Becoming Miss Ashley's Pet

Chapter One - Charles

Chapter One - Charles

How could such a perfect scheme go so awry?

As I obediently heel, vigorously shuffling on all fours to stay in position at the precise location behind Miss Ashley’s right side, listening to the humiliating chiming of my testicle bells, I reflect back. Occasionally glancing upwards under Miss Ashley’s flowing skirt, I catch glimpses of the fine smooth pink flesh about which I first fantasized some five years ago. Miss Ashley is known to forgo undergarments when relaxing with friends and the view from down here, head and shoulders just above the level of her knee, brings memories.

It is New York, 1997. A fine spring day in Battery Park I am enduring the drudgery of apprenticing in the legal profession after many years studying at Columbia University School of Law. I am young, handsome, attracted to the fairer s*x but with little time. I am at a point, after some three years as an associate at a prestigious law firm, where I cannot envision spending my life reviewing legal documents for the missing dotting of an ‘I’ or the failure to cross a ’t’.

I steal time for a quick hot dog in the park. And there sits a beautiful girl. She wears a loose skirt and unwittingly flashes a hint of her charms when she switches the crossing of her legs. Quickly thinking, I decide to approach and act the role. A chance meeting in the park of handsome young attorney and nubile young woman. Her decorum, her attire suggest she is seeking companionship but doing so in that most coquettish yet judicious way, avoiding eye contact, pretending not to notice that I have noticed.

I sit and of course comment on the weather, a warm and sunny day after many weeks of snowy March rain. She nods aloofly also playing the role. We talk. She is demure, seeming to pose as a mere secretary or lowly member of a typing pool. What she does not realize is that I know her to be Miss Ashley Duval. She spent the morning in the offices of Samuel L. Brackett, the estate attorney of our firm. She did not notice me but I of course noticed her and her divine appearance mandated that I undertake the bachelor’s investigation.

The secretary of Samuel L. Brackett, the punctilious Miss Priscilla Peck, divulged all, explaining that the aunt of Miss Ashley Duval had passed on and she, as sole heiress, was there to learn that many more millions would be heaped upon Ashley Duval’s already moderate wealth and layer upon layer of trust income.

“The poor girl has no one,” the frumpy Priscilla asserted, seemingly with genuine sympathy. “All living relatives are gone.”

“Tsk, Tsk,” I recall empathetically offering in disguising my zeal.

Yes, with financial resources approaching the range of ten digits, possibly well into the ten digits with sizable blocks of stock discounted for estate tax purposes, I could only express gratuitous pity.

Where would all that money go?

So when I spotted Miss Ashley Duval in the park, I schemed. Other than her prettiness, she blended with the masses. It quickly became evident to me that she either did not desire to flaunt her new wealth or had not yet learned to do so. But that’s New York... the density offers concealment... the anonymity of the many providing camouflage for the celebrity of the few.

I don’t recall everything I said but certainly did not reveal that I had knowledge of her name and ‘unfortunate’ circumstances. ‘Ashley’ was her simple reply when I introduced myself as Charles. Still I turned on the charm, scheming from the very start. After all, those millions upon millions needed to go somewhere. Why not to the benefit of a jaded attorney?

We exchanged phone numbers. And why shouldn’t she be forthcoming? It was reasonable to assume that every date she had was with some gigolo pursuing her money or some foppish trust baby in evening jacket and ascot, pushed by an overbearing mother to attempt a relationship. In her mind, I was someone different... attracted to her person, her looks, which I was. But countless millions certainly improves one’s appearance.

Thereafter, we talked on the phone several times. I went slowly, never revealing that shortly after that encounter in the park I took the time to review Samuel L. Brackett’s memos floating about the steno pool. I also pumped away at Miss Priscilla Peck. A graying spinster of some fifty years, the lonely old gal seemed delighted that a young handsome associate would choose to engage in casual conversation. Any attention she received brought a warming smile and a subtle expression of gratitude. And on occasion her eyes would flash revealing a hidden lust, possibly for me, possibly for any virile male. When not working, one envisioned her sitting alone on cold evenings wrapped in a shawl and sipping a cup of herbal tea, reading some cheap romance novel.

With her hidden desires, I played her like a fiddle. So she talked and talked revealing much confidential information to a person she perceived as a trusted young attorney with empathy for the orphaned Ashley Duval, the naive and unsuspecting Ashley Duval, the fabulously wealthy Ashley Duval.

Within a week I knew more about the finances of Ashley Duval than she did. Even the ownership of the tropical island, which our cagey estate lawyer had listed as nominal in value.

‘No comparable valuations’, Sam had noted in summarizing the appraisal of the island in the lengthy list of Miss Ashley Duval’s assets. I could only imagine the true value of 5,000 acres proximate to islands known to be the most expensive vacation destinations in the Caribbean. My eyes gleamed at that point. Miss Ashley Duval was by far the richest unmarried woman in the world, and she was alone, and pretty, and seemingly detached from the cognizance of her fiscal circumstances.

She needed me, I deduced. And admittedly, it was a self serving conclusion.

“Corky need to go?”

Miss Ashley’s question snaps me from my reverie. The plantation house is within sight and Miss Ashley asks the obligatory question. With my modifications, relieving oneself outdoors is neater than requesting the assistance of one of the household maids when indoors or imposing on someone to take me out for a walk.

I sheepishly nod, causing the collar to somewhat aggravate my neck.

“Over here,” Miss Ashley directs, drawing me from the well worn path into some low growth vegetation.

“Position,” she simply commands.

I part my elbows and lower my face and head to where my chin touches the soil. I widely part my knees then arch my back as trained thrusting my buttocks upwards. I feel the tender fingers of my Master, Miss Ashley Duval, graciously detach the small chain connecting the metal band encircling my scrotal sac to the anal insertion and tail. This serves to reveal my pee hole, the surgical opening in my perineum where my urethra now empties the contents of my bladder.

Yes, I now squat to pee.

Miss Ashley stoops and uses the obedience stick to push forward my balls, permitting my flow to splash to the ground unimpeded. Her free hand caresses my neck in relaxing me. Though her divine touch stimulates I know to concentrate on the task at hand. I do not need to turn my head to know that the many visitors watch with a combination of amusement, curiosity and Schadenfreude.

“Come, come,” Miss Ashley gently encourages. “Be a good boy.”

Having been well watered by Big Sam shortly before the jet’s arrival, my bladder is indeed full.

With Miss Ashley’s verbal inducement I do not disappoint her guests. I flush with embarrassment but perform for my Master. Goose bumps again form as my flow splatters to the soil. I am indeed a good boy.