Riding Lesson Ch. 02

After ten minutes at a working trot, William asked for more twenty-meter circles at an extended trot. Ashley could glimpse the clock on a wall just outside the arena. Her heart leapt with hope. Her hour was nearly over, and she knew William wouldn't extend the lesson.

At this point, an orgasm was accelerating in her loins like a souped up Bugatti. Her breeches were clinging to the insides of her thighs with a heady mixture of juices and sweat. She was fighting to maintain her posture against the incessant trembling in her knees, and her pussy was feeling hot and raw from the friction against the leather. When Ashley checked the clock again, it was one minute past the hour; and still, William asked her to practice leg yielding at a working trot.

When she shifted her weight in the saddle to her left seat bone to cue for the yield, a deep moan escaped her lips. Her hips gyrated against the rise of the saddle involuntarily, and she reached down to tightly grasp a handful of Dee's mane to catch herself. She was so close to cumming, she was on the verge of tears. As soon as her fingers tangled in his hair, Dee stopped abruptly and stood, squarely and attentively, waiting for a command.

Ashley braced herself for William's rebuke, but he was silent. Instead, he approached Dee's shoulder and stood staring up at her with a grim expression. He patted Dee's damp neck appreciatively, like a quarterback congratulating his teammate on a good game. The only warmth Ashley ever saw William display was towards his horses.

"Dismount, Miss Crane."

Ashley noted that this was a demand, not a request. Despite the desperate aching and shivering in her thighs, she leaned forward towards Dee's neck, swung her right leg over the back of the saddle, and slid to the ground. Her knees nearly gave out beneath her, but William didn't reach out an arm to catch her. Ashley couldn't be sure, but she thought she detected a hint of excitement in his cold, blue eyes.

"Retrieve the stirrups," William commanded simply.

She felt a hot flash of anger rise up within her at his audacity. She paid him to instruct her, and tacking and caring for the horse was never part of the bargain. Defiance quickly replaced her feelings of itching desire. She set her hands on her hips and opened her pert little mouth to dispute his order.

William beat her to it. With a flick of his wrist, he cracked the tip of the dressage whip against her bare, flat tummy. It was a very light touch, hardly enough to leave a mark; but Ashley jumped and let out a little cry. She was accustomed to his verbal abuse, but she was not prepared for it to become physical. Tears welled up into her eyes, but she bit her tongue hard and held them back.

"Retrieve the stirrups," William repeated.

He didn't leave her any room for argument, and Ashley was beginning to feel afraid. She began walking slowly across the arena to the half wall adjacent to the corridor, her legs trembling even more now. She could feel William's eyes on her as she walked, scrutinizing every minute detail. When Ashley reached the wall where the stirrups were hanging with their attached leathers, she noticed a coil of black nylon rope hanging beside them. She picked up the stirrups and started to turn.

"Good, Miss Crane. Bring the black rope with you as well."

Ashley hesitated and frowned. Why on earth would he need rope? She grabbed it anyway and walked back to stand in front of William. Without ceremony, he took the stirrups and reattached them to the stirrup bars on the saddle. Then he also took the rope and began quietly unraveling it. Ashley fidgeted and tugged at the hem of her t-shirt absently.

"Are we finished, William? If you don't mind, I'd like to go home and shower."

She lifted her petite chin boldly as if daring him to challenge her request. William ignored her pointedly and continued disentangling the rope. His gloved fingers worked deftly, and when he was finished, he finally turned to her squarely.

"Turn around, Miss Crane.

Ashley looked perplexed. "Why?"

William picked up the whip where he had dropped it on the ground beside his boot. Before Ashley could bat an eye, the tip of the whip snapped against the fleshy mounds of her breasts that were exposed above the t-shirt. She yelped and an errant tear escaped and slid down her cheek. She tipped her chin to look at her décolletage and a welt was already blooming against the otherwise perfect skin.

"Turn around, Miss Crane, and remove your boots."

Her mind was completely numb at this point. She had nothing left to do but turn around and bend over to remove her boots, as he commanded. As she leaned down to unzip the first boot, she felt the hard crack of the whip, this time against her left thigh. She cried out once more and nearly fell forward under Dee's belly.

When Ashley had removed both boots, she stood up and faced Dee's tall flank. Her face felt flushed, and her mind was racing. In spite of that, she felt the renewed tingle of yearning between her thighs. She had had guys spank her before during the throes of dirty passion, but she had never tried BDSM. She couldn't tell if that was what was going on here, and she was too rattled to ask.

"Remove your breeches."

Ashley turned her head to glance warily at William. She still had her helmet on, but she could see his face just enough to realize her hesitation was a mistake. Her right thigh received the sting of the whip. When she moaned this time, it was not only because of the pain but also from an unexpected surge of pleasure.

"I'm not going to fuck you, Miss Crane. Remove your breeches."

She could have sobbed with the crushing disappointment of what he said. Still, she fumbled to undo her belt and slide her breeches down over her tight, little bottom to her feet, removing them entirely and dropping them to the ground. She was standing there in only her t-shirt, bra, and silk, knee-high stockings, her bare ass exposed to William's gaze.

William drew one gloved hand back and brought it down firmly against one of Ashley's bare cheeks. He followed this with another admonition from his whip on the same cheek. The skin taut over the well-toned glute was resistant to the blow; and therefore, rendered a sharper pain than on her breasts. Ashley squealed from the pain, but she could feel the warm wetness returning between the exposed lips of her pussy.

She could feel William move behind her to stand at her shoulder. He no longer had the whip in his hand. Instead, he had the length of nylon rope, which he proceeded to loop around the stirrup on Dee's saddle. This stirrup leather had been brought up to its shortest length, so it was just above Ashley's forehead. William then turned to Ashley.

"Put your hands out in front of you."

Ashley did as she was told, desperately hoping that, in spite of his promise, this would conclude in him fucking her. William wrapped the rope expertly around both of her wrists and secured them together. The loops and knots he used seemed confusing to Ashley, and she felt sure it was something she could never wriggle her way out of. When he had tied her wrists, he fastened the end of the rope to the stirrup with the other and knotted them together tightly. Through all of this, Dee never moved. He seemed a party to William's intentions, as if this was something the horse had been trained to do.

When he was finished, William stepped back from his work. A moment later, she felt the sharp contact of both gloved hands against her bare skin—left ass cheek and right and the backs of both thighs. Over and over again, he slapped her flesh with the full open palm of his large hands. This feeling was something not alien to Ashley. She really enjoyed being spanked, but no one had ever spanked her this hard before. She shook with each blow and leaned into Dee's side. The immense horse fully supported her weight.

"Ohh, William," Ashley gasped.

The crack of the dressage whip bit into the flesh of her bottom again.

"You will not address me so informally, Miss Crane. You will call me Sir, but you will only speak if I ask you a question. Is that understood?"

Ashley nodded her head dazedly, but the whip snapped her again a little harder than before.

"Is that understood, Miss Crane?"

"Yes... Sir."

She stammered the words and gripped her fingers around the stirrup leather for more support. She wasn't sure how long her weakening legs could hold her up. More juices were beginning to trickle down her lean thighs.

William alternated between his hand and the whip, leaving behind a series of radiating stings on her bottom and thighs. Then he stopped, and she suddenly felt both of his gloved hands delve between her thighs and brusquely part them. She assisted and widened her stance. Then his gloved fingers roughly explored the folds of her pussy, teasing, rubbing, and pinching. Her thighs quivered violently, but she didn't cum. He didn't give her time to. He withdrew his hand and stepped to her shoulder again. This time he brought his hand to her face and slid two gloved fingers, covered in her juices, against her lips. Ashley's lips and teeth parted and his fingers entered her mouth, sliding in all the way to the knuckles. She could feel the pressure of his fingertips against her throat and she quickly swallowed before she could gag.

With his other hand, he reached down between her thighs again from the back, found her clit now poking from beneath the hood like the tip of a thumb, and pulled and twisted it. Ashley screamed loudly around William's two fingers and writhed helplessly. Once again, he began rubbing almost painfully between her lips and against her hot, swollen clit, while he finger-fucked her face. She felt that if she came, her head would explode. Just as she felt herself escalate to the point of no return, he stopped everything and took a step back. She quickly realized that he wasn't going to give her the satisfaction of release. This was intended as torture and punishment for her behavior.

Ashley was suddenly aware that there were tears coursing down both of her cheeks, and she was whimpering weakly. When William stepped back and resumed his punishment with the whip, she bit her lip hard and tasted blood. He was really wailing on her ass now, his strokes acute and intentional. Ashley couldn't take it anymore; she let out a shuddering scream, and her legs gave out completely underneath her. Dee and the saddle supported her full weight.

William didn't cease whipping immediately. After a couple more cracks, Ashley heard the whip hit the ground, and she breathed an audible sigh of relief. She was hardly aware when William stepped up to the saddle and undid the rope securing her to the stirrup, until she dropped to her knees in the sand footing of the arena.

She crawled into a fetal position by Dee's feet, her face wet and smeared with mascara, her hands still tied. Her ass was smarting so bitterly, she couldn't bear to sit up on her knees. She saw William walk across the arena to the far wall, and she thought maybe this was all over. A mixture of hopefulness and frustration accompanied that thought.

In a few minutes, he returned, carrying a ground-training whip, known as a "carrot stick". It was more flexible than the dressage whip and had a longer tail on the end. He set the "carrot stick" on the ground beside the dressage whip and bent down to grab the rope ends attached to Ashley's tied hands. He undid the knots securing her wrists as easily as he had tied them.

"Take off your shirt and bra."

Ashley wanted to resist. Her ass and thighs were raw and sore with all the bruising, but she knew better now. She would be punished more severely if she opposed him. Every movement pained her intensely, but she rose up onto her knees, lifted her t-shirt, and pulled it up over her head. Then she reached her arms behind her back and undid the push-up bra. When her voluptuous breasts escaped their confinement, she moaned and ran her hands over her aching tits. This obviously didn't please William, because he smacked one hand lightly with the "carrot stick".

"Bring your hands together behind your back."

He gave the command and then walked over to Dee and removed his bridle. Ashley blinked nervously as William removed the jointed stainless steel bit from Dee's leather bridle. He laid the rest of the bridle over Dee's saddle and commenced threading the nylon rope through the ends of the bit. His head free, the big horse shook his head once, but otherwise remained fixed to the same spot. William patted his neck again and then returned to Ashley.

"Open your mouth."

Ashley gulped and parted her lips, but before she could protest, William shoved the metal bit between her lips and teeth—the bit that was still salty with the taste of Dee's mouth. She whined pathetically as he tightened the rope behind her head, just underneath the lip of her helmet, enough to secure the bit in her mouth. The loose ends of the ropes behind her head then traveled down to her hands again and were fastened around her wrists. From her wrists, the last bit of rope was tied most securely to her ankles, to anchor the entire length. She now had some idea how the horses must feel, and some part of her felt sorry for them.

She struggled to stay balanced in this position until she leaned her weight back so her bottom was rested fully on her heels. It hurt like hell, but it relieved the pressure from the ropes. Just as she was trying to get comfortable, William retrieved the "carrot stick" and stood in front of her, legs slightly apart. She had seen very little of him since she had dismounted. Now she was staring straight at his crotch. She was shocked to see that he had an enormous hard on throbbing beneath his breeches. It was the biggest bulge she had ever seen, and she could clearly view every inch of its shape through the taut fabric. It had to be at least 10 inches long—larger than she had imagined—and she knew he wasn't going to touch her with it.

William flicked the "carrot stick" expertly and tapped Ashley's breasts playfully a few times. Then he leaned over and flicked the left nipple with his gloved finger. Ashley wiggled against her restraints. He grasped the right nipple between two gloved fingers and tweaked it cruelly. She whimpered around the acrid salt and metal taste of the bit, and the tears ran down her cheeks in little rivers of black makeup. Then he drew back and cracked the "carrot stick" with an audible SNAP, the tail hitting her left nipple squarely. He didn't give her time to react before he was smacking both plump, round tits repeatedly with the smart, little tip of the "carrot stick".

Each time he struck her; Ashley flinched and squealed, squeezing fresh tears from her eyes. At the same time, rivers of pussy juice leaked down her thighs and onto her calves folded beneath her. The need for sexual release was so overwhelming at this point, she thought she might pass out. Still, William continued to beat her breasts with the whip, taking her to a state of pain and rapture that she had never before experienced. She had been fucked a great deal in her nineteen years, but she had never been "fucked" like this. She knew, without question, that she would never again be satisfied by anything—or anyone—else.