Jenny's Dilemma

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Jenny gets to know what she really wanted.
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Lady_S
Lady_S
22 Followers

This is a story about a young girl and her changing relationship with her boss as he trains her over a period of time. There is no underage character in the story which is purely a work of fiction.

*****

I was a habitual late comer to office and often I left office early too for reasons that would be evident later on in my narrative. My last supervisor had warned me on this lapse quite often. But I ignored him till he was just on the verge of taking action. Just then, he decided to quit, much to my relief but he was just replaced by another supervisor. I should have realized that, as an authority, a supervisor had to impose rules and in turn, as an employee, I had to obey those rules and I really had no reason to feel relieved. Things continued to be normal for a while but eventually it became worse than before. I observed that the new supervisor was keeping a much closer watch on the staff under him, obviously to my discomfort, and I just dreaded being summoned any day. I didn't have to wait long.

At 5 pm a week after his joining, as most of the staff started to make their way out of office and I too was packing to leave, my new boss Mr. Malcolm Smith called me on my extension.

"Please wait behind till the others have left Jenny, then step into my office." That tone, I was sure, would not lead to very happy conclusions. But it was my thinking that he was new and I would try to get the upper hand on the first day itself.

I straightened my dress, ran a few fingers through the lustrous strands of my hair and then, without knocking, walked in straight, pulled a chair and sat down.

I got the shock of my life when he confronted me with something that I was certain nobody knew ... or rather, knew till now. I had lied to the company to get this appointment and, somehow, my new supervisor had got a whiff of this secret. I really didn't know what to say when he threatened me with dismissal and asked if I had anything to say.

The truth is that I had a huge debt on my head and I had, in addition to this job here, taken up a part-time job where I was required to put in a couple of hours three days in a week. Invariably, I was either late on these days or found a pretext to leave early. I had incurred this debt due to my way of life but that's another story that I would like to forget. I knew I couldn't tell these things to my supervisor. That'll surely be a reason for my dismissal under the company's Disciplinary Code.

"Is there anything you want to say, Jenny?"

I was uneasy, unable to give a proper explanation. As I looked towards the floor unable to look at him, I hoped that my silence would get me out of harm's way. But I knew he still had his eyes on me, waiting for an answer.

"Mr. Smith, I am really sorry Sir ... actually I was desperate for the job," I appealed to him with imploring eyes.

He remained unmoved, just tapping a finger on the desk and staring at me with cold eyes, silently sending the message across - go on, tell me the reason.

"I beg of you Sir, Oh! Please! I didn't mean any harm," I was almost on the verge of tears, "I am willing to compensate."

"Jenny, I can see that this job means a lot to you, and of course I don't want to start my new role here by sacking someone, but the disciplinary code is quite specific I'm afraid." He waited, prolonging my distress before he continued.

"Of course in my old firm, years ago, when a young woman failed to meet the standards required or transgressed our behavior code, we had a different way of dealing with the matter."

My immediate thought was that there was possibly a chance to save my job...maybe a fine or possibly a probationary period.

"However, I can't imagine that these days a young woman would accept that sort of...how shall I put it...corrective treatment...not in this time of feminist assertiveness."

My hope began to recede.

"I do have some discretion I suppose...I could hold on to this information till tomorrow morning...give you time to consider whether you are prepared to undertake a number of after hours' training sessions, where we could address some of the issues of your poor punctuality and your misinformation on your application form."

I was perplexed at the approach of this new, middle aged man who was my supervisor. On the one hand, he seemed mildly caring and sympathetic while, on the other, glaringly disciplinary and threatening. I wasn't sure what approach would help me in retaining my job. I had begged and implored earlier but he didn't seem to be too much concerned.

"What I suggest is quite simple Jenny, if you turn up tomorrow dressed like you usually do in these jeans and trainers I will contact HR immediately, and proceed with the firm's Disciplinary Code. If on the other hand you want to accept my offer... then I require you to be dressed as follows: White or cream fitted blouse, pleated black skirt, heels and white cotton underwear and our first session will take place tomorrow evening. I leave the decision in your hands."

And then, in finality, "Now I am very busy so would you kindly close the door behind you as you leave."

It was obvious that he didn't appreciate the casual dress that I wore and neither did he get on with the modern day feminists. The middle aged and the elderly, I thought, were all a class apart - always taking us to be disobedient and rebellious. Each word that he uttered kept ringing in my ears. Some of the words were harsh enough to make me red in the face. Some brought a sense of relief too. But, there could be no doubt that there was a veiled threat of dismissal looming over my head.

Yet, I stood as I was, quiet for a few moments, hesitating and wanting to say something more to pacify this man.

What was it that Mr. Smith had said about a dress requirement for the next day? It's not that he was insisting on my going around naked but to discard my usual casual dress and wear something which, I thought, was a bit orthodox. If I had to retain my job, wearing that dress hardly mattered to me. It was only the question of those training sessions after office that would spoil a few of the 'fun-filled' evenings that I indulged in.

"Sir, I thank you for giving me this opportunity to rectify myself. You have been kind ...most kind... and I ...I shall surely try... uhhh ... surely fulfill your requirements without fail," I blurted out.

Mr. Smith remained aloof to my words. He was a busy man and his attention was entirely riveted to the papers on his desk. I waited, hoping against hope that he would be pleased and respond. He maintained his silence.

"I have already noted the dress that I am supposed to wear tomorrow Sir. You shall certainly see me in whatever is the required dress code," I continued to say.

He seemed exasperated as he shuffled a bit on his chair. In the end, there was a look of irritation when he looked up. I held my nerve ... I simply had to keep my job.

"And .. and ... I shall stay back every evening to get my training under you Sir," I said in the most sincere tone that I could, " I am certain that it would be for my best."

++++++

One of the first tasks at home was to see if I had the desired dress for office the next day. The items required were nothing special and I was certain of having these in my home and wardrobe. Back home, I was a trifle disappointed. I didn't have either a cream or a white fitted blouse that Mr. Smith had clearly spelt out, and it was too late to get one now. I rummaged through my clothes and found, to my horror, that the nearest to his chosen color was a beige fitted blouse. I had been well and truly shaken the previous evening and I just prayed that this minor difference would be overlooked.

The next morning I made a concerted effort to be on time by getting up early. It helped that the day was not one on which I went for my part-time job. I left early for office and was in before most. Oh God! Help me! Just let me not lose my job - I was praying for the greater part of the day. I did steal glances at Mr. Smith's glass chamber now and then, hoping to get his attention and show how busy at work I was. But I was least in his mind, as he kept himself occupied with the papers on the table or serious discussions with some of the other staff.

When it was almost five and the rest of the staff were in the process of tidying up and leaving for the day, I remained glued to my papers and files. I could hardly offer an explanation to Betty, my colleague, as to what was so urgent that I had to stay back late. In the end, she just shrugged her shoulders and left.

With the departure of all the staff, there were only two who remained to face the silence - me and my supervisor. I was in no hurry to go to his room - I was scared. He would, in time, call me. Of this, I was certain. I kept wondering what would ensue when I finally entered his chamber for my training. Just at that moment, my extension line buzzed busily.

"My office now please, Jenny" I could hear clearly from the other end and these were as cold as they were threatening. I quickly got up and dashed across to his room, not forgetting to knock and waiting a while before I finally entered.

As soon as I entered the room he looked up once before he pointed a finger at the corner.

"Please sit down at the spare desk Jenny, there is hand written document I would like you to type up and sign please," he said tersely.

Mr. Smith had a task ready for me, rather easy I thought although I had to type a document meant for me. The terms of the document, though slightly indistinct, were a bit binding but I had no choice.

The document read as follows:

"I, the un..(illegible), agree that I have con ...(illegible)..vened the firm's disciplinary policy in manner which would normally result in my dismissal. Mr. Smith has kindly a..(illegible) to give me a number of after hours' training sessions rather than dismiss me.

I agree to undertake each and every instruction and comply with all correctional activities that Mr. Smith requires of me. I will do so without argument or complaint. Should I fail to do so, he will contact HR with details of my contravention of the firm's ...(illegible)nary code and I will be summarily dismissed.

Signature............ Date........."

As I began typing, stopping in between to make out portions that were illegible, Mr. Smith came and stood beside me.

"I thought I specified a cream or white blouse Jenny. But isn't this beige that you are wearing? Look Jenny, it's important that you learn to follow instructions precisely, my dear."

I mumbled a faint apology.

"Bring me the document when it is finished and sign it first please," he stated and turned to go back to his desk.

Five minutes later I came over with the document in my hand and stood next to my boss who, instantly, sat up straighter. His shoulder, in straightening, brushed against my left breast. I moved two paces away.

"Let's have a look at this...I see four typing errors here, Jenny. If we add that to the incorrect color of your blouse that makes five transgressions this evening, do you agree?"

I didn't know what to say and simply nodded my head.

"I better just check that you have followed my other dress requirement" Mr. Smith said all of a sudden, and then without warning, he lifted the back of my pleated skirt to reveal a fetching pair of white cotton panties.

I could hardly believe my ears when the authoritarian voice pointed out my lapses and the extent of punishment that these deserved.

"... Bend forward dear, hands on the desk, legs apart face down at desk level...hurry up!" His words left me baffled.

I looked at him, surprised and shocked. I was aghast that a minor error could evoke such a harsh and humiliating punishment. My eyes pleaded pardon and my words begged him to condone.

"Please Sir ... Sir please. I promise that there will never be a recurrence of these lapses and omissions in future. I beg you Mr. Smith. Please Sir, don't do this to me," I was howling away.

The supervisor stood his ground. A hand simply gestured towards the desk, indicating that I follow what he had said.

I was crying when my efforts failed and slowly bent down, my hands on the desk and my face almost touching the surface.

My humiliation was complete when he took a step forward and, without much fuss, put a hand in between my thighs and slapped the insides to suggest that my legs should be parted, so that he could carry through with his punishment.

I was horrified when the eventual punishment was about to begin. Spanking was a natural form of punishment no doubt, but to rub it in by pulling down the panties up to the top of my thighs and strike on the naked skin, was a totally different thing altogether. I braced myself for the pain that would surely follow, but wondered if this wasn't something that was not even imposed in school nowadays.

I expressed another round of apology, knowing fully well that it would serve little purpose. The punisher always went through the whole exercise, whatever he or she had decided before the punishment began. Mr. Smith was no exception and I thought that he took an added pleasure in seeing me subjected to this humiliation in repeated begging and to be invariably declined.

"Jenny! This will be much better for you if you just stop protesting, and do try not to wriggle about otherwise I will have to double the punishment. Do you understand?" He spoke in a grave unperturbed voice.

Whack! The first spank hit me on the ass cheek and I winced. It hurt but, I had to admit, it was not that hard to be unbearable. There was a hidden softness in it that I couldn't explain to myself. Surprisingly, Mr. Smith seemed to comfort me by running a hand over the cheek, circling and caressing it.

Whack! The second one followed after a while, though not immediately after the first one. It was not the usual type of spanking that one might experience, where one follows the other without a pause. Mr. Smith repeated the process of comforting me, taking longer with the rubbing on the suffering cheek. This act of pain followed by immediate comforting was so new an experience that I could feel a tingling sensation in those regions of my body. Only two of the allotted five had been completed and I was already expecting the next one without fear.

"I think you need a little cold cream dear, to take away the stinging, just stay exactly as you are for a moment." He picked up something from his table and before I knew, he was rubbing some cream around my ass cheeks, firmly and slowly. Inevitably, some of it went down to the crease between the cheeks and I tensed when a finger ran down on to it.

As the upper part of my body lay spread-eagled on Mr. Smith's desk, I couldn't prevent my hidden fantasies to take wings. I recollected the events and sequences of a porn video that had given seed to this fantasy in which the girl, of almost my age, with her hands stretched and tied, is similarly spanked and that too, openly, in front of a select few elderly gentlemen.

The effect of recapturing that fantasy, coupled with the happenings in reality, were good enough reasons for a wetness to creep in at the most inopportune moment - bent naked in front of my supervisor.

I wouldn't know if the wetness had been observed by him but, in between the breaks of the remaining spanks, under the camouflage of sympathetic caressing, he did rub along his finger along the spot between my legs. In effect, I now wished that the number to be more than the five that had been decided upon. I think a sigh of regret might have escaped me but all he did was to get a cream of Nivea from his table and sooth my pain with its help. Pain had now given way to pleasure.

"You did well Jenny, and I would go as far as to say I am pleased with your eventual compliance with my punishment. I am sure that means there will be less nonsense in the future when I need to administer corrective punishments again" he said, when the punishment was over.

He then asked me to stand in front of the desk, his eyes running over me as I stood with my slightly ruffled hair, the undone button on my blouse exposing the soft fullness of my youthful breasts. He continued to look, saying nothing for what must have seemed like an eternity to me. I shifted nervously from one foot to another, unable to look at him in the eye.

After a few minutes of this intense scrutiny, Mr. Smith set an additional task - one that had to be completed over the weekend. I was more than surprised when I heard what the task was. How on earth did he get to know about the 'job' that I did in the evening and how would I be able to tell the details of that job to anyone at all? Yet, he seemed to be aware of it or else why would he say, "Full account, Jenny, do not leave out any details and I will know if you do!"

I thanked him for letting me go without reporting me to HR and then turned to leave as quickly as I could. Just when my hand was on the door handle, his voice floated across.

"Oh Jenny just two more things my dear, lipstick...red please from now on ...and for Tuesday's training session I think we can forego the panties, don't you?"

During the weekend and beyond till Monday, I thought over this task. I kept thinking that I had time till Tuesday although, I knew, ultimately, I would definitely have to tell the truth. By late Monday night, the draft of my email was ready and I only prayed that this would not pave the way for further humiliation. I was, nonetheless, satisfied that it did not reveal the full truth and yet factually there was nothing incorrect in it either. I went through the draft once again which read as follows:

"Dear Mr. Smith,

I have the most profound respects for you and I find that in this very short span that you have been our supervisor you have been taking a keen interest in improving the standards of our work and behavior.

As a follow up of that high standard, you have asked me to present to you the nature of job that I am entrusted with during my spare time in the evening to better understand how best my potential could be utilized in this organization by you.

The purpose of taking up this part time job is to be able to meet the various monetary needs that haunt me from time to time. The pay that I get here, in this organization, although high, is inadequate for me. So I have taken up this job, which is part-time.

Honestly, the job is otherwise not such that I can boast of and tell everybody about. I have been engaged by an 'Event Manager' who caters to clients having kinky demands and requirements. They pay well, so, even if these demands are not always normal or proper, I try to accept these rather 'difficult' assignments for what it yields in the end. Besides, the time required for each assignment is, at best, three hours either before my office hours here or just after it. So it is not too inconvenient for me. Also, it does not, in any way, hamper my services to this organization where I am engaged full time. My loyalty and sincerity here is true - I can assure you.

I hope you shall find my information to be clear and not too much to your dislike.

Yours respectfully,

Jenny."

I pressed the 'enter' key and was both happy and apprehensive to read the message that loomed overhead - Your message has been sent. I was happy because I had completed my task. I was apprehensive for I didn't know the effect that it would have on Mr. Smith.

+++++

Monday passed uneventfully at work. I continued to dress formally and there were several appreciative glances from some of my younger male colleagues who clearly appreciated the tight fitting blouse that accentuated my breasts and the heels that extended my shapely legs and tightened my buttocks showing off my pert bottom. I tried to look more confident and exuding a more professional business-like manner in my approach.

Lady_S
Lady_S
22 Followers
12