I must admit, I did go for some years - hard though that is to believe <grin> - not thinking that much about it, but the memory of that first caning was *always* a wanking favourite of mine whilst still at school (up to an including the sixth form, I'm afraid ... is there no hope for me <grin>?) and has, rather curiously, recently returned to occupy top slot! The thing about it was that, although I had heard others talk about canings (or 'twiggings' as our school slang had it), and had even seen stripes across other boys' arses in the showers or in the dorm <gulp>, I had never been near a cane myself, until then. So it was a mixture of fear and excitement (mostly fear, though <grin>) that gripped me when I was eventually brought to account. The three of us stood in a row in front of the head's desk while he lectured us. We had been caught kicking down a wall and reported to the school. Eventually, we confessed, thinking our honesty would somehow mitigate the inevitable punishment. Wrong! Anyway, after the lengthy lecture (are headmasters trained in that sort of thing?), he picked on my friend Paul to go first and told him to stand in front of his (the head's desk). I nearly had a cow when the head then told Paul to drop his trousers!
Now, it was usual to be given the cane across the seat of your trousers. However, I think the head could do what pretty much what he liked (short of killing us <grin>), so for particularly terrible crimes, he used to make boys take their trousers down. This was probably for two reasons. Firstly, it probably hurt more without even the modest protection afforded by grey flannel trousers. And secondly, and much more importantly I'm sure, it was *hugely* humiliating for the youth concerned to have to lower his trousers to have his bottom smacked 'like a naughty little boy.' This was particularly the case for stroppy adolescents in their midteens (of which, at that time, I am my friends were prime examples). Actually, I *think* that it was theoretically possible to get the cane across your bare arse, probably for _f_u_c_k_ing the head's daughter or farting in the choir <grin>, but, attractive as I found this idea, I didn't know of anyone who actually had <sigh>. Anyway, back to *my* story ...
The two of us watched horror-struck as Paul fiddled with the button of his long grey trousers (no-one still wore shorts at that age when I was at public school ... _d_a_m_n_ it!) and then pulled them all the way down to his ankles. He then bent over the desk and the head lifted his shirt up, so, except for his pants, he was virtually naked from the middle of his back to his ankles, where his trousers were bunched around his feet and his dark grey ankle socks just jutted up into view. Paul was without doubt one of the best developed boys in our year. He was very sporty and represented the school at rugger. Not that I tended to notice these things <ho, hum ...>, but he had a *lovely bum*! OK I confess. I was quite a connoisseur at that age. Well, it beat the hell out of stamp collecting <grin>. His was plump but not fat, if you know what I mean. *Very* curvaceous. He was most definitely 'lush.' And, as his trousers seemed at least a size too small for him (he was growing quickly), I used to notice how tightly they hugged the outline of his buttocks. It was all rather exciting for me at that age <grin>. But to see him bent over the head's desk, with nothing but a pair of *very* brief underpants to protect him was gob-smackingly, chest-thumpingly, _c_o_c_k_-swellingly amazing!!!!!!!!!!!!!
To complete the picture he also had strong, muscular thighs (all that rugger, I suppose <grin>) and shapely calves. Yeah, very lush. Very shaggable. Well fit. He was definitely grade-A wanking material, and I suspect appeared in quite a few guys' nocturnal fantasies. Oh, just so you know, his legs were also still silky smooth at that age. My legs felt like jelly, I was so scared. This was the thing I had fantasised about for ages, but now that I was actually going to get the cane myself, my desire almost entirely deserted me. I can clearly remember the headmaster (a powerful man in his forties) raising the thin, whippy cane high above his head and bringing it down with what I thought was a trememdous THWAAAAACK! right across the middle of Paul's buttocks. Paul gasped (I would have, and in fact did, yell out loud) and uttered the required, 'one, sir.' I was *totally* entranced. A bit like a rabbit caught in a car's headlights. I almost (almost!) lost my fear as I stood, fascinated, not four feet from where my hero was having his virtually bare arse whipped hard by the headmaster. Geezus, did it get any better than this??
As the head raised his cane for the second stroke (of six), I saw the mark left by the first one. It was long and thick, a raised red welt with (curiously I thought) a white centre (never have understood that ... oh well). It went right across the middle of his backside, with either end protruding out of his mega brief underpants. In fact, his pants were so brief and so tight (most went up his entrancingly deep bum crack) that his buttocks were, to all intents and purposes, bare. The other strokes followed, with Paul counting, in what I suppose was rapid succession. It seemed an age to me. The cane almost bounced off Paul's soft round buttocks, which were transformed from mounds of silky whiteness by the addition of angry red slashes. Paul certainly knew what a naughty boy he had been!
At the end, Paul was told to rise and get dressed. Then it was my turn. To be honest, I was on autopilot and just did as the head told me. I wasn't as brave as Paul though (oh the shame of it), and can remember almost begging him to stop caning me. The head was very unimpressed by my performance. He told me to shut up or I'd get double. I shut up. But I was virtually in tears (unlike my hero, Paul) at the end of my six strokes. I thanked the head and was also told to get dressed. Then it was the last boy's turn. Paul and I got to watch him get six across his 'knickers' too, with the sharp ache of our own canings burning through our trousers and pants. When we were dismissed, the other kid shot off somewhere, and Paul asked me to go with him to the bogs. I remember being a bit (!) surprised at this - I had intended to slope off somewhere by myselt to try and regain my dignity - but also pretty pleased that superhunk Paul actually wanted *me* to go with him. Although he was sort of a friend, I was still rather in awe of him. He was definitely one of the leaders of our year, and I was definitely a follower. So, true to form <grin>, I followed him like an obedient puppy to the junior bogs and we shut ourselves in one of the cubicles and very gingerly lowered our trousers and pants. I still remember how much it hurt even to have the material of my trousers rub my sore welts. Once down, we tried to look at our own bums, which was pretty difficult in an enclosed space with no mirror. However, we carefully felt our wounds. Then Paul asked me if I wanted to feel his. Christ! I'm amazed I didn't come on the spot. But I managed to retain some vestige of self control and mumbled something like, 'er, sure, ok.' I didn't want to seem too keen!
The funny thing was at my school was that, although virtually 100 percent of boys masturbated regularly, and I would guess at least 40 percent wanked with their friends, you weren't supposed to make a 'thing' out of it. It was an unwritten rule that we were only doing this because we didn't have any girls around. Yeah, right <grin>. Some of the keenest mutual masturbators in my year (including a vicar's son (!), who regularly led 'sessions' in the dorm after lights out) were the first to call other boys 'homos' or 'poofs' at the drop of a hat. The hypocracy was breathtaking! So, although I had admired Paul from afar, we had never actually wanked with each other. OK, the story continues ...
Anyway, almost trembling with barely supressed excitement, I put my hand under his shirt, which he then obligingly lifted out of the way to make my 'feel' easier. His bum was so hot I swore I could have made toast on it! The welts were very thick and very red, and stood out vividly against the smooth white background of the rest of his arse and his legs. I very tenderly stroked my fingers along the welts, expressing amazement he had taken his 'twigging' so well. Well, it wasn't the first he had the cane, of course, unlike me. He had been caned at his prep school and several times already at our school. Ahhh, the bum of experience! He thought I had done pretty well, considering it was my first time. That cheered me up enormously, and I asked him if he wanted to feel mine. Er, he did! His hands were so soft and gentle on my backside. It was the first time in my life that anyone had been so gentle with me on an 'intimate' part of my anatomy. I still, by some superhuman effort, managed to keep myself under control Which is more than he did!
When I turned round again, he had a massive (well it seemed massive to me at the time!) hard-on poking out at ninety degrees below his flat, smooth white belly. Althought his legs were still hairless, he did have a thick bush of dark pubic hair round his balls. He looked, well, *LUSH* <grin>!! He gave me an 'oh _f_u_c_k_ it' look, and started to wank! This was utter heaven! I couldn't believe it! Here I was, naked from the waist down, with one of the hunkiest lads in my year, who was also naked from the waist down. We both had sore red arses from a caning and now ... NOW ... this god was also wanking his erect penis, just inches away from me. I needed no further encouragement. My _d_i_c_k_ jumped to attention virtually instantly (isn't it amazing what you can do when you're young <grin>?), and I started stroking as well. At his suggestion, we 'did' each other as well. Weyheyyyyyy!!!!! It was brilliant! To finish, we took turns at kneeling in front of the bog while the other knelt to one side and tossed him off into it. It was a bit awkward with our trousers and pants round our ankles, but we managed. It was amazing tossing Paul off and feeling his spunk pumping out of his strong, hard prick and spurting into the bog. It was equally wondeful when he returned the favour for me. Needless to say, that might have been our first wanking session, but it wasn't our last.
So, if you ask do I still think about that first caning, I think you have the answer now <big grin>!