Ponygirl Tales

by Don Winslow

  At a crisp word of command the well-trained ponygirl alertly raised her head. She obligingly wiggled her tail to invite the master’s whip -- as she has been taught to do. A quick flick of the wrist sent the delicate strap whipping though the air to kiss Justine’s naked rump right across the plump curve of those narrow cheeks with a tiny whap that jolted the ponygirl into action.

  As she began to pull, the ponygirl happened to look up, and saw her Mistress watching. Their eyes met briefly. Lady Ursula saw those big brown eyes flashing that look of pride in the pretty face of the high-spirited ponygirl as the two of them started off on an easy jog. She saw the haughty toss Justine gave to her cropped pony tail as they turned away, and it was the impertinence of that departing toss of the pony tail that so enraged the watching woman.

  She stood watching the buggy turn start down the smooth gravel pathway, gradually picking up speed as the ponygirl broke into loping a trot. An observer would have noticed the scowl that creased her Ladyship’s noble brow, the tightening of her lips, the cruel smile as she watched the buggy recede.

  What thoughts might be going on behind that handsome brow an observer could only speculate, but as it happens an intriguing idea was beginning to form in the Lady’s mind. She realized that she would soon have an opportunity to attend to the matter of the prized filly in her own way, for the care and feeding of the ponygirls would be left entirely in her hands for three whole days. Lord Edgewater was about to make one of his rare business trips to the city. She would make the most of those three days, determined to humble the elegant, high-stepping beauty.

  Of course, his Lordship and his trotting pony were blissfully unaware of what was being planned on that balcony overlooking the courtyard. Had he known he would have certainly taken precautions to see that his consort’s wild enthusiasm was restrained in his absence. Basil tolerated Ursula’s perverse tastes, with amused tolerance. But he kept a wary eye on her sadistic streak, which he wouldn’t allow to go unchecked, at least not for very long, before he felt he had to take the Lady in hand. He knew how excited Ursula got once she had been given a free hand with one of the ponygirls. Her punishments were sometimes fiendishly ingenious, often bordering on the bizarre, but alas -- too often excessive. His Lordship, while recognizing the value of an occasional whip on the rump, or the satisfying smack a paddle to a well-placed bottom, just to keep a spirited ponygirl in line, disapproved of the more heavy-handed methods, the kind that could easily drive his cruel consort into an excited frenzy.

  But such thoughts were far from his mind as Lord Edgewater, from his vantage point, was treated to the cheery sight of his favorite filly, her caramel colored hair drawn back in that short-cropped pony tail bobbing in a perky bounce, as she jogged along, He was captivated by the liquid churning of those taut little cheeks of hers -- delightful cheeks that so neatly filled his greedy cupping hands. He smiled to see the way Justine’s juddering behind caused her newly-acquired tail to swish from side to side with spunky impudence.

  A shouted command, punctuated a with another crack of the slender whip, sent the running girl straining harder, forcing her even further over the bar she held before her, so as to acquire the faster pace her Master ordered. She broke into a loping trot. This was what Edgewater most admired: a well-trained young woman who held her head up and her upper body erect, straining shoulders pulled back, and arched chest proudly out in front. A talented girl could hold the demanding pose even while prancing; the sight of which never failed to generate a tingle of excitement in him. He especially enjoyed the way Justine’s hard naked body pulled against the restraining harness, the flex and pull of smooth leg muscles as the long-legged filly pounded down the beaten track.

  ***

  On Friday the news swept swiftly through the stable. The sight of the big silver Rolls pulling up to the front of the house, and left to idle there, its engine purring, while the uniformed chauffer took up his position to wait by the open door, was further evidence: the rumor was true – the Master was going off on one of his business trips. The sense of dread hung over the stable for all knew how much their cruel Mistress relished the chance to get her hands on the ponygirls. Justine watched and waited, her feelings a mixture of excitement and dread.And she didn’t have long to wait, for the car had not been gone an hour before the groom came for her. Her wrists were banded with wide leather cuffs, padded, and lined with silk to avoid chafing. Lady Ursula was careful to see that none of the girls would bear any marks of abuse which might come t o the attention of the Lord of the Manor once he returned. A leash was snapped to the high leather collar she wore. The ponygirl’s hands were then drawn back behind her, the cuffs clipped together, and she was led off to the exercise yard, walking tall, with head up and hands behind her back, wearing nothing but her sleek black boots.This would not be the first time her Ladyship had put Justine through her paces, for the beauty of the stable was often singled out for special treatment, sometimes in private, sometimes before the other girls, as when the imperious Mistress made the kneeling girl bend down to the ground to kiss a proffered boot while the others watched in awed silence. Lady Ursula got a wicked thrill from witnessing the abasement of the proud beauty, wildly elated to see the young beauty lowering her head in complete and total subservience to her Mistress’ iron will.But although she was shamelessly used while in the harness, she bore the mild discomforts well. It was the humiliating way that her mistress used her as her personal love slave that Justine most dreaded. For there were times when she was required to do service as a ponygirl during the day, and to provide services of a personal, more intimate kind at night -- in the Lady’s bedchamber.***The groom began to put her through her paces. The daily routine always started with 40 laps around the tall metal pole erected in the exact center of the exercise yard. The short leash was replaced by a long lead that hung loosely from her neck while the other end was attached to a freely-pivoting ring set near the top of the pole.The first lap began at a brisk walk. The groom set the pace, the girl taking wide strides in her high-heeled boots while her wrists remained tied behind her. At the second lap, the overseer ordered a prance. He called out his command and with a flick of the wrist slapped her straight across her tight-cheeked young bottom. Lifting her knees ever higher in the stylized manner of a show pony, Justine was dutifully making her rounds when the single word “Stop!” rang out. Instantly, she stood stock still. Keeping her gaze fixed forward, she was unable to see the figure coming up behind her, but the ominous crunch of booted feet stomping on the crushed gravel made it clear to her. She knew that tread! And the realization sent a shiver of fear through her. Lady Ursula was about to take charge! It was well known that Lady Ursula thoroughly enjoyed wielding the pony whip at the daily exercises, gleefully urging the prancing ponygirls to step lively with each crack of the lash, but today the fiendishly inventive sadist had something quite novel in mind for her husband’s favorite, for in watching the naked girl parade around, her attention had been drawn to Justine’s vulnerable, high-riding breasts.Now Ursula stepped right up to Justine. Both women were tall, and both wore high-heeled boots, but the full-figured woman in the riding outfit was a few inches taller than the slightly-built nude. Justine stood with eyes forward, not daring to look up, while Ursula looked down on the arched chest before her, pointedly studying the small, up-thrust breasts with their brash oversized nipples.The Lady wore short riding gloves and now, without a word, she raised both gloved hands and began to fondle the flattened mounds of those pancake breasts, laying splayed fingers on them, pressing them together, and palming the large puffy nipples that Justine sported.“Such pretty things,” she murmured, pressing the soft flesh of Justine’s thickened disks into slow circular motion. “Superb! Ah, but those unfortunate nipples of yours…far too large; quite excessive for such delicate treasures, don’t you think so George?” She flicked a nipple with the tip of her finger, while delivering this aside to the groom who stood there nodding with grinning enthusiasm. But Ursula ignored the m
an who stood fascinated to see the interplay between the two beautiful women. For Ursula, the groom did not exist; nothing existed but the two of them -- and the world which they were about to enter.“Look at me!” she hissed. And while she was looking deep into Justine’s big brown eyes she delicately plucked a prominent nipple between thumb and forefinger and gradually tightened her grip, all the while searching the girl’s eyes for the first glint of rising pain. She smiled to see it, as tears welled up and the girl sucked in a shivering breath of air through clenched teeth and jacked upward. Lady Ursula held on, pulled, testing its elasticity by stretching the little breast into a tightened peak, while her victim arched her back and clenched her jaws against the pain. It took only a bit of this rough tit play before Justine was breathing deeply, her tortured breasts throbbing, undulating in ragged heaves. The excited nipples now protruded, dark and swollen with arousal. “You see what I mean, George? All together too brazen! We can’t have her walking around with those big things sticking out like a sluttish whore’s! Such impudence!Here the lady paused to consider. “I think,” she teased, rolling the hardened bud between thumb and forefinger, “that these will have to punished for showing off like this.”She turned to her wide-grinning assistant, who obligingly held out a set of nipple clamps. These were spring clips with smooth blunted jaws designed to insure that the tender flesh was not cut, but instead constantly squeezed and thus subjected to a dull throbbing pain that would persist while the devilish clamps were in place, and for sometime after they were removed. And they would not be removed until the Mistress of Discipline deemed that it be so. Justine knew of girls who were made to the wear the hateful clips all day long and even in stable at night, where they were free to remove them, but did not dare to do so.Now she held the nipple clamps, squeezing one to demonstrate the opening of the little jaws for Justine to see. The pair were joined together with a short chain. Curiously, the length of light chain between the clamps had been threaded through a hard rubber dowel rod. Ursula plucked each breast and very precisely attached the clamps to Justine’s jutting nipples, while the girl fought to stand still, biting down on her curled lower lip with each twinge of hurt. The ache settled into a dull throb; she would learn to tolerate the pain. For a moment the little rod swung down between her captive breasts like some sort of bizarre necklace. Moving closer, Ursula gave her victim the sort of smile the cat reserves for the canary, and lifting up the dowel rod purred in a silky whisper: “Open wide.”The ponygirl obediently opened her mouth to accept the rubber bit that was jammed between her small white teeth.With the rubber rod distorting her mouth, she looked up at her Mistress, confusion in her wide alert eyes. Ursula smiled benevolently, placed two joined fingers under the girl’s chin and lifted it high, higher, till Justine stood with collared neck stretched upward, her head thrown well back. With her chin held high her breasts were pulled taut and uplifted, the pliant flesh stretched up and out. Her Ladyship declared this to be a distinct improvement in posture!She now confided to her silent assistant that she considered bouncy tits unseemly on a ponygirl (although quite obviously in Justine’s case, her taut, small mounded tits hardly merited such restraint). Nevertheless, this was the posture the unfortunate girl was forced to maintain as she was ordered back into her routine, once more around the familiar circuit.

  “Trot, Bitch!” The obedient ponygirl, her petite beasts stretched tight, her wrists held behind her back, broke into a trot. “Faster! Keep your chin up; head high! Now Prance! Prance!” THWACK! The sharp sting of the flickering whip punctuated the shouted command, biting into that pert rump.

  “Shake that skinny arse of yours, you saucy bitch. Show us just what a little whore you are!”

  The lines of distress that creased the ponygirl’s pretty face brought a low, throaty laugh from her tormentor. And in this manner the bizarre performance went on and on, the ponygirl high-stepping in endless circles, and for some mysterious reason, the prancing girl’s deep humiliation was now drowned in a surge of perverse pride.

  Ponygirl Tales Three

  Blaze at the Races

  Randi and Blaze sat side by side, both girls topless, gazing ahead into the dressing table mirror before them. Randi was a well-endowed blonde whose heavy breasts with their wide capped nipples hung rich and succulent. She wore her wavy hair in soft curls which she hoped made her look a little like Marilyn Monroe. She was eyeing her bullet-shaped tits with a vaguely critical eye. She’d always been proud of her breasts. She was the most developed girl in her high school; never had trouble getting boys. They called her “Jugs” Malone. But lately she worried that her pride and joys might be sagging just a bit too much, and wondered, not for the first time, about getting implants, just to firm them up. She knew Blaze’s opinion, so she didn’t ask. She was against it. Blaze said most men liked to see the bounce and sway of natural boobs on a dancer, not those phony plastic jobs. But Randi wasn’t so sure. She slipped a hand under her left tit, hefted the soft boob a bit, and quickly let it drop. She glanced over at her fellow dancer, watching Blaze’s reflected image in the frame of light bulbs as the lanky brunette watched herself tucking her plump little tits into the gauzy cradle of a flimsy bra while she rattled on about the guy she met between sets last Thursday.

  The guy’s name was Franco, and he said he worked for someone named David Spaulding. He said this Spaulding guy was some kind of big deal; a producer, Blaze thought. Anyway, he said Spaulding was throwing a party at his place on Long Island and he wanted some of the girls from “The Winner’s Circle” to come out to his place just to “help with the entertainment.” That was the way he put it. Of course, Blaze had pretty good idea what he meant by that.

  The guy looked kind of cute, but Blaze was suspicious. This could all be just a con to get in her pants; customers were always coming up to the dancers with deals of one kind or another, and all they really wanted was to be able to say they had fucked a “Winner’s” stripper. She was about to brush the guy off, when she remembered that she thought she heard something about this Spaulding guy. She now turned to her friend, who read all the show biz magazines, always on the lookout for that one big break, to ask her advice: Had she ever heard of David Spaulding?

  Blaze was taken aback by the enthusiastic reaction she got. Randi’s big blue eyes instantly brightened and she grinned from ear to ear, nodding vigorously, barely able to contain herself with glee. She furtively glanced around the room, but none of the other girls were paying attention. Then she leaned closer to Blaze.

  “Are you kiddin’?!!” She hissed. “DAVID SPAULDING! God, he’s just the biggest TV producer on the East coast. He’s one heavy hitter, Baby. You mean you never even heard of the guy?! Where’re you from again? Cincinnati? Spaulding was the brains behind all those sitcoms in the 80s. I read that with all those residuals he has more money than some countries! He has homes all over the place. I just saw a spread on his place on the Island…South Hampton, I think. It’s HUGE...I mean acres and acres all in one of those walled-in compound like the Kennedys got: a fantastic house, with servants and swimming pools, horses, tennis courts, guesthouses…the whole thing. If this guy Franco’s for real, this could be great!” She edged even closer, took Blaze’s hand and lowered her voice to a conspiratorial hush. Blaze caught a whiff of sweet perfume as her friend pressed closer till their faces were close together and a soft breast nudged into her arm. The scent mingled with other perfumes and girl-sweat and cigarette smoke to form the hazy atmosphere in the warm closeness of the crowded dressing room. Randi lowered her voice. “Now, Honey, tell Randi all about it. I want details, Babe. Everything!”

  ***

  Thus it began, and a few weeks later, Blaze, Randi, Kim, Flo, Debbie, and Silky, were happily ensconced in the back of a luxuriously appointed van making its way out of the mid-town traffic to a place of dreams, a place called the Hamptons – a place they had only heard about.

  The hired help were rushing about making final preparations for the big bash, but heads were tu
rned when six pretty showgirls in tight shorts and cropped tops, clambered out of the van, long legs flashing in the summer sun. Awestruck, the girls stood gaping like tourists, taking in the starkly modern home of smoothened cream-colored concrete, glass and steel with its sweeping curves and cantilevered decks that soared out over the rolling lawns. Their driver ushered them in through the back of the place through full-sized glass doors that slid open with the press of a button. They found themselves on the second floor of the luxurious mansion in what appeared to be a glass walled room suspended in space. Their sandaled feet were sinking into the thick ply carpet as they were drawn towards the fall wall of glass with its spectacular view of the grounds, the well-manicured gardens, and the lush countryside beyond.

  Franco was waiting for them. Amid the hustle and bustle of the uniformed household staff, he alone seemed totally relaxed, fit and tanned in black denim jeans and a half-opened satin shirt, he greeted them smiling broadly. His eyes lit up when he saw the girls stroll in, and he took his time pointedly looking the women over, opening admiring the leggy dancers in their brief outfits, obviously pleased with what he saw.

  He now explained why the strippers had been hired: they would be providing the entertainment for the party, but it would not be topless dancing they would be doing today. His boss had something else in mind. He beckoned the group to the far glass wall, and began pointing out things on the estate: the pools, the tennis courts, the racetrack, and the prominent white stables gleaming in the summer sun like a jewel set in a carpet of green.