Date: Thu, 31 Dec 2015 14:18:40 +1030
From: Amanda Stern <astern50@gmail.com>
Subject: My New Career (Part 2) - TG

Welcome to the second chapter of this kinky tale of a career choice gone
wrong. Please email me with any comments or reactions, and do think about
donating to help support this wonderful site.

===================

MY NEW CAREER - PART 2

Whistling tunelessly, I put down the pen and inspected my handiwork. Not
great, but not bad either. In the circumstances, it was the best I could
do. It wouldn't fool anyone who looked too closely, but hopefully I could
avoid that kind of scrutiny. And if I did get rumbled, well - what was the
worse that could happen? With a shrug of my shoulders i turned to the next
item on my list. The choice of colours was pretty limited, but then so was
my ability to carry them off. With a sigh, I picked up the Russian Red
lipstick and began to apply it to my  puckered lips ...

It had started the day of the interview. Kristen Everett, one of the
principals of the college that I had hoped would employ me as a teacher,
had not only told me I was to be a student there instead, but insisted I
would have to wear a uniform. A uniform involving stockings and heels! And
had I heard right? Had she just called me ... Katy???

As I stared at her in consternation, her brother Gordon patted her on the
arm and headed for the door of the office. Pausing in the doorway, he
announced brightly: "Well, I'll leave you girls to it then. I do have some
lessons to supervise." With a twinkle in his eyes, he delivered his parting
comment to me: "I'll look forward to seeing you later ... Miss Riley."

I watched the door close behind him and then swung back to face Kristen.
Blushing furiously, my mouth moved soundlessly for a moment before I could
find the words for which I was searching. "What did he mean ... and how am
I supposed to wear those ... those things? I'm not -"

The finger she put to her lips cut me off in mid-sentence. She looked at me
steadily for a moment. When she spoke, her tone was businesslike.

"You will at all times address me as ma'am. My bother is sir. The same for
all the staff here. You will await instructions and not ask questions
unless absolutely necessary. Is that clear?"

I opened my mouth to protest, but closed it again as Kristen lifted
her eyebrows and with a slight incline of her head directed my attention to
the computer screen. It was still cycling through photos of the sexual
encounter I'd had in this very room just a few minutes ago. Photos that
iwould be very hard for me to explain, if they got into the wrong hands -
or any hands, for that matter. Photos that, together with the contract I
had just signed, would ensure I did exactly what I was told.

In the circumstances there was only one answer to give. "Yes ma'am", I
responded in a quiet, dispirited tone.

"Excellent", she said, rubbing her hands together. "We can get to work
then. You can start by taking your clothes off."

I gave her a blank stare. My head was clearer now, but I simply couldn't
process the information. (It said something for my state of mind at this
point that it was only later that I realised the pastries I had eaten must
have been drugged - though how much my behaviour had been modified remained
worryingly unclear.)

The principal responded by picking up the ruler I had discarded and tapping
it meaningfully against the palm of one hand. "What part of 'take you
clothes off' don't you understand, Katy? Do it now!"

The whiplash emphasis on the last word was enough to jar me into action. I
hastily peeled off my jacket and shirt, laying them down on the couch. My
shoes, socks and trousers quickly followed. As I stripped off I wondered
about the name she had now twice used in speaking to me. Why did I suddenly
have a girl's name? And what was familiar about that name anyway?

Soon enough only my boxers remained. I looked imploringly at Kristen - no,
I must start thinking of her as Miss Everett. Whatever her name, her gaze
was implacable.

"Did I tell you take your outer clothes off, or everything bar your
underwear?" she inquired, icily. "No, I did not."

With a sigh I pulled down my last item of clothing , stepped out of it and
stood before her, my hands awkwardly cupped over my genitals. She snorted
in derision. "There's nothing there I haven't seen"' she commented drily.
"Indeed I saw it just a few minutes ago in the mouth of that lovely young
man. Put your hands behind your back."

This time I obeyed the peremptory command and stood there awkwardly, all
too aware of my nakedness and shivering despite the warmth in the office.
Miss Everett stood in front of me, and without breaking eye contact reached
down to lightly fondle my cock. It was all I could do not to cry out. As it
was, my member stiffened noticeably under her touch.

"Hmmm, what a big clitty you have, Katy. We'll have to see what we can do
about that ..." As I pondered what on earth that last remark could mean, my
cock grew harder still.

Still lightly stroking me, Miss Everett reached across to press the
same button on the desk her brother had recently used. "You can come in now
Grace", she said.

As the door opened to admit the pretty receptionist I'd already met, Miss
Everett stepped away from me, leaving my semi-elect cock fully exposed.
Grace seemed unsurprised to find a naked man in the principals' office. She
did not even spare me a glance, looking instead at her employer for
instructions. But if I thought I'd been embarrassed before, it wa nothing
to the flush that now spread through my body - an effect that only deepened
at Miss Everett's next words.

Motioning to the receptionist to a nearby straight-backed chair, she looked
at me thoughtfully, then said: "in a minute, Grace will take you to get
prepped. But before she does that, I think you need a demonstration of what
happens when you don't do what you're told."

She gestured towards the young woman, who was now sitting upright, her
skirt riding up to reveal the stocking-tops I'd glimpsed earlier. "I want
you over her lap, face down, bottom up. Now."

Despite my shock at her command, I was quick this time to obey ... though
Miss Everett insisted on moving me around to find the right position, with
the result that my cock kept grazing against Grace's nylon-clad thighs,
something which did nothing to lessen my arousal.

When she was satisfied, the older woman instructed the receptionist: "Five
strokes on each cheek please. And since I'm feeling generous today, your
hand will suffice, dear."

I couldn't ever recall being spanked before - and it was not an experience
I was eager to repeat, either. No light taps for me, just heavy-handed
blows that first smarted and then really hurt. There was nothing in the
least bit exciting about it and even Grace's application of the cooling
cream I'd earlier used on Jason did noting to restore the erection that had
collapsed after the first resounding slap.

When Grace was finished with the cream, Miss Everett went to the bag
she'd showed me earlier, pulled out a long, slender gown made of
a diaphanous black fabric and told me to put it on. It was pretty
see-through, but at least gave me some semblance of decency as I followed
the receptionist to another part of the College's underground facility.
Mercifully, we passed only a few groups of people along the way, none of
whom paid any obvious attention to me.

The next three hours passed in a blur that was alternately painful and
embarrassing - or indeed often both. I was put into the care of a sweet
young redhead called Lily and a rather androgynous young man named Daniel.
They began by using a combination of creams and wax to strip me of all my
bodily hair - genitals very much included, to my considerable discomfort. I
was bathed in sweet smelling oils that left my skin smooth and finely
scented and given the first of what turned out to be several sets of
products, accompanied by detailed written instructions on how and when to
apply them.

Next, they turned to the only substantial hair I had left. My eyebrows were
trimmed and tidied and my dark brown, shoulder length hair was shampooed,
conditioned and repeatedly brushed, until it had a lustrous sheen I'd never
previously seen. It was then tied into two bunches, one on each side of my
head, with simple pink scrunchies to hold the strands in place.

Last, an extensive collection of makeup was applied to my face and neck.
The process took a considerable time, with much careful explanation from
Daniel and Lily about what to use, how to apply it and in what order.
Again, I was given both products and instructions to take away - the clear
inference being that I would be expected to do this myself in the future.
After the initial layers of foundation were put on, I was required to keep
my eyes closed throughout the process - except when the eyeliner was
applied, for which I had to look at the ceiling and do my best not to
blink. By the time I was allowed to open them again, I was no longer in
front of a mirror, so at this point I had no idea how I looked. But Lily
and Daniel clearly seemed satisfied with their efforts.

Throughout this process - or at least for the first hour or so - I tried to
get my two beauticians (if that's what they were) to tell me what was going
on. But while they were perfectly happy to chat about fashion, celebrities
or the latest internet memes , and treated me as gently as the process
allowed, they simply refused to answer any questions about either Ceder
College or what was to happen to me.

Eventually, Lily cut off yet another query with a finger to her lips,
pointed around the room, then mimed someone listening on headphones. I got
the message - that we were somehow under surveillance, though I could see
no cameras or microphones anywhere. At that point I stopped asking
questions and started thinking instead, while still making small talk from
time to time.

Not that the thinking got me anywhere. It was plain that I was being
forcibly feminised, though to what end I simply could not imagine. I would
just have to wait and see what happened. Would I even be allowed to go
home, I wondered, or would I have to stay at some dormitory here at the
College? I had no close family or friends who would be likely to miss me if
I didn't go back to my apartment ... though my landlord might come looking
if the rent didn't get paid, especially as I was already a couple of weeks
behind.

The one mystery I thought I might have solved concerned Miss Everett's use
of the name Katy. A chance remark by Daniel reminded me that one of the
questions on the College's application form concerned the identity of the
woman I'd most like to spend time with. After toying with a number of
worthy but not entirely honest options, I'd eventually decided to come
clean and nominate Katy Perry. It was not so much that I loved her music -
though it was enjoyable enough - as the fact that she figured so
prominently in my fantasies.

Was it coincidence then that the name of the woman I'd most like to know
and hang out with (or, okay, sleep with) was the very name Miss Everett was
now calling me? I didn't think so. Which presumably meant that if I'd
nominated my favourite actress instead, I'd now be having to answer to
Jewel or Morena ...

At any event, it was a very different Martin Riley (no way was I going to
think of myself as Katy!) that was returned  to the principals' office,
some time around lunchtime - fully shaven, far sweeter-smelling, made up
and with my hair in unfamiliar bunches. I found a plate of sandwiches and a
jug of orange juice waiting for me, but after a suspicious look decided
that I shouldn't risk them.

After a short wait, Miss Everett entered. She gave me a searching look,
then smiled and shook her head. "Damn, those two are good. I know I
shouldn't be surprised, but I always am ..."

Noticing the sandwiches, she picked one up, bit into it and then held the
uneaten part up to me. "Not hungry?", she asked, a ghost of a smile playing
on her lips. "Too bad, they're really nice you know."

Returning to the bag of clothes that I'd seen her with before, she fished
out several items and dropped them on the couch next to me. "Okay, time to
get you into your first costume. Take the gown off, and then start with the
stockings."

With only the slightest hesitation - I had already learnt not to question
her commands - I slipped out of the gown and sat down on the couch, trying
my best to ignore my nakedness. I rummaged through the pile and found two
wispy black nylon stockings. As I'd seen women do in films or videos, I
tried to gather the first stocking from the inside, carefully inserted one
foot into the bottom, then began to peel it up my leg. It took a lot of
tugging and smoothing - the material was evidently quite resilient, because
it didn't run - but eventually I had it all the way up to the top of my
thigh, where the elasticated top held it in place.

After the other stocking was secured, I looked at Miss Everett for
guidance. Wordlessly, she handed me a pair of black, satin panties. They
had a curious inside pocket which had me puzzled for a moment, until the
principal showed me how to tuck my cock into it. A small drawstring at the
bottom, when pulled tight and tied up, ensured that my member was pulled
back underneath me. There was still a slight bulge, and it wasn't exactly
comfortable, but at least if I got excited my cock would not jut out like
tent pole.

"Now Katy", said Miss Everett, holding up the shoes I had glimpsed earlier
in the day, "here is the most important part of your outfit." The shoes
were made of black leather, with fully enclosed toes, elegant heels and
fairly chunky ankle straps. "They're only three-inch heels, but we'll get
you into higher ones when you've learnt to cope with these. Come on then,
let's see them on you."

I manoeuvred my feet into one shoe, then the other. They were a snug
fit. Miss Everett showed me how the ankle straps fastened, including a
special clasp that made a distinct click as it was engaged.

As I stood up and tried to get used to the novel and awkward angle of my
feet, wobbling not a little, Miss Everett laid a hand on my arm to steady
me, then delivered yet another shock in what was already a day of unwelcome
surprises.

"Now listen carefully Katy, you need to understand that these are very
special shoes - and I don't mean those lovely heels that you're doing your
best to fall off. Those straps contain some very clever technology. Once
they are fastened, they are locked in place. Unless you have a key - and
we're not giving you one - you won't be able to take them off until eleven
o'clock tonight, when the clasps will automatically undo. You could cut
through the straps - but aside from being a lot tougher than they look, a
biometric sensor will let us know if you're no longer wearing the shoes.
And then ... well those lovely photos of you and Jason will be all over the
Internet. Understand?"

Even with my heightened sense of anxiety - or perhaps because of it - it
took me a few seconds  to take in what she'd just told me. I exhaled and
then answered "Yes ma'am. You mean ..."

"I mean", she said, her voice still level, "that you're wearing those shoes
for the rest of the day. When we've finished with you, you'll go home - in
those shoes. And you'll stay in those shoes until at least eleven tonight."
She smiled thinly. "And in the morning, you'll have until eight o'clock to
put them back on. If you don't do that, we'll know. As we'll also know if
you try to make your way here in any type of footwear other than your new
shoes. We will swop them from time to time, but until we say otherwise, you
are going everywhere in high heels. Got it, Katy?"

The emphasis on the name was just that last twist of the knife. As my
expression must have told her, I was already starting to run through the
implications of what she'd just said - and not liking them one little bit.
But there was only one thing to say."Yes Miss Everett ... I mean, ma'am."

Her smile broadened, as she picked up the remaining items of clothing. "All
right then, let's get the rest of this on you."

"This" turned out to be a grey, pleated skirt which, although short, seemed
long enough to sit below my stocking tops, together with a white blouse,
blue blazer and striped blue tie. The outfit clearly matched the one I had
seen on Jason earlier.. It was rather less, well, sexy, or slutty, than I
had feared. Aside perhaps from the height of the heels, it was the kind of
uniform you might routinely expect to see being worn at some of the more
affluent (or pretentious) high schools. Which of course would figure ... if
I was expected to wear it to go home in. On the train, no less.

Doing my best to suppress this horrible thought, I tottered behind Miss
Everett as she led me out of the office, down a corridor and into a
bathroom, where a full-length mirror at last allowed me to see what had
been done to me.

I stared. For the first time in hours, the knot of tension in my stomach
relaxed, just a little. For one thing, I was unrecognisable. Looking as I
did, it was hard to imagine anyone twigging my identity - certainly not
without close inspection. For another, I was almost ... pretty. The makeup
was not the pancaked caricature of the drag queen, but a subtle use of
tones and textures to suggest femininity. Minus the telltale stubble, and
with my cheekbones and jawline altered, I could almost pass as the young
woman that my hair and clothing suggested.

Of course I could see right away that I was holding myself all wrong, and
as soon as I tried to move the illusion was quickly lost. But with a bit of
practice ...

I caught Miss Everett's eye in the mirror. She gave a more relaxed smile
than I'd seen all day and asked softly: "Who is it that you see?" I didn't
need to think about the answer. "I see Katy, ma'am."

She nodded, held my gaze for a moment, and then suddenly the spell seemed
to be broken and she was all business again. I was sent off for what turned
out to be an uncomfortable afternoon learning how to walk in my heels, how
to sit down and stand up, how to go up or down stairs, how to stand and
have a conversation, or sit and chat, and a thousand other details that
slipped through my sieve of a brain. About all I could say by the time it
finished was that I could walk steadily enough ... while my calves ached
unmercifully and my feet were nearly as bad.

Late in the afternoon, I was shown back into the principals' office, where
I found both Mr and Miss Everett waiting for me. "My, Katy" exclaimed the
former, his handsome face creasing into a broad grin as he rose to greet
me, "you have scrubbed up well! How are you going in your lovely new
uniform?"

"Fine, thank you sir", I replied in a dull tone. Truth be told, I was
quite enjoying the feel of the stockings on my hairless legs, and the swish
of my skirt as I moved around just added an extra frisson. But the brief
moment I had shared with Miss Everett earlier in the bathroom had well and
truly passed. I was tired, sore and every glimpse now of my "lovely new
uniform" just reinforced the humiliation I was feeling.

And above all, there was the building sense of dread as I contemplated the
prospect of being forced to go home in my current state of dress ...

Miss Everett's voice cut through my gloomy thoughts. "We're about done for
the day. No doubt you have a lot of questions. Which is a pity, because
we're mot about to give you any answers ... not yet anyway. But there is
one more thing you get to do for us before we send you home."

Her smile was broad and mischievous. "One of our little perks as principals
is to ... have some fun with our newest recruits. Break them in, so to
speak. Especially when they look as enticing as you do."

I looked aghast at her, then over to her bother, whose wolfish grin left me
in no doubt at all about the kind of "fun" to which she was alluding. But
her next words gave me a glimmer of hope.

"Since you're so new to this, we'll let you choose which one of us gets to
play with you." I opened my mouth to give her what seemed the obvious
answer. But she held up a warning finger, forestalling my response.

"Before you choose, you should know that there's a catch." Her voice was
low and ominous and I steeled myself for one more unpleasant surprise. I
was not wrong, either.

"If you pick me", she continued, "you get to go home exactly as you are -
uniform, makeup, hair, the whole package. But agree to just half an hour
with my brother, and you get your clothes back. Plus the makeup comes off.
Only the shoes and the stockings have to stay on for the trip back to your
apartment.

The smile was back now. There was no hint of malice or gloating in her
expression, just an air of curiosity as she looked into my eyes and put the
question: "So, Katy, who gets to have their wicked way with you?"

My eyes darted from one to the other. What a choice to have to make ...

[to be continued]