skooliesstuff

[skooliesstuff]

A surprise encounter

I was out for a walk along the canal earlier in full school uniform. It's cold, so I was wearing a vest under my shirt and a jumper under my blazer, together with my shortest school shorts. On days like today, you really notice how exposed your thighs are to the elements. On an otherwise deserted stretch of the towpath, I saw a tall, older man wearing a suit and tie, heavy overcoat and fedora type hat, walking towards me. When we drew level, he stopped and spoke to me.

"I think I know who you are," he said, smiling down at me. "Do you have a blog called skoolshortz?"

"Er, well - yes, Sir," I said awkwardly.

He came much closer and patted the seat of my shorts, then ran his hand down one of my thighs and back up again.

"Lovely bottom and thighs," he said.

"Thank you, Sir," I said.

"Anyway, I spotted you, so I claim my prize," he said.

"What do you mean?"

"I mean your underpants," he said.

"What!?" I protested

But his right hand had already shot up under my blazer, darted down the back of my shorts and grasped the waistband of my jockey y-fronts. I tried to wriggle away but he wasn't letting go.

"Please feel free to struggle as much as you like," he said.

He pulled up hard, wedging my pants between my buttocks, then switched to a two handed grip and hauled them up further, crushing my little hairless bits in the front of my pants.

"Oh, yes," he said, as my eyes started to water.

He kept pulling up on the waistband of my pants, lifting me up onto my tiptoes, then right off the ground. At this point the seams started to groan and give way, and then there was a long, loud tearing noise, and my feet landed back flat on the towpath. He gave a last couple of hard tugs on what was left of my pants and ripped them off me entirely. I was bright red in the face by the time he had finished. He waved my totally destroyed y-fronts in my face and smiled triumphantly.

"A special pair to add to my collection," he said. "Now you run along, boy."

He gave me a forceful slap on the seat of my shorts to send me on my way, making me even more conscious of the fact that I was no longer wearing any underpants.

[skooliesstuff]

New year, same old disciplinary regime... I told my father I was too old for short trousered school uniform and also too old to be getting the cane. He said it wasn't a question of age but maturity. Or rather, my lack of maturity. Of course real grown ups don't have to wear shorts and get caned in them. But I'm not a real grown up, I'm an adult school boy, he reminded me. And I am about as mature in real life as a senior prep school boy or junior public school boy. That pre-adolescent age group is traditionally dressed in short trousered school uniform and traditionally disciplined with the cane. Hence the regime he has determined for me. I had to admit that made sense, so here I am in my tight little school shorts, waiting to have my bottom caned by him.

[skooliesstuff]

After serving the vicar a sherry and my father a scotch and water, I was made to go and fetch the cane. When I came back with it, my father instructed me to remove my blazer, bend over and touch my toes. The vicar commented on how supple I was and my father said that was because I got a lot of practice bending over. They both laughed, then my father proceeded to administer a serious beating, whacking his cane vigorously across the seat of my shorts eight times, the last few strokes making me really gasp and moan.

When I was allowed to straighten up, the vicar looked quite flushed. He said he had found the whole experience surprisingly stimulating and thought he should be on his way. My father asked if he wouldn't rather the boy took care of things. The vicar said that if that was all right, then yes. So I was ordered to get down on my knees and open wide. Almost as soon as the vicar put his cock in my mouth and I wrapped my lips and tongue around it, he spunked massively. It was a struggle to swallow it all but I managed. Afterwards, he patted me on the head and said he hoped to see me in church every Sunday from now on.

[skooliesstuff]

This was my uniform for Christmas Day. The vicar said I looked very smart and complimented me on the length of my short trousers. Then he asked me if I had ever been caned in them. I blushed and stammered, so my father answered for me, saying he quite regularly had to take his cane across the seat of my shorts to keep me in line. The vicar laughed and said that was something he would very much like to see. My father nodded understandingly and invited him back to our house for a glass of sherry.

[skooliesstuff]

Some guys find the sight of me being humiliated, then caned across the seat of my little school shorts strangely exciting. Because it's my fault they've got all "tense and uptight", as my guardian puts it, it's my responsibility to "relieve their stress". So I have to get down on my knees, very conscious of the welts across my backside, and open my mouth for them. They don't seem to mind that I'm totally passive in all this. Each guy puts his hard cock in my mouth and thrusts it back and forth between my lips and over my tongue until he shoots his load. Then I swallow it down and get ready for the next cock.

Sometimes after I'm done, people ask about my apparent lack of any sexual response. Occasionally, my guardian says he will demonstrate how I have sex. This is intensely embarrassing for me but I am unable to resist. He shoves his hands down the back of my shorts, grabs the waistband of my jockey y-fronts and pulls them up in a tight wedgie, crushing my bits, then keeps pulling them up between my buttocks until they are stretched way up my back and the seams are creaking with the strain on them. Finally, there is a loud ripping noise, and my y-fronts have been totally shredded. And then I make a little "ooh" sound as my still soft willy squirts in the front of my shorts.

And people say "is that it?" and laugh.

[skooliesstuff]

My guardian produces his classic crook-handled senior cane and instructs me to remove my blazer, then bend over and touch my toes. I am conscious that all eyes are on the tightly stretched seat of my school shorts as I comply with his instructions. And then he starts to administer the beating. I can't help stealing a glance at the audience after the first stroke lands with a loud and painful crack. Those who have seen this happen before tend to have either an amused or titillated look on their face. First timers tend to be shocked by how hard I get caned - a proper public school beating for a senior boy, regardless of how short his short trousers may be. If I am lucky, my guardian will stop at six strokes, and I will remain reasonably composed throughout. But he is quite entitled to give me the full twelve on any one occasion, in which case I will likely be snivelling embarrassingly by the end.

[skooliesstuff]

My guardian never canes me without an audience. He says a boy must be properly humbled for a beating to be effective. I have to stand in front of his guests in full school uniform, announce to them that I am to be caned, and explain why it is necessary for my guardian to punish me on this occasion. Blushing and stammering, I deliver my speech, and then politely ask them to please stay and witness my punishment. They always do, of course.

[skooliesstuff]

Bending over in my lederhosen, I felt like my bottom was pretty well protected. But our scoutmaster prides himself on administering effective beatings to boys wearing this uniform. He selected a long and thick but supple and flexible cane, then whacked it across the seat of my lederhosen unbelievably hard. Each stroke felt like it cut deep into my buttocks, making me gasp and yelp. And it was the loudest beating I've ever had. The whole neighbourhood must have known I had been caned. Suffice to say my bottom was covered with welts and bruises afterwards and I was a very sorry little scout.

[skooliesstuff]

At the end of a lengthy discussion about my behaviour on a recent scout camp, I discovered that my scoutmaster has an extensive collection of rattan canes and that my father has given the necessary authority for their use on me.

[skooliesstuff]

I'm proud to say I've joined an international scout troupe. The uniform includes these very smart lederhosen.

[skooliesstuff]

My housemaster reminded me that the length of my short trousers is directly related to my level of emotional, psychological and sexual development. Hence they are very short indeed. At the same time, he did say he appreciated my authentic immaturity, as it meant he always had a genuine reason for disciplining me. Apparently, this makes whacking my bottom with his cane especially satisfying. I guess I'm going to have to grow up a bit if I want longer shorts and ever want to be able to sit down comfortably in them.

[skooliesstuff]

I said I was sick and tired of being endlessly patronised by all the real adults around me and that I was striking from schoolwork until I was allowed to wear longer uniform shorts. My housemaster said that I was mistaken and that it was he who would be striking - striking the tightly stretched seat of my little short trousers with his rattan cane.

[skooliesstuff]

Having another one-sided conversation about my behaviour, after which I will be invited to remove my blazer, bend over and touch my toes for the cane.

[skooliesstuff]

When people who know me in another context first see me in school uniform, they tend to lose a little respect. It's hard for them to take a twinky young guy in school shorts, knee socks and the rest entirely seriously.

But when they see me under the authority of a real grown man, bending over at his command and having my bottom caned by him, they are shocked and amused in equal measure. And once they've seen me disciplined like that, they can't take me seriously at all.

It is humiliating for me, of course, but it's for the best. The more people who know I'm just a silly little short-trousered schoolboy, the easier my life gets.

[skooliesstuff]

Whenever I report to a master who I think is wet or weedy, I remind myself that all masters cane and that some of the most effete cane the hardest. They are the ones who betray the greatest enthusiasm for caning boys' bottoms, who really relish administering a beating. As an adult schoolboy, I think it is especially humiliating having to bend over and accept being disciplined by such a man. But I have to agree that such discipline puts me in my place most effectively.

[skooliesstuff]

Is it possible for you to misbehave so badly that it could result in your spanking to be administered with your shorts lowered? Is it possible to even to get it with both shorts and underwear lowered? 🍑

Yes, that has happened on occasion.

[skooliesstuff]

Time seems to stand still while I'm waiting to be punished. I am supposed to be thinking about what caused me to end up in this situation and regretting my behaviour. But I am mostly thinking about how short and tight my school uniform shorts are and how painful it is to be caned in them. The beating itself will only take a couple of minutes but the stripes will last for weeks.