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Authors: Don Winslow

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BOOK: Ponygirl Tales
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He grabbed two greedy handfuls and fondled the bending girl lavishly. If having her breasts felt up excited her, you’d never know it, for the well-disciplined girl held the pose without moving a muscle. The groom looked over his shoulder to see that his boss was busy in conversation, and thus emboldened he decided to try for one more bit of fun by sliding a hand down her body to grab an ass cheek, and giving the red girl and affectionate squeeze in a furtive caress that caused her to squirm and wiggle her shoulders. He glanced up to see Kimar looking his way, and quickly gave up his pleasant dalliance to return to work, tugging on the harness, slipping a finger under the straps of buttery leather so as to assure a fit free from slack.

  Now we saw the true purpose of the strap that hung from the belt as the groom reached between her legs to take up the strap and pull it through her opened thighs. He drew the strap up between her cheeks and held it taut in her crack while he threaded the end through the slip buckle.

The crotch strap was now deeply embedded between the buttocks, and I noticed that a small metal ring had been set into the strap. This grommet was placed so that, with a bit of adjustment, it ringed the puckered anus. The metal grommet would secure the notched plug, keeping it firmly in place up a girl’s ass, throughout even the most strenuous exercise.

The groom left that perfectly-poised ass for just a moment while he coated the little wooden plug with axle grease. Then the stocky fellow man planted a beefy hand squarely on Big Red’s rump, while the other held the greased plug which he processed to screw up the big girl’s churning bottom. Red I wriggled, arched her back, and jacked upright. Her clenching bottom vigorously squirmed, shaking her newly-acquired tail.

The groom waited for her to settle down before stepping back to call the red team to attention. The three slaves straightened up to assume the proud carriage of well-trained ponygirls at the ready: standing tall, bridled heads held high, breasts thrust out, legs pressed tightly together, clasping the crossbar with both hands. Three bright red tails hung straight down from three tight-cheeked young buttocks.

Once the blue team was similarly prepared and in place, the drivers made their appearance. These were even younger girls; slightly built, light-weight girls being most prized to be trained as jockeys. They were, of course, naked; their necks were banded with the 4-inch high slave collar. Each was equipped with a thin whippy rod, which, Lucius assured me, they were not reluctant to use. The teams were now lined up, ready for the start of the race.

At an indifferent wave from the preening procurer, a flicking snap of two light whips stung girlish buttocks, and the ponygirls were off to the roar of delight sent up be the enthusiastic crowd.

They began with the ritual of circling the oval at a canter: the two teams in step, side by side. Trained to show off at such performance, they pranced with the sort of classical, high-stepping precision that was much admired among the connoisseurs of such matters: knees raised high, heads thrown back, chin held high, breasts jiggling as they trotted once around the track. After one lap was completed, with the sustained applause of the racing enthusiasts still ringing in their ears, someone banged a drum, and the race was on.

Now the ponygirls broke into a gallop, straining against the bar, sleek muscled legs pistoning furiously, knees pumping high, and bare feet pounding the hardened earth in syncopated rhythm. We watched the well-oiled teams sprint by, eyeing up the bouncy, juddering breasts, and as they passed in front of us, being treated to the sight of six pairs of churning buttocks, adorned with tails that were swishing, in time with the jogging rhythm of the running girls, as they retreated down the track. I kept my eye on Big Red, straining mightily, her head back, chest thrust out. Her long-legged stride set the pace, so that her teammates were forced to work even harder to match her, stride for stride.

As they entered the home stretch, the little jockeys began wielding their stinging whips with renewed determination, vigorously slashing at the churning buttocks, while the excited crowd urged on their favorites.

At the end, it was virtually a dead heat, although the red team managed to edge out the blue at the last second. The crowd went wild, and cheers rang out, as the chariots continued circling at a slower pace while the sweating, panting ponygirls struggled for breath, breasts heaving mightily, as they slowed to an easy trot.

Watching the magnificent red leader panting heavily, her long body quivering from the workout, her high-mounded breasts heaving in slowing undulations, I had to reach down to adjust my tunic to ease my stiffened penis. I knew what I had to do!

I jumped up, pushing my way through the excited crowd to find Kimar. I pulled him aside for a few quick words in an oversized ear. I assured the wily trader that, while he was entitled to a detachment of troops to protect the caravan for the normal 100 leagues from our post, I could personally see to it that he got the very best protection the Roman army could offer. He looked at me suspiciously; narrowed eyes taking on a slightly puzzled look. But all he needed was a troop of well-armed soldiers, he countered. Slow on the uptake, I thought. True, I acknowledged, but, I pointed out to him, we had both young, green recruits normally sent on such duties, as well as battle-tested, seasoned veterans. The later were the kind of stout men who would not turn and run at the first shouts of a thundering horde, leaving a defenseless caravan to the mercies of the wild Germans. And our local Germans
were
an unpredictable lot. They had been acting up lately. With such a valuable cargo as his…well, one just never knew…

At last, the crafty slave trader saw the light. A sly smile curled his bloodless lips, followed rapidly by a dark scowl. ‘And the cost of this
extra
service?’ he wanted to know.
That
was the question I was a waiting for!

That night, a splendid Nordic beauty was delivered to my quarters. No longer Big Red, she had been rubbed down after the races, bathed and scented, the red dye gone from her statuesque body. And now she knelt before me with eyes downcast, hands behind her back, the golden hair on her bowed head shimmering in the flickering torchlight.

While she was no longer a ponygirl, she presented herself as I had specified: in harness. I wanted for myself the pleasure of relieving her of her bright red tail as she waited on hands and knees for me to mount up. I still have it, nailed up on the wall of my quarters -- a piece of tail from a most unforgettable night.

Ponygirls Five
It Is Required
               One of Lady Ursula’s more perverse demands was to see to it that each of the stable’s ponygirls was individually fitted with a personal vibrator, a smooth plastic rod which a ponygirl might be made to wear at the whim of her mistress. And the Lady found it most amusing for a ponygirl to be equipped with such a device when the girl was being put through her paces in the exercise yard. A crotch belt, attached to the front of a waist-cincher, was buckled tightly between her legs. Like some sort of a chastity belt, it would secure the sex toy in the vagina, assuring the humming intruder could not be expelled, even during the most strenuous workout.
Today, it was Justine’s turn to be “properly-equipped.”  Now the pony-tailed girl stood at attention, slim legs set together, pert breasts uplifted and jutting forward while the straps of the leather harness were tightened in place about her slender body. The groom began the preparations by fitting the body harness, but it was her Ladyship who insisted on personally seeing to the details of the intimate violation that was about to take place.
In preparation for the humiliation she was about to suffer at the hands of her wicked mistress, Justine was led to the thickly padded trestle conveniently kept in the barn for just this purpose. Ordered into position bending down over the padded bar, the obedient girl reached down to clasp the iron staples which served as handholds on the far side of the splayed legs, while obligingly spreading her booted feet. With head inverted and pony-tail dangling down, she closed her eyes, took a deep breath…and waited.
The face of the mistress of discipline was a mask; tight and expressionless, yet her eyes were shining with the fiendish delight she always found in this particular task, as she approached the bending girl. She slowly ran a gloved hand over the jutting curves of that conveniently-placed buttocks, patted the offered rump thoughtfully. A single finger slipped into the crack, causing the cheeks to clench instinctively. The gloved intruder followed the curve to the place where it might blindly feel its way into crotch and the hidden pouch of Justine’s lightly-furred vulva. The bending girl eyes flew open; electrified by the first intimate touch of those gloved fingers probing her sex. Then the fingers were stretching her cunt, holding the labia splayed open while the smooth rod was introduced.
For her Ladyship, this was one of those supreme, an unutterable moments: to steadily shove a sturdy vibrator into a girl’s vulnerable cunt was pure ecstasy. She swallowed down the knot of lust that rose in her throat. Unable to resist the urge to fuck the girl with the shaft, she pumped her wrist, just a little, till she had the ponygirl bounding up on her toes and wiggling with excitement. As she diddled the girl, Lady Ursula grinned at the fascinated groom who stood on the sidelines watching in silence.
After the rod was worked well in, she gave it a final push that drove the impaled girl up on her toes. Justine jacked straight up, head and shoulders arching back, twisting, yet struggling to maintain the mandated position, as the grinning woman screwed the shaft all the way in. Save for the rounded cap on the end, the entire length had been swallowed up the ponygirl’s distended vagina.
A twist of the protruding cap activated the little sex toy, sending a thousand tingles of pleasure electrifying the healthy young body of the tense ponygirl. Justine closed her eyes and swallowed down the surge of pleasure while the vibrator hummed merrily away, tickling her innards with vibrating ripples. Justine wiggled her little rump, unable to keep still.
The Lady ignored her sudden agitation, reaching under for the strap that dangled between the girl’s legs -- the strap that hung down from the front of the waist-cincher. Drawing it up into the bending girl’s crotch and running it through the slip buckle at the back of the sturdy belt, she was able to cinch it up, tightening it in place. She tugged on the strap, getting a whimper from her bent-over victim. Another even more determined tug had the spirited filly biting down on the hard rubber bit jammed between her teeth, her jaws tightly clenched. Lady Ursula assured herself the straps that bound Justine’s body were tight, well-fitting -- and just a little too tight to be comfortable.
Once satisfied with the arrangements, she was pleased to leave Justine with the buzzing device buried up her cunt while the restraining strap cut into the soft flesh of her most intimate parts.
Justine was now subjected to repeated thrills of unbearable pleasure that curled her toes, along with the more deeply satisfying feel of the buttery leather crotch strap cradling her vaginal pouch, drawn tight as it was, pressing into the softly yielding bulge. The intense stimulation had her twitching and shifting uneasily from foot to foot.
Only when she was satisfied that the vibrator had been properly installed, did her Ladyship call for the tail, which the attending groom now brought forth. Normally, Justine submitted to the hateful act with equanimity when it was one of the grooms who inserted the butt end in her anus. But she intensely disliked having her Ladyship do the deed. She knew the sadistic woman took evil delight in inflicting a bit of pain whenever she carried out her preparation “duties.”
Lady Ursula rudely grabbed Justine’s buttocks, pried her open, and abruptly rammed the greased butt plug home. Justine recoiled at the stab of pain in her rear-end. But the cruel mistress of discipline was not satisfied with the connection. While Justine’s eyes widened in growing alarm, she continued to push till the dilated anus was truly violated, determined to force the little rear gate to accept the widened end of the plug. A final poke sent the butt plug all the way into the girl’s tight-cheeked young bottom! The little ring of muscle snapped shut over the wide end, clenched tightly, leaving nothing but the lanky length of fine hair hanging out her butt.

Justine was a proud girl, and she truly hated this enforced humiliation, but she knew that this indignity too, must be endured. She had once overheard her mistress talking with Lord Basil about the Lady’s peculiar proclivities. He questioned the usefulness of the vibrators; expressed his doubts as to whether they served any useful purpose. But his imperious consort curtly informed him, in that clipped tone of hers, that that was hardly the point. A well-trained girl had to learn that such things must be tolerated. Such discipline had a salutary effect on a ponygirl’s character. “It is required,” the Lady concluded in crisp words that ended all further discussion.

Such were the indignities inflicted on the young and pretty ponygirl at the whim of her depraved mistress. Of course, Justine submitted to each one, as she had been taught to do; aside from the occasional grunt, or moan, she suffered these humiliations in silence. A ponygirl was permitted to speak only when spoken to.

“It is required!” was the consolation she sought, the touchstone she came back to again and again. A familiar mantra played over and over again inside her head whenever the throb of some devilish device lodged in her body began to intrude into her awareness. It is required! It is required! It is required!

Ponygirls Six
Flare of Passion
Geoffrey quietly slipped the bolted lock, eased open the back door a crack, stuck his head out, and surveyed the broad gravel driveway, checking each of the outbuildings that clustered behind the Manor House for signs of life. The scene was perfectly still; the yard deserted. This was beyond his wildest dreams! Tingling with excited glee, the young lad scurried directly across the crunching gravel in the loping strides of a long-legged wading bird, hurrying to where the wide stable doors stood gaping in open invitation. He quickly ducked inside the shadowy barn. He had made it!
Pausing to collect himself, he leaned back thankfully against a square wooden column, breathing heavily, his heart racing. So far, so good. He took a deep breath, letting his flaring nostrils fill with the sweet smell of warm dampness mingled with new-mown hay. As his eyes adjusted to the darkened interior, he looked towards the row of stalls.
The rig was gone, and so three of the girls had to be out as a team. He had watched as Cupcake and Stormy were led to the exercise yard for their morning workout. That meant only one ponygirl was left in the stable -- Snicker. But to his surprise the one he found there was not the comely and bouncy young girl he expected, but the cool and remote Flare who had been left behind, and was now the sole occupant of the stalls. The top half of her stall door had been swung back, and the view provided was from the waist up, a lightly-tanned naked girl framed by the square opening, silently regarding him with those wide, dark eyes of hers. He was clearly surprised to see the auburn-haired ponygirl, but if she was surprised to see
him
there was no sign of it on her expressionless face. She simply regarded him coolly and evenly, and in perfect silence.
He wasn’t surprised that she didn’t say anything. Ponygirls were not permitted to speak unless spoken to, although he knew they whispered to each other when they thought they were safely out of earshot of the grooms. Geoffrey knew a lot about the daily lives of the ponygirls. He spent whatever time he could spying on them. To say he was fascinated by his Uncle’s prized collection would be an understatement -- the young lad was positively obsessed!
Visions of naked ponygirls prancing in high-stepping tandem, kept the tormented teen in a more-or-less permanent state of sexual arousal. His days were filled with embarrassing incidents as the healthy young lad seemed to be constantly walking around with an all-too-obvious erection obscenely tenting the front of his jeans. He would never forget the humiliating accident he had that day when playful Stormy had abruptly backed up into the surprised teenager, pinning him to the side of the stall while giving a devilish wiggle to grind her naked rump hard into his blue-jeaned crotch. Before he realized what was happening young Geoffrey had creamed his jeans! He stood there aghast, mortified to feel the warm stickiness as the telltale stain spread across the front of his pants in front of his indulgent uncle and the wide-grinning groom.
Days and nights in the sexual hothouse his eccentric relatives had created at that remote Estate, kept the randy lad in constant heat. Several times a day when the hard fury of unrelenting sex gripped him, he had rush to his room to seek a few moments of blessed relief provided by his pleasuring hand. Nights were sheer hell. He went to his bedroom early. Hot and sweaty, he tossed restlessly with a fistful of tangled sheets wrapped around his painfully stiff cock, pumping his hand, masturbating furiously, through climax after climax, till blessed sleep finally released him from his burning torture.
Now, as the barely-breathing boy and the proud ponygirl stood sizing each other up, he felt his penis stirring in his pants, awakening to the call of duty. He was struck by the way twin beams of sunlight streamed down to set ablaze the soft folds of auburn hair that gave the girl her pony name. As in a dream, he moved closer to her stall. Those hard, curious eyes followed him, looking up at the tall lanky boy from under a smooth fold of burnished hair that angled down to sweep rakishly across her brow.
Geoffrey had been planning this rendezvous with Snicker in mind because, although he was taking a chance being alone with the bubbly and sprightly girl, he was pretty sure he would get a welcoming reception. But the older Flare was an altogether different matter! While he lusted after the perky Snicker, he positively adored the unapproachable Flare. The lad was awestruck the first time he laid eyes on her: she was the most beautiful girl he had ever seen. No, not really a girl, he reminded himself, but a woman, a mature, exciting woman, devastatingly attractive, and deeply sensual. (If the truth be told, the ponygirl, now known as “Flare,” was a good-looking young woman in her early 30s, but in the smitten eyes of the sex-crazed teenager, she was the epitome of mature femininity, an elegant, experienced woman, so terribly, achingly desirable.)  His penis surged into full prominence, and he tried to swallow down the knot of lust that constricted his throat.
His eyes took in the strong-boned yet handsome features of that fine womanly face, the strong nose with wide-flaring nostrils, and the wide painted lips with just the hint of pout to the lower one that protruded slightly. Her brows were angled upward from the center, and with the skin pulled tight over her high cheekbones, they lent her the fierce pride of a raptor. The slender column of her neck had been banded by the high 4-inch collar of soft leather which she wore with certain air of arrogance. Was this beauty actually proud to be collared? His eyes fell down her front to her naked breasts, not large, but wide-set flattened mounds, tautly-drawn, with tight nipples that jutted straight out from their very centers. He stared at her bare breasts; she let the boy look, answering his questioning eyes with total indifference.
Summoning up his courage, he raised a trembling hand to reach for her.
“Well, what have we here?” The ringing words shocked him from his revelry; he spun around and whipped his hand down as if he had been burned! Struck speechless, he found himself facing his imperious aunt, her trim figure clad in a smart riding outfit.
“Aunt…Ursula…I,” he managed to get out, as she strode up to him with her usual
savoir-faire.
His aunt, he had discovered, was unflappable. A jaded woman of the world, who seemed absolutely shock-poof. She took everything life had to offer in her stride, a useful attribute when living with such a happily perverse husband. The sight of her curious nephew slinking around the stables to cop a quick feel of a ponygirl was hardly a discovery of note to her. She was actually surprised that he had not attempted such a sally sooner, as any red-blooded boy was bound to do.
“Oh, Geoffrey…Geoffrey…Geoffrey,” she tsked, shaking her head knowingly. “You really need not skulk about so. If you want to visit our girls, simply
ask
, darling.” She stood close to him, searching his embarrassed eyes. Unable to meet her gaze, Geoffrey lowered his head, like a rueful schoolboy caught looking up a dress; but she would have none of it. She placed a single finger under his chin and raised it up, to look in his confused eyes, and give him a big, understanding smile.
“Come now. Nothing to be ashamed of. It’s quite natural, you know, a big healthy boy like you is bound to be curious about girls. You’re growing up. It’s obvious.”
She looked pointedly down at his crotch, gave him a wicked smile and a knowing wink, which sent Geoffrey blushing furiously. Ignoring his obvious embarrassment, she rattled on conversationally.
“I was telling Basil just the other day: it’s time young Geoffrey became better acquainted with the opposite sex. And since the court in its wisdom has made you our ward, it’s up to us to see to your education. Now come along lad. It’s time Auntie Ursula took a hand in your education. Your Uncle and I know a few things about girls that will stand you in good stead in the years ahead. Shall we start our first lesson with Flare here?”
The lanky boy, still recovering from the shock of being discovered, could only manage a weak smile and a nod of his head. She smiled back and opened the bottom of the stall door, beckoning its sole occupant out to the center of the stable.
Walking barefoot on the straw, the beautiful ponygirl emerged into the light, her head held high. She was of course, naked, wearing nothing but the leather collar, and the cuffs that banded her wrists and ankles. The russet-haired woman, like all the ponygirls, was unselfconsciously nude. She obeyed with aplomb, answering her mistress’ summons with self-assured poise, stepping up to stand before her visitors at loose attention: shoulders squared, chest out, passive eyes straight forward.
Both observers stood for a moment contemplating the beauty of the nude who offered herself for their appreciation. “Oh yes, our Flare’s a pretty one, isn’t she. So very petty,” the Lady crooned, reaching up to thoughtfully finger a single tress of the motionless nude’s silky hair. “And well-trained too, you’ll find. Yes, I can see you’re developing quite an eye for feminine beauty, my boy. You enjoy her breasts of course,” she teased, seeing where the boy’s gaze had immediately fixated. “Yes, they’re lovely.
And look at that pussy,” she added, as her nephew’s eyes obediently followed the instructing finger that now pointed to the triangle of soft reddish pubic hair. “Quite adorable, I’ll grant you.”
She took a step back, and continued in the dry, discursive tone of a classroom teacher. “But there are others things to consider, my young lad, if you are to become a man who truly appreciates women. To be true connoisseur of feminine beauty, you must consider the totality of the woman, all that makes her who she is. You must show her you appreciate each unique gift she has to offer.
To truly enjoy a woman she must be willing to offer herself totally, body and soul. And she’ll only do that if she must feels truly appreciated for those things that are unique to her, that set her apart from her sisters. The best of men understand that to bring out that emotional response they must learn to cherish the little things, the subtleties the female offers to the male in the eternal dance of the sexes. One day you’ll realize it’s more than tits and arse, my lad, so much, much more.” Throughout this monologue young Geoffrey gaze remained riveted on Flare’s pussy. He could barely make out the slit through the tangled haze of pubic hair.
Aunt Ursula glanced over and gave him a dubious look.
“Here, let me show you. Come.” She beckoned the young woman to her.
The girl stepped up to stand just in front of her mistress and this brought her even closer to the wide-eyed boy. It excited him to be so near to her, to have the tanned and healthy ponygirl standing before him, her wonderful womanly body totally naked, so available -- and just inches away. He could taste his rutting lust. He wanted to fuck this most desirable girl in the worst possible way.
But Lady Ursula had other ideas. She reached out and laid her hands on the girl’s bare shoulders, smiling into those steady eyes. For a moment the two women regarded each other, looking into each other’s eyes. It was Lady Ursula who looked away first. Still smiling she began moving her hands to follow the roundness of those gently sloping shoulders. She followed down the smooth contours of the upper arms then backtracked to journey upward to the neck. Both hands slipped under the heavy mantle of red-gold hair to curve around the neck just above the collar. While one hand held the cupped the nape of Flare’s neck, the fingers of the other explored the thick band of leather. Geoffrey watched paralyzed while Lady Ursula fingered her ponygirl’s collar and then toyed with the dangling O-ring at the front. A finger hooked into the ring, and the Lady used it to draw the girl to her. Then to the surprise and astonishment of her on-looking nephew, she leaned forward and kissed the ponygirl, right on the lips! The ponygirl stood stock still, hands dangling helplessly at her sides; simply letting herself be kissed by the other woman.
“Oh yes, very pretty,” Ursula breathed in a husky voice, as she released the girl. “And such lovely hair…”
Her fingers played in the shock of hair that fell over the brow, sampled its silkiness between her fingers, and fluffed it up a bit.
“Some women become quite taken with their hair, you know; spend hours grooming and primping before their mirror. Did you know our Flare is just such a vain little girl, Geoffrey? Oh yes, she’s so proud of this hair of hers, aren’t you, my Pretty?” She took up a single strand; pulled it out; slowly drew on it till she saw the girl wince with the flicker of pain that passed over her face.
In the blink of an eye, the toying fingers turned vicious, digging into the thick mop, grabbing a fistful, yanking upwards. Taken by surprise, the girl sucked in an abrupt gasp of air through grinding teeth. Her eyes widened in alarm and her jaws clenched as she was hauled up onto her toes. Geoffrey was amazed to see that the girl’s arms did not rise in her own defense to grasp and struggle with the offending hand, nor did she attempt to pull away to free herself from the painful grip.
With hands still hanging uselessly at her sides, she simply endured being hauled up by her stretching hair. The lad saw a decidedly evil grin come over the smirking face of Lady Ursula as she slowly drew her fist backward forcing the girl to arch back on tiptoes and drawing forth an involuntary tight-lipped grunt.
For a moment his aunt held her victim suspended like a tightly drawn bow while tears welled up in the ponygirl’s eyes. Geoffrey, fascinated, could see the silent plea in those widened eyes, although the girl never uttered a word, never begged for mercy.
“We shall have to give some serious thought to this hair,” his aunt continued in her dry business-like tone.
“Yes, I think I shall suggest to Basil that we have it all shaved off -- clean as a billiard ball!” she crowed. “A lot less to take care of. You’d like that, wouldn’t you my Pretty?” she hissed, twisting the fistful of air as the girl’s face scrunched up in pain. “Well!!!”
BOOK: Ponygirl Tales
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