went up there I noticed more scouts wearing them.
Once I hit puberty I was all into boxer briefs but slowly they became worn out. My mom decided that to save money and which me and my brother back to briefs which I hated because by that time I was in high school and no one wore briefs. They all had either boxers or boxer briefs. I saved my good colored briefs and boxer briefs for days we had gym.
Sometime during high school my mom wanted the bathroom repainted and she told me to do it and I had a full day to myself all alone to paint the bathroom. she said since I would be the only one home for the day I could do it in my underwear or even naked which in my mind was like fun. so I got out all of my painting supplies and the paint and stripped down to only my boxers and got to work. I had painted many times before but always with someone so clothes were a necessity. but this time I was all alone and could wear as little as I wanted. once I got everything taped off I could start painting and as I started painting I decided to lose the boxers and go all out naked. So I finished painting completely in the buff washed up and put my clothes back on before anyone came in. It was the most fun I had painting.
in my last couple of years of high school I started to try to sleep naked every once in awhile which was fun. I didn't do as much as I wish I had but my senior year I had my own room and was able to do it a lot more but the room was in the basement and it was not heated.
Once I finished high school I went to live in an apparent while I went to a school to teach me how to live on my own which I thought was really dumb. my mom had taught me everything I needed to do to live on my own. but while I was there I went to a conversation in texas which was awesome but before I went I had bought this pair of jammers to wear under my swimsuit. I always wanted one to see how it felt to wear in the water so when I was there every time I went to the pool I would put them on under my swimsuit. This kinda made my swimsuit a little more loose but it also made it harder to see through since the suit was white wish blue Hawaiian flower pattern on them. It made it feel very weird but I liked it.
Once we got back I decided to go up to target to get somethings and as I was there I found some boxers on sale so I was like I always wanted to wear boxers so I picked up a pack of them but I also wanted boxer briefs so I got a pack of those to and as I was going through the men's department I spotted these compression shorts which were also on sale so I looked around for my size and the colors I wanted and pick up a couple of those too. I then was looking through the shorts and found this pair that was on clearance and it had a compression shorts built right in them so I picked them up to and a compression shirt. I then finish my grocery shopping and went to the checkouts. All together it equaled about $75.
Once I got back to my apartment I opened up the boxers and tried them on and it was awesome. I then tried sleeping in just boxers and that was even better. So I started spending my evenings in just my boxers which made it very fun. I was thrilled to finally have enough boxers to last all week. I also wanted to wear compression shorts too so every once in a while I would wear them around but it wasn't as thrilling as being in boxers.
Once I finish there I went back home for a couple of weeks and kept wearing the boxers. Then I started college and I kept wearing my boxers summer which was difficult to wear them then because I was doing a lot of building which involved me moving round a lot and the boxers would creep up and bunch up making it uncomfortable to wear so I had switched to the boxer briefs. They also kept my package from getting tangled up or sore from all the movement. but once college started back up I swithed back to my boxers. I stayed that way until I read about freeballing. I took it as a challenge to go without underwear for as long as I could and the rest is in the other posts.