Made to Strip for My Punishment

There I was, waiting outside the Demon Headmaster’s study trying to work out which was worse, the anxiety of waiting for my punishment, or the pain of the punishment itself. Well I was soon to find out.

I was called into the study and lectured about my tardiness and disrespect. I had not replied to his emails promptly enough, I was late making my last posting and had obviously not learnt my lesson. I was introduced to some of the instruments the Headmaster uses to ‘modify’ a boy’s behaviour; Bertie the bath brush and Mr Whippy the wooden spoon, to name but a few. I had met Doris, the dragon cane, on a previous occasion and guessed we would soon be renewing our acquaintance.

Drop you trousers and touch your toes. I knew I had to do what I was told, and quickly. I thought I might be in for some kind of warm up prior the main event. However, Bertie is basically a very solid and unyielding long handled bath brush which, in the hands of an expert, delivers a very painful blow to one’s backside. As far as I was concerned, this was no warm up! After the ninth stroke, I was told to pull up my trousers and stand in the corner with my hands on my head and my nose up against the door.

Next, dressed only in my underpants, vest and socks, I found myself over my Headmaster’s knee. There isn’t much you can do when you are held firmly in that position. I am not sure which is worse, the pain of being spanked with a wooden spoon, or the embarrassment of being over someone’s knee dressed only in your underwear. By the time Sir had finished both of my buttocks were glowing with pain and still the main event hadn’t begun!

Remove your vest and socks and come and stand over here. Wearing only my underpants, I was made to stand on the seat of the armchair and bend over its tall back with my outstretched arms touching the floor. Down came the underpants! So there I am, totally naked, waiting to be caned. I am going to give you twenty four strokes, four sets of six. You will thank me after each stroke and politely ask for the next.

After the first six I was really wriggling and crying. I had been caned before, but never twenty-four strokes. Once we got onto the final twelve, I was really wishing that I'd been more respectful, and quicker off the mark getting my posting to Sir. I was given the choice of staying with Doris or switching to Roger, the Headmaster's Rattan cane. Well, Roger and I had never been introduced and so what is a poor boy supposed to do? Stay with what he knows or take a leap into the unknown?

In the end, it was a relatively easy decision as by this point Doris had done her job very effectively. Bring on Roger, he can’t be any worse. Luckily for me, he proved to be more flexible than Doris; more of a ‘stinger’ than a ‘thudder’, if you know what I mean. Was I glad when we finally got to the end of the fourth set!

Go and stand in the corner, hands on your head and leave those pants over here. So there I was, totally naked, standing up against the door in the corner of the room with my hands on my head. I imagined the Headmaster, sitting there listening to his classical music admiring his handy work. I was on full display and I couldn’t do anything about it.

Have you learned your lesson boy? Well, given the circumstances that one was a bit of a no-brainer. Yes, I had learned my lesson for the moment. But who knows; lessons can be unlearned, can't they?