Shortly after I turned eighteen, I made a seamless transition from actual schoolboy to adult schoolboy. These shorts were gifted to me by my former housemaster. He had taught in South Africa before and told me boys of all ages wore shorts like them to school there. I found the knee socks with red bands (my old school colours) online.
When I visited him dressed like this, he was delighted to see me. He said he had taught boys dressed the same way during the apartheid era and had occasion to cane many of them across the seat of their shorts. He said that he had always felt I would benefit from such discipline.
I'm sure I blushed furiously at the suggestion and I know I felt a tingling sensation in the front of my jockey y-fronts. At which point he took complete charge, saying that unless I could give him a very good reason why not, he was going to cane me. I was lost for words.
In no time at all, I found myself with my blazer off, bending over the back of a dining chair, shorts stretched tight over my bottom. He gave me a good, old fashioned six of the best. I heard the swoosh of the cane through the air, then the loud crack as it struck my backside - and then felt the searing line of pain burning deep into my buttocks. There was a brief pause as the pain built, and then the next stroke followed, as hard or harder than the previous one.
By the time he told me to straighten up, to my embarrassment, the tears were rolling down my face. He said that I took my beating like a much younger boy, but I had always been a late developer, so that was no surprise. He also said that he had been admiring my pert bottom for a long time and only wished he could have started beating me sooner.
I asked him if he thought I would need to be caned again by him and he said he thought it was more than likely. He said we would discuss it when I next visited. He also encouraged me to wear my uniform as much as possible, because it would help other people to understand that I was really still just a boy and should not be considered or treated as an adult.
When I got home, I sat on the hard wooden chair in front of the desk in my bedroom, still dressed in my uniform. The angry welts on my backside made me squirm uncomfortably. As I squirmed in my seat, my small, soft willy squirted repeatedly in my underpants, the juice soaking through the front of my shorts. I was embarrassed all over again, although nobody had seen, at least.
