Caught Smoking So I Could Be Caned.

My 2nd year at grammar school.
My form room to which I returned after assembly each morning was next door to the headmasters study. If anyone was bad at my school, they were named in assembly and had to line up outside the Headmasters study at 9:30pm for punishment. This included the slipper (actually a plimsole) or the cane (2 standard thicknesses for juniors and seniors).

When he had students due for caning, we kept very quiet in the classroom and listened to the muffled talking and admonishing he was giving them. Normally there was a short pause as he took out the cane, then the loud whistling of the cane and the crack it made on the bottoms of the poor souls.

Over a period of two years, I became curious as to how it would feel to be caned. Long story short, by the time I was 14, I was getting tuned on by the idea but was too scared to do anything about it. I had planned out that if I stood between the bus stop and the end of the road on an evening, It would be quiet (most students having stopped at the bus stop) and the teachers driving home or cycling would pass by me. For two years I thought about standing there with a cigarette and getting caught. It had to be smoking as this guaranteed 6 of the best with the cane and it was the cane I was fascinated with.

One month before the summer holidays that year, I decided I just had to do it or go mad thinking about it. I bought a packet of players number 6 as it was in those days and waited one evening near the school road juntion with the main road. Mrs Evans, a geography teacher was the first to leave the school on her bicycle, and as she headed towards me, I lit the cigarette some 200 meters before she passed. I turned away from her as if I didn't know she was coming and the excitement in my groin as I blew smoke out and listened to her cycling towards me was incredible. I thought I was going to *** on the spot I was shaking so much with a mixture of fear and excitement.

As she went past, she just smiled and said "see you tomorrow morning Phil!"and rode on. No shouting, no anger, just that.

In assembly the next day, she was smiling at me through the hymns and morning songs. At the end of assembly she was staring straight at me from the end of her row as the headmaster started to talk about breaking school rules. After the lecture, he read out two names, one of them mine, and as I looked at Mrs Evans she gave me a smile and a wink. As I walked out of the hall past her, she patted my bottom and whispered in my ear "I will be listening to your beating. This is going to glow in the dark for a week" as she squeezed my left buttock.

Outside the study, I found that the other boy had only been late in handing in some homework. He was nervous as I was and as we were called in to the office by Mr Hall (the head) we gave each other a knowing look. I was sent to stand in the corner with my hands on my head whilst he slippered the other boy. I had to watch and I realised how much louder the noise was when you were in the room. Much scarier that when sat comfortably laughing in the next room. Four hard whacks with the plimsol, a thank you to the headmaster and it was over for him.

For me, things were happening very quickly. I had imagined this for years and now was so scared and excited that my head whirled. I thought of the other pupils and teachers in the adjoining classroom, espescially Mrs Evans, waiting for my turn with the headmaster. They knew it was coming and I knew they would be interested to hear if I cried or called out in pain. My punishment, Mr Hall informed me was 6 of the best, the norm for smoking.

My first thought as the cane came out of the cupboard was that it looked longer and thinner today than when he had shown it to the school at the start of term. I was shaking as he ordered me to bend over the end of his desk and hold on to the far side. The first stroke was the most painful thing I had ever felt and I almost cried out in pain. The second followed about 15 seconds later and I was bracing for the third when there was a knock at the door. YES he shouted, and the door opened. There looking straight at me was Mrs Evans. Sorry headmaster she said, I need to discuss something with you, I can wait out side. Yes please he said and with a cheeky wink straight into my eye she said "I'll just wait outside here".

I felt a familiar twitch in my groin as I looked at her smiling face. I was initially scared I may become erect, but this passed as the caning continued. The entire universe for the next 5 minutes only, to me, consisted of my burning buttocks and the noise of his cane. I was red faced and could hardly walk out of the office, I was in such pain.

A familiar pat on the buttocks from Mrs Evans on the way out felt like a lighting strike on my caned bottom. The headmaster followed me out and said I could use his rest rooms for 10 minutes to recover. I locked myself in and ******** to survey the stripes he had given me. All the while I could hear him talking to Mrs Evans and she was asking a lot about the caning and agreeing that it was good for boys like me to be beaten.

As she talked and with the burning in my bum spreading to my thighs, I could contain an erection no longer and had the most intense climax of my young life so far, there in his bathroom.

Mrs Evans and me became friends after that.... but thats another story.
barmysamsam barmysamsam
46-50, M
2 Responses Jul 12, 2010

I was, but I always regret that I did not receive a bare bottom caning from a man. Had plenty from ladies, but it just lacks that sting. <br />
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It's my fantasy as I always imagine the intense pain and the fear of what else may happen to a boys bottom in the privacy of a mans office!

Sounds like the experience lived up to your expectations. Were you ever caned again?