“I think you need better supervision, Mr. Winthrop.” The woman stood and thrust back massive shoulders, which effortlessly bore the burden of huge mammary glands. She strolled to a door, opened it and gestured.
“Your new office.”
It was merely a cubicle … no windows and with the only egress being Grave Hobson’s capacious suite. And then, as she laughed at my shocked reaction in peering at the tiny new office of Samuel L. Winthrop, III, Ivy League MBA, something struck me. It was the throaty laugh, one which I heard at Miss Elizabeth’s dinner parties. The laugh that was spurred by my suspended nakedness, my plugged rectum and a standing Little Sam. The laugh that accompanied the exploring fingers and the determined squeezes of the inflatable plug.
I lost it. I went into a funk. Did she know it was I hanging hooded in such ignominy in Miss Elizabeth’s penthouse? I was speechless.
Her persona would indeed fit the mold of a woman who would so much enjoy making a man squirm, as evidenced by the joy she took in showing me my new office.
“Be in early tomorrow, Mr. Winthrop. I take coffee at 8:30. Make it black with sugar. And we’ll need to talk about those stock loans. Your next bonus, if you receive one at all, isn’t going to cover the next principal payment. But I’m sure we can work something out.”
Again the throaty laugh as I turned to stagger to the door.
But then my question, the one concerning her ability to identify the naked form so obsequiously hanging plugged and erect, was answered. As Grace Hobson’s sizable frame moved to return to her desk, we brushed up against each other, ostensibly in one of those encounters where we both stepped in the same direction simultaneously. Our torsos met, but a quick hand goosed the hard plastic under my zipper, feeling for just an instant the cage entrapping Little Sam. And whereas most women would be dumbfounded in encountering such a quirky device, Ms. Hobson’s brief copping feel brought an evil smile and more laughter, thereby closing the door on any doubts I had about her identity.
As I reached for the door handle, her laughter became irritatingly uproarious.
I needed a margarita...chilled and well salted. I fantasized scantily clad Jamie kindly serving me one while allowing Little Sam to bask in transitory freedom. And then came thoughts of his tongue and knowing hands...
Chapter Twenty Two
The ensuing week was mentally wearing. Ms. Hobson was given to constantly buzzing me in my tiny cubicle, seeming to beckon my attention to the most minute administrative matter.
At home I would arrive to find reminders concerning the building’s change of ownership. Utility service was interrupted at the most inconvenient times. Elevators were slow. Repairs were not timely made.
Then there was dealing with Little Sam. Early morning applications of cold water were required with Miss Elizabeth’s predicted nocturnal attempts at erection seeming to happen regularly just before dawn.
To escape the clutches of Ms. Hobson’s iron fist, I needed to complete a deal. And of course nothing was getting done and the termagant, unlike Winston, constantly reminded me of my ineffectiveness.
Then the cat was completely let out of the bag when. After sending me for coffee, I leaned over to serve her, and her beefy hand, one that I had surreptitiously felt so many times while suspended in Miss Elizabeth’s living room, grabbed the cage of the CB-2000.
“It’s no wonder you’ve agreed to have this locked up, Sam. You have balls but they’re not used for anything.”
She twisted, bringing pain and a spontaneous groan. Then the throaty laugh followed her release. As she stirred her coffee she slid open the top drawer of her desk. There, lying in plain sight was a very familiar padded manila envelope bearing the return address of Miss Elizabeth.
“I’m becoming very fond of home movies, Sam. Care to view one some evening?”
I demurred and humbly retreated to the confines of my little office. I was stunned. I was closer to being unemployed than I had suspected. Ms. Grace Hobson was toying with me like a cat playing with a mouse just before the kill. Making me go for coffee. Verbally taunting me with every opportunity.
She had the videotape. And I pictured the feigned surprise, disgust and shock when it was time for the coup de grace. She would ‘regretfully’ deliver the contents of the envelope to the executive committee, dutifully drawing their attention to documented evidence of moral turpitude. And how convenient that such an act would be committed by a borderline producer, someone about to be deemed expendable.
I quietly called Miss Elizabeth’s apartment. I so much needed comfort. And besides it was Wednesday, which had over the past eight weeks become the day for a regular early evening shaving and scrotal massage.
Contemplating Miss Elizabeth’s bizarre solution to my entrapment, the pressure to produce, Ms. Hobson’s demands, losing my apartment, the hormonal buildup ... all added to the downward velocity of the emotional roller coaster I was riding. And the only way up was being with Jamie.
He had the only key.
“Miss Elizabeth is out, Mr. Sam,” the halting young voice explained.
I took advantage, informing the blond ingenue that I was expected but would be arriving early. “I need the key and a margarita,” I brazenly insisted. To hell with Ms. Hobson and her opinions concerning my balls, I thought to myself.
I hung up. Then for the first time in my career, I sneaked out…, past Ms. Hobson’s nosey male secretary, into the hall, down the elevator. It was late afternoon, but Ms. Hobson had been adamant in procuring my assistance with mundane paperwork into the late hours. Tonight there would be no assistance. I needed Jamie.
The walk was short, but seemed to be endless. The doorman, having seen me twice or more per week for the past eight weeks sent me through. The elevator was not fast enough but finally stopped. When the doors opened I had already removed my tie, unbuttoned my shirt and unbuckled my belt.
I did not wait for the elevator to return to the ground floor on this visit. I just stripped, threw my clothes into the closet and grabbed the cuffs. I rang the doorbell and was kneeling to strap on the ankle cuffs when my blond, angelic key holder opened the door. I looked into the pretty blue, smiling eyes. Jamie had spent the time to pretty himself after my call. At least I convinced myself that’s what happened. There was mascara and definitely some lip gloss. And the smile. The ‘come hither’ smile of an expensive lady of the evening...on a little girl. At some five feet three inches, I almost looked Jamie directly in the face when kneeling. And ‘she’ was radiant. Attired in a white cashmere pullover sweater, a white cotton skirt so short that the crease of where ‘her’ thighs connected to ‘her’ hips flashed, and nothing else. Jamie wore no undergarments, the golden balls clicking noticeably. And the tiny feet were bare.
The hormones. Miss Elizabeth stated that she was increasing the level of hormones. Could such work that quickly? There seemed to be no masculinity remaining.
Jamie giggled ... as would a little girl making mischief when left home alone, as she watched me finish. When I stood, she helped with the wrist cuffs then clipped them together when I placed them in the obligatory position for entry to Miss Elizabeth’s apartment.
I stepped in. Jamie closed the door and gratefully the tiny hands held up the key to the CB-2000. She smiled and the gratitude I felt as the lock sprung open and the cage was tugged away was indescribable. The warm softness of her fingers had Little Sam standing before the cuff ring, a two-inch-diameter circle of comfortable smooth plastic, could be removed. And then, I suppose in her state of envy, Jamie knelt right there at the door, extended her tongue and lapped away at my scrotum, occasionally sucking in a testicle and swirling her studded tongue round and round.
“I need to be sucked,” I sententiously proclaimed, as calmly as I could, not wishing to sound too beseeching.
“I shave you,” was the terse reply.
Jamie stood and tenderly took my balls in her hands to lead me to the examination room. She was indeed a loyal servant. Contact with Li
ttle Sam was forbidden and she followed the rules.
I was lathered and shaved, the straight edge seemed to effortlessly glide with Jamie working her way around Little Sam, who celebrated his freedom by standing at attention as if at parade rest.
I thought about my circumstances. Blackmailed into over eight weeks of chastity, and not understanding the ransom to be paid, working for the termagant Ms. Hobson, in debt, limited foreseeable income, about to be homeless. Little Sam needed more.
And as Jamie toweled away the shaving cream with a divinely hot moist towel, something snapped. I realized that I needed more than the key and a margarita. That roaming about Miss Elizabeth’s apartment naked, wrists bound and penis standing was not going to assuage for the weeks of torment. I needed Jamie. I needed that tongue. I wanted to press that smooth warm and hairless flesh against mine…the sweetness...the innocence.
My right wrist twisted in frustration and I realized that in my haste I was not as attentive as usual in tightly securing the cuff. As Jamie dabbed with the towel and devilishly pursed his lips to blow on the underside of Little Sam, I was able to slide my hand about within the cuff. I smiled with the tantalizing sensation of Jamie’s tease. But I also smiled because in moving my hand, I encountered the knob of the small spring loaded piston that held closed the ‘D’ clamp. It moved as the tip of my index finger pushed.
“A margarita, Jamie. Please may I have a margarita?”
“Already made, Mr. Sam.”
A subterfuge but I would eventually imbibe. And the request had Jamie prancing to the kitchen. He would return quickly but I did not need much time. The ‘D’ clamp yielded and with hands free to move, I took off the cuffs. For the first time in eight weeks both Little Sam and my hands were free. And whereas I needed the mental and physical release of wickedly stroking myself to glorious climax, I abstained.
The patter of Jamie’s little feet brought evil thoughts.
The little ingenue returned to the examination room, margarita perfectly presented, smile radiant, eyes glowing in femininity, but wearing that cocktease of a skirt. That would have to go. I wanted Jamie and I wanted her naked.
Chapter Twenty Three
The next day I called in sick, needing time to think. In leaving the CB-2000 behind I knew Liz would act quickly and that the tape would be mailed or if Ms. Hobson indeed had it, the executive committee would be viewing it even sooner. But I had escaped the Stockholm Syndrome. In that I reveled.
Friday, I had a long scheduled business meeting in Chicago. I did not bother checking in with my defacto new boss, Ms. Hobson. She knew the appointment was on my calendar. I just went, returning Friday evening well after business hours.
Upon returning, there was no message from Liz, which I thought odd. So I reveled again, this time in bachelor’s freedom all weekend. With Little Sam having been more than satiated, I just watched sports. Drank beer with a few friends. Went to see the Giants try to play football on Sunday.
I knew Monday would be tough. Facing Ms. Hobson, if she was in on the conspiracy, would be challenging. My job would be gone. I knew it but figured I had a couple of weeks if not months of pay coming.
I was wrong.
The security personnel would not let me into the building. There was no explanation.
I returned to my apartment building to find a UPS box waiting, filled with personal stuff from my office. The doorman handed me a letter. I read it in the elevator. It was an eviction notice for non payment of rent with my latest rent check enclosed. It had been returned from my bank due to insufficient funds. A call to my local branch revealed that my latest paycheck, scheduled for automatic deposit on Thursday had not been wired to my account.
I had to admire the speed with which the no-nonsense Ms. Hobson worked. I did not admire the legality of her action. One cannot be terminated retroactively and I was legally owed money. But on the other hand, lawyers require good funds and the legal process takes time. I had neither.
I moped about, consoling myself and mentally trying to justify for my brash action. I dispensed with having any margaritas, opting for straight tequila.
On Tuesday I awoke somewhat hungover to the sound of the house phone. The doorman announced the arrival of a letter by special messenger.
“It looks important,” he laconically reported. With his years of experience, he readily distinguished important versus the likes of trifling love notes.
I dressed hurriedly and went to the lobby to retrieve it.
A very stern looking envelope with the embossed lettering of a law firm awaited. My first reaction was more bad tidings about my eviction. I was wrong. It was from the two-person law firm of Regal & McCabe and signed by Suzanne Regal, attorney-at-law.
I held it up to scan and a handwritten note within fell to the floor.
I read the formal letter first which indicated that Samuel L. Winthrop III and his attorney were invited to attend a ‘settlement’ conference with one aggrieved ‘Ms. Jamie Lindsay’ and her guardian ‘Ms. Elizabeth Mouquod’.
Guardian?
I picked the note off the floor. Liz’s signature caught my eye.
“Sam, I trust you can attend. For convenience we’ve arranged to use the MacDonald, Bear audio visual facilities.”
Yes. I had recognized the address.
I could not afford an attorney and the letter seemed to suggest settling something of which I was not aware and for which I certainly had not been served.
But the need to meet was compelling. Liz was due an explanation if not an apology. And I needed financial help and some answers. Dare I begin mailing resumes if that videotape lurks?
The invitation was for the following day, Wednesday. I was accustomed to meeting Jamie on Wednesdays.
I could not refuse. I had nowhere to go and nothing to do other than to put together a curriculum vitae. And the tone of the letter was ominous.
Chapter Twenty Four
I did not sleep well. I dreamed of Liz. Authoritative, dashing Liz and her ingenue servant, the obsequious Jamie. How much I enjoyed being in their presence, being under control. The deep depravity of being displayed naked, bound, erect was so peculiarly stimulating.
But it was over. I had broken out of the Stockholm Syndrome. It seemed so simple, unclipping the physical bonds, finally having my way with Jamie and then moving onward.
But then I awoke with Little Sam preparing to cut diamonds. And whereas I would normally give the little guy some swift strokes, explode into a tissue and return to sleep, the ultimate urge was not there. It seemed boring.
The urge was for Jamie...and for Liz to be supervising while I once again took advantage of the effeminate body and the envy ‘she’ displayed for my engorged penis...one which ‘she’ had so vicariously pleasured, and with such zeal.
Half sleeping, half daydreaming I dragged myself to the bathroom. In preparing for the 10:00 a.m. meeting I did a strange thing. I shaved my groin.
Had I truly escaped?
With plenty of time on my hands I walked to my former place of employment. Despite the desperation of my financial and living status, Jamie and Liz occupied my thoughts. I could think of little else, visualizing the perfectly rounded girlish buttocks, the tiny restrained penis, the puffed nipples, the pretty hair and blue eyes. And of course Liz is always in the fantasy, standing over my nakedness in full dress, confidently uttering, in her low smooth and sultry voice, supremely humiliating commands and requests.
Security escorted me to the 35th floor. There would be no diversions to bid farewell to colleagues or to network for future employment. I was taken directly to the executive conference room where in better times I enjoyed the respect of MacDonald Bear’s executive committee and earned the admiration of my fellow workers in receiving killer bonuses for negotiating, clenching, and completing huge merger deals.
And now I would humbly sit while an ambulance-chasing lawyer negotiated, clenched and completed some type of ‘settlement’.
The room was emp
ty at my arrival and I had a moment to marvel at its size, accouterments, and the electronic wizardry cleverly disguised by tasteful carpeting, lavish mahogany paneling and thick dark red curtains which eliminated all daylight.
I sat in the middle the long conference table. The security guard remained, positioning himself just outside the door. Within a minute, the raven-haired goddess of Fifth Avenue appeared, professionally attired in a black turtle neck and charcoal pants suit. With her was Jamie of course, strolling with Liz holding his left hand in her right. But it was not Jamie the servant; it was Jamie the little girl. In what I am sure was deliberate contrast to Liz’s drab attire, Little Jamie wore a lightly colored dress of blue and white, white socks ending halfway up her calve, white cotton gloves, black pumps and a black purse, the size of which made it impractical for anything other than to falsely portray the bearer’s chosen gender.
As I scanned the young beautiful creature, the projected image got worse, or better, depending on the viewer’s proclivities. The blond hair, formerly in a pageboy, had grown enough over the weeks such that it was tortured into pigtails. Though comically short, pointing skyward rather than dangling toward the neck, the two opposing clumps of hair sent a definite message to the unaware: Jamie was a little girl.
The makeup was no longer expertly applied and alluring. No for this ‘settlement’ conference it was thick and somewhat sloppy, suggesting to the viewer that ‘mommy had let the little girl try to apply her own lipstick and rouge’. The results prompted a reaction of ‘cuteness’ from the unknowing admirer. In me the reaction was one of nausea.
“Liz, I’m sorry,” I blurted as the duo sat opposite to me. But she just looked at me blankly and after a moment turned to help Jamie properly sit. His dress rumpled when he had taken the chair, hinting that it was not a garment worn with familiarity.
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