Date: Sat, 23 Jan 2016 18:17:07 +1030
From: Amanda Stern <astern50@gmail.com>
Subject: My New Career (Part 5) - TG

Please find below the fifth part of my story, for inclusion in the
Transgender Control section.

- Amanda Stern


Welcome to the fifth chapter of this kinky tale. if you have any comments
or reactions, please don't hesitate to email me, as I adore hearing from
anyone who shares my love of crossdressing, writing or both. And  do think
about donating to help support this wonderful site.

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

MY NEW CAREER - PART 5

Spent, streaked with sweat and still amazed, naked except for the
ubiquitous stockings, I walked on unsteady legs to the bathroom, closed the
door and leant back against it, trying to collect my scattered thoughts.

I had faced a lot of challenges in the past couple of months. The ruthless
feminisation that had been imposed on me, to the point where I was finding
it hard to remember what it was like to walk or talk like a man, let alone
look like one. Being forced to abandon what I'd thought of as a career in
teaching and instead work in a strip club, flaunting my body and teasing
voracious men into giving up cash. The sick feeling of helplessness every
time I was reminded just how much the Ceder College controlled my
existence. And much more besides.

But this was something else again. I might have lost all the trappings of
masculinity, I might have started even thinking of myself as Katy,
not Martin. But regardless of the humiliations heaped on me, I could
retreat within myself and find that core of feelings and desires that still
belonged to my old self. Or so I'd thought ...

I walked to the basin, washed my face and then mechanically started
 brushing my hair and repairing my makeup. And as I did so, I thought again
about what I had just done ... and wondered, what had happened to make me
love it so much?

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

The initial shock at being sent to dance in Club Angel  had gradually worn
off over the next few weeks. Although much of my time was still spent in
lessons at the College, I was rostered to work for an hour or two each day.

While I always started with a show on the stage, much of my time was in
fact spent around the club mixing with the clientele. I was expected to
chat with them and encourage them to buy me expensive drinks (which I was
instructed to pour away when they weren't looking) or, preferably, to pay
me for a "private show". These were held in separate booths and involved me
stripping off my clothes (at least to my panties), teasing the client and
letting them fondle my body - again, except between my legs.

My fears that I wouldn't have enough on my chest to display, or that my
real gender (or what I hoped was still my real gender) would quickly be
rumbled, were dispelled on my second visit to the club, when I was asked by
a client whether I was "one of those girly boys".

It seemed that the customers were fully aware that some of the "girls" in
the club were naturally female, and some weren't: indeed it appeared to be
something of a selling point. Most of the clients who wanted private shows
could already see I was sufficiently flat-chested to probably be a guy
underneath. Those that couldn't either asked, or found out in the booth -
and not once did any of them show any irritation at my being something
other than all woman. In fact there was probably an element of
self-selection: if they'd wanted a more busty or curvy dancer, they
wouldn't have approached me in the first place.

Despite this, I still found myself feeling disappointed sometimes that I
didn't fill out my glamorous costumes, or have more to display when I
took off my top. Once or twice I even thought about asking Mr Everett -
who I still tended to see only at the club - if I could use some of the
fake boobs he'd mentioned. But that really wouldn't have made sense - the
artifice would have been exposed (so to speak) the minute I started
undressing.

What was really scary? The fact that I'd caught myself wondering what real
breasts would be like ... That and something else: the arousal I
sometimes felt now when turning men on. It wasn't any kind of attraction to
the clients themselves - or at least I didn't think so. Even if they were
young and good-looking - which most weren't - I didn't feel any urge to
touch or kiss them. But if I made them excited, if I saw or accidentally
felt their erection ... well that made me tingle. And just a little bit
hard myself ...

Worse still, it was happening at home. I had bitten the bullet and agreed
to move in with Graeme, my landlord. I simply didn't see any other option.
For the first few nights, he had insisted on sleeping on the couch,
chivalrously insisting that I take the bed to get what he kept calling my
"beauty sleep". But after seeing him so stiff and sore in the morning -
hardly surprising, given the need to squeeze his large, sixty-something
frame onto such a short sofa - I had taken pity on him and agreed that we
both use the bed.

It was a queen size, big enough so that we weren't on top of one another.
But with the nights getting colder, it was only natural sometimes to huddle
together for warmth. And after leaving me alone initially, he had taken
again to wanting to kiss and cuddle. In the circumstances, given that I was
getting free board and lodging, it seemed churlish not to let him have his
fun. Besides, I'd got used to it ... and there was something oddly
endearing about his passion, his excitement, his sheer wonder at making out
with the gorgeous creature he clearly thought me to be.

And where kissing started, so arousal followed. And I would wrap my hand
around his meaty cock and sometimes pump, sometimes tease him to release.
He never asked me to do more, though I could see in his eyes he would have
liked to. And I felt no urge to go further. But what I did feel,
increasingly, and confusingly, was an arousal of my own - something I went
to considerable pains to conceal, but fretted about all the same.

All in all though,, my life at home had become much easier, even pleasant.
Graeme was good and attentive company, treating me in many ways as a kept
woman. He cooked for me, took me out for dinner or a movie once a week, and
brought me pretty clothes. He especially loved getting me lacy lingerie,
which I would model for him or wear to bed - something which in turn
increased both his ardour and his chances of getting a handjob. I mean, it
seemed only fair ...

The College had also loosened some of their controls somewhat, even though
it was still made very clear to me that I had no choice at all about either
my lessons or my work. While I was still expected to be in high heels when
I both arrived and left, the biometric lock that had previously kept them
on until late each night had been removed. By now I had got used to them
anyway, so while I certainly no longer wore them while at home, it was rare
for me to go out in  anything else.

Truth be told, I had come to love the feel of the clothes I wore, the way
the different fabrics moved against my now permanently hairless skin, the
way I looked. I felt ... sexy. As my hair had grown out, so Lily and Daniel
were able to experiment with different looks ... as indeed I often did now
as well.

Today I had it braided and then tied back into a tight bun, with a few
stray wisps left to frame my face. The look for the day had been Sexy
Secretary, so I had paired an electric blue silk blouse with a tailored
black jacket and a very short black skirt which showed off my legs, looking
fantastic in patterned black nylon and six-inch pumps. In fact, the look
was really Fuck Me Hard Over a Desk, and judging from my earnings at the
club, that's exactly what some of my clients would have liked to do to me
...

Unusually, I was wearing my day outfit to go home in this evening, rather
than changing into more nondescript clothes. For one thing, I wasn't going
straight home. And for another, I had my own sexy secretary to see.

Catching up for a drink with Grace had become the high point of my week,
without exception. Although she remained very reticent to talk about
anything that happened at the College, or her life away from it, we still
managed to find a lot to chat and giggle about.

As I walked into the drinking hole she had chosen this week - we always
tried to move around, as well as avoiding anywhere the other College staff
were known to frequent - i had a real spring in my step. But two things
stopped me dead in my tracks as I caught sight of her at the bar.
Unusually, she was still wearing her work uniform - an outfit very similar
to mine, but with the classic white blouse, unbuttoned to display more than
a hint of cleavage. And she was talking to two young men in suits.

As I stared at her she caught my eye across the room, waved and then said
something, smiling, to the men. With a laugh she left them and came over to
greet me. "Hey girlfriend!" she called brightly and stepped in close to
peck me on the cheek, lightly resting a hand on my hip. As she did so I
felt a familiar shiver at her nearness and inhaled her delicate and
familiar aroma.

"Hey yourself", I returned. Jerking my head at the two men, I asked as
lightly as I could: "Who are your friends?"

She smiled, took my hand and led me to a table. "No idea", she said, "I
think they were just trying to chat me up. Not my type though ... Okay,
this looks good, I'll keep the chair warm, you can go get them in." Her
smile broadened as she sat down. "It being your turn to buy and all ..."

I nodded my acquiescence and headed to the bar. I was now getting a small
amount of pocket money from the College and it was actually quite nice to
be able to buy stuff again. I ordered a bottle of our favourite riesling
and was just about to pay for it when a voice beside me asked: "Any chance
we can take care of that and help you two gorgeous young ladies drink it?"

I turned around to find one of the men Grace had been talking to smiling at
me, his eyebrows raised. He was really good looking ... if you liked that
sort of thing.

It was not the first time I'd been approached while out with Grace. And I'd
become pretty comfortable talking with guys at the club. Keeping my voice
soft and a touch higher than my natural tone, as I'd been taught, I
affected a look of surprise. "Oh wow, that's really sweet of you. Only ..."
I gave him my most dazzling smile.

"Thing is you see, my friend and I have got to drink up quickly, then spin
the bottle to work out which one of us is going to eat out the other's
pussy tonight. And do you know how much we love having men watching us and
then joining in? That's right - not in the slightest. See ya!"

Taking my change, the bottle and a couple of glasses I strode back to the
table, putting an extra wiggle in my hips. Grace was staring at me. "Oh my
god", she said, "what on earth did you say to him??? He's still trying to
pick his jaw off the floor ..."

"Who, me?" I asked innocently, sitting down and then pouring out the wine.
"Nothing really ... Now, tell me why you're still playing the secretary
babe, I thought you were sick of that outfit?"

She took a long pull of her drink and then grinned at me. "I am, usually,
but I saw what you were wearing today and I had a feeling you were going to
keep it on, so I thought it'd be fun if we, you know, matched ... Now
anyway, tell me how things went today at the club, I want to hear about
every tease you put those poor men through ..."

So we talked, and drank, and talked some more. And somehow one bottle
turned into two. We didn't normally drink so much, but we were both in a
buoyant mood and the time slipped past as easily as the wine slid down our
gullets. By the time we got up to leave, we were both more than a little
giddy. As we walked slowly to the exit, concentrating hard to stay on our
heels - or at least I was anyway - Grace turned to me, her face serious for
virtually the first time that evening,

"Listen Katy", she said, slurring slightly, "would you mind coming back to
my place? It's not far from here and there's something I'd really like to
show you ..."

I was surprised, as I'd never seen her apartment, though I knew she lived
near the city centre. "Sure", I said, "why not? Only you'd better be
offering coffee rather than more wine, or you'll have to roll me into work
tomorrow ..."

She nodded gravely, made as if to say something, then taking my arm in
hers, led me outside. "It's this way", she said, "won't take us long ..."

In fact it took a good twenty minutes, at our admittedly slow pace. But
soon enough we were walking into the hallway of a very modern and well
appointed apartment. As Grace closed the door behind me I peered into a
spacious living room, with a gleaming and well equipped kitchen beyond it.

"Wow", I said admiringly. "I had no idea you lived so well!" Turning back
to her, I continued: "Want to give me a tour? Unless of course you want to
show me whatever-"

The sentence was cut off as she grabbed me and pushed me hard against the
wall. For a moment she stared at me, her eyes wild. Reflexively, I tried to
ward her off. But my cry of alarm was cut off as she leaned in and crushed
her lips against mine. After a moment of consternation, I returned the
kiss. Her lips felt so soft and creamy, so different to what I'd become
accustomed to with Graeme, her tongue darting into my mouth ...

I gently disengaged, pushed her back so that her face came into focus. Her
eyes were wide, her expression almost scared. I shook my head. "Tastes so
different", I murmured inconsequentially, "kissing a girl with lipstick on
... On me, I mean. Or both of us ..."

There was a pause and then suddenly we were in each other's arms, kissing
again, pressing tightly against one another. And my hand was running down
her back, stroking it, then reaching lower to grab her behind, just as I
felt her doing the same to me. As our nylon-clad legs came together I
thrilled at the contact, marvelling at the sensuous feel of the fabric.

After a long moment we broke apart. Her expression was still intense, but
determined now rather than afraid. "I want you", she said in a low voice,
then drew me down the corridor into what was obviously her bedroom. Turning
back to face me, she threw off her jacket, then slowly, looking at me the
whole time, unbuttoned her blouse, and unclipped the white, lacy bra that
lay beneath. Reaching down, she took both my hands, then brought them up to
place them on her soft, inviting breasts. As I gently stroked the nipples,I
felt them come alive under my touch. She moaned softly and I let out a
shuddering sigh. "Oh Grace ..."

And then we were on the bed, pawing and groping at each other, crying
incoherently as we tried to tear off our remaining clothes and
simultaneously bring our bodies together. I was quickly down to my panties
 ... but then stopped, suddenly afraid to reveal what was underneath.

But Grace did not hesitate. With a smooth movement, she pulled my panties
down, disengaging my engorged member from its protective sheath. With one
hand on the shaft, she used the other to push me down so that I lay flat on
the bed. Then, after kissing me once more, fiercely, she took her head to
my groin. In a second she had enveloped my straining cock in her warm, wet
mouth.

The sensation was incredible. I had barely touched myself during my time at
the College, so wary had I become of my own impulses. And even as a man I
had rarely experienced oral sex. So to now have this gorgeous young woman
fellating me, her tongue flickering over the sensitive glans as her lips
slid up and down the shaft ... there were no words to describe it.

Looking down at her head bobbing up and down, I was sorely tempted to just
lie back and let her deliver me the sweet release that would surely not be
too far away. But I wanted more ... "Grace", I said hoarsely, "I don't
think I can ... last too long  ..."

She looked up, grinned and then slowly, lasciviously, ran her tongue over
the tip of my cock. "We can't have that, can we?" she said playfully.
"Besides, I want it somewhere else ..."

She rolled alongside me and we kissed again, my free hand fondling her
beautiful breasts, then slipping down to the top of her panties. Before I
could slide it inside, she grabbed it and held it tight. Breaking from the
kiss, she looked into my face, the smile gone, her expression once again
intense. "Katy", she said softly, "I did say there was something I wanted
to show you ..."

She guided my hand inside her panties and onto ... a lump. A meaty lump
that throbbed under my touch ...

I snatched my hand back and gave her a startled look. She held my gaze
steadily, almost defiantly. I heard a rustle as she pulled down her
panties. She glanced downwards and I followed the look. Standing out proud
from her lithe body was the last thing I could have expected to see. It was
small, smaller even than mine, but no less erect. And unmistakeably a cock.

As I stared in consternation, Grace took my unresisting hand and gently
guided it to her member.. As my fingers closed around the shaft it throbbed
again. And so did I, as she transferred her hand to my own appendage.

"It's part of me", she breathed, "and you do want me ... don't you?"

For a second we were motionless. And then we were kissing passionately
again, crushing our lips together, tongues moving urgently. And as if in a
dream I felt my hand stroking her shaft, reaching down to the bottom to
feel the tight skin of her hairless ballsack, as her hand roamed over me in
turn.

Then, without any conscious decision, I was on top of her, still raining
kisses on her cherry lips. And now our cocks were pressed together and both
the hardness and softness of her were driving me wild. And I knew her
excitement matched mine, when she gasped "Fuck me ... please, fuck me!"

Her words pulled me up short. I wanted to , but ... She must have
understood my confusion, because she gestured frantically at a bedside
cabinet. "In there, top drawer, lube ..."

Lifting myself off her, I scrabbled for the drawer she'd  indicated and
found of tube of lubricant. Turning back to the bed I found Grace on her
back, legs drawn up, knees to her chest. "Give it to me", she called,
motioning me back onto the bed. As I knelt in front of her, she ripped the
top off the tube and squeezed out a generous dollop of viscous fluid.
Reaching between her legs, she smeared it around her puckered anus, then
pushed some inside.

Lifting her legs high she guided me into position, bringing me forward and
over her. I paused for a minute, still struggling to take in what was
happening, what we were doing, what we ... were.

And then my cock was moving irresistibly into place, pressing down against
her exposed asshole. There was a brief moment of resistance and then need and
desire drove me inside. It was so tight, tighter than the few vaginas I'd
penetrated, and for a moment I was worried that I might hurt her. "You ok?"
I asked, unable to keep the anxiety out of my voice.

She laughed then. "God, yes. I've wanted this since I first saw you in that
schoolgirl outfit ..." Then her expression grew serious again. "Now
just fuck me, ok?"

I started to thrust, slowly at first, then picking up speed as I opened her
up and the lube did its work. As I did so, I started to go deeper,
tentatively at first, then ramming down until I was slapping against her
ass. I must have hit some kind of spot, because she let out a cry. "Oh god,
yeah, right there, right there ..."

As I settled into a rhythm I leant forward and for a few moments alternated
kissing her willing mouth and licking her nipples, all the while driving
deep into her, or as deep as I could. I would periodically be rewarded with
ecstatic moans as I hit that magic spot.

And then I looked down for the first time since entering her and was
transfixed by what I saw. There was my cock, disappearing inside her back
passage ... and there was hers, still fully hard, flat against her
stomach. As I watched, she brought one hand up and began first to stroke
it, then pump it, using the remnants of the lube in her palm.

The sight was erotic beyond belief and it drove me to fuck her even harder.
And now her gasps were coming with almost every stroke, and I felt a
pressure building inside, aching for release. It had been so long, and to
have this gorgeous creature underneath me, her beautiful face twisted with
lust and desire, her luscious breasts there for me to taste, her tight hole
taking everything I could offer, her hard cock a blur as she wanked it
furiously ...

It was nothing I could make sense of, I just existed in the now as I
savoured the sight and sound of what we were doing, felt the sweet pressure
on my rock-hard member, watched in amazement as hers erupted and spat
streams of creamy white spunk over her belly and breasts.

And then I was coming too, in wave after wave, crying out with ecstasy and
release as I emptied myself far inside her, the orgasm more intense than
any I could remember. And then the sweetest sensation of all, locking into
her shining eyes and seeing all my joy and desire perfectly mirrored,
leaning down to kiss her tenderly, her lips soft and warm against mine ...

With a groan I lifted myself off her and collapsed beside her on the bed.
For a moment I lay there panting, still feeling the aftershocks of my
climax. And then, as if at some unspoken command, we turned towards one
another and embraced, pressing our bodies together, heedless of the liquid
remnants of our passion, our shrinking members gently touching as we kissed
again.

Nothing was said. The questions, the explanations, they would come later.
For now, there were no words, just bodies entwined, and at peace. After a
while, we just lay in each other's arms, and as I listened to the sound of
her breathing and took in her scent, I gradually slipped into a
deep slumber ...

I had no idea what time it was when I awoke. I only knew I had been
dreaming about Grace, about kissing her breasts, running my hands down her
stockinged thighs, fondling her cock, feeling my own stiffen in response.
And I realised that right now, not in a dream, but here in her apartment,
on her bed, my cock was indeed coming alive under her gentle touch.

As I opened my eyes, I saw she was looking at me with a half-smile. She
kissed me gently, then said playfully: "Oh, I'm sorry, did I wake you up?"
While she said this, her hand became busier and I stiffened to full
erection.

Without thinking, I reached down to find her own member. It was already
hard, but leapt and throbbed under my touch. As I caressed it, my mouth
found hers, and I marvelled again at how that combination of soft and hard
flesh could so inflame my senses.

This time there was no desperate urgency in our lovemaking. We caressed and
explored each other's bodies for what seemed like forever, before I took
her doggie-style, slipping easily inside, my penetration greased by the
remnants of my first, shattering climax. This time my strokes were long and
leisurely. When I tried to pick up the pace and drive deeper to find
whatever spot had so aroused her last time, she dissuaded me, content to
move her rump in time to the slow and steady rhythm of my thrusting.

The orgasm this time was much longer to arrive and not so powerful, but no
less sweet, as I arched my back and shot my load inside her,  "Mmmmm",
purred Grace happily as I slid out of her, "that's what I wanted, you
filling me right up ..."

She got up off the bed and then squatted down on the floor. I watched,
fascinated, as a steady stream of my cum dripped from her behind. She
reached between her legs, caught some of it on her fingers, then licked
them clean. She laughed when she saw my expression. "What? I just wanted to
see what you tasted like ..."

Once again though, her face grew serious as she rose and stood by the side
of the bed, gently stroking her stiff cock. She looked down at me and said
softly: "My turn now - don't you think?"

In answer I swung my legs down and sat on the edge of the bed. She moved
forward slightly to stand between my legs, her member jutting out towards
me. I hesitated, but only for a second. She had given herself to me,
utterly and completely. If she wanted this, I could not refuse her. Leaning
forward, I took her into my mouth.

Until recently I would have gagged at the very idea of sucking a cock. But
after weeks of Miss Everett forcing me to lick and suck a variety of
dildos, most much bigger than what Grace was packing, I wasn't just used to
it - I had some idea of what to do. So as I wrapped my lips around her meat
I didn't just take part of her, I let the full length slip down my throat,
going all the way to the base of her cock. I held her there for a few
seconds, gagging slightly (I hadn't yet lost the reflex entirely), then
released her.

I was rewarded with a long moan of appreciation. I ran my tongue a couple
of times along the shaft, then used it to gently probe the glans. As I did,
I looked up and asked: "Is this what you had in mind?"

Grace let out a long sigh of pleasure. "Oooooh, yes ..." She gently placed
her hands on either side of my head and started moving it towards then away
from her, so that her rock hard cock moved in and out of my mouth. I made
an O with my lips and picked up the rhythm, careful to keep my teeth out of
the way as I'd been taught (Miss Everett had spanked me unmercifully if she
ever saw bite marks on her dildos).

It was just the way I'd experienced it in those lessons ... and yet totally
different. Dildos, no matter how lifelike, were not warm, they didn't feel
of flesh - and they definitely didn't twitch and throb. And the person
holding them didn't react to every lick, every sudden squeeze of the lips.
They didn't moan and gasp, they didn't start panting, their legs and
hips didn't shake with arousal ...

I was sucking her faster now, or she was forcing me to, it didn't matter
which. There was no subtle stimulation now, no teasing, no clever use of
the tongue, just suction, the provision of a wet and willing hole into
which to plunge her meaty sword. Reaching round behind her, I ran my hands
up and down her nylon-clad legs, then grabbed her buttocks and started
pulling her even harder into my mouth.

And now she was no longer moving my head, she was thrusting with her hips,
spearing herself into me, fucking my face. I felt her whole body stiffen,
every muscle tensing, and she cried out: "Oh fuck, yeah, Katy, that's it,
that's it, just a little bit more, keep going, oh yeah, that's it ... oh
fuuuuck ..."

And the living thing in my mouth bucked and spat, and I felt jet after jet
of liquid hit the back of my throat. I swallowed convulsively, barely
registering the salty taste as I gulped it down. And I would have pulled
back then, but her hands held my head in place, as she pushed her jerking
cock deep into my throat one last time. As her thrusts slowed and became
shallower I opened my mouth and took a ragged breath.

And then, surprising myself, I closed my mouth over her again and sucked a
little more, as I had seen girls do in porno clips, teasing the last drops
of cum out and licking her cock clean. And I felt  a surge of ...

For a minute I wasn't sure what emotion I was feeling. And then I realised
with a shock that it was pride. I had brought her to orgasm with my mouth,
sucked her off and swallowed every last drop. And as I looked down, I saw
that I was already hard again ...