THE SCHOOLDAYS OF DAMIAN SIMONS
CHAPTER 2

High School:
The Cane At St. Cuthbert's


When we were at St. Martin's we had been dazzled with stories from older boys about high school canings. Graeme Lamport was one who had plenty of stories to tell and from him especially I had a better than vague idea of how it all worked. He used to demonstrate the joys of being at St. Dunstan's by bending Wayne and me over and having a go at us with the cane handle of a feather duster, a game in which he was only allowed to hit us if we could whack him back.

showing weals After a caning at St. Dunstan's Graeme used to show us the real thing. A few looks at the fresh, livid stripes across Graeme's buttocks after school persuaded us that the worlds of St. Dunstan's and St. Cuthbert's (my intended secondary school) promised spectacular entertainment.

Demonstrations on pants, underpants and naked buttocks produced hours of harmless fun at the Lamports' place, especially when I stayed there overnight. We would carefully check the marks on our bums, to see if we owed the others a harder one than the ones we had received, but there was seldom anything to write home about. We were too cautious, Graeme grumpily pointed out.

The game of caning created an air of sexual excitement between us which often resulted in frenzied mutual wankings. Graeme made the most of any opportunity to show off his superior size and maturity, teaching us new tricks all the while. During one fabulous bed-time demonstration of the facts of life, he rammed his aroused tool into a pillow until it spurted forth joyously. As his climax subsided we were surprised by Dr. Lamport who could not have looked more horrified as he came through the bedroom door, pointed at the sodden pillow and took in our aroused nakedness. He ordered us back in our pyjama pants, only to lower them again for a strapping, bent over our beds. My immunity to his strap being applied to my bare arse had expired, it seemed. Graeme took the most serious thrashing but each of us was thoroughly reddened up.

When Mick and I finally got to St. Cuthbert's, reality exceeded all the notions planted by Graeme's St. Dunstan's stories. Induction into the ways of the high school cane was immediate. Mick and I, with others, were soundly trounced and got to see three older boys caned in the course of our very first day.

Our class, 36 twelve and thirteen year old boys just getting to know one another, was waiting noisily in a corridor for the teacher to arrive and let us into our classroom. 'Crusty' was teaching in the neighbouring classroom and stuck his head out of the door to command quiet. We all stopped talking but after a while the noise level rose again. Crusty reappeared, demanding to know who was creating the racket that was disturbing his class. Everyone was talking, but five of us were silly enough to put up our hands.

He sent us about ten yards along the corridor while he disappeared into his classroom, re-emerging moments later with what we had all heard about but never actually seen - THE CANE ! It was about a yard long and as thick as a man's ring finger, much longer and meaner-looking than the duster handle Graeme had whacked us with !

As he came towards us with the cane he sliced the air noisily with it. The boys who were merely observers of this thrashing were naturally delighted to see the cane in such early use but we could all estimate its painful potential from the look of the thing. My palms were sweating and I struggled against a sudden weakness in my knees.

ready for it 'Butter' Bates was the first cab off the rank. A pudgy, unmanly little fellow, Butter looked pathetically like a baffled overweight fawn when Crusty pointed the cane to the spot where he should stand. He placed his little feet where he was told, with his back to us. We heard Crusty, in the gentlest of voices, say: "Bend over then, laddie." Encouraged by Crusty's kindly goodwill, perhaps deciding that such a nice man wouldn't really hurt him, Bates struggled into the bent-over posture. Crusty coaxed him further. "Bend right down, boy - I want your head below your knees - feet together."

And so Bates' little bottom was pointed up expectantly, his shorts puckered up between his chubby thighs. Reaching now into the sleeve of his academic gown, Crusty produced a stick of chalk with which he made a stripe about 4 inches deep across the fat little cheeks of Butter Bates' trousers. We were all mesmerised.

Having replaced the chalk back in his sleeve, Crusty took about five steps back. He squared up like a bowler at cricket. Then he took a run, cane raised over shoulder, before sweeping it down on the carefully prepared arse of little Bates. As it swung through the air the cane made a sound not unlike the powerful swing of a golf club - a deep, almost throaty Whoap ! (to rhyme with soap). Instead of the pop of a club hitting the golf-ball, however, it came down with a mighty crack - like a shot-gun - and the whack echoed off into the distance through the corridors. Something in the pit of my stomach lurched, like being on a roller-coaster ride. Crusty was going to hurt me.

When it impacted on Bates' backside, a cloud of chalk-dust rose in the air and a neat stripe was left where the cane had landed. Poor old Bates stood bolt upright on agonised tip-toe and emitted a loud squeal. He grabbed his bum cheeks with both hands and, with a terrified, tearful expression, looked pleadingly at Crusty. Tears, I discovered, were unavoidable when being caned, however brave one was. It wasn't that we cried. It's just that our eyes watered with the shock and pain. But Bates was beginning to really sob. Crusty, however, was equal to the challenge.

In a matter-of-fact way Crusty said: "Did I tell you to stand up, boy ?"

"No sir," squirmed Bates.

"You're at St. Cuthbert's now, laddie. Better learn your manners."

Butter Bates was then bent over again, really sobbing now, and skittish about getting right down. But Crusty tapped him gently behind the neck with the cane, in an almost comforting way, until Bates had bent low enough. He took his five paces back and fired another shot of the cane. Bates got four strokes in all and Crusty had to nurse him through them all.

By the fourth stroke Crusty had somehow taught Bates to get the mastery of his own reactions and successfully brought him through without catastrophe.

Bates' subsequent canings at school were utterly without incident, including one that followed within days. Reflecting on all this, I have some respect for Crusty, who could have completely unmanned Bates by letting him off lightly, or by leaving him as an object of ridicule before his peers. As it was, Butter Bates' beating initiated him into the fellowship of the 'real men' amongst the boys and it was Crusty who did it.

mass caning A boy called Dempster was next. Dempster was what every mother would be happy to call a good boy, unlike Mick and me ! He had a polite, choir-boy manner, jet black curly hair, delicious olive skin and dark, melting eyes. Dempster's brilliant little arse was chalked up and the cuts were laid on. This was more like it ! Dempster's only reaction was a slight quiver as the shock of each stroke registered and a proud if watery look as he returned to the class.

Who was to be next ? Mick and the Rollo made no move so I took a deep breath and stepped forward. Desperate to get it right I moved into position almost before Crusty told me to.

"No need to rush, laddie," he said.

A pause. Crusty was in control.

"What's your name, boy ?"

I told him.

"Bend over then, Simons."

I felt the chalk being swiped across my trousers and then the coolness of the cane gently at the nape of my neck pushing my head down lower. I thought I was down lower already ! When I had bent down almost off balance Crusty's footsteps receded away from me.

Then: "Feet together !"

I waited. I thought something had gone wrong. He wasn't coming.

Then I heard his urgent shuffle as he launched himself at me.

The rest was in slow motion, like a car crash.

WHAM ! I heard the cane land before I felt it. I even had time to think: "well, that wasn't so bad."

Then the pain started. It was like a shock of high voltage electricity. It didn't rest on my backside but burned its way through my whole body. I was on fire with it. With all this came a huge adrenalin rush, coursing through me the way it did at sprint races, when the starting gun fired.

It took all my will to stay there, bent over, and I wondered if I would manage the three yet to come.

As it turned out, the subsequent strokes didn't make the pain worse. They simply prolonged the first agony. If you can manage one, you can manage any number, I realised, so long as you can maintain the posture, and so long as the strokes aren't applied too slowly (with a long pause between cuts). When it was over, I was sent back to the class group watery-eyed, exhilarated, but still stinging and desperate to run as hard as I could. All that adrenalin was still looking for a place to go.

Rollo was a big boy, a bit older than the rest of us, and he took his flogging without fuss. He showed us later how one of the strokes had landed at the top of his legs, which he said hurt more than the others.

Mick was the last to bend over.

Mick and I were, as I have already told you, special friends from primary school days. Though I was too naive to realise it then, I was and had for years been desperately in love with him and had a passion for his perfect boy's body. Mick was a blond god whose beauty improved through his school years. We had explored and stimulated each other thoroughly in what had become a matter of habit. I loved the way his nipples were always erect, and showed through his shirts. I loved the way his sex stood up in my hand, and flicked back onto his tummy like a mousetrap when I let it go, making a little slapping noise. Indeed I was in love with every inch of Mick, including that sweet little pink humid place he hid between his buttocks and which now, though trousered, was the focus of 35 pairs of eyes.

Preoccupation with my own screaming bum gave way to emotional ambivalence at the sight of Mick's bottom being prepared for a thrashing. I didn't want my beloved Mick to be hurt, yet at the same time I wanted it very much. I had watched various versions of floggings of Mick in the past but there was something differently exciting about the cane.

bending over in style Mick took on the role of boy-for-beating with tremendous style. When Mick bent over, his bum stood proudly and pertly up, which set the tone for all our subsequent canings. Seeing his proud arse pointed up so magnificently, I was disappointed not to have thought of it myself and made a mental note to copy him if I ever took another caning. Little did I know how many canings I would receive over the next five years !

The trick Mick had was to bend his knees slightly and point his bottom up as if to be kissed, or like a cat waiting for a Tom - something only boys and nubile women can manage with any style. Mick thus cheekily, provocatively, accentuated the sexy lines of his adorable arse. This is a very difficult posture to maintain for the duration of a caning because you just want to straighten up, but it was wonderfully delicious to see and, I discovered, very sexy to do.

While I was watching Mick's beating on that first day I got a raging erection. My cock was pulsing like crazy. I was ashamed at the time but later found out that many and perhaps most of the boys got a hard-on when they watched punishment, especially of a beauty like Mick. I know, because I used to surreptitiously check out their swelling crotches.

There was a wonderful sweetness in the striping of Michael Watts' lovely bottom.

After we got home from school Mick and I got our pants off as fast as we could to see what marks had been left by the cane. Four gorgeous pink welts had been laid on us and they stayed there for about three days. We looked at them in the mirror and basked in the glow of mutual admiration. Mick's were indeed very fine stripes on a first class bum. Having been beaten, I felt we had passed through a splendid rite of passage and I glowed with pride in it. We phoned Wayne to tell him the news. Yes, he'd seen the cane in use at St. Dunstan's as well, but not on him.

The next Saturday afternoon, however, Mick and I were over at Wayne and Graeme's place looking at the damage on both their arses. St. D's had Saturday morning classes, and Graeme and Wayne had for some reason been flogged together almost as soon as they arrived at school that same day. Four was the order of the day at St. Cuthbert's, except in the boarding house where anything was possible, but St. Dunstan's were routinely into giving six of the best. Graeme and Wayne won in the one-upmanship stakes for the time being.

We also, as I said, saw three fifth formers caned on our first day at St. Cuthbert's, caned in front of our class for some earlier misdemeanour. They were wearing shorts but they seemed terribly big to me, with hairy legs and deep voices.

bending for the cane We were all sitting at our lesson when there was a knock at the door and the boys were told to come in.

The master said to them: "You've come to give these little lads a floor show, eh ?"

He bent them over one by one and gave them four each. There was no chalking but the dust flew from their pants anyway and clear stripes were laid where the dust had been raised. All very matter-of-fact. It was over in no time and they were sent off to their classes.

We became accustomed to this teacher's 'floor shows' over the next few months.

"OK, boy, time for a floor show," he would say, and some fellow would have to go to the front and bend over. He was a great whacker who had me up the front for quite a few performances during my time in his class. "Floor show time, Simons !" he would say, and leave me bending over ridiculously with my bum chalked and ready for action while he finished whatever he was doing.

"Get a good look at Simons' noble backside everyone. You have to hit it every now and then to get his attention. Isn't that so, Simons ?"

"Yes sir."

More waiting while the teacher droned on and the class mentally undressed me.

Then would come the whacking and he'd say: "Sit down if you can" and I'd go back to my place stinging like crazy and wriggling round on my seat till the pain subsided.

caned in front of the class I discovered that witnessing the caning of boys from other classes was not unusual, especially at the weekly music periods with which our Fridays began. The music master was in charge of the whole school for hymn-singing practice before morning assembly, the first event of every day. Misbehaviour was rewarded with caning, occasionally on the spot, creating a great spectacle while a thousand boys craned their necks to see the walloping.

More often, though, the culprits were sent to wait outside the music room until after assembly. Boys were therefore treated to an exhibition of multiple canings every week when they came to music, if they had music for first period, that is. The music master's canings were so frequent and so absurdly frenetic that they were not taken entirely seriously. This is fascinating, because I was on the receiving end of plenty, and can vouch for the fact that he could deliver a stinging stroke.

The music master was a weedy little man who put the strokes on with the pace of rapid machine fire. The cane used to bounce off those bottoms so fast that we could barely see it. It was not unusual to begin a music period by watching a dozen or so boys being beaten - all from different levels of school seniority. Great big fellows, much bigger than the music master, were bent over in line with little third formers and the music master would pound away at their backsides with abandon. Sometimes we knew the boys being beaten and there would be winks and smirks exchanged behind the music master's back. Mick and I had more turns than most - at one stage bending over for them several times a week. We feigned indifference to the whole thing.

I didn't mind too much being beaten in front of older boys or boys my age, but as I ascended through the school seniority, I found it a bit embarrassing to bend over in front of third formers. As I will recount later, during my last term at school I was one of the star attractions at a caning in front of a huge mob of them.

amazed expression Another notable multiple caning I saw was when, in fourth form, I had to go to the staff room on some errand during the lunch hour. A master called Mack was at that delicious moment about to cane a whole class of third formers. For a sweet ten or fifteen minutes they were blocking the staff room door and I watched them being doubled over one by one and given what they deserved. Because this was a class punishment, it had obviously gathered up the relatively innocent among the hopelessly guilty, and some of the boys in line were not among the habitually beaten like Mick, me and so many others. Their relative inexperience showed itself in their hesitant bending and amazed expressions when they stood up again.

I got into a few mass thrashings myself. For example, the Under Fifteen football team, all muddy and sweaty, got a flogging from Mr. Delbridge the day we booed the referee. The ref. was obviously on the other team's side and we all got fed up with it. While the other team watched from their departing bus, Delbridge gave us four of the best just outside the Pavilion, and the referee, seated on a bench, had the satisfaction of watching the cane spray stripes of mud off our bent-over bums.

bending smartly, a row at a time Another time was when Ratty had gone out of the classroom and we used the casing of our ball-point pens as missile launchers, firing ink-impregnated balls of blotting paper at the ceiling. The effect was colourful, but Ratty was not amused. He got a boy to go up on the desks with a cane to flick the offending art work off the plaster, then laid the stick about our arses without pause, dusting each of us up with a duster first, and muttering all the while about how useless we all were. We had to file out a row at a time and bend smartly into position when it was our turn.

I digress again. Returning to my narrative of first year high school, I must tell you about my second experience of being caned which happened about ten days into the first term.

During the second and ensuing three weeks of every year the school became an army unit. We were all squeezed into khaki shorts and tunics that our grandfathers probably wore when they were at school before WWI. We were fitted out for these uniforms at a barracks where we queued in our underpants for an army officer to guess our size and give us shorts to try on. If they buttoned up, they were deemed to be a good fit. The tunics were buttoned onto the shorts, which hoisted the already tight pants up into our crotches and into the parting between our cheeks. Because they were already tight-fitting in third form they were almost impossible the following year. At the beginning of fifth form the uniforms were returned and exchanged for other ill-fitting garments that had to see us through the rest of our school lives. Bulging crotches were fashionable then and we wanted everyone to see what we had. In those days we thought tight shorts were pretty good - the tighter the better.

In any event, in my second week at high school young khaki-clad Cadet Damian Simons was bent over an old-fashioned low student's desk for four slow strokes (lots of time between each stroke). I could feel the stretching of the fabric tight around me as the tunic pulled the trousers up into my cleavage and squeezed my sex up almost to my chin. With my chest on the desk and hands gripping its legs I arched my bum up for that thrashing as Mick-like as I could, arse cheeks tensed and pointed up ready for a licking. It was really hard to take the slow caning well but I managed it. Each stroke left me breathless as the fire of the cane surged through me. Between strokes I was relaxing and tensing my cheeks to try and shake off the pain, but I made sure they were tensed when the whacks landed. This was my innovation to add to the Mick routine.

I showed off the stripes to Mick who admired them generously. It all ended with cum on the bedroom carpet and stains on the khaki.

showing stripes The stripes left by our school canings were never serious - they weren't what you'd call wounds or anything. They were just pink stripes, starting off raised in a welt but fading fairly quickly. Fifteen minutes after the punishment we felt no tenderness or pain but for ten minutes it was dynamite ! The bedroom mirror was usually the first to see my stripes when I had them, and I used to check each day to see how they were lasting. Sometimes, if a teacher went out of the room, we would drop our trousers to show our stripes to classmates or, if modesty prevailed, hike our shorts up to reveal a well beaten buttock.

As well as Mick and Jamie (more about him later), I had another stripe-comparing companion in the boy next door, Alistair, who went to St. Dunstan's, the same school as Graeme and Wayne, and with whom I competed in retailing often exaggerated caning stories.

Alistair was ginger-haired and freckled and had an outrageously large banana-shaped cock. This noble appendage always came alive, like mine, long before the preliminaries of lowered trousers, or the occasional raised kilt in his case, and stripe inspection. Alistair had a commendable lack of inhibition which he attributed to late night sessions at Boy Scouts' camps. He could ejaculate for what seemed like yards and enjoyed demonstrating this with an urgent squirting of the mirror from an impressive distance. We used to joke about 'all those little Alistairs' sliding down the mirror in gobs of cum.

He was runner-up in the Boy Scouts distance finals to Peter Sanderson, who lived a few doors away and who also had a splendid grasp of things. Alistair was able to describe Peter's equipment to me in detail long before I met it in our swimming pool. Alistair also had a working knowledge of his other Boy Scout confreres' weapons and how and what they could discharge, and delighted in retailing all this information to me. It was Alistair who first showed me 'where it goes' - which he demonstrated by straddling my backside and putting it into me.

After a few of these sessions we graduated to the point where visits with Alistair often culminated in a cum-filled bum or two. All this, he said, was standard Boy Scout stuff and didn't reflect on a boy's 'queerness' or not. It was good practice for the real thing. As he shoved his way in between my reddened cheeks he said he was thinking of girls. I knew even then that he had Damian's arse on his mind and nothing else, but I let him think he deceived me. He wasn't so keen on reciprocal anal visitation rights but his sense of fairness compelled him to acquiesce, grimacing and gasping, to poundings from me. His tool was bent, after all, where mine was straight and, as I had done my bit without complaint, he could hardly refuse.

St. Dunstan's was another rather posh private affair like St. Cuthbert's where liberal applications of corporal punishment were promised in the prospectus. Parents who wanted their boys turned into men struggled to pay huge fees for these expensive whackings, especially at St. Dunstan's. Their uniform was normally a suit and tie but some army cadet units wore kilts during the cadet season, just as we wore khaki.

Alistair's best flogging story involved himself and some others being bent over a wall-desk, their tartan kilts being lifted by the master's cane (this required some dexterity given the length and weight of a kilt) and their white underpants or cotton shorts being chalked with a duster before taking six of the best with a lavish run-up. Alistair claimed that one particularly recalcitrant youth in this batch was made, after misbehaving through the first few strokes, to drop his underpants and take the rest on his bare rump. He also maintained that it was not unusual for a boy to have to hoist his underpants into the cleavage of his buttocks, so as to expose them. I could not verify the bare-rump part of this story then and cannot now, but I think it was probably true.

caned with pants down

I understand that borstals in NZ were heavily into pants-down caning at the time, and when I became a housemaster at St. Cuthbert's I discovered that anything could happen, including the St. Cuthbert's 'rumpings' (more below about that). Perhaps a few eccentric staff felt that a few stripes across naked cheeks added to the parental money's worth. Day boys at St. Cuthbert's were never treated to such an extravagant luxury.

Alistair's stripes were a frequent and wonderful source of entertainment to me. I loved lifting his kilt to peel the funny little shorts and underpants off him, tracing the welts with my hand and parting his cheeks to surprise him with an erring finger. On one delectable afternoon he revealed that he had gone naked under his kilt all day because he liked the feel of the breeze on his balls, hoping like hell he wouldn't get caned. That day the cum was all over his kilt almost before I got hold of him. He was terrified of what their housekeeper would make of the resulting mess.

Every year the whole school stopped while our First Rugby XV played the First XV from Alistair's school. This was a major event to which parents came and in which everyone participated as a player or spectator. During one match, a St. Dunstan's forward had his shorts ripped, revealing not only bare cheeks (he was wearing a jock-strap) but a thoroughly and recently caned arse. The caner was an artist, for there they were - six stripes which looked as if they had been painted on with a pink felt-tipped pen, all in perfect symmetry and precisely parallel. The match spectators saw this magnificent sight long before the referee, who was engrossed in the play. Mothers were feigning embarrassment. Fathers, on the other hand, were yelling out: "bend over laddie", "take another six" and so on. The boy himself was one of the last to know how much entertainment he was providing and it was a St. Dunstan's master who eventually ran on-field (to a subdued booing from the Dads) to haul him off and fit him up with borrowed shorts.

Alistair's father was an old boy of St. Dunstan's and he charmed us with stories of his days as a caning prefect. He told tasty tales about the raised-kilt caning of the arses of junior boys, who had to bend over the arm of an upholstered armchair in the prefects' common room. They took a beating for the offence they had committed and then an additional stroke for the imaginary crime of wearing shorts or underpants under their kilts. On some occasions the prefects would aim to have a bottom each to cane. After taking their strokes the caned boys all had to lift their skirts or drop their pants and bend over so that the assembled prefects could compare the results. This business provided a bit of a sport for the seventeen-year-old prefects, who also compared the quality of the arses as such. The caned boys, instead of resenting this treatment, tended to side with the prefect who had beaten them, determined to have been beaten by the best. At least that's what Alistair's Dad said.

caning prefect St. Cuthbert's had caning prefects until the early 1950's, the lack of which in my time was some disappointment to me. I rather fancied a session such as Alistair's Dad had described. Either end of the cane would have been fine. The closest I came to all this was a beating from several of our boy tennis coaches, including the lovely Tony Saddler, who was a first year university student, barely shaving, during my Upper Sixth. But I got my own chance to flog a few arses when I inherited the coaching job myself ten months later, and to smarten up countless juvenile rear ends when I became a junior housemaster.

When I got to Sixth Form Tony Saddler, a year ahead of me, was a prefect and a cocky C.S.M. in the cadet corps. He was a conspicuously handsome cadet who looked fine in his well-fitting cadet shorts, tunic and Sam Brown belt. But he was positively splendid in his tennis whites, and he knew it. It was unusual to be caned during sport (as opposed to gym classes), but Tony caned Jerry Calder and me because he caught us having a pre-match smoke behind the tennis pavilion. (Those cigarettes again !) It was either Tony or the Head.

"I'll have you two in B9 (a classroom) straight after the match," he told us. When the time came he considerately asked us if we wanted to put underpants on (we only had jock-straps under our tennis whites), but we had to refuse the offer as neither of us had any to put on. We followed Tony Saddler's excellent eighteen year-old rump over to the classroom.

"How will you have us sir ?" asked Jerry.

"Simons can organise a desk, thankyou Calder," was the response.

I positioned the desk for Tony while he ratted around to find a cane. He found a new, very sleek number.

Then he bent us over, Jerry first then me, and laid the cane on.

bent over a desk The sunniness of young Tony's open face didn't dim one iota as he stroked Jerry's neck, back and arse with the cane to get him in position then started his run, ending with a leap in which he virtually flew at Jerry as if he were belting a ball at the nets. The legs of Tony's pants had ridden up above his thigh muscles, accentuating his manhood in which I detected a definite stirring.

Jerry exhaled an urgent, spunky little gasp each time the stick met his bottom. His pink bum, damp with tennis sweat, winked through his shorts as he took the beating, so transparently that I could see the contrasting paleness where his sun tan had been blocked by speedos. All a bit of a turn-on even though I was waiting for the cuts myself. Standing up, Jerry's shorts stayed saucily stuck to his tight little peaches where the cane had landed, the legs of his pants also having risen up in a bunch round his balls.

When I bent over I gave Tony Saddler the most seductive arse display that I could manage, clenching my cheeks with an expertise that had become second nature to me. Tony rose to the occasion in every way, whacking me up generously - running, leaping and landing the cane joyfully on my oft-whipped arse. While we were changing afterwards I discreetly made sure that Tony saw how magnificently he had done the job. Although he feigned indifference, I know he was grateful.

When I went to university I succeeded Tony Saddler in the coaching job at school and had to put a few reluctant stripes across bottoms myself, including those of the Upper Sixth former who followed me in the job ! Andrew Coggins and his mate Holloway were among those who took it from Mr. Simons, tennis coach, over the same desk as Tony had used for Jerry and me. Perhaps I might tell you about that, and my housemastering years, later.

I mentioned earlier the panache with which my good mate Mick took his beatings. When we got to our senior years at high school Mick's sense of style was perfect.

When caning a boy in a suit, the master would always lift his coat-tails with the cane, to expose the target area. Mick had a lovely way of flicking his own tails up with both hands at the same time as he pointed his arse in the air. It was a very flash gesture and I noticed that a few of the other senior boys copied it. It cheated the caning master of part of his own ritual, but it was a turn-on. When I flicked my own coat-tails up for a caning I used to try and catch the eye briefly of the flagellating master. Sometimes we exchanged what I now recognise was a salty erotic look.

Caning had the effect of bonding boys to their masters in a curious way. It also bonded boys to one another, like poor old 'Butter' Bates who may never have 'belonged' without becoming a veteran hero of Crusty's cane on the first day.

hands on knees Caning at school was generally administered on the spot, in front of the class. However, it was not unusual to be sent into the corridor where the master could get up a decent run before delivery. Hundreds of boys would hold their breath behind the closed doors of classrooms, as we listened to first the run-up and then the wallop as the cane landed on some boy's bottom. Sometimes a master would enter into the fun and allow his class a soft "Oooh !" sung out in muted unison after the sound of impact in the corridor. The corridor acoustics made these unseen beatings highly dramatic. There would be sympathetic murmurings when the count went above two. A four was almost applauded. Occasionally the sounds of caning would go on and on as a largish group was being beaten outside in the corridor. It sounded like prolonged cannon warfare. On one occasion a master even opened our classroom door so that we could crane our necks into the line of sight and watch the fun.

Mostly, boys were simply bent over with their hands on their knees and with their elbows folded out, which is what we preferred. Sometimes they had to grip their ankles, which made balance difficult. Classroom canings were generally administered with the boy facing the blackboard and with his bottom facing the class, but it could happen the other way around, or side-on. The face of a boy being caned gave great amusement, but the rear view was highly satisfactory and preferable.

over the desk The bending of boys over a student desk always looked good from behind as the desks were low enough to encourage bottoms to be pouted up. Over-the-desk canings in the classroom generally meant a boy in the front row having to vacate his desk, which was then either pulled out onto the floor where the boy bent bottom-towards-class, or the boy might simply be bent over the desk where it stood, and we would watch his face instead.

One science master preferred his boys over a laboratory stool, gripping the rungs, head down the other side, and standing on tip-toe on account of the height of the stool. This was great fun, especially when the force of the cuts moved the stool fractionally across the floor, obliging the boy to push his chalked and striped arse up as he did a little ballet step to get back in position for the next stroke.

To be caned at gym was very serious indeed. The gym masters were extremely athletic, always took a short but lethal run when they caned, and enjoyed the advantage of caning through flimsy gym shorts. These were little sexy things and the older we were the less cover they provided. Some boys being caned at gym took their beatings on partially exposed buttocks because, as they bent over, their tight shorts rose up their bums, showing a flash of underwear, or the bum cheek-loops of a jock-strap, and lots of naked bottom. The upper part of the bum cleavage often came into view as well during these gym-shorts canings, creating a thoroughly inviting effect.

caned in sports shorts Gym canings were a delight to watch but misery to endure. One was sent up to the mezzanine to get a cane from the pile on the masters' lockers. Choosing the cane least likely to hurt was an interesting exercise. There were splendid new ones and crooked, tired ones, but they all felt the same when applied to a boy's rear end. I can attest to this after trying to get it right over a five year high school career.

We had two gym masters. Mr. Cornish was an older, sergeant-major type, very strong and alarmingly nimble. The other gym master was Mr. Terry. He was a very junior master in his first job and a national gymnastics champion. Mr. Terry's runs-up were executed with a light skip across the gym floor at terrific speed. His sting was deadly but we all thought he was great in every way - as well as being an Adonis, he was a bit of a comic and brilliantly friendly.

Changing after gym periods, a caned backside was eagerly inspected by the rest of the class, and the gym masters' prowess as caners was confirmed by the strokes which had been landed in neat, evenly spaced welts. It was not unusual to find a row of boys lined up in change-rooms with their pants down while we compared stripes (and concealed our erections).

I still had Mr. Terry's stripes all over me one day when I found myself showering next to him. "Not bad, eh ?" he said from a couple of yards away. "No sir," I replied, wondering whether he meant the hot water, the welts he'd given me or my stalk which was swelling up accusingly. Or perhaps he was talking about his own prick which at that time was draped over his hand for a soaping.

over the horse

A gym period in summer was often spent at the swimming pool. We all had to wear speedos in the school colours but sometimes boys turned up without them and had to swim in their white Y-fronts. These were spectacularly sexy when wet and I was not the only one in my class who enjoyed forgetting my speedos. One grim day Mr. Cornish, having lost all patience with juvenile forgetfulness, caned me beside the pool, with another amnesiac, in our underpants.

He was good at laying on the strokes and our Y-Fronts afforded very little protection. I didn't know whether it made much difference to the quality of the stripes, but we were very cocky about them when we showed them to the others. Jamie was part of the inspection team and at a critical moment someone grabbed his towel and exposed what we used to call a 'stiff', which, for any other adolescent boy in similar circumstances might have been a social calamity. Not for Jamie. Jamie's rigid penis pointed up like a missile waiting to be launched, and all eyes turned to stare at the wondrous thing. But instead of hiding it, and before any teasing could begin, Jamie took control of the situation. With a broad smirk and a masturbatory gesture, he thrust his pelvis towards us and exclaimed: "Come and get it, girls !" which left everyone roaring with laughter.

Jamie and I shared lots of joyful secrets and knew the smell and feel of each other's cum. He used to giggle before the stuff came squirting all over me, something I have never heard of otherwise. At a French Language camp a few weeks before, he had taken me roughly like a girl, my ankles over his shoulders, moaning "Donna ! Donna !" until the giggles started and he gave me the best he had. Jamie was a very cool kid - straight as they come but completely relaxed about filling me up, which I shall always count as having been my great privilege.

I got another underpants caning on a school camp, about which I will tell more later.

Mr. Cornish once caned his whole class in their speedos. They had to line up, turn around together and stay bent over while a lecture was delivered to their arse ends, then remain bent over until the last boy was caned. Having worked with him at the boarding house I can imagine how this came about.

outside the head's study Being summoned to the headmaster for a caning was a much feared event, though I am sure he caned with less strength than most other masters.

The Deputy Head, for example, was very good at it, and it was he that handled most of the day-to-day discipline problems, including those reported by the prefects, which included socks not being pulled up, caps not being worn outside the school, hair being too long, and the missing of prefects' detentions. I was too busy to go to detentions most of the time and lost track of them anyway - I had so many. I had many painful sessions with the Deputy Head on account of the independent approach that I took to school routines and expectations.

The Headmaster himself, however, would sometimes take over a beating session from his deputy in order to emphasise the seriousness of our misbehaviour.

The first time the Head caned me was for (repeated) late arrival at school.

These days boys at St. C's are probably suspended for that sort of thing, and I imagine that it all becomes a matter for counselling, brow-knitting anxiety and high psychological drama. There was nothing complicated about punishment in my days at school. You just got the cuts and it was over. Masters might spend time talking problems through, but always after the consequences, predictable, unavoidable, and transient, had been suffered.

emerging from the study That first time I got it from the Head, I waited outside his study with a dozen boys of various shapes and sizes, listening to the sounds of the others being beaten as we awaited our turns. He had a thick panelled door and all we could hear was a faint but distinct pop as the each cut was administered. As a boy came out he would grimace to exaggerate the horror of what awaited within. A prefect acted as usher and checked our names off a list as he sent us in. The next boy would disappear into the study, the prefect closed the door, and the sound of caning strokes would resume.

I was only given two strokes the first time I went to the Head's study. We had to bend over on a spot near the fire-place. He said very little except to face the bay window, then he tapped the rug to indicate more exactly where I should stand. His carpet was ancient and threadbare at the site of what must have been countless thrashings.

But the Headmaster didn't have any sport in his style. Another time when he had me in for four, in fifth form, all he said was: "Simons, you've been smoking again. I'll have to give you four. Is there any reason why I shouldn't ?" I couldn't think of a good reason so he simply said: "You know what to do." I went to the caning spot and took my four and then he said: "That'll be all, Simons," and I was dismissed. His caning manner was almost bored and I don't think he had his heart in it. Perhaps he had thrashed so many bent-over backsides over the years that he truly was tired of it.

Mr. Derwent was an eccentric caner. Instead of swinging the cane at a bottom he would hold it about three inches away from the seat of a boy's pants, then withdraw his hand with a flicking motion. His cane rebounded off the arse with a surprisingly loud cracking sound but it didn't look like serious punishment. It was a bit mediocre to watch. I didn't ever cop it from Mr. Derwent, but those who did claimed that his method was effective and painful enough for them not to want more. It was said that he had once drawn blood with a cane and that his restraint was imposed by Departmental regulation. Who knows ?

Sometimes we were sent by a master to borrow a cane from another one, or to fetch a cane from the staff room. This was always an occasion for teasing by the lender, and for tittering by his class.

"How many are you going to get, lad ?" the master might say.

"I don't know, sir" would be the embarrassed reply.

"Well, tell Mr. . . . to make sure he looks after the cane, boy. We need it back here as soon as you've finished. Alright ?"

"Yes sir."

"Be off then."

The boy would exit, carrying the cane and with the sniggers of the class burning in his ears.

Arriving back in one's own class with the cane, one might have to stand about for a while before the master would deign to get on with the thrashing. It was not pleasant to be left standing there and ignored, but holding the cane. For self-conscious adolescents it was always difficult to know just how to hold it, and what sort of pose to strike while holding it. Other members of the class relished the moment to come and hoped with crossed fingers that the culprit would not be excused his hiding.

Returning a borrowed cane to the lender was more difficult than collecting it, with an inspection of trousers being the order of the day. More tittering.

"Was it (the cane) any good, lad ?" "What do you think of it ?" and a whole lot of other unanswerable and embarrassing questions. More tittering. "Hope you've got footy shorts on under there . . . Well ?"

"No sir." More tittering.

Most masters were well supplied with canes and had no need of borrowing, though some canes were a bit tattered, and a frayed end might be held together with rubber bands or sticky tape. If they fell apart in mid-beating, the boy would have to go and get another so that the flogging could be completed. Canes were everywhere. They stood up in corners or on blackboard duster-ledges. They sometimes stood in waste-paper baskets and masters often kept a few to choose from. The selection process, the flexing and flicking, always added to the drama of a caning. Some masters carried their favourite cane from classroom to classroom as they moved from one class and lesson to the next. A cane was standard teacher equipment, like a briefcase, chalk or books.

A typical caning episode might be something like this.

Master says (voice raised in exasperation) "I'll cane the next boy who talks !"

"Simons, I don't believe it ! Get out here and bend over."

Wallop ! Wallop !

Damian hears quiet sniggering from somewhere behind his burning arse.

"Join the party, Dobson. You can get out here too."

Wallop ! Wallop ! as I get two more.

Dobson takes my place.

Wallop ! Wallop ! Wallop ! Wallop !

Simons and Dobson ease their sore bums back into their seats.

waiting their turn

Some boys copped serious beatings. Jamie was a very good looking heart-throb of mine with whom, as I have already said, I had shared some intimacies. But he was constantly tempting fate when it came to canings. He used to keep a tally by inking stripes on the underside of his belt - one per stroke - and by the time we left school it was almost totally blue.

On the first day of middle term in Lower Sixth we had to produce a history essay, which was our homework over the holiday break. I don't know what Jamie wrote (he wouldn't discuss it) but it seriously upset the master, who sent Jamie to show it to the head. When Jamie returned to class his pants had been well striped, his face was flushed and his eyes were still a bit watery.

The teacher demanded to know what the Head had done. Jamie, with stupid bravado, lied. "Nothing sir," he said. It was obvious from the evidence on his trousers that in fact a painful drama had been played out on his arse. Ratty simply bent Jamie over and gave him another four, very slowly and painfully indeed, to complement the Head's effort.

There was no need for another chalking. The dust flew as Ratty laid it on in what was an unusual show of genuine anger and the cane whizzed through the air with tremendous velocity. I can remember few such occasions when a caning was administered in obvious bad temper.

Ratty had a way of telling boys before he caned them that he was going to "apply the rod of instruction to the seat of wisdom". He was too wound up even to bother with this nonsense the day Jamie got what was effectively eight strokes.

Jamie obligingly bared his cheeks for Mick and me later and we were able to examine the eight welts. Jamie's mother had him in a newly marketed fish-net style of underpants (supposed to be thermally efficient) and the stripes on his bum looked like miniature tyre treads.

Ratty had a largish poster on the back wall of his classroom, which depicted, according to the caption, 'Corporal Punishment in Sparta'. It was the drawing of a naked post-pubic boy stretched arse-up by two more naked boys, one holding his arms and the other his ankles, while the tutor sailed into his flailed rump with a birch. I wondered what boys did about their erections during those thrashings in ancient Sparta. Ratty had another poster of naked boys 'Ready for the Athenian Games'. We used to puzzle over the way their foreskins were tied up until Ratty explained that this was to keep all their gear from flopping about dangerously during sport.

Boarders told stories of late night and early morning canings in their pyjamas or underpants or less. This gave them tremendous kudos in the rest of the school, especially as Mr. Cornish was also their senior housemaster. I became a junior housemaster myself after I had left school and did my bit to keep discipline in the house, but Mr. Cornish made my efforts look tame. He used to have whole dorms of boys bent over their bed-ends in their underpants while he did a few rounds with his cane to teach them their manners. That's without mentioning the bare-arse stuff about which I might tell more later.

The closest I came to being caned in pyjamas was my second underpants caning which happened during a school camp. When we were ordered out of bed to be caned for after-lights-out noise some boys in my dorm were in pyjamas, Mick, me and some others were in underpants and one or two in their day shorts. We were all taken outside onto the verandah and bent over in the moonlight to be given two each, except Mick and me (four cuts) who, accurately as it happens, were blamed as the leading cause of the racket. Curtains fluttered in dormitory windows as most of the camp silently enjoyed the show.

Back in the dormitory we compared our marks, and one young exhibitionist chose as a sort of encore to strip off completely and show us how big it could get. He stole the show. After that he was known as 'Bull' as an exaggerated homage to the amazing lump of meat that lived between his legs. Bull had a reputation for exercising it at every opportunity and before the camp was over I found a chance to give him a hand.

I copped it again at the same camp, but in my shorts. There was a riotous but good-natured noise at lunch when the food was slow in coming. A master entered the dining room in the midst of this hubbub and all fell silent - except me and Becker (more about him below). We hadn't seen his arrival. The master couldn't find a cane handy and simply went outside and picked a rather whippy willow branch from which we got a set of welts, bent over the high table, kneeling on a bench with our bums pointed at the diners. Mick said it was a great sight and noted that Becker's arse was turned out well for the occasion, as he was wearing the tiniest of shorts. We copped it in turns - one for me, one for him, and so on.

Simons always deserved it and none of the masters hesitated to redden my rump. If Mick could be thrashed as well, this was a bonus which made them feel that their main duty as guides to the young had been fulfilled. It was unusual to have Becker bending over with me, but it made for a pleasant change to hear his quiet groaning as the whacking knocked the wind out of him. The willow was probably nastier than the real thing but, apart from the stripes wrapping around us in an unusual way, the result was pretty much like that from a cane. It left green sap marks on our pants which I delighted in explaining to the young girl who did our washing at home. She got quite excited and, being in a benevolent mood, I dropped my pants and showed her the matching welts. She was suitably impressed.

Student teachers on placement from the university were a constant feature of school life, something I experienced for myself when I became a tennis coach in my first year of Law and then a junior housemaster to the boarders till I had done my first degree.

Several of the student teachers at St. C's clearly itched to stripe up a few boys. One very pleasantly sexy young man told our class as much. He hadn't had a chance to cane anyone yet and the first boy acting out of line would be doing him a favour. He and another student teacher, he said, had been practising on an armchair, and he thought he would do rather well when he got his chance.

in front of the class Disappointingly, our first class with him went by without event. The next day he admitted that he was still, in caning terms, untried, even though he'd presided over two notorious fourth-form classes. He was, he told us, all the more anxious to have a go.

The lovely Becker gave him his chance. Becker was tall, beautiful and engagingly shy. He had an arse to die for and a face like a Botticelli angel. For some crime he was bent over facing the blackboard and chalked rather grandly while the class called out instructions.

"You want the chalk a bit lower, sir." . . . "Becker's head needs to be down a bit, sir," . . . "Try the other cane sir, Mr. L. has ruined that one" . . . "His cheeks need to be up a bit" . . . and so on. One boy in the front row, worried that Becker's coat tails were in the way, pointed this out and ventured: "Sir, you should make him pull his shirt out too or he won't feel a thing." Sir said nothing but Becker pulled the shirt out, baring his lower back and dragging up the elastic at the top of his underpants. I was in a swoon. As the cane came down each time there was a roar of approval from the class. Becker (bless him !) took it all in good part and even, in a show of bravado, offered to take a couple more strokes.

The next time the student teacher caned a boy in our class there was none of the sport of that Becker beating. He took no nonsense after that first go, and allowed none of the camaraderie of the day when he was, as a caning man, deflowered. We didn't mind too much. We had done our bit.

head down, tail up Mick and I added to his conquests within a few weeks but we had to go out in the corridor for it. He took an enormous run at us after a very deliberate chalking-up. "Head down. Tail up, Simons !" he said. "Get right down, Simons. Touch your toes, boy, I'm going to smarten you up !" He rubbed the chalk on and slapped my buns with the palm of his hand to get the feel of things, then took a walk, then a run, and Whammo ! I discovered that he had the gift !

My last thrashings at St. C's were late in my final term, but there is another story I must relate before I come to that.

In the first days of our last year at school Mick and I were, with the rest of the cricket team, in the gym changing-rooms preparing for an after-school game. From the gym we heard the sound of two boys being decently trounced, then the swinging of the gym door as they left. Mick stepped outside to have a look at the boys who had been caned. When he returned he was followed by two brand new third-formers, little boys with red faces and running eyes, and they were calling Mick 'Sir' !

Mick, ever artful, had conned them somehow about his status in the school and they were obediently following his instructions. Before our disbelieving eyes Mick had them, pants down, arses up, waiting to have their stripes inspected. Although, as they lowered their shorts, they showed signs of becoming dubious about us, they were keen not to make fools of themselves by flouting some mysterious school tradition. Their little bottoms had been reddened and welted in a most satisfactory manner by the inestimable Mr Terry.

About a week went by when, with Mick and four other boys, I skipped a Cadet parade. We had been enjoying a quiet puff in the park next door to the school when some spoil-sport reported us to the Deputy Head, who came to find us and marched us off to the gym to get whacked.

We were all still seventeen except for Rollo, who was eighteen and six feet tall, but dressed in the little cadet shorts that barely fitted even when they were issued two years earlier. Rollo's shorts were very short indeed. His adult buns were almost busting out of his pants and his huge cock filled, not just the crotch, but the whole of his front end. You could clearly see the essential details of Rollo's phallus, his nob, his balls and everything.

We took our shoes off outside and were ushered into the gym where we and the Deputy Head were surprised to find a crowd of third-formers in their gym outfits, chatting merrily in their treble voices and waiting to be briefed by Mr. Cornish for a cross-country run.

Transforming necessity into opportunity, 'Minto' (the D.H.) sat the boys down on the floor in silence to wait while we were beaten !

After a speech to us and to the young spectators about the evils of breaking school rules and the expectations placed on senior boys, we were lined up in front of a gym full of cross-legged children to have our arses flogged. Minto was a mean caner and he relished the moment for, assembled before him, ready for a flogging, were the most troublesome arses in the school. Initially embarrassed, I decided instead that I would show the little chaps how to take a thrashing in style.

Rollo went first and, as he bent over, a hole in his threadbare pants chose that moment to become a wide split across one cheek, revealing his white briefs which were also joyfully ragged and holed, with penny-sized areas of bare bum peeping through. Rollo was something of a challenge for shortish caners, his arse end standing higher than the average, and a bit high to be an ideal target. But Minto made each stroke count. He applied the four very hard and with a longer than usual run-up.

Rollo took it well but when he straightened up he had an impossible-to-miss huge erection throbbing through his shorts. It looked as if his lunch might burst out of a pocket at any minute, or as if the rest of his pants might just explode, spraying buttons all over the gym. The young boy spectators were hypnotised. Even Minto couldn't take his eyes off it. Only Rollo seemed unaware of the sensation he caused. I was surprised by Rollo. I only ever got horny watching other boys being caned. I amused myself with the thought of all those little gym shorts bursting with swollen penises as the third formers got an eye full of Rollo's trousered grandeur. But I didn't have long to pursue this daydream.

I was caned second. Minto savoured the chance to cane me and, before he laid it on, he said: "This is going to be the worst thrashing you've ever had, Simons." As I indicated earlier, everyone thought my arse was fair game. If any master hadn't had a go at it, he counted it as a negligence on his part. I bent over and, as my shiny-trousered arse was being chalked, I caught sight of the spectators, cross-legged on the floor, staring goggle-eyed at my very senior bottom about to take its walloping. Were these the first canings most of them had seen, I wondered ? This would be a day for them to remember, as well as for us.

I had taken the first two strokes before Minto saw the football shorts peeping out the top of my pants. Of course it wasn't deliberate. Both Mick and I tended to wear footy shorts and jock-straps, if we knew we had sport later. Furthermore, we did only have jockstraps under the shorts, so we were not cheating the cane in reality. In any event we'd had no idea that a caning was on the day's agenda when we got dressed for school !

Minto was furious, however, permitting no explanation, ordering the footy shorts off and promising us both an additional two strokes tomorrow. "Anyone else ?" he asked. Mick decided not to chance it and confessed. We were both instructed to change immediately and to see him in his office before school the next day.

ouch Meanwhile, Minto got on with the business end of the other boys.

They took their canings manfully, including 'Legs', a tall lanky boy, the cushiony part of whose bottom must have been difficult for caning masters to locate. His pants were never tight like the rest of ours. Where did his skinny legs become an arse, viewed through a layer of baggy fabric ? It was for the likes of Legs that chalking of the bum was probably invented, so that a master could get the feel of the terrain before applying a stick to it.

To the drumbeat of Minto's pounding cane, Mick and I dropped our pants, took off our footy shorts and put the cadet shorts back on. With our backs to the crowd (who must have been delirious by now) we stripped down to our jock-straps to make the change. My backside with its so-far two stripes, and Mick's milk-white bottom, waiting to be striped, were displayed to maybe a hundred boys, and Mick and I made sure they all got a decent eye-full of the best arses in the school.

And there, right in the front row, I noticed the two little boys who, a week ago, had offered their arses to the breeze for Mick and the rest of us. I caught the eye of one. He looked at me now, not with satisfied spite as one might have anticipated, but with the glow of a worshipper. Timothy still adored me when I thrashed him in his little pyjamas one early morning in the boarding house eighteen months later, thoughtfully making sure that I got a good look at his stripes in the showers afterwards. I had to thrash him a number of times during those years but his devotion never wavered. I wonder if he lies awake at night still with my arse in his fantasies.

When it was my turn to get finished off, Minto's run-up seemed to take ages as he sailed into me with the third and fourth strokes, which were exceedingly painful. Indeed they were hellish, but I managed to maintain the proud-arse position throughout and get in a glance at Timothy just as the cane landed. Mick gave it his best, winking his arse at the crowd when Minto's back was turned.

waiting for the cane Mick and I met the following afternoon, this time in the corridor outside Minto's office, for the two strokes he felt he still owed us. Minto was just as enthusiastic as yesterday and laid them on forcefully and with a fearful run, much longer and faster than in the gym. He dared us never to taste the wrong end of his cane during what remained of this final year at school. We had been let off lightly. But Mick (I could have killed him !) stupidly quipped something that was taken as cheeky, and we both got bent over for two more. The marks from Minto's eight strokes over those two days were more livid than any others I had at school.

Mick was by now sadly growing out of serious pants-down sessions and all I got was a quick look, but he looked perfect. I had loved and lost even before I was fully aware of having loved. But that day I did enjoy the thought that Mick and I had matching sets of stripes - my eight and his six.

waiting with cane and punishment book There were several more caning episodes during my Upper Sixth year when most boys are considered too adult to beat. In any event, it's too late in their school career to bother. All but Simons. Perhaps Mick and I set some sort of record, though it didn't prevent the school from employing me on staff later. The very last caning I received was in the last week of that final year. It was good old Crusty who took me into the corridor and gave it to me in his affectionate but lethal way. "Who's going to do this for you next year ?" asked Crusty as he bent me over, chalked me up and gave me four of the best.

Neither he nor I knew that I would be back three months later putting it about the arse end of Andrew Coggins and those other boys myself ! That is another tale for another day.


Go to Chapter 3 - Damian Simons,
tennis coach and Junior Housemaster


Text and illustrations copyright © 2002

Return to ianboy's story archive listings