Chapter One

 

It all began quite benignly, in retrospect. David Randolph was born to a rather prosperous couple who had longed for a fourth child for many years and felt quite blessed to have a baby in their early forties. He never guessed that part of the reason his parents kept trying after three sons was that they secretly hoped for a daughter. Well, to put it more accurately, his Mother had felt more than a bit overwhelmed by the masculine energy of her energetic outgoing husband. His three older sons all seemed to be cast from the same mold as their Dad. That handsome alpha male moonlighted as a Karate instructor in the evenings after working hard all day in his thriving independent stock brokerage. Even worse, from David's Mother's much more fragile perspective, her energetic husband insisted on sex every night after his long days. When her fourth child after a five-year hiatus turned out to be yet another boy, she put her foot down and demanded separate bedrooms in their large house.

The ensuing marital discord and eventual separation and divorce meant that David never remembered living with both of his parents. When they parted ways as their youngest was entering kindergarten, the older kids were given a choice about who would be their primary custodial parent. This was at their Father's insistence, as he rightly suspected his older boys, who were all tournament Karate fighters, would opt for his own masculinized environment over their Mother's more sedate home. She well knew that fighting him was always a losing battle, and accepted his generous financial settlement in exchange for avoiding a custody brouhaha. As a result, David grew up most of his childhood as an only child in a radically more feminine circumstance than his brothers.

Looking back, all who knew the family agreed that all of the boys inherited their Fathers ADHD tendency. The old man had managed it intuitively all his life by exercising like a demon and subsisting on only a few hours of sleep each night. Once she and her youngest moved a few blocks away, Mrs. Randolph oversaw a much more low-key household. She got a job working from home as a technical writer for high tech firms and demanded a silent environment so she could concentrate on her writing (and finally smoke her cigarettes in peace). David learned from earliest memory that his beloved Mother was a fragile being compared to his robust Father, and he worked as hard as he could to please her. Because if he didn't, his poor backside was certain to be quite sore for the next day or two.

Spankings had not been a part of the family life before the divorce. This was because Mr. Randolph had himself been the recipient of frequent corporal punishment as a child as was the case for many fellow ADHD sufferers of his generation. Hyperactive and inattentive kids in that era were simply regarded as rebellious. And that was often regarded as something to be extirpated via the application of painful correction to the miscreant's rear end. As a result, when his own kids came along, their Father decreed that a punitive hand was never to be raised against his sons. The fact that their Mother had a different idea didn't even come up. And once the family separated, David was not about to get his dear fragile Mother in trouble with her domineering ex-husband.

So our hero was quite surprised once he and his beautiful but troubled Mom settled into their small bungalow. When he misbehaved as most five year old boys are prone to do, something new and unpleasant happened. His beloved Mother got very serious and ordered him into her bathroom, where he usually was forbidden to go. She sat herself down on the armless vanity chair there and ordered him to bend over her lap. He didn't know what this meant, and was surprised when her cool hands slipped under the waistband of his Levi's and pulled them down around his knees. He was even more shocked when she then did likewise to his jockey shorts, leaving his bottom quite bared.

But most stunning of all was what happened next. She took his right hand and held it pinioned against the small of his back with her left hand while her right one took up her hairbrush from the vanity top where it resided. Then she intoned in a cold but somehow passionate voice that he didn't recognize,

"From now on, my naughty young man, when you misbehave, you will be spanked. It will be done on your bare bottom so I can be sure not to bruise you, since that would be abuse. I would have done this to all of your brothers too if your Father had permitted it, and they probably would have been better for it. But this is my house now and we will live by my rules. I will spank you until I am convinced you have gotten the message. After which you will stand in the corner with your bare bottom on display while you think about how to be a better boy. Once your corner time is done, all will be forgiven and we will hug and go on as usual. If your Father finds out about this he will no doubt use his money and power to take you away from me. So if you want to keep living with me, I'd recommend you keep this to yourself as our little secret."

David did not know what to think about this. But he certainly didn't want to live with his rambunctious brothers who all delighted in bullying him with their martial arts skills when Father wasn't around. So no matter what, he vowed to keep mum. In any case, his mind was soon brought to a far sharper focus than his ADHD brain usually permitted on the intersection between hard wood and soft buttock flesh. His Mother spanked hard and methodically, alternating sides of his squirming nates as his cries and tears soon filled the bathroom. He begged and pleaded for her to stop, even for a moment, but she was implacable. The hind end pain she built in his poor bottom cheeks was unlike anything he'd known and by the end he would have done anything to avoid it. But she seemed to be lost in some kind of trance and until the hundredth blow (as he later figured out to be her standard dose of rear end pain) nothing would get through to her.

He was still sobbing when she picked him up and carried him to the corner of the bathroom where he was stood facing the wall and ordered not to rub his burning nether moons under threat of a repeat dose. She then brushed her long rich auburn hair as she sat and smoked her cigarette and watched him for the ten minutes she prescribed for post-punishment contemplation. Only then was he allowed to pull up his pants and get one of her wonderful hugs as she complimented him on his brave performance in her normal voice and promised him that all was forgiven.

The other thing that entered our hero's young life when he moved away from his Father and brothers involved his bottom too. It seemed his Mother had a belief from her own childhood that many of the problems that could develop in children might be headed off by ensuring that their bowels moved properly each day. So every evening after dinner, as she smoked her post-prandial cigarette he would be asked if he'd pooped that day. David would not have considered lying to his beloved Mom, so he would tell the truth. And if he hadn't, then into the same bathroom they would go. He would watch as she filled the enema bag with warm soapy water and hung it on the towel rack behind the commode. Then she would sit on its lid and once again lower his pants and underpants.

This time there was no need to hold his hand since he would not fight this treatment, which he learned to rather enjoy. His temperature would first be taken rectally to be sure he wasn't ill. The lubricated thermometer would slip into his bottom hole quite comfortably, if feeling a little funny. Then the same right hand that would wield the hairbrush so agonizingly would gently cup his bottom cheeks as she held the thermometer in place between her third and fourth fingers. Her hand felt lovely against his naked bottom, just as it did a few minutes later when she had slipped the narrow enema nozzle inside and released its contents to flow into his recalcitrant bowels. Once it was instilled, she would still gently hold his buttocks until he started to squirm with some urgency to release the pent-up fluids. Then she would help him up while still holding the nozzle in place so he wouldn't make a mess. After which she would raise the toilet seat cover and help him onto the seat while pulling out the nozzle. He would be left to expel the roiled liquids on his own since he was a big boy and didn't require assistance on the toilet. Once he was done, she would draw his usual nighttime bath and they would have a warm, pleasant evening.

All this was all quite confusing to our hero, who had no one too debrief it with since his adored Mother was his usual sole confidant. But however horrible the chastisement was, the making up was wonderful and all seemed miraculously right again in his small world. And in some ways, the threat of a repeat performance did enable him to concentrate better for a while. But his brain was recalcitrant, and within a week or two he always messed up again and ended up sobbing in the bathroom corner with a very sore bottom.

As for the enemas, over time he began to notice that when he was happily resting over her lap, his penis would start to have some kind of nice feelings as it rubbed slightly against her linen skirts. It also would get hard, which she seemed to find kind of funny and dismissed as usual behavior for that part of boys who always thought everything revolved around that organ. As he approached ten years old, that same reaction would happen during his spankings. This she didn't seem to find nearly so amusing, but he found quite disturbing.

All of this went on for the next five years during which he got a bit better at avoiding being spanked. David perhaps got it only once a month by the end, but still received enemas at least once a week. That end came quite suddenly when David was ten years old. His Mother had dropped him off at school and was driving home when she had a seizure and drove her car into a tree, killing her instantly. The autopsy revealed, as he later learned from his Father during a tirade against smoking, that she had advanced lung cancer and that her seizure had been caused by a brain metastasis. Her funeral was the hardest thing he had ever endured, worse than a thousand spankings. Our hero long thought that he would have gladly bared his bottom for punishment every single day if only he could have her back.

But reality was that David moved back into his old bedroom with his Father who had married a very nice younger woman who taught Aikido at the dojo. The whole family was totally into martial arts, though two of his brothers had already moved out to college. He was given no alternative but to go to the studio to take his Father and Step-Mother's classes each night and all day on the weekends. There was no use objecting, as that was what the family did and he was going to be a part of it all willy nilly. The truth was our David was a gentle soul, but also a very anxious to please one. Thus, rebellion didn't even cross his mind (especially after his Mother had so powerfully negatively reinforced that behavior on his naked behind). So he worked out at the gym every day as expected, as well as becoming a black belt in both Karate and Aikido just as everyone else in the family was. The one place he drew the line was fighting in tournaments. He suspected they all thought he was wimping out, but no one criticized him. And he still visited his Mother's grave with flowers every single Sunday no matter what.

Chapter Two

 

So off to college went young David. His Mother's painful attentions had turned him into a far better student than any of his brothers, who had barely qualified for local State colleges. His excellent grades and ability to hyper-focus on tests meant combined with the coolness factor of being a double black belt to gain him admission to any school he applied to. He chose Stanford because it was the furthest possible from his family's East coast home, though none of them seemed to realize this. But he did, and breathed a palpable sigh of relief when they drove off in their rental car after dropping him at his freshman dorm. 'Free at last', he thought, and vowed never to cross the threshold of a dojo for the rest of his life.

Stanford was an ideal place for our hero. His fellow students were diverse and interesting (with the exception of the legacy admits, whom he found obnoxious and entitled for the most part). The weather was fantastic, and he discovered the wonders of Ultimate Frisbee, a game that suited his athleticism and counter-cultural leanings perfectly. The fact that it was coed and seemed to attract the cutest liberal young women was also a definite plus. David was an unusually handsome young man, well built and an inch over six feet in height, with honey blonde hair he rapidly grew from his family's required buzz cut to a flowing mane of flaxen curls that offset his bright blue eyes perfectly.

David had always been a sensitive young man, and more inclined to hang out with girls than boys at school as a youngster. This of course earned him a target on his back for bullies. But by the time he was twelve his martial arts prowess made him impermeable to even the toughest childish assailants. His Mother had long prepared him to be the ideal companion that his Father wasn't. She taught him to recognize and talk about feelings (except, of course, any bad ones about her) and to listen to her woes sympathetically. She also violated yet another TMI kind of boundary by openly discussing her dissatisfaction with her sex life with his Dad.

Our hero felt uneasy hearing about his Father's selfishness in bed. Nevertheless he took to heart his Mother's admonitions to always see to his partner's pleasure before seeking his own. He didn't exactly know what this meant by the time she died. But he'd heard it enough times that when he did begin learning about sex on the internet as a teenager he soon figured out that meant getting women off before himself. Once he started dating, his Stepmother had privately given him a copy of an amazing book. It was entitled 'Guide To Getting it On' and explained everything he needed to know in plain English. From then on, the combination of his good looks with his metrosexual manner made him an absolute rock star among girls at his high school. This led to lots of sexual experience in which his ability to hyperfocus (as is true of a subgroup of ADHD sufferers) made him the consummate lover. Especially when compared to his benighted peers.

These factors made our hero at least as popular among the coeds at Stanford as he had been in high school. He had learned from his Mother never to press a woman for sex. It was his rule to always wait until his partner made each move towards greater intimacy before forging ahead. This lack of assertiveness made many women (and not a few men, many of them gay) wonder about his own sexuality, since his feminized persona did indeed ping many peoples' gaydar. But no woman he had ever slept with doubted David's heterosexuality for a moment. And further, not one of them ever failed to want more once they had experienced his intense focus on their pleasure.

This particularly manifested in our hero's fascination for giving oral sex. There was something about immersing his entire sensorium in a woman's genitalia that endlessly captivated him. In fact, he never went out twice with a girl who was uncomfortable receiving cunnilingus. When asked, he would admit that if given the choice between eating someone out and fucking her in any orifice, he would opt for the former every single time. There was something about the intricacies of female erotic anatomy and responses that David found endlessly fascinating. And he loved the taste and smell and look as well as the feel of a woman's pussy, whether full-bushed or waxed or lasered.

He regarded it as his goal in life to give every partner as many orgasms as she wanted. David only welcomed attention to his own body and cock when his lovers insisted. Which they most often did, since he had a solid eight-inch erection whose functions he could manage better than the vast majority of men. He seldom lost a hard on, and could control his own orgasm quite well because of his high level of attunement to his own body. Our hero had learned that self-awareness was the key to not coming too fast no matter how turned on he was. If he was getting closer to his orgasmic threshold than he wanted, he would slow down and focus on her pleasure until his own was not so imminent.

The downside with being such an ideal partner was that no one ever wanted to break up with David. Which was not the case for him in reverse. It seemed that he could maintain his ardor for each new partner for a few weeks or even months. But inevitably his attraction would wane and his lovers would sense this and start getting desperate to find some way to hold onto this apparently perfect lover. Then he would have to have the 'it's not you, it's me' talk, always leaving yet another attractive young woman in tears. So the move to Stanford was a relief because he had no reputation as a heartbreaker there. As well, the sample size of attractive young ladies was far larger than his high school. Perhaps, he hoped, he could fly under the radar for longer than he had before moving west.

And indeed this worked out well at first. The sexual culture in his class was much more casual than it had been at his high school. People seemed perfectly comfortable swiping right on their phones and hooking up with a stranger within minutes. Expectations for any kind of longer commitment were at most hinted at, but more often suppressed to avoid the risk of manifesting any uncool neediness. But even in that atmosphere, no girl he encountered had ever had sex nearly as gratifying as David insisted on providing in his never-ending quest to be pleasing to women (at least in the short run). This always seemed to lead to avid repeat customers, who would gradually or suddenly realize what a gem they had encountered. They would start wanting more, and he would try manfully to give it. He truly loved listening skillfully and empathically to their feelings and doubts, unwittingly bonding them even tighter to him. And then his own unconscious defenses would be triggered and he would find his ardor evaporating until they would notice. This would of course most often trigger their anxiety and prompt them to fall into just the sort of manipulative behaviors most likely turn him off even further. The girls would always have to end it since our hero could never see himself as doing harm to women. He would stay sweetly distant behind his martial arts schooled equanimity until they couldn't stand it any longer and would blow out of there.

This happened with literally a dozen lovely and talented young ladies over the four years it took our hero to complete his psychology degree. By the end he could not collude with his own denial any longer. He began to seriously consider the likelihood that he himself was and had a problem in romantic relationships. David mentioned this to a female buddy who had long since accepted that she was not a potential partner for him because of her relative plainness in appearance compared to his usual parade of gorgeous girlfriends. She suggested that they do some shrooms together in a nearby redwood forest park and see what came up in that altered state. And indeed, in our hero's drug-fueled deep conversation with his perceptive friend, he realized with true dismay what a subtly but profoundly harmful way he had treated his girlfriends from the beginning.

This breakthrough shook David to his core.