Caught in Miss Louise

Ms. Louise

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Caught in Miss Louise’s Leather Pencil Skirt

Miss Louise has been a teacher for a short while at my boarding school and has certainly made an impression. She has lots of elegant and sexy clothes, clearly enjoys wearing them, and looks particularly wonderful in her pencil skirts (a fact she seems to know and flaunt). When she wears her pencil skirt, her thighs and perfectly round bottom are teasingly outlined as her heels click along the school corridors. At first, when she passed by, heads used to turn accompanied by low whispers. But then one day she publicly caned three boys foolish enough to make a comment out loud. She lined them all up in the central court, told them to drop their trousers, let everyone know exactly why they were being caned and gave each one twelve strokes. Each boy’s skin broke before the sixth stroke, such was the ferocity of Miss Louise’s caning. Now, as Miss Louise passes by, everyone is much more careful about hiding their admiration of her perfect form.

I fantasize incessantly about wearing Miss Louise’s clothes, about how it would feel to have the skirts (that have been so tight around Miss Louise's thighs and pert bottom) tight around my thighs and ass. The school is quite a distance from the city and has some nicely furnished apartments for teachers who prefer not to make the long journey each day. Miss Louise lives in one of those apartments on the edge of the school grounds. One day, knowing that she is in a class, I pluck up the courage to sneak into her room and try on some of her skirts. I choose 3 of her best silky satin skirts: a red stretchy satin pencil skirt with a buckle at the front and a long slit at the back, a black satin skirt with cute little pleats at the knee and a grey silk whisper soft silk skirt that embraces Miss Louise’s thighs then floats very sexily around her knees as she walks. I carefully lay them on her chair and bed and gently stroking each one in turn.

I decide to try on the red satin skirt first along with a pair of thigh highs from Miss Louise's drawer. It feels amazing as I squeeze into her skirt and feel it sliding over my thighs and ass. Just as I am looking at the skirt pulled tight around my ass, I hear the familiar click of Miss Louise’s high heel boots outside. How could she be returning so soon? Shouldn’t she be in class? I frantically look round her room to see if I can hide and see my clothes heaped in a corner and her skirts spread widely apart. Too late to change back into my clothes, I grab them and throw them under Miss Louise’s bed. I then pick up Miss Louise’s 2 other skirts and start to bend down to make it under the bed along with my clothes. Just then I hear the door knob turning and realize that Miss Louise’s red satin skirt is too tight for me to kneel on the floor. The door flies open as I am bent over with my red satin ass sticking ridiculously up in the air. In walks Miss Louise looking like the perfect schoolboy’s fantasy of a school ma’am. She has a long sleeved cream blouse and a very tight knee length leather skirt above equally tight long leather high heeled boots. Miss Louise seems speechless for a few seconds, with the sight of her red satin skirt thrust into the air on someone’s ass. Very quickly, however, she regains her usual confident control and asks sharply what on earth I am doing. I stumble and mutter and finally explain how much I love her clothes and wanted to see how it felt to wear them. I notice a smile appear on Miss Louise's lips as she then explains that my behavior is disgraceful. Without explaining why, she starts referring to me as a little girl and then names me Sasha. “My dear little Sasha, you are about to be disciplined more severely than you have ever known or can possibly imagine. I will bring out the little girl in you, Sasha, and then thrash and humiliate you so this little girl never wants to make another appearance anywhere, let alone in my bedroom.” Now I understand.

Miss Louise explains that she will not be using any of her usual punishment implements - she will be bring out her most severe tools, the ones she saves for only the most serious offences. She also tells me that she is going to cure me of my desire to wear women's clothing by making me put each one on of the skirts I’ve chosen then thrashing me so every time I think of her skirts in the future I can only remember the blistering pain I am about to experience. She then brings out a dizzying array of spanking implements (straps, taws, paddles, wooden spoons, brushes, canes). Finally, with a smile, she goes to her stocking drawer and produces a very realistic looking strap-on cock. Seeing the look of dread on my face, Miss Louise walks right up to me, waves the cock in my face, smiles and says "Well now Sasha, if you want to be a girl I feel obliged to give you a comprehensive girl experience." She then lines up the spanking implements against each skirt and tells me that she whenever she wears each skirt in the future (for as long as I am at the school) I will have to remember every implement that was used with each skirt. If I forget any implement then I will be sent to her private room to put on the skirt in question and receive 100 strokes of each implement I miss. She also explains that her memory sometimes plays tricks and she may just remember a few more implements than I can - so she wouldn't be at all surprised if I was to make two trips per week to her study for the next 6 months to receive several hundred strokes of the strap, paddle, cane or spoon.

“Right Sasha, straighten your red satin skirt and come over here to my chair. As you are going to be wearing my skirts, I don’t want to break your skin, but I do want you to subject you to a great deal of pain. Consequently I am going to have to warm you up slowly so your skin is prepared for the heavier punishment to come later. Now bend over my knee for a gentle warm-up with this hairbrush.” Feeling confident that this won't hurt too much I casually waltz over to Miss Louise who pulls me across her leather lap. True to her word she gently strokes my satin-clothed ass with the shiny surface of the brush telling me that she wants me to feel like a girl and that I should push out my bottom like a pert little girl's bottom. Feeling comforted and slightly aroused I push up my ass eagerly to receive the hairbrush. For some bizarre reason I actually want Miss Louise to hold me like this forever and to spank me gently. But then the first stroke lands with an ear-splitting "WHAP" and my ass burns with the sharpest sting I've ever felt. I can’t seem to breathe and just as I am catching my breath “WHAP”, down comes another eye-crossing swat. Four more carefully spaced swats land on my ass cheeks as I squirm wildly on Miss Louise's knees. Miss Louise explains that all my punishment will be delivered in sets of 6 but I am incapable of comprehending. All of my senses are overloaded with the unbelievable burning sting in my ass. After 10 sets of the hairbrush Miss Louise tells me to stand up and bend over the back of her chair.

"I can't possibly hurt you with my strap if you are over my lap Sasha, I need to be able to swing it properly, and of course I am going to hurt you very very much with my heavy leather strap little girl". Miss Louise never exaggerates. This is once again proved true as the silence is broken with a deafening “CRACK” followed in a millisecond by a stab of pain that enters through my ass and explodes through to my chest. “Did you enjoy that Sasha? ‘CRACK’ Well you are in luck little girl, ‘CRACK’ because you are going to receive sixty ‘CRACK’ strokes of my strap in total ‘CRACK’. It really is your lucky day isn’t it Sasha? ‘CRACK’.” As promised, Miss Louise paused after this, and every set, of six strokes, just long enough for the full after effects to be felt. The “aftershocks” seemed almost as painful as the blows themselves – waves of burning sting rolling through my body. Miss Louise seemed to know just when they started to subside. Whenever I could finally start to relax, another ‘CRACK’ announced the start of another six strokes of Miss Louise’s spanking implements.

After an assault with a wooden spoon (where on earth did she find one with a handle that long and a bowl that big? And how the hell can she make it hurt even more than that long, thick, dense leather strap?) I finally get a short break. “Right Sasha, time for a new skirt. I’d like you to put my red satin skirt back where you found it and get changed into my black satin skirt. When you have it on, lie face down on the edge of my bed.” Somehow, I thought to myself, I won’t be lying on the bed for an afternoon nap…

Nobody at school knew it, but Miss Louise was quite a collector of severe spanking tools. One particularly effective tool was a genuine extra-heavy Lochgelly taws from the 60s. “Sasha, you should be honored. This taws took me 3 years of searching to locate and several hundred dollars to purchase, but I have never had the opportunity to use it. The thing is that the Lochgelly taws should always be brought down vertically from over the shoulder, usually onto the hands, but I prefer to spank naughty girls on the bottom which means they have to be lying down to receive it. You are the first to be spanked in my room, which means you are the first person I can spank properly with this taws.” From my prone position I watch Miss Louise as she draws her arm back and lets the taws drop behind her shoulder. She looks magnificent as the leather strains against her soft thighs and her breasts pull against her blouse. In this very moment, I want Miss Louise to spank me mercilessly until she is satisfied I had been adequately punished. I no longer want to escape and cut short my beating. I want her to punish me until she feels satisfied. And I want that Lochgelly to burn itself into my ass. Miss Louise, and her Lochgelly, don’t disappoint. I bury my head in the bed sheets and breath deeply as ‘SMACK’ after ‘SMACK’ assaults my sorely beaten ass and as I surrender to the exquisite pain of her spanking.

After the Lochgelly came another heavy strap then a thin, stingy sorority paddle. And then another change into the final skirt, the grey silk skirt. Miss Louise began this skirt with the Lochgelly. “I quite enjoyed using the Lochgelly Sasha, but I feel I need to perfect my technique. 60 more strokes should do it…” This time however, the thin silk seems to intensify the strokes. A thin film of sweat seems to be making the silk stick to my skin and concentrate the effect of each blow.

“Don’t think I haven’t noticed, Sasha, that you are sweating onto my skirt which means I will have to get it cleaned before wearing it. As punishment I want you to return to my room tomorrow. You will receive 50 strokes of the whippy cane on the bear ass.” “Yes Miss Louise” is all I can muster.

"At last Sasha, we have reached the final stage of your thrashing for today. Fetch my long cane. You thought my paddle hurt? Well it is nothing compared with what you are about to receive. Now bend over so I can thrash you properly Sasha."

‘WHOOSH-THWACK’ comes the familiar sound of the cane slicing the air then landing brutally on silk-clad flesh. The sensation however is less familiar. An intense sting followed a second later by a deep surging ache pulsing right through my body. I say a silent thank you that Miss Louise doesn’t want to break my skin. I’m not sure I can handle any more pain than I am feeling right now.

After my caning I start to stand up but Miss Louise tells me to stay where I am. "Time to complete your experience, so lift up your skirt Sasha, and stand with your feet wide apart so I can penetrate you with my latex penis" Miss Louise slips out of her leather skirt, then pulls on her strap-on and gently fingers my ass with lube, slowly penetrating me with her gloved fingers. After a few minutes she gently places the penis on my ass, pushes slowly inside and fucks me while telling me what a naughty girl I am and that every time I visit her study for a spanking I am to be penetrated with her penis like the little girl I am.

"Now Sasha," says Miss Louise, "you need to show proper respect for a woman and realize that you can never achieve such beauty and perfection. You will show your respect and adoration of women by worshipping my skirt. Come over here and gently kiss my thighs through my tight, shiny leather skirt". Miss Louise then points out the areas that I can never copy - the soft thighs, the round ass and makes me worship each slowly and thoroughly until I am spent.

After the worship Miss Louise reminds me that this is just the first thrashing and humiliation of many that I am to receive. "I will be wearing that red satin skirt in 2 days time Sasha. If you can't remember every implement that was used on you in the correct order with each skirt then you will be back here for another thrashing Sasha. Then I will penetrate you again and make you worship my skirt again. The rest of your days at school will be very painful and humiliating Sasha. Now, get out of my study little girl!"