Mother Nows Best

This is the tenth story I've published on Literotica - and anywhere else, as a matter of fact - so I'd like to use this milestone to say thank you to everyone who has taken the time to read, like, or comment on any of my stories. Time is a precious commodity and I deeply appreciate everyone who has utilized it to find enjoyment in my work.

All the feedback and adoration has been overwhelming - in the best way.

The stories have all been a pleasure to write, and many are inspired by actual events in my life; they are all a piece of me in some small way.

Since first publishing on Literotica, it has always been my intention to release at least one story per week. Moving forward, I will continue to stay true to this promise and keep the depravity coming...

Please stay tuned (and let me know if you're a fan), there's plenty more to come!

~JJ

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Derek carefully pushed open the front door of his single-mother's house before stepping in quietly and closing it just as cautiously. His alert ears found that he had made no sound upon entering; the young boy suspected his effort was enough to not wake his sleeping mother from her slumber across the house.

He staggered, less gracefully, into the kitchen and retrieved a cold glass of water from the fridge. As he brought the cool glass against his lips and drank, doing what he could to chase away the bit of inebriation which still clung to him, his eyes found the digital clock just above the stove-top:

1:45

It was well past midnight; Derek knew he had to make his way silently down the hallway to prevent his mother from catching him sneaking out once more.

Over the last month, Lisa - Derek's mother - had found her 18-year-old son twice making his way back from who-knows-where, both at times even later than Derek now read from the clock. During both instances, Lisa hadn't the slightest idea that her son had even been out of the house; Derek had snuck out his window at some point and took off in his car.

In fact, since her son had graduated high-school nearly a month ago, Derek seemed devoted to disobeying his mothers instructions. After the second occurrence, Lisa knew she would have to take drastic measures if she planned on keeping her son under control. But she decided to wait until his next slip up to show just how serious she was about disciplining her young boy; it was the last bit of mercy she would afford Derek.

Now, cloaked in the dark of night, Derek was positive he wouldn't be caught.

Despite drinking hours earlier, he found some balance with his steps as he trailed down the main wooden hallway of the small home. It took him nearly a minute to tip-toe down the length the long hallway, only stopping for a brief moment as he crept by his mother's bedroom door. He noted that it was still closed; the sight him with relief. The last time he tried to sneak in it had been open, alerting him to the fact that his mother was awake and waiting to chastise him.

Comfort flooded Derek's body as he finally pushed his bedroom door open, gleefully shutting it behind him as his concerns melted away.

In an attempt to remain cautious, Derek left his light off as he undressed down to his boxers and crawled his way into bed. Once under the warmth of his covers, a satisfied smile spread across his lips brought on by the thrill of finally getting to party with his friends for a night without being found out.

Fading alcohol lingered his veins and helped Derek quickly drift into a deep, comfortable sleep.

All the while, Lisa sat and watched within the same darkened room, her wide backside planted firmly in a chair placed in the corner furthest from her son's bed..

Derek had never once noticed her as he stripped down and prepared himself to bed.

Lisa listened intently as Derek faded out on waking consciousness, his breaths eventually transforming into soft snores...

* * *

Derek's young mind produced muddled and abstract dreams, only partially legible to his thin understanding of reality. Occasionally there would be a flash of an image he could recognize: a tree, a cloud, a can of beer. None of it made any sense or carried any meaning to him.

Suddenly, the nonsensical fog retreated as a sharp pain bled into his sleep.

The left side of Derek's face was burning.

His eyes burst open to find that Lisa had planted a firm, open hand slap across his cheek.

For a moment he thought he was still asleep, only to have the fleeting illusion shattered as his mother came down with another, equally fierce, slap against his right cheek.

"M-mom... mom! W-what the hell?!"

As Derek protested, he suddenly realized he had been stretched out. All of his limbs were facing different corners of his wooden bed frame and any sheets that once covered him had been stripped away.

In a quick motion, he worked to bring him limbs back towards him to potentially defend against another blow from his mother.

They wouldn't budge.

"You won't be going

anywhere else

tonight," Lisa informed Derek coldly, her imposing figure towering over her son from the side of his bed.

Derek had developed normally for a young boy of his age, but he never came close to reaching the height of his mother. Lisa, twenty years Derek's senior, stood a good four inches taller than her son. Her tall frame carried her 190 pounds well; Lisa easily had 50 pounds on her son. But Lisa's mixture of height and weight blended themselves into a wide, powerful body.

Even in the pale moonlight that dimly lit Derek's bedroom, he could make out his mother's vivid contours thanks to the tightly fitted nightgown she had worn to bed earlier that same evening.

"Just what am I going to do with you... you really fucked up this time, Derek."

Once more, Derek tried to retrieve his arms and legs to no avail. His head swiveled around wildly to find leather straps holding him in place, each one fastened to a different corner of his bed.

The alcohol must have really done a number on him, Derek thought, because he hadn't stirred in the slightest while his mother had fastened him in place.

Lisa's face was mostly emotionless as Derek's frantic attention turned away from his bonds and returned to his mother. He quickly picked up on something fearful behind her dark eyes; it was a look that Derek had never seen on his mother before.

Lisa wore a devious expression.

A hint of panic crept into Derek's voice: "O-ok Mom, I get the point. I screwed up; it won't happen again. Just stop messing around..."

"Oh, I'm not messing around," Lisa snapped back sharply, now leaning against the side of the bed with her thick, tall frame.

"You've left me

no choice

, honey. Verbal threats simply don't seem to faze you anymore. I have no choice but to move on to something more

physical

..."

Lisa's intentions shot a chill down Derek's spine.

"

She can't be serious; what's the worst she's going to do? Spank me?

" the young boy foolishly thought just before watching his mother make her way up onto the bed. With an elegant move, Lisa took a couple of steps and found her balance on the mattress; she leered down at her son, standing tall above him near his feet

"C-cmon mom, what are you d-doing?!"

Derek's words stuck inside his throat as he watched his mother grab the edges of her snug, one-piece nightgown and, with her red, painted fingertips, begin to raise the soft fabric up her legs. Lisa crept the patterned dress inch by inch up her shaped thighs, each moment revealing more of his mother than Derek had ever seen.

Her fingers never quit tugging the dress upwards, and in just a few seconds Lisa had the gown at her waist.

In a mixture of horror, surprise, and twisted delight, Derek could now clearly make out his mother's powerful thighs swallowing up a thin, but well fitting, pair of black, lacy panties. From there, Lisa's shadowed contours led into an erotic valley at her crotch while the edge of the nightgown playfully swayed just above her panty-line.

Lisa expected her son to look.

And look on Derek did; he watched his mother's fingers now grasp her panties at each side before shimmying them down her body carefully. The tight nightgown hung In place, clinging to Lisa's soft skin while the small panties stuck to her, its center seemingly not wanting to leave from between her legs. A last, firm tug caused the stubborn undergarment to give way, exposing a carefully trimmed tuft of black hair just above Lisa's sex.

Derek's gaze couldn't peel itself away as his mother precisely navigated the panties with her delicately manicured fingernails down the remainder of her wide, but toned, thighs.

The young boy's words came out in gasps: "Mom, w-what the hell are you-"

Before Derek could utter another word, Lisa brought the now-removed black lace underwear to her son's lips. They were large; wide enough to fit around Lisa's hips and cover her. The fabric managed to be long enough for Lisa to wrap around Derek's busy lips and tie into a knot, creating a makeshift gag.

A pungent scent poured off the fabric-gag into Derek's nostrils.

"Shhhhh..." Lisa insisted, hushing her son while putting a painted-red nail against her son's trembling lips, "this will be much more pleasant if you just be quiet and take what's coming to you".

Then Lisa returned her fingertips to her tight nightgown before bringing it above her chest, forcing her double-D bust to pour out into Derek's sight.

Finally, she slipped the thing past her head, removing the tight dress completely before quickly tossing it onto the dark floor.

Even under the dark of night, the moonlight trickling in from his blinds allowed Derek to see his mother's tall, powerful figure towering over him. Aside from her voluptuous breasts, Lisa had stripped herself totally bare. Her full bust hung in place, supported only by a lacy black bra which matched the lace panties currently tied around Derek's head.

Derek couldn't turn away from his mother's bare curves.

His breaths were becoming heavy against the cloth between his lips, while the smell of the thing was causing fresh blood to pound through Derek's body. The gag was soaked in the scent of a woman; it was a smell that the young boy was still unfamiliar with.

However, his body knew exactly how to react.

Without trying, his inexperienced cock started to heat up underneath his boxers. Derek could feel a warmth building with every beat of his heart, the aroma of his mother's panties further lodging itself into his senses.

Before long, even Lisa's glance and could make out the throbbing erection pounding against the soft fabric of her son's thin boxers.

A small smile spread across her lips.

She took in the sight of her bound and erect son for a few more moments - anticipation draped the air; the real punishment was about to begin.

Suddenly, Lisa turned around and presented her stripped, juicy backside to Derek. He could only watch as his mother carefully took a few steps backwards on the mattress, each one bringing her smooth skin closer to his gagged face.

When she was nearly standing over Derek's mouth, Lisa took a few small steps sideways to spread her legs before slowly starting to lower her impressive ass down towards Derek.

The sight brought fresh cries from Derek's lips, though they only came out partially understandable thanks to the black lace lodged inside his puckered lips.

"Mom... ughhh... hhggg... s-stop... what are- hmmmgg"

Lisa ignored his pleas; she knew she had to be strict, or her son would continue his pattern of disobedience.

So she remained firm in her convictions, continuing to drop her ass inch by inch until the crack of her cheeks dangled less than a foot away from her sons nose.

Lisa hesitated for a moment, gathering internal strength for what she knew she had to do next.

Meanwhile, new scents from his mother now tickled Derek's nose, intertwined with the aroma of the panties. The strong cocktail of sensations sent his cock into powerful pulsations despite his mind being panicked by his mother's erratic behavior. In fact, something primal inside of Derek was actually beginning to savor the invasive aromas; the young boy soon found himself unintentionally taking in deeper breaths in the hope of fully consuming the strange perfume his mother's orifices had produced.

In the middle of one of the heavy inhales, Lisa slammed her ass firmly down onto her son's face, trapping his nose between the her parted, smooth cheeks.

Instantly, new squeals shot up from underneath Lisa; hot, panicked air bathed her exposed pussy as she felt her son struggling against her smothering rear end.

"When you don't listen to what I say, you don't get to speak, understand? And when you continue to disobey, you don't get to

breath

!" Lisa barked, grinding her hips down hard against Derek with her last salable.

It was rough, but Lisa knew it had to be done.

Only something physical and extreme could whip her son into shape.

On he other side of the punishment, Derek's world became absolute darkness, an abyss created by the enveloping, wide ass of his mother being drilled down against his face. His nose took the brunt of the assault, with the pointy end actually partially entering inside the pink, puckered hole residing inside Lisa's ass cheeks.

Warm flesh met his own moaning lips as his mother's ass worked to consume him entirely.

Seconds went by where the only thing that Derek was aware of - other than blackness - was the deeply intense twitching of his erect cock. The young boy's penis responded eagerly in submission to his mother's punishment; it was aching to be touched.

Then something else became terribly apparent to Derek: he needed to breath.

Not just needed; his entire body was screaming for it.

But any attempt at fresh oxygen was met by the black lace gag being forced further into his mouth by the downward pressure of his mother's plump ass.

Derek's limbs started to flail about in their leather bonds, desperately struggling for any means of escape.

Lisa kept her hands at her side, working to maintain her balance under the wriggling heap of flesh underneath her. Her dark eyes focused on her son's toes and watched them curl up as every visible muscle within Derek tightened.

Sensing that she had pushed Derek to the brink, Lisa lifted her hips and released the vacuum her ass had created against her son's face.

Fresh air instantly raced inside the parted valley between mother and son.

Lisa heard her son inhaling fiercely underneath her and felt Derek's warm breaths tickle her asshole which now hung just an inch or so above his nose. She decided to allow her son a few more moments of freedom from her powerful ass, while her eyes traveled down Derek's body and found her next target.

Her son's eight inch cock was thrusting against the thin white fabric that held it in, working on finding an exit.

Soon, Lisa would let the erection free. However, by the end of the night, Derek would wish his cock had stayed inside his boxers.

Without any kind of warning, and with a small motion from her core, Lisa pressed her ass cheeks back down onto her son. Once again, Derek's senses were forcefully shut off and consumed by the warm, pungent flesh of his mother's ass baring down against him, cutting off the once cool rush of fresh air.

This time Lisa never averted her dark gaze from her son's boxers while she pressed her backside, even harder than before, down into him. As seconds ticked by, she took a twisted pleasure at the sight of her son's young cock pulsating wildly, the rushes of blood filling the shaft becoming more intense with each passing moment Derek was without air.

It seemed her son, or at least part of him, was enjoying the trampling.

The pleasure resonating from between Derek's legs might have appeared to defeat the entire purpose behind Lisa's punishment, but it was exactly what she older woman had intended. To her, it present an opportunity to pursue a new avenue of discipline.

But she took her time, once more bringing her son to writhe beneath her consuming, wide ass cheeks. She felt Derek's hot mouth gasp just an inch away from her pussy; his lips were so close, but she wouldn't dare give him to satisfaction of tasting her.

Only once Derek was bucking with all his might underneath his mother's heavy frame did she tilt her hips up just the slightest.

Derek inhaled desperately, but found the pair of panties fastened around his head were restricting some of fresh air rushing in. The underwear-gag was now a moist, dripping thing that laid heavy on his tongue. Even so, he still managed to take in a fair amount of precious oxygen into his aching lungs.

To his relief, he watched his mother's ass continue to lift further away from him until Lisa made her way completely from over him and off the bed.

Without saying a word to her bound and gagged son, she quickly stepped through the dim moonlight and towards the hallway.

In a quiet panic, Derek's alert ears listened as Lisa opened her bedroom door just down the hall.

He couldn't waste anymore time; Derek knew he had to use this opportunity to free himself.

With what little energy remained in his strained body, the young boy went about tirelessly pushing his weight against the leather straps. No matter how much he contorted himself, he found himself still trapped to his bed, spread and ready for whatever Lisa had next.

The bonds didn't give an inch.

Before he could formulate any better means of escape, his senses picked up on his mother's heavy steps walking back towards him.

His gaze turned to see his Lisa's bare curves striding towards him. Her imposing figure was still only clothed by her bra, the small patch of hair just above her thighs still visible as she approached him.

Lisa carried a device back with her; it was something unfamiliar to Derek.

The thing was long and cylindrical; to him it looked like one of those back massagers he had seen while out shopping.

The machine that Lisa held tight in her grasp, as she climbed back above her son, was her Hitachi Magic Wand. It was a device that had given her many, many hours of pleasure, though now she intended to utilize it to further drive her punishment into her disobedient son.

After getting back down onto all fours with her heavy ass just inches away from its still-panting and gagged seat, Lisa wasted no time grabbing the waistband to Derek's boxers and jerking them down his tender thighs.

In a quick flash, his sensitive, veiny shaft thrust out into the air before Lisa's eyes.

Derek felt his mother exposing him and voiced fresh, pitiful protests from behind the panty-gag:

"Mmphhh... Mommphh.. stopphhh..."

Lisa quickly put a stop to her son's pleas for mercy the easiest way she knew how and quickly dropped her hips back down towards Derek's face. In an instant, her ass cheeks parted and buried his world down into their warm, tight grip.

The only difference from the past assaults was a slight adjustment in Lisa's angle of attack which left her pussy nearly pressing down against Derek's gagged mouth.

In the new position, Lisa found the heat from underneath her felt quite nice. Derek's panicked breaths tickled her bare pussy as he worked hard to breath, her ass not quite suffocating him as before.

Regardless of whether it was her son underneath her or not, Lisa couldn't deny the pleasure the sensation produced within her.

But she quickly put the feeling aside and found herself focused once more on the task at hand; Derek must be made to obey.

"You think not being able to breath is the only trick I have up my sleeve? Sweetheart, I've got

much worse

in store for you. You should have just listened to your mother..."