Age when it happend: 16
Where it happened: bedroom
It was the first day of term after the holidays, and after several weeks of being able to wear anything, I got up and put on the regulation uniform of grey shirt, striped school tie, grey jumper, grey shorts, grey socks, grey blazer, school cap and black shoes. I met up with closest friend on the way to school, and we decided to leave the premises at lunch time. At 4pm, we were summoned to the Headmaster’s study. We both had to wait outside, facing the wall, with our hands on our head. I could just see my friend’s blazer lifted up, revealing his grey shorts.
We were then called inside and, after a lecture, the Headmaster announced we would both be punished by both of us having our backsides caned. My friend was ordered to bend over, and I watched as the seat of his grey shorts become increasingly taut as he did so. The Headmaster then proceeded to lift his blazer before ensuring that the waiting backside was caned six times. I was then ordered to change places, and I could see my friend’s grey shorts through my legs as I felt mine tighten ready for the Headmaster to cane my backside another six times.
We were then made to sit cross-legged in the corridor until we were dismissed at 5pm. Walking home, we discussed what had happened and went back to his empty house. We were lying on the bed chatting until we both tried to cool the glow by rubbing the seat of each other’s grey shorts. We then started kissing and could feel the excitement as we reached inside each other’s pockets and took each other’s cocks out of the pants, so that they were both masturbated directly through the grey shorts.
After doing this for a few minutes, I got on top of my friend, he wrapped his bare legs around mine, and put his hands on the seat of my grey shorts. Our grey uniforms were intertwined as we started kissing more passionately and rubbing each other up and down before changing places. The seat of my friend’s grey shorts became alternatively looser and tighter as he moved up and down mine, our cocks rubbing together as they did so. The kissing and moving got increasingly passionate, and cocks increasingly big until I heard a loud moan and he pressed down onto my grey shorts and I felt him cum – the friction and excitement quickly made me do the same and I felt myself cum also in my grey shorts. We lay there for a while in each other’s arms, aware that both of us had cum in our grey shorts, but only caring about being together – the caning and cumming in uniform had bonded us even more closely together.