Growing Up Insane
Chapter 05
In this new capacity as a prostitute expected to service both sexes on a
regular basis, singularly or as couples, Tabitha had a great deal of difficulty
with the distaff side. Men were easy since Tabitha thought of herself as being
female, and the great majority of her male customers accepted her as such
despite her additional appendages. It was a very rare male customer who wanted
to assume the submissive role in the relationship. All these rules went by the
board when the client was female.
Just as many wanted to submit to Tabitha as dominate the transsexual.
Poor Tabitha never knew in advance what type of sex act would be required by her
female customers. In many cases her female clients were equally unsure about
their needs or desires and how they could be satisfied. Worse still were the
couples that came for Tabitha's unique services.
For some odd reason the female would be either extremely submissive or
dominant; there never seemed to be any middle ground with the women. Since the
young transsexual had limited experience in dealing with women in any capacity,
the extremes she was now exposed to left her bewildered, which often caused
trouble for her. It was very bad when Tabitha discovered that the female member
was the dominant one. It was a nightmare when both were dominant. As I had
learned over the years as a sex professional, the key to success was to
understand the needs and status of one's clients and act accordingly. The
successful sex worker has to be a student of human nature, quick to assume any
role as the situation dictates. Tabitha was woefully deficient in this critical
skill, doubly dangerous when one considered her sexual status.
As bad as the first week as a prostitute was, things got a great deal
worse once Tabitha met the Wendalls. These two were both dominants, yet managed
to keep their marriage together by taking out their aggression on more
submissive types that they either cultivated socially or hired. Naturally
Tabitha fell into the latter category, and the initial encounter with the
Wendalls was utterly traumatic. The novice prostitute was instructed to go to
the Wendall home and allow them complete freedom to do anything they wished to
do as long as it did not result in permanent physical damage. Tabitha to this
day is still unable to fully describe what transpired during that long night.
However what I was told was sufficient to form an outline of what the
transsexual endured during that first visit to their home.
They made Tabitha strip to the skin and masturbate until that nine inch
plus piece of meat was stiff as it could be. Claudia Wendall then produced a
vicious looking cock ring made from metal. It was modeled after a hose clamp,
but the intricate engraving and the materials used indicated that it had been
formed by a skilled artisan rather than pulled off the shelf of the local
hardware store. While she tightened the cock ring, running her long fingernails
up and down the length of the transsexual's straining penis, her husband, Mark,
busied himself by restraining Tabitha with handcuffs. He then watched with a
sardonic smile as his wife turned the tiny key that forced the diameter of the
ring to be reduced, bringing a gasp of pain from the youthful prostitute. "One
more turn should do it for the moment" she said as she turned the key while
Tabitha grunted and tears began coursing down those perfect cheekbones.
Tabitha was placed in a prone position on the large bed. They quickly
attached Tabitha's ankles to a spreader bar, forcing the trannie's legs wide
apart, making it a simple matter to have easy access to Tabitha's puckered
asshole, swollen cock and that big basket of balls located below the cruel metal
noose that was disappearing into the purplish skin. Tabitha was now secured in
such a manner that the youth's head was almost hanging over the lower portion of
the bed. It was there that Mark took his place, grabbing the prostitute's hair
to move it into the proper attitude so that Mark could begin face fucking the
transsexual. Claudia took up a position that allowed her to straddle Tabitha.
The trannie would have been horrified if what was being strapped around
Claudia's hips had come into view.
The initial onslaught from the couple caused Tabitha to suffer a sensory
overload as well as an identity crisis. Although the Wendalls were vicious
dominants, I could not bring myself to believe that they were so intelligent
that they would deliberately create a situation that would cause incredible
emotional distress to the young transsexual. I really believe they looked upon
this gorgeous creature as just another piece of fuckmeat to enjoy and cast
aside. However they were quick to expolit the situation once they realized that
they had been its cause. From then on the session turned into a nightmare for
Tabitha.
When Mark offered his semi-hard cock to Tabitha, the transsexual
attacked it with gusto, excited about the prospect of feeling this rapidly
growing slab of meat burrowing to the depths, stretching her colon in ways that
had not yet been experienced. Mark on the other hand was merely interested in
causing the young prostitute as much discomfort as he possibly could. He worked
his thick prong deeper and deeper into the trannie's throat, cutting off the air
and pounding away at the senstive lining guarding Tabitha's gullet. Meanwhile
Claudia had taken up a position above the youth and was working one of her sharp
nailed fingers into Tabitha's asshole, searching for that magic button that all
men had.
Despite being choked and finger fucked Tabitha was doing fine; Mark's
cock was doing what it should as far as the prostitute was concerned. Even that
long finger working on the youth's prostate was acceptable, it only made that
straining penis harder and more painful which was the price one paid for having
too much sexual equipment. It would be so much better when that large piece of
male meat attached to the trannie's shapely female body was gone. Then Tabitha's
world was turned upside down! What was that entering inch by slow painful inch?
It was hard and unyielding, and felt almost as if it belonged to a male, but how
could that be? The only male was in front of Tabitha, attempting to make his
entire cock disappear down the young whore's throat before there was no more air
left to fill its heaving lungs.
For longer than Tabitha could believe, these two took turns humiliating
and hurting the young transsexual. First Mark would choke fuck Tabitha until she
passed out. All the time that was going on, Claudia would be widening and
deepening her victim's anal passageway with her trusty dildo. Then the two would
switch and Tabitha's mouth would be filled with the dildo and whatever it had
picked up from her colon while Mark's stiff prong plunged and played deep within
his prey's bowels.
When the couple tired of that activity, they opted to see if they could
manage a double anal assault on the youthful prostitute. To accomplish this they
turned Tabitha over onto her back and raised her legs that were held wide by the
spreader bar. It took a number of failures before Mark managed to maneuver
himself under Tabitha at just the right angle to embed his hard cock into the
trannie's asshole. Then it was his wife's turn to position herself and then her
dildo so that she could jam it inch by slow inch into the space available.
Tabitha had never been stretched to this point before and feared that something,
possibly her sphincter, would give way causing agonizing and even permanent
damage. Somehow Tabitha's body stayed whole and after acknowledging that they
had indeed doubled fucked the trannie's asshole, the Wendall's declared victory
and decided to take a breather.
A breather for them still meant a great strain on Tabitha. Mark amused
himself by stroking Tabitha's swollen cock and squeezing the prostitute's
bloated balls while Claudia sat on Tabitha's face and had her lick her
perfexctly smooth pubic mound, guiding her from one sweet spot to the next with
the firm grip she had on Tabitha's longish hair. Next Claudia swiveled round and
presented her firm bottom for the transsexual to kiss and lick, moving her
tongue closer and closer to that winking brown eye located between Claudia's
smooth firm cheeks. She bent forward so she could use her long nails to rake the
youth's throbbing cock from its base to tip. "I'll bet you'd love to shoot a
nice big load of man juice all over your belly wouldn't you?" Claudia teased the
frantic trannie. Darling why don't you fuck this tramp up the ass some more
while I try to make the poor dear give me a demonstration of just how badly it
wants to come."
The couple exchanged knowing grins as Mark rolled a thick walled condom
onto his cock after Tabitha had sucked it until it was rock hard. Her husband
then slathered his sheathed member with a special ointment that would make
Tabitha believe that her rectal area as well as her colon had caught fire. He
began to work his thick length of well protected flesh into his victim's well
stretched anus. It didn't take long for the first sensation to get the
transsexual's attention. Mark smiled an evil smile and shifted his hips so he
could drive another few inches of his hard weapon into the prostitute's rectum.
Tabitha began to screech as the ointment coated more and more of her
tender tunnel, burning away the mucus membrane that offered the only protection
for the sensitive tube. Now it was Claudia's turn to shift herself so that her
round ass stiffled Tabitha's howling. "Hush you little trollop, do you want to
wake the neighbors? If you do, I'll invite them over to help us ruin that
sloppy, loose asshole of yours." Her husband smirked and wedged still more of
his meat into Tabitha's flaming asshole. Meanwhile Claudia was bouncing her body
up and down on Tabitha's face, driving the air from her lungs with every
landing.
Mark continued to saw away inside Tabitha's burning, seething asshole
while his wife once again centered her anus to the trannie's mouth for more
attention. So while Tabitha felt as if she were in the process of dying, the
husband and wife leaned towards each other and exchanged a passionate kiss. This
finally triggered off Mark and he spurted his cum into the condom and filled it
to its limit and a bit beyond. Then Claudia carefully peeled the slimy sheath
from her husband's angry, hard cock and then proceeded to feed it to Tabitha, a
drop or so at a time. Tabitha was eager to swallow every drop of Mark's cum,
that was her purpose as far as she was concerned. Claudia on the other hand
wanted to make this activity as humiliating as possible in the interest of
further damaging the transsexual's fragile psyche.
She took to rubbing her husband's semen onto her breasts and making
Tabitha strain to lick it from them. She thought this was great fun and so she
applied more of his cum to her flat stomach and laughed uproariously as Tabitha
stretched her neck to its limit and stuck her tongue out as far as she could,
and still was unable to reach her goal. Claudia thought this was great fun and
continued to tease the trannie until every last drop had been licked up and
swallowed greedily by Tabitha. Claudia even went so far as to turn the condom
inside out and make Tabitha take it into her mouth to get the last traces from
it, even though she risked burning the inside of her mouth and her tongue from
making inadvertent contact with the ointment that still remained.
They took another break to discuss what to do to their helpless visitor
before sending her packing. "I think it only fair that our helpmate enjoy a nice
complete orgasm as well, don't you think?" Mark laughed and reminded his wife
that to the best of his knowledge she had yet to enjoy her own orgasm. Claudia
grinned and reached into the nightstand by their bed and withdrew a sleek
metallic looking vibrator. She held it up for Mark and Tabitha to see.
"Mark, you are so correct, and I thank you for being concerned about my
pleasure as well as your own. That's why we have such a good relationship. I was
planning on letting Tabitha use this to bring me off." Then she looked over to
the trannie and smiled coldly.
"I want you to hold this in your teeth and use it to fuck me. Be sure
that you make every stroke slow and deep. You shall be punished if you don't get
me off in a reasonable length of time. I don't think you will want to suffer
what will be a most severe punishment if you fail to satisfy my wishes."
It took Tabitha almost an hour to finally bring Claudia Wendall to a
rather satisfying orgasm. The poor dear's neck felt as if it were supporting a
thousand pound load and her shoulders ached from the stress of supporting her
neck and head as she held the buzzing tool in her teeth and slowly pushed it
deep into Caudia's ripe cunt and then strained to pull it free from her
suctioning grip. As if this wasn't bad enough, Mark worked his middle finger
into Tabitha's butthole and located the transsexual's prostate. For the rest of
the lengthy process that at long last yielded an orgasm for his wife, he
tormented Tabitha by constantly stimulating the sensitive lump of nerve endings.
Mark was surprised to discover the ring of pre-cum that had formed beneath
Tabitha's body,and when he pointed it out to his wife she was quick to command
poor Tabitha to get busy and suck the pre-cum from their sheets to avoid leaving
some kind of a stain.
The grand finale involved Caludia working the silver bullet vibrator in
and out of Tabitha's twitching asshole while Mark teased the trannie's swollen
and very sore cock with short, powerful strokes that made his wife's eyes
sparkle as she watched the procedure and enjoyed the moaning that seemed to
continuously come fromTabitha. The cock ring had done an excellent job of
frustrating any ejaculation that they might have tried to make Tabitha produce.
Now it was still the major obstacle to any hope of the trannie delivering
anything resembling an ejaculation. Claudia finally relented, more out of
boredom than consideration for the trannie's discomfort, and allowed the cock
ring to be opened. Tabitha 's eyes rolled back into her head and she passed out
from the pain that resulted once blood circulation was restored to her sex
organ. That evening there was no ejaculation produced by Tabitha. The poor thing
was sent home in pain, utterly humiliated by her clients.
( To be continued)
