The Adventures of Polly Pt. 01

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A legal secretary learns the importance of spelling.
3.7k words
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Part 1 of the 5 part series

Updated 06/10/2023
Created 05/25/2020
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It all began with Polly, about 24 years old and a picture postcard Australian blonde. Although Polly is quite bright with plenty of initiative she cannot seem to avoid presenting me work with careless typo's and spelling mistakes. Whenever I gently chide her for not taking more care with her work she is quite dismissive and says that near enough is good enough and that I am too pedantic.

Finally one day it was all too much for me and I told her that if she did not pull her socks up and improve the quality of her work I would be pulling her dress up and improving the quality of her discipline.

To my surprise she responded, "Fair enough," and went off to transcribe a short tape that I had just dictated.

About ten minutes later she came in to my office with the first draft of the document that I had dictated and told me that she had proofread it to make sure that there were no errors as she did not wish to cause me any further irritation. You can imagine my surprise at finding the client's name spelled wrongly in the very first line of the address. Without reading any more of the letter I handed it back to her with the warning that I would give her another chance to fix the errors before administering appropriate corporal punishment to help her avoid careless errors in the future.

She returned after a few minutes telling me that she was now satisfied that the letter was perfect, and she was confident that I would not find any errors. I got as far as the first sentence before finding the reference to the client's letter that I had "received" that morning. Six other mistakes in spelling or punctuation were also found.

I told Polly that she was to stay back after work when we would deal with what should be done about her unacceptable performance. She insolently responded by telling me that she had shopping to do and that our discussion would have to wait for a more convenient time. I told her in no uncertain terms that I was her boss and that she was to do as I directed and stay back after work, or else not come in tomorrow or any other day.

"I'm so sorry Boss -- I really need my wage and can't afford to be sacked."

"Well, in that case you will need to undergo my special obedience training course so I can be satisfied that you will be a suitable employee for me."

"Yes, I agree!" was her desperately blurted response, without even enquiring as to what that involved.

After others had left our section of the office that afternoon I called Polly into my office.

"I've given the matter careful thought, Polly, but I've concluded that your behaviour and attitude are not acceptable. I have decided to terminate your services."

Polly burst into tears, "I need my wage to support my mother. I can't afford to start looking for alternative employment, especially if you don't give me a satisfactory reference."

"Polly," I said sternly, "if you wish to remain in my employment you will have to sign an obedience undertaking which includes a voluntary submission to whatever form of corporal punishment I deem appropriate, as well as other disciplinary measures which I may decide are needed in your particular case."

Without further discussion the forms of undertaking and submission (which I had conveniently to hand in a nearby "private and confidential" file) were duly executed.

"Empty the entire contents of your handbag onto my desk," I instructed.

"Why ..." she began to ask, but before she could finish the question I interrupted her.

"Rule number one is that you must do precisely as I instruct you. You must never question my instructions."

She said nothing further but looked at me intently as I began examining the items on my desk. Polly's handbag contained the normal sorts of junk that most women seem to cart around but two items in particular caught my attention. One was a plastic-handled hair brush which Polly used to keep her hair shiny and well groomed; the other was a partly frayed power cord from an appliance that Polly had meant to take in for repairs.

"Return all these items to your handbag," I directed, retaining two items which had interested me.

"Please sit on my desk with your legs dangling over the front facing me," I said still sitting in my office chair right in front of her.

She looked puzzled but readily complied. She was wearing a reasonably well tailored outfit with matching navy blue jacket and short skirt, with a crisp white blouse. Polly's blue eyes looked at me demurely as she sat with her knees properly together and her hands on each side of her resting on the edge of my desk. The gap formed between the taut skirt and her thighs was obscured by a sagging fold in the looser slip beneath. Her legs were clad in body coloured stockings and her shoes were polished leather appropriately colour matched to the balance of her outfit. She observed me with slight bemusement as I cast my eyes over her sitting before me.

"Well, now what?" she shrugged after about a minute's silence.

"Polly," I said sternly, "please listen carefully and do exactly as I tell you."

"OK," she responded, with just a hint of impatience in her voice.

"Your first task is to recite a list of what clothing you are wearing," I said, "so that I can determine your ability to accurately describe things."

"You can see what I'm wearing already - you've just been staring at me for 5 minutes," she shot back impudently.

"This is not a good start, Polly," I said. "You have agreed to obey my instructions without question. I want you to describe what you are wearing mentioning each item in the order in which you would ordinarily remove it when you undress".

As soon as Polly had said "One pair of navy blue high heel shoes," I interrupted her.

"Remove them and place them at a 45 degree angle to the edge of the desk on your left," I directed.

Conscious of her close proximity to me Polly deftly squirmed slightly sideways tucking her legs up under the edge of the desk so that she could reach down and remove each shoe without having to adopt what I had hoped would be the more ungainly alternative of raising each shoe high enough in front of her for it to be easily slipped off. In fact so carefully did the shoe removal occur that I was unable to see any more of Polly than I could see before she moved, except perhaps for a half inch of slip which slid out from under the hem of Polly's skirt as she moved her knees to the right to bring her legs up under the edge of the desk.

"One navy blue woollen blend jacket with matching skirt," continued the listing without any prompting at all from me.

"Remove the jacket and place it over the back of the chair on the other side of my desk," I commanded, choosing a resting place for the jacket that I knew would require Polly to lean back and half turn around as my desk is fairly wide.

This time I was rewarded with a more extensive glimpse under Polly's skirt as she focussed her attention on arranging the jacket over the chair behind her on the other side of the desk. She was unable to prevent her thighs parting slightly as she turned around and lifted her knees over the edge of the desk to improve her reach to the chair. I was also able to gaze more intently in front of me while her head was turned away. Still, even this improvement in my state of knowledge did not go beyond noting that the stockings were pantyhose under which appeared to be some light pastel coloured panties.

(The centre crotch seam on pantyhose always seems to obscure useful opportunities to catch glimpses of girls' underwear. Quite an annoying invention from us voyeurs' point of view!)

Polly returned quickly to her more composed position and was sitting upright in front of me attentively awaiting further commands. Unlike before, she did not resume the listing and looked at me expectantly.

"What do you want me to do with my skirt?" she asked, as if it was the obvious next step in a pattern that she thought she had discerned in the way I was operating.

"Leave it for the time being," I replied, preferring to deal with items that could be removed without her having to move from her position in front of me.

"Please continue with your listing, Polly," I directed.

"One pair of skin coloured tights" came next.

"Are you sure you're listing items in the order in which they would normally be removed?" I checked.

"Yes," she confirmed, "I generally relax at home after work in blouse, slip and underwear. I take off my suit to stop it getting crushed and I've never liked pantyhose anyway although it's very convenient."

"Well then, we'll have to make you as comfortable as if you were home, won't we?", I asked. "Slip off your pantyhose but be careful not to snag it on the edge of my desk."

Easing herself off the desk Polly stood up in front of me only a matter of inches away and quickly lifted her skirt and slip just high enough at the sides to give her hands access to the waistband of her pantyhose. Awkwardly bending her knees she lowered them to the floor. (Bending over from the waist to lower her pantyhose virtually would have positioned her face in my lap and she did not appear keen to achieve that result.) Within a matter of seconds she had managed to step out of the pantyhose and re-seat herself on the desk in front of me. The bulk of the colouring that I had attributed to the pantyhose was obviously due to a healthy natural tan. She really had gorgeous legs.

"You can't just leave your pantyhose sitting in a small pile on the floor like that, Polly," I chided. "Please pick them up and place them in the left hand pocket of your jacket. You should take off your skirt too now please."

Again she surprised me somewhat by dropping to the floor and quickly walking around my desk to place the pantyhose in the jacket pocket as I had directed. Without awaiting any specific direction she slipped off her skirt and carefully folded it over the jacket already on the back of the chair.

"Stay where you are," I said sharply, causing her to look at me a bit puzzled. "I want you to move the chair back a little and lie face down on my desk with your shoulders level with my side of the desk."

"What about the listing?" she inquired in a voice now affected by a quiver of apprehension.

"We'll continue that later," I said. "For the time being do as you're told and make it snappy."

Polly duly positioned herself face down across my desk with her head unsupported about a foot in front of where I remained sitting. Due to the width of my desk her legs were supported by the desk to a point about half way down the calves and she seemed perfectly comfortable.

"You must remain absolutely still and silent," I commanded as I stood and positioned myself so that her now drooping head was between my legs and before me lay this well-proportioned young girl in white blouse and white slip awaiting my next move.

I leaned forward and grasped the hem of Polly's slip, slowly drawing it toward me so as to reveal increasing amounts of bare leg and thigh. I stopped just at the point where the crease at the base of each buttock joins the upper thigh, and before Polly's panties came into view. I noticed that her hands, that were lying down either side of her body, moved into a clenched position.

"Just relax please, Polly. I don't want you to tense any muscles unless I ask you to do that - is that clear?"

A slightly muffled "Yes" from between my legs satisfied me, concurrently with a visible relaxation in Polly's fingers.

I made a mental note of the static electricity that had made the slip cling to Pollies panties as I raised it. I placed my hands on Polly's slip over each buttock and started to feel out the edges of her panties that at this stage were still obscured by the slip. I was very gentle, and Polly obediently remained quiet and still. I then slipped my hands palms outwards between her upper thighs and gently parted her legs so that they formed about a 45 degree angle. I sensed a shiver run through Polly's body as I did this, but she knew better than to resist.

I undid my zipper to allow my penis to extend beyond the confines of my trousers and the glistening glob at its tip confirmed the arousal that I was experiencing. A drip dropped gently onto the nape of Polly's neck, but she did not appear to notice. I smiled to myself relishing the dominant position I was in and trying to keep the presence of mind to methodically think through what I wanted to do next.

Picking up the hairbrush that had come from Polly's handbag I ever so gently used its bristles to tickle her inside upper legs at the points just below where the hem of the slip now lay draped. A soft "Oooh" from Polly and a slight wiggle showed that her tactile sensors were alive and well. Turning over the hairbrush I grasped it by the handle and applied a short sharp and stinging blow to the soft flesh of Polly's inside left thigh. Her fingers clenched and her body tensed in anticipation of a repeat, but I was surprised that she otherwise remained silent. Being right handed a repeat performance on the right thigh wasn't as easy for me but the effect was no different at all.

Polly's breathing became audible and its pace had plainly increased. Still surprised by her silence I quickly raised the hem of her slip to her waist, revealing for the first time a pair of light blue nylon panties with white edging around the legs. They complemented the nicely tanned skin very well. Tensing of her muscles had caused a crease to form down the centre line between Polly's buttocks and I repeated my earlier suggestion that she relax.

Not noticing any compliance with that suggestion I ran my index fingers around each leg of her panties from the outside to the inside, and then drew the gathered material toward me forcing it into the gap between the buttocks like a G-string, and making her arse cheeks appear before me as taut but quivering jellies.

"Oh my God; I don't believe this is happening," was the first comment from my otherwise compliant subject.

"It is happening Polly and you had better stay quiet or the severity of your punishment will be increased," I shot back gruffly.

Without waiting for a response the back of the hairbrush found its mark at top dead centre of each buttock in a series of four quick whacks, two on each side. Although I had intended them to sting I was a little taken aback with the sobbing and shaking that my actions triggered.

"I've hardly begun, Polly," I said. "You had better lie still and quiet if you know what's good for you. It's plain to me that you have not had a spanking for far too long and your time has come."

"Please don't mark me," Polly whimpered, revealing a perspective that I had not really considered.

So far there was no evidence that the blows from the hairbrush had had any effect other than a slight reddening of the areas struck. These I thought were equally consistent with an excited rush of blood to the area and did not qualify as 'marks'.

"The consequences of your punishment are not my concern, Polly," I replied. "You will receive such punishment as I think appropriate. If evidence of that remains afterwards it will be for me to admire and for you to accept with humility, is that clear?"

During the silence that followed I picked up the appliance cord that was the second item retained from Polly's handbag. At the end that had frayed were visible wires and a plug that was barely holding on. I took it between my hands and ripped the plug from the flex leaving 2 strands of insulated wire which disappeared into a further sheath of plastic insulation that formed the outer surface of the cord. Raising it high I brought it down swiftly against Polly's inside left thigh. For balance it seemed appropriate to repeat the exercise on the other side. Sharp cries from the head between my legs indicated that this time some pain had been experienced. Within seconds the flesh that I'd struck changed colour to reveal a distinct mark corresponding to the width of the flex and the length that had made contact.

By now Polly had started to cry properly in substitution for the soft sobbing that had previously accompanied the hairbrush. Since she was in no state to carry on a conversation I applied a dozen more strokes in quick succession to Polly's buttocks and inner thighs with my newly acquired whip. (I wonder why people don't use electrical flex more often - it seems to me to be better than leather as it stings more). I then covered the exposed buttocks with her slip and sat back on my chair to contemplate the situation.

As I reversed over her drooping head the oozing from my penis was nicely brushed off by her fair hair. As I sat down the light caught the globules of semen on her hair and I found it quaintly amusing that she was oblivious to the spectacle.

Polly was still crying quite hard but gradually raised her head so that she was looking at me through red and tearful eyes that were certainly not the lovely shade of blue they had been when I previously saw them. Slowly she focussed her attention on my now placid penis dangling idly from the fly of my trousers. She made no comment but was clearly thinking of what I had been doing behind her back so to speak. It took a few minutes for the crying to subside enough for me to address the nicely disciplined young lady draped across my office desk.

"Polly," I said, "that was your punishment for the careless work you did for me today. As this appears to be the first time that you have been punished we will call it quits for the day. However, I want to see you in my office punctually at 7.30am tomorrow morning. That will be when you will learn more of the curriculum in my obedience training course. Now I want you to stand up on my desk and face in the opposite direction for me."

Polly gathered herself together and did as I instructed, with a somewhat dishevelled length of hair covering the back of her blouse and the hem of her slip about 6 inches above my line of sight.

"Place your feet about a foot apart please Polly," I commanded, speaking with an authority that seemed like it had existed for ages rather than acquired in the space of about half an hour.

Her due compliance without comment or resistance pleased me. She did not appear to be as impudent or insolent as she was earlier in the day, and I felt that the punishment had been firm but fair.

I stood up placing my head under Polly's slip and gently ran my fingers up her inner thighs, detecting ever so slight welts that must have formed after the strokes of the electrical flex had been directed there. I also gently withdrew the still tightly drawn panties from the gap between her buttocks and restored them to a normal position.

"I am pleased with you, Polly," I said as I withdrew from under the slip. "In the circumstances you have accepted your first spanking rather well. Please turn around and, grasping the hem of your slip with each hand, raise it high enough to hide your face."

Again I was rewarded with unfaltering compliance and took a fairly leisurely opportunity to now inspect Polly's panties at close quarters from the front. A small damp patch toward the front of Polly's panties left me wondering whether it was excitement juices or whether she had briefly wet herself from fear.

"You know, Polly, that static electricity is bad for the computer equipment in the office, and static electricity is associated with synthetic underwear like you are wearing. I don't want you to wear nylon any more, is that understood?"

"I have some cotton panties and silk slips if they would be acceptable," offered Polly, reverting to her demure voice.

"I will need to inspect any underwear and approve it in advance from now on, Polly. Please bring with you tomorrow morning when you come to see me enough of the underwear that you propose to wear for the rest of the week to enable me to select items that I regard as suitable. That will be all for today. You may step down and get dressed. Use the mirror in my coat closet to adjust your hair and makeup before you leave my office. It goes without saying that your punishment this afternoon and future obedience training sessions are to be kept absolutely confidential. The slightest transgression will result in immediate dismissal without notice - is that clear?"

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