4 comments/ 35846 views/ 6 favorites Riding Lesson Ch. 01 By: DeaGodiva *Any likeness to real people or places is not intended and purely coincidental.* Ashley plunged the generously lubed dildo into her pussy until all eight inches were buried in her willing hole. With her other hand, she stroked her clit and moaned, greedily rocking her hips against the pressure of the dildo. She began gliding her toy rhythmically in and out of her pussy, and every time it sunk to the hilt, the head of the prick rammed against the deliciously sensitive wall of her cervix. She could feel the pressure building within her lower belly, and her fingers frantically worked her clit until her hand ached. One final stroke with the dildo sent her over the edge, and she let out an enthusiastic squeal that would have made her cheerleading captain proud. She lay there on her back, breathing heavily and savoring every last ebbing wave of the orgasm. The dildo was still crammed in her slit, and when she slid it out, she sighed like a well-fed pussycat. There wasn't enough time before her riding lesson to truly bask in the wake, so she sat up and reluctantly left her bed. She really took her time in the shower, using an exfoliating sponge on the curves of her body and soaping between the tender folds of her bald pussy. She had just gotten a Brazilian wax the day before, and every inch of skin was neatly clean of hair. Ashley liked to call it an A to P—ass to pussy—wax. The pain of the waxing was a small price to pay for a smooth, fuzz-free cunt. Normally, she would have lingered in the shower a few extra minutes to enjoy the blast of water from the removable showerhead against her clit, but today's lesson was far too important for her to be even a few minutes late. Instead, she turned off the faucet and quickly toweled dry. Ashley had been taking lessons at Renaissance Stables for the past two months. She had been riding casually since she was five and competing in Pony Club since she was seven, but really only to please her mother. Up until high school, most of her friends had been into riding, and hanging out with them usually meant she had to spend more time with horses than she would have preferred. Nevertheless, she was a social creature and riding horses got her more attention from boys, which were her true passion. After graduation, she would have given up riding completely if her friend Courtney hadn't told her about William Lehrer— the gorgeous, locally renowned Dressage Trainer and owner of Renaissance Stables. He was thirty-five, six-foot-six, and had the most finely sculpted ass that was perfectly accentuated by his immaculate designer breeches. The tan breeches also offered a lovely view of the sizeable bulge of his crotch. Despite never seeing him naked and hard, Ashley surmised that he was well over average length with a thick girth to match. Being instructed by him in the tedious exercises of Dressage schooling was just a side effect for her. She was really there for another purpose, and she was used to acquiring everything she set out to get. Ashley's closet boasted a collection of custom breeches and polo shirts for schooling, both in every different color. She also had a whole drawer devoted to specially padded sports bras and riding briefs, ordered for her by her mother. She dismissed this unflattering underwear and opted instead for a satin push-up bra and no panties. She slid on a pair of snowy white breeches that were normally reserved for shows and a tight pink tee with a deep, plunging neckline that boasted her ample cleavage. Sans panties, you could very obviously view the curves of her fat pussy lips beneath the white breeches. The color of the t-shirt flattered her tan skin and the hem was cut short, showing off her toned abs. Last but not least, she chose a pair of Italian calfskin dress boots to complete the look. The black leather was so buttery smooth it gave her a thrill to run her fingers over them as she slipped them onto her feet. She was really pleased with her appearance and posed for a few moments in front of a full-length mirror, cocking her hips and running her hands over the petite curves of her body. Before leaving, she spritzed on just enough perfume without reeking of it like a whore. When she arrived at the stable, her horse was already fully tacked and standing patiently on cross ties. Eminence's Grandee, or Dee, was an eight-year-old Oldenburg gelding. He was a little over 17 hands and a rich dark chocolate in color. Ashley's 5'3 frame was dwarfed against his towering height. She always felt like a small child atop his back, but she relished in the massive power of the horse between her slender thighs. More than that, she wanted William's power between her thighs, but the ends justified the means. She needed to get his attention first, and if that meant spending an hour practicing twenty-meter circles, so be it. William's assistant, a rather attractive boy in his early twenties, came out of the tack room. He glanced at Ashley and did a double take. His eyes traveled over her hungrily before he checked himself and slipped back into his customarily professional demeanor. Ashley couldn't have been more delighted with his reaction. If she hadn't had a grander objective, she would have made plans to have her legs hooked over that boy's shoulders that very evening. If all went well, maybe she still would some other evening in the near future. "Good afternoon, Miss Crane. Are you ready for your lesson?" He had the most adorable British accent. She thought she detected a little hitch in his voice as he spoke, and she definitely noticed a stir in the mound of his crotch beneath his breeches. She gave him a knowing, sugary smile and placed one hand on her hip. "I'm ready if you are, David." She couldn't resist indulging in a little innocent teasing with him. David noticed her suggestive glances and turned his body away from her abruptly, busying himself with releasing Dee from the cross ties. The big horse assisted by dropping his head, so that David could easily slip the reins over his head. Without another word, David led him down the pristine corridor of stalls towards the entrance to the indoor riding arena. Ashley could see he was walking a little strangely, awkwardly trying to conceal his boner. William was waiting in the arena. He always entered the arena for each lesson promptly on the hour. He was never a minute early or a minute late, and he never rescheduled appointments. He was like a well-oiled machine and his professional ethics were Spartan in every sense. This was just another aspect of his character that Ashley lusted over and longed to harness for her own desires. She fantasized that he would be just as diligent in making her cum, beginning their sessions on the hour and lasting throughout the night. She believed she would finally have a sexual partner that could keep up with her stamina and insatiable appetite. David brought Dee over to the mounting block in the center of the arena and began adjusting the girth and the stirrup leathers. William strode over to inspect his work, a long, slender dressage whip held in his gloved grip. He was wearing a smart pair of full-seat breeches in his usual tan with a black cotton polo tucked neatly into the waist. Ashley savored the view of his ass and well-muscled thighs that was afforded by the tailored quality of his riding breeches. She was getting wet just thinking about digging her claws into the firm cheeks of his buttocks. "David, you ass! These are unacceptable!" William had been inspecting the wraps on Dee's forelegs. He bent down and quickly unraveled them, tossing them aside onto the sand of the arena. "Go get more bandages and wrap them correctly this time! I won't ask you again!" As David turned to go, submissively nodding his consent, William swiftly raised the stylish dressage whip and cracked it firmly against David's ass. David yelped, but said nothing. Ashley had never seen anyone move as fast as David did across a sand arena in tall boots. She was stunned by William's reaction, although his temper was notorious and she had heard other stories of him making students cry, particularly girls her age. Still, she had never seen him use the dressage whip, other than to reinforce a command while riding. It sent a shiver up her spine, and she wasn't quite sure if it was from desire or just fear. It took a little while for David to rewrap Dee's legs properly. William supervised him every inch of the way and corrected him with a sharp word if he started to slip up. Up until then, William had completely ignored Ashley's presence. As soon as David finished his task and all gear was appropriately intact, he turned to her sharply and motioned her over with a curt wave of his hand. "Miss Crane, I apologize that we are starting our lesson behind schedule. It won't happen again, will it, David?" He turned his severe, blue-eyed gaze on his assistant and tapped the tip of the whip against his boot, as if to accentuate his words. "No, it will not. I sincerely apologize, Miss Crane." "Very well then, David. Please assist Miss Crane in mounting and then you may continue your other tasks." Ashley had already stepped up to the mounting block. She had on her schooling helmet, the strap securely under her chin. In spite of the fact that it obscured her lustrous blonde locks, she appreciated how pretentious and oddly seductive the helmet made her appear. On the platform of the mounting block, her body in the provocative outfit was boldly on display. David's eyes never left her curves as he held the stirrup in place for her left foot, especially when her movements brought her snatch only inches from his face. When he had fulfilled his purpose, he left the arena with one final reluctant look at Ashley. William appeared completely indifferent to what she was wearing. He only glanced at her face when he spoke to her, and Ashley was beginning to think her efforts had all been a big waste of time. Maybe William wasn't even interested in women. When she sat her full weight down in the saddle, she realized something fundamental that had not really occurred to her before. Although the dressage saddle was of a distinguished quality and padded for comfort in all the necessary places, without the riding briefs she was accustomed to wearing, her bare pussy was crushed against the rise of the pommel. It wasn't an entirely uncomfortable feeling. It was just something she wasn't expecting. She dropped her heels down, shifting her feet forward, and rocking her weight back against the seat to relieve some pressure. "Miss Crane, correct your alignment! I need to see your heel directly in line with your hip!" William barked, snapping her attention back to the task at hand. His expression revealed that he meant business. Ashley adjusted her seat, drawing her body to align with the imaginary line that runs through the ear, shoulder, hip, and heel of a proper dressage rider. The saddle grazed against the sensitive mound of her clit as she moved, and she had to suppress a gasp. She could already feel her juices wetting the crotch of her breeches. She sincerely regretted her decision not to wear underwear, and she knew she would be fighting to focus on the lesson. She hoped that William wouldn't notice her mistake. As if in answer to her inner dialogue, he spoke up clearly. "I haven't been at all pleased with your seat, Miss Crane. For this lesson, I'm going to remove your stirrups and hope that it will force you to deepen your seat and bring your knees more forward." Ashley stared back at him plaintively, chewing her lower lip. She wished she hadn't decided to be so cheeky. She could have advertised the delights of her body while still wearing padded riding briefs. Nevertheless, she was here now, and she wouldn't dream of backing down, despite the effort this would cost her. She moved each leg aside in turn as he removed both stirrup leathers from the bars. His actions were purposeful and he never touched her. Without the added balance of the stirrups, she was really forced to rely on her seat, and although she was able to sit back on her two seat bones, the fabric of her breeches was still rubbing insistently between her pussy lips. "Let's begin with 20 meter circles at a working trot. I understand this may prove difficult for you, Miss Crane, as you appear rather top heavy today, but perhaps you'll have assistance gripping the seat with your twat." Ashley's face flushed hotly when she registered his statement. Perhaps, he was far more attentive than she gave him credit for. As she nudged Dee into the trot, her voluptuous, bolstered D's began bouncing with the rapid, two-beat rhythm. It made her tender flesh ache, but she set her jaw and settled into the gait. Her pussy was beginning to throb with the friction of her breeches. She realized then that this riding lesson was not going to proceed in the way that she intended. Ashley was, by no means, in control of her situation. 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.