The Party Boy Page 3

  Jack would learn that his relationship with women would be to obey, adore and bring pleasure... but not necessarily to himself.

  Empowered, I tamed the vaunted male organ. Poor Jack. Ha, ha, ha

  Chapter Fourteen

  “I’ll need a chair, straight backed, from the dining room will do,” I advise as the budding dominatrix hands me a wad of cash. I don’t count it; reasonably assured the women would not short change me.

  Jack is accustomed to rituals. I don’t want him overly distracted. I am confident he will adequately perform for me... more than adequately. But there is no point to chancing disappointment. Consistency is important.

  So I will milk and masturbate him as I have been doing for many years. Sitting on my lap, absent is my nurse’s uniform, but fully clothed. He’s adaptable to that extent.

  I stuff the money in my bag and grab the tube of unguent and a towel. As the chair is positioned, in the living room where the cadre of women can observe, some needing to stand afar in the adjoining dining room, I grasp Jack by his balls and tug. He knows to step from his make shift pedestal and follow.

  I am sure he is aware of the request, the augmentation of our CFNM display.

  “You’re going to sit on my lap like a good boy,” I coo, the words are a precursor and are known to prime his glands.

  I lead to the chair, toss the towel to the carpet, sit, then push and prod until my hooded former ward straddles my thighs.

  “Sit,” I command.

  Then I pull his hands from his head and whisk away the hood. For the first time, Jack faces his many admirers, if such is the appropriate term. He blinks, eyes adjusting. He’s heard their voices, felt their many hands and fingers. He’s performed for them, urinating at my command. But now he must return their rapt gazes, for the first time realizing how many... dozens.

  Two reactions... Jack blushes, knowing to obediently return his hands to his head. And his penis seems to stiffen more.

  At times, I must wonder if the Cialis is necessary. Yet, this is business... the entertainment business. We cannot let down (such a punster).

  “Jack, these women like observing handsome humbled men. Say hello. Give them a waggle.”

  An obedient Jack knows to pull on his pubococcygeus muscles, indeed waggling his engorged penis in response. The deed brings laughter.

  “Good boy. They want to see me masturbate you. Isn’t that nice?” I coo, mother to child.

  Speechless, Jack nods.

  “Would you like to ejaculate for them... like a big boy?”

  He nods again.

  “No, Jack. Ask the women for permission to ejaculate.”

  A sheepish Jack, never to be fully accustomed to his display of erect nakedness, speaks.

  “May I perform for you... ejaculate,” the words muddled but discernible.

  This brings boisterous laughter, the crowd greatly amused, many women simultaneously offering verbal concurrence. The budding dominatrix appears particularly enthused.

  As this daunting form of foreplay unfolds, I open the tube and begin what was a daily ritual in governing a younger Jack, coating two fingers of my left hand, the palm of my right.

  “Well, ladies, if you have not before masturbated a boy, perhaps I can be somewhat enlightening. They all enjoy anal penetration. Don’t ever let them lie to you about that,” slipping the index finger and middle finger into Jack’s rectum as I speak. “Some like it bigger and deeper, but it’s a primary male erogenous zone not to be ignored.”

  Jack’s penis confirms my conjecture, happily waggling in response, bringing more laughter.

  “And you must establish control. Jack here is trained not to touch himself, keeping his hands on his head. For your husbands and boyfriends consider tethering their hands. You’ll find there is an anomaly in the male psyche when it comes to sexual matters... they want to rush... but they are saddened after rushing. That’s why it is best for the woman to be in control. Men are immature when it comes to orgasms... want their cake and eat it too.”

  Ending my lecture, my right arm reaches to Jack’s front. I always enjoy feeling the initial spasm of joy when I first grasp his eager manhood. Jack does not disappoint. I note that he closes his eyes in shame.

  “No, Jack, look at the ladies. They want to see the expression on your face as I humiliate you.”

  True, of course, and making him peer back in turn heightens his humiliation.

  I begin. The crowd of women turns to silence. One can hear the squish of my strokes, down, up, a slow twist known to bring an explosive spark of pleasure. I am rhythmical, mechanical... initially. But when I feel Jack begin to respond with my cadence, I know to stop.

  It drives them crazy... the caprice... the unknown... the inability to gauge expectations.

  I simultaneously knead the prostate. Two weeks of chastity brings forth a nice flow of pre ejaculatory fluid. But there is an important secondary purpose in my anal penetration. I can expertly sense the small ejaculatory muscles, assess where such are in the process of bringing forth male eruption. When I feel such oscillate, I know to instantly withdraw... forcing the so termed ruined orgasm... the bane of male sexuality. Depriving the penis of the ultimate ecstatic release.

  I resume, down, up, this time a slow twist. I then rub the head with my palm, avoiding the super sensitive underside. Another motion known to bring angst.

  At this point most males may attempt to join me with their hands, speeding the process. Jack is too well trained. He merely takes it... the frustration, the pleasure, enduring the driving need to come.

  Down, up, twist, Jack’s moan of delight fires his onlookers.

  “No, Jack, keep your eyes open,” I must admonish again.

  More strokes, more pauses, more twists, more rubs, anally both kneading and assessing. I often wonder for how long an interval I can torment poor Jack.

  But then my penetrating fingers detect the telltale oscillations. Drat, the male eagerness. I immediately withdraw.

  I lean forward and blow onto Jack’s right ear. Years and years of training, his psyche knows the deed is my unspoken permission to spurt.

  “Here comes Jack,” I humorously announce.

  The standing ten inches waggles in a futile attempt to manly ejaculate. It fails, of course, needing to be gripped and stroked. Then it pulsates... meekly. I like to think it’s cute.

  “Please more,” the beseeching words raspy, as whitish goo oozes forth.

  Yes, with that, Jack’s male effluent humbly flows forth, dribbling to the towel below.

  “Finish me,” he pleads.

  “No, Jack,” I proclaim in my stentorian voice of authority. “Not tonight. The ladies preferred to see you dribble and suffer.”

  Chapter Fifteen

  Well, again to be rather punny, that was the climax of the party.

  The women continued watching in fascination as Jack’s huge erection more or less smoldered, a volcano that smokes and rumbles but does not quite erupt. Then as my penetrating fingers continued to knead the prostate, the pent up mass of semen finally came to depletion. Some women stayed to watch his organ slowly deflate, returning to flaccidity for the first time since I unlocked my naked exhibitionist; others sauntered to the kitchen where the supply of wine was endless.

  “All gone, Jack,” I said leaning forward to mockingly whisper in his ear.

  I push; Jack knows to stand from sitting on my lap. Knees wobbly, the release of hormones brings that curious afterglow of repose... but of course, no sense of ultimate gratification in ruining the potential for ejaculation.

  I arise, pick up the towel and use a dry corner to wipe my hands.

  “You’ll feel better locked back up,” I summarily inform Jack.

  He nods with solemnity. I move to my bag stowing the towel and retrieving Jack’s intricate chastity device and a tube of KY jelly. When I return to the chair, most of the women have dispersed about the living room, dining room and kitchen, many conversations, much talk about the
forthcoming wedding.

  “That was great, very entertaining and very informative,” the budding young dominatrix approaching to stand at my side.

  I return to sitting in the straight backed chair. Jack, hands remaining on his head in strict obedience, stands before me, obsequiously presenting his spent but unsatiated penis.

  I palm the shaft; Jack closes his eyes in expectation of discomfort. The girl watches with great interest as I apply a large dollop of KY jelly to Jack’s urethral opening, leaving a blob at the top of the penis tip. I then roll about Jack’s Prince’s Wand in the excess, coating it well.

  The metal tube, somewhat bulbous at the insertion end, will glide well into Jack’s urethra, the well designed ball challenging his passage way and finally coming to rest where it will ceaselessly abrade his prostate. I like having Jack constantly reminded he’s under a woman’s control, feeling slight pressure on the uniquely male gland at all times.

  “Wow,” the girl exclaims, apparently not present earlier when I first made Jack presentable for the party. “He’s kept in chastity.”

  I smile.

  “It’s business. Have to keep my mate primed and randy... for the next show.”

  I explain as Jack lurches, another bull’s eye to the prostate gland. Next I retrieve the remainder of his cock cage. A large supporting stainless steel base ring, hinged to open, eyelets permitting it to be locked closed, is slipped over his penis, the top resting at his pubic bone. Tucking his testicles and long scrotal sac through is a bit of a chore, but nothing I have not done many times. This brings the bottom of the support ring to rest at the perineum. I close it, the circle of metal snugly capturing his entire male package.

  Next comes the cage, slipping over his flaccid penis, quite tightly, and greeting the top of the base ring where the eyelets join. There I push through a small padlock, both attaching the cock cage to the base ring and securing the loop closed. Lastly, the exposed end of the Prince’s Wand is slipped through a matching opening at the tip of the cock cage. There a tiny eyelet is aligned with an eyelet at the bottom of the cylindrical cock cage. With the snap of another small padlock, Jack is returned to chastity... rather thorough and aggravating chastity... forced to urinate through a steel tube.

  I want him always eager to be released.

  “Wow,” the girl repeats. “I’d like one of those. Expensive?”

  “Yes,” I nod, patting Jack’s balls, “but for us, tax deductible,” I add with humor. “Go ahead and mingle with the girls, Jack. But hands on head... always.”

  “I’d rather not, Miss Kelly.”

  So shy in the afterglow of spending his seed.

  “Then go perch yourself on the stool and show off for a while. I’m going to have one more glass of wine before we leave.”

  It is comforting for me to exhibit Jack in chastity. It empowers. Sends a message.

  Chapter Sixteen

  Yes, one more glass of wine and I politely listen to some conversation. But I do not participate, my mind wandering.

  Exhibiting Jack, humiliating Jack, excites. My own needs are percolating and I’m moist, as are probably many of the other women, should they have propensities in line with mine. The advantage I have is that I’m taking Jack home with me and my concupiscence will be well addressed.

  Yes, I have availed myself of Jack’s tongue and lips for many years, his cunnilingus is perfect.

  It began with Jack coming to the age when sex, the curiosity about such, preoccupies the male mind, despite the clinical prostate milkings which came with almost every daily bath.

  That is when I reported... misreported... his alleged bed wetting and was given carte blanche to deal with it.

  So, one evening after a thorough milking, I began a new protocol. Jack, naked as always when alone in my presence, began to inquire about girls. Because of our relationship, me as governess, perceived asexually in Jack’s mind, having access to every inch of his superb anatomy, my ward felt no compunction, no shyness, about inquiring of the female anatomy.

  “Why do they call it a cunt? And what does it look like?” he brazenly posed one evening sitting on my lap.

  My two fingers were working his prostate, my right hand forcing his erect and dripping penis to point to the tiling. Jack was idly being milking, that clinical procedure of slowly draining him

  “The female sex organ is not to be so addressed by good boys. That’s a nasty pejorative. Pussy is more polite, but both terms encompass the female genitalia... which is rather complicated Jack,” I lecture.

  “I’d like to see one.”

  Of course, you would, you’re a nasty male, despite being obedient to me and constantly under my thumb, I think to myself.

  The discussion gives rise to thought. I can’t have Jack approaching girls at school, asking what their cunt looks like. And his early conduct, that which prompted the need for my supervision, comes to mind... spying on the maids during certain delicate times of toilet and bathing.

  So with Jack coming of age, it seems my efforts have been to delay opprobrious conduct, not rid him of it. I quickly conclude it is better that I work to temper such potential conduct, not ignore it.

  “You must be taught to have respect... and admiration... for women and the female form, Jack. Tonight I will begin the first of many lessons.”

  Seeing no more dribbling effluent, I push Jack from my lap. I then move to a cabinet where waiting is the thick canvas diaper.

  “Come,” I said while wriggling my finger holding up the imposing garb.

  In a jiffy I have the constricting contraption around his waist. At the front dangles the so termed cod piece, that which will slip between his thighs, be pulled up between his hairless buttocks and locked in place at the back, but first I must assure the impossibility of stiffening. If I am going to teach Jack to properly respect the female anatomy, he will do so without the privilege of erection. I thus assure the penis, quite flaccid after his milking, is pressed downward. I smile with its growing length. Nearing adulthood I draw back the impressive length, the tip back almost greeting his rectum. There I hold it in place as my free hand completes the restraint, pulling under and up. Then I can release his penis, now entrapped, and lock the contraption in place.

  “Ow, it’s too tight,” Jack’s pleading words bringing the satisfaction that his penis will not stir without incurring discomfort.

  “Good. Come, you’ll sleep in my room tonight.”

  And so my ‘cure’ for bed wetting began, Jack’s mother having no objection to having her son sleep with his caring, nurturing governess.

  Chapter Seventeen

  Enough. We’ve earned our fee and the girl talk is wearing. I bid all a good night, reach into my bag and toss Jack his frilly pink panties. The budding dominatrix smiles.

  “He does not object?”

  “That’s the only undergarment he’s allowed... since he was a boy.”

  Jack steps from his perch, grateful the show is over. In putting on his panties I next toss him his blanket. Bringing him to these parties in partial dishabille always makes an impression... and puts him into his subordinate frame of mind.

  When I walk him about outdoors, to and from the car, with only a blanket and panties for cover, we are within the law but otherwise Jack’s exposure is fulfilling for me and nicely humbling for him.

  “How do you find a boy... like Jack?” the girl who is so inquisitive asks.

  “You have a boyfriend?”

  “Yes.”

  “Then you have probably already found a boy like Jack. You just don’t know it. You’re an assertive girl. Only a boy with Jack’s propensities would find attraction.”

  With that, leaving the girl in thought, I take Jack by the hand... not as would a lover... but as would a mother leading a child.

  Calling out another good night, we depart into the summer night air, Jack desperately clinging to his only covering like a frightened child.

  It’s suburban Greenwich, the houses large and
sparse. Still Jack is concerned about being seen, despite his many hours of naked exhibition. It’s delicious.

  As always, his shy relatively silent interaction with me ends in departing the performance.

  “Wouldn’t it be better to allow me covering? Normal covering?” he asked finally finding his voice.

  “It makes a proper impression, bringing you to the parties half naked and easily stripped. Sets the atmosphere, wouldn’t you agree?”

  Jack reluctantly nods.

  “You performed well Jack, $700 earned for a few hours work. That’s more than your week’s earnings cleaning toilets.”

  “I could find a better job.”

  “Yes you could... but you won’t. I won’t allow it. Besides cleaning toilets suits your psyche... it’s demeaning... and that’s good for you. Those years of college coming to waste. Kind of sums things up for you, doesn’t it?”

  I psychologically disparage, never letting Jack enter a mental comfort zone.

  We reach the car. I drive, not permitting Jack to have a license.

  “We’re in New Jersey next weekend. The Craig’s List thing works well. Lots of promiscuous women want no strings access to a naked male,” I inform, starting the engine.

  I grab Jack’s blanket, pulling it from him and tossing it to the back seat. I then playfully tweak a nipple and put the car in gear. We have an hour’s drive to New York. Jack is initially silent, slumping in his seat, veiling from other drivers that he rides mostly naked... no shirt, no pants, no shoes, just frilly pink panties.

  I decide to have fun, Jack always needs to be put in his place.

  “Jack, take off your panties. Throw them in the back as well. And sit up straight!”

  He’ll ride for me naked, but for his steel cock cage.

  “What if we’re pulled over?”

  “Hopefully the officer will be female... maybe drum up more business,” I said smiling with the thought.