This is hands-down the most embarrassing thing to ever happen to me. I’m completely over it (well, kinda) and happy to share so no need to feel bad about enjoying it
I know if I had witnessed it, rather than had it happen to me, it would have been one of my favourite memories from school, instead of my worst!
I was in year 5 of primary school (UK school system), just before the summer holidays in 2000, so I would have been ten, or just about to be.
It was lunch break and my friend Daniel and I were by the boundary between the playground and ‘the field’ playing some kind of game I now can’t recall.
The field was pretty much that: a huge expanse of grass used for sports that we were also allowed to play on in the summer months, essentially extending the range of the playground by more than twice its winter capacity. It also went off at an L shape, meaning a large portion of it could not be seen by those on the main playground. The field was of course patrolled by teachers and lunchtime staff but for some reason not nearly as much as on the main playground.
We’d paused our game, or maybe we’d finished and Daniel went off somewhere, probably to use the (literal) little boys’ room. For less than perhaps thirty seconds I was alone and that’s when they struck. I don’t know if they had been watching us, waiting to pick one of us off as soon as one of us was alone—probably not, more likely I was just a random target.
From somewhere behind me I heard thundering footsteps and the very next thing, before I knew what was happening, never mind why, I found myself pushed over and tackled to the ground. A very brief tussle later, in which I could only put up minimal resistance, they had me flat on my back with my legs in the air and they each had one of my ankles seized firmly in their hands.
With genuine horror I recognised the two boys who now had me immobilised in such a vulnerable position. They were both in the year above me and had quite a reputation for being bullies and troublemakers. It was now very obvious why. In that chilling moment I knew whatever was about to happen, it was not going to be good. I was quite right.
Laughing, they spun me round, now facing the field, and a split-second later we were off. At full pelt they ran, dragging me helplessly behind them like a rag doll. The field must have recently been mowed as I can vividly remember all the dried out grass cuttings collecting around me and slipping up the back of my shirt, as it had become untucked during the struggle. It did not surprise me they immediately headed towards the L shape end, away from the prying eyes of the teachers.
Now, I don’t know for sure if what happened next was intensional on their part or an accident. I get the feeling they knew exactly what they were doing but I may be wrong. At the very least it would have been an unexpected bonus for them, as it made my experience a hundred times worse. They certainly seemed delighted with themselves and the way their little prank turned out.
My shoes were the first to go. Gripping me by the ankles and running across the uneven ground, bit by bit their hands had dislodged my black school shoes at the heel and eventually they had slipped off my feet altogether, laying discarded in the brown grass a few meters apart as the first fallen casualties.
Without the solid base my shoes had provided for them to hold my ankles, the two boys now had to readjust their grip or else their fingers would likely have slipped off over my socks. Seeing how easily my shoes had slipped off I knew I was now in very serious trouble when I felt their fingers close around the hem of my trousers. Without pause or even slowing down, on we went.
It was of course by this point inevitable. You cannot drag a boy by the cuffs of his trousers without expecting them to come down, even with the strongest belt in the world. At that age I did not wear any sort of belt, strong or otherwise. A second or two later I felt my school trousers begin to slip a little and real panic well and truly set in.
I reached up, grabbing my trousers just below the pockets and held on for dear life. This was not easy to do, hurtling along on my back with my legs in the air but initially I thought I could grip hard enough to stop the decent and total humiliation.
There were lots of kids around when it happened—girls, boys, older, younger, embarrassingly a large group of girls from my class—and not a single teacher in sight. Gradually, centimetre by centimetre, I began to lose the battle. My weedy ten-year-old’s grip was no match for two burly eleven-year-olds pulling me along by my trousers. My shirt had long since ridden up my back and chest to pool, mingled with grass cuttings just under my neck, so as my trousers began their terrifying descent, there was nothing in the way to hide any part of what I had on beneath. Everyone was going to see everything!
Even with just the waistband and first inch or two of my bright turquoise-blue underpants now visible I was more embarrassed than I’d ever been. For some weird reason I’d always been shy and really embarrassed when it came to my underwear being seen, or even talked about. Way more than most people, or so I thought. Some boys in my class just didn’t seem to care and were not hesitant at all about stripping off in the changing rooms or letting the waistband of their underwear show. This was not the case for me. Even back then in primary school I used to change for p.e. as quickly as I could, making sure to pull my shirt down low to hide my undies from view. It was also the reason I always wore my shirt tucked in, as even just the waistband of my underwear showing was too much for me.
Further and further my trousers slipped. By now almost all of my brightly coloured underwear was showing and I was practically bent double trying to cling on but I couldn’t keep it up for more than a few seconds. I can still hear the shrill, girlish laughter and shouts of surprise and excitement from all those around when I finally lost my grip altogether. It happened so quickly. The moment the grey material slipped through my fingers my trousers shot to my ankles and were gone forever. Well, that’s how it felt. I actually got them back about ten minutes later but those minutes were like an eternity. At least my extremely uncomfortable and bumpy ride had finally come to an abrupt end.
I couldn’t believe it. One moment I’m stood by the edge of the playground waiting for my friend to come back, the next I’m laying in the middle of the field with my shirt up around my neck and the whole of my pale, skinny body exposed, save for a pair of grey school socks and my bright turquoise briefs with a picture of a football on the front. Even at ten-years-old, these were in no way ‘cool’ underpants to be seen wearing, as the transition to ‘grown up’ boxers, that would grow ever more widespread over the coming months, had already begun among my piers. The typical mocking, childish laughter sprang up all around as everyone took in this exciting, naughty and highly unusual view. Looking back I can’t say I blame them, after all, they had just seen a boy dragged along by his trousers until they came off!
For a moment or two I couldn’t move, just lay there in shock, until a teasing comment of “nice pants,” or some such interchangeable remark soon got me moving as the crashing reality that I was basically laying on the field in my pants and socks hit home. I’d also recognised that voice and it belonged to one of the girls in my class. My face burned, knowing that girls could see my underwear—my massively embarrassing, football cartoon underwear, the ones I saved only for non p.e. days. I sat up and could see my two assailants running off into the distance, laughing their stupid heads off. One of them was holding my trousers triumphantly high and letting them billow out behind him like a sail.
Shakily I pulled my shirt down to securely hide my underpants and did my best to get rid of as much of the grass clippings as I could. I would still be picking bits out everywhere until I went to bed that night! Looking around I couldn’t at first see where my shoes had landed. I guessed we’d travelled quite far from where they came off. I was embarrassed at how long everyone stayed laughing but relieved no one came over to help. I don’t think I could have taken it someone had come rushing over to help me up. I just wanted to be left alone.
Once I’d caught my breath and the shrieks and laughter had died down I got to my feet, pulling my shirt down extra low like I did when changing for p.e. I didn’t fancy walking even further across the field in search for my trousers, which I may or may not have even found—I wouldn’t have been surprised if they’d been flung into a bramble bush or up a tree. I miserably headed back towards the playground, still pulling my shirt down with one hand and eliciting fresh laughter from those around who had not witnessed my stripping but were nevertheless titillated by the sight of a boy walking across the field without his trousers and shoes.
Fortunately I didn’t have to look far for my shoes as I soon found one in a clump of grass cuttings and then a friendly face arrived, the only person I wasn’t embarrassed to accept help from. It was Daniel, holding out my other shoe. Apparently he had seen the whole thing, having turned round when he heard the tussle, just in time to see me on my back about to be carried off. I slipped my shoes on and we walked back towards the classrooms, looking for a teacher to tell them what had happened. I was given a spare pair of p.e. shorts from lost property to wear until my trousers were found and Daniel ran off, saying he was going to look for them. I didn’t hold out much hope so was overjoyed when he returned a few minutes later with them hanging from one hand, brushing off the worst of the grass clippings with his other. To my great annoyance, putting them on I noticed a small tear in the seat from where they had taken the brunt of the rough terrane. It’s funny but at the time I can remember thinking how mad my mum was going to be that I’d ripped my trousers!
*
And now to my favourite bit.
The next day, during morning break I was summoned to the headmaster’s office, an occurrence only saved for when you or someone else had done something especially bad. Well, I knew two year-six boys who had been very bad indeed. Opening the door I was delighted and honestly a little surprised to find the two, supposedly tough bullies standing next to his desk with their hands on their heads, looking very sorry for themselves. It was clear at once they had been crying and I took enormous satisfaction at that. Quite what had been said before I arrived I could only guess but it had clearly had the right effect.
They were made to look me in the eye and apologise, still with hands on heads, which they did, if only holding my gaze for the briefest moment whilst blushing and looking very sheepish. I can’t remember all that was said next but I know our headmaster laid it on thick and before long fresh tears were slowly leaking down their faces.
Then our headmaster said some quite unexpected things which seemed to terrify them more than anything shouted at them so far. I could easily see why and the idea thrilled me. I can more or less recall every delicious word and how it made me feel imagining it.
“How would you like it if someone pulled your trousers off in front of everyone?” Our headmaster began.
They didn’t answer, just stared miserably down at their shoes. He pressed on.
“How would you like to be seen by all the boys and girls in this school wearing nothing but your underpants and socks?”
Again they remained silent, staring resolutely downward.
“You wouldn’t find that very nice, would you?”
Silence.
“Answer me,” he said calmly.
“No sir,” they mumbled.
“No, that wouldn’t be very nice at all. I think you would probably find that quite embarrassing, wouldn’t you?”
“Yes sir,” came their sniffling response.
This was so much fun. I could have listened to this conversation all day!
“You wouldn’t like it very much if lots of people were laughing at you in your underwear, would you?”
“No sir,” they sobbed.
Wow, he was really going to town with this! For a moment he caught my eye and I had the distinct impression he was phrasing these questions deliberately to try to embarrass them and that was fine and dandy by me. I’d heard from some of my friends that he had some rather unusual methods of disciplining his pupils but this was something else. It was amazing!
And then the killer line.
“Would you like to try it?”
Now their heads shot up hearing these words. They both looked absolutely horrified. I had a pretty good idea at this point our headmaster was just messing with them, trying to scare them to teach them a lesson. There was no way he would make these two boys parade around the school in their underwear, as much as I would have loved to see that.
“NO SIR!” They gasped.
I relished the look of pure terror on both of their faces. They clearly hadn’t seen through the bluff and genuinely believed at any second they were about to be given the terrible order to strip and march out the door. Both were crying hard again.
For perhaps ten seconds nobody said a word. I think, sensing that he’d done the job thoroughly enough now and these two troublemakers were well and truly broken, our headmaster finally relented his attack. I was absolutely buzzing from what I had just witnessed and more than a little tingling in a certain area.
“Now, I want you both to picture how you would feel in that situation and think about what you’ve done,” he said solemnly with a clear finality that indicated this humiliating meeting was at last over.
We were then excused and the two bullies excited as fast as they could, wiping their teary eyes with their shirt sleeves as they went. I followed casually behind them, smiling at how these tough year-six boys had been reduced to a couple of snivelling five-year-olds, both at the severe telling off they’d received and the seemingly real threat of having to spend the rest of the day in their underpants. I watched them until they were out of sight, imagining them running along wearing nothing but their underpants.
*
A few days later I was given a pathetic apology letter from them in which they attempted to explain it all away as a misunderstanding with the ridiculous line: ‘we were only carrying you as though you were royalty.’
“Yeah right,” I remember thinking, “what kind of a king gets carried like that?”
