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Ponygirl Tales

Don Winslow

  Table of Contents

  Title Page

  Author’s Note

  Blaze at the Races


  But Weekends Are Mine!


  The Mistress of Rosedale

  Secrets of Cheatem Manor

  French Postcards

  The Blue Butterfly

  The Little Red Dress

  The Pleasure Machine

  Ponygirl Tales

  by Don Winslow

  ISBN 13: 978-1-937831-02-8

  A Pink Flamingo Ebook Publication

  Copyright © 2011, All rights reserved

  With the exception of quotes used in reviews, no part of this book may be reproduced, stored in a retrieval system, or transmitted in any form, by any means, including mechanical, electronic, photocopying recording or otherwise without prior written permission of the publishers.

  For information contact:

  Pink Flamingo Publications

  P.O. Box 632 Richland, MI 49083


  Email Comments: [email protected]

  Author’s Note

  I once came across a lady writer whose fascinating stories once graced the internet. D. would bury herself in her work, writing furiously for several days before emerging to present her newly-completed story to her male companion for his comments. One day, in the grip of the muse, D found herself writing about a naked girl who is made to pull a wheeled cart. Her companion read the piece and looked at her.

  “D, he asked, “did you know you just wrote a ponygirl story?”

  “What’s a Pony-girl story?” she replied with perfect innocence.

  Every writer of erotic fiction should try at least once to do a ponygirl story or two. Here are a few of mine.

  Don Winslow, Copenhagen

  Ponygirls Tales OneHow to Turn on a PonygirlClaudine’s eyes flew wide open. Throwing back the covers, she bolted upright in the bed, and sat looking around her at the unfamiliar room, staring in wide-eyed confusion. Somewhat dazed, it took the girl a moment to realize: she was sitting in a strange bedroom -- completely naked! Her growing fears escalated wildly when she also realized that the room’s sole window was barred! The panic-stricken girl jumped out of bed, bounded to the small high window, clasped the iron bars, and hauled herself up on straining bare toes to try to see what she could. Across the wide courtyard stood the stables she remembered from when they drove up the night before (was it only the night before?). Then she looked down to see beneath her window an incredible sight!Only a few feet below her, one of the fabled ponygirls stood at the ready: a tall girl with a lean, whippet-like body, and tawny hair that had been gathered up into a long pony tail that hung down past her shoulders. The girl had already been collared, her neck banded with a wide strap of soft black leather; now she waited patiently between the traces that attached her to a delicately-made sulky. Claudine was struck by the way the young woman seemed to have accepted her fate -- stoically, it seemed to her, or at least with resigned indifference.Awe-struck, she studied the slightly-built solitary figure standing at rigid attention in the early morning mist. Claudine wondered what thoughts were going through the girl’s proudly-held head. Surely she felt the cold. Perhaps she was shivering a bit, for the morning sun had not yet broken through to warm the day and the girl was totally naked of course, except for the shiny boots she wore. Sleek and tightly fitted to her calves, with stacked high heels that were thick and serviceable. Yet there was no sign of discomfort on that set, expressionless face.The extended shafts of the light-weight buggy were attached at her hips, chained to the wide cincher belt that constricted her waist. Her arms were secured behind her, bound together above the elbows but with just enough slack left so that she could bring her gloved hands forward to clasp the crossbar that rested in front of her hips. The effect was to pull the shoulders back while forcing the thin chest out. Naked breasts, small and gently sloped, formed thickened disks that were prominently lifted in proud display; nipples small, but sturdy.As Claudine watched, a bearded overseer came out to complete the preparations for the ride. In one hand he held a tangle of straps – a set of reins and headgear. In the other was a long horsetail made of fine hair of the same russet color as the girl’s own hair.The naked girl kept her proud head held high and remained absolutely still as the man closed in on her. And she never flinched when he tossed the headgear over her head. A long strap lay over the top of her head to hang down on either side of her face, while another circled the head from front to back. This second strap crossed her brow forming a headband that imprisoned a soft fringe of reddish brown bangs. When pulled into place one could see that the headband was joined to the vertical pieces with metal rings that rested just in front of the ears. The head harness was then secured -- the two dangling straps, adjusted carefully and cinched snugly, before being buckled under the upraised chin.Next, he took the bridle in both hands and held it up in front of the girl’s forward-gazing eyes. When she saw what was being offered to her, she dutifully opened her mouth to accept the hard rubber bit between her teeth. The groom now set about attaching the reins to the bridle, and drawing the leather straps back over her slim shoulders to lay the leads in the sulky’s basket-woven seat. While she stood there motionless, the stable hand took his time, moving slowly and deliberately, methodical in his preparations, preparations that were all but complete save for one important detail.It was to the tail that he now turned his attentions. Stepping close to the perfectly still figure, he fingered the collar that banded her neck, grinned right in her face, and then brought his lips close to whisper something in her ear. The girl obediently leaned forward over the waist-high bar, her little breasts spilling forward to dangle freely while she thrust her rump back and deeply arched her back at the groom’s quiet words of command.Claudine was fascinated! She watched intently as the groom produced a tube of gel and used it to slowly grease the squat plug that would be used to hold the tail in place once it had been inserted up the girl’s bottom.Claudine saw the ponygirl anxiously shifting her weight, slightly widening her boot heels. The widened stance allowed Claudine to more clearly see the strap that ran from the front of the waist cincher to pass between the legs before being secured in place, pulled up and buckled to the back of the wide waist belt. This crotch strap, drawn tightly up the crack of the girl’s ass, was deeply embedded between her narrow buttocks, but it had a ring conveniently placed so that the groom was able to adjust it till the circular opening neatly ringed the puckered anus.Now the bearded man grinned and said something to the bent-over woman, who closed her eyes, tightened her grip on the bar, took a deep breath, and nodded, waiting tensely for what she knew was about to come. From behind the barred window, the girl saw the burly man place a flattened hand squarely on the proffered rump steadying the girl as he leaned closer while the other hand probed between the cowering cheeks. And Claudine sucked in a sharp intake of breath as, with a sudden jab, the hard rubber plug was driven right into the exposed anus! The bending girl jacked upright, her clenching bottom recoiling in a futile attempt to escape the abrupt penetration. The groom laughed to see the pony-tailed girl squirming like a skewered fish on the end of the impaling plug.She straightened with a girlish wiggle that shook her violated young bottom and its new-acquired tail, as though trying to dispel the unwanted intruder. Of course, this was simply an instinctive reaction, one which she had to quickly suppress -- for the girl well knew that to expel a tail would bring swift punishment. The groom waited patiently till she had calmed down, said something to her, and gave her still-twitching rump a reassuring pat. Then his charge was made to snap to attention, once more assuming the proud carriage of a well-trained ponygirl at the ready: standing tall, bridled head he
ld high, pert breasts thrust out, booted legs pressed tightly together, clasping the crossbar with both gloved hands. The luxurious tail she had been given now hung straight down from her tight-cheeked buttocks, its dark reddish sheen nicely mirroring the girl’s own shimmering mane.The ponygirl was now ready, but one final inspection had yet to be carried out. The overseer slowly circled his charge, eyeing her up from the leather head harness confining that soft shiny helmet of russet hair to the pointed tips of her gleaming black boots, tracing the sleek and smooth curves of that lean, hard-muscled body with light, dry caresses.Of course the man couldn’t resist those nicely-presented breasts; pretty breasts that drew the hand, simply begging to be caressed. He allowed himself to pause to sample a floppy tit fingering the silky smoothness of that softly yielding tittie-flesh. His playful dalliance drew a quiver from the healthy young filly, who shifted uneasily from booted foot to booted foot. The watching girl felt an answering twinge of lust rise up in her own loins; her thighs spasmed in a throb of involuntary reaction to seeing the young woman squirming in rising heat as she was felt up, her vulnerable breasts fondled so shamelessly.But the purposeful groom allowed himself only a few minutes of this pleasing diversion. After all, he had a job to do. And so now he went about tugging on the harness, slipping a finger under the straps of buttery leather so as to assure a fit free from slack. With admirable self-discipline, the well-trained ponygirl never moved a muscle even as the big man’s slow hands roamed freely, enjoying her naked body. She remained rigidly still, straight booted legs together, chin raised, eyes locked on some distant horizon. The burly man passed a hand over those pulled-back shoulders and ran it down her gently tapering flanks to clasp a solid hip. A single finger slid under the cincher belt, circled around the girlish waist, pressing against the belt to test the tightness of the fit.Now the man stepped behind her, and spent some time lingering there, feeling his way along haunches and hindquarters with both hands, and murmuring to her all the while he enjoyed the feel of her naked body under his hands. Claudine watched as he lifted the heavy tail, and reached down to fiddle with the strap that ran between the thighs. Immediately the girl’s head snapped back, eyes flying wide open, as a ripple of excitement shot through her shoulders. Simultaneously, a muted buzzing sound broke the still morning air of the gravel courtyard. Claudine could dimly hear the whirling noise through slightly opened bedroom window. The muffled sound was coming from the girl, from something pulsing deep inside her!Claudine could only wonder what sort of the devilish device might be have been inserted between those tightly-pressed thighs, secured in place by the crotch strap, and left lodged there, deep inside the slender girl’s vagina. Or perhaps the muted humming came from the vibrating butt plug that had been so rudely shoved up her tight little buttocks so it might hold the tail between those sleek clamping cheeks.Her bizarre situation seemed a matter of complete indifference to the dutiful manservant who now turned his back on his charge, leaving the booted ponygirl humming merrily away as she waited in the traces in the cool morning air, while he went back inside to inform his master that the preparations were complete, and all was now ready for the morning ride.

  Ponygirl Tales Two

  Justine’s Pride

  Justine, not her real name of course, but the name she had been given, was her Lordship’s favorite…and she knew it. Lord Basil Edgewater instinctively knew when he first laid eyes on the girl, instantly appraising that lean, hard-muscled body, those streamlined haunches and those long leggy strides, here was a born thoroughbred! Whenever the stable was taken to compete at the races, she was the one who could be counted on to bring home the Blue Ribbon. She quickly became his prized filly – the ponygirl to beat. When exhibitions were held at the estate, Justine was the one Lord Edgewater inevitably singled out for a dazzling solo performance.

  She knew how much he enjoyed showing her off; displaying her proud mien, her aristocratic carriage and that high-stepping prance that never failed to garner applause from her Lordship’s guests, those enthusiastic connoisseurs who held engraved and highly-prized invitations to those very exclusive weekend events. The very thought of such solo performances before an appreciative audience made the girl flush, preening with pride.

  But pride can be a dangerous two-edged sword. And never more so than when that pride is coupled with the sort of beauty that is bound to incite the envy of other women. And if among those other women there is one who is strong-willed, equally proud, and equally beautiful, and if that woman holds high authority, then such pride should best be hidden, lest it become very dangerous indeed. And such a woman was the haughty Lady Ursula, the coldly remote mistress of Edgewater Manor.

  The lady shared her husband’s passion for that peculiar, some might even say bizarre, hobby in which he indulged. But while she enthusiastically joined him in what they had taken to call “our thing,” her manner and methods different sharply from her more tolerant and amiable mate. The tall, well-built, black-haired woman never showed the least affection towards the occupants of the stable. On the contrary, her dark eyes flashed, and her stern face tightened into a hardened scowl whenever she entered the stables, sending a shiver of fear through the huddled girls. Chiding her mate for being too easy-going, she would grimly take upon herself the role of disciplinarian, supervising the grooms and overseeing the rigorous training of the ponygirls; insisting that they measure up to her most demanding standards.

  This raven haired beauty, in her white silken blouse and cream-colored jodhpurs, thoroughly relished the role of overseer. It turned her on; filled her with creamy elation to have a girl with hands clasped behind her back, kneeling naked at her feet, while the imperious Mistress looked down on that upturned face, and watched the fear growing in a young woman’s eyes as she slapped a menacing riding crop, in a slow measured beat against the side of her booted calve.

  It was the Lady who taught the girls the three classic positions. “Down,” she would command in that clipped, no-nonsense manner of hers, and woe to the girl who didn’t instantly fall to her knees. On her knees, she might be ordered to service Master or Mistress. “Forward” would bring the kneeling girl onto hands and knees there to wait on all fours for further commands. Sometimes she would be forced to wait in that humiliating pose for what seemed an intolerable period of time, while her Mistress attended to other duties. On other occasions the naked girl would be ordered to follow her Mistress, crawling around the stable, the grassy courtyard, or the thickly-carpeted floors of the Manor House for the amusement of her owners, and their privileged guests.The “Present” command would have the girl, still on all fours, falling forward to her elbows where she was made to assume an even more subservient position: braced on extended forearms, her head lowered and back arched so as to upraise her tempting bottom in the most provocative display. Thus she might be made to present a tight young ass for any pleasures Master or Mistress may chose to indulge in, or perhaps for an honored guest who might wish to mount her. The submissive pose was also ideal for discipline, the girl’s upraised bottom presenting a prominent target for the flicking pony whip, or the plaint blade of the short-handled paddle. Or perhaps a girl would be made to assume and hold the seductive pose simply for the amusement of the jaded partygoers at one of her Lordship’s soirees. It didn’t matter to what use she would be put. The well-trained ponygirl was taught to submit; to obey instantly, and without question.

  Perhaps it was inevitable that the sadistic mistress of discipline and the proud caramel-haired beauty with the perky pony tail should find themselves on a collision course. Lady Ursula sensed that Justine was clearly a leader among the girls of the stable, who regarded her with a mixture of envy and admiration. She was older than the others, and having come to ponygirl training after a starting a promising career as a well-respected civil attorney. The young woman was intelligent, well-educated, pert and really quite pretty, as the mistress clearly observed whenever she saw her husband’s eager eyes light up at the appearance of his favorite with wrist
s tied behind her, being led out by a sturdy groom who loosely held the leash attached to the girl’s collar.

  Lady Ursula would stand with hands on hips, watching from the balcony overlooking the gravel courtyard, as her husband, looking trim and handsome in riding clothes, personally supervised the preparations for his morning ride. She saw how he never passed up the opportunity to check the harness, freely touching the perfectly-still girl’s naked body, feeling his way along Justine’s narrow flanks, pausing to finger the thick cap of a prominent nipple, to lavishly fondle those small, proudly out-thrust breasts. He spent some time at her hindquarters, filling his hands with her slim but nicely-rounded buttocks; he savored her firm young body as all the while the girl stood at rigid attention, booted legs held tightly together, head held high, shoulders back and thin chest out – in that classic ponygirl’s “ready” position. The Mistress of the Manor smirked to herself as she saw the girl respond to a soft-spoken command to widen her stance, obediently shifting her booted feet so that her Master could test the fit of the strap which, attached to the waist cincher from front to back, ran high up between her legs through the place where his hands now followed. Only when he pronounced himself satisfied with the trappings would he release her to allow the groom to back the ponygirl into place between the extended shafts of the delicately-framed buggy.

  Final preparations were now made. Her arms brought behind her to be tied together just above the elbows, enough slack left so that she could reach forward with gloved hands to grasp the horizontal bar which crossed in front of her. Once between the traces, the head harness was placed over that mop of caramel colored hair, the chin strap pulled tight and buckled. The hard rubber bit was then inserted between the teeth; the reins attached. And the ponygirl was ready – except for the final bit of adornment.

  The long pony tail with its squat butt plug was now attached by the careful groom who held Justine’s hard cheeks apart with one spread-open hand while he inserted the tapering, well-greased end of the butt plug into the girl’s spasming anus. He had her shake her new tail to be sure it was securely in place; once satisfied, he turned to help his master take his seat in the buggy, finally handing him the light pony whip.