“Ok, finish for me.”
He does and with a tissue I dab the tip of the Prince’s Wand for neatness.
“Bacon and eggs for me. Dry toast for you. I want you well worked this morning.”
Our second bedroom is stuffed with as much equipment as we could move from the mansion years ago. Thus Jack’s impressive conditioning and physique remains. Missing is young Maria bringing welcomed embarrassment in toweling Jack down post work out.
Jack prances to the kitchen. In the bedroom I lay out clothing for his afternoon appointments. There were many elements to be considered in fabricating his special garb.
First such had to draw attention... in an undesired manner... nurturing Jack’s penchant. Second such had to be practical, nothing so extreme that he could not walk or otherwise move about. Third such had to place Jack in compliance with the law. Much as I’d like him to be exposed, arrests would prove to be counter productive. And fourth, such had to be easily removed. Jack’s customer’s want him to serve in the nude. Covering can annoy, along with the precious moments wasted in taking such off.
So, starting with the footwear... high heels would be ideal but not practical for walking New York’s streets. I settled for a selection of sandals, leaving the top of his feet exposed and having a degree of height in the heel... just enough to make walking challenging yet doable.
He’ll wear silk panties; of course... always wear silk panties. But more covering for the laws concerning exposure. For that I had made a set of flimsy one piece dresses, to be facilely slipped over his head, open at the shoulders but for thin straps for support, covering his chest at the front, a plunging neck line at the back, the hem there just above the crease of his buttocks, and the bottom hem quite high, ending above mid thigh, flashing his panties beneath when walking or better with gusts of wind on inclement days.
A male in what most would consider female attire. A muscular male, otherwise no hint of femininity. Ah, the gender obfuscation... delicious.
There are no pockets. Jack carries no money, no cell phone, no identification. He tends to rapidly negotiate the sidewalks of New York, trying his best to avoid the stares of onlookers. This assures that he will not dally and will move directly to his appointments, my supervision temporarily superfluous.
Pink, red, blue, a pumpkin orange... today I select yellow. Sandals the color of bananas, panties in a pastel yellow, slipover dress a deeper yellow. This will best draw the eyes’ attention when his undergarment flashes with every step.
“Breakfast, Miss Kelly,” Jack calls.
I finish laying out the simple but humiliating attire and join Jack in the kitchen.
“Set the treadmill for ten miles this morning, Jack. A nice long work out then bath... make you nice and clean for Mrs. McConnell.”
“You’ll milk me?”
“Of course not. We have a show in New Jersey this coming Saturday. I want you well primed. The Cialis assures you’ll be hard, not that you’ll spurt for the girls. I want that ball sac nice and full.”
My words disappoint, I know. So many years of daily prostate massages during his developing years. Yes, he’s addicted to my care, but he’s also obedient and docile as a result.
“I’m not sure what to expect. It’s not a bridal shower like last night. So I need you ready for all possibilities. They may even want you to come for them... fully ejaculate... imagine that!”
That brings a sheepish smile. I must keep Jack’s spirits up... to a certain extent. And I truly do not know what to expect. But I withhold the fact that I know our hostess to be a devout lesbian. Why she’d desire a CFNM performance I have no idea. But my Craig’s Listing is deliberately open, basically suggesting that I have an obedient, young, well hung male ready and willing to expose himself... specific activities to be discussed.
Jack finishes his dry toast and clears the table. As he departs the kitchen I smack his buttocks, rounded with exercise, hairless by way of my razor.
“I want you in a good sweat,” my tone pleasant, but Jack knowing he will indeed be worked into a good sweat.
I move to the computer. My Craig’s listing needs to be updated. In thought, perhaps I should expand our prospective audience. So for the first time under the ‘Personals’ banner, I click ‘men seeking men’ and compose an ad.
I am so wicked, typing away, imaginatively posing as Jack.
‘Sublime nakedness’ I type as an enticing lead.
Then I compose, listening to the whirr of the treadmill as I blaze a new trail for Jack’s penchant of masochism...
I am a 25 year old, Caucasian male, well conditioned, virile, well hung, well controlled by an understanding woman. She demands that I pose professionally, limits few, clothing undesirable. Fee negotiable.
So we expand, in addition to CFNM gatherings, I’m offering Jack for CMNM as well... clothed male, naked male. To my knowledge he has not before exposed himself to a man. It’s time to broaden his penchant.
I click the appropriate boxes to post, then step to the apartment door for the Sunday paper. I read in relaxation as Jack tones his nakedness. When his ten miles are finished, I will supervise some work on the Universal gym, then end with the stationary bike, watching his cute buttocks roll about.
Thereafter, perhaps I’ll dust off my nurse’s uniform for some bath time nostalgia...
Chapter Twenty-Four
Well watered, bathed, testosterone injected, Jack dresses, always with that wounded puppy look when contemplating walking the streets of Manhattan in female clothing. Since I don’t otherwise feminize, his appearance is quite conflicting for the typical passerby. A flimsy pullover dress, panties flashing beneath, the heeled sandals of a young girl, yet male styled hair, no jewelry, no make up.
Having shaved him during his bath, his arms and legs are uncharacteristically hairless for a male, bringing even more confusion in assessing his gender.
I must respond to his pouting.
“Jack, would you prefer your blanket instead? No dress, no panties... you’d need to grip it well,” I chide.
“I’d rather dress as a man,” the words defiant but his tone humble.
“I will not allow that, Jack. That would imbue male pride. You feel better being humiliated, soaking up the deriding looks you’ll receive. And besides, Mrs. McConnell and Mrs. Iorio will want you completely naked. You just need to step out of your sandals and panties and toss to the side your dress... and voila, a very presentable nude servant.
“One more glass of water before you leave.”
“But I’m full.”
“Drink another glass,” my tone stern.
Mrs. McConnell knows Jack must request feminine assistance in using the toilet. Thus I fill his bladder so he’ll be in great need upon arrival at her apartment. Just as I directed his steel encased penis this morning, Mrs. McConnell will likewise amuse herself.
A final glass of water imbibed, I smack Jack’s posterior, now covered in sheer yellow and point to the door. My glum ward steps awkwardly, the sandals always requiring acclimation.
Bizarrely dressed as I demand, I’ve procured many customers for his services right in our own building. Neighboring women, initially coy in encountering a man so oddly attired, quickly adapt to Jack’s subjugation when I explain his penchant and his craving for subservience to women.
“If you need your toilets cleaned, perhaps you can be of help to Jack,” I politely suggest, quite the possibility that many have penchants complementing Jack’s needs.
And it has proven to be true. Six neighboring apartments, six bathrooms made spotless each week. And there is advantage. Jack can dash through the apartment building sans the dress and sandals. Theresa on duty at the security desk, smiles in seeing him on video camera prancing with celerity through the halls in ostensible concern. Yet his masochism... his exhibitionism... bring partial tumescence to a well secured penis.
Relieved for a couple of hours of my Governess chores, I put on a sports bra and shorts. It’s time
for my own work out and bath.
Chapter Twenty-Five
The week goes quickly. By Friday Jack has earned $55... eleven women visited, eleven toilets cleansed.
He always returns flustered, complaining about the degradation and the low pay. I politely listen then inform him of the next day’s appointments.
I communicate with the woman requesting a CFNM party in New Jersey tomorrow, getting directions, outlining the protocol for Jack, assuring the base fee of $300 will be advanced before I take away his blanket and unlock his cock cage.
It comes to light that there will be female nudity at the home of this Lesbian woman. I explain that one of the regimens of Jack’s subservience is that he has never gazed at a naked woman and that I forbid it, the satiation of that segment of male curiosity, the eidetic male mind, never to come. I thus write that Jack will be kept hooded if there is such nudity.
The woman writes back quite bluntly... ‘I just want a stiff cock’.
A curious reply for a daughter of Sappho. And since a chaste, randy, testosterone suffused, Cialis charged Jack will be arriving Saturday night, that expectation will be easily fulfilled.
The replies to my trial Craig’s Listing, what I mentally reference as the CMNM experiment, are rife. As with everything on the internet, many insincere responses, some from outright crackpots who seem to have much time and use it to waste the time of others, and a couple worthy of follow up.
Envisioning Jack titillating men who find the male form attractive in a way titillates me. And though my experience with the gay scene is limited, I know most within flagrantly flaunt their sexuality. I doubt if Jack will be comfortable exposing himself to gay men. But it’s when Jack is uncomfortable that his penis hardens most... that is ingrained in his masochistic psyche. And it is something I enjoy feeding and nurturing.
I thus begin corresponding with one man who writes clearly and plainly sets out his desires and what is expected of Jack. And I in turn write clearly and plainly that I am the woman who controls Jack. And then begin setting the rules... that Jack is not to have sexual relations... that his nakedness is only for entertainment... touching of course permitted. And of course, outlining the augmentations... masturbation... ruined orgasm... controlled ejaculation... but only by my governing hand.
My set rules agreed to, I forward a picture of Jack obediently displaying his body, perched on a small stool, head hooded, and his cock caged. The response is enthusiastic, the return email demanding a proviso... if Jack fails to stand... if Jack does not attain a stiff ten inches... the fee is to be returned.
Done deal! Jack is to be presented at a Soho club the following Saturday.
Finished arranging Jack’s schedule, I give thought to his presentation. Perhaps the blanket as covering and the removal thereof for show is too unimaginative. And leading about by the hand, in my mind mother guiding a child, is not domineering enough... to be possibly misinterpreted as the entwining of lovers rather than the feminine governance of a deviant exhibitionist.
“Jack,” I call out. “When you’re finished with the vacuuming, put on some panties and grab your blanket. We need to shop for clothes.”
Well I certainly got his attention. Jack, of course, envisions men’s clothes. I will soon have him disavowed of that notion.
Chapter Twenty-Six
So much aware of Jack’s inner need, his craving for feminine control, forced exhibition, I once again slip away his blanket and toss it the back seat.
“Take off your panties for me. It’s a nice day for you to ride naked.”
My command comes as we traverse the Queensborough Bridge. It’s a warm day so I open the windows, the rush of air over Jack’s hairless skin highlighting his nudity. He must show displeasure, but I know it to be a subterfuge, secretly enjoying being completely bare with a woman in control.
Drivers of automobiles assume that Jack is merely shirtless. But when I pass a truck I slow the speed and honk, bringing the attention of the driver. Looking down he can quickly ascertain Jack’s state of complete dishabille, the gleaming steel cock cage evidencing Jack’s subjugation and ownership.
Such fun!
In Astoria, I turn into a narrow alley way knowing there is parking in the rear... secluded parking. With a little used back door entrance, Jack need not dress. Still I must coax him from the car.
“Come, Jack, Miss Alice is expecting you,” clapping my hands as one would seek to gain the attention of an aloof puppy.
Jack knows of Miss Alice. She has made his special dresses, a skilled seamstress with an open mind, amused by a brawny yet well governed male.
We enter the building. It is a work shop filled with machinery, rolls of cloth stacked high on racks.
“Kelly, nice to see you,” Alice pleasantly greets.
She steps forth to also greet Jack. Alice is a woman of authority. In her profession of dress making she rarely deals with males... and she does not miss the interaction. A hand reaches forth and tweaks Jack’s left nipple, symbolically setting the hierarchy. Jack is considered a naked beast, something upon which she will not waste her words. Accordingly, Jack knows to remain silent in Miss Alice’s presence.
Alice’s ostensibly vanilla occupation of clothier is abetted by the fabrication of costumes and fetish wear for dominant women. She is not bashful. Instead quite libertine and never offers judgment.
“So you bring your boy in naked. My dresses wear out?”
“No they’re fine. It’s such a nice day and you know the thrill Jack gets in showing himself off.”
Alice smiles.
“Yes I’ll wager he’s feeling the tightness of his cock cage right now, that well kept penis wanting to show itself as well,” Alice’s hand lowering to playfully pat Jack’s low hanging testicles.
The lugubrious look on Jack’s face is precious. He knows Alice is correct.
“I need something for Jack to wear, easily removed, of course, but offering flare. When I party him, the blanket I allow him for covering is... well rather uninspired.”
Alice steps back, arms akimbo in thought.
“Well first, I’d leash him. Leading a boy about by a collar always sets the tone, quickly communicating a woman’s governance. And I can make a collar for you, decorative... or high, thick and functional.”
“Yes that’s a thought. Make it high and thick. It’s best for him to feel a woman’s ownership.”
“And if you’d like I can add some ringlets for a locking hood.”
“Excellent. Jack, to your knees so Miss Alice can measure.”
Jack obeys, and Alice removes the ever present tape draped about her neck and shoulders.
“Locking buckles? Or do you want it permanently sewn in place?”
“Hmm. Can’t think of any reason why I’d need to remove it.”
“Good, I’ll use a strong gauge of wire. Difficult to sew, but I only have to do it once,” Alice circling Jack’s neck for measurement.
“And how about a simple toga?” Alice muses. “I’ll design it to cover the arms, chest and back. You tell me how much of him you otherwise want exposed. Maybe have his cock cage peek a bit, letting people know he’s in strict chastity. I can have it attached using Velcro. Stripping him naked would involve a snap of your hand.”
I like that idea. Some drama. I lead Jack by a leash then with a quick tug expose him. Alice has a good notion for flare. I concur.
“Color?” she inquires.
“Can you make two?”
“Yes.”
“Okay, one white and one pink. I’m putting him on display in a gay club, one week from tomorrow.”
“Easily done. Bring him in any time after Wednesday,” Alice affectionately patting Jack’s head, master to dog. “He’ll be quite embarrassed stripped naked in front of men.”
“Yes. And he’s eager. Deep within the humiliation excites. He just doesn’t understand it.”
Chapter Twenty-Seven
No work out for Jack on Saturday. He’ll need
his energy for a lasting erection.
He cleans house. I make him nap. At 5:00 p.m. I run water for his bath. At great cost, both plumbing and plumbers expensive in Manhattan, as with everything, I had an over sized tub installed.
I bathe Jack just as I have over the many years, posed on all fours as in cleansing a puppy, my soothing touch that of mother to child.
He’s docile, of course, absorbing my tenderness, hands smoothing every where, expressing ownership, exercising my thorough control.
I particularly enjoy handling those ripe plums, hanging so low after my many scrotal infusions during his developing years. Soft, thin, hairless flesh... so vulnerable to a woman’s touch. Jack lurches when I gently pinch his right testicle then left.
“You’re full of juice this evening, Jack, a week of built up sperm. I can feel it. Maybe the girls at the party will have me masturbate you. They’re lesbians but they may find it entertaining to see a woman with ultimate control over the male sex organs.”
“I’d like that, Miss Kelly. Full ejaculation?”
“Maybe.”
I entice, yet my intuition tells me it will not happen.
Finished washing, I coat his nakedness from neck to thighs with lotion then run a straight razor over every inch of skin. When completed Jack knows to turn and sit, like a good boy, and I lather his chest and arms. Hair stubble, quite limited as I shave him regularly, disappears, maintaining his smooth girlish look. Legs are next, wordlessly lifting the right from the water. I am quick, gliding the frighteningly sharp steel edge with aplomb. Left leg follows. In completing the final appendage I next shave his scrotum, handling with gleeful authority.
“Are you going to get nice and hard for me?”
Jack smiles, a little boy smile, as I pull from my neck the necklace with the most meaningful trinket of his male life... the cock cage key.
Though I dislike freeing his penis, in my mind unearned mercy, in preparation for his exhibition I must assure the steel is cleaned, and any stubble beneath is likewise shaved. The lock for his Prince’s Wand clicks open as does the lock for the base ring. I slide off the cock cage, marveling at well designed tightness. The slightest degree of tumescence sends a message of feminine control.
The Party Boy Page 5