I am going to milk him.... austerely and clinically... not a hint of sexual implication. The maids vacuum, launder and clean the house... I clean Jack!
“Stay here, Jack. I’ll need some ice. Remain naked for me.”
It is of great fortune that the sprawling mansion of Jack’s parents essentially relegates Jack and me to a separate wing. Interruptions in my very, very intimate care are rare... such that at some point I may have Jack stripped naked for the entire time he’s not in school and under my tutelage.
With that said, in the kitchen I obtain a bowl of ice and return. Whereas I’d like to see Jack get nice and hard for me, his penis tip remains sore to the touch. So I must numb him. But he will still experience the joy of prostatic massage and a woman’s controlling touch.
“Ok, Jack. This is something I will do for you regularly. In time, when you’re completely healed and if you’re good for me, I’ll dispense with the ice. Come, straddle my thighs. Hands on head. No touching.”
And no thoughts of sex, I want to add.
I sit on a straight backed chair and position him facing away, hairless thighs spread, sitting on my lap. My starched white uniform is institutional, offering quite the contrast to his complete nakedness. I begin by applying the ice to his penis, chuckling as the coldness brings a lurch. Then I reach for the nearby bar of soap, remaining moist from his bath. It will serve as a suitable unguent for now and I coat two fingers of my left hand, holding the ice against his penis with my right. My actions are mechanical, cloaking the devious pleasure in having a naked boy, shaved to charming smoothness, straddling my thighs.
After a few moments I test, pinching at the sore tip and noting no reaction. Numbed!
“This is a special thing for good boys, Jack. You needn’t worry about soiling your panties... or how you’ll rid yourself of this nasty male stuff. Think of it as something you want to offer me... a nice gift for the woman who cares for you,” my words fostering psychological adaptation.
Yes, Jack, this is a medicine you must take... and thereafter feel better. Such is the nature of my technique. And indeed he will feel better.
I penetrate, experienced fingers instantly finding the prostate. Despite the numbness, the gland remains receptive, offering Jack that strange combination of discomfort and joy. I am going to teach him to savor it... savor my penetrating fingers well in excess of any notions of self pleasure.
Masturbation is over for Jack... self masturbation.
Working with fervor, a mason laying cement, the fluid of my young male ward oozes in abundance, my fingers kneading and kneading within, my free hand indeed milking an udder. His essence coats the tile of the bathroom floor. I note it is clear, pending puberty not yet bringing the cloudiness of sperm.
Perfect. Biologically, my timing is superb. Jack will soon be addicted to the feel of a woman’s controlling hands. Mentally addicted... not sexually. Jack knows not what that is. Not yet.
Chapter Seven
My thoughts truncate as I note that Jack, hands remaining on head, raises one finger.
Ah, all that water. He has needs and the timing is perfect, the many women acclimating to the presence of a naked sculpted yet well subdued male.
The next segment of the entertainment is included in our base fee, and prearranged with the hostess.
“Ladies, my companion Jack has a need,” I announce reaching into my large decorative over-the-shoulder bag. “Should any of you care to observe, he’ll be utilizing the back deck.”
The hostess showed me the way and suggested a convenient isolated spot while arranging our bridal shower tête-à-tête. I thus reach in my bag and extract a slim penis leash... actually to be wrapped about the low hanging scrotum, but I term it a penis leash.
This always makes an impression, leading a man about by his balls... a mirthful impression. And the girl who inquired about my position of prospective Dominatrix is intrigued. Others laugh.
Remaining hooded, Jack must follow my gentle tugs as this smiling Governess pulls to tautness and steps towards the sliding glass door. Jack must follow, of course.
The pending darkness of a summer evening looms, but enough light remains to properly amuse. And as Jack steps awkwardly, I am pleased to see the Cialis works as prescribed, a raging hard on bobbing with each step, mesmerizing the assembled female crowd.
This portion of our show has been ingrained in Jack’s psyche for many years. As stated, from the first day of assuming my duties, I took over his toilet... at least while not at school. Yes, I supervised closely, training him to urinate and stop, later holding his penis, squeezing off the flow until he learned to do it himself on my command.
As a result, our offering of CFNM entertainment is de rigueur amongst those providing kink. So to a corner of the deck, secluded as suggested, I guide a sightless Jack, pressing his shoulders to signal him to kneel.
“It’s the garden, Jack,” I whisper, alleviating him of concerns over soiling our hostess’s home.
Next I stand behind. Like the trained circus animal Jack has become, he knows he will perform for me... perform for all women. I wait until the many observers have assembled.
“I’m sure most of you are repulsed by male sloppiness in terms of bathroom use and urination. I have thus trained Jack to perform when and where I dictate,” I proudly announce.
“But he’s stiff,” a woman of age points out.
“Training... and an ingrained need to please, ladies.”
With that I lean, whispering into Jack’s left ear the sibilant sounds taught in potty training a child.
“Pssst... pssst.”
Jack clenches his stomach muscles, abdominals I have forcefully had him perfect. His penis waggles, the angle of erection slightly dipping. Then comes a forceful gush, arching upwards, between the railings of the deck and streaming to the garden below. Yes, the women are impressed. But there is more.
“Jack that’s enough,” all knowing the bladder remains in need.
Jack obediently curtails the flow. I pause looking to see the many aghast faces, a woman’s command so promptly obeyed.
“Now you may finish for me,” my follow up command coming after many, many aggravating moments... for Jack.
The stream resumes. For $300 dollars I let him finish. I explained to our hostess that for an extra stipend I will have him turn on and off the flow many times. She did not express interest. I am sure some are disappointed.
Waiting in my hand is a tissue. I dab his penis tip, a chore I have so often undertaken since youth.
“Come, Jack,” pulling his leash for him to right himself, I note that he blushes.
Yes, the masochism of the subordinate male. Psychologically, they never seem to fully acclimate to their own needs... they never seem to want to...
I lead him back to the living room in silence, my ears soaking up the many excited comments.
Chapter Eight
“Do you bind him?” the girl with interest in domineering females seems eager to learn.
“No longer. But he is kept chaste. It’s an essential part of the business.”
“No sex?” the girl incredulous.
“For him? I’ll get him off at these parties. Extra fee, of course. Sex for me? Constantly. Jack’s quite orally proficient and I find male penetration to be demeaning.”
The girl nods, quite receptive to the one sided nature of our sexual relationship.
“Tonight... will he... will he…?” the girl shy concerning her words.
“Be masturbated? No. Not in the planned program.”
“But he does... does...”
“I have him ejaculate on cue when it’s desired... normal orgasm or ruined, depending on the desires.”
“It seems cruel to leave him frustrated.”
“It’s part of the business,” I shrug. “He’ll just have that much more jism to spew at the next party,” my tone cavalier.
But the girl’s questions spur more reflections. Do I bind him...?
&n
bsp; Chapter Nine
“Your son is wetting the bed,” another prevarication in reporting to Jack’s haughty mother.
This brings a look of disgust, a subject not for discussion and a deed deemed well beneath the desired deportment of her silver spooned son.
“Well, it must be dealt with. He’s too old!”
Yes, he is. Jack is approaching his senior year. And he has no real problems, in fact, urinating for me only at my command, most times with me handling what has blossomed into a nice sized manhood.
“I have both experience and training in the matter. I’ll need cart blanche in dealing with it. He may complain... and deny that he’s bed wetting.”
“He’ll not wriggle out from under your auspices, Miss Kelly. He’s greatly improved over the years of your tutelage. A very docile boy.”
And looks sweet completely hairless and in girl’s underwear I am tempted to add.
Alas, Jack has been more than receptive to the feel of smooth silk on his shorn privates. And as noted, it so nicely tempers male belligerence.
And so Jack’s mother washes her hands of what is perceived to be a most embarrassing family problem... a complete ruse on my part.
Offered to me by one of my nursing compatriots is a special locking diaper, used in psychiatric wards with not only incontinent patients, but those with dementia who, extended opportunity, are given to masturbate most obsessively.
‘Some of the younger dementia patients will rub the skin right off their penises,’ my friend relates.
It’s comprised of heavy canvas... a thick waist belt, a formidable crotch piece locking at the back.
“He’ll need to sleep with me for a while. This will require close supervision,” I forewarn the matron of the house.
She shrugs, reiterating her desire to wash her hands, showing no concern for further details of the proffered treatment and ‘cure’.
Yes, handling Jack’s rapidly developing organs, so often milking him of his burgeoning male essence, has brought needs of my own. Yet, I cannot have carnal relations and do not wish to tempt Jack into any thoughts of such.
Thus he will be bound... at least his privates will be. And Jack will begin wearing a hood, darkness deepening his docility.
Chapter Ten
I note that my explanation of the various show offerings, different aspects of CFNM, has brought much discussion.
With Jack’s nudity, his feminine controlled urination, sparking much thought, I lead my hooded partner to a stool, provided by our hostess, and guide him to step up, there to continue displaying himself and his erection while heavy hors d’ oeuvres are served.
This for the most part is a time out, the novelty of the women’s proximity to docile male brawn somewhat wearing. But with Jack’s low hanging testicles now at eye level to many of the attendees, more hijinks are sure to follow.
I see the girl talking with others. Then all retreat, returning with their purses. It seems a collection is being taken. How inspiring!
My attention is diverted by a very athletic woman staring at Jack perched on the stool. It appears she is in the Louvre assessing a fine sculpture, more or less apprizing Jack asexually.
“He’s well conditioned,” she notes in prompting conversation.
“I’ve worked him since he was a boy,” I offer in reply. “Like to think exercise keeps a boy’s hands from his penis... at least that is the intent.”
The woman laughs. And I again have recollections...
Chapter Eleven
I want my boys to be physically active, attain some form of manly shape. But I find that in milking Jack, the resulting ennui becomes extended.
Such laziness.
However, engaging in school sports is not practical for boys in brightly colored silk panties. I can only imagine the locker room antics in changing to and from uniforms.
So sometime after my trimming of Jack’s foreskin, a few weeks into the regular prostate milkings, I engage the lady of the house.
“Jack is not one for exercise,” I inform. “Rather indolent. Unless precaution is taken, I do believe he’ll begin to fatten. Not good for a boy’s self esteem.”
I should add that neither is being stripped naked, bathed and intimately massaged by a governing woman, but on these points obviously silence serves me best.
“My, my, Jack’s father would not approve of that. Whatever should we do?”
I note it is the royal ‘we’, Jack’s mother not spending a moment of time with the lad.
“I’d like to buy some gym equipment. There is plenty of room in our wing of the house. I will supervise... assure that he’s well worked.”
“So good of you to add to your responsibilities, Miss Kelly,” the woman again readily washing her hands of Jack and his care.
And so, money being no constraint, I order exercise machines... a treadmill, stationary bike, universal gym. It’s equipment that I can use as well, I justify. And there is indeed an isolated room, a third floor attic, expansive, well windowed, with a high ceiling.
I’m going to work Jack. And it is most convenient that my ward neither has exercise attire nor did I think to order any from the equipment supplier. How thoughtless of me.
Chapter Twelve
The girl with questions of female dominance again approaches, breaking my train of thought.
“Suppose we’d like to augment that show. Can you jerk him off for us?”
“Of course, I keep Jack well primed. No party last weekend. So it’s been two weeks. And the testosterone injections keep him quite randy.”
“How much?”
“Ruined orgasm? Or do you want to see him spurt? It’s $300 for showing you all how far he can ejaculate. Ruined is extra. $100. It requires much feel and timing. Not easy assuring that he’ll just meekly dribble for you.”
I know the answer. This girl wants Jack to leave even more frustrated.
“Shush,” she advises, sotto voce. “I’ll just tell the girls you only offer ruined.”
Such a coquette, I cannot help thinking. The girl is young, cute and desirable... and eager to see a man humbled to tears.
When it comes to pending orgasms, I ruin with the best. And Jack hates it. And I love it. And with my medical training I win every time, with every weekend show expertly sensing the pending clench of the tiny ejaculatory muscles... knowing precisely when to withdraw my strokes... terminating handiwork which would otherwise put a man in ecstasy.
I see the girl working the crowd, most pitching in with twenties. A middle aged, well jeweled woman politely listens to the girl’s entreaty and withdraws from her purse a fifty. Yes, a lucrative Saturday night for Jack and me.
In awaiting the collection, my thoughts return to Jack’s alleged bed wetting.
Chapter Thirteen
Over the years, I became comfortable living in the mansion of Jack’s family. The bed wetting tale was just another fabrication, falsely evidencing Jack’s continuing need for a governess, despite his advancement into teen years.
The advantage of keeping him in panties transformed. Docility remaining, added to the benefits of having him furtively wear girly panties was the fact that a young male is unlikely to date, or least have sexual relations, while donning frilly undergarments. Plus I kept Jack’s body, though developing nicely with demanded exercise, smooth and hairless... legs and arms included.... a thorough body shave always offered at bath time. Thus if something coeducational did become serious, he’d have some tough explaining to do.
Added to this level of covert control was, of course, my supervision of glandular needs, i.e. in crass terms, the need to get his rocks off.
Yes, I milked him constantly, never deviating from the ritual of sitting him naked on my lap, penetrating fingers working his prostate, free hand ever so teasingly coaxing forth the flow of essence... never, ever stroking. Instead pressing downward on the tip, the distressing angle known to preclude ejaculation.
Yes, I know the male anatomy, know that in abridging
the ability of the ejaculatory muscles to spasmodically contract, Jack’s male effluent would instead meekly drool... and drool... and drool.
Oh, the humiliation was intense, for I would sit with me and Jack facing a mirror, his eyes not to avoid the sight of my governing hands, the puddle of resulting essence not to be denied.
Sometimes I would ice him if in a cruel mood, in so doing robbing him of just about all sense of a male sexual function. But most times letting him feel the ebb, his maleness uselessly dripping to the tiling, the slow hormonal change bringing ennui rather than the nirvana of normal male climax.
For Jack this was not a sexual thing. This was care offered by his considerate governess. Again the prostate milkings were always austere, no foreplay stirring arousal, no real intimacy but for the fact I entered him. In Jack’s mind, my milkings were the equivalent of brushing teeth.
But what of me? The question self posed.
Yes, supervising Jack’s prettified maleness brought needs. Plus I realized that introducing Jack to sexuality could not forever be forestalled. He did go to school. Classmates were dating. Hormone driven relationships were flaring. Despite the fact that I kept Jack well drained, I knew attraction to the female form would come. It was something I could delay in robbing daily of any building seed, but could not forever deter.
Thus the diaper. Jack would sleep with me... naked but for the imposing locking canvas. And since I prefer to sleep naked as well, modesty mandated he be hooded. He would feel my warmth, smell my femininity, in time taste me... but never admire... not visually.
Yes, it was time to introduce Jack to the opposite gender and the prospects of sex... under my terms.
And in an added whim of cruelty, I always diapered him most securely with his penis drawn between his legs, its growing length bringing the tip almost to his rectum. Thus the slightest tumescence brought great discomfort, not a smidgeon of room for engorgement.
The Party Boy Page 2