Jenny's Dilemma

Towards the end of Tuesday afternoon, just as the staff filed out just after 5pm, I headed for the bathroom with the purpose of removing my panties, just as Mr. Smith wanted for that evening's session. Soon, Mr. Smith was on the line telling me that he was ready to begin. I knocked and entered his office room and stood by the door, having closed it behind me.

"Jenny, come over here please, I want you to look at something I have displayed on my screen, there is something here I am sure will be of interest to you."

I stood by his side, my breast at the level of his chin.

"This is a new contract of employment that I have drawn, more appropriate for the role I have in mind for you," he said, not hiding the eagerness in his voice.

As he spoke his hand reached under my skirt and the edge of his palm wedged itself between my thighs pushing up against my pussy lips. Continuing as though nothing was happening he went on speaking.

"You will see that I have raised your salary to personal assistant level and included additional overtime payments."

His fingers were now opening my sex lips and I began to respond, pushing down against them, my hips beginning to rotate slightly.

"You will also see that you are required to accompany me on occasional weekend trips to conferences and the like. Ummm... Are you alright my dear, you seem a little flushed?"

His fingers were now exploring, rubbing and flicking my moist clit causing a sharp in takes of breath but he continued to tease and arouse me. I believe that was his purpose.

"How does this look my dear, a considerable rise in remuneration and in status? I think you need to agree to this to cement your position here in the firm. What do you say?" He was tempting me in more ways than one ... better job prospects and also, at that heightened level of arousal, more opportunities for such exploration.

I was now fully aroused, my hips moving back and forth, my breathing stronger, and my face flushed. I whispered that I would do whatever he thought best for me. Cruelly he suddenly removed his hand and told me to sit in the chair facing his desk. I tried to regain my composure although it was difficult for me, smoothed my skirt and sat down, my legs pressed firmly together. There was an effort on my part to fight back the desires that plagued me then.

"Now Jenny, we come to the email you sent me. I instructed you to write in detail and disappointingly there is very little of that here. No...stop giving excuses...be quiet...I am speaking. I want you to go over to the spare desk and write a full account of your last 'event' and I mean full, no detail missed out." His voice was firm and demanding.

I rose from the chair and settled behind the desk at the corner and began to type out the events of that Monday.

After about half an hour or so, as I continued to type, Mr. Smith drew my attention to something else.

"Oh Jenny this weekend we will be travelling to a conference in Copenhagen. You will arrange the hotel and meet me at the airport at 6.00 pm on Friday evening. Take Friday afternoon off to pack and collect your passport."

I knew that was an indication for me to stop so I got up and came across to where he sat behind his desk.

It had taken quite an effort to type the details that Mr. Smith wanted. The time to complete the piece was too short and I was certain that it would remain incomplete. But, I was fast on the computer and tried to do as best as I could. But my best efforts were not enough and I had to stop before I could complete typing out the entire events that had occurred. He didn't take the sheets but advised that I take a seat and read out my description of the events as these had occurred.

This is what I read out to Mr. Smith:

REPORT OF MONDAY'S EVENTS:

Before I give a full account of my last assignment and what, exactly, were the 'events' that took place then, it would be wiser to give a brief introduction of my employer and the requirements of my part-time job. I think this would help one to judge me in a much wider context than the narrower one, just on the basis of my assignments.

It is not unknown to you that I do have some financial needs to supplement the income that I get from this organization. It helps me in the way I live, for comforts are always a prime consideration and motivation for me to do anything or everything or nothing at all. This may have, unfortunately, earned me a reputation that was difficult to brush off when I applied for the job here.

Anyway, to shorten the introduction - in applying for a part-time engagement, I ran into one Mr. Howard, an elderly man but apparently affectionate or so I thought, who offered me a job. The nature of task that his firm took up was organizing events, and so classified as 'Event Managers' offering private service to clients, based on their personal tastes and requirements. I never did come across any other staff in his 'firm' excepting a young girl, almost my age. She was rather uncommunicative, not disclosing much and keen to keep to herself whenever we met in Mr. Howard's office, a room really. But she left after a couple of months of my joining so that it was just me who reported for work.

When we, that is Mr. Howard and myself discussed the terms of appointment, I found him to be rather evasive on a number of issues. I was a trifle scared, worrying that this was probably leading me to being some sort of 'call' girl. I flatly refused, almost out of my seat to get out of the room.

Mr. Howard coughed a bit before telling me, very affectionately and sweetly, that he had absolutely no intention of doing anything or entrusting me with any work that would result in physical harm to me. No one would touch me, he assured me, excepting a handshake or a casual pat on the hands or things like that. All that I had to do was to accompany clients, who were usually elderly, just chat with them, may be see a few movies together, go around the city in their car... all innocent stuff really. He coaxed me to accept and offering me almost double of what he had offered initially. I had finally accepted the part-time job.

I know Sir, you must be thinking that I am trying to say something in defense, but I say all these so that you will understand the truth behind the events and that I am really not a bad girl just because I try to keep my clients happy.

Yesterday evening, Mr. Howard had sent me on my last assignment, the last 'event' that you want me to describe. Usually, he would hand over a typed sheet mentioning the name of my client and the address where I am supposed to meet him or her or them if there were more than one, the time and briefly, what the client had indicated as a requirement.

Last evening after I left office, I went straight to Mr. Howard but I found that he had left. This happens sometimes, so I opened the office room with the spare key that I have and went inside. Right on the table, I found the typed sheet and I quickly glanced through the lines. What I read was something like this:

Mr. Edward Slater, (Aged 67) & party.

Hotel Teddy's

Time 6.30 PM

Meet Receptionist at scheduled time for further information.

Dress: To be specified by client.

Now, Teddy's does have a reputation, but in a totally different sense. They have a few guest rooms but, in addition, they also have rooms to hold banquets, exhibitions, discussions and the like. There have been reports that the rooms are frequently used for purposes other than decent, so frankly I was a bit apprehensive.

When I met the receptionist and introduced myself she searched underneath the desk where she sat and took out a rather big packet and handed over the same to me.

"Jenny, I believe that you would have been told about a dress requirement for this evening assignment. Well, this packet contains the dress and accessories. All you have to do, sweetie, is take the elevator and go up to the fifth floor and walk along the corridor till you come a room marked 'Parade'. Walk in and you'll find a rest room where you change and then walk in to the main hall. Run along now ... there are a few people waiting impatiently for you." She winked.

I was already late and I dashed away to the elevator, offering a feeble thanks to the receptionist. Out from the elevator, I sprinted across to locate the room 'Parade' and into the washroom. When I opened the packet I was dumb founded. What on earth was this dress doing in my hands and how, in heaven's name, would I wear this and present myself to my client.

What I held in my hand was a really a four piece school girl dress that included a pleated dark green plaid really thin mini skirt, a white ruffle edge top with plaid necktie, underwire lace bra and a matching panty that had a plaid bow and detachable garter straps. Inside the packet I also found thigh high stockings with lace band and a box containing five inch heels. Additionally, a black imposing riding crop lay among the folds of the dress.

I was aghast. This dress would expose far more than what it would cover. But, I had little time to either think or retreat. Besides, at the corner of the sheet that I took from office, Mr. Howard had mentioned something that didn't escape me; adequate 'compensation' if the client & his party were fully satisfied.

Even if reluctantly, I quickly changed and wore each of the items that were given, including the two ribbon hair ties to give that school girl look. I applied the lipstick, adding a dash of lip gloss and after a final look in the mirror, walked in through the door leading to main hall that the receptionist had mentioned.

Pushing the door open, I ran in, holding the riding crop in my hands. I stared in horror at where I stood! I had, in fact, walked right on to a stage through the wings. In front and below the stage, about a dozen men including two women, most of them elderly, sat on luxurious cushion chairs. Each of them had a look of curiosity but, more importantly, they were gaping at me with their mouths open and impatiently waiting for the show to begin.

At this stage, I had to stop ... because just underneath the piece, I had written in bold TO BE CONTINUED. I had no time left and had stopped typing.

When I read out the last few words 'To be continued' Mr. Smith just stared at me, his face distorted and livid in more anger than I had previously seen. It was obvious that his cause of anger was that I hadn't completed the task.

"Sir, I am very sorry, but you had stipulated a time limit. That's the best and most I could type out in my allotted time... It is not intentional. Please Sir, I beg you to forgive me!" I pleaded.

"Why, you little teasing tart! How dare you come to me with a half-finished account ...'to be continued'...who do you take me for, you ungrateful little hussy. Get up! Get over to the wall ... this instant!" He was simply furious.

The raging man pushed me roughly till I stood facing the wall. He barked at me to put my hands at shoulder height to support my weight, my feet spread as he came nearer and lifted my skirt, exposing my uncovered cheeks. I offered more apologies, entreating him to forgive and that I would quickly finish the work if only he gave me some more time. But he had made up his mind.

Twisting my head to one side with his left hand wrapped in my hair, he began to spank me with his right hand. Not the mild, caressing spanks I had received at my last training session but hard, stinging blows which made me shout out as they rained down on my soft, round little backside. All the time whispering into my ear:

"You think you can just ignore my instructions...after all I have done for you...how dare you think you can get away with this...your disobedience will not go unpunished Jenny...you will learn I am no soft touch...you WILL do as I require...no more special consideration...you will EARN my trust... do you understand? DO YOU?"

All the time the spanks continued, my buttocks turning raw in pain. After about fifteen minutes or so of ignoring my cries, then my sobs and finally my whimpering, his anger subsided. Regaining his composure he told me to lower my skirt and to go back and sit at the spare desk. I was shocked and sore but Mr. Smith had made it very clear that I was here to do as I was told and that failure to do so would incur the most severe punishment. I felt bad that I had let him down, that I might lose my job and I looked at him with imploring, repentant eyes. But he simply ignored my imploring and didn't even care to look at me anymore. In the end, he gave me a firm command, which I knew was the last straw.

"Now Jenny, finish your account, leave no detail out. We will be here as long as it takes."