Growing Up Insane
Chapter 3
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.
(To be continued)
