The Spanking of Widow Conway Ch. 01

It had probably been a good fifty years since Helen Conway could say she slept in until 8 o'clock in the morning. Retirement unfortunately had a way of doing that to a person.

For years she'd wake up long before the Sun to help with the chores around the family farm and get her Husband fed before getting herself ready for her forty-year job as a teacher in the area. Ever since her retirement two and a half years earlier however, everything in Helen's life had seemingly gone haywire.

Her husband Bill had died of a massive heart attack just before Christmas the year before last. After the normal mourning process, Helen's ornery pride told her she could still run the farm. It didn't take long for her to realize she'd bitten off more than she could chew. Thankfully Helen's three grown kids had convinced her to sell off most of the land and equipment, leaving her with a few dairy cows and hogs she could tend to herself. Frugal to a fault, money was thankfully never going to be a concern, but with all that free time on her hands, and without the pull of a daily challenge, rust quickly began taking its toll, mentally and physically, on the 65 year old widow.

Even though the daily chores helped Helen keep a spiritual connection to her departed Husband, it wasn't long before her frail and aging body became overmatched. Within a year she'd sold off the remaining animals, and with all three of her children and six grandchildren living out of state, the walls of Helen's century old farmhouse began to close in on her.

Having been a dedicated wife, mother and teacher all those years, hobbies had been something of an afterthought. Considering the closest neighbor was over a half mile away, it gradually came to feel as if she was existing rather than living.

Helen Conway needed a new challenge and she needed it quick. Thankfully the downturn in the nation's economy, in a strange way, provided Helen with that saving grace.

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28 year old Jess Tuttle was coming off the Summer from Hell. In late June his Wife of six years told him she was having an affair and was ready to file for divorce. Unfortunately, given the couple's financial situation, that wasn't going to happen until they could sell their house, and that wasn't going to be easy considering the state of the economy. The fact that his Wife's lover was also married and in a similar boat with his Wife created an air of perpetual purgatory around the Tuttle household. The strain of that uncertainty was also beginning to affect their two kids, five year old Justin and three year old Trina.

Professionally things weren't much better for Jess. Getting ready to start his fifth year as an 8th grade science teacher at the local middle school, the downturn in the State's budget had facilitated the need to close several schools, one of which was the other middle school in the county, meaning Jess' class size for the upcoming year was about to double even though his pay would stay the same given the statewide wage freeze.

Several teachers from the school being closed had agreed to come aboard to fill some gaps, but none of them in the science department. Two weeks before the start of classes, Jess got the phone call that the school board had hired a handful of retired teachers to work part-time as teacher aides, one of which was a 65 year old veteren of the area classrooms named Helen Conway.

Jess had never met Helen, but instantly detested the thought on several levels. While he was sure the older woman would take some of his load off trying to keep the extra students inline three days a week, considering what he was going through with his Wife, the female species wasn't very high on his Christmas list at the moment, and the last thing he needed was what he was sure was an uppity, know-it-all dinosaur coming out of retirement and taking over his classroom.

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From the first day of classes, even for someone as pessimistic as Jess

was at that point in his life, he had to admit Helen's presense had been a benefit. For starters, Jess didn't realize the magnitude of having to deal with five classes each day with 30 plus students in them. It was akin to teaching in a large urban inner city with the swollen class sizes instead of the normal rural Montana classes he'd grown accustomed to.

For her part, Helen had also been the complete opposite of everything Jess had dreaded when first told about the idea. For a teacher that had full control of a classroom for four full decades, she'd shown an inspiring amount of grace allowing a young teacher like Jess to pilot the ship. Even though Helen had shown comfort sliding into the role as 'teacher's aide', Jess found himself marvaling each day at the older woman's ability to hold the attention, and respect, of the tide of 12 and 13 year olds that washed in and out of their room, often times doing it with a mere gesture, nod of her head or measured edict.

The more he got to know Helen in between classes and after school, the more he came to understand just how important it was for her to be back to work as well. As time went on sharing a classroom with Ms. Conway, Jess discovered as series of life lessons, both professionally and otherwise, that he would use for years to come.

By the Spring of their first year as teaching partners, Jess had even allowed Helen a chance to babysit his two kids on occassion when his Wife was away, shacked up with her lover. The environment around the Tuttle house had grown so toxic after the holidays, by the time the Winter started to break, allowing his Son and Daughter to run around and enjoy the expanse of Helen's farm seemed to give the kids a new lease on life, and with their grandparents living so far away, someone in a crazy way to fill that role as well.

Naturally, the time spent away from school built a fair amount of trust and camaraderie between Helen and Jess in the classroom also. Helen provided a mentor role Jess had never quite had, and in return he seemed to provide Helen with a youthful vitality she'd been yearning for without really even knowing it.

It was still two months however before the depth of their budding relationship became apparent.

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It all started to come to the surface one Sunday afternoon in late April when Jess had brought his two kids over to Helen's after church. Jess' Wife was off on another one of her weekend trysts with her Boyfriend and he decided since the weather was starting to get nice to let his Son do some fishing on the small lake Helen owned while she entertained his Daughter with some crafts. Unfortunately, five year old Jacob Tuttle had started asking some tough questions about the comings and goings of his Mom.

Put in that difficult spot, Jess did his best to be as forthright as he could with his Son without completely throwing the boy's Mother under the bus. The rage, hurt and helplessness continuing to boil under Jess' skin the more his Son went on and on, he finally told Jacob to drop it, that they'd talk about it when they got home.

Not liking the answer his Father gave him, still in his church clothes, young Jacob proceeded to go on a tirade spewing a litany of not so pretty words he'd learned from other kids since starting Kindergarten that year, none of which he truly knew the meaning of. The fact that they seemed to push his Father's buttons was good enough for the time being.

Even though Jacob had been restless all morning in church, Jess hoped the promise of taking him fishing would have made the boy behave. Sadly for all involved, the young man's need to vent about the anxiousness he was feeling trumped any desire to reel in a bass or two that afternoon.

Fed up, Jess threatened Jacob twice with a spanking and when his Son didn't take the hint, Jess was left with no option but to follow through with his threat even though he was at Helen's house.

A Mother of three and Grandmother of several more, Helen Conway had been raised in the 'old school' so she didn't have a problem in the least with Jess' course of action, in fact if Jacob had been one of her kids, she would have probably done it sooner.

Watching Jess disappear with his Son to one of the backrooms of Helen's house, Helen quickly Sheppard Trina towards the kitchen to make a very awkward situation a little less so.

Having spent a good many years as a teacher when corporal punishment was an acceptable part of the schooling process, Helen frankly hated to see those days go. Unlike many of her contemporaries that never did learn to adapt, thankfully she'd developed other techniques to keep the kids in line, but to her dying day she was always going to be a 'spare the rod/spoil the child' type of person.

Making small talk with Trina at the kitchen table, doing her best to keep the girl's attention diverted from the goings on in the spare room down the hall, Helen got the vague but certain sense from the girl this wasn't the first spanking her older Brother had gotten recently.

The echoes of several flesh on flesh slaps billowed through the old creaky house as Helen cut a slice of apple pie for herself and the three year old girl. Each slap was quickly followed by Jacob's voice rising in pitch and straining urgency that he was sorry for his attitude and choice of words. Nudging Trina to get her to eat her piece of pie as the spanking continued, Helen finally took a deep breath and tried collecting herself when things fell silent in the other room.

What she saw when Jacob walked back into the kitchen was a changed young man. While the still moist trail of his tears covered both his beet red cheeks, Helen was certain it would be a while before another curse word slipped from Jacob's trembling lips.

"I'm sorry I had to do that," Jess apologetically mouthed to Helen when he took the slice of pie she handed him.

"You did what you had to do," the older woman chimed back with clear understanding and affirmation.

With his slice of apple pie sitting in front of him, eventually even Jacob put his fork through the golden crust and gooey center before taking a hulking bite, signaling all would be well for the rest of the day.

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It was a few weeks later when the nights were first getting warm enough for a cold natured person like Helen to sleep with her windows open. It was well after Midnight and a gentle breeze was flapping the bedroom curtains like two lazy flags.

Curled up and sleeping in somewhat of a fetal position on her left side beneath a sheet and light blanket, it looked as if her eyeballs were two spastic marbles racing behind her closed eyelids. Her left hand cinched tightly into the pillow under her head, Helen's right began a blind crawl down the length of her body as if it had a mind of its own. The exhales of wind swooping through the screen of the window every few seconds, the sleeping woman's feet started to rut into the mattress below, as if trying to gain a foothold of some sort.

The images behind Helen's wall of sleep were cloudy at best, but the feelings tingling through every nerve ending in her body were crystal clear.

For whatever reason, Helen's most virulent sensations of arousal came when she was asleep. Having been reared in a home by very strict and religious parents, any discussions of a sexual nature were few and far between. Even after she married, it had been to a man from a very similar background as hers, and even though they did have three kids together, the topic of lust rarely came up.

From doing her chores around the farm first thing every morning, to

teaching school, to raising her children along with everything else she was expected to do as a wife and homemaker, exploring her sensuous side wasn't something Helen really had never preoccupied herself with.

It was when she was asleep that many of those natural urges and longings would subconsciously begin to percolate through her loins and bleed to the surface. Many a night the slickness of her arousal would leech from her pussy, soaking the crotch of her underwear before drizzling down the insides of her thighs.

That Spring night in bed was one such occasion. Wedging her right hand between her upper thighs as she snored away, Helen lips parted and a low, rolling 'oohhhh' sound began seeping from her gut when she grazed her fingertips across the puffy folds of her labia. In her dream, Helen felt as if she was laying naked in a lush green field, her arms and legs outstretched as if in acceptance of a blinding white light that descended down upon her. Every molecule in Helen's body pounded as the heat from that imaginary orb steadily engulfed her. Dreaming she was overcome and helpless, once she was in the safety of the heavenly aura, Helen felt safe unleashing a lifetime's worth of repressed want.

It was a frequent course of Helen's dreams, almost a liberating mechanism in a way, allowing her to sample many of the base instincts she'd hidden away in her mental catalogues for the previous six decades.

Flaring her fingers through her pussy as she bathed in the heat of her dreamscape, the pounding in every nerve ending in her body gradually became more narrowed and focused until it was singularly concentrated on the rounded part of her left asscheek. Letting out an audible groan beneath the sheet each time she imagined a large hand coming down on her behind, Helen Conway's clitoris grew to the size of a throbbing pea between her fingers as she sleepily masturbated herself to orgasm.

The rumble of an approaching storm stirred her awake a few minutes later. Shaking the cobwebs out of her eyes as she saw 2:43 on her alarm clock, Helen pulled her covers back and rolled out of bed to go and put her bedroom window down after hearing another grinding echo of thunder. The instant the older woman's feet hit the floor, she nearly felt herself toppling over from the post orgasmic tremors still racing up and down her legs. Holding on to the bed frame then the nightstand as she negotiated her way through the dark, Helen finally put her hands on the window sill and looked out to see the crackle of the approaching lightning in the western sky.

Almost like a teenager having wet dreams, Helen had grown accustomed to busting her nut, so to speak, in the middle of the night. Feeling how raw and hard her pussy continued the throb as she braced herself against the window, Helen knew she'd just woken up from an especially potent fantasy. Feeling the greasy trail remaining on her fingers as she rubbed them together, Helen knew she normally remembered very little about the dreams that had haunted her sleep. This time however things were much different.

Standing there in front of the window, allowing the soothing cool and electrically charged breeze to sweep through her night shirt, Helen could remember several details of the dream sequence that had just played out in her head.

Eventually closing the window in preparation for the oncoming storm, Helen shuddered from the potency of those leftover images, seared forever into her brain. Crawling back into bed, for a few minutes Helen laid there on top of the covers, her eyes closed as she visually re-lived what she could remember from the previous dream, the fingers of her musky right hand once again buried and spinning in the same exact spot it had been only minutes earlier.

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In most cases after Helen had partaken in a little selfish overnight release, she woke up the following morning feeling refreshed, with a clear and unburdened conscience. When she opened her eyes that next morning however, Helen found herself fidgety and far from rested. The fantasy she'd allowed herself to have (twice) during the night had somehow hit uncomfortably close to home.

Not only did Helen have to get her still groggy body out of bed and ready to head to school, she also had the weight of her guilty conscience, knowing she would have to face the object of her sickly perverted late night dream when she got there.

The fact that a 28 year old man had somehow become the centerpiece of one of Helen Conway's fantasies frightened the 65 year old widow to no end. The more she tried to convince herself in the shower that it was only a dream and that it meant absolutely nothing, the more she found it difficult to hold the slick bar of soap in her trembling hands.

Shame was a trait Helen possessed in spades, thus she felt herself starting to blush each and every time she tried to make eye contact with Jess that day in class. Why she felt the depth of guilt over her decadent and devious fantasies of the night before would take a little more soul searching to put her finger on. Jess had overtly done nothing to set those feelings in motion, yet there he was at the center of the breach of her emotional dam.

Thankfully there had been enough obstacles with the kids' behavior that day to divert Helen's focus from her inner demons. With at least one discipline issue with a kid each class, Helen and Jess had their hands full just keeping everyone on task.

"No way either one of us could do this on our own," Helen found herself commenting to Jess between one of the class changes.

"I know I couldn't with classes this size," he sighed. "They don't have any fear these days...none at home ..and naturally none here either."

"Makes me wish I was around teaching when corporal punishment was OK," Jess offhandedly laughed. "If you could make an example out of the biggest problem, most of the little ones would go away as well."

"Yeah..I was around for awhile back then," Helen nodded, feeling herself drawn to her much younger partner yet again.

"Uh...speaking of which...I did want to apologize once again for the way Jacob acted at your use a few Sundays back," Jess said with sober softness a few seconds later after the topic of spanking misbehaving children came up.

"No apology necessary Jess," Helen smiled reaffirmingly. "We didn't hear a negative peep out of the boy for the rest of the day, did we?"

Jess shook his head in agreement.

"That sort of thing could do wonders in the classroom," Helen added. "Its a shame we've churned out so many lawyers to keep it from happening."

The two shared a quick laugh as the next class trickled in. Once again those strange butterflies had returned to Helen's stomach, and each step she took for the rest of the day was seemingly on numb and itchy feet.

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Not the type for psycho-analysis, Helen Conway would have never found herself on a shrink's sofa. If she had however, several interesting things may have been divined.

As stated earlier, she was raised in a very strict family. Physical discipline was commonplace in the household for Helen and her five siblings. Of the six, she was probably the most well behaved, but Helen did get her fair share of visits on her Father's lap for backtalk or not following through with her chores.

The worst of those whippings by far came when Helen was 15. Having lied about what she'd planned on doing when she went into town with friends one afternoon, young Helen knew she was in deep trouble when she got caught by the local cops in a parked car with an 18 year old boy. All Hell seemed to rain down on Helen after she was dropped off at her house by the local Sheriff. She never saw that boy again, but she did see stars each time she attempted to sit down for the next couple of days.

In hindsight, Helen looked back with great admiration for her Father for the way he'd handled that situation. The last thing a girl her age needed was gaining a 'reputation' around town, much less the potential for pregnancy when she had so much of her life left in front of her. Her parents had big dreams for her and they knew getting involved in such adult things before she was one herself could only derail everything she was working towards.