Preface

 

In 1253, five years after the bubonic plague outbreak in Florence, Italy in 1248, Giovanni Bocaccio published 'The Decameron'. Written in vernacular Italian rather than the Latin most books were published in at the time, it was an unprecedented glimpse into the steamy lives of three young men and seven young women quarantined against the plague on a posh country estate. While they told a hundred stories over the ten days of their isolation, we will limit ourselves to a small fraction of that number in our own illness-isolated cohort of the same gender makeup. May these tales spice up your own pandemic isolation!

Chapter One

Jason: The Naughty Boy

 

Jason Lindsay was a very frustrated young man. That state was not at all something he was used to for the vast majority of his twenty-one years on Earth. An unusually auspicious roll of the genetic dice brought him into the world in as advantaged a state as anyone could reasonably hope for as far as brains, looks, charm, and athletic ability. He was a solid six feet two inches of lean muscularity with wavy blonde hair and a classically handsome face highlighted by piercing blue eyes that caused young women to swoon on a regular basis. Our hero was born an only child to two highly successful and driven parents who saw no reason for their son to be anything less than exceptional in all of his pursuits. The precocious and anxious-to-please child learned from earliest memory that he had better make his best possible effort to meet the expectations most especially of his Mother. She was in direct charge of him since his father was usually travelling internationally to foster his high-tech business empire. For if Mommy was displeased, her devoted son knew that his poor bottom was going to suffer the consequences.

Mommy was a firm believer, based on her own experiences with strict parents who spared no rod and spoiled no children, that childish misbehavior needed to be nipped in the bud by the careful application of painful stimuli to bared and squirming buttocks. Her parents passed on to her their conviction that this part of the human anatomy was ideally designed to receive punitive attention without risking harm to the unhappy recipient. This plan had worked to enable her grow into a stunningly beautiful woman, to reach the top of her profession as an intellectual property lawyer and to marry a handsome wealthy catch. So she saw no reason why it would have any less success with her adoring son. For Jason truly did worship his lovely blonde Mother, whose glowing smile of approval felt as delicious to him as her scowl of disappointment felt like the end of the world. And indeed, for a toddler and small boy the consequences of her disapproval did feel like he was cast into painful and shameful misery by her spankings.

Receiving a spanking was a carefully ritualized occasion for our hero during his childhood, just as it had been for both of his parents. They believed that punitive discipline should never be delivered by an angry disciplinarian, since that emotion could cause harm by fostering the deliverer of corporal punishment to be out of control. So when Jason misbehaved as all spirited boys are wont to do, he would be ordered to go to his room and think about what he had done for an unendurable half of an hour while he got more anxious as his Mother calmed down. Then stern but no longer exasperated Mommy would come into his spotlessly kept bedroom carrying the hated hairbrush she used each night to brush out her long blonde mane (which was almost always pinned up in a severe chignon emphasizing her swan-like neck). She had often explained to her trembling son that he was to be spanked with the very same implement her own strict Mother had used on Mommy's own backside when she was a naughty girl. Somehow the frightened boy failed to find this connection very comforting given what he knew was coming.

After Mommy had seated herself on his armless desk chair, the tearful boy would be made to stand in front of her while she reviewed the nature and wrongness of his misbehavior. Once she was clear that he understood and was regretful, she would place on the desk behind her the hardwood brush, which had been ominously tapping her left palm during her monologue and his sparse and hopeless replies. Then her cool lovely hands would reach out and unbuckle his belt and lower his pants and underwear to his knees. This always terribly embarrassed him as his naked genitals would be starkly on display. She would always sense this and often rub it in by remarking,

"It's embarrassing to have your naked bottom and crotch bared, isn't it my naughty young man? That's part of your punishment which you have earned by disobeying your parents who love and provide for you. And of course, you must be spanked on your bare bottom so Mommy can be sure to have administered just the right amount of corrective medicine while being certain not to harm to your bottom cheeks!"

Jason's pants and underpants were left around his knees to prevent kicking and ensure that his usual lively response to being spanked would not spoil his tormentress' aim. She would then gently but firmly guide his naked bottom over her primly skirted lap and order him to put his right arm behind his back. There she would secure his wrist pinned against the small of his back with her left hand to keep him firmly held in place. This was necessary to keep her aim true as he bucked and squirmed his way through the ensuing ordeal. As well, this firm grip prevented his errant hand from interfering with the proceedings as it very much would have wished. Then the hated hairbrush would be taken up and its hard wooden back vigorously applied to our hero's quivering clenching nates in time to a staccato lecture about the wages of sin.

Mommy believed that a miscreant needed to be reduced to helpless tears in order for a spanking to deliver its intended lesson most thoroughly. She felt such an outcome required at least a hundred burning kisses of unyielding wood on all-too-vulnerable buttock flesh. Once the desired effect had been achieved, which she could tell by the cessation of her subject's struggles indicating total submission to her dominion over his bottom, his torment would end. The sobbing boy would be helped to stand and made to walk in hobbled steps to the corner of his room. There he would spend ten minutes with his throbbing rear end on display as his Mommy looked on triumphantly. Then he would be allowed to pull up his pants and receive a perfunctory hug before being left to do his homework.

These sessions seemed to happen about once a week until Jason was about ten years old, after which his efforts to avoid pissing Mommy off seemed to reduce them to once a month. Unfortunately, when he was about thirteen she noticed that his pubescent penis began to react to his spankings by becoming partially erect. This prompted uncomfortable inquiries into his masturbatory and fantasy lives, of which she rather violently disapproved. He had never mastered the art of successfully lying to her, so he was soon back to weekly painful trips of his much larger body over her firm lap to be chastised for his inability to manage his nascent sexuality as she saw fit. This led to what was for Jason a most uncomfortable standoff in which he stubbornly refused to refrain from what she termed 'self-abuse', and she delivered a hundred fearsome spanks to his more and more manly buttocks every Sunday evening.

What Mommy didn't know, though one wonders if on some level she suspected it, was that Jason's spankings had formed a cornerstone of his developing sexuality. Because she was not an affectionate Mother, these weekly trips over her lap and the subsequent perfunctory hug were his only physical contact with her most weeks. As developmental psychologists long ago learned, a child learns to accept whatever he is given by his parents as normal. Over time, even painful attention from an adored parent becomes desirable, even precious, if it is the only game in town. So it was hardly surprising when adolescent Jason began to eroticize his spankings by his severely beautiful Mommy whom all of his classmates and teammates regarded to be their favorite MILF. This rather inevitably led to one Sunday when he developed a massive erection squirming against Mommy's hard lap for a hundred painful kisses of adamantine wood against tender buttock flesh. She had vaguely detected this situation while lost in her usual punitive frenzy as she tried yet again to burn the horrid male sexuality out of her handsome son's poor bottom. But instead, when she stood him up as usual, bobbing insouciantly right before her eyes was the biggest hard-on she had ever seen. An uncharacteristically flustered Mommy stammered before stumbling out of Jason's bedroom for the last time,

"You're getting too old to be spanked..."

The teenager was left in his own welter of conflicted feelings, predominated by deep shame at the reality that he was more turned on by his weekly trips over his attractive Mommy's lap than he was chastened by them. But his aching erection demanded some sort of attention since it seemed totally disinclined to depart on its own. So just as he had for every night for several years, Jason jerked himself off to the arresting image of his beautiful blonde Mommy spanking his naked buttocks until he showered his chest with a copious spend. And although his strict parent never laid another violent hand on him from that day forward, that image continued to dominate his fantasy life to the beginning of our tale.

Just as Mommy had been a very successful ballerina in her own girlhood and Daddy had been a national class intercollegiate wrestler, their privileged son was expected to excel athletically as well as academically. He was allowed to choose martial arts and by the time he entered high school he had earned black belts in both karate and aikido. As a freshman the football coach saw infinite potential in the handsome and well-behaved young man and recruited him to play safety on defense, a position that could take ideal advantage of his speed and toughness. By the time Jason was a senior he was considered a five-star recruit nationally, and was delighted to accept a full scholarship to Stanford. His play on that team continued to be stellar, and by his senior year he was considered to be a low round draft pick for some lucky NFL coach. Then an illegal chop block destroyed his left knee and required a full joint replacement, effectively ending his dreams of playing professionally.

Life at Stanford had been eye-opening to the handsome, well-behaved young man. He had dated in high school and gladly lost his virginity to a lovely girl a year older than him when he was a junior. Mommy was of course aware of this and frostily disapproving of another female having such an influential role in her only son's life. But after her spankings ceased, she correctly surmised that her offspring was increasingly willing to push back against her efforts to control him. A few discussions with a counsellor convinced her that trying to demand his celibacy was a losing battle. As long as he was well-behaved and got good grades that she was advised it was better to back off from efforts to control his sex life. But the emotional withdrawal that was Mommy's only avenue of expressing her disapproval of his erotic growth weighed heavily on Jason, who had steadfastly adored her whether she was spanking him or not. He found solace in friendships with girls who appreciated his emotional depth while maneuvering for his erotic interest. By the end of high school our hero felt confident in his ability to either befriend or seduce any woman he fancied (including his 25-year-old aikido instructor who gave him as top-notch teaching in bed as she did on the mat). But no matter how attentive a friend or lover he could be, all of his coterie of adoring females felt that a certain part of him was forever kept from them. This mystery only made him more desirable, as each of them strove to be the woman whose love could unlock his powerful defenses.

This situation persisted at Stanford, where Jason's precocious stardom on the football team made him a particularly high value target for horny coeds. He completely avoided the hookup scene, choosing to stick to his established pattern of befriending girls as his lead in to seducing them. But none ever got past the stage of friends with benefits, to their growing frustration. Of course, the benefits were so worthwhile, given his good looks, skill at conversation, and well-trained sexual expertise, that almost none of them ever dumped him before things just drifted away. And not a single one of his many lovers ever suspected that every single orgasm he ever had (whether self-induced or communal) required him to imagine his imperious Mommy blistering his buttocks with her infernal hairbrush.

Jason's knee injury was the crowning debacle in a senior year fraught with tragedy. For a few months prior his parents had been on a small plane taking them to an upscale safari resort in Kenya when a sudden downdraft caused a crash that killed all aboard. The newly orphaned young man felt stunned but not nearly as undone as he or all of his friends thought he should be. After all, his Father had been virtually absent his whole childhood, and his judgmental Mommy had withdrawn ever since he was in his early teens. So it was not as though he had lost any relationship of true closeness like he had learned to have with his female friends and lovers. And to be sure, becoming the sole inheritor of over 50 million dollars rather softened any blow he might have felt from their deaths. And yet...a part of him felt strangely empty and guilty that their passing should affect him so superficially.

By his senior year, our hero had paid an outrageous amount for an upscale condominium in downtown Palo Alto where he had hoped to establish a love nest for the many attractive young ladies glad of his company. His knee injury and subsequent joint replacement surgery rather derailed this plan as his time beyond that needed for the courses to complete his Psychology major was now invested in rehab. He became a frequent user of the lap pool next to his condo as well as the first-rate gym in the basement of the condominium complex. It was in these two venues that he befriended the people who opened the doorway into our story.