tagBDSMDiary of Ms. Pennington's Assistant

Diary of Ms. Pennington's Assistant

byJMaxwell69©

Preface:

I, Reginald P. Walcott, am a 37 year old professional bitch-slave, and until recently worked in the service of Ms. Beatrice Pennington of the law firm Kale, Pennington, and Shipwright. As of this writing I am approaching what would be my tenth year anniversary in this line of work. How, one might ask, does one become a professional bitch-slave? That is the question to which I have turned my attention in this prologue and the collection of diary excerpts that will follow. This diary was, I think, an attempt to make sense of the life into which I found myself bound.

My résumé, which I have unfortunately had cause to circulate recently, does not list my most recent position as "bitch-slave", but instead refers to me as a "Personal Assistant." I have a wonderful letter of recommendation in hand that not only refers to me as an "assistant" but also plays up the more professional business activities I occasionally engaged in. However, it has only been quite recently that "Personal Assistant" has become an apropos title. To be certain, the transformation to abject servitude doesn't occur overnight. It is an evolution that is arrived at through a series of compromises that have been interpreted as the valuation of security over pride or the acceptance of complete and utter servitude as the price of not being lonely. One gives an inch, and a foot is extracted. Each compromise signaled to my mistress a lower plateau to which I was willing to sink - all for a price that was pocket change to her. My mistress used this gradual approach, and it made me forget that I once had boundaries and that there were once actions taboo. If my mistress had tried to test my limits all at once I might have remembered that I was a person, and the primal attachment I had to her would not have yet been forged. I don't know why I succumbed to all the demands made of me by Ms. Pennington. Fear, insecurity, guilt, loneliness, or secret urges in the dark recesses of my subconscious mind, any or all of these may have been responsible.

There is a brief answer to the question of how one becomes a bitch-slave. At least I can say how I came to this career path. I worked in a job that involved nearly no self-satisfaction, but, instead, consisted of menial tasks done entirely for the benefit of others. However, it is not enough to just work in such a position, but one must do it exceedingly well. I thought I was invisible, but there were those who noticed. Good bitch-slave material is, apparently, not easily come by. Soon another person was offering me almost twenty-five thousand dollars more a year for what seemed at the time like only a marginal increase in debasement.

Why the term "bitch-slave"? Personally, I believe that Mistress Pennington favored calling me a "boy-whore" or "boy-slave". From my perspective, "whore" was more apropos in that I got paid for my service. From Pennington's perspective, "boy-whore" presented the additional benefit of ridiculing me as underdeveloped as a man.

Without further ado, I will present you with some illustrative excerpts from my diary so as to give you insight into my talent for subservience and how I came to develop it.

July 28, 2000:

I received a call today from a secretary at one of the best law firms in town. She said that her employer, Ms. Pennington, had been told that I was a loyal and competent assistant, and was looking for someone to replace an employee who had recently been terminated. She asked if I would be interested in interviewing for the position. While "loyal and competent" made it sound like I was a mediocre dog, I was open to any change that might provide some break from my depressingly mundane existence. The secretary cleverly intimated that Pennington would be willing to offer a salary considerably greater than my current wage. I said I would gladly take the interview.

The secretary gave me the home address of Ms. Pennington, and told me to be there at 9:00am on the following Wednesday.

August 2, 2000:

I have a good feeling about my interview.

I tried to size up Ms. Pennington as an employer the same way she was clearly sizing me up as a potential employee. I suspect she did a better job of this than I. I had trouble getting a read on her beyond the superficial, and even at that level she was a study in contrasts. She is a natty dresser. She wore an expensive pinstriped pantsuit over an ivory blouse. It all looked crisp, as though she had never worn it before. Her prematurely silvered hair was worn in a tight bun, and not a single strand was out of place. She's a bosomy woman, and the low open neckline of her blouse showed off her impressive and considerable cleavage. Here was the first ambiguity to be reconciled. That is, the contrast between the schoolmarm hairdo, the Wall Street ensemble, and the barely contained fleshy orbs that were straining to break free from the blouse.

Her demeanor was stern, but yet she seemed to have a sense of humor. She spent a number of minutes making infinitely clear that this was a personal assistant position and was paid for from her own funds. Therefore, I would be expected to conduct tasks that would be beyond the scope of work of a person hired by the firm. She said she had had to let five previous Personal Assistants go because they eventually refused to do personal chores she assigned them. I indicated that I understood that I would have to pick up her dry cleaning, get her coffee, and perform any number of other chores that secretaries tend to get chaffed about doing because they are not related to the firm's work. She then turned the conversation on its head and asked me to describe precisely what I was unwilling to do.

I said, intending to convey a little levity, "Well, I wouldn't commit a homicide."

Pennington paused a moment before showing her own dry jocularity. "Those terms are acceptable." Shortly thereafter she dismissed me...

August 3, 2000:

Pennington's secretary at the firm called me. She asked if I was still interested in a position as Ms. Pennington's personal assistant. I said I was.

She told me to report to Ms. Pennington's home at 8:00am on Monday the 7th...

August 7, 2000:

I got to Ms. Pennington's about 15 minutes early, and I decided to wait a few moments as she seemed the kind who would be just as displeased with too early as too late. I hoped no one would call the cops as I loitered outside the wall of Pennington's estate. This was a neighborhood of multimillion dollar homes. Even in business attire, loitering around outside someone's house might attract attention.

The wall reminded me of Pennington's cleavage. It was a salmon stucco wall with deeply plunging downward arches that were filled in by ornate wrought iron bars. It was consistent with the plantation hacienda theme of the building's exterior. At any rate, if one looked at two sections of the wall it took the shape of a couple ample bosoms.

At five minutes till eight, I poked the button on the intercom.

"Jess? Ouw may I help you." It was the housekeeper, Juanita, whom I had met on the day of my interview.

"I am Reginald Walcott, Ms. Pennington's secretary told me to come in this morning to start a personal assistant position."

"O-kay. Come in." An electronic buzz and metallic click punctuated her sentence, and I was able to push the wrought iron gate open.

When I got to the door, Juanita opened it and stood aside for me to enter.

"Chee is in de bedroom." Juanita said and motioned for me to follow.

I thought the matronly live-in maid would take me to living room to wait, but, after passing from the foyer through a dining room set for twenty and past a tidy but well-stocked library, we entered what was clearly a residential wing of the building.

"Der you are. Have a nice day." Juanita motioned to the door in front of me.

"Isn't there someplace I should wait for Ms. Pennington?" I inquired.

"No, she would like to see you." Juanita said and waved the backs of her hands at me with an urgency and exasperated look that indicated that I should be moving along now.

I wrapped tentatively on the door, uncomfortable with visiting the boudoir of my female boss so early in the morning. I feared that Juanita incorrectly interpreted Pennington's wishes, and now I would get in trouble for it.

"Enter." Pennington commanded.

I meekly did as I was told and found Pennington in a white dimpled cotton robe sitting at a small table next to one of the room's windows, which were exceedingly tall taking advantage of the high ceilings of the old mansion. Her hair was still wet and cascaded down in graceful undulations to just below her shoulders. While her hair was gray it was also thick and lustrous.

"You are late." Pennington stated.

I consulted my precisely set watch and found that it was now a few seconds after 8:00am. The watch was the one possession I owned that I couldn't really afford. From cuff to finger tip I might be confused for one of the fabulously rich and famous. It had taken five minutes to negotiate the front lawn and to meander back to the farthest reaches of the house. "I'm sorry. I got here early but didn't realize it would take so long to navigate your estate."

"No excuses, just don't do it again. I suspect it shouldn't be a problem from now on because you will be here an hour earlier so that you can get my coffee, bring me my paper and said coffee, and draw my bath before I get out of bed. Juanita will give you a key and your own code for the alarm in case it is ever still set when you arrive. Do not let it go off under any circumstance. Understand?"

"Yes ma'am." I replied subserviently.

"Now grab the dryer and hairbrush and make yourself useful." Pennington ordered as she turned back to her paper.

There was a master bath through a door off her bedroom. Everything meticulously neat and in its place, and it was not hard to find the cordless hair dryer and a hairbrush. I returned to where Pennington was sitting and stood waiting. She snapped her paper back into a folded position. Her only other concession to facilitating my allotted task was to lean sharply over in the chair so that her hair hung freely. I began to brush through her hair with the brush in one hand while moving the dryer with other hand an in up-and-down motion. It was my best, yet uncoordinated, attempt to emulate the stylists I had seen though plate glass windows as I walked around the city. I had little experience with hair brushing and drying as my own hair was kept quite short as part of an overall clean-shaven motif that I displayed, and which I suspect factored into being offered this job.

"Less heat, and not so close." Pennington commanded. I understood her concern. Her hair had a shampoo ad quality about it that she wouldn't want some novice ruining.

I turned the heat off altogether and backed the dryer away a little. I was doing much better until I got momentarily mesmerized by an unexpected sight. In leaning over from one side to the other, the lapel of Pennington's robe had puckered outward, and I found myself looking at the full outline of her pale, soft, and gracefully convex breast. Pennington seemed unfazed by her immodesty, but I was snapped out of my ogling when she commented that I was dawdling in one place too long.

It occurred to me that it would not at all do to be caught staring at the boss's boob on my first day. I did not want to establish myself as a pervert. As I was splitting my awareness between the task at hand and worry about getting fired on my first day and the indelible mark on my resume that would result, Pennington turned her chair 90-degrees and leaned forward throwing her hair from back to front so that it hung down such that her face was obscured. I knelt down to adjust to her now lower form.

From this lower position there was no escaping notice that both of her pendulous breasts hung straight down like her hair, but one of them had managed to escape its confines altogether and was now entirely outside the loose "V" of her lapels.

"You have beautiful hair." I commented to break a silence that had lasted too long, and to distract myself from starring at the lovely breast.

She did not acknowledge the complement, but instead gave another command. "In the top drawer of that dresser are bra and panties, bring me a pair of white cotton."

I turned brusquely to obey the command, figuring that I would give her an opportunity to tuck the errant breast back into her robe. I put the dryer and brush on the dresser and opened the top drawer. The fastidious order of the drawer's contents made it easy to find a pairing to fit her description.

As I turned back around, I was stopped for a moment in my tracks. My previous concerns were made moot. Ms. Pennington had assumed a standing position and was in the process of shrugging out of the robe. She draped the robe over the back of her chair, and was standing stark naked in front of me. I quickly averted my eyes as I brought the undergarments toward her from across the expansive master bedroom. Was this trap, a test, a seduction? It turned out to be none of the above.

"Why are you looking at the ceiling? Are you trying to tell me that I am so repulsive that my nude form makes you look away?" Pennington inquired.

"No, not at all. You're a..." I broke the sentence off because I was completely at a loss as to how to finish it in a manner that wouldn't incriminate or offend. It was true that I did not have any trouble at all looking at the nude Pennington. For a woman in her mid-forties, she was attractively built, and was elegantly proportioned for a woman with such impressively sized and shaped breasts. While she was not like the celebrity 45 year olds who had the preternatural bodies of 23 year old Pilates instructors, neither was she by any means unappealing. Yet, I didn't think that complementing the physique of my nude boss was a strategically sound maneuver.

"I'm a what?" Pennington did not let the sentence drop.

"I just thought you might like some privacy." I replied.

"Oh, I see. You are under the misapprehension that I care whether you see me naked, or about what you might think about my naked form. Let me assure you that I am completely indifferent. If you were a... a man, that would be different, but you're just a servant." Pennington said.

While I found that to be emasculating phrasing, I assumed she had just succumbed to ineloquent word choice. What she meant to say, I consoled myself, was that, because there was no possibility of romantic interest between us due to our professional relationship, she was not bothered by me seeing her naked. That is what I hoped she meant any way, but part of me suspected I was rationalizing her rude behavior.

She stretched out her arms before her. I thought for just an instant that she might be offering me a half-hearted hug, but then realized she was just allowing me to slip on the straps of her bra. I couldn't believe that she was really expecting me to dress her. I was so flustered that I started the put the bra on the wrong side up. Slipping on the bra wasn't challenging, and neither was hooking it. However, the part in between that involved getting her breasts into a bra cups with minimal manhandling and groping was no easy task, particularly because Ms. Pennington was so amply endowed. I moved slowly, hoping that she would take over when I got to the point at which she was uncomfortable with a complete stranger handling her bare breasts, but that moment never came. I finally just took the risk. I lifted her twin orbs into cups, and smoothed the fabric under them. I hooked the bra, and then realized I had her panties looped over my wrist.

I knelt down, and she lifted her feet one at a time so that I could align the leg wholes, and then I pulled the underwear up. By now I was getting over the initial shock and I ran a finger under the elastic across her butt cheeks to make certain they were comfortable and not binding. It seemed unlikely that the back of my finger brushing her ass was going to offend her at this point. I did the same in the front at the crease of her hip.

"Come. You'll hand me pins." Pennington commanded.

I followed her into a palatial master bath. It was massive and every square inch was tiled with, no doubt, some rare form of marble. At one end there was a shower big enough to accommodate about 10 people simultaneously, and that had three levels of shower heads on each of three walls. At the other end there was a hot-tub sized bath on a raised platform. Perhaps three people could fit comfortably in the tub with its tightly-spaced pulsing jets. We took up position at the twin lavatory sinks that were midway between the shower and bath and that were suitable for hordes but used by only one. In the European style, apparently the toilet was in a different room all together.

I was happy to see that she didn't expect me to do her hair, as I would have no idea how. She only required me to hand her the bobby pins that she used to put it up in the same tight bun I had seen her wear on the day of my interview. It was one of the many enigmas of Ms. Pennington. She had beautiful hair, but yet she wore it so that no one could possibly tell. If she had displayed a proclivity toward modesty all around, I could have more easily grasped it. However, her confident display of cleavage belied modesty.

"Are you ogling me Reggie?" Pennington asked.

I had been. I was not looking directly at her, but rather at her reflection in the mirror. What did this woman want? If I looked away, she gave me a fit; and if I was caught staring into her cleavage, she also rebuked me. I didn't know what to say, so I just said. "Sorry, Ms. Pennington."

She went on about her business as if nothing had happened. I made a mental note to make this my go-to strategy. Don't make excuses, don't argue, just apologize.

The rest of the day was decidedly less unusual...

August 8, 2010:

I added 15 minutes to the one hour earlier that I had been told to show up. I let myself in with the key that Juanita had given me, and, fortunately, Juanita was already up and about and the alarm had been deactivated. I had memorized the code and procedure for disarming it the night before just in case, but was still afraid I was going to set it off. It was the one offense that seemed like it would be beyond being rectified with a simple apology.

Juanita was a godsend in that she was a font of useful information. Despite having the humorless appearance of a Tijuana women's prison guard, the woman was extremely helpful in aiding my navigation of the minefield that was Ms. Pennington. Perhaps the most helpful of her tips this morning was about the timing and coordination of the coffee, bath, and wake up Trifecta. If the timing was off by a little, either the coffee, the bath, or both might be too hot or too cold for Pennington's taste.

Juanita knew Pennington's rhythms, despite the fact that she apparently went to great efforts to minimize her contact with the woman. Juanita confided that, while she had worked for Pennington for 15 years as a live-in servant, she frequently went days without more than a passing glance at the woman. The secret, she said, was to be incredibly fastidious. If Pennington could always find what she was looking for and everything was clean and orderly, then the only time Juanita needed to see Pennington was on the relatively rare nights when she was home early enough to need to be served dinner.

After drawing the bath, I went back to the kitchen and brought back the coffee piping hot in a thermos with a cup on the side. Ms. Pennington did not like to awake to harsh sounds. This was part of the reason that letting the security alarm go off was one of the few mistakes that seemed to result in automatic firing. It also meant that an alarm clock was not an option. So I gently approached and put my hand on her shoulder. I rocked her gingerly as I repeated "Ms. Pennington" in a forceful whisper.

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