There are no pockets. Jack carries no money, no cell phone, no identification. He tends to rapidly negotiate the sidewalks of New York, trying his best to avoid the stares of onlookers. This assures that he will not dally and will move directly to his appointments, my supervision temporarily superfluous.
Pink, red, blue, a pumpkin orange... today I select yellow. Sandals the color of bananas, panties in a pastel yellow, slipover dress a deeper yellow. This will best draw the eyes’ attention when his undergarment flashes with every step.
“Breakfast, Miss Kelly,” Jack calls.
I finish laying out the simple but humiliating attire and join Jack in the kitchen.
“Set the treadmill for ten miles this morning, Jack. A nice long work out then bath... make you nice and clean for Mrs. McConnell.”
“You’ll milk me?”
“Of course not. We have a show in New Jersey this coming Saturday. I want you well primed. The Cialis assures you’ll be hard, not that you’ll spurt for the girls. I want that ball sac nice and full.”
My words disappoint, I know. So many years of daily prostate massages during his developing years. Yes, he’s addicted to my care, but he’s also obedient and docile as a result.
“I’m not sure what to expect. It’s not a bridal shower like last night. So I need you ready for all possibilities. They may even want you to come for them... fully ejaculate... imagine that!”
That brings a sheepish smile. I must keep Jack’s spirits up... to a certain extent. And I truly do not know what to expect. But I withhold the fact that I know our hostess to be a devout lesbian. Why she’d desire a CFNM performance I have no idea. But my Craig’s Listing is deliberately open, basically suggesting that I have an obedient, young, well hung male ready and willing to expose himself... specific activities to be discussed.
Jack finishes his dry toast and clears the table. As he departs the kitchen I smack his buttocks, rounded with exercise, hairless by way of my razor.
“I want you in a good sweat,” my tone pleasant, but Jack knowing he will indeed be worked into a good sweat.
I move to the computer. My Craig’s listing needs to be updated. In thought, perhaps I should expand our prospective audience. So for the first time under the ‘Personals’ banner, I click ‘men seeking men’ and compose an ad.
I am so wicked, typing away, imaginatively posing as Jack.
‘Sublime nakedness’ I type as an enticing lead.
Then I compose, listening to the whirr of the treadmill as I blaze a new trail for Jack’s penchant of masochism...
I am a 25 year old, Caucasian male, well conditioned, virile, well hung, well controlled by an understanding woman. She demands that I pose professionally, limits few, clothing undesirable. Fee negotiable.
So we expand, in addition to CFNM gatherings, I’m offering Jack for CMNM as well... clothed male, naked male. To my knowledge he has not before exposed himself to a man. It’s time to broaden his penchant.
I click the appropriate boxes to post, then step to the apartment door for the Sunday paper. I read in relaxation as Jack tones his nakedness. When his ten miles are finished, I will supervise some work on the Universal gym, then end with the stationary bike, watching his cute buttocks roll about.
Thereafter, perhaps I’ll dust off my nurse’s uniform for some bath time nostalgia...
Chapter Twenty-Four
Well watered, bathed, testosterone injected, Jack dresses, always with that wounded puppy look when contemplating walking the streets of Manhattan in female clothing. Since I don’t otherwise feminize, his appearance is quite conflicting for the typical passerby. A flimsy pullover dress, panties flashing beneath, the heeled sandals of a young girl, yet male styled hair, no jewelry, no make up.
Having shaved him during his bath, his arms and legs are uncharacteristically hairless for a male, bringing even more confusion in assessing his gender.
I must respond to his pouting.
“Jack, would you prefer your blanket instead? No dress, no panties... you’d need to grip it well,” I chide.
“I’d rather dress as a man,” the words defiant but his tone humble.
“I will not allow that, Jack. That would imbue male pride. You feel better being humiliated, soaking up the deriding looks you’ll receive. And besides, Mrs. McConnell and Mrs. Iorio will want you completely naked. You just need to step out of your sandals and panties and toss to the side your dress... and voila, a very presentable nude servant.
“One more glass of water before you leave.”
“But I’m full.”
“Drink another glass,” my tone stern.