Riding Lesson

Catherine and Jeff had always enjoyed each other immensely with occasional adventures involving role-play style activities and sensual athletic escapades. Catherine was a perky, high-energy, 5'4" tall brunette with saucer-like brown eyes and unmistakable curves despite her occasional attempts to conceal them. She was just a couple years out of college, a career-oriented account executive for a regional consulting firm, and often still taught aerobics and kick boxing classes at the fitness club.

Being fourteen years her senior, Jeff was successful and deeply driven, yet in some ways often not completely satisfied with it all. He sat in a high-back black leather chair, reflecting on the events of last evening. He pondered the sense of calm within him and yet the renewed energy coursing through him. She strengthened and balanced him somehow.

This was a common thread between them, a part of the union. Days and, rarely, sometimes a week or more passed with little to no interaction between them, and then a call or a note would set the wheels in motion.

The call came from her this time - a simple message left Monday morning.

"I'm thirsty," she said.

He then prepared like a chef planning a meal. One part of the plan was a hand written note with three bright fluorescent yellow index cards enclosed in a plain white envelope. Each card was neatly titled with bold print, the words underlined: "Logistics", "Attire" and "Focus".

Catherine walked briskly and with purpose across the short parking lot, her hair pulled back and swishing with the fluid movement of her body. Like reading poetry, he could watch her in a variety of settings, studying and observing with appreciation. It was Wednesday - nail day, and a calculated guess on his part. The double chirp of the keyless entry sounded as she approached her pearl white Audi A4, opened the door, and slid into the driver's seat.

He watched and thoroughly enjoyed the expression on her face as she fumbled with the keys and reached for the white envelope taped to the steering column, the envelope guarding the keyhole like a manhole cover over a sewer line. She looked up briefly to complete a quick scan around the parking lot, the Innovative Salon sign glowing in the background, and was instantly more aware of her surroundings. She felt a twinge of excitement and anticipation as she fingered the envelope, smelled it, started the engine, tucked the envelope between her legs and drove away.

My mentor, she thought. His answer to my request.

"Catherine, you are quite correct, dear sweet girl. It has been a while since I have felt your lips pressed against mine… Tasted you…"

His voice was steady and confident as always, she thought as she stood in her fourteenth floor corner office listening to her private voice mail messages.

There were two from him, the second one a continuation of the first and closing with "I trust you've reviewed your instructions. Kisses, darlin'." It was a statement more than a question.

She had opened the envelope while waiting at a stop light upon leaving her lunch appointment some five and a half hours ago. When she pulled into the parking garage at her office tower and realized she was only a few minutes late she read the note and skimmed the boldly colored index cards quickly the first time, and then reread them a second time more slowly.

As before when sitting in her car and now standing in her office listening to the voice mail, she could feel the tension below her stomach, deep inside her, and felt the moisture building between her legs. The note and index cards titled "Logistics", "Attire" and "Focus" bouncing around in her mind.

He breezed through the afternoon focused on the day's business, with one minor exception. During a mid-afternoon conference call, he reached into a leather portfolio and from a concealed compartment pulled a 5x7 glossy photo. Mostly listening to the conference call, he allowed his fingers to trace and retrace the smooth edges of the photo.

The subject in the photo was perfectly centered on a large bed blanketed by a very dark, green comforter. She was there with her shoulders lowered, her head turned to the side, knees tucked underneath her almost naked body. The thin slice of white fabric from thong panties cut down the center of her ass with razor precision, perfectly framing the globes of her bottom which was elevated more due to the distinct arch of her back. The picture was her idea some time ago, a gift to serve as a pleasant reminder of her and visual stimulation on demand… A secret pleasure.

Thursday came and went for him - racquetball at the club with Jack for lunch and a salad on the way back to the office. He was 6'1" tall with strong shoulders and a trim athletic build. Salads had replaced burgers after his thirty-fifth birthday along with several other small adjustments to meet the desire to maintain a fitness level held through his twenties and early thirties.

Back at the office a mountain of work to complete before the end of the week was waiting. He purposefully only allowed small fragments of Catherine to filter through his mind, but as always let the background of his mind continue to build and refine the thumbnail sketch of the planned outing. Of course, there would have to be some time for more organized and specifically focused thought. Perhaps that time would be later that evening on the treadmill.

Catherine continued to go about her work routine with anticipation of playtime release and was happy that she was scheduled to substitute teach step class that evening. She knew the exercise would lift her but also knew that she'd have to forgo the self-pleasure she routinely enjoyed after exercise, instead focusing that energy on preparing and wrapping his gift. His instructions were clear.

Finally Friday and six forty-five a.m. arrived, and Catherine was sitting at her desk formulating her approach for the day. She pulled the envelope from her black leather portfolio, opened it and lifted the three bright index cards from it, laying the envelope on her desk.

"The early bird gets the worm…" The cheerful voice of her peer Meagan startled her.

"You bet it does," she replied, looking up and smiling, watching Meagan sashay down the hall and turn into her office. She and Meagan, while peers and office competitors, had formed a true friendship. They sometimes conspired to conquer the work world, sometimes flirted in a veiled way, and sometimes just talked. Most importantly, they trusted each other.

Turning her attention back to the cards, she flipped through them one at a time. Thinking to herself and reading "Logistics". Got it. "Attire". Easy as pie. "Focus - sharpened sensory awareness, directed masturbation, riding lesson(s)". The last one… She stayed with this one for a bit.

Always the prurient teacher, she thought, and smiled. These words had her mind flipping through a thousand scenarios. Catherine was burning hot inside and thirsty.

The time passed slowly for Jeff on Friday. It was a busy working day and yet he found it more difficult to keep his thoughts focused on the work activities at hand. Never being a clock-watcher, he noticed himself checking the clock often. Sometimes only fifteen minutes had gone by since the last time he glanced at it.

When noontime approached, he continued plowing through the work items planned for the day, determined as always to complete the scheduled items per plan. He was smoldering inside and hungry.

He arrived thirty minutes before three o'clock. Check-in was uneventful, minus the well-dressed Natalie with the white silky blouse unbuttoned just one button too far at the front desk. He drove the car to building number four and found the unit he was looking for.

After unlocking the door and dropping the black bag on the bed, he conducted a cursory scan and inventory of the suite. It was richly furnished, with a kitchenette off to one side, a standard king size bed on an elevated platform, a few pictures, desk, television, and a delightful overstuffed chair-and-a-half, complete with a wheeled ottoman. A long full-length mirror covered a section of the wall closest to the bathroom. The ottoman caught his eye for a brief moment and he gave it a test roll back and forth.

He emptied the contents of the black bag and deployed each thing to its appropriate place. He pulled the curtain aside to check the view into the parking lot without purpose. He lit a single black cherry candle, left the entrance light on its lowest setting, stripped down to his black CK boxer briefs, then plopped down in the chair-and-a-half to relax and focus.

She arrived two minutes early. He heard the sound of heels on concrete before he heard the soft knock on the door. He hesitated for a brief moment, flipped the entrance light switch off, stood behind the door and pulled it open while still standing behind it. He watched as she took two full steps into the room, stopped, then started to turn to speak.

"Shhhhhh ... Sweet girl", he whispered, slipping the small black leather blindfold over her eyes and securing it around the back of her head. Without a word he led her by the elbow closer to the center of the room and stopped when they were parallel to the mirror but a couple feet back from it. He walked a slow circle around her, smelling her, and when he was behind her again said "Strip" in a low but clearly demanding voice.

She unbuttoned and removed the dark navy blazer and unhooked the matching skirt, feeling it sliding over her hips and thighs to the floor. She stepped out of the skirt and began to fumble with the buttons on her silk blouse, adding it to the pile on the floor once she managed to undo all six buttons.

"Stop," he said, and walked another circle.

She wanted to jump him now and wished he would just throw her on the floor and fuck her silly. She knew better and concentrated on what she could hear, smell, and sense. Black Cherry, she believed. The "Focus" card - "sharpened sensory awareness, directed masturbation, riding lesson(s)," she thought, the words running through her mind.

The blindfold must be the sensory, or at least part of it... she continued.

Her thoughts were interrupted by the sound and feel of leather falling evenly across both cheeks of her ass - five strokes with the cat-o-nine tails evenly paced apart. The strokes were not hard, but the fifth one caused her to shift her weight and take one foot a half step forward, perhaps as a result of the fifth whack or anticipation of the sixth.

"Shame," he said with a chuckle from behind her. She heard the smile in his voice.

He stepped up behind her and walked her forward, grabbed her wrists and guided her hands to the wall just above the mirror. Then he leaned down and placed lingering kisses on first the right cheek of her ass, then the left.

"You must keep your hands on the wall," he said.

She was still wearing the remaining attire requested via the index card - three-inch pumps and stockings with an extra thick band of lace on her upper thighs, thong panties, and lacy bra, all ivory. Her French-manicured nails and hair pulled back into one bushy ponytail perfectly matched the instructions on the index card.

"A delightful job you've done wrapping my gift, as always," he whispered into her left ear.

"Thank you. I'm glad you're pleased," she breathed.

He let his right hand travel to her tummy and traced his finger along the fabric as she wiggled her hips back against him. In all of their antics, she knew the effect of her charms on him. He turned her head to the side and kissed her lips, chasing her tongue with his and pushed his hips into her. Even through the black boxer briefs the sensation was incredible. They continued this form of dirty dancing together for a few moments and then he backed away, instructing her to put her hands back up on the wall.

The plan was important, he reminded himself.

He thoroughly inspected and traced the curves of her body: her face, her breasts, the small of her back, her legs. He was teasing with his fingers, lips and sometimes that leather cat. She also thought she felt the silkiness of his tie tracing over her skin.

He removed her bra, letting it fall to the floor, allowing her hands to break away from the wall for a moment. With one finger he hooked the thin fabric of her thong separating her cheeks and pulled the fabric aside to blow his breathe across her wet pussy lips and smell her.

He used the thumb and forefinger of his left hand to spread the cheeks of her ass apart and after wetting the pinky of his right hand, ran it across her tightly puckered asshole. He always enjoyed the way she smelled and tasted. He purposefully left her pussy lips exposed as he released the fabric of her thong panties to the left side of her pussy. She felt him step away.

Without warning she felt vibration against her swollen clit, the tender bud already craving release. He worked what felt to her like a small egg back and forth, while she swayed her hips to get more of it. Then he taped it in place and left it on its lowest setting before stepping away.

He put a black rubber lifelike dildo in her right hand and instructed her to take it. She took it and immediately lowered it between her legs.

"No," he said. "Suck it first."

She put it to her lips and worked her tongue over the lifelike head of the rubbery cock.

"Now," his words came from behind her, "keep one hand on the wall, up on your tip toes, and show me. Do it slow at first."

She complied by raising her heels off the floor and pushing the fake cock inside herself.

"Put it all the way in, leave it all the way in, and move your hips to fuck it!" he demanded.

She did, and began rocking only her hips and humping the toy awkwardly. She was struggling to focus.

"Keep those heels off the floor," he whispered in her right ear, "and remember… NO cumming without permission."

She sighed heavily, but kept moving. He listened for her breathing and watched her reflection in the mirror as well as from her backside.

"Faster," he said more sternly.

She picked up the pace and began furiously pushing, almost stabbing at her hungry pussy, the already slippery black cock sliding easily past the folds of her lips and then deeply inside her.

She felt herself slipping into that space that she sometimes craved, sometimes feared, but always loved going. She also loved the idea that taking her there yielded to him the same release she got from going. The first smack of his hand against her bottom pushed her further into that space, not realizing until she heard his words that both of the heels of her pumps had touched the floor.

"Kick your shoes off," he told her, "and keep going."

"I said faster!" he demanded again, and she resumed her pace feverishly pumping herself even more quickly. Her breathing was jagged and that vibrating egg continued its constant inescapable buzzing. It was taped securely just above and partially on her clit, but not close enough to allow release.

"Please," she said almost inaudibly.

"What?" he replied.

"Please, I… I need to cum," she panted.

"Not yet," he answered. "You may put your heels back down on the floor, and move your hand and your ass more quickly."

She moaned and a low growl escaped her lips, but she complied. Standing at her left side, he slid his right arm across her lower back, around the right side of her waist across her tummy, harnessed her to him and bent her over a bit more. He could feel her legs shaking and the thrusts of her hips becoming much less controlled.

"Pleeeeeaaaasssse..." she whimpered.

He immediately turned the remote control knob on the vibrating egg to full speed and raised and lowered his right hand striking evenly across the cheeks of her ass several times.

"May I cum?" she squealed.

"Yes, now you may cum, sweet girl," he replied, with another torrent of quicker and lighter swats targeting each cheek of her warm bottom. He moved to slide his left arm under her to provide support for some of her weight.

His continued vocal urging for her to keep going penetrated her ears as the initial wave of her first orgasm began to wash over her. He enjoyed the feeling of her twisting against him, his arousal physically evident as he glanced in the mirror, admiring her and the thin sheen of perspiration coating her body. Her perspiration was mixing with his sweat and dripping between them.

His right hand found her hand between her legs and gripped the fake cock. They worked together to continue pushing the black dildo in and out of her dripping pussy, twisting on the way in and on the way back out. She reached her second, then a much harder third orgasm, leaving her body convulsing and clinging tightly to him, her weight supported by his left thigh positioned between her legs.

Searching out her lips with his own, he slid one finger under the elastic of the blindfold and removed it from her eyes. He pulled back for a brief moment to allow his eyes to focus on hers, reading them, and kissed her deeply again, pressing his chest against hers and feeling her heart beating.

"Thumpity thump," he said and smiled. Her only reply was a smile and the sucking of his bottom lip into her mouth, closing her teeth playfully on it, and holding it.

Pulling her upright and turning, his 8-½ inches of hard cock led the way to the bed. He sat her down on the edge of the bed and settled in behind her as he asked her to put her hands behind her back. She did and he slipped the leather arm binder first over her left arm and then her right arm, tightening the straps one by one. Her hands were still free, but her arms were secure in a u-shape behind her back.

"A new toy?" she asked.

He lay back on the soft pillows and motioned for her to come to him.

"A private dance and a riding lesson," he proclaimed. She knew her task in an instant and straddled him, but he stopped her.

"You're going to have to make me cum without taking me inside you," he instructed, and then pulled her hips towards his cock and guided her in a long deliberate stroke of her still steaming twat along the full length of the underside of his meat all the way from the base to the tip. Now she knew her task.

She found a rhythm even with her arms bound behind her back and pivoted her hips back and forth, stroking slow and then faster, alternating between lighter and harder pressure, using her swollen pussy lips to caress and work his cock.

"That's a good girl," he murmured as he stretched his arms out to the side and applied his own sneaky pressure upwards against her clit.

She stopped and swung her leg over, turning herself around to face away from him knowing how much he adored her bottom. She lowered herself back to his cock and continued grinding against him, adding little circles of her hips to her riding. She concentrated on the response of his body and quickened her pace and then turned back around.

Leaning back and finding a new rhythm, at times coming dangerously close to taking him inside her, she continued riding, swiveling her hips more quickly, locking her eyes with his. Her arms behind her, she remembered her hands were still free and wiggled in position to get both hands between his legs and gently cupped, caressed, and toyed with his balls until she saw the muscles in his stomach tighten and felt his hands on her hips.

"I'm thirsty for your cum," she stated and tightened her grip on his balls. They were full and tight and she knew he was riding along the edge. She twisted her hips lower and rode faster back and forth until she heard the low growl escape from his lips, felt his body tighten and saw the first long thick white stream of cum blast from his cock. It landed near his chest in a thick strip with two shorter bursts following behind it and off to the side. She always enjoyed feeling his balls let go when he came. She leaned all the way over to him and began working the cum between their bodies.