Chapter One

 

In moments of grandiosity (which are not all that infrequent), I like to imagine myself as a modern male version of the Renaissance Venetian courtesans. Historians describe them as women of great beauty, to be sure, and undoubted prowess in the realm of the boudoir. But they were prized more for their minds and the careful study they made of deeply gratifying the men they served on every level from base to exalted. These paragons of prostitution, in close parallel to the geisha of medieval Japan, were reputed to employ their keen intelligences to sniff out things a man needed that even he might never have considered. Then their ultimate art was to gratify those needs, both psychological and carnal, with consummate skill and panache. Achieving that goal with women is what I was brought up to do by my rather complicated Stepmother, rigorously trained to accomplish by my Mistress, and have adopted as my calling in life to my deepest core. This is my story, to the limits of my self-awareness: how I came to be the way I am, and how that plays out with the clients I so willingly serve with my body, mind, and soul.

I remember a cynical comedian saying, 'Oedipus, schmedipus, a boy oughta love his Mother!' Well, that certainly applied to me, and in spades, since my earliest memory. My Father was nominally around until he died when I was 21. But he remained throughout my life as a friendly but distant figure who was always too busy making truckloads of money in his arbitrage business to have much of a relationship to his only offspring. He provided me and my Mother with a very comfortable life and showed up vaguely for important celebrations. But his true passion was for his work, which left my beautiful Mom with a great deal of energy that had only one outlet, which was her cherished son. My few memories of her are all very idyllic, as if filmed through a light glaze of Vaseline on the camera lens (as film directors used to do when portraying romanticized scenes). But she must not have been entirely happy, or she wouldn't have been found dead of a lethal combination of booze and pills when I was 5 years old.

I dimly recall being looked after by a series of nannies for a couple of years after she died, all of whom were perfectly nice to me as far as I recall, but there was no change at all in my Father's absenteeism. And then he made up for all of his shortcomings by bringing me my stepmother, the lovely graceful Jeanne. For a lonely grieving 7 year old he could not have chosen a more wonderful Mom, the antithesis of the wicked stepmother in every way. She was beautiful, resembling Disney's Snow White in coloration and disposition, and cheerfully upbeat at any hour, day or night. Even better for a little boy hungry for female attention, she was very physically affectionate, constantly hugging and petting and caressing me whenever she was around me. I noticed that she shifted these attentions to my Father when he was around, but since that was seldom, it didn't bother me much. After all, once he was back at work, which he seemed to do about 18 hours a day, Mommy Jeanne was all mine. My only worry was that she would have some brat of a baby brother or sister, but fortunately that feared sharing of her love never came to pass.

What did happen was an almost blissful decade in which I had the most attentive and loving Mommy imaginable. I tried very hard to please her, both because it is my nature to do so, and because it seemed only fair since she was always going out of her way to take the best possible care of me. Of course, when my Father was around, his needs and desires would take precedence, as Mommy Jeanne explained to me. I felt some jealousy about this regular, if temporary, abandonment. But I kept these unpleasant feelings to myself, unless she wormed them out of me, as she could always do. Jeanne was so sensitive and attuned that she could inevitably tell when I was upset or grumpy. A few deft questions while she was cuddling and petting me and inevitably I would spill the beans and reveal what was actually going on with me. She was always kind and understanding even when my private thoughts were quite terrible, helping me to make sense of them. Once all was revealed and understood, she would say, somewhat cryptically,

"It's all right, Jake, I totally forgive you. We all have a dark side, including myself. When I was your age, I confessed everything to my own wonderful Mother, and she would help me to understand just as I try to help you. But things were different in the house I grew up in, and naughty behaviors and thoughts and feelings were handled with more than just understanding. My parents believed that God designed the human body with a perfect place to receive corrective attention from a loving disciplinarian. Your Father understands that quite well, but doesn't believe in corporal punishment of children. So you don't get to experience the benefits of paying that straightforward price for your wickedness and then knowing the relief that comes with enduring proper consequences for your sins and emerging cleansed and rehabilitated."

I knew she was referring to spanking, since I had friends and classmates who alluded to 'getting it' on their bottoms when they were bad. I had always been secretly fascinated with their stories, and perhaps even a bit envious of them for getting to have such a definitive relief from the guilt that we all felt for our inner naughtiness. But this issue got even more complicated when I was in my teens and my Dad and step-Mother were out for an evening and I was left alone at home. I was bored and feeling rebellious (and maybe a bit abandoned by her) so I decided to investigate their bedside table. What I found there was a trove of books about misbehaving men, young and old, being subjected to exactly that sort of treatment by their wives or lovers. Also in that drawer were an assortment of paddles and straps and dildos of varying sizes. It seemed that my distant and preoccupied Father was subjected to exactly the sort of treatment of his own backside that he denied mine.

This was quite a revelation to me, as you might imagine. Picturing my gorgeous step-Mother taking my large athletic Father over her lap and wielding an implement (I couldn't imagine her small feminine hands making much of an impression on his muscular buttocks) to chastise him caused a very troubling reaction between my legs. I had long since discovered that when my body responded that way I could use my hands to relieve the swelling, so to say, quite pleasurably. So I got my start then at annealing sexual pleasure to images of deserving bottoms being soundly spanked on a daily basis (actually, several times each day-remember, I was a teenaged boy) before my own backside had ever experienced a single spank.

Of course, like every young man of my generation who was not electronically impaired or isolated, I was well aware of the plethora of porn available to me just a click or two away. Given how close we were and how canny she was, Jeanne quickly sussed out my forays into the vast world of BDSM pornography. We had many a long and (for me, at least) uncomfortable conversation about the realities of that industry and what kind of exploitation consumers were tacitly endorsing when they clicked on a site. After I had left for college and it became apparent to us both in our nightly check in calls that I was going to persist in my disapproved explorations regardless of her disappointment, she took what she termed a 'harm reduction' tack. That took the form of guiding me to sites on which she was fairly certain the performers were genuine enthusiasts who were willingly subjecting their bottoms to the painful attentions that formed the heart of that genre. Only later did it occur to me to wonder how she knew so much about that world, as persistent readers will discover in a short while.

Having such a close relationship to my stepmother had many advantages for me as a sensitive boy who was attracted to girls from earliest memory. Starting in pre-school and kindergarten I was the sort of boy who always had a girlfriend, and who developed powerful crushes on the several pretty young teachers I had as a youngster. Jeanne always openly approved of these innocent liaisons, happily transporting me to play-dates at the homes of my latest platonic paramour or graciously hosting my female buddies when they came to my house to work on homework or just to hang out. She took obvious delight in debriefing my encounters with the objects of my many crushes (whether peers or teachers). And when I inevitably got my feelings hurt by fickle young ladies, she was always there to cuddle and comfort me in my sadness.

But in the main, her advice about the feminine mind enabled me to be far more successful with girls than any of my male peers. This fact, coupled with the social taboo in latency age boys against consorting with the enemy (namely girls or teachers or, worst of all, girl teachers) virtually ensured that I would be an obvious target for elementary school bullies. And once again, it was my dearest Jeanne who came to my rescue. She hired a private aikido teacher to work with me for several hours each Saturday and Sunday starting when I came home with my first black eye in third grade. Within weeks that tiny Japanese woman whom I saw throwing full-grown men all over her studio taught me moves that enabled me to nonviolently guide my untrained schoolyard assailants to the ground and hold them until they gave up and stopped bothering me. Needless to say, Sensei Fujiko immediately became the object of perhaps my greatest crush, and stayed that way for the ten years I studied with her while learning that most subtle of martial arts.

All this closeness to females of all ages also put me in touch, especially when I hit puberty, with what I soon learned to be my very powerful sex drive. Since by most accounts I was a good looking young man, you can imagine from the above that erotic temptation was bound to come my way both early and often. Jeanne seemed to especially delight in hearing about my sexual adventures in whatever level of detail I chose to share. She also was quite happy to give advice quite shamelessly about pleasing my girlfriends to whatever degree of specificity I felt comfortable asking for. Her frank education on how to satisfy women formed a solid foundation for the more specific formal erotic training I was to receive later on, to be revealed below in considerable detail. Of course, what was not only unmentionable but actually unthinkable (at least to a good boy like me) was how much I wished those experimentations were happening with my adored Jeanne.

But instead I had her stellar guidance in how to please girls my own age, both in and out of bed. She would happily prebrief and debrief my dates, always looking to enlighten me on what my girlfriends might be thinking and feeling to cause them to behave the ways they did, and how those motivations could be investigated towards greater understanding. And then as a present the summer I was heading off to Stanford she (well, actually, my father but totally at her behest) paid for me to get formal massage training at a sort of funky iconic California counter-culture retreat center tucked into the cliffs of Big Sur. This was of course the happy hunting ground for a horny young buck like myself, and I spent every spare minute when I wasn't learning massage in sampling the biddable young hippie girls only too happy for my company. My loving stepmother explained that every woman would adore a man who made it his mission to become intimate and healing with every muscle, bone, tendon, and ligament in his lover's body before shifting any of his attention to her erogenous zones, let alone his own genital gratification.

As I look back on it all now, it actually seems like Jeanne was almost erotically weaponizing me, molding me into her idea of the perfect lover. Even the strength training she encouraged me to pursue was designed not to give me the massive muscles that most women find a bit off-putting. So I would carry a portable pull-up bar in my duffel and build my upper body strength with endless chin-ups and push-ups right there in the door of my room wherever I was staying. Yoga and aikido were also prescribed by her as part of my daily routine, rendering me flexible in ways that few men achieve. By the time I left for college, I was six feet tall, weighed 200 pounds of very solid muscle, and was with good reason uniquely confident in my prowess with the ladies.

Stanford was replete with targets of opportunity, especially since I of course chose to major in Psychology, which had a female to male ratio of about 4 to 1. Once the PE department realized I was a 3rd degree Black Belt in Aikido, they happily paid me to assist their martial arts instructors, so I had an entree into that community as well. And that was where I first encountered my Mistress near the end of my junior year.

There was quite a buzz in the dojo (well, technically, it was a multi-purpose gymnasium, but for nine hours week we called it the traditional Japanese term) about a new instructor who was to take over for our sensei who was relocating elsewhere. Sensei Jacqueline was a fourth degree black belt like our previous teacher, but she had trained in Paris before moving to Palo Alto earlier that year to take a professorship in the Psychology department. She was lovely in the way that only Frenchwomen seemed to effortlessly accomplish: tall, slender, and imperious with a stylishly short brunette coiffure setting off her elfin face and huge brown eyes reminiscent of Audrey Hepburn. I was in full crush mode immediately, as she no doubt sensed.

It turned out we were well-matched in combat, my two inches of extra eight and 50 additional pounds of muscle rather precisely offsetting her more developed skill and subtlety. She quickly realized this, and asked me to stay after the regular sessions for private one-on-one sparring practice. As anyone who has ever seriously practiced a martial art will tell you, there is a unique intimacy that happens in actual fighting practice. The intense physical closeness combines with the real dangerous potential in many of the moves to cultivate a powerful camaraderie rarely equaled in other sporting activities. Sensei Jacqueline and I developed what I thought was a real friendship over the months of extra practice in the empty dojo. We would toss each other around until we were both quivering with exhaustion, and then lie on the mat chatting pleasantly until we cooled down enough to head to our respective homes. More and more as the months went on, those chats became deeper conversations until I realized that I had made something precious: an older woman who was a real friend and confidante. I fantasized furiously about her, but she was always careful to respect the ethics of our roles and keep things purely friendly until I graduated from Stanford and was no longer her student.

Everything changed just after my graduation with a phone call in the middle of the night. I was blearily awakened by my cell to hear the voice of my clearly distraught stepmother with whom I had spoken at length earlier that evening. We had enjoyed our usual intimate chat during which she had casually mentioned that my father and she were planning to go to bed early. Several hours later, she had awakened to find him already cooling from a fatal heart attack. With horrible suddenness, she was a widow and I an orphan.

This unanticipated loss affected me very confusingly. I had been reasonably fond of Dad, but not actually very close. In fact, I could not recall the last time he and I had conducted a real conversation on our own. Jeanne had always mediated our interactions with her usual social deftness, but I honestly didn't know the man very well at all, nor feel known by him. So I was stunned, but far from heartbroken. I drove to their palatial home in the Peninsula hills in time to see the paramedics take his bagged body into their ambulance, and that was that. Jeanne was the executor of his estate, and it turned out that she and I were both unimaginably wealthy as he had split his 9 figure assets evenly between the two of us except for their home, which went to her. I had been wondering how I was going to make a living after a post-grad internship in a local startup using smart-phones to assess and treat mental health problems. Well, that question was answered: I didn't need to work a second the rest of my life since the passive income of my inheritance was well over a million dollars a year.

Jeanne seemed (appropriately) much more upset than I was by his death. I had never seen her distraught before, and my fondness for her made it excruciating to see her in such pain. She had always been the one to physically and emotionally comfort me, never losing her calm, warm composure as she held and stroked me through my various childish and adolescent woes. But now, she clearly was verging on unhinged and in need of something like what she had previously provided so unstintingly.