Jamie's Descent

[Transgender Stories]

Jamie's Descent Part 1

By Nikkie

What did we do before e-mail? How did we manage to get through the day
without that endless stream of dirty jokes, funny photographs, gossip and
links to dodgy websites that now fill our in boxes?

Yea, yea, I can hear you grumble. Get on with it; I can hear you say. Well,
dear reader, it was one of those e-mails that started me down the road
to....oh, you'll find out soon enough.

I was 18 and had just come down to London from my home in Norfolk after
leaving school. A friend of my father's had offered me a job in an office
of a finance company for which he was the Finance Director. Wall Street it
wasn't; like millions of other office rabbits around the world, I shuffled
papers, produced figures for reports that never seemed to get sent
anywhere, made endless cups of coffee and kept the global economy humming
along nicely. Charles Dickens would have recognised the office, no problem.

Also like millions of other office rabbits around the globe, I discovered
there is one thing that can keep us from going insane- e-mail. It was a
life saver. Relief from all the hours of tedium came in the shape of the
messages that poured into my in-box. We had the usual warnings from the
company about not using e-mail and the internet for your own use, but
whoever paid any attention to that?

One day I opened an e-mail to find this message.

Are you ready for this? Be careful, this could really change the way you
look at life. Take the Lady Boy Quiz!

Bah, humbug, I thought. So I clicked on the link and up popped a series of
pictures of girls naked from the waist up. Yes, of course, at that moment I
closed it down and deleted it right away - not! I scrolled down and there
must have been 20 photographs, all of outstandingly beautiful girls.
Blondes, redheads, Asians, black girls - all absolutely gorgeous. I knew
what Lady Boys were. My elder brother had gone on a rugby tour a couple of
years before to Australia with a stopover in Bangkok. He had come back with
stories that made my hair stand on end. One story in particular had stuck
in my imagination. One of the team had got very drunk in a bar and the
other lads had paid for a bargirl for him. Except this was a very special
bar girl. After many pints and much prompting my brother revealed that he
had been the guy they set up.

He claimed he vaguely remembered this gorgeous girl taking him into one of
the back rooms. He remembered her stripping down to her knickers before she
stripped him and pushed him onto the bed. He claims she gave him the best
blow job he had ever had (I don't actually think he had that many before).
My brother then maintained he had passed out. Fair enough, except that at
some point one of the guys had crept in and taken a photograph. A couple
more pints and he pulled out a photograph from his wallet.

It was a very poor quality shot, but it clearly showed my brother, stark
naked on the bed, eyes closed and with a look of ecstasy on his face. Also
on the bed was a gorgeous Asian girl who was energetically giving him a
blow job. What was also obvious from the photograph was the fully erect
cock sticking out from the girl's knickers which she was stroking in one
hand whilst clearly holding my brothers cock with the other.

I clearly remember the feeling I had looking at that picture. I felt myself
getting dizzy and my mouth was dry as I looked at the picture. I felt
myself blush and my cock twitched as I held the picture in my hand. My
brother then snatched it back and threatened to beat the living shit out of
me if I ever told a soul about it.

As he was 6 feet 4 tall and built like a gorilla whilst I was only 5 ft 7
and a fraction of his size, I took him seriously. We were called Little and
Large by almost everyone and I got stuck with it as a nickname.

Six months later I headed to London, but I guess I forgot about the
photograph until I saw the girls in this quiz.

All you had to do was tick a box by each picture if you thought the girl
was a ladyboy.

Easy peasy, thought I. Not so, as it was really difficult to tell. They
were all stunning and in the end I pretty much ticked the boxes at random.

At the end of the quiz it calculated your score and I managed to score only
3 out of 20 right. I couldn't believe it. I went back through the pictures
and that's when I think I began to remember my brother's picture. To be
honest I remembered the feeling more than the picture. I began to feel
dizzy and my mouth felt dry. I actually think I was rubbing the growing
bulge in my trousers when my supervisor's voice made me jump out of my
skin.

"James! What are you looking at?" Vanessa, my supervisor had appeared
round the corner of my cubicle.

"Nothing, uh, just some figures," I managed to blurt out. I closed the quiz
down instantly, but I couldn't tell if she had seen anything on the screen.

"Anything interesting?"

Was she being sarcastic?

"No, no, well, yes, it's the month end sales stats for your report," I
mumbled.

"Good, make sure I have those by this evening." She turned on her heels and
stalked down the corridor.

Now Vanessa was the office Goddess. She was tall, may be 5ft 10 or so in
her stiletto heels, which she wore everyday. Somewhere in her background
there must have been some Viking genes; long blonde hair, clear blue eyes
and legs so long they went straight to heaven.

I had been put into her team from the start and for some reason she seemed
to take against me. She would get on my case every time she could. Any
small mistake would be blown up out of all proportion. Worst of all she
somehow knew that I had got the job through the old boys network and that
seemed to wind her up even more. Frankly, I was a nervous wreck when she
was around and I was planning to get a new job as soon as I could.

Over the following days I would go back to the quiz and look at the girls
whenever I got the chance. One evening I was working late and was looking
yet again at the girls when I spotted a link at the bottom of the quiz.

Click here to change your life.

I looked around but the rest of the cubicles were empty and I hesitated a
moment but then clicked on the link. Surprise, surprise, it took me to a
porn website.

"Lady Boy Heaven. Everything you wanted in a girl and that bit more", the
banner screamed out. I looked around quickly but there was still no-one
there. It was a pay site but there was a button to click for visitors. I
clicked and the screen filled with an image of a beautiful Eurasian girl on
her knees sucking the cock of what appeared to be another ravishingly
pretty Asian girl.

I began to feel light headed and I felt a flush creeping across my face. I
could now see the first girl also had a tiny little cock which the second
girl was stroking. I could feel the blood rushing through my veins. I
clicked again and again. Scene after scene of ladyboys sucking, fucking,
and wanking flashed across my monitor. My hand strayed naturally to my
groin and I felt my cock harden as I hungrily took in every new picture. I
lost track of time completely.

My phone buzzed and I jumped clean out of my chair. I looked at the number
and panicked. It was Vanessa's extension. I picked up the phone and tried
to say hello, but my tongue felt like it was three times too big for my
mouth.

"James, you're working late. Are my figures ready yet?" Vanessa's voice was
calm and assured.

"Well, yes, I've just finished them," I managed to say.

"OK, well I'm still here too, so e-mail them to me and come to my office so
I can see if they are alright."

I wanted to protest but the phone had already gone dead. I quickly e-mailed
the figures and walked around the building to Vanessa's office. It was in
the executive part of the building and I had always wondered how Vanessa
had managed to wangle an office here. It was pretty late now and the only
office that was lit was Vanessa's.

I stopped at the door and knocked.

"Come in James."

Vanessa was sitting behind her looking at her computer monitor as I walked
in. She waved a hand to the chair in front of her desk and I sat down.

"James, the figures are fine." She still wasn't looking at me.

"Thanks," I mumbled.

"They're fine but its not that I want to talk to you about." She turned to
look at me for the first time, and her eyes seemed to glitter as she spoke.

"Yes, it's about something completely different. James, you are aware of
the company policy on the misuse of corporate assets aren't you? Especially
the unauthorised use of office technology?" She smiled as she spoke, "Well
even if you're not it doesn't really matter."

It was about now that I began to realise what this about and my heart
started to pound.

"You see, James, we take the abuse of corporate IT here very seriously and
we have installed some very clever technology that allows us to monitor
what our employees are doing on the Internet. I noticed that you were
working late this evening and as a part of my responsibility I decided to
check what you were doing."

She was smiling sweetly as she spoke in an almost apologetic tone. I
couldn't take my eyes from hers. I was as transfixed as a mouse in front of
a cobra. I'm not sure I was even breathing by this time.

"James, can you explain to me what part of your role involves visiting an
internet site called," she paused and looked at the screen probably to drag
out her enjoyment of the moment. "Lady Boy Heaven?"

I swear I died at that moment. My mind blanked. All I could do was look
straight into those eyes.

"James, I'm waiting"

"I, I, I it was a mistake" I blurted.

"Yes, James, I think I agree it was a mistake for you to do this," she
said.

"No, No, I mean I just clicked on a link in an e-mail from a friend and
soon as I saw what it was I came back out," I managed to squeak.

"James," she sounded now like a teacher talking to a stupid pupil. "We both
know that's not true, it's all here on the report." As she spoke she swung
the monitor round, "You spent 30 minutes on that site. Are you telling me
it took 30 minutes for you to work out what Lady Boy Heaven was? I took a
look too and it took me, oh, all of 30 seconds to work out that it's a
website for people interested in having sex with shemales. James, are you
interested in that? Is that why you visited this site?"

My eyes dropped to the floor, and I felt my face redden.

"James, do you want to have sex with shemales? Is that it?" She was
relentless. "Or is it that you relate to those shemales? Do you really want
to be a shemale, James? Or should I call you Jamie, perhaps?"

I blushed even more deeply and I stared at the floor. Her voice took on a
different tone.

"Jamie! Look at me now!" She almost barked this out and my eyes flew to
hers. "Answer my question."

"No, I mean, yes, I mean, I don't know."

I felt my blood draining away from my face and I shivered but I couldn't
take my eyes away from hers. She held my gaze and I felt whatever self
control I had left drain away. Her eyes seemed on fire and I felt a strange
sense of power passing from me to her.

"Jamie, well we are confused then aren't we? Well, Jamie, let me tell you
what I think you are. I think you're really a sissy boy. I think you're a
cocksucker. I think you want to be a subservient little sissy. I think you
want to be a pretty little ladyboy who only wants to stroke and suck
cock. I believe you want to be one of those girls on the website."

Her words were roaring around in my head. I felt sick but I couldn't break
eye contact.

"I've thought so since the day you started here. I have had my eye on you
ever since then. Oh, you might not have realised yourself. I knew it when
you opened that quiz. Oh, yes, I sent you that. It had a piece of code in
it that tracked when you opened it; so I knew just how often you went back
to look at it. I just added the website link to it and waited. I knew you
would come to me eventually. I just waited and you rushed willingly
straight into my little trap."

While she was speaking she stood up and moved slowly round the front of the
desk until she stood over me. She slowly drew her index finger along my
lips as she spoke.

"Yes, I know what you want Jamie. You want to serve me don't you? Remember,
I have all the evidence I need to get you dismissed instantly from this
firm and I would make damn sure any new employer would get to hear about
your surfing habits."

I couldn't believe it as my head nodded slowly in agreement.

She pushed her finger past my lips and into my mouth. My lips seemed to
naturally form around her finger and as she moved her finger slightly in
and out I began to suck gently.

"That's so good Jamie. You know that feels do good don't you, Jamie," she
began to coo.

I felt so powerless, but so excited at the same time. I closed my eyes and
continued to suck her finger.

"Keep your eyes closed Jamie." Her voice changed again. This time it was a
voice of power. A power that should not be contradicted. I felt a touch on
my trouser zip and I couldn't stop my eyes opening.

"I told you to keep them closed didn't I?" she barked. Her hand caught me
across the face and I recoiled from the sting of the blow.

"Do as I tell you," she almost snarled.

I snapped my eyes closed again. I felt myself slipping deeper and deeper
into the darkness. Her finger returned to my mouth and I started to suck
again. I felt her other hand again touch my zip.

"My, we are excited by all this aren't we Jamie? I can feel you are really
enjoying this."

Her hand kneaded my cock and I couldn't help squirming in the chair as I
sucked her finger and she stroked my now painfully constrained
cock. Whatever was left of my self control had now vanished. Instead, I
felt strangely at ease, now that I had totally surrendered to the power of
this woman.

"Jamie, look at me now!"

As I opened my eyes she slipped her finger out of my mouth. Her eyes bore
into mine and she brought her face right in front of mine. Her lips brushed
mine and her tongue darted out and past my lips. She continued to rub my
cock as her tongue probed the inside of my mouth. Her eyes remained locked
on mine all the time.


She suddenly drew back and once more slapped my face. It stung so hard I
began to whimper. All this time she had continued the pressure on my cock,
rubbing and caressing it and I ached for release.

She stretched out her hand again and I tensed for another blow. Instead,
she caressed the cheek gently with her finger tips and spoke softly again.

"Jamie, if you displease me I will punish you again, but if you serve me
well I will allow you to live out your wildest dreams. You will learn the
pleasures of serving me and you will understand the ecstasy of fulfilling
your true destiny. From now on when we are alone you will address me as
Miss Vanessa, is that clear, Jamie?"

I nodded. Another sharp pain jolted me as she again slapped my face.

"You will also feel the pain of serving me if you don't do as you're told."

"Yes, Miss Vanessa," I whispered.

"Better, Jamie, but remember in future, I don't want to hurt you too much."

She moved back from me and for the first time I paid attention to what she
was wearing. Normally she wore skirts and blouses together with her
signature stilettos. Tonight she was wearing a trouser suit, and as the
jacket was double breasted, it gave her a slightly masculine look, yet she
still wore stilettos beneath the trousers.

"Kneel, Jamie." she ordered and I slipped from the chair to my knees. "Now
close your eyes again."

I did so and felt her tie something over my eyes. I instinctively brought
my head back and received a slap for my effort.

"Jamie, you must learn to trust me. Part of serving your mistress well is
to trust that she knows what is best for you."

How quickly had I slipped to this point? It seemed only minutes ago I had
been happily staring at that damned website and now I was on my knees in
front of a woman who wanted me to be her...what? Servant? slave? I
shivered with fear and anticipation.

"Yes, Miss Vanessa."

"Jamie, I want you to remember what you felt when you looked at the
pictures on the web site. What you felt when you saw those ladyboys take a
cock past their lips and lick and caress it until it becomes as hard as
granite. Try to imagine what it is like to kiss the tip of a prick and to
wrap your lips around it and to feel that hard shaft begin to slide its way
into your throat. To feel the warmth of the cock as you worship it so that
it fills your mouth. You want that feeling, you need that feeling, you want
to serve that cock, to savour its taste and feel it move and live between
your lips. You want to feel the power of a cock as it takes possession of
you and you want to feel it twitch as you make love to it. You want to feel
the veins as the blood surges into the cock; you want to feel it slide in
and out of your mouth slippery with your saliva."

I was so caught up in the imagery she was describing that I moaned. At that
moment she slipped her finger back into my mouth and I began to lick and
suck it hungrily. She slipped the finger deeper and deeper into my mouth
until my mouth was being finger fucked. She added a second and third finger
until I felt my mouth stretch. I couldn't stop. I had to be possessed by
her. She suddenly withdrew her fingers and I felt lost. I wanted that
feeling back in my mouth. I suddenly felt something quite different against
my lips. Not her fingers. Something bigger, something far more solid than
Vanessa's fingers. I reared back but Vanessa's hands clamped around my head
and forced me back.

"Do not be afraid, Jamie. This is the start of your training."

At that moment Vanessa took off the blindfold and light flooded back into
my eyes. As my eyes came back into focus I saw Vanessa standing there
before me like a Nordic angel; long blonde hair cascading around her
shoulders but with what looked like a large penis standing proudly from her
now unzipped trousers. My eyes bulged as I took in the unbelievable
sight. She towered over me, holding the back of my head with both hands.

"Jamie, Jamie, don't worry my little girl. This won't hurt at all. Relax my
angel. Let your feelings show you the way."

Her voice was so soothing and she ran her hands gently through my hair. She
gradually drew my head towards her groin and I could see that it was some
kind of strap on dildo she must have had concealed in her trousers.

My lips brushed against the tip of the dildo and somewhere deep in my sub
conscious a small voice whispered no. My senses were reeling yet somewhere
in the midst of my confusion I knew what I had to do, even wanted to do.

The pressure from Vanessa's hands increased and the dildo began to slide
between my lips. All resistance vanished and I began to lick and suck my
way along the length of the shaft.

"Oh Jamie, that's so good baby, suck me, Jamie. You know you want to do
this so much."

Vanessa's voice seemed to come from so far away as I took more and more of
the dildo into my mouth. She began to move her hips gently and the shaft
began to move in and out of my mouth. I had surrendered myself completely
by this point. All my being was centred on what I was doing with my lips
and mouth.

"Baby, that's so wonderful. Suck my monster, wrap those lips around that
cock." Vanessa softly encouraged me and her hips began to move quicker and
the dildo moved faster in and out of my mouth.

"Look at me Jamie baby," she said and as I looked up there was the blinding
flash of a camera. "Just a little insurance baby. Not that I think I'll
need any now, do you baby?"


To Be Continued

[Transgender Stories]

Jamie's Descent Part 2

By Nikkie

"Baby, that's so wonderful. Suck my monster, wrap those lips around that
cock." Vanessa softly encouraged me and her hips began to move quicker and
the dildo moved faster in and out of my mouth.

"Look at me Jamie baby," she said and as I looked up there was the blinding
flash of a camera. "Just a little insurance baby. Not that I think I'll
need any now, do you baby?"

I was too far gone with lust and desire to even register the question let
alone give her any answer.

"That's it, baby," Vanessa purred as she snaked her hips forwards and back,
gently sliding the strap on in and out of my mouth. I could no longer think
rationally as any self control I still had slipped away and I fell into a
trance and with my eyes closed, I sucked the rubber phallus in and out of
my lips.

"Baby, you love this don't you?" Vanessa's voice took on a hypnotic tone,
gently encouraging me to take more and more into my mouth. "This is what
you want, isn't it? You want to be a cocksucker don't you? This is what
you've dreamed about, baby. This is what you were born to do."

She placed her hands around the back of my head pushing me deeper and
deeper onto the strap on. I gagged as I took nearly the whole length into
my throat and she relaxed a little to let me recover and then continued her
penetration of my mouth.

I couldn't describe what I felt as I knelt in front of my office
supervisor, my nose buried in her crotch sucking on the large black strap
on she was wearing. I felt shame, certainly, and fear mixed with a sexual
arousal so strong it was scrambling my senses. From somewhere deep in my
brain came faint messages of alarm and warning. The rush that flooded
through me as I gave myself to the woman I knelt before instantly swamped
these feelings and I felt my self-control sliding away. Incredibly, I felt
my cock rise and harden and I knew I had lost the battle with my last
remaining inhibitions.

How had this happened to me? At this moment I neither knew nor cared as I
greedily licked and sucked the rubber tool in my mouth. I had never done
this before but it seemed so right, so natural. How could something that
felt so good be wrong? Vanessa was right; I was born to do this. How had
she known? How had she seen right down to the depths of my soul?

Vanessa took her hands from the back of my head and slipped the strap on
out of my mouth. I swear she could see the disappointed flash in my eyes as
the object of my worship was removed. I felt lost without it's presence in
my mouth.

"Don't worry, baby. If you liked that, it won't be long before you feel the
real thing."

Vanessa replaced her finger in my mouth and I heard myself sigh as I sucked
it gently and gratefully between my lips.

"Jamie, things will begin to change for you now. If you don't want your
colleagues to see the pictures I took posted on the company intranet, then
you will do as I say without question from now on. Do you understand me,
Jamie?" Her tone became sharp and she lifted my chin with a finger and
locked her eyes back onto mine. I could not resist this woman who seemed to
see right through to my darkest desires.

"Do you understand me, Jamie?" she repeated as she lowered her face to mine
and I could not tear my eyes from hers. I vaguely knew that this was my
last chance to regain control. But her eyes burned into mine and I felt any
remaining resistance dissolve away and I nodded my head.

"Ye.. yes," I managed to croak.

"Yes madam!" she barked straight into my face. "From now on when others are
not around, you will call me madam. Is that clear?"

I swallowed and nodded again.

"Say it," she snapped.

"Yes, madam," I replied, realising just how much my jaw ached from the
sucking I had given the strap on.

"Good, very good, Jamie. Now I want to repay you for what you did earlier.
Stand up."

I climbed gingerly to my feet, my legs trembling from what had happened.
Vanessa took my arm and led me to the armchair that sat in the corner of
her room.

"Sit, Jamie" Her tone of voice was all I needed to make me sit down sharply
in the chair. Vanessa quickly knelt in front of me and she undid my zip and
belt with practised hands. She reached inside my trousers and she felt me
harden straight away.

"My, my, you did enjoy that didn't you, you little sissy." Vanessa smiled
as she spoke and her tongue slid across her lips. The way she said sissy
made me shiver with fear and anticipation.

"Watch, feel and learn, Jamie. I promise you will enjoy this."

Her head dropped into my lap and she took me into her mouth so quickly and
so deeply I thought I would faint. I looked down to see her head bobbing up
and down on my engorged cock and I could feel her tongue swirling across my
cockhead. I moaned with pleasure as she reached up with one hand and
stroked the base of my cock as she licked and sucked the head. I had become
so aroused I knew it would only be seconds before I came. My body tensed as
I felt the pressure build deep inside me and my cock grew even
harder. Vanessa sensed the climax and closed her mouth around my shaft. I
jerked clear off the chair and came as I had never come before and I moaned
as the cum flowed from my cock into Vanessa's mouth.

She took the load into her mouth and with lightening speed rose and kissed
me on the lips, forcing her tongue between my teeth and transferred the cum
into my mouth. Before I could react, Vanessa had clamped my mouth shut and
I swallowed automatically. I opened my eyes wide as I realised what she had
done and I began to struggle. She slapped my face hard and I stopped
moving, shocked into immobility.

"Jamie, that's only the first of many you will swallow, so get used to it."
She rose and picked up the camera, snapping more pictures of me as he sat,
now mentally and physically exhausted on the chair.

"That's enough for today my little sissy," Vanessa almost whispered almost
tenderly. "From tomorrow, you will be promoted to the role of my personal
assistant and you'll sit outside my office. I would advise you to accept
this new role...unless, that is, you want pictures I took of you tonight to
end up in everyone's e-mail."

>From somewhere I summoned the wits to nod. That wasn't enough for Vanessa,
who said, "Say thank you properly, Jamie."

"Thank you madam," I responded, my eyes downcast in abject humiliation.

Vanessa turned to her desk and took from something from a drawer. "Jamie,
my little sissy, I want you to start wearing something suitable for your
new status. These will do wonderfully, I think." Vanessa handed me a pair
of lace panties. I felt my face burn as I realised what they were.

"Oh, so sweet.. I love it when you blush, Jamie it makes you look so shy
and innocent. Yes, that's the look we will go for €“ sweet and innocent by
day and a cocksucking sissy slut by night."

I blushed again as I realised how much I liked the sound of that.

"I'll see you at 08.30 tomorrow morning and if you're not wearing those
panties I will be very, very angry." Vanessa stood there with her hands on
hips. "Now, shoo and go home you silly little girl. I need you fresh for
tomorrow."

Vanessa turned to the mirror on the wall and retouched her make up as I
left her office, but I don't think she meant me to see her smile and wink
at the mirror as I closed the door.

I don't know how I managed to get home that night. My mind was reeling from
the sensory overload I had gone through that evening. I stumbled back to my
tiny flat and I collapsed on the bed. I felt tears of shame prick my eyes
as I remembered how Vanessa had humiliated me. She had made me kneel in
front of her and suck her rubber cock, and I had not put up much of a
fight. I was a pathetic snivelling little excuse for a man.

The bitch, the bitch, the bitch. I said it over and over. Well I would show
her. If she thought she could do this to me she could think again. I just
wouldn't put up with it. I would leave. I would resign and just leave the
company. What could she do?

I had made my mind up to just not turn up the next day when I put my hand
in my pocket and found the satin panties that Vanessa had given me. It was
true they were the loveliest shade of peach and the lace trim felt exciting
as I ran them through my fingers. I turned them over in my hands and I
looked at the label - La Senza. I had often stopped in front of the La
Senza shop in the shopping centre and I remembered how turned on I had felt
looking at the beautiful lingerie in the window. Without thinking I brought
the panties up to my face and rubbed the satin over my skin. It immediately
made me remember how I had felt on my knees sucking the strap on and I felt
a frisson of excitement as my cock betrayed me as it twitched and hardened
at the memory of what I had done.

It wouldn't do any harm just to slip them on, I thought. I'm not going
through with this so I'll just see what they feel like. I stripped quickly
and stood looking at myself in the full-length mirror in the bedroom. I had
never been exactly an athletic type of guy but I had pretty good muscle
tone and had looked after myself pretty well. I ate the right things and
hadn't gone to fat like my brother.

I looked down at the scrap of material in my hand and I felt my cock twitch
again. I looked in the mirror and watched as my cock began to grow before
my eyes. I bent down quickly and put one foot and then the other into the
panties. I pulled them up my legs and the satin and lace fluttered over my
skin, sending shivers through me. He I gasped as I pulled the panties up to
my waist and as the panties cupped my cock and balls I felt my knees turn
to jelly. The satin and lace felt so light and cool €“ yet it held me so
delicately.

I turned and looked in the mirror and fell in love with what I saw. My
ever-stiffening rod tented the panties out, but I though they made me look
so pretty. I did a little twirl and looked over my shoulder and my bum
filled the panties just so. I had kept my hair long for as long as he could
remember and wore it normally tied back in a ponytail. I now shook the hair
free and it tumbled down over my shoulders. I shook my head and the hair
moved free, my whole body seemed to soften before my eyes. The angular
lines of my masculine body blurred before my eyes into soft and gentle
curves.

I was now fully erect and as I ran my hands over the satin covering my bum
I shivered and moaned aloud as I felt the material slide beneath my
fingers. I closed my eyes as my hand moved to my cock and I began to
stroke. I felt harder than I had ever been before. My cock felt like a rod
of steel. My breathing shortened and I opened my eyes just in time to see
my cock spurt for the second time that night. It was as if I were watching
someone else in the mirror as I saw the half man half girl touch a finger
to the cum stringing from the oddly familiar figure's cockhead and lift it
towards their lips. I stared as I saw the figure in the mirror lick the cum
from the finger, smile back at me and suck the finger deep into his mouth.

I knew then that I would be at my new desk at 08.30 sharp the next morning.

I had half expected Vanessa to be surprised when she turned the corner and
saw my sat at the desk outside her office the next morning. However, she
merely nodded to me as she walked up to my desk.

"Good morning, Jamie. How are you this morning? Did you have a good
evening?" she asked without even a trace of irony.

"Yes, thank you," I replied, equally deadpan. I looked around and as we
were the only ones in, added, "Madam."

"Jamie, very good. You will do very well in this new job I think. Now come
in to my office we need to organise the day's work."

I hastened in behind Vanessa who closed and locked the door. I stood in the
middle of the office as Vanessa circled me, looking me up and down several
times in a frankly disconcerting way.

"Yes, there are a few things we can start to work on straight away," she
murmured to herself. "But first, did you do as I asked, Jamie?"

She stood in front of me and looked me straight in the eye, unzipped my
trousers and slid her hand inside. She nodded in approval as she felt satin
and she squeezed my balls until I squeaked in protest.

"Good, Jamie. A very good start to our new relationship. By the way, you
will be required to work late tonight so break any plans you have for this
evening."

"Yes, madam," I wondered just what kind of work she had in mind.

Vanessa walked behind me and took off the plain elasticated band I used to
tie my hair back. She pulled my hair back and replaced it with a salmon
pink scrunchie. This time though the ponytail was fixed at my eye level;
much higher than I usually wore it. I moved my head from side to side and I
felt the pony tail swing gently behind me.

"It will make me look like a girl," I whimpered.

"Don't be silly," she said, "If David Beckham can wear it like this, so can
you."

I had to admit later as I preened in front of the mirror in the staff
cloakroom that it did look good on me. It seemed to make narrow my face,
make my cheekbones more prominent and my eyes somehow larger. I frankly
quickly got used to the swing of the ponytail as I moved my head and soon I
had forgotten it completely.

The day flew by and it was obvious that my new role wasn't that demanding
and I wondered just how Vanessa managed to get away with doing so little
work. She had gone to a lunch meeting that had lasted 3 hours and she had
arrived back looking a little flushed. I thought I could smell drink on her
breath.

The biggest problem I had to deal with all day was hiding the erections I
was getting from wearing the panties. Five o'clock came and the rest of the
office staff departed leaving Vanessa and myself alone in our part of the
office. About six, Vanessa asked me to come into her office. I again stood
in the middle of the office as Vanessa walked around me. She reached up and
took off the scrunchie from around my hair so that it fell around my
shoulders. She looked closely at my hair and pulled a face.

"We'll need to get your hair cut properly, it's a disgrace. Luckily it's
long enough to do something nice with," she moved away from me and sat in
the chair I had sat in when she blew me last night. I couldn't help but
tremble with the memory.

"Take off your clothes but leave the panties on," she ordered. I obeyed and
stood there feeling very embarrassed, not knowing what to do with my hands,
and I ended up holding them across my chest, just as a girl would do to
cover her breasts I realised.

"Jamie, your training started very well last night and will continue this
evening. Tomorrow you won't need to come in to the office, as I have made
you an appointment with our company doctor for a medical as well as a visit
to the hairdressers." Vanessa moved over to the office window and closed
the shutters so that no outside light could get in.

"Yes madam," I began to worry what would happen next.

Vanessa handed me a small box. "I want you to wear this at all times."

Inside the box lay what looked like a small gold chain. "It's called a
slave bracelet. You wear it around your ankle."

I looked closely and there was a tiny inscription `Sissy'.

"What's it for?" I asked. Innocent or stupid? I don't know even now.

"You don't need to know, just make sure you wear it all the time, is that
clear?" Vanessa's tone was sharp and I quickly bent over and fastened the
bracelet to my ankle. She took the opportunity to slide her hand over my
satin covered backside.

"So smooth," she whispered to herself.

Vanessa reached into a desk drawer and held something behind her. She moved
behind me and she asked me to put my hands behind my back. As I did I felt
a sharp pain as my wrists were cuffed together.

"What the hell?" I said, startled.

Vanessa gave me a smack across my bum with something hard and I yelped.
"Next time you swear at me it will be ten across your arse," she
growled. "I promise you will not get hurt if you behave yourself. This is
part of your training and you must learn to trust your mistress, is that
clear? There is no pleasure without some pain but if you do well then the
pleasure will truly outweigh the pain."

Chastened, I nodded. "Yes madam."

"Now, I am going to turn the lights out and it will be very dark, so don't
be frightened." Vanessa moved to the door, locked it and turned the lights
off. Immediately, the room was plunged into absolute blackness. I could see
nothing at all, and despite the warning I became very nervous. Almost
naked, handcuffed, in total blackout; who wouldn't be nervous?

I suddenly sensed a new presence in the room. I couldn't see anything but i
knew there was somebody new in the room. I opened my eyes wide but I could
see absolutely nothing, but I sensed someone moving around me in the
darkness.

"Who's there?" I croaked.

"Silence!" a male voice commanded.

I almost jumped out of my skin as I felt a hand glide across the back of my
panties.

"Be still!" the voice ordered. This was not a voice to argue with for sure.

The hand stayed where it was and began to gently rub to and fro across my
bum. I began to feel aroused as it relentlessly kneaded my cheeks. I felt a
second hand brush across the front of my panties. This hand began to rub
my swelling cock through the panties and I thought I would faint with the
sensation that was being generated. My knees began to wobble as I struggled
to contain the feelings caused by the attack on my front and rear. The
hands now moved inside my panties and I almost could not cope with the
waves of pleasure that surged through my nerve endings. I whimpered with
ecstasy as a finger slid down between my bum cheeks and probed my anus at
the same time as my cock was being stroked vigorously €“ whichever way I
moved it seemed to intensify the pleasure I was feeling. The darkness was
no longer frightening; it produced a sense of isolation in me that added to
the erotic quality of what was happening to me.

Suddenly, the hands moved away and I stood there panting, desperately
wanting the climax I had been heading towards. A hand pushed me to my knees
and I almost fell over because of my cuffed hands. The man moved in front
of me and I felt my nipples twisted and tugged by strong fingers. My
nipples had always been sensitive and I almost fainted as they stiffened
with the man's assault. The hands moved to the back of my head and as I
felt my head pulled forwards, I instinctively jerked back.

"Do not resist me! " The voice hissed out of the darkness.

The pressure continued and I felt my head slowly move forward. Something
brushed against my lips and I gasped aloud as I realised what it was. The
man's cock felt warm against my lips €“ totally unlike the cold unyielding
rubber of the night before. Almost with a life of it's own my tongue pushed
its way out of my mouth and flicked out to touch the cock. I was rewarded
with a soft "Aaaahhh" from the man. I continued to explore with my tongue
as the man held his cock in place. The cockhead felt like velvet to Jamie
as my tongue lapped and slid across the surface. The man pulled again at
the back of my head and I opened my lips and allowed his hard cock to enter
my mouth.

This felt completely different from the previous night. Then the phallus
was cold and lifeless; a pathetic substitute for the object I now held
between my lips. This was the real thing. I could feel the veins standing
out from the surface and felt the cock twitch as it slid deeper into my
mouth. I could feel the heat and I could smell the man's odour as well €“ an
aroma of pure masculinity. Although this was the first time I had ever held
a cock in my mouth I remembered what Vanessa had done last night and began
to move my head up and down the shaft. I gagged once or twice, and the man
sensing my inexperience pulled back to allow me to recover. Once, I brushed
the cock with my teeth and the man hissed in anger. Despite my inexperience
I quickly found a rhythm and slid my mouth along the length of the shaft,
once feeling my nose graze the man's pubic hairs. Despite my lack of skill
the man moaned once or twice so I guessed I was doing OK.

I began to feel I was dreaming. As if in an out of body state, I felt
myself rise above my body and look down on the scene below. I saw myself,
naked except for a pair of satin panties, kneeling with my hands bound in
front of a tall well built man. The man had his hands round my head and he
was pushing his large hard cock in and out of my mouth. I watched as the
man tensed and approached his climax, moving his cock faster and faster as
the moment of release approached. I heard the man gasp and saw his knees
sag slightly as he came and I watched with detached fascination as the man
climaxed. I saw myself suck the cum eagerly from the man's cock and swallow
greedily. I watched as the man withdrew his cock, saw him wipe his cock
casually across my face and saw myself smile as I licked my lips to collect
the last of the cum that had spilled from my mouth.

I had found my destiny.

[Transgender Stories]

Jamie's Descent Part 3

By Nikkie

The limousine took me to Harley Street, home of the UK's private health
industry, for the medical Vanessa had mentioned. To me it had seemed less
of a medical and more of a preparation for something. There were a lot of
the usual blood pressure tests and urine samples, but there had also been a
lot of measurements taken, especially around my upper body. The doctor and
nurses were efficient though and seemed satisfied with my overall
condition. I had felt the doctor spent a little too long on what he had
said was the prostate check. The doctor's finger seemed to spend a long
time probing my rectal area and it reminded me acutely of the way the
mystery man had touched me the previous night. I felt sure the doctor had
seen the way my cock had reacted to the examination by swelling
considerably. It had been a little embarrassing to explain to the nurses
why I couldn't take off the ankle bracelet, but they seemed to take it in
their stride. The doctor said that I was a little out of condition and
prescribed a course of supplements, with orders to take them once a day and
a repeat prescription for when they ran out.

My next appointment was for what Vanessa had described as `a visit to the
hairdressers'. The limousine weaved through the London traffic to an
address in Covent Garden that turned out to be a very upmarket beauty
salon. The receptionist had obviously been expecting me and as soon as I
had given my name I was whisked away to the rear of the salon. A blonde
with a stunning figure barely contained in white t-shirt and shorts
approached me and introduced herself, "It's our pleasure to have you here,
Jamie. My name is Lisa and I'll be taking care of you today." Handing me a
pure white silk wrap, she said, "Just take off your clothes and slip the
wrap on and we'll get started, it's going to be a long day for you."

"But I'm only here for a haircut," I pleaded. Lisa must have been almost
six feet tall and she towered over me. She had a flawless complexion and
the kind of toned look that can only come from working out every day. She
looked as if she had come straight from a Californian beach. Her long
blonde hair framed a perfectly tanned face as she looked sternly down.

"I have my instructions personally from Vanessa and she has been very clear
about what you need, so don't worry about anything. We won't bite. You'll
love what we do to you here,"

Another girl joined Lisa, this one a black girl about the same age as Lisa,
as tall and as dazzlingly beautiful. Lisa introduced her as Fiona and said
they were going to work together on me. Fiona's hair was pulled straight
back from her face and tied back in a topknot. She exuded an air of wild
and uninhibited sexiness. The contrast between the two girls was
extraordinary and I felt so tiny beside these two gorgeous and exotic
creatures. The two girls stood waiting as I hesitated, thinking they were
going to leave so I could take off my clothes.

"Come on, don't be shy," said Fiona, breaking the awkward pause, "There's
only us girls here."

I felt that remark to be ambiguous but before I could say anything Fiona
had started to undo my shirt and Lisa had grabbed my belt. As my trousers
fell to the floor the new pair of panties that Vanessa had given me to wear
became clearly visible and I blushed crimson.

"They're a lovely colour," Lisa remarked immediately. She ran her hands
over the silk material saying, "And you fill them out so nicely. Don't
blush my dear, you look divine in them. Why don't you keep them on?"

Fiona helped me into the robe and whispered in his ear, "Don't worry honey,
we have lots of male clients who like to express their feminine side. I
like that." As she said this, her hand seemed to brush across the front of
my panties and she held my eyes for a long second. . Lisa broke the
spell, "Later, Fiona. We have work to do now. Let's make this little cutie
even more beautiful."

I was about to protest about being described that way but Fiona gave me a
quick peck on the lips and said, "OK, but I want the first ride on this
little pony."

The silk robe felt so light and cool and, well, feminine. They also made me
slip on a pair of white mules, which took a few minutes to get used to, but
which then felt incredibly comfortable. I began to feel slightly light
headed at the attention I was receiving from these two beautiful girls. I
was led into a second room and shown to a reclining chair flanked by tables
filled with small bottles and jars. The two girls spent some time examining
notes on a clipboard leaving me to examine my surroundings. I gradually
became aware of the wonderful mixture of aromas in the room, and together
with the soft ambient music playing in the background I began to relax
properly for the first time since Vanessa had caught me looking at that
website. I couldn't believe it had only been three days ago that Vanessa
had called me into her office. How could my life have changed so much in
such a short time?

The music and scent in the room lulled me deeper into a daydream and I
recalled the day my brother had shown me the grainy photograph of the Thai
ladyboy sucking his cock on the rugby trip to Bangkok. Had that been the
real start of this journey? I remembered how strangely I had felt when I
had seen that photograph. What I now also remembered were the dreams that
had followed that day. Dreams in which I had become the ladyboy in the
picture, sucking my brother's cock until his cum dribbled from my lips.

I shivered as deeply buried memories drifted into my mind. The time when I
was about five and some older girls at my primary school had adopted me as
their living doll. They had managed to dress me one day as a girl with
ribbons in my hair and one of their old dresses. They had practised their
make up skills on me until one of their mothers had come home.

A memory of when I was a little older came jostling through. I was eight
years old and my mum had caught me trying on her stockings and had made me
wash her underwear for a week as a punishment. I remembered the feeling of
the silks and satins of her lingerie on my hands as I gathered them from
the clothes hamper ready for the wash. I could now see myself as I held my
mother's knickers to my face and I could still smell the scent of my mother
on her underwear.

Later, at secondary school, I remembered a crush I had for an older boy at
the school. The boy had seemed flattered by my attention and I smiled as I
remembered the day we had cut school and gone swimming at the beach. We had
changed behind the sand dunes and I had watched as the older boy's towel
had dropped while he was changing and had been rooted to the spot as I saw
the boy's cock for the first time. It looked so long and thick compared to
mine. The beach was deserted at that time of year and when we got into the
sea, the boy said, "Lets go skinny dipping." He dropped his own swimming
shorts and made a grab for mine. I put up a fight, but only because I
wanted to wrestle with the boy in the water. He eventually overpowered me
and I felt his hands graze my cock as my shorts were dragged down. I chased
the boy through the waves and we play fought each other as the cold North
Sea surf rolled off us. The waves pushed us into the shallows and the boy
somehow ended up lying on top of me, pinning me to the wet sand. I could
feel his large stiff cock rubbing against my own smaller one and I vividly
remembered the boy's lips slowly descending towards mine, when somebody
shouted, "Oi, what you doing. You dirty little buggers!"

We ran off laughing at the old man walking his dog, but soon after, the boy
moved to another school and quickly stopped answering my letters.

"Jamie! Jamie! Wake up sweetie." I felt someone gently shaking my shoulder
and I opened my eyes to see Fiona's face only a few inches away from
mine. "Judging by the smile on your face that must have been some dream,
honey."

Her eyes were an incredible hazel colour and I couldn't stop myself saying,
"You have such beautiful eyes."

"Why thank you honey," she smiled wickedly as she whispered, "I have some
other things you might like too." Her hand snaked through my wrap and
squeezed my cock through my panties. "But as aunty Lisa said, that's for
later, my sweet little angel." I squirmed in the chair, feeling the silk
slide sensuously over my skin. Fiona winked as her fingers kneaded my
cock. I felt myself harden under her touch.

Lisa interrupted by saying "Let's get started Fiona. Waxing first, I
think."

I sat bolt upright. "Waxing? No-one said anything about waxing. I'm not
having that." I tried to get out of the chair.

Lisa calmly and effortlessly pushed me back down, "Vanessa said you might
be a little bit reluctant, so she gave me some pictures to show you that
she felt would change your mind." Lisa handed me some photographs and I
groaned as I saw what they were. Some were from that first day in her
office showing me sucking on the strap on protruding from her trousers. A
few were from the second time with me standing in the middle of her room,
wearing only the panties.

I sank back, defeated, and sighed, "Lisa, OK, you win. I'm yours."

"And mine later," grinned Fiona.

Fiona helped me out of the wrap and I stood there naked in front of these
two gorgeous women. I must have been losing my inhibitions because although
I didn't know where to put my hands I was not feeling so embarrassed.

To tell the truth I had never grown much body hair so it wasn't as painful
as it might have been. But, even so, it was a huge relief when the girls
had finished. I had really objected, however, when they moved to my pubic
hair and in the end Fiona had used a small electric trimmer to give me what
they called a brasilian. As Fiona finished she grinned evilly, "Next time,
honey, it's the wax!"

I couldn't see what they had done properly because there were no mirrors in
the room, but my skin felt really smooth and I could look down and see a
small strip of my pubic hair leading down to my cock. I had taken off the
panties before the waxing and when I came to put them on again they felt so
smooth against my totally hairless legs. A pedicure and manicure came next
and while they worked on my nails Lisa popped a pair of headphones on my
head. I closed my eyes and let the music carry me away. It felt so good to
have two pairs of soft hands caress my fingers and toes as the girls worked
on me.

I had achieved a deep state of relaxation when I felt a sharp sting in my
right ear. "Yow," I squealed and yanked off the headphones, "What was
that?"

"I've just pierced your ear, nothing to worry about," said Lisa. "Now just
hold still."

"Yow," I said again as she did the left ear, "That hurt."

"Don't be a baby," said Fiona, "Or I'll have to hurt you properly later."
Fiona was starting to scare me a bit.

Lisa slipped some small sleepers into the holes and I rubbed my ears. "Next
time we'll pierce your belly button. That will look so cute." said Lisa.

I ignored the remark and glanced down at my hands. My nails hadn't been
long enough to shape properly but they did look different. Lisa saw my look
and said, "We've done our best and given them a little colour. Just let
them grow and we'll keep shaping them for you."

"But I won't be coming back." I blurted out.

"Oh, I think Vanessa will make sure you do." Lisa said gently. I wondered
how well Lisa knew Vanessa. I smiled broadly as I formed a picture of Lisa
on her back being shagged royally by Vanessa wearing the same strap on I
had sucked.

There was a pale pink colour on my fingernails that was just visible. I
began to worry about what people at work were going to say at work. My
toenails had been done in the same colour and I wiggled my toes and they
looked so pretty. I saw Lisa and Fiona exchange a small smile as they saw
my delight.

"What?" I asked.

"Nothing," Lisa said, "only that Vanessa will be very pleased with your
progress. Sometimes it takes much longer than this to get to this stage."

I was so fascinated at looking at my newly coloured nails that the remark
really didn't register. I splayed my fingers out and let the light play
across the fingernails. Fiona giggled.

"What this time?" I said.

She smiled and said, "When men look at their nails they normally curl their
fingers over in a fist. Girls spread their fingers out like you just did."

"That's ridiculous," I said, but immediately put my hands behind my back.

"Too late, honey," she whispered. "Don't worry; it will be just our little
secret."

Lisa pushed me down into the chair and took off the scrunchie that held my
hair in the ponytail. She brushed it out with her fingers, all the time
making disapproving noises with her mouth. "Tsk, whoever did this needs to
be shot," she muttered. "Mmm, lets see what we can do now and hope that we
can tame this jungle eventually."

Swiftly and efficiently, Lisa worked on my hair. There were no mirrors in
the room so I couldn't see what she was doing. It was strangely flattering
to have these two goddesses concentrating solely on me and I felt more and
more comfortable in the role that was being created for me. There was
something deeply soothing yet exciting in the way Lisa first washed my
hair. I lay backwards with my head on the sink and I felt dizzy with the
feeling she created as she stood over me gently working the shampoo through
my hair. Lisa occasionally asked Fiona her opinion as she cut my hair and
the two of them seemed pleased with what they had done.

I began to crave to see what the girls had done and I dared to hope that
Vanessa would be really pleased with the way I looked. I unconsciously
crossed one leg over the other and thought how smooth and nice my legs
looked now. I found myself staring at Fiona as Lisa worked on me. Fiona
noticed me looking, moved closer to me and began to stroke my leg with her
long dark fingers. She brushed her fingertips along the inside of my thigh
getting closer and closer to my cock which for about the tenth time sine
I'd arrived was as hard as a rock. I wriggled in the chair as she brushed
my silk covered cock with her fingers.

"Fiona, stop it. You're making her move so much I might just cut her ear
off," said Lisa.

I stopped moving, but Fiona didn't stop her teasing and I felt faint with
frustration as she built me towards a climax, and then slowed the pace of
her fingers.

Lisa eventually finished with my hair and both girls professed themselves
happy with the result. At this moment Fiona took over and led me to a table
covered in make up. Fiona sat me down facing her and she began a careful
examination of my face.

"How often do you shave, honey?"

I had never had a strong beard growth and I guess I only had to shave
lightly every three or four days. I told her this and she seems happy
enough. The next half hour she spent working on my face, massaging my skin
and then using what seemed an endless series of creams and lotions on my
face. Several times she asked me to close my eyes and I felt her gentle
touch applying things to my eyelids.

I relaxed and kept my eyes closed as she worked until I felt a sharp sting.

"ooowww". I said, startled by the pain.

"Don't panic, my little sissy." Fiona smiled as she spoke, "I'm only
plucking your eyebrows. It will make you look so sweet."

She went on with this for a few minutes and I swore I would never have that
done again. She finished and then move on to my lips. It felt so feminine
to have her paint my lips and it gave me the chance to look at her closely
as her face was so close to mine.

"Do you like what you see, baby?" she asked without pausing.

"Mmm, yes,"

"Good," she said, "I like what I see too."

"That should do for now," said Lisa. Both girls stood back and smiled as
they surveyed the effects of their work.

"Let me see, let me see," I simpered.

They turned my chair round and removed a towel that had been draped over a
mirror in the corner of the room. I looked into the mirror and simply could
not believe what I saw. Looking back at me was the face of a young girl,
blonde hair falling down to her shoulders. I moved my head and the head in
the mirror moved too, the hair gently swinging with the movement. I smiled
and I could see the girl smile back. I sat stunned. I couldn't believe what
I was seeing.

"Do you like what you see?" asked Lisa.

I still couldn't speak, but I managed to nod my head.

"We'll take that as yes, then," laughed Fiona.

Lisa turned to Fiona. "I think you've earned the first crack at this one,
Fi."

Fiona's smile was one of triumph and naked lust. I shivered with anxiety.

Lisa noticed and softly said, "Don't worry, Jamie baby, Fiona won't do
anything too nasty. This time."

Fiona laughed and Lisa walked across to her, wrapped her arms around Fiona,
one hand in the small of her back and the other behind her head. Lisa drew
Fiona close to her and I saw Fiona's eyes shut as she placed her hands on
either side of Lisa's face. Their lips touched and the girls' tongues
snaked from their mouths and began to fence with each other. Lisa's leg
moved between Fiona's who gave what sounded like a growl as I saw her
tongue disappear between Lisa's lips. The girls kissed deeply for several
minutes, their hands running over each others bodies.

I was riveted to the spot. It seemed I had almost stopped breathing as I
watched the Nubian princess and the Viking queen entwined before me. I
could feel my cock rise at the unbelievably erotic tableau in front of
me. Lisa finally broke the embrace and smiled wickedly at me, "Jamie, this
is part of your education, so pay attention to what Fiona does; I promise
you'll enjoy it."

My tongue had somehow got stuck to the roof of mouth and all I could do was
nod dumbly in reply. She let her fingertips slide over the front of
Fiona's tunic through which her nipples had suddenly become very
visible. Lisa let her fingers rest on one nipple and suddenly tweaked
it. Fiona moaned and her eyes blazed with desire.

Lisa walked towards the door and turned as she reached it, smiled wickedly
and said, "Fiona, don't forget now, play nicely."

"Oh, don't worry babe, I'll take very good care of her," Fiona replied,
looking me straight in the eye.

I felt like a rabbit caught in the headlights of a car as I sat and watched
Fiona close the door after Lisa and pocket the key.