Miss Elizabeth's Captive

The insouciance with which Liz described what must have been constant torment for the male gland and the entrapped phallus was strangely shocking yet arousing. Yet I reminded myself...women of authority I had always found attractive. And with panache. Yes, Liz had panache...turning what most would describe as a scene of debauchery into a casual modeling session...as if Jamie was there for no other purpose than to display his fine jewelry and amuse with his nakedness.

Such was Liz.

Well, coffee was served. My hostess took her cup and leaned back on the couch, sanguine with the scene of turpitude. I did the same, chagrined that my raging erection did not subside. Instead, viewing the girlish altered form of Jamie seemed to bring further tumescence.

I was confused...I suppose hysterical, but disguised my perplexed state well, except for my shaking hand trying to hold the full cup of java.

Then Liz took action which suggested a conspiracy.

“A cannoli? I had Jamie spend a week in training with a superb Italian pastry chef. I think you’ll enjoy even if you don’t have a sweet tooth.”

My free hand soon held the described pastry. The coffee was hot with the cup brimming. The cannoli was sloppy. I was occupied trying to effectuate neatness when Liz nodded to Jamie and the sweet boy knelt between my knees.

“Jamie’s very skilled, Sam. And I’m sure he’ll like your taste.”

A split second after Little Sam felt a warm breath, soft wetness took the standing tip of my penis into the most exquisite portal. My homophobia at first raged. I tried to put down the coffee but could not lean forward to reach the tray without bringing forth further penetration of Jamie’s throat and mouth. But within seconds it did not matter. Jamie’s gullet opened and to the sound of a laughing Liz, Little Sam disappeared entirely.

The ingenue Jamie was an accomplished fella

tor. The sensation was intensely pleasurable...perfect pressure, a swirling tongue, and a rounded piercing on the tip of his tongue was soon exploring without compunction. It was no wonder that Jamie’s speech was slurred and limited. As with the alteration of his genitals, his tongue was also transformed. This change made him uniquely adorned to give oral pleasure. His ability to receive had been taken.

“Relax and overcome your disgust, Sam, and Jamie will take you where you’ve never before been. Just remember hormone-wise he’s more female than male. And for men, I am told the oral skills of the castrated male cannot be surpassed. He knows the phallus better than any woman and he lives vicariously for the pleasure he cannot have by providing such to others.”

With the ecstatic pleasure, Liz knew to take from my hands the cannoli and coffee before it spilled. Since Little Sam was so deeply impaled into Jamie’s throat I was trapped. I had little choice but to demurely sit and be fellated...or so it seemed.

But, dear reader, what was I to do? After a sumptuous dinner with such a gracious Liz, could I physically fight and insult my hostess? I looked down at the blonde hair bobbing about. My hands entwined in the beautiful locks. I pulled such aside to see the pierced ears and the sizable gems. Then my gaze moved to see the effeminate buttocks, perfect roundness...without hair...the posterior of a girl, and a young one. I groaned with pleasure. Liz was most correct...in all my years of lustful encounters, Jamie was the best. No woman ever touched the small penile erogenous zones, sucked and applied pressure in the precise places and the exact levels as did the genderless ingenue.

I was enraptured, and my innate male macho disgust faded as the longest tongue I had ever received escaped from its confinement and began licking my scrotum while my shaft remained ensconced and the penis tip felt as if it had entered Jamie’s stomach.

Meanwhile an amused Liz just watched my contorted face and I fought the pending climax. She reached to toy with Jamie’s right nipple, appearing to gently twist the gold bar with her right hand. Her left smoothed its way down flawless flesh and grasped a handful of Jamie’s left cheek. He parted his thighs in greeting, seeming to welcome the soft warm hands that had minutes before worked Little Sam.

“Let yourself go, Sam. Jamie’s been trained since he was a lad. He’s fellated more phalli than the cheapest trollop in New York, the dear boy. And there’s no messy spitting with my little oral slave. That results in punishment. Jamie’s trained to swallow everything you can offer. And I think you’ll find the challenge amusing. Can you ejaculate hard enough to make him choke?”

Her soothing sultry voice combined with the peculiar scene...a most blemishless flesh scene. Overwhelmed. I indeed ejaculated...deeply...spasmodically grabbing Jamie’s ears and pulling firmly to ensure maximum penetration. Jamie seemed to sense the urgency, swirling aggressively with tongue, pressing firmly with lips and somehow, never before experienced despite my worldly sexual encounters, utilizing the back of his throat to create a strong vacuum like sensation.

And Liz was indeed correct. There was no choking, not even a gurgle; the ‘dear boy’ took everything.

Chapter Two

Monday, in the office, in the sexually austere working environment where daring to compliment anyone or anything wearing a skirt could erode to a charge of sexual harassment, I daydreamed about that Saturday night. It was eerie thinking about me, ‘Mister Macho’, being fellated by something once male. And to have Liz watching with such mirth...

The encounter left so many impressions. My curiosity was not satiated...it was instead raging. As I thought over the weeks of our casual dating, I realized had not even peeled the first layer of the bewildering onion that was Liz. Now for sure, when she suggested there was something ‘intriguing’ to be experienced or viewed my ears perked.

I needed to talk to someone, to exchange thoughts. But it’s not like you can take an old friend to lunch and suggest that over the weekend you had the best blowjob ever... and from an altered male.

After exploding in Jamie’s gullet, I swilled my coffee and looked at my watch. Homophobia made me excuse myself. It became my turn to announce an early departure, despite a latent desire to further explore Jamie’s girlish body. During the cab ride home I thought about Liz’s warm hands soothing the boy’s nakedness, like a mother comforting a child. Later that night in a dream, my hands took the place of hers.

“It’s his only pleasure,” she had explained with a demure smile as she waited with me at the elevator. “We can take you to new places if you care to come again.”

I was so flushed that I did not immediately perceive the pun.

Just as I was planning to call it a day, the phone rang. I almost ignored the call, picturing that a chilled and well-salted margarita in a tall goblet would extinguish my invasive thoughts of out and out debauchery.

The feminine voice was smooth, accented, sultry. It was Liz. “You seemed to be in a hurry Saturday night. Another date?” She was kidding of course.

I apologized for my hasty withdrawal. “The scene was rather overwhelming, Liz. I have never before met a castrated boy much less engaged in such...activity.”

“Jamie is twenty, Sam. Been with me for many years. He’s very much of age, now. He was quite a relief for me in my college years. I lived off campus, of course.”