Greg & Jeff
Story 1: An Educational Experience
by Jeff Booth <email@example.com>
"I must say I am quite astonished. You are probably the last two I would have expected to find engaging in this sort of behaviour. I will see you in my office in ten minutes."
The Headmaster was quite right. Getting caught smoking dope in a secluded corner of the grounds was not something any of the teachers would have expected to find my best friend Greg and I doing. And to tell you the truth, we were quite astonished too when the Headmaster found us. There was no way he could have seen our little nook from anywhere. And Greg and I had been using the small clearing in the bushes as a private hidey-hole for most of our time at the school. He must have seen us wandering off and followed, then waited a few minutes before completing his investigation.
The complete surprise on our faces when we saw him was equalled only by his own when he took in the scene before him. To virtually all of the teachers, we were seen as star pupils. Not that we were completely angelic, mind you - we were just damn good at not getting caught. And our marks were good too - so long as we applied ourselves in the next few weeks and months, we would have the choice of any University we wanted at the end of the year. Yet here we were, both 17, in our final year at school without ever having been found out, now screwing up big time and getting caught for what was one of the more serious offences around. It wasn't made easier by the fact that, in our dopey state, Greg was obviously on the verge of giggling, and in fact did as soon as the Headmaster had turned his back. Thank goodness we had only been getting started on the dope when he appeared.
"Shit, Greg, get your act together! This is serious! We could be suspended for this, or even expelled." Even through the light mist of dope, Greg could see that. Now was definitely not the time to be taken out of class, just before our trial exams. And if we needed to find a new school to sit our final exams in three months time, that would be disastrous. Even for good students like us, the stress and disruption would no doubt significantly affect our grades.
We walked together grimly across the grounds to the Headmaster's office. I checked my watch. Not quite time, but I knocked anyway. He opened the door a little.
"Ah, Rodgers and Booth. Punctual as ever. Please be seated," he said, gesturing to the row of chairs in the hallway, "and I will be with you shortly." We sat down and waited...and waited...and waited. A full 15 minutes went by.
I glanced at my friend. "Is this good or bad?" I whispered.
Greg just shrugged his shoulders and kept staring at his shoes. Finally, 20 minutes after we had arrived, the door opened once more and we were invited in.
The lecture lasted some time. We stood side by side in front of the Headmaster's desk in the richly oak panelled room. "...Totally illegal...wasted opportunity...utter foolishness...complete lack of self discipline...time when your minds need to be at their peak..." He was pretty much correct, of course. Sure, there's nothing terribly wrong with dope, but he as a Headmaster can't approve of anything illegal. And smoking during school hours during the final preparations for our trial exams - what the heck were we thinking?
"So now I must determine your punishment," he said, and paused. Our eyes, which had been fixed at a point on the edge of his desk until now, looked up. We knew what the first part of the lecture would be; this, however, was unknown territory. And the first signs were not good.
"As you are aware, boys caught using drugs in this school are suspended, almost without exception. Last term, three boys who were caught doing exactly what you were doing received four weeks suspension. There are those who say that fairness dictates that the same should apply to you." I blinked hard and caught my breath. What the heck had we done?
"However, I am not convinced that that is correct." Some hope, perhaps...
"I consider myself a fair man. And for these last few minutes, the issue of how to punish you fairly has been vexing me greatly. First, you two are strangers before me. Were you regular offenders, I might not have been as disposed as I am to look kindly upon you. That does not, however, weigh heavily on my mind. After all, as they say, what is sauce for the gander is sauce for the goose. In the case of a serious offence such as this, lack of previous infractions cannot deter me significantly from imposing an otherwise fitting punishment.
"The other matter that concerns me, however, is deeper. I ask myself - what am I punishing you for? And I answer myself this way. At its root, the reason why you should be dissuaded from smoking marijuana is its potential to adversely affect your mind. At this time of your life, more than ever, you should be at the peak of your alertness. Whatever would possess two intelligent boys like yourselves, who should be maximising your potential, to instead dull it with the use of depressant narcotics completely eludes me. So, since you seem unable to make that leap of logic yourselves, a punishment is required to impress the folly of your conduct into you. And I would hope that as a result, you would be dissuaded from any more of this self-destructive conduct which cannot but adversely affect your academic performance.
"As I said, suspension is the normal penalty for this offence, almost without exception. If yours was an offence that had harmed others, such as cheating, I would have no hesitation in suspending you. Exception must be made, however, where the evil wrought by the penalty would outweigh the good that it would seek to achieve. And I fear that is what would result were I to suspend you. I am seeking to prevent you from hurting yourselves, not others. The disruption to your studies would, I believe, be just as destructive to your final results as the continued use of marijuana. No, that would be an unjust punishment."
Well, we were in the clear on that count. Greg and I breathed barely audible sighs of relief, almost simultaneously.
"My normal alternative to suspension for seniors such as yourselves would be to order you to give up a substantial amount of your free time contributing to the school - weeding the grounds, assisting with repairs, cleaning the guttering and so forth. Normally, a very productive punishment. But again, I cannot see this as appropriate in this case. Again, this would be time you should be spending on your studies. Were I to jeopardise your futures with such a requirement, I would prove myself as foolish as you have been. No, your punishment must be swift and rapid, and allow you to return to your studies as soon as possible, free from additional burdens, whilst still serving as a salutory lesson to you.
"So I find myself turning to a punishment which I do not particularly favour, but which I consider is the only option available to me that fits these criteria. You will report to me in the gymnasium after school today, where I propose to cane both of you. I trust that you will find the experience - in its entirety - somewhat educational."
Neither Greg nor I knew what to do. We were both stunned. After a few seconds silence, we were reminded where we were when the Headmaster said: "That will be all, for now." We took the cue, turned on our heels and left.
We didn't quite know what to say to each other as we walked across to the rest of the boys enjoying the end of their lunch hour.
"Well, at least we're not suspended." I said.
"Yeah, but..." said Greg apprehensively.
I knew what he meant. Ours was a private boys school, and unlike most in Australia caning had not yet been abolished. Even so, it was not regularly used. And then, only on the junior boys - it was virtually unheard of for anyone in their senior years to be caned. In one's junior years, there was a certain cache that came with being caned. It marked one as an outlaw, a man of boldness and daring. After gym or sports, a 14 year old who doffed his underpants to reveal the unmistakable red brands of the cane on his buttocks would saunter to the showers drawing looks of admiration. An older boy, however, would draw chuckles and pointing fingers. What would it be like for two 17-year-olds like Greg and I?
And this was quite apart from the caning itself. When, at 14, I had looked admiringly at the candy-striped outlaws, I had on occasion wished mischeviously to be caned, to know what it felt like. But I never had the resolve to make sure I got caught in flagrante delicto and expose myself to reality. Even more recently, corporal punishment in the form of spanking and caning had featured in my sexual fantasies, and I had enjoyed several climaxes imagining my bottom being punished as I stroked myself. But now that the reality was so suddenly close, I was filled with nothing but apprehension.
During the afternoon's lessons, my mind was anywhere but my work, and I could tell Greg was similarly preoccupied. Occasionally, one of us would catch the other's eye, and grimace slightly. We were fortunate about two things. First, the school did not approve of public caning. Only we and the headmaster would be present. Secondly, caning was not on the bare buttocks, although the victims did have to receive their sentence on their underwear. I shuddered to think what the afternoon would bring.
A sign on the Gymnasium door read "Closed". That was all. That was all that was necessary to let the rest of the school know that it was not available for casual use that afternoon. They didn't need to know the reason, although it would soon be common knowledge.
Greg and I walked there together silently. Ever since the beginning of high school, we had been a team. For some reason, we had both clicked. Neither of us was particularly sporty, both a little smaller and thinner than normal, both good students, and both comfortable with each other. We were comfortable enough that we knew when we needed to talk, and when silence between us was best. Now was a time for silence. We had shared many milestones together, so it seemed strangely fitting that we were to share what was about to transpire.
Our steps slowed as we approached the gymnasium, passing a trio of boys turning away disappointed from the closed door. "It's closed" they said to us. Yeah, we knew. We paused at the door and waited until no-one was in sight before entering.
The gymnasium was a pretty large room, the size of a full-sized basketball court, and two storeys high. At one end were the squash courts, at the other, the change rooms. Lots of equipment was arrayed about its walls, able to be swung out into the body of the hall for use and tucked aside when not needed.
The Headmaster was already there, sitting on a chair on the side of the large room. He was seemingly in a reverie, gazing towards the vaulted ceiling, but his eyes turned to us as we entered. We noticed him, but our attention was immediately drawn to the two canes resting by the side of his chair. "Why two? One plus a spare", I thought.
"Ah, gentlemen. I was hoping you would not detain me too long. Kindly retire to the change rooms, remove your uniforms and report to me out here in your underwear."
Although we had known what was coming, the command was still like a bucket of icy water hitting us with full force on this warm summer afternoon. Dazed, we turned and entered the change room, dropped our bags on the benches and began removing our ties. The dead still of the change room was a great contrast to how we normally saw it, full of lively teenagers joking with one another as we readied for sport. That cheerful laughter was replaced by the slightest of sounds - the slip of a button, the pull of Greg's arm from his shirtsleeve, the plop of a shoe, the clink of my beltbuckle as I unclasped it.
Finally, as I shed my trousers and hung them on a hook, I turned to look at Greg. He was just straightening up after tucking his shoes neatly under the bench. We both stood there for a moment. His eyes flickered over my body, and mine over his. He was wearing pale blue boxer shorts with dark blue vertical stripes, maybe slightly too small for him. I was wearing plain light blue briefs, definitely slightly too small for me. Heck, isn't everyone at that age wearing clothes slightly too small, your mothers wanting to get every last bit of wear out of them before shelling out for new, better fitting clothing?
For a moment, time stood still. Greg and I had gotten changed near one another many times, both at school and outside. We showered in the communal showers here regularly after gym. But never in circumstances quite like this. We were both about 5'6" tall, and around 50kg. We were both very slim, with the gangliness of youth still present. Greg was slightly taller than me, but a little more thin and wiry, whereas my muscles were a little more toned and developed. I may have had the slightly more defined body, but Greg had by far the more attractive face, with twinkling yet soulful blue eyes setting off a mouth normally tweaked upwards in a charming yet mischevious smile. His nipples were small and pointy, but surrounded by a broad pink areola, in contrast to mine which were tight and compact. Even at this age we both had some facial hair, requiring us to shave several times a week; and the fact that our chests were destined to become hairy was attested to by the thin lines of hair running from our navels beneath the waistbands of our underwear, and the small black spirals beginning to poke out from around our nipples.
At this most desperate time, a strange thought sprung into my head of one of my fantasies. Greg and I, in bed together, naked, arms around each other, legs entwined, hands caressing each other's back slowly, feeling each other's slow breath on our cheeks, his mouth opens and our eyes meet, I begin to say "I..." before his lips meet mine and we kiss, slowly, delicately...
Where was I? I blink and look at Greg, now looking anxious and vulnerable. Although it seems like an age, it must be only about two seconds since our gaze met. I raise an eyebrow slightly and tilt my head - You okay?. He gives a slight nod, curls his lower lip up ever so little and bites down on it - Yep, but shit-scared. His eyes dart over to the door. Shall we get it over with? I wrinkle the corner of my mouth slightly - I'd rather not, but I guess there's nothing else for it - and start for the door with Greg falling in behind me.
"Welcome back gentlemen." That was one thing about the Headmaster. He always treated us like adults. Even when we were thirteen. Even when we were standing before him in our underwear. Even when he was about to bend us over and thrash our bottoms. "We need to make the necessary arrangements. Please set up that apparatus over there, would you?" He pointed to a frame. One vertical side of it was hinged to the wall, the other vertical strut was on a small castor. Between the struts were two long horizontal wooden beams. The top beam was usually used for chinups, the bottom as a balance beam or for elevated pushups. Or, as we were about to discover, for canings.
Greg and I swung the frame out from the wall and each took one of the wires used to tether it to small plugs in the floor. As he squatted to secure his wire, I noticed that his scrotum was visible just inside the leg of his boxers. Shit, this is so humiliating! I thought. Why couldn't we have set this up while we were dressed? But I realised I had answered my own question. In his office the Headmaster had referred to "the entire experience". The caning was the least part of the punishment. The greater part was the humiliation. We had behaved foolishly and were now being made to feel foolish. And this was just the beginning. The crowning humiliation would come in two days time when Greg and I were forced to expose our stripes of shame to our peers in the showers after gym. Oh fuck.
"Now, we will check the height." With me standing beside the frame, the Headmaster asked that it be lowered two notches, so that the top was slightly lower than our crotches. "Thank you. Now, please stand beside each other, there, and there", indicating a marked line on the floor to the side of the frame and back somewhat from it. We did so, hands self-consciously moving in front of our crotches. "And get those hands behind your necks!" he barked suddenly, causing us to snap into position with fingers clasped firmly behind our heads.
He began the necessary lecture again, slowly pacing circles around us. Of course, in one way it was completely unnecessary. He had told us everything just a few hours before. But it was completely necessary as part of our punishment. To prolong the wait, the humiliation. He did not humiliate us verbally. That would have been destructive. No, we humiliated ourselves, as our minds were preoccupied with the image of how we must look, two adolescents standing like children before the Headmaster, the man we admired, the man we regarded as a friend and an equal, the man we so often would chat with in the playground and have happy discussions with, now showing his contempt for our behaviour as we stood stripped before him, subjecting ourselves to his scornful gaze, his scolding words, his punishing cane.
My mind strayed back to the image of Greg before me in the change room, then to Greg crouching on the floor with his scrotum visible. I shot a glance over at him and was surprised to see the front of his boxers tenting out slightly. My surprise at this development was only matched when I suddenly realised that I too was becoming aroused. Neither of us had full erections but a glimpse down showed that my penis was very clearly defined in the tight material of my briefs, and as for Greg - well, his arousal was pretty obvious. I shut my eyes and tried to concentrate on the lecture, but all I could think was - Thank goodness it's not me in the boxers. I was managing to stabilise but only just.
I opened my eyes again as the Headmaster arrived in front of us once more and stopped. The lecture was coming to an end.
"And so, since you two have elected to comport yourself in such a juvenile manner, you have forced me to punish you as juveniles. Believe me, it gives me no pleasure at all to see you like this." Strange choice of words, I thought. "I would have thought that gentlemen that I had regarded as responsible and intelligent could be trusted to steer themselves in the proper course. Obviously, my faith was misplaced. I can only hope that the correction I will apply to your course this afternoon can convince you that the fruits of juvenile irresponsibility are not nearly as pleasant as you may have surmised.
"Now, Rodgers, kindly step up here please," he said, indicating the frame, and turning to retrieve the cane. I honestly didn't know whether I was relieved or annoyed that Greg was going first. I just wanted the whole thing to be over.
Greg walked the few paces to the frame. The Headmaster was just collecting the cane. While his back was turned, Greg took the opportunity to slip his hand down and depress his semi-erect penis slightly, and stood right against the beam to prevent it from popping up again. Smart move, I thought. He didn't look around to me but I'm sure he would have felt my eyes on him as he did so.
"Bend over the frame, boy, and touch the floor," said the Headmaster, in a colder tone than I had heard from him for some time. He had also never called us "boys" for several years. Maybe it was part of the humiliation, or maybe he was trying to come to terms himself with what he was about to do to `gentlemen' with whom he would normally be conversing intelligently.
Greg bent over the bar double and planted his fingertips on the floor. The position did not look comfortable. I wondered idly how those less flexible than us would manage the position. "Spread your legs apart. Further, further.." came the order, accompanied by a tapping of the cane on Greg's inside thighs as he wriggled his legs wider apart. >From my position behind and to the right of him, I could well see my friend in his sorry position, and my heart went out to him. His calf and thigh muscles were pulled taut; his hair hang loosely from his head; his boxers riding high up his thighs and streched tightly over his buttocks, spread to present a firm and neat target. Again, a slight glimpse of his scrotum was visible inside the right leg of his boxers. Greg had only recently started wearing boxer shorts; he might not realise exactly how much of his genitals could be seen but even the problem with his erection alone would have been enough for him to be bitterly regretting wearing them on this day, I was sure.
As the Headmaster stood beside Greg and held the cane up to his upturned buttocks to gauge his swing, I became aware once more of my own erection, more insistent than ever. Bizarre as it may seem at a time like this, to see played out in front of me a scene very close to those I had fantasised about was erotic enough, but for the starring role to be played by my best friend, the subject of many a carnal thought himself, was undeniably arousing. While I thought I should close my eyes, the sight was compelling.
The Headmaster took a couple of steps back and raised his arm. My eyes were locked on Greg. His bare chest rose and fell quickly as his breathing quickened, his nipples erect, his areolae stretched broadly with his arms braced. Oh shit, I suddenly realised, he can see the Head. Between his splayed legs, Greg would have an excellent view of his nemesis as he brought the cane down. The Head started to move and my eyes sprang to Greg's. As if magnetically, his were drawn to mine. We locked, and for a moment I felt his anxiety, he felt my alarm, and I willed him Oh Greg, close your eyes man, don't look. As the Head took his final step and the cane began arcing down, Greg's eyes snapped shut, his jaw clenched, his face tautened in an anticipatory wince as...
Swish! The cane raced towards its target.
Crack! It scored a direct hit on its fleshy target. I winced.
Bang! Greg's body was jolted forward against the frame by the force of the impact, which in turn was shoved back to be caught by the guy wires. The sounds ricocheted around the brick walls of the gym, almost drowning out the
Gasp! as Greg drew breath in sharply through his clenched teeth. He let it out slowly then panted a couple of times, opening his eyes once more and looking nowhere in particular as his mind coped with the pain.
The Head waited for Greg to regain some composure before retreating for his second stroke. Greg did not need to look at me this time, he prepared himself once more.
Swish! Crack! Bang! Gasp!
Swish! Crack! Bang! Gasp!
The second and third strokes were delivered much as the first had been, at intervals of about 20 seconds. The Head walked back to his position and paused. He was panting slightly as well. Seconds passed. Greg's eyes were closed once more, waiting. It did not come. He opened them. Still the Head stood. 40 seconds, 50 seconds. Then he raised his arm high. Greg's eyes closed again and he prepared himself as the Head strode in for his fourth shot.
Swish! CRACK! "Huhhh" BANG! "Hhhh-ahhhh!"
The "Huhhh" came from the Head. The stroke had been powerful and he had brought his arm down with all the power he could muster as if beating a sledgehammer on a "ring the bell' contest at a country fair, at the same time letting out the aggressive grunt of a tennis player delivering an ace serve. The cane had slammed extraordinarily hard into Greg's buttocks and as he jolted forward his head snapped up, his eyes and jaw sprang open and he was unable to restrain his cry of pain and astonishment.
There was dead silence for a moment and the room was frozen into silence. Greg was fixed mid-gasp, eyes dead ahead, arms pressing his body upward. Then, a small moan, followed by another, then a sigh as he lowered himself once more.
The Head stood still, eyes closed, taking deep breaths. I was astounded. I could not imagine that he would ever cane a junior boy that hard. Had I not known him better, I would have seen that last stroke as one of sheer sadism. But that was not the man I knew. Had he allowed himself to be carried away by evil intent? I was sure there was some other explanation. I will never know, but I am sure that fourth stroke was in some ways a symptom of the Head's own frustration and rage at our stupidity, and the thankless task of humiliating and flogging a kind, caring, sensitive, intelligent young man like Greg, who was more a friend than a mere pupil.
Greg's eyes moved to mine. They were wet with tears. He gulped slightly, suppressing a sob. His eyes were no longer anxious, nor determined. They were tired, begging, supplicating. And I could not help him. My look was one of anguish.
The Head broke from his reverie and wandered back into position. This time, Greg did not bother to close his eyes.
Swish! Crack! Bang! "Unnnnh!"
A much lighter stroke, it seemed, this time, although without his jaw clenched a low groan escaped Greg's lips. He was now not so much poised as hanging over the bar. The Head turned and walked back. I begged that this would be the last stroke. I had not known anyone to receive more than six before (most junior boys would receive two, three or four, with six only for the most serious offenders) but there was always the possibility that our seniority might be thought to merit additional punishment.
Swish! Crack! Bang! "Unnnnh!"
This stroke landed not on the main mound of Greg's buttocks, protected by his underpants, but instead on the bare flesh at the very top of his thighs, just below his cheeks where his boxers ended. This was expected, and also a relief. It was the Head's practice, we knew, to deliver the final stroke on the bare thighs so that even in his underwear or at swim practice in his speedos a boy was marked to the world as having been caned. For this reason, it was known among the boys as the `speedo stripe'. Hmm. Greg and I had planned going to the beach at the weekend. As keen speedo wearers, this suddenly seemed like not such a good idea. However, we both now knew that Greg's ordeal was over.
"That will do. Stand up, Rodgers."
There were a few seconds pause as Greg drew a few breaths, then drew his legs together and awkwardly raised himself. The entire caning had taken less than five minutes but it must have seemed like an age to him. He was visibly wincing as the skin on his buttocks relaxed and shifted. The welts were already beginning to appear on his thighs from the last stroke. He straightened, and instinctively moved a hand behind him to massage his bottom.
"Hands behind your neck!" barked the Head, and Greg reluctantly complied. "Go and resume your place." Greg turned, and I saw my friend, near naked, tousle-haired, red-eyed, with tears still drying on his cheeks. There was perspiration on his forehead and across his chest. Understandably, his erection was gone. I had forgotten mine, but, as my mind drifted down, I was surprised to feel that I was still slightly swollen.
Greg slowly and gingerly walked back towards me. I longed to reach out to him, to hold him, to stroke his back, to cradle his head in my arms as he sobbed out the pain. Instead, I could only try to offer the sympathy of my eyes as he stood beside me once more. But even that was probably dulled by the mounting alarm that my ordeal was about to begin.
"Booth, you know what to do."
I walked over to the frame and stood behind the beam. I took my hands down, only just then realising what a weight they had been to hold up for what must have been twenty minutes or more, including the lecture. I took a deep breath.
"Come on boy, we haven't got all day." I bent over the beam. I had been right, the position was definitely not comfortable. Things were not helped by my semi-erect penis, its firmness pressed awkwardly against the wood. As much as I wanted it to, it would not subside. At least my briefs had kept it pointed down - with the Headmaster's gaze upon me I did not have the opportunity to adjust myself that Greg did. Had it been upright it would have been squashed under my stomach on the corner of the beam, which would not had been pleasant.
"For heaven's sake, spread your legs boy!" Shit, of course. Now the Head was definitely irritated. Concentrate, concentrate. I shuffled them apart. I was relieved to find this a slightly steadier position, although incredibly humiliating and exposed. My buttocks were stretched tight. Since my briefs were behind the beam, all parts of my body that I could see were naked. With my legs spread, the pouch in my briefs containing my testicles would be clearly visible to the others. Framed between my legs, my upside-down view showed the Head visually inspecting me. He raised the cane and I felt it lightly tap against my buttocks as he measured his swing.
The Head began pacing back, and my eyes snapped to Greg's, which were fixed on me. I saw through his pain what I had been trying to offer him a moment ago - sympathy, compassion, strength. Then the first heavy footfall, and I shut my eyes and braced.
"Swish!" As I heard it coming, instinctively, every muscle tensed. No, No, I wanted to say, keep loose, keep limp, flow like water...
"Crack!" At first, I didn't really feel it. There was the sound, and a sudden dull momentum fell against my buttocks and slammed me into the beam with a Bang! As my hips were shunted forward I felt a sudden strange twinge in my crotch as my penis was driven hard against the wood, in turn pressing my testicles back to brush the insides of my thighs. As the beam seemed to press back against me I felt the air rush from my mouth in the kind of strange, involuntary gasp that Greg had made. Then simultaneously the pain arced across the higher part of my cheeks, an initial penetrating stab that was suddenly gone and replaced by a consistent heavy throb.
I wriggled slightly to adjust my position on the beam, then the second stroke.
Swish! Crack! Bang! Gasp!
Again I was slammed forward; again, my penis squeezed tight against the beam as the air was driven from me and a new fire was ignited, this time lower down towards the base of my buttocks. They were now framed by two pulsing streaks that concentrated my mind and seemed to be trying to take over my heartbeat. The sweat had broken out on my brow.
As I stretched slightly, in a vain attempt to try to distract my mind from the pain my mind turned to my penis. I had never imagined that the caning would provide this sort of physical stimulus to it. I do, under normal circumstances, enjoy pressure on my penis, and have several times brought myself to orgasm purely by humping something like my doona or the side of the bathtub at home without actually touching my genitals. The caning was literally forcing me to hump the beam with every stroke, which no doubt accounted for the fact that despite the pain I was still semi-aroused.
Swish! Crack! Bang! Gasp!
I had let my mind wander and hadn't been ready for that one. My arms almost slipped, but I caught myself in time. The third stroke landed just below the first. The pain was insidious and insistent. I could feel the sweat starting on my chest.
My eyes were still closed and I was in a realm of darkness. I opened them to see the Head mopping his own perspiration from his brow and palms. I looked across at Greg, who had deep concern written across his reddened eyes. Halfway there. I'm all right, buddy, I tried to say back, but I didn't really feel all right. Particularly when I suddenly remembered that this was the fourth stroke - the real killer stroke for Greg. Oh shit. What will he do?
The Head was once more taking his time before delivering the stroke. I closed my eyes and feared the worst. At least I know what is coming, I thought. At least I know I'm halfway. How much worse can it be anyway?
Swish! CRACK! "Huhhh" BANG!
There was no doubt, it was a powerful stroke. It caught me slightly below the centre of the buttocks like a concrete weight swinging down. The beam met me coming the other way. My hips buckled and my penis was rammed against the hard wood as if I was trying to piledrive a hole to the other side. It gave a slight dull throb. But I barely noticed any of that as the thin cane seemed to have sliced me open with a scalpel. "Ohhh-hhh", I grunted; and like Greg before me my head shot forward and I stared wide-eyed at the floor in front of me trying to comprehend what had happened.
As I silently took stock, however, gulping occasionally as the scalpel slice dulled and the burning, pulsing heat began, I realised that I had been spared. Objectively speaking (and it is damn hard to be objective in this situation, let me tell you...) Greg had gotten it far worse, I was sure. The Head had caned hard, but his grunt was only a small version of when he had delivered his coup de grace to Greg. This seemed to confirm my suspicion - that stroke had been a one in a million, an unwanted and regretted lapse by a fair but flawed man who had become overcome by the situation. He needed my fourth stroke to be firm, but not absurdly so. Poor Greg.
I dropped my head and looked across at him. He was misty through the tears. I could not see his eyes properly. I was sure he was remembering his severe stroke and willing me to pull through. I did not know if he realised my blow had been much lighter. I guessed that he had not seen my eyes when he was bent there after taking his blow, even though he was searching for them and for their comforting thoughts. Poor Greg.
Seconds ticked by. A bead of sweat ran along my chest over my right nipple. I suddenly realised I had sunk down awkwardly and, with effort, raised myself again into the braced position. Unlike Greg, I shut my eyes again. As I awaited the next blow, I somehow felt through the pain that my erection had gone.
Swish! Crack! Bang! "Fffffh!"
This stroke cut diagonally across the four already planted. Lighter, of course. Still enough in my weakened state to force a slight sound from my lips but not nearly matching the freight-train force of what I had just endured. A constellation of new sensations lit up at each intersection point. I choked down a slight sob. It was nearly over.
Swish! Crack! Bang. "Arrr-hhh!"
A semi-moan, followed by a sharp intake of breath. This was, of course, the stroke below my underpants on the upper thighs. The speedo stripe. Though the force was the same, the sting on my bare flesh was acute. I could only silently thank my stars that the rest of the caning had not been bare.
"You may stand up, Booth, and return to your place."
As I slowly straightened, I tingled all over as circulation was restored to my strained limbs. A new burst of pain shot through my buttocks, firing along the lines of my stripes. I longed to reach back and massage them but knew better, clasping my hands back behind my neck as I turned towards Greg and walked back. The tears had cleared and I could see his face had already regained some of that old confidence as he flashed me a slight grin. Thanks man, I flashed back, Glad to see you back.
The Head stood in front of us, cane clasped in his hand behind his back. "Turn towards each other." We did so. We were standing about a metre and a half apart, face to face, still with our hands clasped tightly.
"What you see is many things. You see a boy who thought he was a man. A boy who thought he could flout the rules. A boy who thought he knew better than those who have his best interests at heart. A boy who was caught, and who must realise the error of his ways. A boy who has been caned severely in a manner befitting someone several years his junior - indeed, whose stupidity has earned him one of the most severe canings it has ever been my unpleasant duty to perform. Not least because it should have been totally unnecessary.
"Because you also see before you a man. A man of intelligence and common sense. A man with a great future. A future that, he should know, is not worth destroying for the sake of instant gratification. You see one another, and you see yourselves. And I hope that, between the two of you, you can work out where your future lies."
As the Head spoke, our eyes were locked together in silence. Our hair was tousled from our upside-down pose. Our faces were tear-stained and sweaty. Our adams apples occasionally jerked as we swallowed. Our chests rose and fell, beads of sweat glistening on our pectorals, nipples firm and erect. Occasionally, one of us would glance down and run our eyes over the other's body. The caning had certainly dented our spirit, but I could see in Greg the same sense of relief that I was feeling. Pain and humiliation are transitory. The caning was over. The score had been settled. We could wipe the slate clean and start again.
"This session is now at an end. I bid you good day." The Head turned and walked towards the door. Immediately, our hands dropped and went to our backsides.
The Head turned. "Oh, and by the way - please put that frame away before you leave, won't you?"
Actually, the session wasn't at an end. But before I get to that bit, perhaps I should tell you a bit more about Greg and I.
Being at a boy's school meant we didn't have a lot of interaction with girls. It wasn't a boarding school and everyone went home each day but really your social partners were our classmates. We had a few other friends at the school, and occasionally went out in a group, but we were fundamentally pretty shy guys and more than anything else preferred each other's company. Most weekends we would get up to something together. We just felt so comfortable and safe together.
A lot of guys our age spend a lot of time appeasing their rising hormones by looking at porn and talking ribaldly about sex. That really wasn't our style. Hey, sure, we were guys, we had sex drives, we jerked off (alone, never together), but we didn't sit around talking about it all the time. Girls were there, some of them looked good, but they weren't a big part of our life, and could wait until later. Right now we had each other, and that seemed to be all that mattered.
It was shortly after I turned 16 that I realised I had a crush on Greg. One weekend we had been at the beach together, and that night I had a dream. I dreamt we were up at Greg's parents beach house and had come in from swimming. We were in the room we usually shared together, getting changed. We often got changed together, we weren't shy around each other like that. I had just slipped my speedos off when Greg said "Hey Jeff, I can't get this knot undone, can you give me a hand?" I wandered over naked and started fiddling with the knot in his drawstring, with my hands brushing his covered penis every now and then. I finally got it undone and for some reason I slid his speedos off for him, running my hands down his legs. When his penis popped out it was hard, and mine was too. He took my hand and said "Come on, let's shower", and we walked into the bathroom, climbed into the shower together and began to soap each other up. It was just as Greg was running his soapy hands under my thighs and beginning to massage my scrotum that I woke up to find the last of a large load of semen drizzling from my penis.
I was a bit bewildered by that dream but there was no denying that I found it immensely erotic. After that I began working in the occasional fantasy about Greg into my masturbation sessions and found that I came much harder and easier than thinking about some imaginary girl or poster pin up. I also started thinking about how good I felt when he was with me, how relaxed, how we could communicate so much in a glance. He was not just my best friend, I was falling in love with him. I didn't think of it as being gay - girls do turn me on too. But the one I really felt for was him.
Nothing ever happened between us. He was so special to me that I did not dare to damage our friendship by doing anything that could possibly make him feel uncomfortable and want to distance himself from me. I had no way of knowing if he reciprocated my feelings. So we kept doing things together. Most of the time, I could put my sexual thoughts about him to one side, for they were only one element of the attraction. Most of all, I loved the warm and joyful feelings he brought me, and I could have them whenever I wanted. I did sometimes roll over in bed and imagine him lying there next to me, that cute face, that bright smile, those soulful eyes, keeping me safe. I felt pangs of guilt when I masturbated to thoughts of Greg; that it was somehow wrong to use my friend in this way. But I locked that guilt away.
The closest my feelings would ever come to rising to the surface was usually when we were swimming together at the beach. If I say so myself, we both looked cute in our matching black school speedos, which we wore to the beach too. Neither of us liked the feel of board shorts, which in the water were heavy, awkward and chafing; and we didn't mind the revealing nature of speedos. We would sometimes lie sunbaking and talking to each other, eyes hidden behind our cool sunglasses, which allowed me to run my eyes along his body every now and then, admiring his biceps, the slope of his back, the curve of his tightly wrapped buttocks. Like any teenager, both of us were quite prone to erections, and there wouldn't have been a beach day that both of us did not get that swelling feeling at some time. This was not too much of a problem; we both wore speedos tight enough to keep our penises firmly in position nestled on our testicles, semi-hard, rather than sticking straight out fully erect in front of us, so our arousal was not that blatant. However, it would have been obvious to anyone who took more than a passing look, since our swollen shafts and circumcised heads became very prominent. It didn't really phase us though. Sometimes when sunbaking we would deliberately roll onto our backs and wriggle our hips up a bit so that we could feel the sun properly warming our stirring genitals. I don't know what triggered Greg's erections but many of mine were caused by his presence. Particularly if we had a fun wrestle in the shallows, which would happen when both of us felt a little frisky. He was often hard too after these encounters.
This play never left the beach, though. We had never been erect when changing with each other. From time to time, when looking into his eyes, I wished I could dive right in to them and swim around inside his head looking for his sexy thoughts, and whether he might just want what I wanted. I also wondered if he could read my desires in my eyes. But I decided, probably not. So while on my part at least our relationship contained a degree of sexual tension, it remained unresolved.
At least, until now.
The Head turning back to remind us about the frame as we started rubbing our bums was embarrassing - though no more embarrassing than the many other things that had happened over the last 30 minutes. But then he was gone.
"Oh, mannn!" groaned Greg.
"Hey, at least it's over. We're still in school, we've had our punishment, that's it."
"But - Christ! That was incredible! It hurt so much I thought I was going to pass out there for a minute."
"Yeah, I agree. I think you got it worse than me. You didn't know how many you had coming, and that fourth stroke you took was much harder than mine. I don't know what got into him."
"Yours looked pretty bad too."
"I'm sure yours was far harder. Plus you had to stand around for ages at the end without doing this," I said, referring to our tender, tentative squeezes of our buttocks.
"Well this certainly makes it feel a bit better," he agreed, as we started slowly walking back to the changerooms. Since the gym was closed, we had the place to ourselves.
"Oh shit, look at us!" I said as we walked in and caught the first glances of ourselves in the mirror. We had seen each other and had some idea of what wrecks we would look but seeing ourselves for the first time was still a shock. I looked like I'd just had a wild night on the town until 3am. We looked at our reflections for a moment.
"I guess there's something else we have to look at too" I said, and looked at him.
"Yeah, well, you've got a real neat speedo stripe there" he said, pointing. I tried to get a look in the mirror but it was basically a face mirror, fairly high up. Turning around I could catch glimpses of it but couldn't get the full effect. "Try standing on that bench there" Greg suggested. We pulled the bench over running parallel to the mirror and I stood on it. Looking over my shoulder, I had a good view of my midsection - from the small of my back down to just above the knees. In the middle, my curving buttocks economically covered in blue cotton. And just below, neatly running horizontally across my thighs, was a bright red speedo stripe. That would be there for a while.
Greg hopped up beside me. While standing straight, the legs of his boxers hung down a bit and partly obscured his speedo stripe, but he hitched them up a little so that it could be viewed properly. The bench was a little unsteady and he placed his hand on my shoulder for balance. We stood there for a moment until Greg said "Better check out the rest of the damage". He moved his hands to his hips, carefully moved his waistband back from his buttocks and slid his boxers to his knees.
"Wow", I said. Most of Greg's skin was a pale tan, but his buttocks were a milky white, as they had been protected from the sun by his speedos. The white untanned triangle was the perfect canvas for the Headmaster's work of art. Four parallel strokes, fairly evenly spaced, marched over his mounds, bisected by a confident diagonal and underscored by the speedo stripe for emphasis. The fourth stroke was very evident, looking broad and very ugly. I idly wondered if it would ever heal properly. Straightening up, Greg looked back and bit his lower lip as he wobbled slightly and moved his hand to my shoulder for balance again. It was an impressive sight.
He glanced across at me and I moved my hands down to my briefs. Pulling the waistband back, there was a very slight tug against my skin where the cotton had stuck slightly to my stripes. Soon my underpants were on their way down my thighs to join Greg's at knee level, exposing my penis and testicles which nodded gently between my legs. As I straighted again I caught my first glimpse that day of Greg's genitals. Our scrotums were both loose in the heat, with testicles dangling lazily. His penis sprouted from a fairly thick bush of pubic hair to hang, trunk-like, in front of him. I filed the image away and turned to survey my stripes. My fairer skin meant my tan lines were not as distinct as his, but my buttocks were similarly pale white with the angry lines neatly laid across them. We matched nicely. As if to underscore the symmetry, I placed my hand on Greg's shoulder in a matching gesture.
"Sort of like picket fences", he said.
"Or like he's been keeping tally on our bums," I said, adding "You definitely got it harder" when I noticed that my fourth stroke, although still the centrepiece, was markedly less angry than Greg's.
Greg giggled a bit. "I can't believe this is us." I knew what he meant. It was somewhat surreal seeing these pairs of punished buttocks displayed in the mirror knowing they were our own. The pain told us it was real though. Greg reached round with his free hand and started delicately touching his stripes, then a little more firmly. "Feels funny."
I reached around to start touching my own. The throbbing would change a little where I pressed. We both started gently massaging our cheeks again, enjoying the odd feeling of relief. There was a dull heat radiating from our bottoms. "What a pair, eh?" he said, winking at me.
Greg turned his head back and moved to step down from the bench. Unfortunately he forgot about his boxers round his knees. He tripped and our mutual balance turned into mutual chaos as the hand on my shoulder suddenly pulled me forward. Similarly hobbled, I could but push my arms forward to break the fall. It could have been nasty, falling onto the tiled floor, but we caught ourselves in time. "You klutz!" I laughed as we lay on the floor, naked, legs tangled together.
We pulled ourselves apart. Greg kicked off his boxers and stood up with them in his left hand. He looked back down at me. His penis seemed to have enlarged very slightly. "I sure could use a shower," he said. He turned and threw his boxers onto his schoolbag.
"Me too" I said, slipping off my underpants as his striped bottom headed for the showers, his hands idly reaching around to lightly squeeze it once more. I followed him in, with a strange feeling coming over me. Sort of like something that had happened before...
The showerheads were in a long row. We selected ones side by side in the middle, turned the water on and let it run over our warm sweaty bodies. There were a couple of old bits of soap on the rack in front of Greg; he picked them up and handed one to me. We began to lather up.
I don't know what made me do it. Just one of those impulses. Those spur of the moment things. But as I rubbed the soap across my chest I suddenly asked "Hey Greg, could you do my back please?"
He looked back at me; for a moment, he had a quizzical look in his eye. He looked like he was weighing things up. It was a "What the...?" sort of look. Uh oh. Had I screwed up? But the look soon changed to a friendly one. "Yeah sure. If you'll do mine too."
My heart jumped a bit. "You're on."
He stepped toward me and I turned around. He placed his left hand on my shoulder and started rubbing the soap across and down my back. The water ran down over my buttocks, across my stripes, to the floor. He went as far as my waist then took the soap in his left hand as he ran his right hand over my back, rinsing the soap across and off. I felt a warm glow through me as his hand moved across my skin, slowly covering every inch, and I felt my penis stir a little and begin to rise.
"My turn", he said, and we both turned around. I don't know if he noticed my arousal, but as we turned I fancied that his penis looked a little more substantial than before. I copied his movements. My hand on his shoulder felt good. As I washed his back I couldn't help but keep looking back to his bum. Somehow it looked sexier than ever. I stopped soaping and started rubbing his back. I moved my hands between his shoulder blades, down to the small of his back, and around his hip. "That's nice" he said suddenly, as my hand traced its path across his bare skin.
"Can I touch your stripes?"
Shit! It was definitely a day for impulses. What the heck was I doing?
Pause... "Uh, yeah. But be gentle."
If that wasn't an invitation nothing was. I ran a finger very lightly tracing his highest stripe, the first applied. The skin was raised fairly uniformly, with a small nub of flesh at the intersection with the diagonal fifth stripe.
I lifted my finger and took it back to the next stripe down, the third applied. This one seemed slightly more confident and deftly applied. I fancied that his buttocks were like a braille book, each line telling a story silently through touch, of the events that had brought it into being.
The next chapter, however, was one I avoided. The mean fourth stroke still looked as angry as ever, and even the sight of it brought back that terrible moment when my friend was slammed forward and frozen in a moment of distilled pain.
The next stroke down, the second, was far less threatening. I took two fingers and ran them along this stroke, then back across the speedo stripe atop his thighs.
"Is that ok?", I asked.
"Yeah" came a slight reply, just audible above the patter of water from the showers onto the tiles below. With two fingers, I started retracing my steps in a flowing motion, zig-zagging back up the corrugated lines, again missing that evil stroke before sweeping down the diagonal.
I took my palm and laid it upon his right buttock, and very lightly cupped it, feeling the discontinuities from the caning against my fingers. There was a slight "Mmm" from Greg. I repeated the process on his left buttock, then pressed both, a little more firmly. I knew this would feel good, relieving some of the sting. Greg did not say anything but leaned forward slightly, away from me, to rest his hands on the shower wall above the taps. The water was pouring down, some onto his lower back and cascading down his buttocks and legs past my hands, some onto my chest as I stood behind him. I pressed in again, then a slight squeeze, then again. He twitched slightly but remained in position. I squeezed again. Then a barely audible whisper "That's very nice..."
I was almost shaking slightly with the intensity of feeling. Here was my best friend, naked in the shower with me, offering up for massage the buttocks I had admired for so long. They were delightfully firm, muscular and taut, with no surplus fat and slight hollows on the sides. While touching him, my penis had been slowly stiffening and now stood at full erection. I was beyond caring. Besides, the sounds of heavier breathing reflected from the wall in front of me suggested that Greg was enjoying this too. I began a very slow and gentle kneading of his cheeks as he spread his legs slightly more apart.
"Hey Jeff," he said suddenly.
Uh oh, was something wrong. Don't tell me I had screwed up. "Uh, what?"
"You should try this."
I felt a thrill of electricity fire through my synapses, and my penis gave a slight jump. "OK."
I lifted my hands and Greg stood up and turned round. Another thrill went through me when I saw that his penis was also rock hard. It was the first time I had seen him naked and aroused. I had to say, I liked the sight. Just as he was taller though thinner than me in real life, so too his erect penis appeared slightly longer than mine, although with less girth. He gave a quick glance at mine too but we didn't say anything. We both knew that we had already crossed a line. I took up the position he had been in, leaning against the wall with my buttocks pushed back slightly, as he began running fingers over them.
The feeling was slightly creepy at first, a little like an insect crawling across my skin. But as I anticipated the passage of his fingers along the scarifications, it felt strangely reassuring, almost like the ritual touch of a healer. When he cupped my fleshy mounds and started the slow squeeze, I had to gasp as a powerful throb went through my groin stirring my testicles. I had never felt anything quite like it. He gently and carefully kneaded my buttocks, moving his hands back and forth to slightly different positions each time. What was so good was that this experience was being administered by the kind, safe caring hands of the one person who I loved more than anyone else in the world. And then I realised...
I took my hands from the wall and turned around. "It might be even nicer this way." I placed my left hand on his right hip and stepped forward toward him. He looked directly into my eyes with an expression conveying desire, nervousness, serenity and comfort all in one. I must have looked the same, though I was trying to feed him reassurance. I moved my right hand around to his left buttock and said "We can do each other at the same time." My left hand moved to a matching position as his arms extended and, wrapping them around me, replaced his hands in the position they had been in before. We began our mutual massage. I felt contact against my penis and looked down to see his standing beside mine, nestling next to it. But now they were not penises, they were cocks, the swollen and hungry sex organs of men, rampant weapons of lust, powerfulbringers of love.
I longed for him, felt for him so much. I stepped forward slightly to bring our bodies together, and our genitals met. Our cocks were pressed between our bellies, our balls dangling together, our firm-nippled pectorals rubbing each other. In doing so, our heads came so close that I had to move mine to one side and rest it on his shoulder. After a few more squeezes, I moved one arm up to start to stroke his back, the other maintained its soothing massage of his bum as I pressed my groin against his and felt him pressing back.
Greg ran his left hand up my back and began stroking me. His right hand started ranging over my bum, slipping his fingers occasionally into my crack. I ran a hand down to his thigh and started sliding my fingers in between his legs. He shuffled his feet slightly, spreading them to invite me in, and my creeping fingers started to brush and caress his balls which brought a gasp of pleasure.
I drew my head back slightly and we looked into each other's eyes properly for the first time since beginning our erotic exploration. His face was flushed, his look studied, intense, slightly dazed. "Oh Greg, this is so...so..." But I didn't finish. Our heads moved closer and I felt his warm breath mixing with mine, closer, closer, until our lips met in a delicate kiss - just for a moment, then again, then a third, longer time, before he brought his arm up to grip me tightly behind the shoulderblades and our mouths met for a more sustained encounter.
I felt the warmth and the love flowing between us. I ground myself harder against him, cock deliciously squeezed against his belly, feeling his hard rod digging into my stomach. His fingers were brushing back and forth against my hole and delightful spasms went shooting through me as I quickened my stroking of his balls. I was getting close. The pressure on my cock took my mind back to feeling it squeezed against the wooden beam as I was draped over the frame receiving my caning. I wondered how many other boys, left alone by the Headmaster after similar sessions, had ended up like Greg and I...
I felt a twitching in his balls as they slowly contracted, rising up, preparing their load. My left hand let them escape as I moved it to hold him tight to me. I wanted to be ready to meet him. With my right hand firmly against his bum I ground my cock against him hard and our tongues met. His hips started to tremble and he inhaled heavily through his nostrils. This was the moment. I was almost there but still not quite ready.
All of a sudden, as his body started to surge as if it had become a huge wave, I felt an extraordinary feeling. The finger that had been circling and pressing on my hole suddenly drove right into my asshole and pressed firmly on my prostate. As I felt his hips grinding as his cock fountained out its juices, I cried out in ecstasy. I felt the wave moving rapidy through my body , my balls quivered and fired salvo after salvo of cum to coat our bellies and matt our pubic hair.
The moment was incredible as we both moaned aloud. As the sticky streams subsided, our breathing slowed, our minds dulled and we wrapped our arms tightly around each other, as the hiss and gurgle of running water once more became the predominant sound, as the warm liquid coursed down our bodies slowly carrying away the semen I heard the headmaster's words from this morning echoing in my head...
"...I trust that you will find the experience - in its entirety - somewhat educational..."
Oh, and we forgot to put the frame in the gym away. But no-one ever mentioned it to us. So that's all right.
There will be more stories about the adventures of Greg and myself. Let me know if you enjoyed the story or have any comments.