Ah, promotion... the word spreads. It seems that in time I will have Jack exposed to half the women of the City.
Alice has cleverly designed Jack’s uniform to tease. By mid afternoon, she begins stripping away portions of cloth with every return trip to the kitchen. Within an hour, Jack is naked but for the silly cap, neck collar, and cock cage... though the tray somewhat impedes visual inspection.
Yes, he teases, and one woman, probably on her third Mimosa, finally blurts that if she’s going to host a CFNM party she’ll want assurance as to the delivered goods.
So I find it time for the ultimate entertainment. I sit and summon Jack. I unlock cock cage and Prince’s wand and free his male package. It’s been hours since the Cialis was forced into him. As usual there is no need for encouragement or touch. He stiffens admirably. Wrists remaining secured to the tray, I playfully slap his buttocks and send him to the kitchen where Alice will reload the tray and Jack will now serve completely naked and erect.
Many Mimosas served, the cadre of women break out in giggles and catcalls. Jack is sublime... sublimely conditioned... sublimely erect... sublimely blushing with his erection bobbing about with each ungainly step.
Ah, and deep within he is so happy.
Chapter Forty-Eight
The Wednesday of Mrs. Lipton’s matinee comes. In deciding Jack’s mode of dress, I rule out his white and pink togas. It’s the Waldorf, the decorum more stately than a seedy Soho club.
Still I want attraction, the humiliation of being exhibited in female clothing quite exciting, assuaging Jack’s sordid masochistic need.
So I lay out the pumpkin orange pullover, a lesser shade for his silk panties and matching sandals.
The weather remaining warm, we’ll walk. It’s many blocks but Jack’s conditioning is superb. And I could use a little exercise.
A text message comes through, Mrs. Lipton departing the theater and suggesting to meet in room 2717 at 7:00 p.m. So I dress Jack, debating whether to lead him about on his leash. I decide the walk will go quicker without, but stuff the white length in my bag.
It’s late afternoon. Third Avenue is not crowded so we can walk at our own pace, yet there are enough onlookers to make Jack blush. At 50th Street we cross over, entering the rear of the Waldorf on Lexington Avenue. Into the elevator I reach for the leash and snap it onto Jack’s collar.
“Must mother see me like this,” Jack’s tone so sullen.
“I’ll show you to whomever I want, Jack. You enjoy the catharsis. And she’s not your real mother.”
With that the elevator arrives on the 27th floor, the doors open and I lead Jack down the hall to room 2717.
My knock is quickly answered and once again I am to consort with the haughty Mrs. Lipton, wealthy heiress. I greet and on reflection, though now in her fifties, there is a certain handsomeness, probably great beauty in youth. Yes, she could well have been a Las Vegas show girl. And from what I surmise from her comportment, a gold digger as well, though on that score her record seems to be 50 - 50.
I step within, Jack following my leash hand. He gazes downward, the humiliation of facing his mother... step mother... effeminately attired and restrained as a pet beginning to overwhelm.
“Sit,” I say snapping my fingers and pointing to a chair, offering slack on the leash.
Jack obeys. And I am surprised when Mrs. Lipton expresses no shock, but instead smiles in amusement.
“Still his governess, I see,” said Mrs. Lipton gesturing to a chair next to Jack.
“He has certain needs,” my reply intentionally vague as I sit, leash remaining in hand.
With Alice’s clever design, the hem of Jack’s pullover skirt rises quite revealingly when he sits, the lighter orange of his silk panties prominently displayed.
“At least he’s thoroughly disciplined. No longer seeking to spy on girls and their undergarments... instead wearing them, ha, ha, ha,” Mrs. Lipton said while sitting in a chair opposite. “Let me begin by saying, Miss Kelly, that I am well aware of your Ciudad Juarez reference. Many years past. A mistake to be forgotten. The man turned out to be liar and a reprobate. I had to pay all the costs.”
“Which I understand are quite reasonable in Mexico... and the process quite questionable from a legal standpoint.”
Mrs. Lipton pauses in thought.
“You have certain skeletons as well, Miss Kelly. Maria remains in my employ. She made me aware of your supervision of young Jack’s exercise routine. Quite telling.”
“Assuaging a need, Mrs. Lipton. Maria’s presence aided in treating Jack’s proclivity. Your son... stepson... needs to be displayed... naked... humble... and before women. It is best for him, keeps him calm and obedient. There was no sex, as Maria will affirm. And there remains no sex. Jack is kept in chastity, that is best for him as well,” I said returning bluntness with bluntness.
Mrs. Lipton smiles wickedly. I know she’s playing me, but I have the ultimate upper hand.
“If he’d be more comfortable, then so be it,” Mrs. Lipton said while gesturing in suggestive manner. “Since he’s now aware of the illicit nature of his birth, I no longer have to play the role of mother, do I?”
I’m beginning to better understand the woman. Could it be she’s one of us?
“Jack, take off your dress and panties,” I command in rising to unclip his leash.
What a look of panic! His blushing pink complexion deepens. He moves not.
“Show your mother that you are well kept... and cared for,” my tone firming.
He rises. As designed, Jack can by stripped naked in seconds. To obviate any further reluctance, I reach, grasp the straps of his dress at the shoulders and with a quick snap of the wrists and pull of my hands, whip the flimsy orange garment over his head. His hands obediently go to his head as he knows to step out of his sandals.
How many times has this scene been repeated, cleaning toilets almost daily in the nude?
Lastly I pull down his frilly panties from which he also steps out.
Jack stands before his stepmother, hairless body gleaming, muscle structure belying his effeminate attire. He’s an Adonis... with steel covered pubes.
“Remain standing. Let your mother look at you,” I command in picking up the clothing then returning to my chair.
“Makes quite the impression. And that cock cage is impressive as well. Paid for with trust funds I assume,” said Mrs. Lipton while gazing intently, certainly not shy about male nakedness.
“As I said, he’s denied sex. It is for the best.”
“I concur. Certainly would not want any more heirs... legitimate or otherwise.”
Jack begins to squirm. I know his exhibition, the excitement of being displayed, brings tumescence. Yes his penis is fighting its constraint, the erectile chambers flooding. He hates it... but he loves it. Ah the quandary of the masochist. And I understand it so well.
“Let’s talk about the will, Mrs. Lipton. Enough of stepson Jack.”
“What of it? It’s been probated. And a reasonable settlement made with Jack... and you as trustee.”
“Probated with you representing yourself as the wife of Mr. Lipton. Which you could not be if married to another. The Mexican divorce is a ruse, Mrs. Lipton. You’ve long known that.”
“You have nothing to gain in disclosing this. Jack is out. Only charity will benefit.”
“And I suspect be very aggressive in contesting the probate. All well funded charitable organizations with lots of lawyers... greedy lawyers. I have nothing to gain but you have much to lose.”
Mrs. Lipton returns to silence. I may be mistaken but there is joy in viewing Jack’s nakedness, seeming to ameliorate what I am sure is a most stressful conversation.
“More extortion. Just as I suspected.”
“You negotiated a little too hard with Jack’s penurious trust. You’re quite well off. Jack is not. And as you can now well imagine, he needs lots of care and attention due to his... proclivity.”
“I believ
e he’s in pain. Hate to think that I’m causing him discomfort,” the termagant twirling a finger in offering the same gesture... though there is nothing more to be removed... except...
“He’ll harden,” I forewarn, interpreting the motion of her finger.
“So be it. Make the poor boy comfortable.”
Jack’s key resides about my neck as always. But I must look to my bag. Returning the Prince’s Wand requires KY jelly, otherwise the reinsertion isn’t painful, it’s torture. Yes, I have small tube!
“Come here, Jack,” his stunned look silently pleading with me.
No mercy.
“Any arrangement we agree to will involve me taking over Jack’s care, Miss Kelly. That must be understood from the start. I will not be had a third time.”
“It’s burdensome, Mrs. Lipton. Keeping a male in chastity will require much of your time and attention.”
“I have a special place in mind for Jack. It will not be my time... it will involve my money... and that I have lots of.”
Her words come as I slip out the Prince’s Wand and Jack’s penis celebrates its freedom, instantly hardening. Yes, a tummy thumper. I do not believe I have ever seen Jack so stiff!
And I have not before seen Mrs. Lipton smile so radiantly. Yes, she’s one of us.
“I like the collar. Can you walk him about for me? Naked, erect and leashed... such an alluring presentation.”
Chapter Forty-Nine
Yes, it’s the Waldorf! And indeed I walk Jack about the capacious suite... naked, erect and leashed. Had years ago I known of Mrs. Lipton’s penchant, it would have been so easy!
“Enough,” a smiling Mrs. Lipton declares, eyes glued in watching Jack’s subordinated penis bob about. “I think we’re in agreement. Let’s talk terms.”
Well entertained by Jack’s ten inches and my directing hand, she nods to a bar in the corner of the Park Avenue enclave.
“You’ll find a fine bottle of Chardonnay, should you care to pour. If not to your liking, pick your own poison.”
Yes, spoken as a Las Vegas show girl, I conclude.
I hand Mrs. Lipton the leash and move behind the bar as encouraged. There is a bottle in the refrigerator. I open and decide to join her, noting she’s rather brisk in handling Jack’s leash.
“With Jack’s father so often absent, I would have disciplined Jack myself. But there were the many indiscreet eyes of the serving help to consider. Plus as stepmother, one’s role is limited, Miss Kelly. And it is a role of vainglory... setting high the household decorum. A Lipton boy cannot be known for hiding in closets and spying on partially dressed servants! Oh no, that conduct is never to be divulged. And since no one was to know, I could not step into the role of disciplinarian, announcing for all that this snot nosed brat had transgressed... punishing accordingly. No I had to hire you... wash my hands of the matter. And in a way I was glad to do so.”
Mrs. Lipton moves to an ornate bar stool tugging on Jack’s leash as I open the wine bottle. She sits and pulls downward, directing her tumescent stepson to kneel at her feet. I smile in seeing my leashed trained pet instantly obey. Mrs. Lipton then slips off her shoe and lowers her bare foot, pressing her toes against the top of Jack’s penis. The foot slowly bends Jack’s tummy thumper. He groans but otherwise knows to obediently remain motionless and accept a woman’s playful yet aggravating direction.
“He’s drooling. No sex you say. It must get very messy.”
“If he has not performed for a while I milk him.”
“Perform?”
Convinced that the harridan Judith Lipton is one of us, I quickly relate Jack’s weekend CFNM activities, explaining that in my mind being masturbated before amused women does not constitute having sex. She is both fascinated and disgusted.
“And he enjoys that? He is indeed a pervert... perverted as an adolescent... perverted as an adult. And what do you mean ‘milk him’?”
I push forth a glass of Chardonnay. I want her relaxed as I explain the clinical process by which I relieve Jack of his burgeoning hormones, removing his cock cage, lubricating his anus and massaging his prostate... forcing his male essence to meekly flow to a waiting towel.
“It has an interesting effect, calming him without the satiation of ejaculation.”
Mrs. Lipton smiles with the thought and slips away her foot. Jack’s penis instantly snaps up, resuming its stand at attention, bulbous tip abrading his navel.
“I will need to confer with my attorneys, Miss Kelly. I will want an iron clad agreement with you... and I’ll want Jack. You want money... and shall have it. I assure you it will be enough for a lifetime... and enough to find yourself another pet.”
As we clink glasses and imbibe, I look down to see Jack’s blushing nakedness turning from pink to crimson. And his penis indeed drools.
Jack’s masochistic need for exhibition is well assuaged. He’s excited... and he enjoys the ultimate in humiliation. Not only is he naked, erect and leashed... he’s just been purchased.
Chapter Fifty
Within two weeks I have a communication from the attorneys of Mrs. Judith Lipton. Lots of complicated documents... making the deal iron clad as indicated. But in summary, Mrs. Lipton will have Jack, and I will have in return for my pledge not to divulge the flawed marriage of the wealthy heiress $5,000,000... in installments, the last coming with the passing of the statute of limitations in contesting the will.
Jack deserves more... but Jack has needs other than money. And besides, if I take steps to inform the surrogate of the questionable marriage, it would not bring Jack much closer to an inheritance. Such action would merely alert the legal hounds of the half dozen charities listed as secondary beneficiaries. Nothing for Mrs. Lipton, but nothing as well for Jack.
So overall, it is for the best.
But what will Mrs. Lipton do to, for and with Jack? She took no interest in his upbringing.
Having shuffled through most of the legal stuff, I find a hand written note at the bottom of the pile. It is from Mrs. Lipton.
‘Should you need peace of mind, give Jack’s new home a look. Entry code Lipton 587345 Click the flag for the English version.’
Listed is a web address. And the many letters and numbers suggest it is not intended to be a domain for public viewing.
So I mark the closing date on my calendar... when I am to deliver Jack and his key, sign documents and have the initial installment of $5,000,000 wired into my bank account... then move to the computer.
Typing in the long address is cumbersome, it’s almost a code, and obviously designed such that few will haphazardly come across whatever is there.
I press enter. Onto my screen comes a very plain almost colorless page. There is a code required for entry. I type ‘Lipton 587345' then click the British flag, selecting it amongst a dozen others... French, German, Italian, Spanish and some unfamiliar to me, apparently European.
A welcoming page fills the screen, again very plain. No glitz. Obviously not a retail site attempting to sell something. There is a picture of an imposing building of concrete, appearing to be a military bunker. The caption below is not in English... perhaps German. It reads ‘Institut Für Sexally Abweichenden’.
I hear muffled sound and reach to turn up my speakers. It is a woman’s voice accented.
“You have entered the introductory site of the ‘Institute for the Sexually Deviant’. If you are not the person intended to have viewing privileges you are to turn off this page immediately. This is for private viewing.”
Alas the code with Mrs. Lipton’s name. She’s been given the so termed viewing privilege.
“A visual tour of the facility is available by clicking below. The pictures and scenes will be graphic and tend to disturb. Please be forewarned, we work exclusively with male patients, those needing to be excluded from society. The language used by the staff is a rare German dialect and probably not to be understood.”
The narration ceases. I click. There begins a video. The camera moves
forward towards the concrete building. A heavy door swings open, appearing to be of solid steel or iron. Visually we enter. As drab as is the exterior, the interior is likewise of concrete walls. The camera scans a reception area. There sits a nurse... young, blonde, of Teutonic heritage no doubt. The nurse ignores the presence of whoever works the camera, diligently shuffling paperwork at a desk laden with phones, computer screens and other electronics.
We move onward down a hall. There are doors. As a nurse exits one of the cameraman slips in before it shuts. Brightly lit, walls bare, there lays on a plain mattress a male. And the scene indeed tends to shock. Mid thirties, trim, naked and hairless... cranial hair included. And also extremely well bound. I recognize the many straps and connections as that of the Segufix system for binding very dangerous patients.... dangerous to themselves... or dangerous to others.
The woman’s voice returns to briefly narrate.
“When not being bathed and exercised, patients at the Institute are kept well bound for their safety and the safety of others. Hair is considered a problem of hygiene, possibly transmitting disease and lice. All patients are thus depilated during indoctrination.”
Yes, the sheen from the man’s head suggests there’s not a stubble to be found. I know from shaving so many, the follicles have been decimated.
As the camera pans the room, the man becomes agitated, futilely tugging and squirming against his many bonds. Then I note, in his nakedness, he begins to become erect. The cameraman also notes. The panning motion stops, focuses on the man’s penis then zooms in such that the viewers can watch the patient slowly come to full stiffness.
“As the viewer will note, our patients are easily disturbed. The presence of the camera woman has brought this unwanted reaction. The patient will thus undergo elektronisch abgelassen.”
Whatever the translation of ‘elektronisch abgelassen’ is, with the ominous tone of the woman’s narration it cannot bode well for the transgressing patient.
The cameraman... now known to be a camerawoman... departs, leaving the man erect and struggling. We return to the hall. Nurses stroll by, ignoring the filming process. Next another door opens. We are to tour a large wash room, a vast open shower area, water dripping from the walls. The camera lens steams. A hand comes into view to clean. It is a feminine hand.
The Party Boy Page 10