Date: Mon, 5 Sep 2016 18:39:06 +0930
From: Amanda Stern <astern50@gmail.com>
Subject: My New Career - Part 7 (TG)

Welcome to the seventh chapter of this story of a job application gone
disastrously wrong (or as I prefer to see it, right). if you have any
comments or reactions, please feel free to email me. And  do think about
donating to help support this wonderful site.

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

MY NEW CAREER - PART 7

"So if you could choose any of the girls here, who would it be?"

"Any of them? And I can do whatever I like with them?"

"Total freedom, whatever floats your boat. Put 'em in any uniform you like,
fr'instance."

"And no time limit?"

"No time limit - well, you know, within reason. But could be all day, if
your stamina held out."

"Hmmm, tough choice ... Ivanka, maybe? Miranda? Or perhaps  Scarlett - no
wait, she's gone, hasn't she? Left last month. Soooo ... I'm going to say -
Taylor!"

"Taylor ... hey, great choice. The blonde bombshell, looks great in
anything - and even better in nothing at all ... But listen, you wouldn't
think about picking Katy?"

"Katy? You're kidding, aren't you?"

"What's wrong with Katy?"

"What's wrong? Where do you want me to start? No boobs, for a start. I
mean, what's the point of having a face and body that good if you don't
have a rack to match? And her cock is far too small. Plus she's so
insecure, she thinks people are talking about her all the time ..."

I opened my eyes. "You do realise I'm awake, right?"

Lily chuckled. "Oh my god, you mean you heard all that? What will you think
of us?" She resumed work on my nails. "We're just having a laugh, babe.
Give me the choice of any girl in the College to dress and make up, you're
top of my list. And you know it ..."

"Hmmm, I'm not so sure", said Daniel from behind me. I felt rather than saw
him lift some of the strands of my long, raven tresses and examine them
critically. "I mean, look at the state of this hair. I don't know what
you've been doing it with, darling ... or rather I do. It's all that creamy
'conditioner' the men have been giving you at the Club, isn't it?"

He gave a dirty laugh and resumed his work with the brush. I blushed
furiously and protested my case.

"No fair - it's not as if I ask them to shoot their load all over me.
Except maybe I lend a hand here or there. And like, you know, the odd
blowjob ..."

"Yes", said Lily drily, "I've heard your blowjobs are pretty odd ..."

This time I joined in the laughter. Not much about working and training at
Ceder College was comfortable, but I never felt more at ease than when I
was in the company of the beauticians. Apart from the fabulous looks they
gave me, they seemed to be able to make light of even the most challenging
aspects of what went on here. They knew that I was virtually a captive,
being forced to assume a different gender and perform sex acts for money.
But that didn't mean they couldn't brighten up my day.

And the fact was that if I didn't think too hard about my situation, it
could have been a lot worse. I had come to love the clothes they dressed me
in, the wonderful things they did to my hair, the femininity of my
appearance.

And as for the dancing at the strip club, and the three times now I'd been
required to give handjobs and blowjobs to a group of "special" clients ...
well, that too could be endured, especially with the chemical cocktail that
helped heighten my arousal and lessen my inhibitions. On the first occasion
the drugs had been slipped into my drink. The second and third times, I had
been given the choice by the principal, Mr Everett. I'd opted to take them
because ... well, if nothing else, it helped me excuse my own behaviour. I
really didn't want to think about doing all those things voluntarily ...

Not that it was just the lunches. Since my "initiation" I'd been given the
option of offering "hand relief" (though nothing more) as part of the
services available to customers at Club Angel who paid for a private dance.
I was told it was up to me whether I did this, though the extra money
earned would go into the account that was - or so I was assured - set aside
for my future use.

I had been wary of whether there was a real choice here or not, given the
constant threat that if I didn't do as I was told, compromising photos of
me (in the male guise I could barely now remember) appearing to have sex
with an underaged schoolboy would be released on the Internet. Not to
mention the control I'd signed away over my finances ...

But in any case, I'd pretty much got used to the idea of wanking off men by
now. Besides, many of the clients who wanted to buy some private time with
me had become regulars, who I'd grown to know and - in a strange way -
trust. There were a couple of older guys in particular that I positively
enjoyed seeing, they were so sweet in the way they complimented my
appearance, so grateful for the chance to fondle my body, so awed by my
willingness to handle their scrawny members and tug them to release.

And speaking of old guys ... My live-in relationship with Mr Stokes had
blossomed even further since the night I'd first sucked him off. Our sex
life had certainly gone to a new level. I couldn't believe how horny he
was, or how much staying power he had when I used my newfound skills
with hand and mouth and tongue on his thick cock. But the real revelation
was his willingness to give me pleasure as well.

He insisted that it wasn't fair that he was the only one that got to come,
especially when I confessed that playing with his cock often made me hard.
There was no suggestion of him putting his mouth anywhere near my groin. He
loved ladyboys, but not that much, or at least not in that way. He was
entirely active and dominant in his desires. But he was more than happy to
put his big hand into my panties and toss me off. And when I insisted on
licking my own cream off his fingers and palm, that just aroused him even
more.

There were times when I even fantasised about being fucked by him, though
always with a tinge of shame and guilt that I should even contemplate such
an act - not to say astonishment, for someone still so firmly attracted to
women. But even if he had asked to do that, something that would now seem
so out of character with his gentle and courteous treatment of me, I would
have said no. It was the College that decided what I could and couldn't do
...

And there was the biggest barrier that remained between us. I had thought
so many times about telling Graeme the story of how his pathetic
male tenant had been transformed into the sexy girlfriend who now lived
with him. But there were two impenetrable obstacles. The fear of what the
College would do to me if my indiscretion was uncovered. And the even
greater worry that he would want nothing further to do with me if he knew
how I was spending my time here - and just how many other cocks I was
arousing, fondling and servicing ...

"All done Katy", called Daniel in a singsong voice that cur through my
reverie. I stood up, balancing without conscious effort on the six-inch
heels I now routinely wore, and inspected myself in the mirror. My hair
fell in long wavy curls to my bare shoulders, topped off by the wispy white
lace cap. I looked at each of the beauticians in turn. We could all guess
what my assignment was today, given the maid's uniform and the instruction
to report to the principal's office just before lunchtime.

"Wish me luck, okay?" I said. Lily straightened and leant in to give me a
peck on the cheek. "You don't need it, sweetie", she responded, smiling.
"They'll love you, I know they will."

"Well yeah", said Daniel, "but that's what I'm worried about - them loving
her all over this hair I've just spent half an hour on ..." He gave me a
brief hug and then gestured to the clock on the wall. "Go on, you don't
want to be late."

I was still a little early when I reported to the principal's office, to be
greeted by the new receptionist, Nikki. I had not seen Grace since the day
after what had turned out to be my one-night stand with her. My attempts to
elcit any information about her whereabouts had, as usual, failed
miserably. I had been worrying about what might have happened to her -
though my concern was tempered by a lingering doubt as to whether she had
been acting on the College's instructions, or had at least told her bosses
about us.

Nikki, a willowy blonde who had been dancing in the Club before being
brought in to replace Grace, handed me the now customary glass of organs
juice. She winked as I took it and I smiled in return, but didn't say
anything. The rule at the College was simple - don't speak unless you're
spoken to.

When the summons came, I was surprised to find Kristin Everett in the
principal's office, rather than her brother Gordon. Although they shared
the role, I had seen little of Miss Everett recently. Our weekly "play"
sessions seemed to have disappeared from my regular schedule, something I
was not sorry about. Aside from the other forms of punishment or
humiliation I had been compelled either to experience or to watch being
visited on other students, I was especially glad for a respite from the
heroically sized butt plugs she had often insisted on drilling into my rear.

"Katy", she said in a brittle voice, pointing to a spot in front of her
desk at which I duly stood, "I assume you know what you're in for today?" I
nodded obediently. "Yes, ma'am."

Her face twisted into an unsettling smile. "Jolly good - though there'll be
at least one thing different. Up to now, you've been working with - and
competing against  - some of our more, ah, experienced young ladies. And
doing very well, I hear. But today, you're the veteran. You'll be up
against someone who's a newbie to these sessions - well, kind of, at any
rate."

She lowered her head slightly and peered up at me intently over her
gold-framed spectacles. "Which means, you'll need to lead the way. It's the
usual thing - serve drinks, some chit-chat with the guests, then a
performance on the table that will include you fucking her - but you both
have to come, right?"

At my dutiful nod, she continued. "And then it's time for you both to play
with the guests - and let them play with you. If you can make more of them
come than the other girl, you win  - and it will be the last time you have
to appear at one of these shows, okay?"

"Yes ma'am", I answered crisply. I was relieved to get confirmation
of something that I had previously only suspected  - that if I could only
reap more orgasms than my rival, I would not have to go through this
demeaning experience again. As I followed Miss Everett out of the office, I
was already pumping myself up. The men at today's lunch wouldn't know what
had hit them, I vowed.

But all my positive thinking came to a shuddering halt when I saw who was
waiting for us outside, dressed in exactly the same French maid's costume.
It was Grace.

She glanced briefly at me, her lovely eyes widening with evident surprise,
then quickly looked down again. As Miss Everett headed off down the
corridor, we scurried to catch up. The principal's voice dripped with
amusement as she spoke over her shoulder.

"Bet you've been wondering where your playmate had got to, eh Katy? Well,
she's been undergoing a little ... re-education. This'll be her last day
here in fact, before we send her off to one of our other facilities. But we
couldn't resist getting the two of you back for one last reunion. Not after
seeing how hot you were together. That video's been on high rotation in the
Everett household, I can tell you!"

At the mention of a video, I couldn't help but look sideways at Grace - to
find her doing the same to me. The barely controlled shock on her face
exactly mirrored my own, I was sure. I opened my mouth to protest, but
fortunately for me, perhaps, Miss Everett was still talking.

"Now Grace, I do hope that you're still going to be able to open your legs
for the lovely Katy. I mean, just because she cost you your cushy job
doesn't mean that you should hold it against her ... although I'm sure our
guests today will be wanting you to do just that, ha, ha!"

Tightening my lips, I resolved not to respond - it would only make things
worse. I did not look at Grace again until we had been left alone in the
dining room. When I did, I saw her frown and give a barely perceptible
shake of the head. There seemed zero chance of having any conversation in
here that would not be overheard - or at least not right now. Sighing
inwardly, I said out loud: "Cmon, lets gets some drinks out", and busied
myself loading up a tray.

When the guests arrived, there were two surprises. One was Miss Everett
leading them in. But it was the other that really stopped me in my tracks.

All the guests today were women.

There were both similarities and differences to the groups I'd seen at the
earlier lunches. Like their male counterparts, the diners were
crisply dressed in business clothes, with the occasional skirt, high heels
or crimson lipstick the only obvious concessions to femininity. They
projected confidence and power, in the way they carried themselves and
spoke. Their ages ranged from perhaps thirty all the way up to sixty or
seventy year olds.

But there was none of the bluster or boisterous humour I'd come to
associate with the "special clients" who attended these functions. These
women didn't seem to feel the need to attract attention or show off to one
another. And when Grace and I did the rounds and chatted to them, there was
nothing like the amount of fondling or crude innuendo to which I'd become
accustomed.

Which is not to say that they weren't interested in us - quite the
contrary. Their eyes roamed over our satin and lace-clad bodies and their
smiles hinted at pleasures to come.

One of them, an older woman with close-cropped iron grey hair, invited me
to sit on her lap; but where I might have expected to be to grabbed or
mauled, she simply stroked my cheek and then ran her hands lightly over my
exposed arms and shoulders. I shivered under her touch and my cock
stiffened, but if she noticed the reaction she made no comment.

Her hands came to rest on the top of my bodice. Gently, she traced the
outline of my nipples under the soft fabric, her touch stiffening them and
sending a further quiver through my loins. I'd noticed lately that my
nipples were becoming noticeably more sensitive, something I assumed was a
by-product of whatever hormone treatment I was getting at the College.

"No falsies, I see", she murmured. "No ma'am", I answered. She seemed to be
waiting for me to go on, so I continued. "I, er, don't really see the point
of them. Or at least not in the kind of outfits we have to wear here,
anyway."

She laughed. "I suppose not. Anyway, I'm glad - can't stand them, on girls
or boys. Give me the real thing any day ... Have you said no to those as
well?" The question was asked in a teasing tone. I blushed. "No ma'am - or
at least, I haven't been given the choice."

"And if you were given the choice?" she asked, her fingers still gently
stroking me. Fighting to concentrate in the face of the effect her
attention was having on me, I managed to reply: "I, um, haven't given it
any thought, ma'am - I'm not sure, to be honest."

That was a lie - or at least the first part. I'd often found myself
wondering what real breasts would feel like ... But the arrival of my
questioner's main course spared me any further grilling on the subject.

Soon enough, it came time for Grace and I to put on our performance. In
other circumstances I would have been anxious to get my hands on her lithe
body - indeed I'd lain awake fantasising about just that more than once
since our last encounter. But now the awkwardness of our situation was
uppermost in my mind. It was with more than a little trepidation that I
danced over to her, wondering whether I had it in me to perform as required.

Two things overcame my hesitation. One was a glance at Miss Everett, whose
steely gaze told me all I needed to know about the consequences of failure.
The other was the reassuring smile that Grace gave me as I spun her round
to face me. When I pulled her into my arms and began to kiss her, all my
doubts were quickly forgotten. I swiftly grew hard ... and so did she.

As I pulled down Grace's panties and took her stiff rod into my mouth, I
could see another difference playing out with our all-female audience.
Where the male guests had done no more than unzip their flies, the women
watching us chose to disrobe, shedding their clothes and replacing them, if
at all, with loose, diaphanous gowns handed out by the serving maids.

Grace must have been turned on - had she too been given some sort of
aphrodisiac, I wondered? - because it took only a couple of minutes' work
to bring her to the point of orgasm. Her legs jerked convulsively as she
came, sending wave after wave of spunk into my mouth. I resisted swallowing
it, but held every drop until I had finished cleaning her cock. Standing
up, I opened my mouth and held out my cream-covered tongue for the audience
to see, before ostentatiously gulping it down.

As I pulled Grace into an embrace, she brought her mouth close to my ear
and whispered over the sound of the music that was providing the soundtrack
to our act: "God, I needed that ... they've had my cock locked up in
some awful device since we slept together, it's been horrible ..."

Before I could respond, she added quickly: "I'm okay now though, all
right? But you'd better go ahead and fuck me before that bitch Everett
notices ... Besides, I really want to feel your cock inside me
again. Cos, you know, we may not get the chance again ..."

I didn't need a second invitation. Just as she had done the first time I
had taken her, she lay down on her back with her legs in the air and
invited me to impale her from above, giving me the opportunity to rain
kisses on her lips and her delicious breasts as I drove into her tight rear
passage. It also allowed me to surreptitiously ask her the question that
had been preying on me.

"Did you know? About them recording us, I mean?" Her answer was to give me
a resounding whack on the buttocks, an action that brought an admiring
cheer from a couple of the guests. Startled, I looked down to see her
giving a brief glare, before relaxing her features as I continued to plow
into her. I grinned. "I'll take that as a no", I whispered.

Grace brought her head up to kiss me, then reached round to nibble my ear.
"I didn't know about any of it, you idiot. Would I be on this table if I
had?"

It was, I had to admit, a pretty good argument. A weight I had not even
realised was there seemed to slip from my shoulders. I leaned down to kiss
her again, this time more deeply. I still felt guilty - bit at least there
wasn't the spectre of betrayal as well.

Lifting my tempo, I pounded her butt and was rewarded with several gasps.
And then I was coming, the sweet release making me gasp and moan as I
flooded her depths with my sperm. Groaning, I collapsed on her, my head
resting on her sweat-streaked boobs, her arms and legs clinging to me. For
a moment, I was lost to my surroundings, spent and at peace.

But quickly enough, reality came surging back. As I slid my shrinking
member out of Grace's cum-filled passage, I heard her ask, this time in a
normal voice, "Now what?" As she sat up, a stream of
lsticky residue dripped onto the tablecloth. Scooping some of it up with
her fingers she tasted it appreciatively, smacking her lips. "Yum!"

I grinned back at her. "Competition time. We, ah, see to the guests -
though not, I assume, with these." With a gesture I indicated our cocks -
though hers, I noticed, had noticeably recovered some of its hardness. "The
winner is whoever can get more of them off. But don't ask me if there's
a prize, beyond getting out of doing any more of these lunches- I've never
had the chance to find out."

I looked around to see the diners watching us expectantly - though there
were none of the raucous requests I was used to receiving at this point,
and a few had evidently decided to start on one another, rather than
waiting for us. Slipping off the table and picking my way past a pair of
women who had pulled their chairs together and begun fingering each other's
pussies, I made my way over to Miss Everett. Apart from anything else, she
was the one person in the room to whom I'd previously given
cunnilingus. I'd thought it might be useful to start somewhere familiar.

However, the principal was having nothing of it. "Nice try Katy, but much
as I enjoy that wicked tongue of yours, guests do come first - literally,
you understand. You can, ah, suck up to the boss later." As the guests
around her laughed, she waved a hand at the gray-haired woman who'd
previously had me on her lap. "Try Angela there, she's clearly hanging out
to get a piece of you."

Doing as I was bid, I sashayed over to my target, whose eyes were glowing
as she watched me approach. "Hello Miss Angela", I said coquettishly, "what
is your pleasure?" She smiled voraciously, leant back in her chair and
opened her legs, her gown slipping open as she did so. Where Miss Everett
typically kept her quim hairless, her muff was covered by a tangle of hair,
which unlike that on her head was still predominantly black. "Thank you my
dear, I seem to have a very dirty crack. Perhaps you could clean it out for
me?"

As I knelt down and pushed my nose into her bush, I did my best to ignore
the pungent odour, concentrating instead on finding her clitoris with my
tongue. As I brought it to life, I was rewarded with a shudder and a rush
of fluid. "Lick it", came the gasped command, as her thighs clamped me in
place ...

They would not be released until I had made her come three times (I did
hope someone was keeping count), by which time my tongue was beginning to
go numb. Even then it took two other guests to pull me away. The older of
the two commanded me to lie on the floor and promptly squatted on my face,
pushing down hard and nearly smothering me as she mashed her pussy into my
mouth.

At the same time, I felt her younger companion massaging my flaccid cock
back to life. When it was hard enough, there was a pause, then a sensation
of warmth and wetness as she lowered herself onto me. Waste not want not, I
supposed. Clearly I had been wrong about what we could use to satisfy our
clients.

Which reminded me ... Still fighting for breath and struggling to keep my
tongue lapping against the woman who seemed to me intent on grinding me
into the carpet, I held out two hands either side of me, palms up and
fingers wiggling. For a moment nothing happened and I was about to retract
them when I felt my left hand seized and guided upwards to yet another
pussy. Then the same thing happened on the right.

When, a short while later, I succeeded in bringing four women to orgasm in
quick succession (though in truth two of them idid most of the work), I was
beginning to think that I might be able to win one of these contests after
all ...

******************

Three days later, as I was ushered into the principal's office, my tongue
still felt like cardboard ... and my lips remained tender from the
relentless pubic assault they had endured. But it had been worth it, I
guess. I had no idea of how she could possibly have known, given all those
multiple orgasms, but Miss Everett had declared me a narrow victor. I had
not personally attended to the principal, but from her flushed expression I
assumed Grace had done so - and probably more than once.

As for my erstwhile lover, there had been no fond farewell. She had been
whisked away at the end of the lunch, with no opportunity to say goodbye.
Still, there were doubtless worse ways to part than after shooting one last
load into each other ...

The prize for winning, I'd been promised, was no more of these functions.
But what I hadn't yet discovered was what I would be expected to do
instead. Given my experiences to date at the College, I wasn't sure I
wanted to find out - but I had a sneaking suspicion I was about to be told.

My first indication that something had changed was that both Everetts were
waiting to see me - and the second that I was asked to sit down, rather
than stand to attention. I lowered myself into the chair that had been
indicated and daintily crossed my legs, which today were garbed in white
stockings. Vainly, I tied to tug the short, pleated skirt down to conceal
the white cotton panties I was wearing, but there simply wasn't enough
material. The red plaid mini-skirt and see-through short-sleeved white
blouse were without doubt the skimpiest and sluttiest schoolgirl outfit I
had ever worn at the College - even counting some of the costumes I had put
on to dance at the Club.

"Well now Katy", said Miss Everett admiringly, "you're looking very ...
fuckable". The glint in her eye suggested that she would love nothing more
than to put that statement to the test.

"Indeed", said her brother with a crooked smile, "but before we get to
that, we just wanted to congratulate you on, ah, coming so far so quickly.
I'm not sure we've ever had anyone get to the final stage of our program
this fast. And to cap it off you managed to pass the penultimate test
without any of our, ah, chemical additives to help you along!"

I stared at him as the implications of his last statement sank in. "You
mean, the orange juice ..."

"... was just orange juice, yes", he confirmed, his smile broadening. "At
least after the first time. You really are quite the slut, Katy. Which of
course is why we chose you to do those special sessions in the first place.
And why we're about to send you off on one last assignment before you
graduate from the College."

My mind was reeling from the thought of all those men (and women) I'd
willingly serviced, all it appeared entirely off my own bat (or hand, or
mouth, or cock). But a couple of the words Mr Everett had spoken penetrated
my mental fog.

"Assignment?" I managed to say. "Um, graduate ...?"

He laughed. "You never seem this lost for words when you're flirting with
the clients, young lady ... Your assignment is a simple one. One of our
most important clients has been successful in a blind auction that we
recently held. His bid has won him the pleasure of your company for the
rest of the day ... and tonight."

Could this get any worse? Don't bet against it Katy, I told myself. Aloud,
I asked: "Um, my company, sir?"

He leaned forward and looked at me intently, his face now deadly serious.
"He can ask for whatever he wants, Katy. And you" - he stabbed a finger at
me - "can say yes and no, as you see fit. You go to his house, you have
dinner, you make conversation, you sleep in his bed. Anything else is your
choice. He knows that, it's part of the auction rules."

He leaned back. "But be very aware. The choices you make will define what
happens to you after you've graduated. Or, should I say, what we choose to
have you do. Is that understood?" I nodded  meekly.

Kristin cut in. "As for what some of the options might be for your future,
we'll talk to you in more detail about that when you get back. There's a
car waiting for you outside as we speak. But before you go, there is one
other choice we're going to tell you about - so you can think it over
before making a decision."

The smiles were back on both their faces now and I braced myself, as
Miss Everett continued.

"As you may possibly have noticed, we have been transitioning you to what
we think of as your correct gender. Because you weren't much of a man, were
you ... Martin?"

It was the first time I'd heard that name in what seemed like months. It
seemed strange and unfamiliar. "No ma'am", I replied dully. I could hardly
deny it.

"No indeed. So, Martin is gone and Katy has taken his place. But there's
still something missing - or several somethings, to be precise." Her
brother chuckled, but a little dutifully, and I had the impression
she'd given this speech before. Wait though, she couldn't mean ... She wasn't
talking about ... was she?

Miss Everett's grin stretched a little wider as she watched the play of
thoughts  as if ithey were written across my face. "You're thinking  -
they're going to give me breasts and a vagina .. Aren't you?" This last was
said sharply and I reacted as if was back in the classroom, being
admonished by a teacher. "Ma'am, yes ma'am", I responded miserably.

"Well, let me put your mind at rest", she said in a kinder tone. "We may,
ah, push the boundaries a little here, but we're not monsters. We're not
going to put you through those two operations, unless you really want to
have them both done."

I was starting to exhale with relief, when her next words hit me like a
hammer. "But you are going to have at least one of the procedures. That's
your choice, see?"

As I stared at her, feeling the colour drain from my face, Mr Everett spoke
up. "That's right Katy, it's your call. If you want, we can make you all
woman. Or you can just get a boob job - and the size is entirely up to you,
by the way. Or, if you like, no breasts - but then no cock either. So if I
were you" - he stood up and gestured me to do the same - "I would think
very carefully before making a decision." He shrugged. "Because if you
don't choose one or the other, you'll get both."

I was barely conscious of leaving the room with him and walking to the lift
well. All I could think was - what the hell was I going to do?

(To be continued ... Feel free to email the author with any advice for poor
Katy!)