The first time I remember spanking someone was when I was at the tender age of 7. Me and my friend Michael used to play around my house quite a bit. I wasn't even interested until one day Michael suggested playing a game of "naughty schoolboy and schoolmaster" :-)
Anyway, he asked me to take his trousers and pants down and asked me (as the headmaster) to cane him and spank him. He used to lay down flat on my bed and I used to use my bare hand and sometimes a small piece of whippy bamboo cane on his behind. I never really understood why we did this but I new it was always really exciting and both him and myself had hard-on's while doing it. Strange really I mean like I said until then I had never had any inclinations.
Later on at about the age of 9 whilst learning a musical instrument at a local school I came across my other spanking candidate. His name was Matthew and we used to have to wait around in the classroom for about 10 mins before the teacher came in during recess. Well it started by him calling me a particular nickname which I was a bit offended by. When he said it the first time I chased him around this small schoolroom for a bit (a room in which btw it would have been easy to escape from). When I caught him I used to drag him over to a chair, I'd sit down and I'd pull him over my lap and give his lovely school trousered bottom a good spanking. Thinking back now I think he must have enjoyed it because everytime I let him up, he would call me the name again and I would just spank him harder. This fun lasted nearly every week for two years.
The last time it happened when I was a kid was at the age of 12 but because I think I was nearly caught, I gave up. I was at boy scouts and one day this kid really pissed me off. We were on a field playing football with a group of other kids and I told him that I was going to punish him (it still amazes me to this day that these friends of mine went along with it!) Anyway, me and this kid, plus a guy in a wheelchair who was interested in holding him down headed for a patch of trees. When we got there I bent him over this wheelchair where the guy in the chair held him down. Getting a hard on by then I grabbed a nearby stick. His bum looked lovely in his now tight gray school shorts so without further ado I whacked him with the stick. Well he can't have been prepared for that, and until this day I wished I'd just used my hand, because as stick hit bum, he started wailing. Not wanting to be found out I stopped and shouted at the guy in the wheelchair to let him up, but I think he didn't want to because he held him there for a bit more time, probably thinking that he deserved some more punishment. Anyway, he finally let go and this kid (who was my age btw) went running towards the scout master. I couldn't believe it, I thought I was in DEEP S**T. Fortunatly, and surprisingly to me the master called me aside, told me that he understood that I was angry and just told me to calm down and apologise later that evening, which I did and we were still friends. After about a month, we still had some spankings with him, but strictly by hand, over my knee with his school trousers on.
I still can't believe how much I got away with when I was younger and sometimes wish I could relive those days. I was also amazed by the amount of play whackings that went on, especially at the scouts, between the boys.
So prove to me, I'm not the only one and mail stories of your first encounters.