Dirty Lesson

The wooden chair outside the heads office had seen my backside more than once. The secretary glanced at me through the open door and slowly shook her head to herself. It was familiar to see me there. I’m not exactly a bad person, it’s just that whenever I act the goat or get up to mischief, I always seemed to get caught. This time though I was fighting and deserved to be in front of the head once more.

We all knew that there was a temporary replacement in at the moment. We had seen her taking assembly. Some hard nosed bitch, only young it seemed, taking control of the school temporarily. Even the teachers treated her with disdain we gathered. Working her way up the ladder and furthering her experience and CV as much as she could. Well it would not work with me. I had my reputation to keep.
I looked at my clothing, my gym kit was dirty and sweaty from the track (running was my forte, the gym master wouldn’t normally let me do contact sports because of my short temper, unless there was a competitive fixture where he needed me) but still smart in my white shorts and rugby top. The door opened and the headmistress motioned with her quick nod for me to enter. I strolled in trying to make it look so matter of fact. “Stand up straight Taylor” she said. I looked up straight into her eyes smirking, trying to look the ever present rogue, but she just stared at me with such repugnance, that I dropped my smirk, and just met her stare and felt her eyes burning into me. For the first time I felt belittled by a teacher at this school. This woman obviously exuded confidence and authority. I could feel this just from her stare. I stood straight and looked at her.
“This is the first time I have seen you Taylor, but it appears that its not the first time you’ve been in here is it?” “No miss” I said. “So what is it? Why do you have to rebel against the system? For goodness sake Taylor, you are 16 years of age and still not accepting that you are nearly adult. Tell me what to do with you?” “Pardon Miss?” I looked at her standing there, black headmistress’ robe, black trousers, high heels, not too high, white blouse with a black cravat looking all the more a figure of authority. Good looking woman too…”Well?” the sudden sound of her voice brought me from my daydream. “Sorry Miss, I don’t know Miss, I thought that was your job Miss.”

She sat down with a sigh, “Its supposed to be isn’t it, but whatever this school does to try and tame you it seems they and you always fail”. Sitting back in the large chair, I looked at the perfectly formed breasts under the crisp white blouse, the perfectly made up face……….christ what was I doing?? This is a head teacher for christs sake. Here I was getting seriously turned on by a woman who was supposed to be my arch nemesis. I flushed red as I realised that my eyes had betrayed me and the blood pumping through me was now finding another channel to flow through.
I lowered my head, trying not to look at her. But my state of arousal was all too apparent. Face flushed, breathing increased, and there was of course the fact that I was concealing myself by pulling down my long rugby top.
“Can we just get on with it Miss,” I said holding out my hand. I looked in the corner at the umbrella stand. Selections of canes, slim and long were standing in there. A few quick strokes, sudden sharp pain, burning for a while then it was back to the field. She stood up and moved to the corner retrieving one of the implements. Standing in front of the window, silhouetted against the light, I looked at her. Legs apart, bending the cane in her hands and…did I see that? Did she just wet her lips? Did I see her tongue? Once again more blood surged through me. I was only 16 but was not short of sexual encounters, when you are the school bad boy it was not hard to get the right kind of girl. I recognise a sexual signal when I see one. But I must have been wrong, this was the head. I was in the dusty, old, book covered office where countless times before I had seen the cane in the hands of wrinkly old Hawksey the old head. I held out my hand further. “Need to get back to the field Miss, we got a game tonight, have to practice,” Once again the eyes boring into me, “Ahh! yes, our star rugby player, talented young Mr Taylor, very good at contact sport, loose cannon, troubled teenager, I’ve read your reports”. She walked towards me and stood side on. I gulped; from where she stood – Miss Petter… my excited state was all too plain to see. I saw her looking down and again the wetting of the lips…….I saw it, I did. The cane placed on my hand. I waited for the familiar swish and then delayed pain to register, burning.

“This is too easy for you isn’t it boy?” I looked at her. “Miss?” I said.
“Its too easy, too familiar, its not helping you or us to simply hit you on the hand. There’s something else troubling you and I intend to find it”. I almost laughed out loud, I had heard this so many times. Troubled boy, teenage problems. Peer pressure. What could she possibly find in me, many others had given up trying to look for.
“Bend over that table”. “Wh…. What Miss?” “You heard Taylor, now get over the table”.

This was unusual, I only ever got my backside whacked by the games teachers and their slippers or trainers, and they were male.
My heart sank and pounded, was she serious? She tapped the cane on her hand pointing it at the table. I nervously leaned over the table, absolute terror now inside me, my face was cold and sweating at the same time, my heart in my mouth. This one was clever, very clever. It hadn’t taken her 5 minutes to instil in me the fear that no other teacher or head teacher had managed to.
I could resist, easily, I could just walk out, she couldn’t stop me. But I was aware that I was 16 and also aware that I needed my education if I was to succeed. I made trouble because I enjoyed it, it was fun. I knew the other kids looked up to me and I was their dis-jointed hero. It was expected. So I wasn’t going to run or walk out. I would take my punishment as always. I heard her move behind me, my fingers squeaking on the polished table as they searched for a grip. Then the swish of the cane in the air, my eyes closed tight teeth clenched. The cane hit my flesh so hard I nearly fainted, the searing pain on my skin burned like fire. My legs nearly buckled, tears welled in my eyes. Another swish and the cane once more flashed onto my backside, the pain even worse this time as the cane was raised and thrashed against me; six times, seven times…..I started to sob in my throat as the pain and humiliation hit me. I covered the sobs with a grunt, trying ever so desperately to hide my pain. 11, 12 times then she stopped. I was in pain, far worse than on the hand, she knew how to use that cane; but I wasn’t going to show it, I had an image to uphold.
I was now lying on the table, my chest against it, tears running down my face. Not from the pain, I could take that, I was humiliated. The pain on my skin was like nothing I have ever experienced. I was aware of another feeling too, I was as horny as hell, my cock was so swollen that it was painful to lie on the desk. I could not move… for both reasons. “Stand up Taylor, stand up now!!” I pushed myself up and straightened my clothes, wiping the tears on my sleeve. “Turn round”.
I turned slowly to look at Miss Petter, trying to put defiance in my eyes but they were still full of tears from the thrashing she gave me. “Well what do we have here?!! It seems we do have emotions after all”. I looked at her face but she wasn’t looking at mine, she was looking at my crotch. “It seems young man that you are not decided over the punishment you have just had, humiliating to be brought to tears by a woman? Or did you actually enjoy it?”
What the fuck was she talking about? Enjoy it? I was in agony, my flesh was raw and throbbing with the thrashing she had just given me. I was speechless and just stood before my better. I knew it, she knew it.
She came close by me, still holding the cane, tapping her hand with it. She put her face close to mine, I could smell the perfume of Petter, feel the breath on my face. “Tell me you will not be in this office again Taylor, tell me that the boy has become a man once and for all”. Her face was so close to mine now I could feel the warmth on mine. What the hell is she doing, I stood straight, trying to compose myself. My throbbing member suddenly touched by something, I jumped and looked down, looking at the cane resting on my cock. I was bewildered, this was the head teacher, what was happening, is my humiliation not enough? Now I am being toyed with, humiliated further. My breath caught in my throat as the cane was pushed harder down onto my cock. “It seems that the man trying to break free, may need some assistance Taylor”.
She stepped behind me and locked the office door. Turning to look at me she removed the black cloak and hung it on the old fashioned coat stand.

I was dreaming wasn’t I? I wasn’t here, the searing pain on my skin was now a hot feeling, still stinging but now a different sort of feeling, it felt good; it was making my heart beat and the blood flow to my cock, which was now the centre of her attention. Here I was a 16 year old faced with my head mistress unbuttoning her blouse. I watched as she revealed her breasts to me encased in black lace. I couldn’t move, I just watched as she walked round me. Standing there in my gym kit, my shorts stretched tight over my bulge.
She stood in front of me and turned her back to me. I looked at her smooth skin, smelling again the perfume, this time mixed with something else, which seemed to make my pulse quicken and male instincts take over.
I reached for the catch on her bra and released it, the elastic springing free as she covered her breasts with her hands. Turning to face me as she removed her hands, the bra falling to the ground, I was faced with the most gorgeous pair of breasts I had ever seen. We both stood there looking at each other. I dared not move, she licking her lips again gave me the signal I was looking for. I moved to her and lowered my head to her nipples as her hands held my head, pulling me towards her bosom. I opened my mouth as the cool nipple slid between my lips and I raked my tongue over it, sucking it into my mouth. My finger and thumb rolling the other nipple gently, my hands feeling every part of her large breasts. Then I felt her hands on my shoulders pushing me down. I was still dumbstruck to be in this position with my teacher, the person who was responsible for my education. I knew that this was taboo and both of us could be expelled from the school. Did I have her now? Was this my chance to get rid of the bitch? No I don’t think so, even though we all thought of her as a bitch, it was obvious that she was hot. I could never live it down if I opened up. She knew this, she also knew that this would be my portent, my final passage into manhood, the boy gone, the man emerged. I was right she was clever.
I was on my knees before her. I didn’t look at her face as mine was level with her crotch. Hands on my head, forcing my face into the front of the trousers, only a thin layer of material now separating my mouth from her centre, from her sex. I breathed in; the smell and pungency of her arousal filling my nostrils and releasing still further my so far unleashed male hormones. The lust finally overcame me as I grasped her legs and pushed my face hard against the covered crotch. Feeling the warmth of the forbidden valley. I felt her hands undoing her buttons then I was pushed away as she removed her trousers, kicking them off; and I saw the black thong my head teacher was wearing.

She beckoned me to her and still on my knees I shuffled closer, “Take it off Taylor”. As I lifted my hands they were quickly returned to my side with a flick of the cane. My fingers hurting. “Not with those, use your teeth”. I was in wonderland as I closed my teeth on the lace over her crotch and pulled down with my head. The material moving slowly down the legs as I pushed it down to her feet, first one leg lifted then another as I removed them completely. Just as I was about to release the thong, her foot pushed my head to the floor hard. My face mashed against the wooden parquetry.
Nothing was said. I remained that way for a few minutes as I felt her eyes on me. She was just letting me know who was in control as she ground my face into the floor with her prim high heels. Then she let me go and I looked up. The next view of this woman has remained in my head for all the years in between then and now.
Standing over me, hands on hips and naked except for the shoes. Her pussy on view to this subservient. Breasts outlined against the white ceiling. She pushed me down with her foot till I was on my back. Standing over me one leg either side of my head. She lowered her crotch to my face and held it an inch over me. The muskiness reaching my nostrils and sending pheromones surging through my veins into my body, making me tremble with lust. Then she lowered herself to my mouth and my eyes closed as I pushed my tongue into her, but not her pussy, it was her anus; and I could not resist as she forced it down onto me with all her weight. I was at first reviled by this second taboo for me…it was not natural, I had never even thought this was sexual, but after a few seconds of struggling I did not resist and pushed my tongue in and out of her licking all around her as fast as I could. This teacher was certainly earning her money, in ways probably not mentioned on the curriculum.
My head was spinning as I started to lose control because of lust. My tongue plunging deep into her anus again and again. I could smell and taste her juices running down into my mouth from her swollen pussy. My sight masked by her body. She forced herself onto me harder pushing her rectum onto me with so much force I was almost suffocating. I was aware that she had her fingers on her clitoris and was rubbing it frantically as I licked as hard as I could. Then suddenly she slid back and it felt like my entire face was engulfed in hot wet pussy as the taste of her filled my mouth, juices running down my face and into my mouth. I pushed my tongue into her, the fleshy folds parting far easier than her tight ring had just done, I could feel the insides of her vagina with my tongue as I thrust my face hard into her; as she pushed down on me so hard that I could not breathe. I struggled for breath as this feminine mask prevented me from breathing, her hands holding down my arms as I became frantic, suffocating under this woman. Then suddenly she lifted herself and I gulped in air, my lungs hurting. My body going limp as my chest heaved and struggled to fill my lungs.
I looked up at this woman over me, the surreal situation of this older, more experienced individual, holding me down, forcing her will on me, teaching me a lesson that has stood me in good stead since.
She stood and left me on the floor. “Take your kit off”. I was commanded. I started to rise but again the cane streaked across my skin, this time the front of my bare thighs. I stifled a scream as the pain surged through my body. “You will not get up; take them off lying on the floor”. I rubbed at my reddened skin, the welts already showing on my legs. I wriggled round on the floor as I took off my shirt, the cold wooden floor on my skin. Then my face reddening also as I pushed down my shorts to reveal my throbbing cock. I lay there naked on the office floor.
She walked round me, inspecting and prodding me with the cane. I watched as she walked, her hips swaying, her heels clacking on the floor, her breasts moving in time with her movements. I could still smell her, my face covered in her wetness, still sending her sexual signals into me. The cane touched my swollen member and I grimaced as she raised the cane and whacked the side of my cock, the pain shooting up into my crotch; but at the same time, pumping more blood into it. The cane streaked down and hit me on the other side, making me rise off the floor as this sudden pain shot through me. I was now so hard that it hurt with every pulse, every throb made my cock move in time with my heart beat. She then hit my legs again on the insides, making me open them so she could stand between them. I looked up at her, a second image burned into my mind for all my eternity…
She sneered at my erection and pushed her foot onto my crotch, squashing my balls and cock against me with the sole of her shoe, using her heel to stab me causing more pain to shoot through me. She then moved her foot against my cock, making the foreskin roll back and forth, whilst at the same time her heel would dig into my balls, causing these unreal sensations of pleasure and pain to course through my body. She pushed harder steadying herself against the table so she could direct her weight more accurately onto me. Forcing her foot so hard onto my cock, that once again tears started to well in my eyes.
On and on she rubbed, brutally punishing me I thought, so that the skin was becoming raw on my cock. The rough underside of the leather sole rubbed against the head of my swollen, hard member; this woman forcing her foot onto my crotch with all her weight. I was now totally at this woman’s mercy, and would gladly have lain there and endured anything that she would have wanted me to. I was hers to do with, whatsoever she desired; and I would instantly carry out her every whim, now and for as long as Miss wanted.
I looked at my cock under her shoe. The dirt from the shoe bottom was now all over my crotch and it looked red and sore. She continued to cause me pain and pleasure at the same time, my emotions getting the better of me as I didn’t know whether to groan with pain or moan with enjoyment. My breathing increased in between my quiet sobbing to myself, as I could feel my peak closing down on me.
The foot started to rub faster as Miss obviously sensed that I was closing fast on my orgasm. The pleasure and pain increasing as she moved faster and faster, one slip from her and I could be seriously injured, but I didn’t care. The sensations from her shoe now mixed together so that there was now no longer any distinction between the pain and pleasure. There was just constant pleasure from her administrations. I suddenly stiffened and she quickly rubbed her shoe faster on my cock as it exploded and my peak arrived. I writhed on her floor in so much pleasure that I was crying with the force of this overwhelming emotion surging through my young inexperienced body. My cock jerked and jerked, pumping out endless amounts of young virile sperm onto my body, the wooden floor and her shoe. I could feel the come lubricating the bottom of her shoe as it slid against my cock, now warm and soft.

As my pulsating cock came to rest, still with her foot on me, I opened my eyes and looked at her. There was no smile, only the look of my superior, my better, my Mistress. I was hers to command and she knew it. Even if I never entered this office again, I was hers and I could not disobey her.
She lifted her foot from my crotch and frowned, she had noticed that there was come spattered on her black shoe. She stepped closer to my head and wiped her shoe from side to side on my face, the rough leather chafing my skin as she did so. I did not protest. She motioned for me to lick her shoe clean and I put out my tongue as she cleaned her shoe on me. Finishing off by wiping the sole of her shoe across my tongue several times as if it was a simple doormat.
When she had finished this, she forced my face to the floor with her now spotlessly clean shoe and using the cane, indicated the splashes of come on the varnished wooden floor. I knew what to do; and with her foot pushing my face to the floor and the cane directing me to each spot; I licked the floor clean for my Mistress. The saltiness of my own ejaculate tasting bitter on my tongue. I noticed from the taste that some of the splashes were not from me, but must have come from Mistress, there was a large patch of wetness on the floor right where she had stood whilst letting my cock enjoy the sole of her shoe; and I cleaned this part of the floor with more enthusiasm; which did not go unnoticed by Mistress. A swift slash of the cane on my skin was enough to move me on. I was still on my knees my tongue licking the come and dirt from her floor, when a knock on the door jolted me back to reality. She dismissed the caller with a strict instruction to wait five minutes and then proceeded to make herself the hardnosed bitch once more. I did as I was told and put my clothes back on. Making sure there was no sign of my encounter with Mistress. I stood arms down awaiting my final instruction.
“I trust this little matter of young Taylor causing problems for my school will not arise again?” She looked at me with authority and the headmistress returned. “No Miss Petter”. I replied. “Good, then lets hope that today sees the new less aggressive Taylor and new studious man I know you can be” “Yes Miss Petter”. I replied “. “One exception Taylor” she said “Yes Miss Petter?” “Maybe the aggression that you normally utilise on the teachers and pupils of this school can be fully channelled against the opposing team in tonight’s Rugby game?”
“Yes Miss” I smiled.