The Party Boy

It was during one of these lengthy afternoon intervals that I learned something key about Jack.

It’s one thing for a boy to harden while I am penetrating his rectum, taking control of his penis and slowly milking him of the essence that brings rebelliousness and lusty thoughts. But it is another for an erection to spontaneously spring forth while enduring a grueling workout... and such occurred.

Nearing the end of a long afternoon, I noted that there was a shortage of towels. With Jack sweating profusely, this can be quite the inconvenience. I thus phoned down to the maid’s quarters, demanding immediate attention in the form of fresh towels.

With my household rank just below that of Jack’s mater and pater, the response was quick, perhaps too quick. A pretty young serving girl, apparently having neglected to replenish the supply, stormed up to the attic, entering without announcement in hastily rectifying her oversight.

Jack, having just completed many miles on the treadmill, drenched in sweat, was aghast with the girl’s presence. She apologized, in no way suggesting that I as governess was engaging in something sultry or lewd, and in setting down the towels attempted to depart with equal haste. But in seeing Jack’s reaction, so accustomed to being in the nude solely with me, finding the presence of another fully clothed female to be stultifying, I could not resist being mischievous.

“Maria, stay and help,” my voice firm, my authority respected. “Jack needs to be toweled.”

My words did not bring apoplexy, but Jack, appalled with the notion of exposing himself to a mere maid only one or two years his senior, was most daunted by the notion of the pretty young thing touching his wet flesh.

“I can do it myself,” his protest meek... tellingly weak.

“No, Jack, you are to be cared for by Maria,” my words by now known to be a command.

And so it was... a well worn Jack... completing quite the exhausting work out, was made to stand, hands on head by rote, as the lowest ranking maid of the household took charge of his nakedness. And yes, despite the depletion of much energy, he slowly tumefied, his embarrassment palpable, yet leading to telling arousal.

“I did not mean to do this,” an upset Maria stepping back, both shocked yet intrigued as the well hung Jack displayed his stiffness, the organ which I daily milked.

“It’s fine, Maria. Jack has a problem which I will be tending to shortly,” my words hopefully soothing.

I excused the girl, but Jack’s reaction gave rise to much thought. He protested yet his penis suggested he oddly enjoyed. Young Maria’s quick unexpected visit proved to be quite telling. I began to more fully understand Jack... though he did not understand himself.

Thereafter, every one of Jack’s workouts ended with Maria attending, toweling him down, and preparing him for the walk to the second floor bathroom where I would bathe then milk his prostate. Yes that served to prime him, his penis stiffening as the young maid patted him dry... everywhere.

“Should I have Maria tend to your bath as well?” I would taunt, keeping Jack’s psyche tuned to my governance. “She may enjoy watching you being milked,” I would whisper, watching as his erection exposed his deep secret, uncontrollably waggling with the thought.

Chapter Twenty-One

Entering our apartment, again disappointed with the absence of neighbors in the 15th floor hallway, the midnight hour appears.

“It’s late, Jack, get your hood.”

While Jack retrieves, I glance at his schedule.

“You have Mrs. McConnell at 1:00 and Mrs. Iorio at 3:00 tomorrow afternoon. Both husbands will be playing golf so work out early and make sure you’re on time.”

I have Jack work out most mornings before making his rounds cleaning toilets. It’s basically more CFNM, the women insisting that Jack, remaining in his chastity device, offer his services in the nude. Husbands can be an annoyance during a woman’s harmless yet libidinous recreation, therefore the times must be strictly adhered to and the coordination precise.

It amuses me that for two hours work, perhaps a little longer, I charge the women $5. Yes, it’s demeaning to labor so ignobly for so little. But it’s important for Jack’s self esteem... or lack thereof.

Jack presents me with his hood. Similar to that first donned years ago, it remains of thick black latex, stretchable to fit snugly, a single hole for mouth and nose.

“Can we not charge more... or find better employment?” again broaching the economics of his endeavors.

I ignore, working the hood over his head, aligning and pulling with ardor. Task completed, I step back, assuring a proper fit, then playfully tap his nose.

“No. Your lowly servitude is good for you, Jack. It’s taken much effort to assemble the list of customers who appreciate your efforts and take care of you.”

“We could use the money...” these words rather pleading.

“No,” taking his hand and leading to the bedroom.

There I disrobe. In peering at the full length mirror, my own workouts, no where near as grueling as Jack’s, have kept this thirty five year old body in good shape. A shame Jack will never see it.

But as I lie, pulling Jack with me, guiding his encumbered head to my buttocks, I think of how gracious I am to let him taste, smell and feel.