A Lesson I’ll Never Forget

How had I gotten into this situation? I ask myself as I squeeze my eyes tight to stop the tears of pain and humiliation. They were getting off on doing this to me and there was no way I was going to give them the extra satisfaction of my breaking down in front of them. Or so I naively thought.

Dressed like this I could endure anything and win; they could hurt me but could not have me. They would both love to shag my tight arse and finish off putting me well and truly in my place, but they know they would never get away with it.

It all started so differently.

Gaston was the typical queer PE teacher: a figure of fun. I recalled how he had slippered me 2 years ago and I had been afraid. Now 18 years of age, and well developed, he could not do it again.

I’d had experiences with girls, but at that age I would call it bi-curious with a large dose of S & M thrown in. Fair, tall, 6’1″ and slim with long, toned legs, I was bound to appeal to both sexes. And my crime – to run the 4 1/2 mile cross-country with trunks under my sports shorts whilst no underwear –was allowed. A spot check involving a quick squeeze, then the humiliation of having to take my shorts down in front of the other boys; then Sir’s office and the instructions, “strap & punishment book at his office, 4:15.”

Lunchtime came. God I felt so fucking horny I could not believe it. I went straight to my room: this had the makings of my ultimate fantasy come true. So he was going to give me six of the best with that leather strap; I’d heard tales that it could make you scream and cry but not me, no way. I was not even concerned when he ordered me to wear correct gym clothing or face further punishment. So he wanted me in shorts with nothing on underneath. Well I was going to show him: he might have me bent over but all he can do is whack me 6 times. The bastard had always fancied me; well he can’t have me, but boy am I going to tease him in my little ‘gym outfit.’

I’d experimented on myself in this outfit before, alone in my locked room, bent over the bed in my short-shorts whilst I tried various implements on my exposed thighs and buttocks. No one else had seen me in the outfit, but I anticipated approval. In fact I planned to use it to tease him to fuck and why not? So he wanted to hurt my young body; that I could not stop. But I was going to make sure I looked great, not for him but for me. I was trembling with anticipation at what was to come. The thought of being powerless to an adult male who was going to enjoy hurting me, was too much to take; it was all I could do to keep myself from masturbating my stiff young cock. But no, I did not want to spoil the suspense and excitement that was building inside me.

So I’d packed my outfit and at the end of day bell, went straight to the head’s office, collected the strap and book then as planned shut myself away in the changing room next to Sir’s office. There would be no one about at this time (to hear my screams) and I had 15 minutes to get dressed before my appointment.

First my white baseball boots, sexy with the long laces fastened round the ankles twice with large loose bows.

Then the shorts: shiny red, a naughty colour, made of a thin slightly stretchy material with the cotton lining removed. The shorts when worn short and tight were no less than totally indecent, displaying the full outline of all I had to offer. God I loved the feel of these shorts, actually designed for a teenage girl, far too small for me and with no room for my parts. I wriggled into them, pulling them right up my crotch and stretching them so tight that my balls were partly exposed and the full shape and detail of my cock was shown. Fastened with a leather belt and pulled high at the sides and right up my arse so only a thin strip of highly stretched material ran the length of my crack. My cheeks were fully exposed and entry to my tight hole was easy with a finger without having to move the shorts at all.

Next a tight short white vest hugging my body seductively and exposing my lower midriff.

All this was finished off with red wristbands and a thick leather belt around my waist, virtually resting on the tip of my prick and covering the top of the shorts.

The whole effect was completed with a smear of baby oil to make my legs glisten and give a feel of smoothness. He would not know about the oil unless he touched me but it felt so good for me and let’s face it, if I was going to be put through this then I had to look my best for me, if not for that dirty pervert.

It would be fair to say that I looked outrageously tarty and was without doubt ‘asking for it’. I am sure that any self-respecting homosexual would have sought to have his way with me looking like this, regardless of my wishes. From hours of posing in front of the mirror I knew I looked hot; yeah sure I would suffer more through the lack of protection the outfit offered me, but it was all worth it to feel as horny as this and get one over on the dirty bastard.

Once dressed I turned my attention to the strap, exploring it with my fingers the way it was soon to explore and violate my intimate areas. A thick piece of brown leather about 18″ long with an 8″-long wooden handle at one end. The handle was made of polished wood, cut thinner in the middle to allow grip and with a 2″ thick rounded end; the leather hand stitched and worn with the clear signs of the previous pain it had dished out. The last 6″ of leather was split into three strands each about a half an inch thick. I supposed they would spread and seek out the more vulnerable areas of my body. Realizing what that could mean, I for once felt a moment’s hesitation: this is going to hurt. Too late to turn back now though: in an instant the doubt heightened my anticipation.

4:15, bang on time, I knocked at his door. God I’m shaking, but I’m so horny. I’m carrying the strap in my left hand with the large punishment book across my lower body so he could not see my tiny shorts that said from the look on his face he guessed something by the length of thigh exposed to him. More to the point I did not want him to see my excitement, which was for me; the pleasure I would get, though, from the surprise when I lay over his desk in these shorts was an extra benefit.

“Come in,” the voice said. Sir sat behind his desk and I breezed straight over and stood before him. But of course there must be a witness and I’d walked straight passed him. “Mr. Smythe will sit in on this one.” I heard a muffled cough and realized he was sitting right behind me: God another pervert and he can see everything from where he is.

“So six strokes of the strap; you have brought this on yourself boy. Hand me the book and take the position over the desk, feet in the straps, arse in the air and place your hands in the wrist straps.”

I handed him the book and his eyes nearly popped out: I swear he stared straight at my bulging crotch for a full ten seconds. God I feel so horny and I’ve got you, you bastard! You would love to fuck me right up my arse but you can’t! Bet you won’t sleep tonight.

I smiled smugly as I bent over the desk as ordered, my crotch pressed hard onto the old wooden support. Then my wrists were fixed into the wrist straps and further straps fastened around my ankles; these were adjusted and pulled apart spreading my long legs, the wrist straps were pulled tight bending me over and stretching me to my limit with my crotch squashed hard against the support. The overall effect was to leave not only my arse but also my balls cruelly exposed. God I feel so vulnerable right now but what must I look like, the thought of how many other boys had been through this with their balls pressed where mine are now just added to the excitement.

God I’m going to come in my shorts right now if I don’t start thinking about something else.

Sir had finished fastening me in my position – God the waiting and anticipation was driv
ing me crazy. I then felt his hand on my bare arse cheeks: “Just checking to make sure there isn’t anything underneath,” he says. I am sure that there was a tremor in his voice. The bastard – he could see there was no room for anything underneath; it’s just an excuse to touch me up and there’s not a thing I can do about it.

How right I was as I felt his hand between my legs, fingers slowly trailing from my balls and up the crack of my arse, lingering briefly at my hole. I squirmed unable to control the movement and a low moan escaped my lips.

“Gym kit I ordered,” he says. “You look like a rent boy. You just won’t learn will you? Six more strokes this will cost you.”

“But Sir, please,” I protested. “Shut up boy or it will be even more.”

Shit I’m in a mess now: yeah I look and feel really horny, but he’s going to use it to his advantage. Realizing that I am about to be really hurt and I can’t do a thing about it, I gritted my teeth, determined not to cave in to them whatever they do to me. It’s only a piece of leather. I’ll be all right and let’s face it: tomorrow I’ll still look great; they might get off on what they put me through, but they’ll still have regrets.

I was aware of him stepping back to my left and then a pause. It felt like an eternity. Then it happened: a low swishing sound and almost immediately a loud crack. Oh God! I felt my whole body thrust forward straining the bonds, my balls rammed hard against the solid wood. Talk about getting it at both ends. My arse was on fire, I tried so hard not to let out a sound but that fucking hurt more than I ever imagined.

Almost immediately another stroke with the same effect, hitting me slightly lower towards the tops of my thighs. I squirmed and could not help letting out a sudden gasp from between my clenched teeth.

There was now a pause for a few seconds and I was aware of him changing position, moving further forward as if to swing over the top. Too late I realized his intention, I was in a position where I was unable to do anything to protect myself anyway but at least I could have anticipated what was to come – enjoy the last few seconds of any pleasure before my balls and my whole body was racked with agony.

Again that swishing sound followed again by a sharp crack, but this time the strap had connected with my body right down the crack of my tight arse. It felt like someone had taken a blowtorch to my crotch as the leather strands whipped against the exposed area of my balls, seeking to wrap around them and almost ramming them back where they came from.

“Please no aargh!” I screamed as my whole body convulsed with pain, writhing in agony against the tight bonds. Nothing had prepared me for the incredible pain; it felt as though in addition to the thrashing, I had just been punched right in my balls.

Immediately the strap was snatched away from where it had become wedged between my cheeks, that bringing its own pain and not the erotic pleasure I had experienced minutes earlier from Sir’s wandering hand. I bit my lip anticipating and “Whack” this time the strap avoided my crack and connected full force with my firm throbbing balls. I was aware of my whole body being thrust forward again with my cock and balls against the wood. The intense burning pain was matched with the writhing doubling up agony of being whacked square in the balls.

I was aware of myself begging, offering my body, “Please, please no more! I’ll let you do anything to me but not this!” My voice was almost a sob.

“You fucking tease, I’ve waited years to do this. You are going to pay,” came the measured reply.

Another whack, striking hard to the side of my crack and stinging into the top of my firm thighs. I have no doubt the target was the same place but with what little leeway the bonds allowed me, my agonized writhing had lessened the potential crushing impact.

This clearly frustrated Sir: “Hold him!” Almost immediately I felt the witness, Smythe, force his body between my thighs, forcing them apart against the bonds and preventing any form of movement. “What a view he must have,” flashed briefly through my mind, which was now blown apart by the pain and humiliation. But no it gets worse; I felt rough fingers probing the area between my cheeks where my tight hole was protected by no more than the thinly stretched piece of red fabric.

“No no no no!” I screamed as my hole was brutally raped by viciously penetrating fingers forcing their way to the knuckle. All thoughts of my appearance and teasing outfit were now lost as I fought for some form of dignity and self control. I look so fucking good but it’s only making it worse was the thought as I pleaded for mercy.

The answer was a sequence of four of five blows across my arse cheeks in quick succession. At least whilst being penetrated in this manner I was safe from further blows to my balls, but this did not lessen the continued agony I was now suffering.

“Oh no no no!” My screams filled the air as I felt the fingers roughly removed. I was either about to be raped for real or the attack on my balls was to continue. After what came next I would have settled for the former.

I could not guess how many times that strap violated my most intimate areas, whipping my arse and firm young balls into a swollen mess. I know I was reduced to hysterical sobbing and begging at each blow – there must have been at least twenty. After what seemed like forever the thrashing stopped.

“How was it for you? Good I hope?” asked Sir mockingly. “Well how was it for you? Good I hope?” asked Sir mockingly. “Well how about some of this then?”

Sir moved behind me whilst Smythe still held my legs apart with his bulk. I felt fingers roughly tugging at the thin strip of my shorts where they were deep in my crack, then the thick wooden handle probing at my hole. Oh no this is it, I’m about to be raped with the handle, and I look so good how can he do this to me. I began to beg and plead, offering anything and everything but to no avail.

“You will not forget this,” said Sir. He then rammed the thick handle inside my tight virgin arse. I tensed and tried to resist but to no avail, it only made the pain worse. I felt my arse stretched to the limit; god he’s going to split me in two. I was aware of the handle being pulled part way out then thrust deeper inside me as I screamed and writhed against the bonds. I was aware of searing agony as he began thrusting the handle in and out, each stroke seeming to go deeper than the previous, with my no doubt getting the full 8″. At some stage my bladder let go with hot steaming urine soaking through my tight red shorts and running up and down my crack before flooding down my thighs to make a pool on the floor.

The handle shagging must have continued for a good five minutes – it felt like hours – as I screamed and cried hysterically, all the while writhing in agony.

I must have been semi-conscious when the sadistic abuse finally ceased. I recall the bonds being untied and my long lean body sliding to the floor. I was unable to control the involuntary writhing movement of my thighs, rhythmically pushing together and pulling up into the fetal position before extending fully as I squirmed in agony in my own urine.

Looking back now the outcome was obvious from the moment I decided to use my scantily clad body in an effort to get one over Sir whilst submitting to such a vulnerable situation. I must have looked so fucking horny writhing about on that floor, tears streaming down my face and my arse and thighs a mass of bright red welts.

So horny in fact that I was suddenly aware of being splashed over my exposed arse and thighs with warm sticky goo. I briefly looked up from my position to see both teachers standing with their erect shafts in hand aiming at my body, a spray of spunk showering my arse, thighs and worse still snaking into my now stretched arse.

“You bastards,” I managed to sob in protest to my regret as it was met with instant retribution of the most vicious kind. Sir squatted beside me, grabbing my belt and pulling me onto my back. I tried to force my thighs together anticipating what was to follow, but I was prevented by my legs, over which I had seemed to have lost all control. He then delivered four sharp solid punches directly between my legs, his clenched fist connecting repeatedly with the thinly stretched material covering my already bruised and swollen balls, leaving me again sobbing and writhing in pure agony in the mess of urine and spunk on the floor.

A short time later I seem to recall being carried next door to the changing rooms where I was roughly stripped naked, all vestiges of modesty now gone in my total and utter humiliation. My naked body was then washed thoroughly under a cold shower, clearly to remove traces of spunk before being left lying on the floor with orders to get dressed and leave.

Somehow I managed to dress myself, stuffing my ‘gym outfit’ into my pockets before staggering back to my room under cover of the winter darkness. I took to my bed for 3 days telling my House Master that I had a bad stomach. I was certainly suffering low down but it was not my stomach. I recall lying there that night sobbing with the pain of the fresh damage to the most intimate areas of my body.

I was never again tempted to cross Sir. In fact my skin would crawl as he looked at me at times with a knowing look that said, “I’ve had you.” As for my teenage curiosity, I still enjoyed occasions of being on the receiving end of pain from time to time but I never ever put myself in such a position again.

In time the mental and physical wounds healed. But without a doubt that day I learned “a lesson I shall never forget.”