Chapter Forty-Two
I find an email address for Ms. Judith Lipton, wealthy widow of Jack’s father. I send a brief note providing my cell phone number and suggesting that we need to talk. Since our relationship became rather testy when I had Jack’s attorney initially question his father’s will, I decide that it may be best to spice up my otherwise polite note. So I add a postscript, questioning if she, Ms. Lipton, has been to Ciudad Juarez recently. That should gain her attention!
In hitting send I notice that in my inbox I have a reply from my recent Craig’s List posting offering Jack’s nakedness for CFNM parties.
How cute! A woman, rather bold and liberated, inquires whether Jack will perform at an 18th birthday party. Seems she wants her daughter to be more familiar with the male anatomy, ingrain more assertiveness when interacting with boys.
I respond affirmatively, with the proviso that all in attendance be of age. A follow up email confirms that the attendees will be age 18 or older. We set a date for the forthcoming Saturday afternoon.
The communication gives rise to thought. Perhaps I should post a separate Craig’s Listing offering Jack as a boy who will jump out of a cake at ribald parties for women!
Yes, he’ll be locked up... and the honored guest will be presented with his key, the decision hers as to whether or not Jack will display himself erect. Clever stuff.
In scrolling through other emails, I find it tedious in deleting the number of crackpot replies. How is it people have so much time to be so insincere? In thought, perhaps there are alternatives to Craig’s List in terms of finding outlets for Jack’s need, his craving for exhibition.
Ah, why not have a little teaser? A Sunday afternoon tea party. I’ll not only invite all of Jack’s cleaning customers but suggest they bring friends, women of our ilk who either need their bathrooms clean or simply want to be entertained.
I begin composing a list beginning with Theresa, Mrs. Rivers, Iorio, and MacConnell. And Alice! With her clandestine kinky dress making she is sure to know women with exotic tastes in being entertained. In completing, the list is extensive with all the toilets Jack cleans.
The hum of the bicycle ends.
“Run some water, Jack. Bath time.”
Chapter Forty-Three
Jack kneels in soapy warmth. After the extensive exercise I have demanded he’s somewhat lethargic but grateful for my controlling touch, the ritual of many years of embarrassing cleansings becoming psychologically acceptable.
He has never washed himself as an adult. I’ve soaked and shaved him daily.
“So did you enjoy performing for Louis, Jack?”
He’s chagrined. When I feel his muscles stiffen I know his homophobia still somewhat seethes.
“I really didn’t do anything. My hands... my hands...”
“Yes, I had you secured... to make sure you were polite and receptive. But he sucked your penis, didn’t he?”
Jack knows that I insist on full answers no matter how bothersome the question.
“Yes, ma’am.”
“And you ejaculated?”
“Well... not right away. He sort of teased.”
“And how did that make you feel, submitting your penis to a man?”
“Icky,” Jack’s reply quite childish, his emotional development intentionally kept retarded.
“But at the end, he permitted you to climax... just like you want me to make you climax. So it felt good?”
“I guess so.”
Such emotional turmoil, held in strict chastity... only to finally be brought to ecstasy in such a degrading manner... for the homophobe.
I begin shaving, Jack’s penis remaining locked up. There’s really very little stubble, but I want his entire body to sense vulnerability, whisking the sharpness everywhere. I know beneath his cock cage there may be some growth, but that is only removed in preparation of show.
As the razor glides down his left buttock, so nicely shaped from years of stringent physical work outs, my cell phone rings. I pull the plug.
“Stay,” I command as the water drains.
Retrieving the phone I do not recognize the number, but it is a Florida area code. I answer. It’s Mrs. Judith Lipton.
“What is it? You’re annoying. Since I consider Jack’s trust fund nothing more than submitting to extortion I really don’t think there’s anything more I’d like to say.”
Oh, but there is, I think to myself. But as gruffly as the termagant speaks, there is no reason for me to be impolite. I am holding the cards.
“Are you going to be in the New York area in the near future? I think you’d like to see your stepson. He can be quite entertaining. And I would like to learn more of that quick trip to Mexico many years ago. Ciudad Juarez I believe it was,” I reiterate, thinking perhaps she did not scan my entire email.
There is a telling pause... silence!
“I’ll be flying into New York two weeks from Wednesday for a matinee show. Staying the night at the Waldorf,” her voice softening.
“Text me your room number and a good time. Jack and I will visit. You’ll enjoy seeing him,” so punny am I.
I hang up. Knowing that Mrs. Lipton is not biologically related to Jack, now being aware that with his illegitimacy she holds him in disdain, greatly changes the rules of the game in my mind. As haughty as the woman was... is... she may have enjoyed more closely assessing my early years of Jack’s governance.
Ah, Jack! He lingers in the tub, cold and wet. I return to the bathroom. Jack is not permitted to dry himself. That’s my task, again palpating every inch of his naked freshly shorn flesh. Afterwards I’ll hood him and put him to bed, his tongue and lips to be in wait for my pleasure.
Chapter Forty-Four
I wrap Jack into his white toga.
“A birthday party, Jack. I doubt if they’ll want you brought to orgasm. But you’ll still be displayed,” my words coming as I pop a Cialis tablet into his mouth and offer a third glass of water.
I’m not sure Jack’s urination trick will be of interest, but keeping his bladder full abets erection, and that’s key.
I leash him and it’s to the garage. Another trip to Greenwich Connecticut, the 18th birthday of a girl about to obtain a lesson in male anatomy... and male sexual deviance.
Traffic flows well midday Saturday. We arrive at a large suburban home within an hour. Guiding Jack by his leash always makes an impression, the many teenaged girls giggling, mothers amused as well.
Upon accepting an envelope of cash, I rip open the Velcro seam of Jack’s toga and pull down his frilly panties, the sight of which brings more giggles. Since the birthday girl’s mother has not only requested that I provide entertainment but information as well, I lecture. A sheepish Jack, blushing with his exposure remains silent, hands on head.
“Jack is a submissive male, girls. He does not fully understand, but he wants to be cared for... and kept... his needs quite idiosyncratic,” I begin my lecture as my leash hand guides Jack to the stool I politely suggest for every CFNM gathering.
“As you can see he blushes quite profoundly,” Jack knowing to mount for exhibition. “But deep within he very much enjoys the humiliation. That is why I have to keep his penis well controlled. This is called a chastity device...” pointing to the steel cage. “Very expensive, very well designed. It’s locked in place and prevents Jack from playing with himself... as I am sure you girls with brothers understand the male is wont to do. I have the key and only I decide when his penis is free.”
“How does he go to the bathroom?”
“Jack can urinate through this tube... called a Prince’s Wand. But only under my supervision. I control almost everything Jack does. It is best for him... and it is best for other males like him.”
I pause, letting some dozen female eyes take in the scene of intense male degradation. Jack fidgets, his penis hardening within the cruel cock cage. Oh that masochistic psyche!
“I think Jack wants to show off for you girls. Is that right, Ja
ck?”
He does... but he doesn’t. Such mental and emotional conflict. The embarrassment begins to overwhelm, his phallus fighting hard steel. Finally, he must answer, his voice quavering.
“Yes, Miss Kelly. I need... I need...”
“He needs to harden, that is what he’s trying to say. I only allow it on special occasions... like a girl’s birthday,” my words coming as I pull the necklace and key from about my neck.
I click open the two locks, my hands gently loosening the cage.
“You see, girls, in boys with Jack’s penchant; he very much enjoys the humiliation. And as with all boys who enjoy themselves, it shows in their penis.”
With that I remove the cage and base ring, Jack’s manhood already semi engorged. Next I work the Prince’s Wand, just able to have the bulbous tip exit the urethral opening before full erection. With that, to the sound of astonished gasps, Jack’s penis rises, his ten inches displayed in full bloom. There are more giggles, there are whispers expressing amazement.
“And the humiliation of being displayed naked and erect brings more and more hardness,” I said while placing my finger on the top of the stiffness and bending downward. “It’s termed the loop. And the subordinate male cannot avoid the loop. It’s ingrained. Note the look on Jack’s face.”
I slip away my finger, releasing the rock hard appendage, allowing it to snap back to full stand. And Jack’s look is indeed precious.
Next I cup his scrotum, drawing forth the mass of pink flesh to offer a full view of the hairless testicles and explain the function of that segment of the male anatomy.
A girl questions Jack’s hairlessness.
“I shave his entire body and bathe him daily. He needs to feel a woman’s controlling touch. Plus, don’t you think he’s well presented?”
There come murmurs of agreement. Then Jack begins to secrete prostatic fluid, which leads me to that segment of the male anatomy. The prostate gland, lecturing how to access it through the anus. I do not demonstrate, that’s an extra fee and deeming such a little advanced for the girls.
I also explain that Jack is circumcised, of which I am proud as stated, and that on some males the foreskin remains. And just to titillate, I offer that the tiny patch of flesh at the underside of the tip is where the male obtains some 80% of his sexual pleasure. This always baffles girls, feminine anatomy having several erogenous zones.
And so the afternoon entertainment goes, a very practical sex education class... and lessons on the demented mind of some males such as Jack.
Any budding women of authority in the group? I must wonder...
Chapter Forty-Five
Sunday, Jack is quite agitated over his birthday display. And no, he was not masturbated, the girl’s mother deeming that to be over the top.
“Finished with your cleaning?”
“Yes Miss Kelly,” Jack vacuuming completely naked as always.
“Good boy.”
I arise, the Sunday paper partially read. I gather up Jack’s masturbation harness. As promised, if he is not brought to orgasm at a Saturday CFNM gathering, then I milk him. Yet on this occasion I decide to tease a bit. Plus I need to have my own recreation from time to time.
“Come here, Jack.”
He approaches and I detect the conflicting emotions as he spies me holding the waist belt with attached wrist cuffs. He both hates being milked and pines for it. Hates being denied the ecstasy, yet knows a well massaged prostate and the resulting hormonal release will bring a state of languor, akin to the torpor of a deep nap.
I encircle his waist then cuff him, arms restrained at his sides. Next I unlock his cock cage and slip out the Prince’s Wand.
“Watch some television,” playfully smacking his buttocks.
“But... but...”
“Bring yourself to erection if you’d like,” noting that with his randiness he’s already firming. “Try not to drool on the carpet.”
And with that I return to the Sunday papers, leaving Jack to helplessly stroll about, erect with no manner of pleasing himself.
Such a cruel woman am I. When I do deem it to be milking time, he will be most eager.
Chapter Forty-Six
One must give to get, the basis for all promotion.
Having put together my list of guests, I send out invitations. What a gathering of understanding women I will assemble, all so willing to help Jack and his craving!
Yes to spread the word concerning Jack’s availability for toilet cleaning and male nudity, I decide on a Sunday afternoon tea party, though there will certainly be other refreshments. And Alice, having Jack’s measurements at the ready, has offered to whip out a cute maid’s costume. Though my guests will want him naked... and certainly displaying all ten inches... I’ll work my way into the CFNM thing as the party progresses.
Since Jack will be serving, he’ll need to use his hands. And whereas he’s trained not to touch himself, it’s easy for him to comply when I am always nearby while freed of the cock cage. The question is can he keep his hands off his erection when not supervised?
Yes, I’d prefer to mingle with my guests, not following him into the kitchen every time a new round of tea and biscuits is served.
So I must conjure. In my many years of governing belligerent boys, I have a variety of restraints, on occasion needing to put a boy in isolation for many days. Yes, a few days of sensory deprivation can quickly establish a woman’s authority. Just hearing an obstreperous teen beg for a diaper change can bring a satisfying exchange of power.
So I rummage about my closet and find all sorts of fun stuff, paddles, spreader bars, and heavy shackles. And then finally I come across my Posey cuffs. Resilient nylon, lined with foam for long term comfort, such are safe, used in institutions world wide, and ineluctable. Sewn heavily are eyelets which will accept tethers, restraining the bearer in any number of positions and places. Alas, could it be that a silver serving tray can be utilized to bind together the wrists?
Yes, between the arms my pet will carry a tray laden with refreshments, the handles clipped to Posey cuffs making the hands... and those naughty fingers, immobile.
And whereas for practicality he wears sandals while negotiating the sidewalks of New York, I do believe heels, high and pointy, will suffice in my apartment. Those I will need to purchase.
Chapter Forty-Seven
Jack makes for a delightfully clumsy maid. The morning of my tea party I have him practicing, wearing heels impossibly high, wrists donning Posey cuffs, silver tray attached, separating hands rendered useless for all but serving tea and biscuits. I teach him to curtsy and for some reason bringing him to politely smile is a chore.
“I don’t want to do this... to look like this, Miss Kelly,” he said with such childish pouting.
“Oh, Jack. You’ll do and look as I please... and enjoy it. Think... you’ll be wearing clothing... for a while. And during the afternoon I will free your penis so you can show off. You so much like that,” speaking as if to a boy showing reluctance in taking his first train ride. At afternoon’s end he’ll not want to get off.
Jack is naked, penis caged. Alice is expected with the maid’s uniform. She’s a whiz so I know it will fit... probably better phrased as being revealingly tight and brief.
“And you’ll need to smile and be polite. Lots of women will be here to see you display yourself.”
With that, the intercom buzzes. It is security announcing the arrival of Alice. I inform that she is expected along with a dozen or more other guests to be permitted entry. I unlatch the apartment door and within moments Alice arrives. She expects to see Jack naked and well groomed. And I can read her thoughts... in a way it will be disappointing to have him dress.
“I have just the uniform for him,” Alice pridefully announces.
I release Jack from the bondage of his serving tray, unclipping the silver from Posey cuffs. Alice then goes to work and I note every piece of black satin is garnished with frilly white lace. A bodice nicely outline
s Jack’s pectoral muscles. An extremely short pleated skirt covers only the upper portion of his buttocks at the back. At the front his cock cage peeks, the gleaming steel leaving no doubt he’s a kept boy. Alice props a silly hat atop Jack’s head. Then come stockings, Jack having to temporarily remove the extreme high heels while Alice rolls on patterned sheer black nylon.
When finished, Jack looks absolutely ridiculous, such masculine brawn attired so effeminately.
I return the tray, again clipping the Posey cuffs to render Jack’s hands useless for all but offering refreshments.
I then draw Jack to the kitchen. One more glass of water to encourage a nice piss proud erection... and with it his Cialis tablet.
No sooner is Jack watered then one by one my guests enter. My maid greets with beverages, awkwardly curtsying while balanced on the outlandish heels I purchased. For the women who know Jack, having him weekly clean their bathrooms in the nude, they are surprised and somewhat disappointed with the covering, however brief. Mrs. Iorio appears tempted to strip off Jack’s uniform, reaching beneath to pinch his buttocks. As the group assembles I feel it necessary to explain that full nakedness will come.
This seems to calm the group, expectations apparently high.
So we mix, we talk, the women who know Jack exchange thoughts on how best to bring the humiliation he craves. Most importantly there are invitees who are introduced for the first time to the delights of CFNM. And word spreads that for $5, Jack will make a bathroom sparkle... and do so in full display.
And of course, I lecture on the entertainment Jack can provide on weekends, stripping, tumefying, being stroked under strict supervision... permitted ejaculatory release... or allowed to meekly dribble as a result of my specialty... the ruined orgasm.
The Party Boy Page 9
