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Author's Note: As is often the case with my stories, this one explores themes of non-consensuality and is therefore dark in tone. Please don't read it if that will offend you. If you do read it, thank you and I'd be grateful for any comments you may have.
Part 1
He'd been a naughty girl.
At least that's the judgement Miss Victoria had made and in this awful place, only her assessment and those of Miss Francesca, her elder sister, and Mistress Anna, her mother, counted. It hadn't even been deliberate; Miles had been here too long to dare to be disobedient or misbehave on purpose. He knew where that road led and had no desire to explore the route further than he already had before he'd come to learn better. If Miss Victoria said he'd been a naughty girl that is what he'd been. There was nothing he could do or say to influence the decision so consequently he'd been sent to bed early which was where he was now, looking forward to what he fully expected would be a thoroughly uncomfortable night.
It had happened during his afternoon play session. His heart had sunk when Miss Victoria had announced she'd be overseeing it as she was his least favourite of his captors. Mistress Anna had been overseeing his ballet practice with a sharp eye and a swift crop. It was something they insisted on as Mistress Anna claimed it helped make his movements more graceful. He'd been dressed in his pink leotard, tutu ballet shoes and white white opaque tights and was struggling to master the called-for positions and movements when Miss Victoria had made the announcement. She'd changed him back into his clothes; the new dress they'd put him in that morning; a thin blue gingham affair with a lace-trimmed peter pan collar, short sleeves and a frilled hem that fell to his mid thigh and thrust his cardigan, the white one with the flow buttons at him and told him he could play outside as the sun was out. His only other clothing had been a pair of white knee socks and cotton panties so he was thankful for the cardigan as he knew that, although the sun was indeed shining, it was still early spring and as yet there was little warmth in it. Then she'd given him Jilly, the doll he was expected to carry everywhere, and led him towards the porch and the garden at the rear of the house.
As he'd dutifully followed Miss Victoria to the back door he'd dared let his eyes stray from their proper place, gazing at the floor, to examine his captor from the back. She had a mass of unruly, frizzy hair, flame red in colour and held back into a rough pony tail which had bounced across the back of her sweater as she walked. Her complexion was the classic freckled milky white which went with such hair and he knew from experience she possessed the archetypal redhead temper too which, combined, with a vindictive and somewhat sadistic streak, made her unpredictable and difficult to please or placate. He judged her, from the youthful texture of her skin and her conversation regarding her educational endeavours and peers, to be around 17; about three years younger than himself; another factor which increased the humiliation he felt when she was in charge of him. Inevitably, his eyes had fallen to her arse which, in the tight jeans she was wearing was outlined perfectly. If he was honest, it wasn't that great; Miss Victoria couldn't quite be called 'chubby' but she had something of a curvy figure and correspondingly thick thighs. Ordinarily, Miles wouldn't have looked twice at her, but he'd had no release of any sort and hadn't been allowed or even able to touch or even see his penis in almost eight months, so all it took was the briefest glance before he felt his groin start to stir and, almost immediately, the start of the painful pressure exerted by its tight prison in such circumstances. Hurriedly he returned his eyes to the floor and desperately tried to think of something that would stop the incipient tumescence. If he didn't he knew she would spot his discomfort and draw the obvious conclusions and he wouldn't like that at all. So he concentrated on thinking about his ballet lesson and wondered if his captors were subtle enough that his long denial was designed to force him to dwell upon such things and aid in his own degradation. He wasn't sure, but his experience of them made it quite possible.
Outside, it had been chilly as Miles had expected and he'd been forced to wait for several minutes as Miss Victoria dealt with a call on her phone. He arranged Jilly on the garden bench, as though she were surveying proceedings. It was one of the crushingly humiliating behaviours he had learned over the months to keep his ever-watchful captors happy with his compliance. As he bent forward to fuss with dolly's old-fashioned Edwardian costume he could feel the chill fingers of the breeze caressing his thin hairless legs under his skirt and fluttering the ribbons and his bunches across his face and into his eyes. He had just been starting to shiver when Miss Victoria had looked up and impatiently told him to skip around the garden. He had complied happily, keen to generate some warmth, and spent several minutes skipping around, hair and skirts fluttering, always aware of her contemptuous eyes on him as she spoke into her phone.
He had hoped this would be the extent of his playtime; him simply skipping around to keep warm and Miss Victoria too pre-occupied with whatever teen drama her phone call concerned to pay more than cursory attention to him, but it was not to be. Laughing and chatting into her phone she had disappeared into the shed and returned holding a skipping rope. Finishing her call, she had beckoned him over and handed him the rope, telling him he needed to practice. Obediently, he began skipping, bouncing up and down, practicing the complicated games and rhythms his captors demanded he learn, and his heart sank as he watched Miss Victoria, begin to stalk around him for he knew what was coming when she took on that look. Miss Victoria was unlike her mother and sister. Miss Francesca and Mistress Anna were quite matter-of-fact in the way they treated him. Yes, they were draconian and had debased, degraded and violated him physically and mentally. They'd never explained their reasons or their purpose, or even their objective to him, expecting him to learn quickly by trial and error, but they were at least consistent; they always treated him as the pre-pubescent girl they obviously expected him to emulate. They hardly ever even hinted at, let alone acknowledged his previous existence and were detached and almost professional in their approach to his torment. Miss Victoria was different. She seemed to revel in his humiliation and knew which buttons to press to exacerbate and heighten it.
Concentrating on the looping rope Miles tried to ignore her, but he could feel her eyes examining him from the shiny black mary janes on his feet to the neatly bunched hair on his head. He could picture the familiar slightly curled lip and the contemptuous green eyes, even though his own were firmly fixed on Jilly's bland, painted face a few metres away. It wasn't long before she began taunting him, starting with how pretty his new dress was and then making him sing out the chants that went with the skipping games he was practicing, knowing how the high, trilling, little-girl voice they'd given him sickened him to core. He couldn't help himself. He knew well enough that he shouldn't show the humiliation he felt or his impotent anger at all they'd done to him, but something must have shown on his face, some hardening of his lips or narrowing of the eyes, because she had struck like a snake. Abruptly she'd made him stop skipping had stepped forward and raised his skirts, making him hold them up as she examined what lay beneath. She'd gasped in mock delight, even holding a hand to her mouth and exclaimed how cute his panties were, stepping around him to examine them from all angles. They'd been pretty typical of the sort of thing he'd worn almost every day he'd been here; pink cotton with a dainty white picot trim around the waist and leg holes, a matching bow at the front and a dusting of tiny flowers printed on the fabric. She'd cooed particularly over the motif of Princess Belle on the front looking coyly out while clutching a rose in her canary yellow ball gown. She knew how much he liked Belle she'd said and remembered his birthday party the previous month when he'd had a Belle cake and looked so pretty in his Belle costume. He'd felt his face flaming despite the chill air and tears forming in his eyes, as she'd continued moving closer to fuss with the panties. She'd pulled them up tightly by the waistband then leaned close, her arms around him, a cool finger sliding under the leg band at the back, hooking it from between his buttocks where it had ridden up during his skipping. He was acutely conscious of her breasts pressed into his chest and she knew it, lingering longer than was necessary and gazing into his tear-filled eyes with a knowing sneer. He could remember stifling a sob and then she had stepped away looking down at the flat crotch of the panties and laughing cruelly, shaking her head and reminding herself not to be silly; that he wasn't a macho, virile, twenty year old college man who could show a girl a good time, but a little 8 year old girl.
He so wanted to punch her then to throw her to floor and beat her until she begged for mercy, but he knew he couldn't. He'd tried it the first time he'd been allowed into the garden, thinking he could make a run for it and escape, but she'd simply laughed, caught his arm and before he knew it he'd been face down in the grass immobilized, with her kneeling on his back twisting his arm. She had made it seem so easy. He had known he'd been weak, having spent almost two months in bed, much of it sedated, while his surgeries had healed and his muscles had atrophied. They'd kept him that way two when they'd finally got him up and began his programme of age regression and feminization, feeding him a barely adequate diet and, he suspected something more in his food, or the medicine he took every evening and morning. But Miss Victoria had also handled him with practiced ease and he could only conclude she had training of some sort. He'd tried something similar once more with Mistress Anna with the same results and, after the punishments that resulted he had given up, realising the three women could subdu him physically almost as easily as an actual child. Of course he'd vowed to bide his time. To watch and wait for a chance of gaining the upper hand when they were least expecting it and then: boy, would revenge be sweet! But the weeks and months had rolled by and the relentless cycle of degrading treatment, reward and punishment had continued, eroding his will, steering him into tacit co-operation as the least painful course. He even abandoned his ever-more elaborate revenge fantasies in the face of a continuing complete lack of opportunity and the punishing effect they had on his tightly imprisoned penis.
And so Miss Victoria had cowed him yet again, a 17 year old girl effortlessly mastering an adult male three years her senior. She had resumed her vigil indicating he should continue skipping so, shame still burning on his face he had begun twirling the rope again as she tut-tutted and told him that little girls like him shouldn't flash their panties. And that was when it happened. He had little stamina at the best of times and his exertions so far had drained him. This, and Miss Victoria's attack had made him tremble and his legs feel like jelly which made it harder to keep his timing or his concentration so, inevitably, he made a mistake and the rope caught his ankle. He stumbled several yards forward his foot coming down hard which was when the slick leather soles of his mary janes betrayed him and he skidded, lost his footing and had sat, hard, in the middle of a large muddy puddle. There had been a moment of shocked silence until Miles disbelief quickly gave way to fear as he realized that, not only were his clothes soaked in cold, wet liquid mud, but that a small tidal wave of the same stuff had engulfed Miss Victoria, drenching the Ugg boots she wore and spattering her jeans past the knees.
Her reaction was swift and she pounced on him, grabbing one ear and pulling him to his feet, grinding the little daisy earrings he wore in his pierced ears painfully into his flesh. Then she'd pulled him towards the house, holding him by the ear with his head at the level of her waist, his arms and legs flailing as he struggled to keep his balance. All the while she had shrieked at him furiously about what a naughty little girl he was, how she knew he'd soaked her deliberately and how he was going to be sorry.
By the time she pulled him into the back porch of the house Miles had been crying, both from the pain of feeling like his ear was being torn from the side of his head and his utter helplessness. A few short months before he had been a happy, well-adjusted male with good prospects for his future, keen to take on the challenges and opportunities of life. Now a sadistic teenager was able to treat him like her little sister. The dissonance between the two pictures had a constant, almost physical impact and every time the power of his captors was demonstrated and he was forced into some new compliance, a little more of the bright young man he had been shrivelled inside him. He had nothing left physically or mentally to resist as Miss Victoria sat on the bench that was kept in the porch and virtually yanked him across her mud-spattered knees. A small part of him had at least been grateful she had released his ear which felt like it was on fire as she had pulled the skirt of his dress up across his back. Unceremoniously, she had wrenched his panties down by the waistband and off his legs, shaking them angrily in front of his face as she'd scolded him over their muddy state, before dropping them to the floor below him.
The the first blow landed on his now-exposed buttocks and he yelped pathetically, the stinging slap enhanced by their wetness and the cold. Two more followed in rapid succession as Miss Victoria continued to rant. Miles writhed on her lap hating himself for beginning to apologise and grovel abjectly in his thin high voice. But she had not relented and he'd been helpless, she'd even grabbed and held both his wrists pinioned in the small of his back when they'd tried to protect his rear. All he'd been able to do, as so often before, was try to endure the punishment, squeaking and bucking involuntarily as the blows rained down, his face fixed firmly on the ground where even the normally anodyne features of Princess Belle seemed to be laughing at him from the mud-soiled panties bunched on the floor.