The Party Boy

“Oh, well. You may consider reviewing that. Though Jack is illegitimate, as I am sure you realize, Mrs. Lipton’s position is somewhat precarious... was somewhat precarious as well.”

Lips Louie’s club appellation is well earned, his lips indeed moving... and doing so to intrigue.

“Illegitimate?”

“Mr. Lipton never married Jack’s biological mother. He did not have a first wife, the woman was a trollop. Mrs. Lipton was obviously aware of the transgression and used it as a lever over her husband up to the day he died... insisting that Jack be out of the will.”

Ah, that further explains her aloofness concerning Jack and his care.

“Why are you telling me this?”

“I like the way your boy is cut. So cleanly... and he’s of nice size. He’ll find me to be very caring...”

Ah, Lips Louie seems to be a serial fellator.

“Well now that I know, why should I offer...?”

“You’re not curious as to Mrs. Lipton’s precarious position?”

Yes, mentally I skipped over that, my thoughts focusing on Jack’s legitimacy.

“What about it?” I blurt with impatience.

Lips Louis smiles coyly.

“I’ll make it long and pleasurable for him. I’m very good. And I think you will greatly benefit from what I have to say... afterwards”

I step back, arms akimbo in more thought. Jack has no CFNM party next weekend; I’ve spent so much time preparing for this Soho soiree. If the information is as relevant as Lips Louie suggests, it may be worth having Jack’s scrotum drained for the cause.

“Next Saturday. Hire a limousine. I have a service you can call. You will accommodate Jack orally as you tour the city. Afterwards we’ll talk.”

Lips Louie nods in excitement.

“Are you going to have him ejaculate for us?”

“To bring him to fully spurt is another $300,” I firmly declare in my stentorian businesswoman’s voice

Chapter Thirty-Seven

Poor Jack. Either the patrons of the Soho club are a cheap bunch, or they were so preoccupied with getting their own rocks off that they cared not to watch me masturbate Jack.

No $300 offered for jerking him off!

An alternative supposition... none had an interest in me as female doing anything. For other then interacting with Pattie concerning initial payment and conferring with Lips Louie, no one talked to me. I even had to shout at the bartender for a drink, my presence tolerated due to Jack’s fine priapic exhibition.

So it’s Sunday and Jack is entering his third week of chastity... moaning and pleading for climactic release.

Well, I promised him a milking. And he will get it.

From deep in my closet, I dust off my masturbation harness, used many times with Jack’s predecessors when, as a young governess, I found that masturbating some obstreperous boy quickly brought calm and altered comportment.

Waist belt with cuffs attached, thigh straps and neck collar. It humbles and positions a boy for long, slow, controlling strokes of a young penis.

Due to Alice’s fine handiwork, I can dispense with the neck collar, Jack’s more or less permanently in place.

Since it’s to be a milking, not outright masturbation, I can withhold any hand work. But I will need a vibrating anal insertion and a simple wooden dowel.

I clear off the kitchen table, thinking that Jack should be more wary of that for which he pleads.