Ah, that further explains her aloofness concerning Jack and his care.
“Why are you telling me this?”
“I like the way your boy is cut. So cleanly... and he’s of nice size. He’ll find me to be very caring...”
Ah, Lips Louie seems to be a serial fellator.
“Well now that I know, why should I offer...?”
“You’re not curious as to Mrs. Lipton’s precarious position?”
Yes, mentally I skipped over that, my thoughts focusing on Jack’s legitimacy.
“What about it?” I blurt with impatience.
Lips Louis smiles coyly.
“I’ll make it long and pleasurable for him. I’m very good. And I think you will greatly benefit from what I have to say... afterwards”
I step back, arms akimbo in more thought. Jack has no CFNM party next weekend; I’ve spent so much time preparing for this Soho soiree. If the information is as relevant as Lips Louie suggests, it may be worth having Jack’s scrotum drained for the cause.
“Next Saturday. Hire a limousine. I have a service you can call. You will accommodate Jack orally as you tour the city. Afterwards we’ll talk.”
Lips Louie nods in excitement.
“Are you going to have him ejaculate for us?”
“To bring him to fully spurt is another $300,” I firmly declare in my stentorian businesswoman’s voice
Chapter Thirty-Seven
Poor Jack. Either the patrons of the Soho club are a cheap bunch, or they were so preoccupied with getting their own rocks off that they cared not to watch me masturbate Jack.
No $300 offered for jerking him off!
An alternative supposition... none had an interest in me as female doing anything. For other then interacting with Pattie concerning initial payment and conferring with Lips Louie, no one talked to me. I even had to shout at the bartender for a drink, my presence tolerated due to Jack’s fine priapic exhibition.
So it’s Sunday and Jack is entering his third week of chastity... moaning and pleading for climactic release.
Well, I promised him a milking. And he will get it.
From deep in my closet, I dust off my masturbation harness, used many times with Jack’s predecessors when, as a young governess, I found that masturbating some obstreperous boy quickly brought calm and altered comportment.
Waist belt with cuffs attached, thigh straps and neck collar. It humbles and positions a boy for long, slow, controlling strokes of a young penis.
Due to Alice’s fine handiwork, I can dispense with the neck collar, Jack’s more or less permanently in place.
Since it’s to be a milking, not outright masturbation, I can withhold any hand work. But I will need a vibrating anal insertion and a simple wooden dowel.
I clear off the kitchen table, thinking that Jack should be more wary of that for which he pleads.
“Jack, come into the kitchen,” I instruct as I have an additional thought. “Mount the table. Lie so that belt is about your waist,” I further instruct as I fill a bowl with warm water.
I have not lost my prowess, quickly encircling Jack’s waist and securing his wrists within the attached cuffs. Hands restrained.
I next release him from his cock cage, unlock the Prince’s Wand and slip away.
Straps with short tethers next circle his thighs just above the knees. I will milk Jack in the uncomfortable position, a very subordinate pose, mindful of being diapered as a toddler.
“Knees to your chest, Jack. Governess Kelly is not going to use up her relaxing Sunday mornings stroking your penis.”
He complies, of course, and I quickly attach the tethers to his neck collar, holding him supine, wrists restrained, knees to chest.
During my tendance, Jack slowly hardens of course, his long interval of chastity cruel, his system deluged with hormones. Just as when I cleansed him as a boy, I become clinical, ignoring his engorged condition, and work toward the goal of draining him... ever so slowly draining him.
He’s expecting the grip of my firm but gentle hand. He will receive elsewise.
I lubricate his anus. Again he expects the insertion of my fingers. Instead I slip within a rather stout probe with wires attached. When switched on it vibrates, Jack never before being so mechanically manipulated.
Lastly comes the bowl of soothing warm water. I place it on the table, lift his burgeoning scrotal sac and dunk it. Jack moans with the faint soothing delight.
He does not fully comprehend his treatment, all new to him. Yet he’s expecting pleasure, and in a way he’ll receive it... but it will not be the ecstatic pleasure the male beast covets.
“An hour or two should do the trick Jack, enjoy,” cruelly bending down his stiffness past his upturned thighs.
There I press the dowel against the back his thighs, horizontal and parallel to the table top. Against this slim length of wood I press the tip of his now raging penis. It’s wedged in an angle of denial. The organ’s need to right itself... desperately right itself... holds in place the dowel.
“It hurts Miss Kelly! I can’t stay like this!”
“Well, do the best you can,” I callously suggest, flipping the switch for the anal vibrator.
His penis cannot ejaculate held at such an angle... but it will ooze... and in fact fluid is already streaming. Yes, he will remain hard, the vibrator spurring stiffness, his subservient psyche broiling, his hormones overflowing.
“You’ll find if you squirm a little, roll your hips about, you’ll get more flow. But one way or the other, with the pressure and caressing of your prostate, you’ll be drained of all that build up.”
With that I step away, the Sunday papers beckoning...
Chapter Thirty-Eight
Halfway through the New York Times, the apartment doorbell rings. It can only be an internal visit, not having been alerted to a visitor by the security desk.
A tenant in need of emergency toilet cleaning?
I arise to respond. Pulling open the door, it’s Theresa. She is imposing in her uniform, as stated a very large and muscular woman of color.
“A package. Came yesterday but you appeared busy directing Jack on a leash,” she hands me a thick padded envelope. I know it to contain a replenishment of Jack’s testosterone.
“Thank you, Theresa.”
“You fixing something in the kitchen?” she inquires apparently hearing the buzz of Jack’s vibrator.
“No, I’m milking Jack. I’m a little worn pulling him about the city last night so I’ve dispensed with the usual manual effort.”
In being locked in his cock cage while serving Theresa, it dawns that she has never seen Jack’s somewhat impressive male equipment. And sure enough, her curiosity is piqued, inquiring before I can offer.
“That seems interesting. Can I see him?”
“Of course,” fully aware of Jack’s heightened humiliation in having a woman view his helpless state of bondage and exposure.
I lead to the kitchen where Jack remains on the table in the forced fetal position. It’s been nearly an hour since I turned on the anal vibrator. Yet sure enough Jack remains stiff as a board, the slim wooden dowel functioning to hold his erection at the awkward and most frustrating angle. Fluid streams in abundance, glistening in the kitchen lights. And as I suggested, Jack squirms, bucking his hips in a manner of faux copulation, appearing to be making love to the kitchen ceiling.
“He’s a big boy! And so nicely cut,” bringing me to beam with pride.
“Yes, I circumcised him quite carefully, assuring a nice high and tight cut. Lots of foreskin trimmed.”
We speak as if Jack is an object, ignoring his occasional groans of faint pleasure.
“He’s quite fecund,” a knowledgeable Theresa commenting on the cloudiness of the thick discharge.
“No orgasm, ruined or otherwise, for two weeks. I took mercy on him. Plus it’s best not to go too long without rebalancing the hormone levels.”
Theresa steps forth, Jack blushing with the i
ntensity of his degradation. Her index finger goes to the base of his wet erection and slowly draws upwards to the tip; I’m sure bringing a brisance of delight to an otherwise slow and mind boggling subtle extraction of essence. She then lifts her finger, coated in man juice, and assesses.
“Lots of spermatozoa. Good of you to relieve him.”
With that Theresa shifts towards Jack’s face, high neck collar denying him much motion. She wipes her finger clean on his upper lip and laughs.
“See you Tuesday, Jack,” finally acknowledging his presence.
Jack again bucks his hips, seeming to offer his stiffness to Theresa’s hand. She laughs.
“Have to get back to the desk. Nice to see him unlocked. You’re quite kind to him.”
Chapter Thirty-Nine
Later that afternoon, I note Jack is finally drained. I release him.
“I thought you would masturbate me,” pouting like a child, any joy sensed quite faint.
“No, Jack, masturbation is for a woman’s pleasure not for yours. I will decide when and before whom you are to be climactically relieved of your sperm.”
The week progresses, Jack’s calendar filled with the more mundane but psychologically important toilet cleansings. In walking the city streets in colorful dress and sandals, the high leather neck collar brings even more attention... unwanted attention. Therefore there is little dawdling, Jack moving rapidly from appointment to appointment.
Saturday comes... the prospective limousine ride with Lips Louie.
The randy cocksucker follows up. And once again the pretentious white limousine awaits before our building.
For this afternoon jaunt, I must have Jack prepared to receive the attention of Louie’s hyperactive lips, but certainly not his own hands.
I thus once again put to use the masturbation harness, just the waist belt and attached wrist cuffs which will immobilize his hands. I then release him from his cock cage and Prince’s Wand. Lastly comes his covering. Jack will wear his white toga, the loose bottom portion easily offering access to that which Lips Louie covets. And I will lead him to the building lobby with matching white leash.
By phone we agree that Louie will take a spin through Central Park, the passenger compartment well partitioned from the driver for privacy, then phone me when the long afternoon of fellatio has ended.
I am curious concerning his comment about the vulnerability of Mrs. Lipton... her so termed precarious position.
Jack is apprehensive, of course... an afternoon with a man... if such gender can be ascribed to the image of a naked Louie in pink ribbon, bow and make up.
“I don’t want to do this, Miss Kelly,” poor Jack expressing reservation as I lead him to the elevator.
“Shush. It’s for the best, Jack. Lips Louie may be a source of valuable information.”
And so it’s to the lobby and out to the sidewalk. Through the open door of the limousine I hand Jack’s leash to the eminent... formerly eminent... Louis J. Welkeyser III... no longer esquire.
I am concerned about Jack, but take no pity. After all he will finally ejaculate... no ruined orgasm... no jeering women... humiliation yes, but since it’s a completely foreign ilk such should thrill.
I return to my apartment, updating the Craig’s Listing, offering Jack’s chiseled form for CFNM parties.
Chapter Forty
It’s two hours later that Lips Louie calls on his cell phone to announce mission accomplished.
He must be quite the cock tease if he kept Jack on the edge for such a lengthy interval... doubt if the Park scenery brought delay.
I descend to the lobby, stepping to the sidewalk. Lips Louie and I must talk, but I am not going to have him in my apartment. When he returns Jack’s leash I guide my pet to the front passenger door.
“Ride with the driver, I need a private conversation with Mr. Lips.”
I enter the rear compartment, sealed from Jack and the driver and take a seat opposite Lips Louie.
“I assume he got off for you,” I smirk.
“Like a cannon. He’s exquisite, quite the hunk. Quivers nicely in being handled by a man.”
I mentally question his gender reference but remain silent. I want information not a confrontation.
“So, Mrs. Lipton...” I prompt as the driver pulls from the curb.
Louie downloads.
“What I am going to say breeches the tenet of attorney client confidentiality. But one can only be disbarred once,” Louis begins with a sheepish grin.
“Working on Mr. Lipton’s estate had some curious quirks. The first being that the will was specific that Jack, his biological but illegitimate son, was bequeathed nothing... not a cent. His wife was to receive the bulk of the estate, quite sizable, in the low nine figure range. Yet another quirk, if his wife predeceased him, the estate again was still not to go to his son, but instead to some large prominent charities... American Cancer Society... United Way... all that stuff.
“Again very specific concerning parsimony for Jack. It became evident to me in working with Mrs. Lipton that she had great disdain for Mr. Lipton’s son, an object of scorn in being conceived by a woman of ill repute during their marriage. The possibility dawned that the will’s unusual aspects were drafted under duress. Estate lawyers normally suggest leaving some token amount to undesired heirs to counter an argument of oversight in drafting the will. Instead for the son, second to the wife in having any potential estate claim, there was nothing.
“I envisioned an undisclosed confrontation, Mr. Lipton most likely wanting to leave something to his son, but the scorned Mrs. Lipton opposing, in her mind such a provision giving the son the legitimacy she forever wanted denied to him. Apparently marital bliss trumped standard will drafting. Mr. Lipton obliged. Illegitimate son denied all.
Why would he so willingly concede, I kept asking myself? With his money he had influence; surely there was something to placate the wife’s wrath.
“And then it dawned. The will left his estate to his wife... not to Mrs. Lipton by name. A clue! And so I did some research... research of which I am rather proud. It seems for Mrs. Lipton there had been a prior marriage. She was a show girl. From what I could deduce some ostensibly wealthy patron of a Las Vegas casino proposed marriage, possibly in the midst of a drunken binge. I’m sure he hinted at riches, offering a life of luxury and full luxurious attire rather than the skimpy Las Vegas garb of silk and feathers.
“Well it was a ruse... who conned whom sort of thing. He got laid, Mrs. Lipton got nothing. The man was broke. Presumably there was a quick divorce but I could find no record of it.
“So with curiosity piqued, I tracked down the con artist first husband, rather easy with his subsequent criminal record. I suggested I needed to contact his wife. On the phone he was brusk, stating that the marriage was short and over, and he thus had no knowledge of her whereabouts. But he offered a clue.
‘That’s long over. Ended in Ciudad Juarez years ago.’
“Ah, a Mexican divorce. At the time fast, simple, cheap... and later disregarded under the United States law. And so I checked. Yes, Mrs. Lipton, under her maiden name, was divorced under Mexican law in Ciudad Juarez, the presiding justice part time, his main trade cutting hair, the decree signed in a barber shop!”
I sit back in astonishment. With no legal divorce, Mrs. Lipton’s subsequent marriage to Jack’s father becomes quite murky.
“You see the implications? Mrs. Lipton is not the prime beneficiary... the will specifies it’s the wife of Mr. Lipton. Did he know of the Mexican divorce? Did he cleverly counter her insistence on cutting out Jack?”
Wow!
“Can the will still be contested?” I hastily query.
“I’m not a lawyer,” Lips Louie informs with self ridicule. “It would be illegal for me to give advice. For that, they could put me in jail. But I do believe that in probating a will, all sorts of representations are made to the surrogate. One of which being that a beneficiary is indeed the person so named in the l
ast will and testament.”
With that the limousine pulls back to my apartment building.
“It’s Saturday night, Miss Kelly. I’m headed to Soho. Perhaps Jack could once again entertain us there. The boys were quite impressed...”
As I step from the car, I ask myself, was Mrs. Lipton legally the wife of Mr. Lipton?
And in cutting out Jack, the denial appears emotional, not well thought out, the will obviously drawn under the influence of Mrs. Lipton. And Mr. Lipton conveniently let the emotions rule.
I lead Jack through the lobby to the elevators. I am excited. I need his tongue.
Chapter Forty-One
Sunday I put Jack on the treadmill, working him many miles. I need to think.
With the estate in the low nine digits, as Lips Louie suggested, that’s at least one hundred million dollars. That’s a lot of money and offers incentive for a lot of shenanigans.
Was Mrs. Lipton aware of the questionable nature of her Mexican divorce? Is that why she insisted Jack be completely cut out of the will, to be neither an alternative nor a minor heir to a vast fortune?
She did not like Jack, never enjoyed his company, essentially giving me carte blanche over his upbringing... and his body for that matter. No questions asked, not a second opinion requested when I recommended circumcision. And my bed wetting ruse, again upon disclosure, nothing but disdain. Though false, her haughtiness did not permit her to address the issue and become involved as a mother. Even a step mother should react in concern.
Yes, forcing Mr. Lipton to completely cut Jack out of the will was probably an emotional issue.
In negotiating Jack’s meager trust, discussions continuing after Mrs. Lipton moved to Palm Beach, I have her contact information. I also make a note to obtain from Lips Louie the name of the con artist, who many years ago inveigled marriage, offering Las Vegas wedding vows for a cheap night with a show girl. So abhorrent, such typical male skullduggery.
I hear the treadmill beeping, indicating Jack has finished a brisk five mile run. I return to the exercise room and demand twenty miles on the stationary bicycle. He must be kept physically attractive. With his high testosterone levels he shapes wondrously.
The Party Boy Page 8
