SUDDENLY SOPHIE
By Charlotte
This story contains scenes of an erotic nature and is not intended for
minors. Further, if such material is considered illegal in your area, you
should by bypass this story. This story remains the property of the
author. Permission is granted to download, photocopy, copy and re-post as
long as any such action contains these disclaimers, and no attempt is made
to profit from this story.
Today is my wedding day. The ceremony doesn't start for ninety minutes but
I am already wearing my dress. It is ivory silk with a full-length skirt,
tight bodice and puff sleeves. When I saw it in the shop I knew I had to
have it. It's just gorgeous and makes me feel like a princess. I'm also
wearing a very tight cream corset, matching french cut panties and
stockings. My shoes are so delicate and feminine, 3" heels with just two
thin straps securing them to my ankle. I often wear much higher heels but
I will be on my feet all day and I don't want to get tired. I sink back
into the chair behind me and finger the tiny scar on my neck where I had
the operation. In order to get at the scar I have to push up the thin
metal collar I wear all the time now. Miss Rachel was kind enough to make
the collar loose fitting so it is easy to move. I run my long red nails up
and down my body, hardly daring to believe today has come. My artificial
breasts strain against their layers of silken constraints as I think back
over the events of the last 2 years and my little sissy clitty starts to
stir in its metal prison.
Miss Rachel has promised that if I am good today she may even remove my
chastity belt tonight. I am resolved to be as well behaved as I can and
really make her proud of me. I hated that thing when she first put it on
me but I now understand the reasons she had to do it. It is frustrating
and sometimes painful not to have control of my own pee-pee but I have
accepted that it belongs to her now. Also, wearing the chastity belt has
made me so much more compliant and feminine. When she first told me we
were to be married I was apprehensive. When she explained that I would be
the one wearing the dress and I would have to promise to obey her I was
downright scared. The fact that she put me on a crash diet so I could fit
into the costume she wants me to wear for the entertainment at the
Reception didn't help. Gradually I've come round to the idea. It's a
shame my parents have refused to attend but I know if they did come they'd
only create a scene. No, today must be perfect. It's my chance to
demonstrate to the whole world the commitment I've made to Miss Rachel. I
lean back in my chair, close my eyes and think back to how it all started.
It all started two years ago because it was Friday night and I was bored
and there was nothing on television. I was an 18-year-old kid who had just
started university. My parents were rich and when they first suggested
buying me a flat I thought it was a great idea. Unfortunately I was
finding out that living on your own made it a lot harder to make friends.
For the last few years my parents had paid to send me to private school.
On the surface I was a normal schoolboy, missing classes and drinking at
the weekends whenever I got the chance. However there was one big secret
nobody knew about. For years and years I had fantasised about dressing in
girls clothes. Of course I never did anything about it, I was much too
much of a wimp and my parents would have died of shame if they found out.
I just fantasised endlessly about dressing like my sisters and doing all
the things I saw them doing.
Today was different though. Earlier this afternoon I had bought a computer
and I just installed the ISP software. I was hooked up and ready to
connect to the internet for the first time in my life.
I had read about chat rooms in the newspaper and wanted to see what they
were like. The first thing I did was head for Yahoo because that was the
only one I had heard of. It took me a moment to download their software
and work out what was happening and then I was away. I choose the first
name that came into my head, 'sissy'. I didn't bother to fill in the
profile; I just wanted to get on line as soon as possible. After I found
the adult rooms I surfed around a bit, generally being ignored. On one
level it was very strange, these people were thousands of miles apart
pretending they were in the same room. On another level it was strangely
erotic, I found myself watching Hercules dominating his sub pretty_flower
by forcing her to pretend to give him a blowjob in the middle of the chat
room.
Suddenly a message box popped up in the middle of my screen,
'Busy slut?'
I looked at the top of the box, it was sent by 'Cruel_Master_James'.
A few seconds later another line appeared below the first one.
'I asked you a questions slut'.
I panicked. I moved my mouse instinctively and killed the connection.
Instantly I regretted it. What was I doing? I couldn't wimp out again.
For years I had fantasised about discussing my yearnings with like minded
people and at the first chance I had I wimped out.
Eventually I reconnected and found the chat site again. This time I
decided to go for a more descriptive name and set up a profile as
'male_sissy_maid'. I typed some rubbish into the description about how I
liked to dress from time to time and go to clubs. I also found a S&M site
and borrowed a picture of a very thin man dressed as a secretary in a
blouse and tight pencil skirt, wearing a dog collar and chains and kissing
the thigh boots of a blonde sex goddess dressed in an all in one PVC
catsuit.
I soon found a room called 'Slut TV's in a dark alley' and decided to take
a look. It was full of people but it was clear most of them were engaged
in private conversations and I couldn't find anyone to talk to. The few
that did want to talk were only interested in my telephone number. After
about fifteen minutes I was about to leave when a private message popped up
on my screen.
'Interesting photo. Is it you?'
I looked at the name - 'Hercules'. Hmmm.....he was clearly going to be
disappointed by the truth so I decided to lie.
'Yes Sir'.
'You're very pretty slut. Tell me about yourself'.
That was all the excuse I needed. For the next 30 minutes I chatted with
Hercules. It was only later I realised I had told him all sorts of things
about me but had learned absolutely nothing about him. It didn't seem to
matter; I was overcome with relief at being able to talk to someone about
my inner desires with no fear of ever meeting them. The little white lies
I told along the way didn't seem to matter; when Hercules asked me what I
was wearing I told him a tight black leather mini, blouse, stockings and
spike heels. He encouraged me along the way, asking what turned me on, how
I saw myself.....it was kind of like talking to a kinky psychiatrist.
Eventually he asked if I wanted to be placed under his guidance. I nearly
came when I heard that. He wanted to help me fulfil my innermost dreams
and desires. I had only been online for an hour or so and here was someone
offering to do exactly what I wanted.
Immediately I said yes a change seemed to come over Hercules. He insisted
I sent a message in the open room begging to be allowed to serve him. He
pretended not to be interested and replied telling me to crawl towards him
on my hands and knees. Then he asked me to tell everyone how I was
dressed. My cheeks were red and my little sissy cock was straining as I
read the comments from some of the other people in the room. It looked
like they were used to this sort of thing!
With feigned reluctance Hercules eventually said yes. He asked me what I
was wearing again and when I gave the same answer he told me to go and get
a length of rope. As fast as I could I ran into the hall of my flat and,
kicking off my clothes, came and sat down again in front of the computer.
I was now stark naked. I typed out a message;
'I have done as you ordered Sir'.
'Good slut. First remove your skirt and panties. Then take one end of the
rope and tie it around the base of your cock and balls. Pull it to make
sure it's tight. Then thread the rope between your legs, loop around your
waist and tie it off. I want your TINY little cock hidden between your
legs. Then put your knickers and skirt back on.'
I looked at the screen. Hell! That was going to hurt. Strangely, I never
thought of disobeying. Hercules was probably thousands of miles away but I
felt like he was in the room with me ordering me to do this with the crowd
egging him on. There was no way I could do anything other than he ordered.
Submission came naturally to me.
Very gingerly I looped the rope around my ball sac and pulled tight. I was
right, it did hurt!
I typed out a message telling him I had obeyed. Suddenly I heard a single
voice coming out of my speaker. Dimly I wondered why I hadn't noticed this
room had voice chat as well.
'Let's see if the sissy is any good at sucking cock Hercules'.
There was a gaggle of laughter. The message from Hercules was clear
enough.
'On your knees slut'.
Without thinking about it I slipped off my chair and fell to my knees.
This man was thousands of miles away from me but the instinct to obey was
so strong that I never considered doing anything else. I found my eyes
were half closed and my lips pursed almost as though I was ready to receive
his penis in real life. Without thinking about it I started to type. To
this day I can't remember much but I could almost taste a strong musky
smell in my throat. On one level it was absurd, I was pretending to have
oral sex with this man who wasn't even in the same country to me. To me it
seemed perfectly natural however, I was so ready to give myself to anyone
who noticed me.
I had had a few girlfriends and one in particular who enjoyed the taste of
my cum. I thought back to what she had done and what I had enjoyed.
Gradually I relaxed, words like 'moist lips' featured a lot. The rest of
the room obviously enjoyed the entertainment; there was a constant stream
of comments from my loud speakers. Eventually Hercules came, turning his
microphone up loud so the whole room could hear. That wasn't the end of my
performance however; I spent the next 2 hours sucking off every other male
in the room under his direction. Time seemed to pass quickly, I was
totally immersed in trying to please Hercules. Finally I saw him type out
a message.
'I am going now. I hope you all enjoyed today's entertainment'.
Quickly I typed out a reply.
'When will I see you again Master?'
For the first time I heard Hercules's voice, a low chilling laugh in my
speakers.
'See me again? You really believed I am interested in owning you? This
was strictly a one night stand sissy. Crawl back under your rock, there
are thousands like you begging to serve me everytime I log on'.
I was numb. I heard the rest of the room laughing at the way I had been
used. Used and thrown away like the pathetic sissy I was. How could I
complain? Wasn't this exactly the treatment I had begged for? My little
sissy clitty was straining. Remembering my manners I was polite to the
last.
'I hope my service was satisfactory Sir'.
I logged off with renewed laughter ringing in my ears.
I slept late the next day. When I got up I didn't even look at the
computer, after a late lunch I went out to do some food shopping. It was
late in the afternoon before I had put everything away and I decided to
have a quick look on the internet to see if I could find out what was on TV
that night. Almost as soon as I logged on I saw a little envelope icon at
the bottom right of the screen. When I clicked on it an e-mail inbox
appeared. This was strange, I hadn't signed up for an e-mail account yet.
Then I saw the name at the top of the screen, 'sissy_male_maid'. I
realised the account must have been automatically created last night when I
used the chat room. I had been so upset I hadn't logged out so the
computer had retrieved the messages for me when I logged on again.
There were two unread e-mails; the first was the traditional 'Welcome'
message. The second was more interesting. It was from someone calling
herself 'Mistress Rachel' and was headed 'You'. I double clicked to open
it.
'Sissy
I was in the chat room yesterday and saw your display for Hercules.
Although it was clear you have little experience I was impressed by your
obedience and natural subservience. To the end you treated your Superiors
with the respect that is their due. I am not going to try and defend the
way Hercules used you, however you clearly understood that it is not for
sissies to question their Superiors and continued to display the
appropriate dignity and deference.
I would welcome the chance to talk with you further, although I appreciate
that after your experience yesterday you may have reservations. If you are
available I will be on line tonight at 17:30 UK time. It would please me
if you were there.
Regards
Mistress Rachel'
I felt light headed...this was a real Mistress. She wanted to talk to me!
Suddenly I glanced at my watch. Hell! It was 5:23 already. I had 7
minutes.
Frantic now I jumped up from my seat and pulled the curtains shut. I fixed
myself some sandwiches and a drink, took them out to the computer and then
checked all the doors and windows were shut. Before logging on again I
stripped off my clothes. Looking at the clock on the computer I saw I had
less than sixty seconds left.
She was waiting for me. As soon as I entered the chat room a message box
popped up;
'Welcome sissy. I'm glad you could make it'.
Suddenly I was incredibly nervous. What was I doing?
'Thank you Mistress. Ummm........thank you for your e-mail'.
'Welcome dear, but please call me Miss Rachel. Your performance last night
fascinated me. You showed a lot of potential. I wanted a chance to chat
with you'.
For the next three hours we talked. Just talked. Miss Rachel asked me
about my background; my fears and desires, hopes and dreams. I was as
honest as I could be but still maintained the rubbish I had typed into my
chat profile yesterday was true. I didn't feel able to tell her I had
misled her so early on. All the time she quietly encouraged me to open up
until I heard myself telling Miss Rachel things I hadn't realised myself.
I explained my constant dreams and fantasies where I always played the role
of the submissive sissy and the effect this had on me. When I told Miss
Rachel that my name in these fantasies was always Sophie she graciously
agreed that I could keep that name. She began to tell me a few things
about herself, I learnt she had trained a number of real life sissy maids
in the past but currently did not own any.
She told me a number of stories about how she had humiliated her girls.
Each story turned me on more than the last and I knew beyond doubt that
this was the life for me. When I heard her final story about how she had
punished a slave who had been masturbating without permission by dressing
her like a slut in a tiny red miniskirt and red PVC thigh length high
heeled boots and dropping her in a town 80 miles away in the middle of the
night my little sissy clitty felt like it was about to explode. The girl
only got home by hitching a ride with a trucker. She spent the entire ride
kneeling in front of the driver with his penis in her mouth. This was a
whole new world to me and I knew then that I wanted it more than I had ever
wanted anything.
Eventually Miss Rachel told me she had to go. I asked her when we would
chat again. Her answer shocked me;
'Never, unless you learn to be honest with me.'
'I don't understand. What do you mean?'
'Well - for a start that picture on your profile isn't you, is it?'
Even though she was many miles away I turned beet red.
'Ummmm.....no. I am so sorry Miss'.
'You will be. Understand this, I will not tolerate any form of
disobedience or lying. Being a good sissy takes dedication and self
sacrifice. It will take over your life, it is not just something to play
at on the weekend. I will be here at the same time in 2 days. Think
carefully. If you want to see me again I have some tasks for you to
complete in the next 48 hours.'
'Anything Miss. I am just so sorry to have disappointed you'.
'Hmmm....well. You have 48 hours to prove that. You've already told me
you have plenty of money, now you will spend some. I want your profile
updated with TRUE information and a real picture of you. Buy a digital
camera and scanner if you have to. From now on I want you properly dressed
every time we meet. Go out and buy yourself a wardrobe; skirts, dresses,
lingerie, shoes but NO pants. No flat shoes either. Don't forget the make
up, it's so important for sissies to be well turned out.
Finally - and this is most important - you are to get yourself a webcam and
microphone. I want to be able to see you and hear you. I'm not wasting my
time typing out messages, if you have any doubts you should tell me now.
That's a lot to remember for an airhead like you. Do you have it all
dear?'
I could only stare at the screen. When I started down this path I had no
idea how far I would go but in my wildest dreams I never imagined this. The
idea of finally having my own wardrobe thrilled me and yet terrified me at
the same time. The idea of someone else seeing me dressed really terrified
me! Yet, I could stop this at any time. She hadn't asked for my real name
or address. I could experiment by obeying her and then just delete my
profile later and stop logging on if I needed to. I wanted to obey Miss
Rachel so much. I had spent most of my life wimping out, there was no way
I was avoiding my fantasies again. I gave the only answer I could.
'I understand perfectly Ma'am. I will be here in 2 days'.
Looking back I wonder why I never thought of arguing with her, asking for
more time before taking such a big step. I think it was because I could
not disappoint Miss Rachel again; I had to prove myself worthy of her
attention. In the short time I had been with her I had subconsciously
accepted her as my Superior and her approval was increasingly important to
me. In fact, her approval was becoming the only issue of importance in my
life.
The following morning I skipped college and drove to a large town about 80
miles away. The computer equipment was easy, I just went straight to the
local branch of Dixons. The clothes were more difficult, it was
horrendously embarrassing just to walk into Dorothy Perkins. The first two
times I tried I turned such a vivid shade of red I left before a sales
assistant threw me out. After an hour I nearly had a crying fit when a
grandmother out shopping with her granddaughter pointed at me and said
'That's a pervert dear'.
I managed to buy a few things and eventually decided to go back to my car
and drive into London. It seemed to make things easier, there were more
people in the shops and even some men shopping for wives and girlfriends.
It was still embarrassing, one shop assistant insisted on holding up a
short black velvet dress to see if it would fit when I tried to buy it.
Eventually I had enough clothes to please Miss Rachel when I chatted with
her again, I resolved to buy the rest from mail order!
The only thing I hadn't managed was shoes, clearly no shop assistant was
going to allow me to try on high heels and from what I saw of the sizes
they all looked a bit small for me anyway. Eventually I had a stroke of
genius, I took the Tube over to Kings Cross and went to a transvestite shop
I had seen before in the run down area behind the station. Once I got over
the initial shock of seeing so many other guys like me shopping for girl's
clothes it was quite easy. I ended up buying one pair with a four inch
pencil heel and wrap around strap and one pair of ankle boots with a wider
five inch heel.
It was nearly midnight when I got home and I was exhausted. I really,
really wanted to try something on but I just lay down on my bed first for a
quick rest. I closed my eyes just for a second, the next thing I knew I
was awakened by the sound of cars in the road outside. I looked at my
watch, it was 10:00AM. I had slept right through past the alarm!
Resolving to make the best of things I decided to spend the day pampering
myself.
After calling into college to take another day off I ran a lovely hot bath,
using some scented oils. While in there I shaved every inch of my body
below my neck. After climbing out of the bath I dried my hair into what I
hoped was a feminine style and sat down in front of the mirror to do my
makeup. I had no experience of using makeup before so my first few
attempts were a bit of a disaster. Far too much rouge, blusher and
mascara. After about half an hour I learnt to go easy on the blusher and
mascara and managed a half way respectable look. It was still a bit tarty
but at least I didn't look like Barbara Cartland.
It was a real shock to look in the mirror and see this feminine face
attached to my body. I ran my hands up and down my smooth body, revelling
in the submissive and feminine feelings that overtook me.
After a few seconds I picked up the bag from Knickerbox and dropped my new
lingerie collection onto the bed. When I was in their shop yesterday I
pretended to be shopping for my girlfriend, everything I bought was silk or
lace and very, very delicate. I picked out a matching bra, high cut
panties and suspender belt in cream silk, my poor little penis was rock
hard as I slid the panties up my legs. It took me a few minutes to get the
stockings on properly, I loved the sensation as they pulled against my
suspender belt when I snapped them in position.
I routed around the pile of clothes on my bed and decided to wear the black
velvet dress. The skirt was tighter than I thought and my painfully stiff
errection was forcing it out into a tent. Eventually I managed to reach
round and pull the zip up, I couldn't help but run my hands up and down my
new body. After putting on my new 4" heels I practised walking across the
room a few times to get used to them. It was the first time I had ever
worn heels and I nearly broke my ankle a couple of times. Soon I was
swinging my ass as I'd seen the girls do down the pub on a Friday night and
it all became much easier. After about 10 minutes I had forgotten I was
wearing them. I caught sight of myself in the mirror and had to stop for a
double take. I was gorgeous! I'd never really had much luck with the
girls, my body wasn't really up to much. I'd been transformed into a sexy,
sassy young woman of the sort I lusted after on the infrequent occasions I
went to nightclubs. I'd never felt like this before, so vulnerable and
feminine. All my doubts had gone, I knew I could pass as a girl and I
loved the way it made me feel.
I had about 2 hours until my appointment with Miss Rachel. I didn't have
the courage to go anywhere so I sat down to watch some television. I had
bought some long red false nails yesterday so I busied myself attaching
them to my fingers. It was so strange to be sitting there watching 'This
Morning' and playing with my vampish red nails. I even found myself paying
special attention to the beauty items, wondering how the makeover was going
to turn out and what I would look like in the ridiculously short skirt they
had put their middle aged victim into. As my appointment with Miss Rachel
drew nearer I became more and more nervous, getting up to pace the
apartment and reassuring myself by checking my appearance in the mirror.
About forty minutes before my appointment I suddenly realised I needed a
feminine voice. There was no way I could use my normal voice, dressed as I
was! The whole experience was already going to be extremely humiliating.
Luckily my voice was quite high, I started with this high pitched squeak
rather like Minnie Mouse but soon graduated to a lower Bette Davies tone I
felt I could maintain reasonably consistently. It was weird hearing this
odd voice coming out of my mouth, I practised by reading items out of a
magazine until I could manage two minutes without changing my pitch.
Eventually it was time and I logged on. I saw the icon indicating Miss
Rachel was already there so I raised my trembling hand to turn the webcam
on.
The screen flickered for a few seconds and then the colours began to form
to reveal this gorgeous woman. It sounds like a clich' but the first
thought to register in my mind was that Miss Rachel was stunningly
beautiful. She was in her late twenties, slim with shoulder length blonde
hair and largish breasts. She was sitting down wearing this very tight red
wrap around dress. Her eyes were green and the most piercing I had ever
seen. They appeared to be staring right at me. Behind her I could see
some French Windows and a neatly kept garden. Then I saw her face light up
as she began to smile. I realised she could now see me as well. At that
moment I knew I would do anything to please her.
'Welcome my dear'.
Her voice was clear and precise and the accent was Home Counties. My mind
raced....for some reason I had assumed she was American. The idea of
revealing myself to someone who might only live a few miles away was even
more scary. For a moment I was hesitant, until I stammered.
'.......TTTttttthank you Miss. I'm sorry I kept you waiting'.
'No dear, you were actually a few seconds early. You're not in trouble.
Now tell me how your shopping trip went. You look delightful by the way,
very pretty'
I reddened as I heard myself described as pretty. Prompted by Miss Rachel
I launched into a detailed description of the clothes I had bought and how
long it had taken me to dress. She asked detailed questions and appeared
to be very interested in the more humiliating parts of my trip. I heard
her laugh when I told her how a grandmother had called me a pervert, she
quickly replied;
'Well that's what you are dear, isn't it? A little sissy pervert'.
Soon we moved on to how this was making me feel. I was totally honest and
I explained how I was torn between self disgust and a real feeling that
this was what I was born to. I had never worn stockings and heels before
but it already felt so natural, so right.
Suddenly she announced she wanted to see me walk.
'On your feet dear. Remember to swing your hips. Let's see plenty of ass,
men love a pretty girl's ass'.
Obediently I stood up and wobbled unsteadily on my heels. At Miss Rachel's
command I walked across the room and back again, as I was approaching the
computer again I heard the command 'CURTSY' barked out from the speakers.
I bobbed obediently before sitting back down again.
I felt ridiculous and humiliated, manipulated via a computer and telephone
line from many miles away. Then I looked at the screen. Miss Rachel was
smiling.
'Good Sophie, a very good start'.
It was like turning on a light bulb. Suddenly my self disgust was gone. I
had pleased Miss Rachel! Nothing else mattered as I basked in the warm
glow of her approval.
'Thank you Miss. I so much want to please you'.
She chuckled. 'Don't worry dear, you will. You have a lot of potential
and I intend to see that you fulfil it'.
After more chatting Miss Rachel ordered me to follow her to one of the chat
rooms that allowed the use of webcams. It was called 'Master and Servant'.
By now I had become used to the idea of Miss Rachel seeing me and talking
to me and relaxed slightly but I began to tense up again when I realised
everyone else in this room would be able to see me as well.
Actually, I loved it. Miss Rachel saw some friends were online and allowed
me to chat with the other subs. It was wonderful to meet so many people
just like me, and many who were dressed in even more bizarre costumes. I
saw one sissy dressed like a dancer in a tutu and another dressed in this
Alice In Wonderland little girl type pink party dress. There were a few
real females there (usually naked or topless) but most of my fellow subs
were sissies like me. We chatted about what everyone was wearing and the
punishment one of the girls had received from her Mistress for being caught
wearing trousers. They told me so many stories about their adventures that
my little willy was soon making a tent under my skirt. One girl told me
how she worked as a secretary in her Master's business and had been given
to a group of salesmen for the afternoon as a prize. The first she had
known about it was when she was ordered to strip down to her corset,
knickers, stockings and heels, locked into a set of irons and led into a
meeting room full of twenty something male salesmen. They were all very
interested in me and I told them as much as possible about Miss Rachel and
myself. They were keen to give me advice, when I confessed how scared I
was by the speed things were moving Jennifer told me;
'Don't worry babe. Just make sure you do everything your Mistress wants
and you'll be fine'.
Miss Rachel came and found me after about 2 hours. I was really relaxed by
then, I hadn't even looked at the clock. We chatted for a bit longer and
then she left. I was so excited, the last few hours had been like a dream
for me. It was wonderful to be able to express myself and know I had her
approval. It was a let down to have to take off those beautiful clothes
and remove my make up but I was buoyed by the knowledge that Miss Rachel
had already given me the time and date she wanted to see me again. I
couldn't wait.
That night I had the most intense dream ever. This time it was me kneeling
at the feet of Miss Rachel dressed in a PVC catsuit. I awoke drenched in
my own cum.
The next few weeks were blissful. I missed more and more college, spending
as much time as possible dressed and counting the hours until my next
meeting with Miss Rachel. She began to set me simple tasks, like putting
on a corset under my normal shirt, going into the local forest, removing
the shirt and taking a picture for her. She also made me go and buy a
large box of tampax so that I could have regular periods, just like proper
girls. I didn't mind the pain and humiliation, with each day that passed I
just wanted to spend more time pleasing Miss Rachel.
At the end of our third week Miss Rachel sprung her next surprise. We were
chatting about the latest task she had set me. She had written a short
classifieds ad which she ordered me to post on a Contact web site for subs
and doms. When I read it I was horrified, it was all about how I was a
submissive and kinky sissy desperate to meet a Master who would dress me as
his slut and use and humiliate me as his personal sex toy. It was bound to
appeal to all the dirty old men cruising the net. The worst part was that
it included my e-mail address. I was told that I had to reply to any
responses with my darkest, most disgusting fantasies. I then had to
forward those replies onto Miss Rachel. She would judge them and if she
felt I hadn't been kinky enough I would have to meet the man and carry out
the fantasy. If she liked my response I would be allowed to e-mail him
back and say that I had agreed to be collared by someone else.
As you can imagine I had taken a lot of care over my replies. I had
received three responses so far and Miss Rachel had been very pleased with
the three fantasies I had come up with. In fact I had amazed myself, some
of the stuff I had included was so filthy I would never have imagined
writing it down and sending it to a complete stranger a few weeks ago.
Miss Rachel was about to leave when she told me she had one new task for
me;
'I've decided you need a uniform Sophie. There's a shop I know in London,
which has just the thing. I've told them to expect you tomorrow at 7:00PM
to pick it up'.
She gave me an address in Soho and then continued.
'I want you in the right frame of mind so I've decided you can wear that
lovely red corset you bought last week with some panties and stockings
under your horrible rough boys clothes. Any questions dear? Good, I'll
expect to see you dressed in your new uniform on Thursday'.
She wanted me to meet other people. They would know I was a sissy. Her
sissy. This was a major step and she knew it. I looked up at the screen,
and saw she was staring at me. Like she was daring me to object.
'This will make me very happy Sophie'.
She always knew what to say. All the now familiar feelings came rushing to
the surface. Off course I would do it! It was what Miss Rachel wanted. I
nodded in submission.
'Of course Miss Rachel'.
The next day I caught the late afternoon train to London. It was the
middle of summer but I wore a coat zipped right up to the neck. It was the
thinnest coat I could find but I was still sweating. I was getting all
kinds of glances from the other passengers but I didn't care. There was no
way I was going to let anyone know what I was wearing under my jeans and
shirt.
When we got to Charring Cross station I started to walk down the Strand to
Trafalgar Square, past the National Gallery into Charring Cross Road, left
into Leicester Square and finally into the narrow streets of Soho. It was
raining very lightly and I hadn't brought an umbrella. For some reason
this struck me as funny, kind of appropriate given my present predicament.
As I got deeper and deeper into Soho the streets became narrower, the light
faded and the shops became more and more grubby. The shops were Thirties
style, to begin with I saw newsagents and convenience shops dotted between
the sex shops but as I got deeper and deeper into Soho everything else
disappeared and only the sex shops remained. The window displays left me
open mouthed in amazement, until a few weeks ago I'd had a sheltered
upbringing and never dreamed that shops like these existed. Some of the
windows were painted black with small signs by the door saying that the
council had banned their display.
Eventually I found the shop, it was a two story affair sandwiched between
two larger shops. There was a reed curtain covering the doorway and I
pulled it aside to walk in. The first thing I saw was a long thin room,
with piles and piles of cardboard boxes covering every open space. There
were three or four men browsing and one standing at the long thin wooden
counter, which took up the far left wall of the shop. The man was being
served by a middle aged woman with cropped black hair. She was very
overweight and wearing a dark stained kaftan.
As I walked over to the counter the man finished his purchase and turned to
leave the shop. The woman looked at me expectantly. Now the moment had
come to admit what I was to a complete stranger I was seized by a fresh
attack of nerves.
'I'm........ummm.......I'mm........Charlotte. Rachel sent me.'
The woman looked at me, blank faced.
'What?'
I tried again.
'Miss Rachel sent me. I have to collect a package'.
Recognition dawned.
'So you're Rachel's new sissy, eh?'
I cringed at the word 'sissy'.
'I KNOW she doesn't encourage such lack of respect. I will be sure to tell
her about that.'
Some customers raised their heads and started to look at us. They were
clearly amused. I blushed a livid red.
The woman continued.
'You will refer to me as Mistress Diane....MOLLY'.
There was an open doorway at the far end of the counter. After a delay of
a few seconds I saw a much younger much thinner woman come through the
doorway and walk towards us. She was dressed as a French Maid in a very
skimpy red satin uniform with white trim. The dress was low cut at the
front and I could see her breasts bouncing as she walked. The skirt was
tiny and puffed out with layers of lace underskirts and every time she took
a step I caught a glimpse of her stocking tops and panties. Her stockings
were very sheer and I could see a seem running dead straight up the back.
Although she was wearing 5" spike heels she was able to confidently pick
her way between the boxes and I didn't see her stumble once. She was very
tall and I couldn't help admiring her legs as she strolled towards us. She
came to a stop and caught her reflection in the mirror. Her hands
automatically flew up to straighten her cap and then brush her large white
apron straight. Now that she was standing next to us I could see her face
more clearly. Although she was wearing lots of make up I realised with a
shock this wasn't a woman at all. Molly was a guy! A sissy like me!
Mistress Diane turned to face her.
'Take Charlotte out the back and get her ready'.
I made a half hearted attempt to stop her.
'I'm wearing my underwear as ordered, look I'll show you'.
I undid two buttons on my shirt to reveal the basque. They showed
absolutely no interest. Molly pulled at my hand. She was surprisingly
strong.
'Come with me please'.
I had to lean closer to hear, her voice was so low it was almost as if she
was whispering. Her face was painfully thin and covered in white powder,
giving her a ghostly appearance. She pulled harder and I found myself
propelled through the door at the back of the shop to a kitchen area.
As with the rest of the shop there were piles of stock on every surface. I
caught a glimpse of an open box full of whips and another full of ball
gags. There was a cooking area and sink over by the window. The sink was
full of dirty plates and the whole area stank of fried food.
Molly reached up and started to undo the rest of my shirt buttons.
'I'm only supposed to show you I'm wearing the underwear. She didn't say
anything about undressing...'
Quick as a flash she leaned in until her face was almost touching mine.
'Shhhhhhhhhhhhh................................'
She raised one finger to her heavily painted lips. I looked into her eyes
and saw real fear.
'She'll hear you. Just keep quiet. It's for the best'.
She continued to undress me. I was too shocked to resist. Molly was
terrified, absolutely terrified of what Miss Diane might do to her. This
wasn't my fantasy, where sissies lived to serve their Superiors who treated
them with love and respect. This was some cruel warped world I was being
drawn into.
In no time at all I was naked except for my feminine lingerie. Molly
circled round inspecting me from several angles before releasing the
strings on my corset and pulling them in as tight as they would go. She
leaned against my back to gain leverage, I was too busy trying to breathe
to waste time complaining. When she stepped back I found the corset had
forced what little fat I had up so it looked like I had two little girlish
breasts.
Next Molly crossed to one of the boxes and pulled out a French Maid's dress
exactly like the one she was wearing. She unzipped it and signalled for me
to step in. Taking tiny breaths I crossed the room and put on the dress.
Even with my reduced waist it was a tight fit and Molly had to pull hard to
zip me up. As she finished I noticed she picked up a small shiny object
from the table. It was just out of my field of vision so it was only when
I heard the padlock snap shut that I realised I had been locked into the
dress.
Next Molly sat me down in front of the mirror and found a long blonde wig
to fit me. Then she found some make up and started work on my face. After
a few minutes she had slapped so much on that I looked like a tart. My own
mother wouldn't have recognised me.
To finish off Molly disappeared into one of the cupboards, burrowing down
into the pile of boxes so that only her panty covered ass and gloriously
long legs were visible. She reappeared with a pair of 5" spike heels with
locking ankle straps, a mop cap and starched white apron and red elbow
length gloves.
After a few more minutes Molly pronounced herself happy with my appearance
and pulled me to my feet to take me back through to meet Miss Diane. The
moment I caught my reflection in the mirror was heart stopping. I had come
in here a gawky young man and Molly had turned me into this sexy goddess
dressed to kill.
Miss Diane's verdict was less charitable. She looked me up and down.
'Hmmm.......not bad for a beginner. A wanabee slut'.
I watched as she opened a draw and pulled out a thin leather collar. It
looked like a dog's collar and had a thick metal ring set into each side.
She reached up and pulled my hair back so she could fit the collar around
my neck. I heard a loud click as she snapped the lock shut.
'I have some wonderful news for you Charlotte'.
Even in my heels Mistress Diane was a full three inches taller than me.
She beamed down.
'I talked to your Mistress this afternoon. She's agreed that you can help
us out for a few hours in return for your lovely new uniform. So you can
get behind the counter with Molly! Isn't that lovely? I want to see hard
work mind. I don't want you two girls gossiping all night and ignoring the
customers. We close at 9:00 tonight - lots of work to do'.
She must have seen the expression on my face.
'Of course you don't have to stay. You're free to go if you want. No-one
around here will take any notice if you walk down the street in that
outfit. You might have some trouble getting on the train in the rush hour
though. All those crowds. Bound to crease your dress. If you're lucky
some nice strong young man will look after you...'
There was the sound of cackling laughter from the shoppers. What could I
do? Head down I walked over to the counter to join Molly.
In the end it wasn't nearly as bad as I feared. The customers were mostly
respectful and I quickly learnt to deal with the few that did try and feel
me up. There were plenty of mirrors in the shop and each time I saw this
sexy young girl strolling round in her skimpy outfit my confidence grew. I
also realised very quickly that most of the customers were afraid of me. I
knew I was convincing, and they seemed to see me as a totally feminine
image of all their fantasies. Most of them couldn't help thinking about
what they'd like to do to me. As a result they were blushing and hesitant
and usually talking straight to my chest. I exploited this balance of
power without mercy by flirting with every customer that looked halfway
presentable. I can't describe the feeling that came over me when some
blushing young teenager came over and asked for something. It sent a
thrill down my spine. Of course, not all customers were easy to deal with.
One in particular spent at least 30 minutes bullying Molly when she didn't
curtsey quick enough. He was fat and middle aged with a cruel face and I
remember being glad I didn't have to deal with him.
Soon it was 9:00 and Mistress Diane let out the last customers and bolted
the doors. I was so glad to see that door shut, Molly had been sent off to
do something for Mistress Diane about 30 minutes ago and I had been rushed
off my feet trying to cope with all the customers. I turned expectantly.
'May I go and get changed now please?'
Mistress Diane glowered at me. Several times during the evening she had
told me off for flirting with customers.
'Come with me first slut. I have a job for you'.
By Charlotte
This story contains scenes of an erotic nature and is not intended for
minors. Further, if such material is considered illegal in your area, you
should by bypass this story. This story remains the property of the
author. Permission is granted to download, photocopy, copy and re-post as
long as any such action contains these disclaimers, and no attempt is made
to profit from this story.
Today is my wedding day. The ceremony doesn't start for ninety minutes but
I am already wearing my dress. It is ivory silk with a full-length skirt,
tight bodice and puff sleeves. When I saw it in the shop I knew I had to
have it. It's just gorgeous and makes me feel like a princess. I'm also
wearing a very tight cream corset, matching french cut panties and
stockings. My shoes are so delicate and feminine, 3" heels with just two
thin straps securing them to my ankle. I often wear much higher heels but
I will be on my feet all day and I don't want to get tired. I sink back
into the chair behind me and finger the tiny scar on my neck where I had
the operation. In order to get at the scar I have to push up the thin
metal collar I wear all the time now. Miss Rachel was kind enough to make
the collar loose fitting so it is easy to move. I run my long red nails up
and down my body, hardly daring to believe today has come. My artificial
breasts strain against their layers of silken constraints as I think back
over the events of the last 2 years and my little sissy clitty starts to
stir in its metal prison.
Miss Rachel has promised that if I am good today she may even remove my
chastity belt tonight. I am resolved to be as well behaved as I can and
really make her proud of me. I hated that thing when she first put it on
me but I now understand the reasons she had to do it. It is frustrating
and sometimes painful not to have control of my own pee-pee but I have
accepted that it belongs to her now. Also, wearing the chastity belt has
made me so much more compliant and feminine. When she first told me we
were to be married I was apprehensive. When she explained that I would be
the one wearing the dress and I would have to promise to obey her I was
downright scared. The fact that she put me on a crash diet so I could fit
into the costume she wants me to wear for the entertainment at the
Reception didn't help. Gradually I've come round to the idea. It's a
shame my parents have refused to attend but I know if they did come they'd
only create a scene. No, today must be perfect. It's my chance to
demonstrate to the whole world the commitment I've made to Miss Rachel. I
lean back in my chair, close my eyes and think back to how it all started.
It all started two years ago because it was Friday night and I was bored
and there was nothing on television. I was an 18-year-old kid who had just
started university. My parents were rich and when they first suggested
buying me a flat I thought it was a great idea. Unfortunately I was
finding out that living on your own made it a lot harder to make friends.
For the last few years my parents had paid to send me to private school.
On the surface I was a normal schoolboy, missing classes and drinking at
the weekends whenever I got the chance. However there was one big secret
nobody knew about. For years and years I had fantasised about dressing in
girls clothes. Of course I never did anything about it, I was much too
much of a wimp and my parents would have died of shame if they found out.
I just fantasised endlessly about dressing like my sisters and doing all
the things I saw them doing.
Today was different though. Earlier this afternoon I had bought a computer
and I just installed the ISP software. I was hooked up and ready to
connect to the internet for the first time in my life.
I had read about chat rooms in the newspaper and wanted to see what they
were like. The first thing I did was head for Yahoo because that was the
only one I had heard of. It took me a moment to download their software
and work out what was happening and then I was away. I choose the first
name that came into my head, 'sissy'. I didn't bother to fill in the
profile; I just wanted to get on line as soon as possible. After I found
the adult rooms I surfed around a bit, generally being ignored. On one
level it was very strange, these people were thousands of miles apart
pretending they were in the same room. On another level it was strangely
erotic, I found myself watching Hercules dominating his sub pretty_flower
by forcing her to pretend to give him a blowjob in the middle of the chat
room.
Suddenly a message box popped up in the middle of my screen,
'Busy slut?'
I looked at the top of the box, it was sent by 'Cruel_Master_James'.
A few seconds later another line appeared below the first one.
'I asked you a questions slut'.
I panicked. I moved my mouse instinctively and killed the connection.
Instantly I regretted it. What was I doing? I couldn't wimp out again.
For years I had fantasised about discussing my yearnings with like minded
people and at the first chance I had I wimped out.
Eventually I reconnected and found the chat site again. This time I
decided to go for a more descriptive name and set up a profile as
'male_sissy_maid'. I typed some rubbish into the description about how I
liked to dress from time to time and go to clubs. I also found a S&M site
and borrowed a picture of a very thin man dressed as a secretary in a
blouse and tight pencil skirt, wearing a dog collar and chains and kissing
the thigh boots of a blonde sex goddess dressed in an all in one PVC
catsuit.
I soon found a room called 'Slut TV's in a dark alley' and decided to take
a look. It was full of people but it was clear most of them were engaged
in private conversations and I couldn't find anyone to talk to. The few
that did want to talk were only interested in my telephone number. After
about fifteen minutes I was about to leave when a private message popped up
on my screen.
'Interesting photo. Is it you?'
I looked at the name - 'Hercules'. Hmmm.....he was clearly going to be
disappointed by the truth so I decided to lie.
'Yes Sir'.
'You're very pretty slut. Tell me about yourself'.
That was all the excuse I needed. For the next 30 minutes I chatted with
Hercules. It was only later I realised I had told him all sorts of things
about me but had learned absolutely nothing about him. It didn't seem to
matter; I was overcome with relief at being able to talk to someone about
my inner desires with no fear of ever meeting them. The little white lies
I told along the way didn't seem to matter; when Hercules asked me what I
was wearing I told him a tight black leather mini, blouse, stockings and
spike heels. He encouraged me along the way, asking what turned me on, how
I saw myself.....it was kind of like talking to a kinky psychiatrist.
Eventually he asked if I wanted to be placed under his guidance. I nearly
came when I heard that. He wanted to help me fulfil my innermost dreams
and desires. I had only been online for an hour or so and here was someone
offering to do exactly what I wanted.
Immediately I said yes a change seemed to come over Hercules. He insisted
I sent a message in the open room begging to be allowed to serve him. He
pretended not to be interested and replied telling me to crawl towards him
on my hands and knees. Then he asked me to tell everyone how I was
dressed. My cheeks were red and my little sissy cock was straining as I
read the comments from some of the other people in the room. It looked
like they were used to this sort of thing!
With feigned reluctance Hercules eventually said yes. He asked me what I
was wearing again and when I gave the same answer he told me to go and get
a length of rope. As fast as I could I ran into the hall of my flat and,
kicking off my clothes, came and sat down again in front of the computer.
I was now stark naked. I typed out a message;
'I have done as you ordered Sir'.
'Good slut. First remove your skirt and panties. Then take one end of the
rope and tie it around the base of your cock and balls. Pull it to make
sure it's tight. Then thread the rope between your legs, loop around your
waist and tie it off. I want your TINY little cock hidden between your
legs. Then put your knickers and skirt back on.'
I looked at the screen. Hell! That was going to hurt. Strangely, I never
thought of disobeying. Hercules was probably thousands of miles away but I
felt like he was in the room with me ordering me to do this with the crowd
egging him on. There was no way I could do anything other than he ordered.
Submission came naturally to me.
Very gingerly I looped the rope around my ball sac and pulled tight. I was
right, it did hurt!
I typed out a message telling him I had obeyed. Suddenly I heard a single
voice coming out of my speaker. Dimly I wondered why I hadn't noticed this
room had voice chat as well.
'Let's see if the sissy is any good at sucking cock Hercules'.
There was a gaggle of laughter. The message from Hercules was clear
enough.
'On your knees slut'.
Without thinking about it I slipped off my chair and fell to my knees.
This man was thousands of miles away from me but the instinct to obey was
so strong that I never considered doing anything else. I found my eyes
were half closed and my lips pursed almost as though I was ready to receive
his penis in real life. Without thinking about it I started to type. To
this day I can't remember much but I could almost taste a strong musky
smell in my throat. On one level it was absurd, I was pretending to have
oral sex with this man who wasn't even in the same country to me. To me it
seemed perfectly natural however, I was so ready to give myself to anyone
who noticed me.
I had had a few girlfriends and one in particular who enjoyed the taste of
my cum. I thought back to what she had done and what I had enjoyed.
Gradually I relaxed, words like 'moist lips' featured a lot. The rest of
the room obviously enjoyed the entertainment; there was a constant stream
of comments from my loud speakers. Eventually Hercules came, turning his
microphone up loud so the whole room could hear. That wasn't the end of my
performance however; I spent the next 2 hours sucking off every other male
in the room under his direction. Time seemed to pass quickly, I was
totally immersed in trying to please Hercules. Finally I saw him type out
a message.
'I am going now. I hope you all enjoyed today's entertainment'.
Quickly I typed out a reply.
'When will I see you again Master?'
For the first time I heard Hercules's voice, a low chilling laugh in my
speakers.
'See me again? You really believed I am interested in owning you? This
was strictly a one night stand sissy. Crawl back under your rock, there
are thousands like you begging to serve me everytime I log on'.
I was numb. I heard the rest of the room laughing at the way I had been
used. Used and thrown away like the pathetic sissy I was. How could I
complain? Wasn't this exactly the treatment I had begged for? My little
sissy clitty was straining. Remembering my manners I was polite to the
last.
'I hope my service was satisfactory Sir'.
I logged off with renewed laughter ringing in my ears.
I slept late the next day. When I got up I didn't even look at the
computer, after a late lunch I went out to do some food shopping. It was
late in the afternoon before I had put everything away and I decided to
have a quick look on the internet to see if I could find out what was on TV
that night. Almost as soon as I logged on I saw a little envelope icon at
the bottom right of the screen. When I clicked on it an e-mail inbox
appeared. This was strange, I hadn't signed up for an e-mail account yet.
Then I saw the name at the top of the screen, 'sissy_male_maid'. I
realised the account must have been automatically created last night when I
used the chat room. I had been so upset I hadn't logged out so the
computer had retrieved the messages for me when I logged on again.
There were two unread e-mails; the first was the traditional 'Welcome'
message. The second was more interesting. It was from someone calling
herself 'Mistress Rachel' and was headed 'You'. I double clicked to open
it.
'Sissy
I was in the chat room yesterday and saw your display for Hercules.
Although it was clear you have little experience I was impressed by your
obedience and natural subservience. To the end you treated your Superiors
with the respect that is their due. I am not going to try and defend the
way Hercules used you, however you clearly understood that it is not for
sissies to question their Superiors and continued to display the
appropriate dignity and deference.
I would welcome the chance to talk with you further, although I appreciate
that after your experience yesterday you may have reservations. If you are
available I will be on line tonight at 17:30 UK time. It would please me
if you were there.
Regards
Mistress Rachel'
I felt light headed...this was a real Mistress. She wanted to talk to me!
Suddenly I glanced at my watch. Hell! It was 5:23 already. I had 7
minutes.
Frantic now I jumped up from my seat and pulled the curtains shut. I fixed
myself some sandwiches and a drink, took them out to the computer and then
checked all the doors and windows were shut. Before logging on again I
stripped off my clothes. Looking at the clock on the computer I saw I had
less than sixty seconds left.
She was waiting for me. As soon as I entered the chat room a message box
popped up;
'Welcome sissy. I'm glad you could make it'.
Suddenly I was incredibly nervous. What was I doing?
'Thank you Mistress. Ummm........thank you for your e-mail'.
'Welcome dear, but please call me Miss Rachel. Your performance last night
fascinated me. You showed a lot of potential. I wanted a chance to chat
with you'.
For the next three hours we talked. Just talked. Miss Rachel asked me
about my background; my fears and desires, hopes and dreams. I was as
honest as I could be but still maintained the rubbish I had typed into my
chat profile yesterday was true. I didn't feel able to tell her I had
misled her so early on. All the time she quietly encouraged me to open up
until I heard myself telling Miss Rachel things I hadn't realised myself.
I explained my constant dreams and fantasies where I always played the role
of the submissive sissy and the effect this had on me. When I told Miss
Rachel that my name in these fantasies was always Sophie she graciously
agreed that I could keep that name. She began to tell me a few things
about herself, I learnt she had trained a number of real life sissy maids
in the past but currently did not own any.
She told me a number of stories about how she had humiliated her girls.
Each story turned me on more than the last and I knew beyond doubt that
this was the life for me. When I heard her final story about how she had
punished a slave who had been masturbating without permission by dressing
her like a slut in a tiny red miniskirt and red PVC thigh length high
heeled boots and dropping her in a town 80 miles away in the middle of the
night my little sissy clitty felt like it was about to explode. The girl
only got home by hitching a ride with a trucker. She spent the entire ride
kneeling in front of the driver with his penis in her mouth. This was a
whole new world to me and I knew then that I wanted it more than I had ever
wanted anything.
Eventually Miss Rachel told me she had to go. I asked her when we would
chat again. Her answer shocked me;
'Never, unless you learn to be honest with me.'
'I don't understand. What do you mean?'
'Well - for a start that picture on your profile isn't you, is it?'
Even though she was many miles away I turned beet red.
'Ummmm.....no. I am so sorry Miss'.
'You will be. Understand this, I will not tolerate any form of
disobedience or lying. Being a good sissy takes dedication and self
sacrifice. It will take over your life, it is not just something to play
at on the weekend. I will be here at the same time in 2 days. Think
carefully. If you want to see me again I have some tasks for you to
complete in the next 48 hours.'
'Anything Miss. I am just so sorry to have disappointed you'.
'Hmmm....well. You have 48 hours to prove that. You've already told me
you have plenty of money, now you will spend some. I want your profile
updated with TRUE information and a real picture of you. Buy a digital
camera and scanner if you have to. From now on I want you properly dressed
every time we meet. Go out and buy yourself a wardrobe; skirts, dresses,
lingerie, shoes but NO pants. No flat shoes either. Don't forget the make
up, it's so important for sissies to be well turned out.
Finally - and this is most important - you are to get yourself a webcam and
microphone. I want to be able to see you and hear you. I'm not wasting my
time typing out messages, if you have any doubts you should tell me now.
That's a lot to remember for an airhead like you. Do you have it all
dear?'
I could only stare at the screen. When I started down this path I had no
idea how far I would go but in my wildest dreams I never imagined this. The
idea of finally having my own wardrobe thrilled me and yet terrified me at
the same time. The idea of someone else seeing me dressed really terrified
me! Yet, I could stop this at any time. She hadn't asked for my real name
or address. I could experiment by obeying her and then just delete my
profile later and stop logging on if I needed to. I wanted to obey Miss
Rachel so much. I had spent most of my life wimping out, there was no way
I was avoiding my fantasies again. I gave the only answer I could.
'I understand perfectly Ma'am. I will be here in 2 days'.
Looking back I wonder why I never thought of arguing with her, asking for
more time before taking such a big step. I think it was because I could
not disappoint Miss Rachel again; I had to prove myself worthy of her
attention. In the short time I had been with her I had subconsciously
accepted her as my Superior and her approval was increasingly important to
me. In fact, her approval was becoming the only issue of importance in my
life.
The following morning I skipped college and drove to a large town about 80
miles away. The computer equipment was easy, I just went straight to the
local branch of Dixons. The clothes were more difficult, it was
horrendously embarrassing just to walk into Dorothy Perkins. The first two
times I tried I turned such a vivid shade of red I left before a sales
assistant threw me out. After an hour I nearly had a crying fit when a
grandmother out shopping with her granddaughter pointed at me and said
'That's a pervert dear'.
I managed to buy a few things and eventually decided to go back to my car
and drive into London. It seemed to make things easier, there were more
people in the shops and even some men shopping for wives and girlfriends.
It was still embarrassing, one shop assistant insisted on holding up a
short black velvet dress to see if it would fit when I tried to buy it.
Eventually I had enough clothes to please Miss Rachel when I chatted with
her again, I resolved to buy the rest from mail order!
The only thing I hadn't managed was shoes, clearly no shop assistant was
going to allow me to try on high heels and from what I saw of the sizes
they all looked a bit small for me anyway. Eventually I had a stroke of
genius, I took the Tube over to Kings Cross and went to a transvestite shop
I had seen before in the run down area behind the station. Once I got over
the initial shock of seeing so many other guys like me shopping for girl's
clothes it was quite easy. I ended up buying one pair with a four inch
pencil heel and wrap around strap and one pair of ankle boots with a wider
five inch heel.
It was nearly midnight when I got home and I was exhausted. I really,
really wanted to try something on but I just lay down on my bed first for a
quick rest. I closed my eyes just for a second, the next thing I knew I
was awakened by the sound of cars in the road outside. I looked at my
watch, it was 10:00AM. I had slept right through past the alarm!
Resolving to make the best of things I decided to spend the day pampering
myself.
After calling into college to take another day off I ran a lovely hot bath,
using some scented oils. While in there I shaved every inch of my body
below my neck. After climbing out of the bath I dried my hair into what I
hoped was a feminine style and sat down in front of the mirror to do my
makeup. I had no experience of using makeup before so my first few
attempts were a bit of a disaster. Far too much rouge, blusher and
mascara. After about half an hour I learnt to go easy on the blusher and
mascara and managed a half way respectable look. It was still a bit tarty
but at least I didn't look like Barbara Cartland.
It was a real shock to look in the mirror and see this feminine face
attached to my body. I ran my hands up and down my smooth body, revelling
in the submissive and feminine feelings that overtook me.
After a few seconds I picked up the bag from Knickerbox and dropped my new
lingerie collection onto the bed. When I was in their shop yesterday I
pretended to be shopping for my girlfriend, everything I bought was silk or
lace and very, very delicate. I picked out a matching bra, high cut
panties and suspender belt in cream silk, my poor little penis was rock
hard as I slid the panties up my legs. It took me a few minutes to get the
stockings on properly, I loved the sensation as they pulled against my
suspender belt when I snapped them in position.
I routed around the pile of clothes on my bed and decided to wear the black
velvet dress. The skirt was tighter than I thought and my painfully stiff
errection was forcing it out into a tent. Eventually I managed to reach
round and pull the zip up, I couldn't help but run my hands up and down my
new body. After putting on my new 4" heels I practised walking across the
room a few times to get used to them. It was the first time I had ever
worn heels and I nearly broke my ankle a couple of times. Soon I was
swinging my ass as I'd seen the girls do down the pub on a Friday night and
it all became much easier. After about 10 minutes I had forgotten I was
wearing them. I caught sight of myself in the mirror and had to stop for a
double take. I was gorgeous! I'd never really had much luck with the
girls, my body wasn't really up to much. I'd been transformed into a sexy,
sassy young woman of the sort I lusted after on the infrequent occasions I
went to nightclubs. I'd never felt like this before, so vulnerable and
feminine. All my doubts had gone, I knew I could pass as a girl and I
loved the way it made me feel.
I had about 2 hours until my appointment with Miss Rachel. I didn't have
the courage to go anywhere so I sat down to watch some television. I had
bought some long red false nails yesterday so I busied myself attaching
them to my fingers. It was so strange to be sitting there watching 'This
Morning' and playing with my vampish red nails. I even found myself paying
special attention to the beauty items, wondering how the makeover was going
to turn out and what I would look like in the ridiculously short skirt they
had put their middle aged victim into. As my appointment with Miss Rachel
drew nearer I became more and more nervous, getting up to pace the
apartment and reassuring myself by checking my appearance in the mirror.
About forty minutes before my appointment I suddenly realised I needed a
feminine voice. There was no way I could use my normal voice, dressed as I
was! The whole experience was already going to be extremely humiliating.
Luckily my voice was quite high, I started with this high pitched squeak
rather like Minnie Mouse but soon graduated to a lower Bette Davies tone I
felt I could maintain reasonably consistently. It was weird hearing this
odd voice coming out of my mouth, I practised by reading items out of a
magazine until I could manage two minutes without changing my pitch.
Eventually it was time and I logged on. I saw the icon indicating Miss
Rachel was already there so I raised my trembling hand to turn the webcam
on.
The screen flickered for a few seconds and then the colours began to form
to reveal this gorgeous woman. It sounds like a clich' but the first
thought to register in my mind was that Miss Rachel was stunningly
beautiful. She was in her late twenties, slim with shoulder length blonde
hair and largish breasts. She was sitting down wearing this very tight red
wrap around dress. Her eyes were green and the most piercing I had ever
seen. They appeared to be staring right at me. Behind her I could see
some French Windows and a neatly kept garden. Then I saw her face light up
as she began to smile. I realised she could now see me as well. At that
moment I knew I would do anything to please her.
'Welcome my dear'.
Her voice was clear and precise and the accent was Home Counties. My mind
raced....for some reason I had assumed she was American. The idea of
revealing myself to someone who might only live a few miles away was even
more scary. For a moment I was hesitant, until I stammered.
'.......TTTttttthank you Miss. I'm sorry I kept you waiting'.
'No dear, you were actually a few seconds early. You're not in trouble.
Now tell me how your shopping trip went. You look delightful by the way,
very pretty'
I reddened as I heard myself described as pretty. Prompted by Miss Rachel
I launched into a detailed description of the clothes I had bought and how
long it had taken me to dress. She asked detailed questions and appeared
to be very interested in the more humiliating parts of my trip. I heard
her laugh when I told her how a grandmother had called me a pervert, she
quickly replied;
'Well that's what you are dear, isn't it? A little sissy pervert'.
Soon we moved on to how this was making me feel. I was totally honest and
I explained how I was torn between self disgust and a real feeling that
this was what I was born to. I had never worn stockings and heels before
but it already felt so natural, so right.
Suddenly she announced she wanted to see me walk.
'On your feet dear. Remember to swing your hips. Let's see plenty of ass,
men love a pretty girl's ass'.
Obediently I stood up and wobbled unsteadily on my heels. At Miss Rachel's
command I walked across the room and back again, as I was approaching the
computer again I heard the command 'CURTSY' barked out from the speakers.
I bobbed obediently before sitting back down again.
I felt ridiculous and humiliated, manipulated via a computer and telephone
line from many miles away. Then I looked at the screen. Miss Rachel was
smiling.
'Good Sophie, a very good start'.
It was like turning on a light bulb. Suddenly my self disgust was gone. I
had pleased Miss Rachel! Nothing else mattered as I basked in the warm
glow of her approval.
'Thank you Miss. I so much want to please you'.
She chuckled. 'Don't worry dear, you will. You have a lot of potential
and I intend to see that you fulfil it'.
After more chatting Miss Rachel ordered me to follow her to one of the chat
rooms that allowed the use of webcams. It was called 'Master and Servant'.
By now I had become used to the idea of Miss Rachel seeing me and talking
to me and relaxed slightly but I began to tense up again when I realised
everyone else in this room would be able to see me as well.
Actually, I loved it. Miss Rachel saw some friends were online and allowed
me to chat with the other subs. It was wonderful to meet so many people
just like me, and many who were dressed in even more bizarre costumes. I
saw one sissy dressed like a dancer in a tutu and another dressed in this
Alice In Wonderland little girl type pink party dress. There were a few
real females there (usually naked or topless) but most of my fellow subs
were sissies like me. We chatted about what everyone was wearing and the
punishment one of the girls had received from her Mistress for being caught
wearing trousers. They told me so many stories about their adventures that
my little willy was soon making a tent under my skirt. One girl told me
how she worked as a secretary in her Master's business and had been given
to a group of salesmen for the afternoon as a prize. The first she had
known about it was when she was ordered to strip down to her corset,
knickers, stockings and heels, locked into a set of irons and led into a
meeting room full of twenty something male salesmen. They were all very
interested in me and I told them as much as possible about Miss Rachel and
myself. They were keen to give me advice, when I confessed how scared I
was by the speed things were moving Jennifer told me;
'Don't worry babe. Just make sure you do everything your Mistress wants
and you'll be fine'.
Miss Rachel came and found me after about 2 hours. I was really relaxed by
then, I hadn't even looked at the clock. We chatted for a bit longer and
then she left. I was so excited, the last few hours had been like a dream
for me. It was wonderful to be able to express myself and know I had her
approval. It was a let down to have to take off those beautiful clothes
and remove my make up but I was buoyed by the knowledge that Miss Rachel
had already given me the time and date she wanted to see me again. I
couldn't wait.
That night I had the most intense dream ever. This time it was me kneeling
at the feet of Miss Rachel dressed in a PVC catsuit. I awoke drenched in
my own cum.
The next few weeks were blissful. I missed more and more college, spending
as much time as possible dressed and counting the hours until my next
meeting with Miss Rachel. She began to set me simple tasks, like putting
on a corset under my normal shirt, going into the local forest, removing
the shirt and taking a picture for her. She also made me go and buy a
large box of tampax so that I could have regular periods, just like proper
girls. I didn't mind the pain and humiliation, with each day that passed I
just wanted to spend more time pleasing Miss Rachel.
At the end of our third week Miss Rachel sprung her next surprise. We were
chatting about the latest task she had set me. She had written a short
classifieds ad which she ordered me to post on a Contact web site for subs
and doms. When I read it I was horrified, it was all about how I was a
submissive and kinky sissy desperate to meet a Master who would dress me as
his slut and use and humiliate me as his personal sex toy. It was bound to
appeal to all the dirty old men cruising the net. The worst part was that
it included my e-mail address. I was told that I had to reply to any
responses with my darkest, most disgusting fantasies. I then had to
forward those replies onto Miss Rachel. She would judge them and if she
felt I hadn't been kinky enough I would have to meet the man and carry out
the fantasy. If she liked my response I would be allowed to e-mail him
back and say that I had agreed to be collared by someone else.
As you can imagine I had taken a lot of care over my replies. I had
received three responses so far and Miss Rachel had been very pleased with
the three fantasies I had come up with. In fact I had amazed myself, some
of the stuff I had included was so filthy I would never have imagined
writing it down and sending it to a complete stranger a few weeks ago.
Miss Rachel was about to leave when she told me she had one new task for
me;
'I've decided you need a uniform Sophie. There's a shop I know in London,
which has just the thing. I've told them to expect you tomorrow at 7:00PM
to pick it up'.
She gave me an address in Soho and then continued.
'I want you in the right frame of mind so I've decided you can wear that
lovely red corset you bought last week with some panties and stockings
under your horrible rough boys clothes. Any questions dear? Good, I'll
expect to see you dressed in your new uniform on Thursday'.
She wanted me to meet other people. They would know I was a sissy. Her
sissy. This was a major step and she knew it. I looked up at the screen,
and saw she was staring at me. Like she was daring me to object.
'This will make me very happy Sophie'.
She always knew what to say. All the now familiar feelings came rushing to
the surface. Off course I would do it! It was what Miss Rachel wanted. I
nodded in submission.
'Of course Miss Rachel'.
The next day I caught the late afternoon train to London. It was the
middle of summer but I wore a coat zipped right up to the neck. It was the
thinnest coat I could find but I was still sweating. I was getting all
kinds of glances from the other passengers but I didn't care. There was no
way I was going to let anyone know what I was wearing under my jeans and
shirt.
When we got to Charring Cross station I started to walk down the Strand to
Trafalgar Square, past the National Gallery into Charring Cross Road, left
into Leicester Square and finally into the narrow streets of Soho. It was
raining very lightly and I hadn't brought an umbrella. For some reason
this struck me as funny, kind of appropriate given my present predicament.
As I got deeper and deeper into Soho the streets became narrower, the light
faded and the shops became more and more grubby. The shops were Thirties
style, to begin with I saw newsagents and convenience shops dotted between
the sex shops but as I got deeper and deeper into Soho everything else
disappeared and only the sex shops remained. The window displays left me
open mouthed in amazement, until a few weeks ago I'd had a sheltered
upbringing and never dreamed that shops like these existed. Some of the
windows were painted black with small signs by the door saying that the
council had banned their display.
Eventually I found the shop, it was a two story affair sandwiched between
two larger shops. There was a reed curtain covering the doorway and I
pulled it aside to walk in. The first thing I saw was a long thin room,
with piles and piles of cardboard boxes covering every open space. There
were three or four men browsing and one standing at the long thin wooden
counter, which took up the far left wall of the shop. The man was being
served by a middle aged woman with cropped black hair. She was very
overweight and wearing a dark stained kaftan.
As I walked over to the counter the man finished his purchase and turned to
leave the shop. The woman looked at me expectantly. Now the moment had
come to admit what I was to a complete stranger I was seized by a fresh
attack of nerves.
'I'm........ummm.......I'mm........Charlotte. Rachel sent me.'
The woman looked at me, blank faced.
'What?'
I tried again.
'Miss Rachel sent me. I have to collect a package'.
Recognition dawned.
'So you're Rachel's new sissy, eh?'
I cringed at the word 'sissy'.
'I KNOW she doesn't encourage such lack of respect. I will be sure to tell
her about that.'
Some customers raised their heads and started to look at us. They were
clearly amused. I blushed a livid red.
The woman continued.
'You will refer to me as Mistress Diane....MOLLY'.
There was an open doorway at the far end of the counter. After a delay of
a few seconds I saw a much younger much thinner woman come through the
doorway and walk towards us. She was dressed as a French Maid in a very
skimpy red satin uniform with white trim. The dress was low cut at the
front and I could see her breasts bouncing as she walked. The skirt was
tiny and puffed out with layers of lace underskirts and every time she took
a step I caught a glimpse of her stocking tops and panties. Her stockings
were very sheer and I could see a seem running dead straight up the back.
Although she was wearing 5" spike heels she was able to confidently pick
her way between the boxes and I didn't see her stumble once. She was very
tall and I couldn't help admiring her legs as she strolled towards us. She
came to a stop and caught her reflection in the mirror. Her hands
automatically flew up to straighten her cap and then brush her large white
apron straight. Now that she was standing next to us I could see her face
more clearly. Although she was wearing lots of make up I realised with a
shock this wasn't a woman at all. Molly was a guy! A sissy like me!
Mistress Diane turned to face her.
'Take Charlotte out the back and get her ready'.
I made a half hearted attempt to stop her.
'I'm wearing my underwear as ordered, look I'll show you'.
I undid two buttons on my shirt to reveal the basque. They showed
absolutely no interest. Molly pulled at my hand. She was surprisingly
strong.
'Come with me please'.
I had to lean closer to hear, her voice was so low it was almost as if she
was whispering. Her face was painfully thin and covered in white powder,
giving her a ghostly appearance. She pulled harder and I found myself
propelled through the door at the back of the shop to a kitchen area.
As with the rest of the shop there were piles of stock on every surface. I
caught a glimpse of an open box full of whips and another full of ball
gags. There was a cooking area and sink over by the window. The sink was
full of dirty plates and the whole area stank of fried food.
Molly reached up and started to undo the rest of my shirt buttons.
'I'm only supposed to show you I'm wearing the underwear. She didn't say
anything about undressing...'
Quick as a flash she leaned in until her face was almost touching mine.
'Shhhhhhhhhhhhh................................'
She raised one finger to her heavily painted lips. I looked into her eyes
and saw real fear.
'She'll hear you. Just keep quiet. It's for the best'.
She continued to undress me. I was too shocked to resist. Molly was
terrified, absolutely terrified of what Miss Diane might do to her. This
wasn't my fantasy, where sissies lived to serve their Superiors who treated
them with love and respect. This was some cruel warped world I was being
drawn into.
In no time at all I was naked except for my feminine lingerie. Molly
circled round inspecting me from several angles before releasing the
strings on my corset and pulling them in as tight as they would go. She
leaned against my back to gain leverage, I was too busy trying to breathe
to waste time complaining. When she stepped back I found the corset had
forced what little fat I had up so it looked like I had two little girlish
breasts.
Next Molly crossed to one of the boxes and pulled out a French Maid's dress
exactly like the one she was wearing. She unzipped it and signalled for me
to step in. Taking tiny breaths I crossed the room and put on the dress.
Even with my reduced waist it was a tight fit and Molly had to pull hard to
zip me up. As she finished I noticed she picked up a small shiny object
from the table. It was just out of my field of vision so it was only when
I heard the padlock snap shut that I realised I had been locked into the
dress.
Next Molly sat me down in front of the mirror and found a long blonde wig
to fit me. Then she found some make up and started work on my face. After
a few minutes she had slapped so much on that I looked like a tart. My own
mother wouldn't have recognised me.
To finish off Molly disappeared into one of the cupboards, burrowing down
into the pile of boxes so that only her panty covered ass and gloriously
long legs were visible. She reappeared with a pair of 5" spike heels with
locking ankle straps, a mop cap and starched white apron and red elbow
length gloves.
After a few more minutes Molly pronounced herself happy with my appearance
and pulled me to my feet to take me back through to meet Miss Diane. The
moment I caught my reflection in the mirror was heart stopping. I had come
in here a gawky young man and Molly had turned me into this sexy goddess
dressed to kill.
Miss Diane's verdict was less charitable. She looked me up and down.
'Hmmm.......not bad for a beginner. A wanabee slut'.
I watched as she opened a draw and pulled out a thin leather collar. It
looked like a dog's collar and had a thick metal ring set into each side.
She reached up and pulled my hair back so she could fit the collar around
my neck. I heard a loud click as she snapped the lock shut.
'I have some wonderful news for you Charlotte'.
Even in my heels Mistress Diane was a full three inches taller than me.
She beamed down.
'I talked to your Mistress this afternoon. She's agreed that you can help
us out for a few hours in return for your lovely new uniform. So you can
get behind the counter with Molly! Isn't that lovely? I want to see hard
work mind. I don't want you two girls gossiping all night and ignoring the
customers. We close at 9:00 tonight - lots of work to do'.
She must have seen the expression on my face.
'Of course you don't have to stay. You're free to go if you want. No-one
around here will take any notice if you walk down the street in that
outfit. You might have some trouble getting on the train in the rush hour
though. All those crowds. Bound to crease your dress. If you're lucky
some nice strong young man will look after you...'
There was the sound of cackling laughter from the shoppers. What could I
do? Head down I walked over to the counter to join Molly.
In the end it wasn't nearly as bad as I feared. The customers were mostly
respectful and I quickly learnt to deal with the few that did try and feel
me up. There were plenty of mirrors in the shop and each time I saw this
sexy young girl strolling round in her skimpy outfit my confidence grew. I
also realised very quickly that most of the customers were afraid of me. I
knew I was convincing, and they seemed to see me as a totally feminine
image of all their fantasies. Most of them couldn't help thinking about
what they'd like to do to me. As a result they were blushing and hesitant
and usually talking straight to my chest. I exploited this balance of
power without mercy by flirting with every customer that looked halfway
presentable. I can't describe the feeling that came over me when some
blushing young teenager came over and asked for something. It sent a
thrill down my spine. Of course, not all customers were easy to deal with.
One in particular spent at least 30 minutes bullying Molly when she didn't
curtsey quick enough. He was fat and middle aged with a cruel face and I
remember being glad I didn't have to deal with him.
Soon it was 9:00 and Mistress Diane let out the last customers and bolted
the doors. I was so glad to see that door shut, Molly had been sent off to
do something for Mistress Diane about 30 minutes ago and I had been rushed
off my feet trying to cope with all the customers. I turned expectantly.
'May I go and get changed now please?'
Mistress Diane glowered at me. Several times during the evening she had
told me off for flirting with customers.
'Come with me first slut. I have a job for you'.
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