The Councellor Miss Wendy - Cover

The Councellor Miss Wendy

by wendyk52

Copyright© 2023 by wendyk52

Coming of Age Sex Story: The combination of feeling her fingers grasping, fondling me and the warmth of her breath as she moved nearer had the inevitable effect of making me swell. If I had any thoughts at all it would have been one that screamed, "Oh my God, I am being touched by a FEMALE!!"

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/Fa   Consensual   Reluctant   Heterosexual   Fiction   True Story   Cheating   Slut Wife   Interracial   Exhibitionism   .

I was an only child and growing up was not easy. Throughout my childhood my father was often absent, spending most of his time working away from home, leaving me to be bought up in the not-so-loving care of my mother who, not that I realised it at the time, was clearly a crazy woman who had some very odd ideas on motherhood and how to raise a son.

A devout Christian, she was forever quoting phrases from the bible that in her mind justified her view of the world and that translated into her being overbearing and constantly monitoring my behaviour. As a child I was given very little free time to be left to my own devices and to make my own amusements, therefore, most of my time was seemingly spent having to do chores under her watchful eye. She was quick to criticise any transgression and to make comments in sarcastic tones of my perceived failure to meet some of the ridiculously high standards that she arbitrarily set for even the most mundane of tasks.

She was completely oblivious to her lack of motherly love and made no apologies for, as she so often told me, everything that she did or said was ‘in the name of the Lord’. She was, I was to later understand, a religious nutcase.

No, life was not great and school became a welcome relief for me to escape from the oppressive atmosphere that pervaded at home but, unfortunately, it would only be a temporary relief for I knew that when I returned home from school, I would find myself being admonished for some misdemeanour or subject of an accusation of not having satisfactorily carried out some chore that I had been expected to do before I left home that morning.

In short, she was a very difficult person to live with and it was only in later life that I came to understand the reasons why my father took every offer, every chance, to work away from home as she must have been a nightmare of a wife.

So, was there any respite from her attentions; any pleasures in my ‘miserable’, lonely life’?

Yes, there was but I do not remember the exact age when it happened other than it being early on that I discovered the joys of masturbation (or, wanking, as I overheard an older boy at school calling it) and I became an enthusiastic devotee.

My wanking started after I began to experience getting erections for no reason that I could discern. Indeed, up until the time it first happened, I had no idea that my willy was meant for anything other than peeing through and it was complete surprise that this condition should arise and make what had previously been a floppy little fleshy protuberance swell and become stiff.

My ‘Damascus moment’ came about when, in my early teens, after (and under her supervision) I would say my goodnight prayers, be dismissed and sent to my bedroom. In the beginning when an erection happened there was never a time when mother gave notice of the tenting in my pants so it was a relief when I was able to escape to my bedroom ‘undetected’ where I was then able to investigate if there was wrong and if in some way I was ‘abnormal’.

At that early stage of my development, in my innocent years, I had nobody in whom I could confide (certainly father was never there just when he was needed) and so it was I was left alone to explore and to soon discover that if I rubbed and caressed this unexpected growth spurt to make it ‘go away’ that, contrary to expectations, a very pleasurable sensation would ensue.

I was excited by this discovery and it quickly got to the stage where rather than be alarmed at getting a ‘stifle’ that I would be looking forward to it happening so that I could get to my bedroom and sooth away the cares of the day before sleeping.

Mother was I believe a little surprised at my new found enthusiasm for evening prayers and for me to say an early Goodnight. In her mind she must have believed that her constant nagging was bearing fruit; in mine, it was to be seeking ecstasy of another nature.

And so, I settled down to an uneasy peace knowing that if I got through the day without incurring her wrath in some way or other that once I got to my bedroom I could once again delight in stroking and fondle my sensitive cock to bring myself to what I later understood was called an orgasm.

In those early days of my wanking career (I call it that for now, later in life, I continue to do so) there was never any emission to accompany the climax, just a glorious feeling of warmth and pleasure that would envelop my whole body. It was a few months that, after an initial scare at it happening, a sticky, syrupy clear fluid began to dribble when I stroked my stiff cock. I quickly realised it was not pee but, no matter whatever it was, I began to appreciate how much smoother it made my fingers slide up and down and made for a whole much nicer experience. It was only a few days later after this latest development that I had another scare, my first ejaculation.

My initial shock of having produced another different fluid in such pleasurable circumstances was quickly replaced by a sense of pride. I was not so innocent that I did not understand what had happened for the rudimentary sex-education at school that I had received by that age had hinted that such a thing was part of the process; I was just surprised that I had achieved it so soon!

And so, I settled down to my nightly pleasures with a new element to anticipate at its climax. I was fascinated by the amount of sperm, semen, spunk, or whatever else it was called, was produced and the force at which it was ejected. Who knew that I was capable of such a thing; I was very proud at the evidence of my growing up.

However, as mother had often told me in one of her rambling sermons, ‘pride comes before a fall’ and I was soon to learn the truth in that proverb.

It was part of my bedtime reading that rather than take the bible to my room, as my mother would have wished that in those pre-internet years, I used to take the latest Sears catalogue so that I could fantasise, she thought, about the toys that were listed and pictured and for which we had no money to buy. In truth, it was not the toy section that I scanned; it was the lady’s underwear and nightwear section that fascinated me. I had no other points of reference when it came to the female form and although, in retrospect, the models were relatively decorously dressed (or undressed in my mind) it was the closest I had come to in my developing years to seeing women without dresses or such clothes. Grief, did my imagination work overtime looking at bras, silken panties, stocking-clad legs, and garter belts and such. The thoughts of the treasures beneath that were so artfully hidden in those catalogue pictures make me shudder with excitement even today.

So it was that with the catalogue open at an appropriate page that I would lay back, stroke my rigid cock until the thoughts of how it would feel to have one of those ladies replacing my hands with their own would bring me to the inevitable conclusion of yet another fountain of cum spurting over my stomach and beyond.

And it was the ‘beyond’ that was my downfall.

As soon as I open the front door at the end of another school day, it was clear that I was in trouble. Mother was waiting for me with a look like thunder on her face and the Sears catalogue on the kitchen table open before her. I say open, but not really; mother made a great show of how it was not possible to open the book properly because some of the pages were stuck together; the pages in question being the ones that I so avidly looked at the previous night.

I was not given the opportunity to either put down my school bag or to offer any explanation as to why the catalogue had been, in her words, defiled in such a disgusting matter, she had already figured that out. She then went into full-on preaching mode and how I had betrayed her trust in me; how I had broken an unwritten law and had abused my body in the most foul and despicable manner and so on and so. She did not use the word but, in her eyes, masturbation, was a heinous sin and those who did so were guilty of doing the Devil’s bidding and there was no way she was allowing ‘her precious child’ to be following that path! She followed up her diatribe with saying that those who did so were guaranteed to inflict bodily harm upon themselves and they would thereafter be ‘deformed’ and, for sure, given I had succumbed to ‘that sin’ I had most probably already caused myself to become misshapen. In short, she put the fear of God into me.

There were a few consequences to this sermon. Firstly, from there on, I was not allowed to either borrow the Sears catalogue or to have my bedroom door shut at any time, certainly not when I went to bed at night.

The other consequence was even more life-changing; it led me to meeting Miss Wendy.

After the roasting that I had endured from mother, I could think of little else other than how my only pleasure in life had effectively been taken away from me. My bedroom which had become my sanctuary where previously I could wank without shame or disturbance was now denied for, she now kept a close eye on me to make sure that I was not falling back into sin.

Given I was a shy and sensitive teenage soul, her words struck hard but I still found it very difficult to keep my thoughts away from the pictures in the Sears book and the effect they caused upon me. I was constantly conflicted and therefore my schoolwork was sidelined due my forever daydreaming about women’s lingerie and the possibilities of my stiff cock being involved in the fantasies that constantly ran through my mind. All these distractions led to my grades suffering and it was not long before it was noted by my teachers that this ‘A grade’ student might have emotional problems that needed to be investigated.

I knew of Miss Wendy. She was supposedly on the teaching staff; not a teacher but someone who was worthy of having her own office in the administration block of the school away from the mainstream. It was not until I was sent to her office that I learnt that she was a Student Councillor, someone who was qualified to mentor ‘special needs’ pupils and ‘help’ troubled youngsters such as myself. (I say ‘like myself’ but the only other students who I knew of who had been sent to seek her guidance were always black boys. I was not sure what this said about me!) I will forever remember my first encounter with Miss Wendy as clear as day; it was a revelation. I nervously knocked on the open door of her office; she looked up from her seat behind her desk, then brightly said, “Come on in. Close the door behind you so that everyone knows we must not be disturbed. Now, sit yourself over there on the couch, tell me what is going on; why are you such a sad boy?”

I do not know exactly what my teacher had told her about me but clearly my unhappiness must have been evident for her to make this snap judgement. I was taken aback by her powers of perception!

I was further impressed by her appearance. She stood up and came around to my side of her desk to reveal she was wearing a dark grey business-like suit of a single-button fitted jacket over a white blouse which was open at the neck (revealing an interesting looking cleavage) and a skirt the hem of which came to just above the knees of her dark nylon-clad legs. On her feet were black high-heel shoes which effectively completed the vision of a very business-like lady. She was a total contrast to the only other woman in my life, my mother, who invariable wore high necked long cotton dresses which were more appropriate to a woman from the age of the Pilgrim Fathers’.

Miss Wendy sat herself down on a seat opposite the couch where I had settled and I had to stifle a gasp when she deliberately crossed her legs and her skirt rode up to reveal the dark band of her stocking tops and, good grief, was that the fastening of a suspender belt that I glimpsed?!

I tore my eyes away and looked up to see her smiling at me but there was no doubt from her expression that her action had been deliberate and, I was to learn later, designed to put me at ease. It certainly worked; I was instantly charmed by her friendly nature; her openness; her perfume and her appearance which was straight out of my Sears catalogue. She had my full attention when she asked, “So, what’s going on in your life that is making you so miserable?”

And so it began, the outpouring of my childhood woes to a woman who was my ideal as a wet dream. I told her as best I could of my home regime; of my mother’s devotion to her faith and her interpretation of the bible and how she projected those ideas onto me; of my absent father who I missed having around so much and then, with the time allotted to this appointment with the Councillor running down, I then babbled on about having been caught out ‘self-abusing’ and my mother’s suspicion that I must have damaged myself in the process.

Miss Wendy, who up until that point had been listening with respect to what I had been telling her, laughed out loud and scoffed, “Oh my, that old one. I cannot believe that there are still people around who peddle that kind of nonsense. Oh dear, oh me, let us take a breath here and let me assure you that nothing of the sort will have happened if you have been, what did your mother call it, ‘self-abusing’? Let us give it its proper name; you have been masturbating and that is quite a normal activity for a growing up boy and nothing to be ashamed about. There are a lot worse things that you could have been doing that would have got you into more trouble than playing with your penis.

“I do not like to give contrary advice to what parents’ tell their kids but, believe me, exploring what your mother ought to be calling ‘God’s Gift’ and getting sexual relief that way is just so normal. Stand up...”

“Huh?”

“I said, stand up. I want to prove that you have nothing to worry about... “ She looked at her watch, “ ... be quick, I have another student waiting to see me.”

I got to my feet and stood before her. She remained seated and leaned forward and without hesitation pulled down the zipper on my pants. I was shocked rigid and therefore made no effort to stop her as she reached in to fumble my cock free of my boxer shorts. Paralysed with embarrassment I remained standing with Miss Wendy softly holding my cock and seemingly making a close examination. The combination of feeling her fingers grasping, fondling me and the warmth of her breath as she moved nearer had the inevitable effect of making me swell. If I had any thoughts at all it would have been one that screamed, “Oh my God, I am being touched by a FEMALE!!”

However, it did not last long for soon the feeling of pleasurable embarrassment was replaced by one of disappointment when she took her hands away and said, “Nothing to worry about, young man. That is a very nice-looking penis you have there and it is growing just as it should. You should not believe everything your mother tells you. Now, get yourself back to class; I have got another boy waiting to see me. I’ll see you again, same time, next week.”

I put my dick back in my pants and zipped up. Before I had even got as far as the door Miss Wendy had resumed her place behind her desk and, pen in hand, her attention was already on the pad upon which she was writing and making notes, no longer concentrating on me. I was not to know that at the same time beneath the desk she was fingering her wet pussy with her other hand, thinking about yet another boy’s cock that she had successfully, and so easily, held in both her hands.

I left the office in a daze and almost tripped over the spread legs of an older black boy who was sprawled on a chair waiting his turn to go into her office. He grinned knowingly at me.


That visit was a watershed moment in my life. For the first time I had encountered someone, another significant female, who held a totally different outlook on life to that espoused by my mother. A lot of what Miss Wendy said after I had told her of the ‘house rules’ under which I had been bought up made an awful lot of good sense and, I confess, as I left her office, I had a feeling of being in love for the first time in my life. The hour spent in her company had been a revelation and I could not wait for the days to pass by so that I could return and hear more ‘good advice’.

That I made no mention to mother that I had been sent to see a councillor; she would not have been amused. The very idea to her that I had been talking to someone outside of the immediate family of ‘personal problems’, more so that it had been a female would be a matter of shame. She certainly would not like to have heard that her values and rules had been challenged as being just plain wrong.

No, best I keep that indiscretion to myself and to take Miss Wendy’s more acceptable advice that she gave, that I find some discrete place away from the house (the woods?) or take the opportunity of when I go to use the toilet and a locked door to do my, she said with a giggle, ‘self-abusing’.

Mother had other things on her mind. She hinted to me that she had suspicions that father was not being true to their wedding vows, that he was using the excuse of working away from home to be straying from the path of fidelity. That may have been true but I had not the courage to tell her that my own suspicion was that she was a complete nightmare to live with and he was looking for a quieter life, an option that was not available to me.

Then there was the other thing that was constantly on her mind, she was almost totally focused on preparing for an upcoming weekend when she would be attending a religious revival gathering somewhere up-state. It was the only time I think that I witnessed her anticipating anything in life with pleasure as opposed to her usual gloomy outlook on the state of her world.


My next appointment for counselling was 7 days later and being keen to continue with the discussions, I excused myself from class early. Schoolboy error, I should not have rushed for my early arrival meant that as the door was firmly closed that in accordance to her rules I had to sit waiting on a chair outside her office. I could hear voices and murmuring within which then went quiet but eventually the door was opened by the same black kid that I had stumbled over last week. He had a smirk on his face when he saw me but said nothing.

Miss Wendy called me in and told me to shut the door behind me. She looked up from behind her desk and acting the complete professional made no mention of what might have occurred prior to my arrival.

She stood up to reveal she was wearing the same grey business skirt as before paired with a similar white blouse. I noted that the jacket was draped over the back of her desk chair. She told me to take my place on the couch and my heart gave a jump when she bent to sit on a chair in front of me and the blouse gaped and her cleavage was revealed. My heart gave an even greater stab when she crossed her legs giving me a quick (very quick) flash of her white panties.

She gave no indication that she had seen my blushes but rather began writing something down on her pad (well, I supposed she could have been writing, maybe she was just doodling). She began our session by asking me how things were at home and had I been following her advice about finding relief now that I had been assured that there was no scientific foundation to wanking causing any damage to a developing body.

I shyly admitted that there had been a couple of occasions when I had managed to escape my mother’s attention and had done so. She was pleased to hear it and repeated her advice of last week which said that masturbation was ‘beneficial’ and that I should be encouraged to pleasure myself so that I had a proper outlook on life and not one that was dictated by the religious zeal of someone who should, frankly, know better. (She did not use those actual words, but that was the gist).

 
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