The Party Boy Page 4

  So we catch the Interstate and head south.

  “You drooled quite nicely for the women, Jack; I think my testosterone injections suit you well.”

  “Can I come at the next party... for real?”

  “The terms aren’t finalized. And that’s not for me to say... and certainly not your decision. You are subordinate to the whims of women, Jack. Remember your place. It’s best for you.”

  “Will you milk me this week? Like before?”

  So many years of draining him... and now, but for his weekend duties, chastity. And a weekend escapade may or may not involve release. Such frustration for Jack.

  “No. Bad for business. We need the money. Now still your tongue. I’ll want it to be fresh and energetic when we get home.”

  Yes, his tongue... his well trained tongue. As a glum Jack returns to silence I recall the early training... under the guise of dealing with his ‘bed wetting’.

  Chapter Eighteen

  The nice thing about diapering Jack was that, in addition to essentially holding him in chastity, not even affording a millimeter of standing room for an erection, it fit so nicely into the ruse that he’d been wetting the bed. Should he be discovered in bed with me, the slim possibility of one of the maids delivering something or endeavoring an early morning room cleaning, his naked but diapered form could easily be explained. And it would be obvious that no carnal activity had been undertaken.

  And so I take him to bed, first hooding him, thick black latex, its tightness requiring effort to roll down in place and align the large opening for the mouth and nose.

  Finished, I disrobe, joining him in nakedness.

  “Lie down, Jack,” pushing him to the bed.

  When I turn out the lights and unite with him, he begins to quiver with excitement. In all his teen years he has never been with a girl, never had a girl friend. He is thus a lump of putty for molding.

  “You’re never to remove the hood... ever,” I instruct with my most assertive voice.

  I press against him, feeling a brisance of joy, frottaging skin I have labored day after day to make glabrous. I am in my element, having such youthful, masculine yet well subdued warmth to play with as I desire.

  I direct his covered face to my breasts, the lesson on female anatomy to begin there.

  “Lick then gently suckle,” offering my glands.

  Thinking of his harridan mother, in being denied breast feeding it is most likely the first time his lips have so osculated. Indeed, we’ll make up for the offerings denied in infancy. I’m so kindly.

  I moisten, of course. This day... this evening... has finally come... so many baths... so many milkings. Now I can offer more than my controlling hands.

  I can smell myself, my vagina secreting. A young Jack proves to be tender. I can no longer deny myself. I cradle his head, shifting my body, pushing downward as I position him for what will become a nightly act of chivalrous coupling... oral coupling.

  “You asked about pussy, Jack. And you shall have some. You will feel, smell and taste. You will come to savor me. But you will never, ever gaze. That I will forever deny you. Now ever so gently extend your tongue and lick,” guiding his face to my mons. “When you encounter wetness, gather and swallow. It’s a treat, Jack... a treat for a meek and obedient boy...”

  Chapter Nineteen

  We traverse the congested Cross Bronx Expressway, slowly as always. Under the many bright overhead lights, passing cars can easily spy Jack, shoulders, arms and chest exposed. Some honk. I so return the honk, smile and wave. Jack shudders, lowering in his seat in an attempt to veil himself.

  “Bad boy, Jack, sit up for me like a big boy.”

  With that I reach up to the windshield sun visor. There, in a neat row, are clothes pins, ready for quick and easy punishment.

  “Please no,” Jack beseeches in seeing me pinch to remove one.

  “Permission, Jack. Always ask permission to move.”

  With that I cautiously reach to him and snare his left nipple in the jaws, mercifully smooth. I release to pinch closed, such sending my message of correction.

  “Now sit up, hands on your head, proper posture.”

  He obeys, knowing that there are many clothes pins and many parts pink where such can be applied. Though only two nipples, his elongated scrotum is well exposed. On one long weekend trip, I dressed him well in some dozen clothes pins. His breathing became quite labored, thus I know my admonishment was effective.

  I am pleased when his nakedness, clothes pin quite prominent, brings forth more honks. He’s kept, his status apparent to the passing motorists.

  “There will be more when we arrive home. The pin is there just to remind me you need punishment. I have a certain rose bud aperture which will require your attention, Jack.”

  Analingus. He hates it. I love it as a precursor to slow unending cunnilingus. But I do not demand if often. I would not want Jack to acclimate... become comfortable with the foul deed.

  We enter Manhattan, traverse the FDR, turn off and fortunately, the hour late, there is little local street traffic.

  Into our apartment parking garage, I remove the punishing clothes pin, the rush of returning circulation bringing a comical gasp for air. Jack takes a deep breath, steadies himself then turns to reach back for his panties and blanket.

  “I don’t think that’s necessary, Jack. It’s Saturday night. Theresa’s on duty and she enjoys looking at you on the security cameras.”

  Yes, Theresa, a woman of color, size and authority, is one of us, well aware of Jack’s subservience... naked subservience. As the night security woman, she will follow our progress on video, through the garage to the internal elevator, in the elevator, down the hallway to our apartment.

  Besides enjoying Jack’s embarrassing exposure, in a satisfying manner, I placed her in a position in which she would be ill served to disclose Jack’s curious penchant. On Tuesday mornings, one of Theresa’s days off, I have Jack tend to her apartment. There, naked and in chastity, he cleans her bathroom... her toilets... as I demeaningly reference Jack’s weekday employment.

  Something about being served by a naked Caucasian male brings a thrill...

  “What about the neighbors?” asked Jack expressing concern.

  “Some you already clean for. If we encounter others, we’ll just offer your services and trade for their silence.”

  It’s true. Jack likewise cleans the bathrooms of some half dozen fellow tenants. Odd that it is so easy to arrange new clients for his services. Modest, harmless kink... more prevalent than most would think.

  “Come, let’s go. I want to be served orally. Your exhibition has once again placed me in a mood.”

  A nude caged Jack exits the car, scampering like a scared rabbit to press the elevator button and minimize potential encounters, at least in the garage.

  This segment of what Jack must perceive as a long journey really is not that perilous. The opening of the parking garage door would signal the pending arrival of a neighbor long before he or she would spot a naked Jack. Still, seeing my former ward in such panic brings delight. And I know within that tight steel cock cage, his penis stirs... the masochistic reaction never to be completely stifled.

  I gather his blanket and panties and slowly sashay behind, taking the time to admire Jack’s physique, many years of my handiwork. Yes, Jack is a divine pile of masculine flesh, well muscled, the workouts I demanded as his governess continuing daily. It’s part of the business. I’d have him working at a male strip club but for the need to remove his chastity device and his propensity to harden before fully clothed women. I’m sure management would not appreciate such a lustful gesture of male condescension.

  I am almost disappointed when the elevator arrives with no passengers. Oh well, onward to the 15th floor as viewing Jack’s exposed muscling brings memories...

  Chapter Twenty

  As noted, since participating in after school sports was not practical for my silk pantied Jack, I inveigled the matro
n of the house to purchase an array of exercise equipment.

  The third floor attic was turned into a gymnasium and beginning in his mid teens, Jack knew to come straight home from school... really nothing else for him to do... and report to me in the attic.

  There I disrobed him, a ritual upon which I insisted, making him stand most passively with hands on head as I stripped him of every inch of clothing. Yes, he would exercise for me naked.

  “There’s no point in piling up more laundry for the maids, Jack... sweaty shirts, shorts and socks,” I succinctly explained.

  It was with great interest on those many afternoons that day after day I watched his penis blossom and the fruit of his scrotum fully ripen into the testicles of a young man... a well hung young man... a well subjugated young man.

  Treadmill work, miles on the stationary bicycle, I insisted on the development of a manly chest as well, bulging, well proportioned pectoral muscles to be honed on the Universal Gym.

  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.

  He begins to protest the odorous task. I reach back and further press his face into my crevice.

  “Shush.”

  In absorbing the first of many tender licks, Jack’s concern over economics brings thoughts. He’s not... we’re not... as impoverished as he believes, his trust fund well invested and stable. I know... I am the trustee.

  Chapter Twenty-Two

  It was decided that Jack attend college locally, New York University. So for the most part, in approaching his majority, my tutelage remained about the same, somewhat amending the times of Jack’s naked workouts, baths and milkings to accommodate his class schedule.

  Times were good, until tragedy visited. Jack’s father, a busy constantly traveling multi millionaire businessman, died. Though never close to his mostly absent father, news of his massive heart attack, while in the desolate mountains of Central America purchasing lumber, brought sadness... and revelations.

  It seems the harridan woman of the house was a second wife, not Jack’s biological mother. Thus her standoffishness with regard to Jack and his care came to be better explained.

  Apparently unknown to Jack’s father was the disdain his second wife had for her stepson. The will left everything to the harridan, nothing for Jack, as apparently Jack’s father assumed his second wife would continue his care. Compounding Jack’s grief was the announcement, shortly after the funeral... a tellingly short interval... that the mansion would be sold... that Jack’s step mother was moving to a newly acquired estate in Palm Beach... and that in approaching his majority Jack was not welcomed.

  His Stepmom had no legal or financial obligations to Jack... nor was she going to offer any generosity.

  It was I who took charge of the inequitable situation.

  An attorney en
gaged by me advised Jack that, in nearing age twenty one, he had little recourse. He could however try tying up final probate by contesting the will. But the battle would be uphill. The second marriage was of some eighteen years, Jack’s biological mother passing on when he was a toddler.

  Well, as the lawyer suspected, the harridan settled, apparently not wishing to delay dispersing estate funds and spend on legal fees... though there was also eagerness to join some gigolo in Florida. I insisted that a spendthrift trust be established, the settlement modest, income to be dribbled out based on my authority as sole trustee. Since the attorney was my hire, such was established without objection.

  Thus my financial power over Jack.

  Chapter Twenty-Three

  A great night’s sleep, though passing out from multiple orgasms better describes my state of unconsciousness.

  I arise, a weary Jack, tongue worn, sleeps. I don a robe, use the bathroom, peel off Jack’s hood, then head for the kitchen. I will make coffee. Jack will prepare breakfast when he finally musters the energy to arise.

  I take a sip of java. Then hearing him stir, step to the bedroom. Jack will have toilet needs and I must assist. As stated, Jack will always have my assistance and supervision in the toilet... a regimen begun years ago from day one as his governess.

  Bladder full, Jack wordlessly steps to the bathroom. I follow. When he moves to the toilet, hands go to his head and I reach down and grasp his cock cage, aligning the opening of the Prince’s Wand.

  It’s both intimate and humbling, ceding dominion over a basic function of the male to a woman. But necessary, for I practice my control. Its’s an aspect of our weekend show to have Jack open and close his bladder at my command. It requires discipline and a will to be governed by a woman. Jack has developed both and midway through his business I command him to halt.

  Jack complies, never knowing for how long I will demand he hold his flow. Feminine caprice is important... submitting to it at all times paramount.