Kate heard the bell ring from downstairs and dashed to the
mirror. The reflected image betrayed no flaws. The lipstick was
red and thickly applied, giving the pouting lips a playful glow.
The green eyes were right too-- the dark eyebrows thinly plucked,
the long lashes batting with plenty of body and dark promise, the
eyes themselves clear, bright and green as polished emeralds. No
eyeshadow though-- the Teacher thought that eyeshadow on Kate
gave a too-mature look and Kate was only sixteen. Cheeks were
smooth, with a complexion that was clear but for the inevitable
freckles of an Irish redhead. Delicate fingers dabbed tempting
perfume on pulse points and behind pink earlobes as the face
observed itself. Kate drew back the healthy mane of thick auburn
hair into a manageable ponytail, the practised hands smoothing
down the errant tresses into the big bowed red ribbon.

Too girlish? Kate wondered, then left the bow in place. Teacher
liked the girlish look and Kate always strove to make the Teacher
happy. It was the only way to get by from day to day. The sight
check continued as Kate inspected the skimpy garments that
clothed the small, lithe teenaged body. They weren't as sleazy
as what Kate might be made to wear, that what for sure. The
others had to wear such slutty things-- crotchless panties,
garter belts, fishnet stockings and open-nippled brassieres.

Maybe I ought to be grateful, thought Kate. What looked back in
the full-length mirror wasn't too slutty. Just a matching bra
and panty set, pretty bright blue. And they weren't silk or
anything-- just Hanes For Her. The panties were French-cut and
rested high on the hips, clinging tightly to Kate's curvy tight
midsection and butt-- simple and perfectly appropriate for a girl
of sixteen. And the bra wasn't some bullet contraption. Not
that Kate could fill that out, with an embarrassingly small set of
32A breasts. No, the bra was just a soft blue cotton thing
without wiring or teasing lifts. All it did was cover the small
pert things and give them a little definition and the smallest
shapely lift. All in all, Kate looked just like any average-to-
cute looking high school girl in her undies. No cheerleader, but
not desperate for a boyfriend either. And certainly not some
streetwalker. No, there was nothing unusual with what stared back
in the mirror, was there?

There was if the starer was really a boy, Kate thought bitterly.
The little cock thrummed in the chastity belt defiantly, if
impotently. But the crafty construction of the Teacher's
equipment refused to let the small cock out of its imprisonment.
No surprise-- it hadn't for eight months, ever since it had been
locked on. Kate sighed, then banished the taboo thoughts. The
Teacher had once explained to Kate the simple, too-obvious fact
that it didn't do any good to think such thoughts.

"These thoughts, they don't make you feel good, do they? And
your situation certainly isn't going to change, so it doesn't do
you any good, does it Kate?" Teacher was always so clear in his
explanations, everything so darn unarguable.

"Well, no sir," Kate answered simply. But a frown broke
involuntarily over Kate's lips, the kind that came even when ever
effort was being made to behave, to accept.

"Kate, your thoughts are not APPROPRIATE for a proper young lady.
You are a pretty, well spoken girl with a very pleasing attitude
most of the time. Now, I will see a happy smile on your face
now-- frowns will give you wrinkles and don't do a thing for

And so Kate smiled brightly, especially at the mention of boys.
Boys, boys, boys. Everything was about boys and being
appropriate. And there was the real desire to act appropriately
and an all-the-time fear lurking deep down of boys NOT being
attracted to Kate, Kate's smile, Kate's face, Kate's body,
everything Kate.

And now it was the Time. That was why Kate felt so nervous, so
flighty, so scared. Kate remembered a time when thinking wasn't
so hard, so difficult. The d**gs and hypnosis and physchological
training and disciplining had all f***ed changes on Kate in the
last eight months, robbing the subject of independence of thought
or even trying to think.

"Pretty girls don't think-- they just smile, Kate. Understand?"
the Teacher had told Kate, who replied with a big bright smile.
Oh yes, Kate understood. Especially after a question had been
asked. It had been a simple one-- "Why are you doing this to
me?" and the answer had been an injection. Hours later, Kate
awoke nervous and silly and without any thought other than to
NEVER, EVER to ask a question like that again.

After that, the rest seemed to come in a rush. The dressing
lessons, the make-up lessons, the manners lessons, the hygiene
training, the constant body-shaping aerobics exercising, and all
the rest. All of it was accepted without questioning of any kind
by Kate. Questions would mean big words, big thoughts that
weren't appropriate for a girl like Kate.

There were conversations, though. With the Teacher. He would
ask questions and the answers would seem to spring out of Kate's
mouth, words that came so easily that they seemed to be put there
by the Teacher himself. And once Kate had dreamed that there
were words that broke the silence of sl**ptime, words that Kate
would use when awake. But that must have been a dream indeed.

"Do you like math, Kate?" the Teacher would ask.

Kate would cast eyes down, smile foolishly. The auburn mane
would shake "no" and Kate would giggle. "Math is just for boys,

"Do you like sports, Kate?" The voice was so calm, so reassuring.
Kate always knew when the right answers were coming out.

Again, the long auburn hair shaking. "Sports are so icky, Sir!"

"But I bet sports interest you a little, doesn't it Kate?"

Kate grinned. "Football is fun-- to watch, I mean. Not to play.
Football players are so handsome." Was that answer right?

The Teacher smiled. "But you wouldn't like to play football,
would you Kate?"

A vapid giggle and a shake of that straight long lustrous auburn

"What would you like to do, Kate?" the voice asked curiously.

Kate folded the small hands, u*********sly checking the pink
polish of the three inch nails. "Well, Sir, I would like to make
myself pretty with the makeup you gave me and bake cookies for
boys, just like I learned."

The Teacher patted the auburn hair and Kate knew that the right
answer was given. "Of course you would my dear, and so you

There were more conversations like that. As the weeks went on,
Kate learned what were the right answers and what were the wrong
answers. Also learned were the things that mattered most-- like
keeping nails polished, keeping dress hems from rising too high,
to keeping hair arranged perfectly. Learning when to smile
brightly and when to listen respectfully. Discovering how to
walk like a lady in the high heels Kate was given, careful always
to walk by swinging the hips, not bending the knees. How to keep
arms up and always away from the body. Oh, it was all so very
important, the Teacher said. Otherwise, people would be so
disappointed in pretty Kate and we wouldn't want that would we?

Oh, no, Kate mused, I know I wouldn't want that! Because when
Kate didn't give the right answer, it didn't take the Teacher
long at all to take Kate over his knee. The teenager hated
waiting while he yanked up the skirt and peeled down the panties.
It seemed to take forever as he raised his hand and then let it
fall hard and fast on Kate's bare smooth butt. The number of
spanks depended on just how wrong Kate's answer was. At first,
the answers were painfully wrong. But after awhile, Kate
learned, really learned, to give the right answers.

Because you couldn't just pretend to give the right answer. The
Teacher seemed to know just what was in Kate's head (again those
voices at night drifting in and out in the dark!) and if the
right answer wasn't given without so much a second's hesitation,
gosh, Kate was soon looking at the floor as the Teacher began

Oh, but the bell was ringing, the little tinkling bell outside.
Kate had to hurry, to make sure everything was right. The First
Time was ever so important, the Teacher said! Kate nervously
checked the legs and underarms for hairs missed in shaving, the
eyebrow not perfectly straight, the uneven patch of too-dry skin.
Oh, it was maddening, all the details you needed to be aware of
when you were a teenage girl! Especially for the First Time!
And gosh, when you had been a boy to start with, it took extra
work, like the Teacher said!

Downstairs, in another part of the Teacher's gracious suburban
home, two men spoke. One, a distinguished looking man of perhaps
fifty smoked a pipe and thoughtfully listened to his guest. He
wore an expensive well-worn herringbone jacket which he
frequently investigated for more pipe tobacco. The man speaking
was handsome, thirty, and in a good mood. From his casual dress,
well-defined physique and confident demeanor, he might have
passed for a polite bouncer at a successful and upscale

"So," the younger man continued, flexing an arm, "the subject is
prepared to your satisfaction?"

The older man grinned reassuringly. He nodded, the pipe never
leaving his mouth.

"I see. Well, tell me, what should I look for in terms of
problems or deviations from what you said I should expect?" The
younger man pressed, deliberately if delicately. His numerous
negotiations in Asia had taught him the necessity of bringing up
all details before closing a deal.

The older man hooked his thumbs into the lapels of the English
herringbone. He liked to wear it in the late afternoons in the
Fall on days like this. It was a pleasure wearing a jacket like
this. Maybe that's why it seemed so appropriate to what he did.
Looking in the other man's eyes, he answered the question for the
hundredth time. He could calm all their fears by now by
patiently explanation almost by rote.

"Well," he began slowly, "Kate has been disabused of any notion
that 'she' is a boy. The chastity belt allows her to relieve
herself, but doesn't allow for arousal. This will cause her pain
as I suspect arousal will occur at some future time," he skipped
over this as a feral gleam escaped from his guests eyes, "but she
will learn to accommodate it."

"How?" demanded the guest sharply. All questions must be

"Why, through three factors, actually. First, pharmacologically,
her body chemistry has been altered. This was necessary in order
to begin the growth of her breasts. There is now more estrogen
that testosterone in the bl**d mix and she is now capable of
generating her own estrogen rather than injections. This
alteration will stymie penile arousal while igniting the
physchological factor."

"Which is?"

"Which-" he paused, clearly perturbed by being interrupted and
showing so," has been implanted through neural nets and hypno-
physchosis. These processes have supplanted many natural
impulses and behavior vis a vis the male and female gender.
Kate's value system has been rearranged so to speak, the blocks
of values previously held now in a different pattern, this having
been effected through the nets and hypno-processes."

Rather than interrupt again, the younger man shook his head in

The older man smiled. "All this means," he waved his hands as if
to wave away the confusion, "is that whereas eight months ago
Kate was a boy, with all the natural inclinations and desires of
a fifteen year old boy, he is now she, a sixteen year old girl--
with all the inhibitions and feelings of a teenage girl."

"All?" pressed the other with a wicked smile.

"Oh, yes. Well, most. It is impossible to erase all the male
identity. But that is why the Maslow's Hierarchy of Needs is
such an important concept for you to understand in this regard.
You're familiar with it?"

The man scratched his head. "I can tell you the price of
microchips in Singapore, but I confess, it has been awhile since
I was back here at Elgin, sir. I don't recall what it is, but it
sounds familiar."

The older man's eyes rolled in disappointment. "We take such
care in devising this cirriculim for you boys, but--ah, well!
Maslow was a clinical physchologist who discovered that within
each of us is a series of needs which we need to satisfy on our
way to self-actualization, a term which basically means complete
satisfaction with our existence.

The basics are, as you would expect, food, shelter, clothing, and
the like. Next comes what we would think of as physical
pleasure, then wealth and power and so forth. Well, in Kate's
mind we have displaced the importance of female values with that
of male values. She now values female values as basic survival
values but is attracted toward male attributes in order to self-
actualize. Understand now?"

The quizzical look on the younger man's face was the silent reply.

"Very simple, you see. Kate finds absolutely none of the mystery
she used to find in things she has been trained to think are
female-- things like beauty, grace, the desire to please, the
urge to attract. Those things are lower values, essentially the
price she pays for being what she is now-- the price of

Comprehension dawned quickly on the business executive's face and
he nodded for the academic to continue.

"What she secretly longs for and values are what she has been
taught are male attributes-- strength, confidence and sureness
of purpose, even selfishness."

"So she what you're saying, if I get it, is that Kate isn't some
prima donna beauty queen now, right?"

"Oh, far from it! She's attractive, to be sure, but she doesn't
perceive her beauty to have any value in isolation from a male.
None of what she has to offer has any value without a male to
please with her charms."

"And there isn't any boy left in her?"

"There will be a marginal amount, but that is where the third
factor comes into play."

The man gestured with his finger. "I was going to ask you about
the third. Aren't the first two sufficient?"

The Headmaster's eyes widened. "I haven't educated and trained
juveniles this long without discovering that old fashioned
discipline works as many wonders as modern physchology and

"Very good, I see," replied the guest. "Well, that takes care of
the subject's physical, emotional and mental well-being. What
about the legal implications of all this?"

The Headmaster handed him a sheaf of papers in a manila folder,
which his guest slowly paged through as the older man explained.

"The subject is a scholarship student whom the Academy took on as
part of a program with the local authorities. The subject has no
known f****y, had been hosted by a number of foster homes, and
was dangerously close to being remanded to a county facility for
juvenile delinquents, when accepted here. As a result, the
subject was placed under the legal auspices of the Academy. The
subject was delighted to be here." The older man smiled archly.
"No surprise there, of course. Were you aware that this is one
of the most exclusive boy's preparatory schools in the nation?
We can count seven presidents who prepped here and our scholastic
achievements are too numerous to mention. Why our SAT average--"

The younger man cut him off. "Sir, with all due respect, you
forget I prepped here. I am well aware of the Academy's well-
deserved reputation. Please, please just continue," he added

The older man shrugged. One of the problems of dealing with
youngsters all day was that you could easily forget how to deal
with adults! He chuckled. "Of course, of course. My apologies!
Anyway, it was reported back to the proper county offices and
social workers that the subject was not fitting in well, that in
deed, was causing difficulties for our other students.
Naturally, the social worker who came to investigate the
subject's disappearance was quite disgusted. When given the
chance to get a first-class education all on scholarship, without
the county having to spend a dime, the fact the subject ran
away was enough to put the whole program into question."

The younger man was taken aback. "Then you've canceled the
program to take these students on scholarship?"

"Not at all," the older man reassured him. "I reluctantly agreed
to continue the program, which delighted the social worker to no
end. Do you know that the county spends over thirty thousand
dollars a year to-- ah, but I am digressing. Back to the point.
Yes, the program continues, but now only under the condition that
the Academy not be plagued by constant visits from the Social
Services Office or regular reports. Elgin Academy graciously
extended the program to accept these hardship students under the
condition that the only nuisance the county be allowed to ask for
is a copy of the subject's diploma upon graduation."

The younger man chuckled. "Well, how very convenient,
Headmaster. And how very profitable!"

The older man smiled in shared confidence. "Isn't it, though?
And with regard to that, I must thank you for your kind
contribution." A grateful hand was offered, which the executive

"Say, Headmaster, could you turn on the monitor in Kate's room
like you did the last time I was here?" There was a slight jump
in his deep voice as he made the request. Like a k** taking a
peek at a Christmas present, he thought in guilty excitement.

The prep school headmaster nodded indulgently. "By all means.
Let us see what the dear is up to." He pulled a key from his
jacket pocket and unlocked the door of the wallmounted wood
cabinet behind him. The opened door revealed a dark monitor.
the academic punched in a code on the monitor console and the
monitor expanded into a technicolor square.

"She's so damn cute!" The businessman looked at the small figure
on the screen with rapt attention. "And she's got a figure now--
that was just starting the last time I was here!"

"Yes, Kate is filling out. As I've said before, she won't ever
be a Dolly Parton. In fact, what she's got is probably all
she'll ever have, though I haven't had the heart to break it to
her. Funny, that. At first, she required quite a bit of coaxing
to get her to wear her training bra. She was so-- obstreperous.
'Why do I have to wear a bra?', 'I don't like having breasts',
'I'm really a boy' and all the rest. So ridiculous. But in
time, she's accepted them, more than that I would say! She's
been measuring herself every day, becoming ecstatic if she grew a
micrometer! Always reading articles in her copies of Sassy and
s*******n about breast size and so forth. Look at her-- even
now, she's obsessed with them!"

The screen gave a clear view of what the Headmaster was referring
to. Kate cupped her small breasts, lifting them and looking at
herself in the mirror. Then she dropped her hands and thrust her
chest out like a cadet, an unsatisfied look on her face.

"So damn cute!" repeated the younger man roughly. Then,
recovering himself a bit, turned to the Headmaster. "Sort of
looks like Jodie Foster, don't you think?" He asked the question
self-consciously, almost self-congratulatory.

"Of course she does, Edgar. After all, that's what you told me
you wanted in a niece-- a thin redhead with a pale complexion,
sharp pretty features, slim hips, small breasts-- all you asked
for. I believe you mentioned Jodie Foster as Kate's physical
model, did you not?"

"Yeah, well I think you're right." The younger man's eyes
narrowed. "Quite a babe that Jodie Foster. Anyway, what has she
been told again?"

"That her uncle is coming for her today and he wants to see how
much his niece has developed. That the last time you set eyes on
her, she was very, very young. That her long-lost uncle is a
very successful businessman who works in Asia. And that if she
is 'mature' enough, you'll take her with you when you go back to

The exec's eyes were fixed on the feminine figure primping on the
monitor. "It'll be wonderful to take her over there. The life
of an expatriate is a lonely one and as I mentioned, the AIDS
epidemic is getting quite virulent. It was obvious to me some
eight months ago that the usual company with which I indulged
myself was just getting to dangerous. Risky. Still," his brow
creased, "to be honest, even now I wonder if a real girl wasn't
the way to go."

Headmaster shook his head. "Too expensive, even for you, Edgar.
Besides, I'm sure she please you-- except for the genital switch,
there's not a lot of difference now. And girls are far more
difficult to train. Besides this way you're helping your alma
mater. Your 'contribution' pays off in two ways-- it is tax-
deductible plus you enjoy the benefit of a pretty, well-bred
young companion. How else can you both save yourself a great
deal of money, make our library expansion possible and gain such
a delightful traveling partner?" He pointed at the monitor with
his pipe.

Edgar looked sheepish. "I'm so pleased to help the Academy. The
library needed the new wing, Headmaster. I'm honored to be a
part of the continuing success of the school. And delighted to be
part of your special extracurricular program, sir."

The academic pulled on his herringbone lapels and smiled broadly.
"Anything for an alum of old Elgin! You know this program has
done wonders for our fundraising. It is because of such
supporters like you that our special education program works so
well. Do you remember your classmate John Worthington?"

The younger man nodded. "Good old Jack! How is he? I heard
he's the youngest ambassador ever appointed to France!"

"Oh yes, we're quite proud of him at Elgin, as we are of you-- I
saw you on the cover of BusinessWeek touting you as the country's
hottest portfolio manager in the Far East. Anyway, John is going
to France and along with his wife and young son, he is bringing
along a nanny, a certain young lady of s*******n named Samantha."

The guest tried to trap a chuckle with his hand. "You're not
suggesting old Jack--"

The Headmaster smiled in amusement. "Let's just say Samantha, a
lovely brown-haired thing, used to be a young street ruffian
named Sammy or something! Too bad we can't 'help' more of our
former students this way, the school needs so much work."

"Why not simply ask more alums if they'd be interested?"

The Headmaster shook his head. "Believe it or not Edgar, most
tastes run to the rather ordinary. It takes a very special
person to appreciate a delicacy like Katie or Samantha. And the
gymnasium does need so much repair. I think our basketball team
can have such a superlative season. Ah, but funds are lacking!"

Edgar shrugged. "How much would you need to do a complete

The older man scratched his graying head. "Perhaps two million--
at least one."

Edgar smiled widely. "If Katie is half of what you promise
she'll be, I think we can find that money, Headmaster!"

"But Edgar, are you offering to donate--???"

"Please sir, I'm successful, but not that successful. However I
have an idea. I'll call you next year-- by that time I'll know
if it's feasible." On that mysterious note, the guest turned
intently on the older man. "I'd like to see what I have bought
now, if that's all right."

The Headmaster nodded and pushed a button at his desk. Upstairs
Kate heard the bell again, loud and insistent. "To let her know
her 'uncle' is coming up to see her," the Headmaster explained.

As the two men approached the small locked door, the Headmaster
pressed some small items into the other man's hands. He put his
hand on the other man's arm, the powerful biceps bulging under
the casual sports jacket.

"I'll let you two get acquainted. She's dressed precisely as you
wished-- a pleasant deviation from the usual norm, I must say.
Take as long as you like of course, the she can dress. Her bags
are packed and you can leave with her any time you like. If you
have any problems, contact me at once." The headmaster gave him
an understanding smile. "The initial training can be sticky, but
she is waiting for you. And as much as she is afraid of you--
and will probably continue to be-- she is just as secretly
excited about being your 'niece' and everything that goes with
it. Good luck old man, and see you at Homecoming next year."
With that, the older man walked down the stairs.

The younger man looked at the items in his palm. There were two.
One was a square plastic package that was labeled "Stud Condom--
Ribbed For Extra Pleasure". The other was a tiny key with a
small tab. It read simply "Kate." He placed the key carefully
on his keychain, then opened the door.

Kate stood facing him, head bowed but green eyes looking
anxiously at him. Her hands and arms nervously covered her
chest, then with a f***ed jitter, dropped to her side, exposing
her blue cotton brassiered chest. She chewed her lower lip, then
with a supreme effort, smiled sweetly for her guest.

"Hello, Uncle Edgar. I'm so glad to see you." The words were
offered like a gift that the giver knew, just knew, wasn't good
enough, but had to try anyway.

Uncle Edgar closed the door behind him and gestured for Kate to
approach him. With head bowed, she carefully walked over to
present herself to him, her hips swaying slightly, her hands
raised and away from her hips.

"Aren't you going to give your Uncle a big kiss when I've come
from so very far away to see my pretty niece?" he chided her.

She smiled brightly at the compliment then and hoped, just hoped
that she would never ever make her new uncle mad. He seemed so
handsome and so nice. She threw her thin arms up and around his
broad shoulders as best she could (he was so tall!) and, closing
her eyes as taught, offered the red painted pouting lips up for
him to take as he wished. And even as she had hoped it would all
be nice for the First Time she met HIM, she felt his hands
roughly reach down and squeeze her butt hard, then cup her little
breasts. And she was afraid, afraid even though deep in her
beating heart she felt a new warm and dark thrill flowering.
This wouldn't be the kind of First Time she had expected at all,
as he pressed her down to her knees. She thought, this is a
different kind of First Time, even as he placed her hands on his
thighs and f***ed the pink nailed fingers around his trouser
zipper. And years later, even after her Uncle Edgar had taught
her so much more, when she thought back to the First Time, Kate
would shiver in terror and delight.

71% (7/3)
Categories: First TimeShemales
Posted by alexwd0
3 years ago    Views: 1,949
Comments (1)
Reply for:
Reply text
Please login or register to post comments.
3 years ago