The Making of a Sissy Boy Slut – Part 1

It was speech day, at the end of term, and we were all supporting the headmaster in our prefect role, welcoming parents and guests and applauding during the speeches at the right moments as we had been instructed.

Watching from the back of the large hall, I thought that the headmaster sounded a little slurred and was concerned whether he would still be able to give me a lift back home once the ceremony had finished, particularly as my father was away working and the night buses were infrequent at best.

However, my worries were unfounded as, once all the guests had departed, the headmaster came and found me to tell me that it was time to leave. During the journey, which took about 30 minutes, the headmaster was in very high spirits, telling me how successful the evening had been and how well I had been doing at school and, from his animated conversation, it became apparent that he had indeed had a few sherries earlier, as he began giving me his opinion of quite a few of the other teachers, information that I felt sure he should not be divulging to a 16 year old pupil. Soon the conversation reverted to my performance and how he had helped me during a particularly difficult patch I had had with the police when I had run away from home. The headmaster told me that, if it hadn’t been for his intervention, then the police would certainly have taken it further. However, he reassured me that the case had now been closed. I thanked the headmaster profusely, feeling both embarrassed that I had put the school in a difficult position but also very proud that I had such a powerful ally as the school head! The headmaster said that he was sure that there would be a chance in the near future for me to thank him properly and I assured him that I would do anything I could to repay his trust and kindness.

Indeed, when we arrived at my home, I thought this would be an ideal opportunity to start to show my gratitude by asking him in for a drink, something that I would never normally have considered but I had also been drinking from a small hipflask that I had secreted away and been sipping in the boys toilets most of the day! I was quite merry by the time the headmaster thanked me for my hospitality and I showed him into the house and asked him to make himself comfortable in the lounge whilst I prepared some drinks.

Having the headmaster sitting in my lounge, whilst I made a couple of gin and tonics in the kitchen, was becoming quite a thrill for me. I couldn’t wait to tell my friends at school that I had shared an alcoholic drink with the head in my house. Indeed, I planned to get him very drunk so as I could maybe find out some other interesting facts about the other teachers and maybe even some of the pupils: information that I could use to my advantage later I was sure.

As I walked into the lounge, I found the headmaster seated on the sofa with our cat lying across his lap. He was stroking it affectionately and the cat was purring contentedly. Moving the remnants of my unfinished breakfast to one side, I placed the headmaster’s drink on the coffee table and sat down at the other end of the sofa. We then started chatting about the school in general, until the gin started to take effect and the head again started to talk about things that he should not really share, particularly things that some of the older boys had been up to in the toilets. He even mentioned some names and told me about the punishments that he had had to give them, including even the cane. It turned out that he had even been assisted by a couple of the women teachers on occasion and he confided in me that they really seemed to enjoy thrashing a young man’s bottom! I asked the head if that was across the trousers and he told me that, in extreme cases, he even had to order them to lower their trousers and pants and cane them on their bare behinds! I must admit to feeling a little excited about the vision of these naughty boys bent over the headmaster’s desk, their trousers and pants around their ankles whilst the head, with two mistresses watching, caned them severely across their backsides. As the gin had an effect on me also, I even had the courage to ask if he could see any of their private bits during the caning and the head told me that their hairy little ball sacs were usually visible and that sometimes the boys even got a little excited and their stiffening little penises would start protruding below their balls before standing to attention.