Fiction: The Best Boy (F/M)

Some more fiction for your reading pleasure. This one was a request from last time, from a commenter who asked for it the other way around.

1. FL1 May 2024 at 07:58

   Another outstanding and highly arousing story. Well done, you! It says a lot about your writing ability that subjects and themes I'm not normally interested in have me hard as a rock by the third paragraph.
   Any chance you could do a Mom/son spanking story, with similar sexual overtones?

   Replies

   juliesp1 May 2024 at 08:53
   Oh yes! That sounds like a nice follow-up! Men's orgasms are more fun to write about!
   Delete
   Reply
2. And so I present the following effort.
3. Same caveat as before. The boy is 18, but if you don't like the Mommy/son stuff, stop here!

The Best Boy

Chapter 1: Anticipation

It had been eight long years since the last time Jackson had felt the sting of his mom's hand on his bottom.

At ten years old, he had been a rambunctious child, always getting into mischief and testing the limits of his parents' patience. But when his father had passed away, everything changed. His mother, usually a strong and confident woman, had become fragile and distant, unable to muster the strength to enforce discipline on her only child.

Jackson himself had grown up in the years that followed, but without the guiding hand of firm and loving parents, he had begun to spiral out of control. He had fallen behind in school, skipping classes and mouthing off to teachers. His mother, who had once been so strict, had become a shadow of her former self, unable to bring herself to reprimand her son for fear of further damaging their already strained relationship.

It was not until Jackson had been told he would have to redo his senior year of high school that his mother had finally decided enough was enough. She could not bear the thought of her son's future being jeopardized by his reckless behavior, and so she had made a decision - she would become the disciplinarian her son so desperately needed.

As Jackson sat in his room, his heart pounding in his chest, he could hardly believe what was about to happen. His mother had told him, in no uncertain terms, that he would be receiving a long-overdue appointment with her hairbrush at bedtime. He had protested, arguing that he was too old for such punishment, but his mother had been resolved. She had spent far too long allowing him to run wild, and it was high time that she stepped in to set things right.

Jackson glanced at the clock on his bedside table, the glowing red numbers seeming to mock him with their unyielding march toward the inevitable. He had been told to shower and then wrap a towel around himself, after which he was to come and find his mother for his punishment. The thought of it made his stomach churn with a potent mix of fear, shame, and a strange, almost masochistic excitement.

As he stepped into the steaming shower, Jackson tried to calm his racing thoughts. He knew that he deserved what was coming to him – he had been acting out for years, with no one there to hold him accountable for his actions. But the thought of his mother, the one person in the world who he was certain loved him unconditionally, taking him over her knee and applying her hairbrush to his bare bottom was almost too much to bear.

He had been a young child the last time he had been spanked, and while the memory was still vivid, it was the humiliation that he found himself dreading the most. He was now a near fully-grown man, with a body that was all too aware of the changes that had taken place since his last punishment. The thought of his mother seeing him in such a vulnerable state, his dignity stripped away as he was likely reduced to a quivering, sobbing mess, filled him with a deep sense of shame.

As he toweled off and wrapped the soft terry cloth around his waist, Jackson tried to steady his breathing. He knew that he had no choice but to face his punishment, but the thought of doing so left him feeling small and helpless. He had always been so independent, so sure of himself, and now, with a single conversation, his mother had managed to reduce him to a trembling, uncertain boy.

He hesitated at the door out of the bathroom, his hand hovering over the doorknob as he tried to summon the courage to face what lay ahead. He knew that he could not put it off any longer - his mother was waiting, and she would not be pleased if he kept her waiting for too long.

With a deep, shuddering breath, Jackson opened the door and stepped out into the hallway. He could hear the sound of his mother moving around in her bedroom, her footsteps echoing softly. He knew that she was waiting for him, her hairbrush at the ready, and the thought made his heart race even faster.

He approached her bedroom and quietly knocked.

Chapter 2: Punishment

“Come in, Jackson,” his mother said calmly.

Jackson entered and saw his mother sitting on the bed, hairbrush in hand, her expression stern and unyielding. She looked up as he entered the room, her eyes meeting him with a steely determination that left him feeling even more apprehensive.

“Jackson, I believe we have an appointment,” she said, gently tapping the back of the brush against her open palm, her voice firm and unwavering. “Are you prepared for your punishment?”

He nodded, unable to find the words to express the tumult of emotions that were swirling within him.

“Very well,” she said, her tone brooking no argument. "Remove your towel and come stand before me."

Jackson's face burned with humiliation as he untied the knot at his waist, the towel falling to the floor as he covered himself with his hands. His mother gestured for him to come closer, and he complied, his legs feeling weak and unstable beneath him.

“Hands at your sides, young man.”

He bowed his head as his hands curled at his sides leaving him completely exposed.

His mother took in the sight of her nearly-grown son, his slight, unathletic body trembling with fear and anticipation. He could feel his mother's eyes on him, assessing and unapologetic, and he wanted nothing more than to run and hide from her gaze. But he knew that he could not escape his punishment, and so he stood there awaiting her next instruction. He felt his penis and testicles... hanging there... ridiculous.

“Place yourself over my knees, Jackson,” she said, her voice softening ever so slightly.

He hesitated for only a moment before doing as he was told, his body seeming to move of his own accord as he positioned himself across his mother's lap. He could feel the warmth of her thighs against his private parts, and the sensation was unnerving.

"This is long overdue, young man."

As his mother began to apply her hairbrush to his bare bottom, Jackson could hardly believe what was happening. The pain was intense, each stroke of the brush sending waves of fiery heat coursing through his body, but it was the humiliation that he found most unbearable. He was an almost grown man, and yet here he was, lying across his mother's knee like a small child, his dignity and self-respect stripped away as she spanked him with all the strength and determination of a woman who had finally found her resolve.

As the punishment wore on, Jackson's resolve began to crumble. He could feel the tears welling up in his eyes, and he fought to hold them back, not wanting his mother seeing him break down completely. But as the pain continued to build, the walls he had built around his emotions began to crack, and he could feel the tears spilling down his cheeks, hot and humiliating.

His mother, her voice gentle but firm, continued to spank him, her words punctuating each stroke of the hairbrush as she reminded him of the reasons for his punishment. She spoke of his poor choices, his lack of respect for authority, and the damage that his behavior had done to his own future prospects.

And as she spoke, Jackson could feel something within him beginning to shift. The fear and shame that had threatened to overwhelm him began to give way to a sense of understanding, as if he were finally able to see the consequences of his actions through his mother's eyes.

When the punishment finally came to an end, Jackson lay across his mother's lap, his body wracked with sobs as he clung to her ankle, seeking comfort in the one person who had always loved him unconditionally.

As Jackson rose, his mother, her own eyes filled with tears, held him close, her voice soft and soothing as she whispered words of forgiveness and understanding.

In that moment, Jackson knew that he had been given a gift – the gift of a mother's love, strong and unwavering, even in the face of his own stubbornness and defiance. And as he stood there, his body aching and bare and his heart filled with a newfound sense of humility, he vowed to do better, to be the man that his mother knew he could be, and to never again take for granted the love and support that she so freely gave.

With a gentle hand, she guided Jackson back to his bedroom, her heart aching as she saw the raw, red welts that covered his once-smooth skin. She knew that he would be in pain for some time, but she also knew that this was a necessary consequence of his actions.

Chapter 3: Aftermath

Jackson lay in bed, his mother had long since tucked him in as he still wept. As the minutes ticked by, he found himself becoming more and more aroused. The memory of his mother's firm hand on his bottom, the sound of the hairbrush connecting with his flesh, and the feeling of her warm, comforting embrace after the punishment had all come together to create a strange and unexpected sensation within him.

He couldn't understand why he was feeling this way, but he knew that he couldn't ignore it. As his arousal continued to grow, Jackson began to rub his penis, his mind filled with thoughts of the embarrassing and humiliating ordeal he had just gone through.

He couldn't believe that he was becoming aroused by the memory of being spanked like a child, but he couldn't deny the pleasure that he was feeling. The more he thought about it, the more turned on he became.

As he continued to rub his penis, Jackson's thoughts drifted back to the moment when his mother had told him to drop the towel and stand in front of her. He had never felt so vulnerable and exposed in his life, and yet there was something about that experience that had turned him on in a way that he couldn't explain. As he thought about it, his arousal continued to grow, and he knew that he was getting close to orgasm.

Just as he was about to reach the peak of his pleasure, he heard a knock on his door. His heart pounding in his chest, Jackson quickly pulled his hand away from his penis and tried to compose himself.

“Jackson, are you okay in there?” his mother called out from the other side of the door.

“Yeah, I'm fine,” Jackson replied, his voice shaky and uncertain.

“Okay, well, if you need anything, just let me know,” she said, her voice filled with concern.

"I will, thanks," Jackson replied, his heart still racing as he listened to his mother's footsteps receding down the hallway.

As soon as he was sure that his mother was gone, Jackson turned back to his bed and continued to rub his penis. He was so close to orgasm that he couldn't resist the urge to finish what he had started.

As he thought back on the details of his punishment, his mind filled with the memory of his mother's firm grip around his naked hips, the sound of the hairbrush connecting with his flesh, and the feeling of her warm, comforting embrace after the punishment.

With each stroke of his hand, Jackson's arousal continued to grow, and he knew that he was getting closer and closer to the edge. He could feel his heart racing in his chest, his body tense with anticipation as he neared the point of no return.

Finally, with a soft moan, Jackson felt the familiar surge of pleasure wash over him as he neared orgasm. He turned over onto his stomach, burying his face in his pillow to muffle the sound of his cries as he continued to rub his penis, spewing spurt after spurt of hot ejaculate onto his bed sheets, his body shaking with the intensity of his release.

As he lay there in a pool of his own making, his body still trembling with the aftershocks of his pleasure, Jackson couldn't help but feel a sense of shame and embarrassment. He had just masturbated to the memory of his own punishment, a punishment that had been given to him out of love and concern for his well-being, by his very own mom.

Jackson tried as best he could with a hand towel and a damp washcloth to clean his bedsheets. When he believed it good enough to pass muster from his mom who did the laundry, he lay down on the wet spot, and drifted off into a deep sleep.

Chapter 4: Discovery

Next morning, Jackson's mom changed the bedsheets in Jackson's room as usual on Tuesdays. As she removed the sheets, she noticed a stain on the under sheets. She knew immediately what it was – the residue of Jackson's masturbation. She recalled the sounds she had heard coming from his room the previous night and the conversation they had. She had asked him if everything was okay, and he had assured her that it was. Now, she knew what he had been doing.

She couldn't help but wonder if Jackson had been aroused by the thoughts of the spanking she had just given him. She remembered the feeling of his penis over her lap as she had spanked him – it hadn't been aroused at the time. She knew that Jackson didn't have a girlfriend, and she strictly prohibited him from viewing internet pornography. It seemed that her son's desires had been awakened by the act of discipline itself. Fearing he may become obsessed with her spankings, and deliberately misbehave in order to earn one, she decided that she needed to confront him about his behaviour and find a way to address his desires in a constructive way.

When he came home from school, she called Jackson into the living room for a serious conversation. She explained to him that she had discovered the residue of his masturbation on his bedsheets and that she believed it was related to the thoughts of his recent spanking. She asked him if this was true, and he, blushing furiously, first denied it; but eventually hesitantly admitted that it was true. He explained that he had never felt such intense desires before and that he didn't know how to control them.

She decided that she could use this situation to their advantage. She told Jackson that if he behaved himself perfectly for the next week, she would reward him with a gentle spanking that he would not dislike, and he could do as he pleased after. However, if he didn't behave, she would give him another, severe disciplinary punishment with the back of her hairbrush. This punishment would not be pleasurable for him in any way.

Chapter 5: The Week of Good Behaviour

As the warm water cascaded down my body, Jackson couldn't help but feel a mix of embarrassment and excitement. It had been a week since his embarrassing and painful punishment, a punishment that had left his mind reeling with thoughts of the spanking he had received. He knew he shouldn't have been craving this, but he couldn't help it.

He thought he was an 18-year-old boy, legally an adult, yet here he was, about to receive a gentle spanking from his mom. It was humiliating, but at the same time, it was a craving that he couldn't ignore. He had been on his best behaviour for the past week, trying to avoid a second dreaded hairbrush spanking that his mom had promised him if he misbehaved. Instead, he was hoping for a gentle, comforting spank that would somehow satisfy his twisted desires.

As he rinsed the soap from his body, he couldn't help but think about how he had embarrassed himself over the past week. He had been overly polite, doing everything his mom had asked of him without a single complaint. He had even surprised her by doing some extra chores around the house, just to ensure that he was on her good side. All the while, he knew that his mom was fully aware of what he was doing and why. She had a knowing smile on her face, one that made him feel both embarrassed and excited at the same time.

As he stepped out of the shower and dried himself off, he could feel his heart pounding in his chest. He knew that he had to go to his mom's bedroom, and he couldn't help but feel a sense of anticipation. This was something that he had been craving for a week, and now it was finally about to happen.

He looked down at his penis. It was already hard with excitement. He was embarrassed that his mom would see him in such a state.

Taking a deep breath, he wrapped a towel around his waist and made his way to his mom's bedroom. As he reached the door, he hesitated for a moment, wondering if he was making a huge mistake.

He knocked on the door, and his mom called out for him to enter. As he stepped into the room, he could see that she was sitting on the edge of her bed, a small grin on her face. He knew that she was well aware of what was about to happen, and he couldn't help but feel a sense of relief that she was willing to indulge his twisted desires.

Chapter 6: Intimate Preparation

His mom was dressed in a short silk nighty that left little to the imagination. Her long, toned legs were arrayed elegantly, and her wavy, chestnut hair cascaded down her shoulders and back like a waterfall. She had a small plastic bottle between her legs. Jackson felt his cheeks flush with heat as he took in the sight of his stunning mother.

"Hi, Mom," he said, his voice barely above a whisper. "I-I showered like you asked..."

She smiled warmly at her son, her eyes twinkling with mischief. "I can see that, Jackson. Now, come over here and let's get started."

Jackson hesitantly stepped forward, his bare feet sinking into the plush carpet as he made his way towards his mom's bed. He could feel his heart pounding in his chest like a jackhammer, and his hands shook as he fumbled with the knot of his towel.

"Just like that, Jackson," she encouraged, her gaze fixed on her son's trembling hands. "Drop the towel and let me see the state you're in."

With a deep, shuddering breath, Jackson untied the knot and allowed the towel to fall to the floor, revealing his naked body to his mom's appraising gaze.

As her gaze traveled down his body, the unmistakable evidence of his arousal stood out strongly, arcing up towards the ceiling as a young man's erect penis does. Jackson squirmed and his cheeks burned with embarrassment, but he couldn't deny the thrill that coursed through him as his mom's eyes lingered on his erection.

"Looks like you're ready for me, Jackson," she laughed, reaching for the bottle of baby oil between her legs. "Let's get you all nice and slippery, shall we?"

Jackson nodded mutely, his eyes fixed on the bottle of oil in his mom's hand. He wasn't expecting this! He knew it wasn't right, but he couldn't stop it. He watched as she poured a generous amount onto her palm, her fingers working the viscous liquid into her skin until it glistened in the soft light of her bedroom.

"Come closer, Jackson," she commanded.

With a mixture of trepidation and longing, Jackson stepped forward and positioned himself right beside his seated mom's nude thighs, his face flushing with heat from the proximity. He could feel his own rapid, shallow breaths, and the scent of her delicate perfume filled his nostrils, making his head swim with desire.

"Now, Jackson," his mom began, her voice gentle and teasing. "You've been a very good boy this past week, and so you've earned this." As she spoke, her hand began to move in slow, languid circles around the shaft of his penis, slickening it with the baby oil. Jackson felt a shiver run down his spine, his body responding to the tantalizing sensation of his mom's hand on his penis.

"Please, Mom," he whispered, his voice trembling with a mixture of fear and excitement. "I don't think I can take this..." His mom leaned in closer, his penis still in her hand. "Trust me, Jackson," she murmured, her voice laced with a hypnotic quality that seemed to wrap around him like a velvet glove. "I know what you need, even if you don't. But you can always tell me to stop if it becomes too much for you. Do you want me to stop, Jackson, hmmm?"

"N... n... no.... please...."

She smiled and withdrew her hand from his glistening penis standing firmly at attention. She poured some more baby oil over her nude thighs, lifting her nightie higher, and rubbed it in.

"Over my lap, sweetheart. Time for your spanking."

Chapter 7: The Gentle Spanking

Jackson, his heart pounding, lowered himself over his mom's lap, moaning as his hard slick penis contacted her silky soft, firm oiled thighs. She took some more oil and rubbed it over his backside, including into his bottom cleft and his high inner thighs. He jumped a foot as her hand briefly brushed by his tightened testicles and she laughed. Jackson tried to remain still, but the slightest movement brought a jolt of pleasure to his penis, and he began to move gently over her thighs as she laughed sweetly at his obvious excitement.

Done with the preliminaries, she raised her hand and brought it down gently yet firmly on his upturned backside, the sound of the impact echoing through the room like a gunshot. Jackson yelped in surprise, his body tensing at the unexpected sting of his mom's hand.

"Remember, Jackson," she reminded him, her voice soft and soothing. "You wanted this."

As she spoke, she continued to rain a series of firm, stinging smacks down on his backside, each one sending a jolt of pleasure-pain coursing through his body. Jackson found himself writhing and squirming under the onslaught, his hands clenching and unclenching as he struggled to process the confusing mix of humiliation and arousal that filled him.

"Please, Mom," he gasped, his voice hoarse with emotion. "I don't want this... I don't want you to see me like this..."

She paused, her hand hovering in mid-air as she regarded her son with a look of concern. "Jackson," she said gently, "I want you to know that I love you, no matter what. And I'm here to help you through this, even if it's hard for you to understand right now. Do you really want me to stop?"

"No..."

With that, she smirked and resumed her task, her hand picking up speed as she spanked him with renewed vigor. Jackson felt his body respond to the punishment, his arousal growing stronger with each stinging impact. He could feel his mom's thighs pressing against his erection, the friction sending sparks of pleasure shooting through him like fireworks.

As the intensity of the punishment increased, Jackson found himself on the verge of orgasm, his body teetering on the edge of release. He reached down and grabbed ahold of his mom's ankle, holding on for dear life. He knew that he should be ashamed of his own desires, but he couldn't help the overwhelming need that consumed him, urging him to surrender to the erotic sensations that threatened to overwhelm him.

"Please, Mom," he moaned, his voice thick with desire. "Please don't stop... I need this..."

His mom smiled, her eyes gleaming with a mixture of pride and desire as she watched her son writhe beneath her. "That's it, Jackson," she encouraged, her voice husky with passion. "Let yourself go. Embrace the pleasure and the pain."

As she spoke, she shifted her position, spreading Jackson's legs wide and exposing his inner thighs and tender, vulnerable bum crease to her punishing hand. Jackson cried out in protest, his body bucking and twisting as he tried to escape the relentless onslaught of his mom's hand.

"No, Mom!" he pleaded, his voice ragged with emotion. "Please, it's too much... I can't take it!"

But even as he spoke, he knew that his words were hollow, a desperate attempt to cling to the last vestiges of his self-control. In truth, he wanted nothing more than to surrender himself completely to the intoxicating mix of pleasure and pain that his mom was inflicting upon him.

As she continued to spank him, her hand strayed lower and lower until it grazed the tender, sensitive skin of his balls, Jackson felt his body tense and shudder, the first tremors of his impending orgasm beginning to ripple through him like waves crashing against the shore.

"Please, Mom!" he cried, his voice hoarse with need. "I'm going to cum... Please don't make me do this!"

His mom laughed, her voice rich with amusement and desire. "Oh, Jackson," she teased, her hand moving faster and faster as she drove him closer and closer to the edge. "You know you want this. You know you need this."

With a final, desperate cry, Jackson gave in to the overwhelming tide of pleasure that washed over him, his body convulsing and spasming as he was swept away on a wave of euphoria. He felt his mom's hand between his leg closing around his erection, her fingers working him expertly as she prolonged and intensified his release, drawing out the exquisite agony of his orgasm until he thought he would surely lose his mind.

As the last vestiges of his pleasure ebbed away, Jackson lay panting and spent across his mom's lap, his body slick with sweat and the remnants of his own release. He felt a strange mix of shame and satisfaction, the realization of what he had just done sinking in like a lead weight in his chest.

"Oh my goodness, Jackson!" his mom said, laughing. "You really need a girlfriend!"

Jackson nodded mutely, his eyes still glazed with the remnants of his post-orgasmic bliss. He felt his mom's hand on his back, her touch warm and comforting as she guided him to his feet.

"Come on, Jackson," she said, her voice laced with a teasing, playful tone. "You need to go fetch a washcloth and clean up that mess you made on my legs."

Jackson blushed furiously, his cheeks burning with embarrassment as he stumbled towards the bathroom, his legs still shaky and unsteady from the intensity of his release. He first cleaned himself and then dampened and then took a washcloth and a dry hand towel and went back to his mom who was still sitting on the side of her bed, leaning back on her elbows, her knees tightly together to catch any droppings, her nightie high, exposing just the very bottom gusset of her white panty, a grin playing across her face.

Jackson knelt in front of his mom and used the damp washcloth to clean the mixture of cum and baby oil that coated her thighs.

"A little higher, Jackson," his mom said as she spread her legs exposing her high inner thighs. Jackson dutifully cleaned and dried the entire area as his mom looked benignly down on her newly obedient son.

"Now, sweetheart, you've set the bar very high with your behaviour this past week. Keep it up and two weeks from now we can do this again, but you'll have to ask me. Otherwise, Jackson..." she continued, pointing at the solid wooden hairbrush lying on her dressing table that had so blistered him last week.

Jackson shuddered and resolved to be the best boy he could possibly be.

FIN

Any more requests? Please let me know in the comments!