My Sweet Degradation

by J Phillips

  As Miss Grant carefully helped Samantha away from the fireplace, soothing her tired arm muscles as she moved them to her sides, she spoke with her usual confident tone.

  ‘Well done, Samantha,’ she said. ‘I have a good feeling about you. I don’t expect to hear that you’ve been misbehaving ever again, and if I do I have many other punishments at my disposal, but none in quite the same vain as you’ve experienced here today.’

  A finger stroked Samantha’s flushed cheek, and she opened her eyes to meet Miss Grant’s stare.

  ‘I may be the discipline officer here at Saint Hilda’s, but I’m not all bad,’ she said. ‘As you’ve discovered, I am quite capable of administering both pain and pleasure, and I’m happy to offer either depending on circumstances. From time to time you will be called to my office so we can review your progress, and appropriate punishments or rewards may be offered. And let me tell you, my good girls always leave those meetings with a smile on their faces. Is that understood?’

  Samantha nodded shyly. ‘Yes, miss,’ she said politely.

  Miss Grant smiled that beautiful smile and Samantha felt her heart skip one last time. ‘Good girl,’ she said, taking Samantha’s hand in her own. ‘Now, run along and I’ll look forward to seeing you again very soon. And Samantha,’ she added, peering over her glasses a little more sternly, ‘no more cigarettes, please. Smoking is such an unattractive trait in a young lady.’

  Samantha offered a brief nod by way of response, and the discipline officer gave Samantha’s hand a gentle squeeze.

  ‘Oh, and help yourself to a lollypop on your way out. I know very well that you want one really.’

  ‘Thanks, miss,’ Samantha replied, stepping to the desk on shaky legs and picking out a pink and yellow lolly from the jar.

  As she popped it between her lips, tasting the sugary, strawberry goodness slip across her tongue, she walked towards the heavy oak door and reached for the handle. She turned to take one last look towards the discipline officer, but she was once more facing away, once more staring out of the large window at the playing fields beyond, and Samantha considered that it might not be such a bad thing to at least try and be a good girl. Well, for a little while, at least.

  The Erotic Advancement of Little Red

  Once upon a time, in a land far away, lived a beautiful young lady by the name of Little Red. Red wasn’t her real name of course, and it had been many years since you could fairly describe her as being ‘little’, but it was what everyone had called her since the first soft fuzz of fiery red hair had appeared on her head as a babe in her mother’s arms. There were only a few left in the village who could actually remember her real name, and even Red herself would have to think hard on it if ever she wished to be reminded.

  As a child she had hated her red hair, as the boys in the village would pull at it and call her cruel names like ‘carrot-top’ and ‘copper-knickers’. During her journey towards adulthood, however, its tone had progressively softened until it settled into a rich, lustrous auburn, which she would take great care over washing, scenting and brushing until it shone like a polished horse chestnut.

  It wasn’t only her hair colour that changed over those years either, as Red blossomed into an extremely attractive young woman. And those very same boys who had once teased her would now find themselves tongue-tied and awkward when in her presence.

  Yes, Red was by far the prettiest young woman in the village. Beyond the long, silky-soft hair that now fell well below her shoulders, she had eyes as deep and as green as a millpond at sunset, a laugh that could melt the iciest of hearts, and lips full, soft and utterly enticing.

  Red’s body had developed too and was now as ripe and as juicy as a late summer pear. She was long in the leg and slim around the waist, she had curves just where they counted, and she’d been further blessed with a fine pair of breasts that were the envy of every woman over a certain age, and were often discussed in the smoke-filled corners of hostelries for many miles around.

  Although Red’s family owned a handsome, dapple-gray draught, a dairy cow named Thistle, three goats and a good dozen or so hens, times could be hard and her father kept a tight grip on the purse strings. This, much to Red’s displeasure, meant that there was rarely money left over for little luxuries and what clothes she owned had been patched, darned and handed-down several times over. Consequently Red had become something of an expert with needle and thread, and although she always tried to look her very best, there was only so much even she could do to adjust a dress, a skirt or a blouse that she had simply grown out of two years prior. Thus her clothes would be that little bit tighter and that little bit shorter than was perhaps decent in a young lady of Red’s shapely dimensions – a fact that was rarely complained about by the young men of the village.

  Now, although Red was hardworking, intoxicatingly beautiful and generally kind of heart, she was not always the picture of innocence I may have led you to believe. She had never actually been with a man, of course, yet that certainly did not stop her from thinking about it. In fact, over the last few years Red would find herself imagining that very thought several times a day. And when that strange tingling sensation would take a hold of her senses, she was not at all averse to skulking away to the meadow – where the long lush grass would conceal her presence – so she could lie down on her back, lift up her skirt, and allow her hands to slip down between her thighs. Red would return to the farmhouse some time later, rosy-cheeked and with a look on her face that would have her mother worrying that Little Red had caught a chill.

  She was an inquisitive girl, and over the years had become quite a student of the male physique. She’d obviously paid quiet attention to her older brothers as they grew from boys into men, and on several occasions had secretly observed the village lads as they washed naked in the stream. But by far her favourite lessons were learnt when she would creep out of the house late on a Friday night to peer through the windows of the old bunkhouse where the farmhands resided. Once there she would watch what the occupants got up to with the local girls they would bring home from the hostelries, drunk and full of amorous intent.

  Red was a farm girl and therefore no stranger to the rutting of beasts, but at first it shocked her to witness sexual congress between a man and a woman. She had been surprised by the change in a man’s thing – as she’d first known it called – as it grew from soft to hard, but soon she began to marvel at such magic and to wonder how it might feel if she were the one to offer it a tender caress. She would memorise the vulgar words she’d heard gasped in the throes of passion, and would take secret pleasure in repeating them aloud to herself when no one was there to hear.

  Red had watched in awe as the village sluts took stiff cocks into their mouths, and how they would suck on them until the men would cry out and spill their sticky white cum across their chests. She had watched them fuck in all kinds of positions and had even seen a man use his tongue to lap a young lady’s pussy – a young lady who, incidentally, looked an awful lot like the vicar’s daughter.

  That had been her absolute favourite new word; ‘pussy’. She thought it so fitting, as she’d discovered her own to be just as soft and just as tender as a newborn kitten. On those nights when she would observe the farm workers at play she would inevitably find her own palm sliding beneath her nightshirt, where it would tease her clit in just the way she liked while she imagined it was she in there with them and that it was her body they were making use of. Soon enough Red would be forced to bite hard against a knuckle so as to stifle the cries of pleasure she’d unfailingly release before she would dash back across the darkened yard and quickly on up to bed.

  Poor Red longed to experience a man for herself. While her friends would giggle and pull faces at how disgusting it all sounded, Red’s eyes would mist over and she’d dreamily imagine how sweet it would be to close her lips around a gentleman’s big hard cock and to suck on it until he was forced to
groan with the pleasure she had bestowed.

  There was one experience that Red dreamed about more than any other, however; more even than having her pussy licked by a handsome farm boy. Red desperately wanted to feel a man inside her. She wanted to experience the sensation of her pussy being stretched by a rigid shaft as it pushed slowly inside. She wanted to feel it consume her body entirely so that she’d be forced to cry out like all those women she had secretly observed. Poor Red desperately wanted to experience the joy in being fucked good and hard, but alas she was not married and nor was her father looking to find her a suitor for a good while yet – it was simply too useful for him to have an extra pair of hands around the farm – and so, for now, she just had to make do with the pleasure of her fingers and the occasional candle she would steal away when mother was not looking.

  Now, I must warn you not to feel too sorry for Little Red, as in all honesty she couldn’t always be described as being a ‘good girl’. You see, over time she had become something of a tease. It began quite by accident one Saturday evening when she was called down to the kitchen by her mother for her turn in the tub. Red loved bath night and once mother had disappeared up to her room she would light as many candles as she could lay her hands on, hang a freshly laundered nightshirt in front of the stove and pull off her clothes before sliding naked beneath the warm water.

  On this particular evening Red had been laying there, lazily dreaming of the ironmonger and how impressive his arm muscles looked as she’d watched him hammer out a new set of shoes for Snowflake, when she was startled out of her reverie by a sudden noise from outside. Her immediate reaction had been to fold her arms tight across her breasts so as to protect her modesty, but as she heard what sounded like an irritated whisper from beyond and beneath the kitchen window, she became aware of an all-too-familiar throbbing sensation between her thighs. Red shut her eyes and allowed her arms to slip back to her sides once more. She listened intently over her racing heartbeat, and again she heard the unmistakable sound of hushed male voices. Swallowing awkwardly through a constricted throat, Red called out – but only loud enough so that her peeping-Toms would be able to hear – ‘Yes, mother, but I just need to stand up and soap myself down,’ and on shaky legs she lifted herself upright.

  At first she faced away from the kitchen window, but she could see just enough of its reflection in the polished copper bottoms of the pots that hung from the stove. And soon enough the shape of two heads presented themselves, quickly joined by a third.

  Red was absolutely horrified that she was being spied upon – quite neglecting to acknowledge her own hypocrisy – yet as she proceeded to lather her breasts, discovering just how tight her nipples had now swollen, and the way they tingled as her fingertips played across them, she could not deny that there was something intensely thrilling about the experience.

  Slowly she began to turn around. Not wishing to scare her voyeurs away she made sure to avoid facing directly towards them, yet positioned herself in such a way that they would be able to see all that any red-blooded male could possibly desire. Red took great care over soaping her naked body, twisting first one way and then the other, her creamy-white flesh dripping wet and shiny in the warm glow of the candlelight, her nipples flushing an angry shade of scarlet from the heat of the water. She allowed a palm to slip down between her thighs, and she rubbed back and forth against the soft fur of her mound. Red gasped as a fingertip ran across the tiny bud of her clitoris, to discover just how it had swollen and how much it longed for caresses. She even considered sliding a finger inside, to seek illicit joy in the heat of her wetness, but just as she was wondering if she really dared there was an almighty crash from beyond the window. Instinctively she looked up with fright, just in time to catch the startled expressions of her brother, Josh, and two of his friends a moment before they ducked away to disappear into the night.

  Back in her bedroom Red was utterly incensed that her own flesh and blood could permit others to watch her as she bathed, but at the same time a tiny flame had been ignited, and once she’d climbed beneath the sheets she couldn’t help but allow her fingers to slide between her legs to play with her pussy until she arched her back and struggled to suppress the cries of her passion.

  Early the following morning Red sneaked into Josh’s room while he was out tending the goats, with the intention of placing a rotten egg beneath his bedclothes by way of revenge. Upon lifting his pillow away, however, she discovered a soft leather pouch containing a good ten pennies; way more money than Josh could ever have earned through honest labour alone, and she quickly realised that the enterprising little worm had been profiting through his sister’s bath time performances and she was quite set to explode with rage.

  She immediately stuffed the pouch into her pocket and strode purposefully from his room, but just then, upon reaching the top of the stairs, for some strange reason she stopped short. It certainly didn’t bother her that Josh would be in trouble beyond his wildest dreams should she complain to her parents, but it was more that she knew just what a puritan her father could be, and that once informed he would no doubt only then ban her from bathing in the kitchen where there were windows to be peered through.

  She considered confronting Josh directly and demanding the money for herself, but then there would be no more shows for her to put on, and if truth be known she had rather enjoyed it. So with her mind made up she counted out exactly half of the pennies and placed them in her pocket. She then returned to Josh’s room and replaced the pouch where she’d found it. Of course her brother would be incandescent with fury when he discovered half of his ill-gotten-gains were missing, but he would be in no position to protest, and being the young entrepreneur that he clearly was, he would no doubt only be encouraged to set about earning yet more.

  Neither Red nor Josh ever discussed their little business arrangement, but thereafter, every Sunday morning, Red would go to his room and help herself to half of the contents of his pouch; a sum which only grew with time and the notoriety of her displays.

  You might have thought that her bath night performances would have been enough to settle her appetite for male attention, but in time this proved not to be the case and she took to teasing the farm boys without any hope of financial reward. On summer afternoons she would choose one lucky young man, and let slip how sticky-hot she was and how she couldn’t wait to sneak off when father wasn’t watching to enjoy a refreshing dip in the creek. Once there Red would strip naked and dive into the cool water knowing her young voyeur would be hiding behind a tree while she frolicked in the water or sunned herself on the rocks.

  Once a year the travelling folk would come to the village for the horse fair, and in the hope of earning a little extra money they would move from farm to farm in search of casual labour. These men had a reputation for being fighters, drinkers and frequenters of whores, and most farmers would threaten to set the dogs on them if they so much as dared to step onto their land. But not so Red’s father as he knew them to be strong men and hard grafters, and on good years he would take on a dozen or so to help out in the fields.

  During the traveller’s most recent visit, Little Red had awarded herself the task of taking out their lunchtime refreshment, telling her mother that it was only fair that they be treated like any other farm worker, but secretly, she only did so because she enjoyed the attention they would bestow upon her, not to mention the pleasure she would gain from seeing them stripped down to the waist and glistening with the sweat of their toil.

  Most of the local girls were scared of the travellers as they looked quite different to the men of the village. Their hair was as black as pitch and they would grow it long and wear it tied back with fine ribbons. Their skin was the colour of cinnamon bark and many had strange symbols and patterns cut into their flesh. The old wives would say this proved them to be in league with the devil, but Red refused to listen to such scurrilous nonsense, and anyway, even if it was true it onl
y excited her further to chance her luck with such dangerous men.

  On one particularly hot day, Little Red went to the men damp with sweat and clutching a cloth-wrapped cheese and a newly baked loaf to her chest. The leader of the group, a particularly handsome man with sapphire-blue eyes, rippling chest muscles and brass rings in his ears, thanked her in an accent so thick Red thought he might have come from the moon, and went on to say that, as she looked in need of a drink, they would be honoured if she stayed for a while and shared a draft of their ale.

  Red had immediately thought to say, ‘Thank you, no,’ in the knowledge that her father disapproved highly of ladies who drank alcohol, but the beer looked ever so inviting, and as she watched one of the men pour it from a small oak barrel into enormous clay jugs, she found herself wetting her lips and offering an accidental, ‘Yes please, that would be very nice,’ instead.

  In words she could make no sense of the leader quickly instructed one of his comrades to bring over a mug, and being the thirsty girl that she was, she immediately knocked back an enormous draught, only to then cough and spit it out through the shock of such a bitter taste. This caused the travellers to hoot with laughter and Red, thoroughly shamed, had half a mind to run away. But with a kind smile the leader held up his hand and told the men not to be so rude to their guest, before explaining that she must not gulp down ale in the same way she might enjoy her milk. He then went on to teach her to take small sips and to hold the liquid against the back of her mouth rather than at the front, and soon enough Little Red was drinking down the beer as though she had done so for years.

  Before she reached the bottom her mug was refilled, and while they ate and drank together the men regaled Red with tales of their homeland. Red’s mug was filled a third time, and as one particularly jolly fellow danced a side-splittingly funny jig, she noticed just how wonderfully fuzzy and fluffy the world now appeared. She told the men all about their reputation within the village, and they just laughed and agreed that it was probably quite fair. But she didn’t think so at all; she thought them to be fine gentlemen for sharing their refreshments with her, and she gladly accepted another fill of the ale.