My first memory of playing with myself was when I was 5. I remember it clearly because my mum and dad walked in on me and gave me quite a scolding. It was after my bath and I was wearing my pj's. The pants were very short in those days and it was easy to just lift the leg of it to get to my pecker and that was how my parents found me, laying on my bed abusing my little pecker. I don't remember wearing underwear with my pj's before but after that incident, mum insisted I always wear underwear, probably to make it harder to get to my dick. I don't remember playing with myself again until I was 10 and what let on to that was my first experience wearing boxers.
Until then my mum always bought me snug fitting y-front white briefs. I noticed a couple of my friends started wearing boxers and I wished I could. Boxers for boys had just started becoming available. Before you could only get them in men sizes. I asked my mum a few times over a few weeks and one day when we went shopping, she stopped at the boy's underwear section. I picked a couple of silky ones and couldn't wait to get home to try them on.
At home I stripped and pulled on a pair. It felt great. I pulled my jeans back on over and when I started walking around I could feel my little dick rubbing against the silky material, making it tickle. Before occasionally like when I was jumping on a trampoline or running down stairs I also got a slight tickling feeling but this was much more intense. I got a big hardon and the rest of that day had many. That evening after putting my pj's on over my new boxers, the tickling became even more intense as my pj's were very loose fitting, allowing even more freedom for my dick to rub when walking around.
By the time I got into bed, my dick felt very sensitive after all the rubbing during the day and I started playing with it after a while it felt like I was going to pee but I couldn't stop myself and reached my first dry orgasm. This happened almost every night after that and more than once a day once my hormones started kicking in when I became a teenager.
With only 2 pair of boxers at first. I still had to wear briefs often when both boxers were in the wash and it was always exiting to see them back in my drawer after being washed. I would immediately change into one of them. I nagged my mum for more and eventually stopped wearing briefs as I had enough boxers. I am 23 now and still a boxer guy. During the first few years after getting my first boxers, when talking about sex with friends, I would ask those who also wore boxers if they also liked the tickling feeling when your dick rub against the material and some denied feeling any rubbing. I realized after a while that those who denied it was uncircumcised and was thankful to my parents for having me cut as a baby.