Riding Lesson Ch 01

*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.