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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?
