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Part 3 of Growing Up Insane
By: JethroJodhpur   Posted: 16th June 2008
 
In my profession, the oldest I am told, one meets all sorts of individuals. Some are quirky, others needy. Some are downright mean and others are strange. However my life was decidedly incomplete until I encountered Tabitha. She flounced into our little house that wasn't a home and I was the lucky one to take her on as a client. In those days we were trying our damndest to become upscale because that meant we would be encountering men and women more apt to be generous tippers for our unique services.

I sensed that there was something not quite right with Tabitha. She was what I'd call statuesque with a good-sized set of jugs, long legs and a face I'd describe as more handsome than beautiful. Her voice was a bit odd as well, sort of high pitched at times and then turning husky from word to word. We arrived in my boudoir and began negotiating a fair price for my services once we had established the ground rules for whatever sexual activity that we would engage ourselves in.

Tabitha's ideas concerning sexual congress were a bit strange, not harmful strange, just strange. I suggested the standard girl on girl activities, and threw in a few curves such as an extended period of rimming, with each partner alternating as the aggressor, and held out the possibility that I might deign to engage in some mild form of fisting if the fee was adequate for such an endeavor. It was not until I mentioned that some of my female clients were partial to using or having replicas of the male genitalia used on them, that Tabitha brightened considerably.

In that husky-high voice she asked for some detailed explanations about who was to do what to whom. We compromised on a configuration where I would be prodding Tabitha in her ass with one of my standard issue strap-ons modeled after one of the more well endowed members of the porn star fraternity, while at the same time I was enjoying the feel of her "magnificent mammaries". Those were her words, not mine.

While Tabitha got out of her clothing, revealing a set of tits that made my mouth water, I set about rummaging in my closet to come up with "old reliable", which is the name I had for my tried and trusty-true strap-on. I opened my robe and donned the black rubber reamer. I turned and got the shock of my young life. For one of the few times in my career as a professional sex worker, my jaw dropped and my mouth took on the appearance of a fly catcher.

Some might say that Tabitha combined the best of both worlds; her tits were damn near perfect and that baby python hanging from between the legs of whatever it was would put all but the top one-tenth of one-tenth percent of the male population to shame. I had just gotten my first good look at one of those transsexuals, close-up and very personal. A better way to describe it would be to call it a work in progress, since it was obvious that it was still in transition based of the size of that cudgel dangling there for me to feast my eyes upon. At that moment I had this crazy thought bouncing around inside my head that the two of us must have looked very much akin, me with my fake dick and him with his fake tits.

For reasons that were most obvious, this revelation had taken the thrill off of what we had been about to consummate. Tabitha was blushing from head to toe, caught in the act of impersonating a woman. Her or his equipment was at half mast and falling faster than a barometer just before a hurricane hit. I thought the poor dear was about to burst into tears, and then it did, releasing a deluge of saltiness from its eyes that rolled down those adorable, high cheek bones to drip off that chiseleed jaw and finally be deposited on a pair of breasts that were so realistic I expected them to give milk if I sucked on the teats.

I felt ridiculous standing there with my strap-on bobbing up and down from my crotch while this poor creature acted as if it had not a friend in the world. In less time then it takes to tell I took it off and put my robe back on. Then I settled down beside the tearful tranny and tried my best to console the poor creature. It is not possible to explain what happened next. I brushed a tear away from its face and then those bee stung lips acted like a magnet and the next thing I knew, we were locked in a kiss that could have melted steel. Damn, that Tabitha could kiss! I automatically parted my lips and damned if what seemed like a yard of hot, wet tongue didn't begin taking up light housekeeping inside my mouth.

Things started getting quite serious in one big hurry. That limp length of flesh hanging down between its legs was growing like some weed on steroids. The next thing I knew, it was trying to poke a hole in my belly. I reached down and without giving it too much thought guided this monster into my treasure trove as my dear old momma called my money-maker. Now I had yet to experience the joy of giving birth (pushing until I turned blue in the face as it felt as if a small tree was being forced from my pussy), but this close encounter with Tabitha's male equipment gave me a pretty fair inkling what lay in store for me one of these days.

Tabitha took unfair advantage of her strength and size, rolling me onto my back as if I was just a collection of skin and bones. Then I felt this ache that kept growing as Tabitha sank more and more of that tree trunk into my poor pussy. I may have been on the young side, but due to my occupation I had been stretched almost to my pussy's limit by any number of men with large appendages. Tabitha was a special case however, and as time passed it became apparent that this creature of loveliness and charm had the kind of staying power that was legend.

At the time I did not realize that those in the process of crossing the great divide separating the sexes paid a heavy penalty for their cheekiness. Putting it another way, the spirit was willing, but when it came to delivering the goods, the female hormone shots that were assisting the change got in the way of progress. To those of you thinking that my vocabulary is a bit much for one so uneducated, be advised that for lengthy periods my only reading material came from two sources, one the holy bible and the other a copy of Webster's New Collegiate Dictionary.

It took some doing but I managed to disengage myself from Tabitha. After taking a few deep breaths I returned to the fray, but this time I was the aggressor. I reasoned that perhaps oral stimulation might be more to its liking and so I attached my mouth to that reptilian protuberance and began applying enough suction to create a mighty vacuum against which no cock was able to stand without delivering.

Tabitha just lay back and watched my cheeks hollow and puff out as I worked diligently to extract whatever those shrinking testicles were producing in the way of seminal fluid. Alas my efforts came to naught; I had been drilling for oil in a dry hole it seemed. Now it was my turn to feel rather insecure. I had failed at the most basic function of my profession. What was to become of me if word got out that I had failed so miserably and with a tranny to boot? This only goes to show just how ignorant I was concerning the plumbing and behavior of your typical debuting transsexual.

I guess Tabitha felt my discomfort for she or he gave me a shy smile and patted my head like I was the family pet who had just chewed up one of its favorite shoes. The sigh it let out was enough to almost make me renew my efforts, but I restrained myself. For the next half hour or so I sat there mesmerized by the amazing tale that Tabitha related.

My client and bedmate started things out by giving me the proper nomenclature to use in describing this exotic sexual creation. Tabitha, nee Timothy, was a young (nineteen years old) transsexual to-be who had just taken the first few steps in changing from male to female. It or semi-she, as Tabitha liked to describe this in-between state, was a few inches short of six feet in height, slim with the beginnings of some exceptional curves thanks to the first of what would be many surgeries and the regular ingestion of female sex hormones plus sex stimulants that kept Tabitha in a high state of readiness for any and all forms of intercourse involving members of both sexes.

I could not help but stare at what appeared to be one of the most perfect sets of tits that I had ever seen. When you're a 34B on your best day, you spend lots of time fantasizing about having bigger and better shaped boobs, especially when you are working in my field. Tabitha noticed the attention I was giving these beauties that sat on its chest. I got one of its shy smiles and then it floored me.

"These are a gift from a very dear man, who like me has issues when it comes to his sexuality. You may have heard of him, he's Carver Cleaver." I was stunned; anyone who knew anything about the subject of enhanced breasts knew who Carver Cleaver was. He was to boobs what Michelangelo was to marble. I felt as if I was standing before an altar; here before my dumbstruck face was a perfect example of his fantastic talent. "Why it, and not me?" I said to myself as my mouth began to water at the sight of these twin miracles.

Tabitha was deliberately vague on how the two of them got together, but together they got, in a big way. I figured they had too much in common not to match up once their paths crossed. If the truth be known, Timothy/Tabitha was a rather conflicted individual. The desire to assume the trappings of a fully developed and near fully functional female was driven by the Timothy side who was extremely attracted to those mysterious creatures that seemed to be from another world. However at the same time the old Timothy was loathe to give up the impressive physical equipment that came with his maleness, since it too was a method of attracting and interacting with those marvelous female creations.

Adding to this sea of conflict was the personality of Timothy/Tabitha, very submissive and easily led. In this state Tabitha was totally vulnerable to anyone willing to take the time to direct this lost soul down whatever path suited their own purposes, whether or not it would benefit Tabitha. Such was the case when Timothy encountered the equally ambivalent Carver Cleaver, who like himself was struggling with his sexual identity.

Cleaver had taken a different solution than the one Timothy was seeking. He had surrounded himself with those who still retained male characteristics, and were dedicated inwardly to the very maleness that Timothy was trying to shed. It was this environment that Timothy found himself in when he took up Carver Cleaver's generous offer to come and stay under his roof while Carver prepared him for a series of surgeries that would partially achieve his objective of joining the female ranks.

There was a price to be paid by the nineteen year old changeling, and Timothy was only too glad to pay it for the promise of freedom from his current state of being. Carver and his gay friends enjoyed his long, thick cock which never seemed to grow soft no matter how many times they drained the attractive youth's churning testicles. This period was not to last as the female hormones that he was receiving from his master and mentor were slowly sapping his ability to generate sperm.

Timothy gladly offered up his tight asshole to Carver and his friends. It would open like a flower when Carver or one of his confidants pressed his tongue against the puckered entrance to that dark tunnel. Carver doted on Timothy's tight channel by the hour, taking his time as he probed deep and stretched the tender funnel of flesh to conform to his generously sized prong.

Initially Timothy proved to be nearly inexhaustible despite the challenges his companions provided on a nightly basis. Weekends were even more stressing. The youth would lie almost in state, manacles ringing his wrists and ankles so they could rearrange their prey into any and all types of configurations that crossed their fertile imaginations. It was a rare moment when there wasn't a thick cock buried in his asshole while another thrust down his throat and either a hot mouth or calloused fist was busy trying to bring the young tranny wannabe to still another ejaculation.

I detected some pride in Tabitha's voice when she described how much spooge they could force from Timothy, their boy toy. She smiled somewhat nervously as she related a situation that could only be called apocryphal. The equipment of her former self was hooked up to a small scale version of a milking machine and it was run continuously for almost twelve hours, yielding nearly a pint of a translucent fluid that had a mild salty taste and the consistency of skim milk. To make sure that Timothy was giving everything possible they dosed the teen with powerful sex stimulants and stiffeners, the latter being a souped up version of the popular little blue pill that made a certain portion of the male population capable of doing what they formerly did with ease when they were younger.

As if this wasn't enough to cause him a heart attack, additional stimulation was provided by means of vibrating dildos which were forced deep into his anus and run until their batteries died. Others ran vibrators over his scrotum and provided even more stimulation to his swollen testicles which prior to this event had begun to shrink in response to the massive amounts of females hormones he was consuming.

As the hours went by, word spread throughout the gay community about the incredible performance that this handsome youth was being induced to provide. At the half way point in this ordeal, there was standing room only at Carver's home. Naturally everyone wanted to participate in this epic experience.

Timothy was fed plenty of thick cock that spurted and squirted enough cum to give the tranny wannabe a rather large tummy that was the butt of jokes as the day wore on into night, his cock still hard and his tired testicles still delivering small amounts of fluid into the collection bottle. There is an urban legend that the contents were auctioned off afterwards for nearly a thousand dollars an ounce, and is being stored the same way as extremely rare wines, and consumed only on very special occasions.

The machine was finally turned off after it had milked Timothy steadily for an hour and a half at its highest speed setting, collecting only an occasional dribble of a clear fluid that looked almost like glycerin. During that last, utterly exhausting period the lad's face grew flushed, becoming redder and redder as the machine literally began to suck the life from the helpless changeling.

Some claimed that they could actually see his heart pulsating violently beneath the sweat-soaked flesh as Timothy writhed in mortal agony. Those who knew about such things, claimed that during that last ninety minutes, Timothy had at least six dry ejaculations, a most painful process that can weaken the stongest of studs. Despite this Herculean effort, six hours later the youth provided a substantial amount of his fluids for the edification and amusement of a number of queens who dropped by unannounced to be entertained by this phenomenon.

I was so wrapped up in this tale that I lost track of time. Then I was reminded in no uncertain terms by my mother who barged in, not batting an eyelash at the sight of my customer who displayed his/her all, and berated me for not meeting this very important client in the parlor as befitted his status. I begged Tabitha to go downstairs and remain there until I finished entertaining my next customer. I had to know all there was to know about this amazing creature.
By: JethroJodhpur   Posted: 16 June 2008
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Part of: Growing Up Insane: Part 1 | Part 2 | Part 3 | Part 4 | Part 5 | Part 6 | Part 7
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