The Party Boy

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.’