Date: Mon, 9 Apr 2001 20:00:41 GMT
From: sissy_charlotte@sissify.com
Subject: Sissy in the City (tg section)

SISSY IN THE CITY

by Charlotte
sissy_charlotte@sissify.com


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 bypass this story. Permission is granted to
download, photocopy, copy and repost so long as any such action
contains these disclaimers, and no attempt is made to profit from
this story.


I am a 29-year-old guy living in England.  In most respects I have a
normal life.  I think readers might be interested in me because 10
years ago I spent 3 months in California on a work visa program.
Lots of students have been on these programs over the years but I
think I must have been the first one to spend the summer as a
waitress and sex toy of a rich businessman.

When I arrived in California I already had a room booked at a cheap,
run down hotel in the centre of LA. I didn't have a job yet but I
wasn't worried because I had a lot of money with me. A few days after
I arrived I was on my way back to the hotel one night when I saw a
sign for a transvestite club.  I'd always been turned on by the idea
of dressing in girl's clothes but never had the guts to do anything
about it.  Eventually I decided to go in and take a look around.  The
first thing I saw when I walked through the door was a group of
gorgeous women dressed as waitresses.  They were wearing very skimpy
black satin French Maids uniforms with white piping. The uniforms had
a short skirt and low cut top and were worn with sheer stockings with
seems running up the back, 4 inch spiked heels, layers and layers of
white petticoats to push out their skirts, black elbow length gloves,
a black choker, mop cap and a large white frilly apron tied with a
big bow at the back. I must have stood there with my mouth open for
30 seconds. I realized they were guys but I couldn't get over how
good they looked.

Eventually I found my way to the bar and after a few drinks I started
chatting to one of the waitresses.  As I was obviously a foreigner on
my own she started asking me about myself.  I figured that I was
8,000 miles away from home and unlikely to run into anyone who knew
me so I was totally honest (plus I'd had a few drinks by now!)  I
told her how I'd always been turned on by the idea of dressing like
her but never had the courage to do anything about it. Sophie
immediately called over her friends to hear my story, it turned out
that most of the girls shared a house a few miles away and my fate
was decided!  As soon as their shift was over I was taken back to
their house to play dress up. I had a few more drinks when we arrived
for courage and soon found myself dressed in a corset, stockings,
white blouse, black pencil skirt, low heels, make up and wig.  I was
amazed when I looked in the mirror, I always thought I'd look like
a guy in a dress but they had made me look just like a young career
woman.  I was thin, weedy and short as a guy but I looked really hot
as a girl.  Dressed like that I obviously needed a female name and
they christened me Charlotte.

Pretty soon I was spending as much time as I could at their house. I
borrowed clothes from all the girls and was soon accepted as one of
them. It took me a little while to get the voice right but if I was
careful I could pass as a woman.  After a few days they even managed
to persuade me to go out with them while dressed, once I realized
nobody knew I was a guy I had a great time. A few nights later I was
at the club with them wearing a beautiful green silk dress with very
high heels when they introduced me to their supervisor.  He was so
impressed he offered me work covering for one of the waitresses who
had twisted her ankle. At first I was scared by the idea - going out
dressed in the evenings was one thing but I wasn't sure I could cope
with wearing such a revealing uniform and being hit on by customers
all the time.  The girls soon talked me round, they pointed out that
the dress I was wearing that night was pretty skimpy plus I really
needed to get some paid work. Eventually I agreed with the supervisor
that I would try out the following night and see how I did.  The
girls were thrilled with the news and the next day took me out for a
manicure and a haircut.  My hair was quite long for a guy but theygot
the hairdresser to give me a very cute bob. I wasn't too worried at
the time as I figured it meant I wouldn't have to wear a wig while
working.  It was only later that I realized I would now have to stay
as a girl all the time as there was no way I could comb my hair into
a more masculine style.  They also took me shopping and I got a few
outfits of my own so I wouldn't have to keep borrowing from them.

That night as I dressed in my sexy uniform for the first time my
heart was in my mouth.  I really didn't know what I was letting
myself in for. I loved the way the uniform made me feel so feminine
and vulnerable but I didn't know how I would deal with the attention
it would attract. The girl encouraged me by telling me I looked
fantastic but I made a lot of silly mistakes with my first few
customers. There were a lot of hands on my ass as I took orders but I
learnt to brush them away.  By the end of the night I was exhausted
(I wasn't used to wearing stilettos for that long) but I had to admit
I wanted to do it again. The supervisor agreed and I signed up for
the next ten days.

It was really strange going back to the hotel wearing a dress but
nobody seemed to realize I was a guy.  I soon got used to sleeping
till noon and working at the club until the early hours and as the
end of the first week approached I realized how much I would miss it.
That's when Ramon walked in (I've changed his name).  Ramon was a
tall, good-looking Arab who already knew most of the other girls.  I
couldn't take my eyes off him and he spent most of the night chatting
with me.  It turned out he was a businessman, when I asked Caroline
about him she just laughed and told he he had been out with some of
the girls and was a 'bit kinky'.  He was obviously interested in me
though; when I went back over he asked me if I would have a drink
with him after my shift finished.  I was thrilled, I rushed through
the rest of my work and all the girls were giggling and teasing me
about how I'd pulled big time.  I'd come in that day in jeans and a
sweatshirt so I borrowed a little black cocktail dress from Suzie and
went out for my drink with Ramon.  After about 5 minutes I think
I would have done anything he asked.  I thought his stories were
fascinating and I was totally captivated.  We danced for a bit and
then he leaned over and whispered that his car was outside and did I
want to come back to his house?  Needless to say it didn't take much
to persuade me.  I got a real shock when I saw his car - it was a
huge limo with a bodyguard in the front.  We settled into the back
and he showed me the bar.  It seems really strange to say but
until that point I had never had a homosexual thought in my life.
After a few drinks however I found myself kissing another guy for the
first time ever and pretty soon Ramon guided my head down onto his
cock and I found myself giving my first blowjob.  Thinking back it
felt like a natural step. With everything that had happened to me
recently I felt totally comfortable in my role as the girl doing
everything possible to please her man. I even managed to swallow!

When we arrived at his house I got my second shock of the night.  It
was a large mansion set in its own grounds with guards on the gate.
We stumbled through the front door with Ramon's hands all over me. He
soon found the zip on my dress and by the time we got to his bedroom
I was down to my corset, knickers, stockings and heels.  I was having
a really hard time with the buttons on his shirt, the girls had put
false nails on me and I couldn't grip anything. Soon he was naked and
I got my first real look at Ramon's cock. It was massive, much bigger
than mine and it was rock hard. Then I felt Ramon gently bend me
over, apply a sticky goo to my ass and very gently enter me.  At
first the pain was unbearable and I thought he would split me in
half.  Then it began to ease and waves of pleasure overtook me. I
could feel Ramon's balls slapping against my ass as he rode me and I
tried to control my muscles to give him the tightest possible ride.
His orgasm tipped me over the edge and we both came together, with
him filling me up.  Afterwards I was lying on the bed exhausted and
Ramon got up to go to the bathroom.  When he came back he was
carrying something but I was to weak to turn my head and see what it
was.  It was then that I got my third surprise of the night and found
out why Caroline had called him kinky.  Ramon lifted me onto his lap
and began to spank me.  I was too shocked to struggle but after half
a dozen really hard slaps I began to scream.  He didn't stop until
I'd taken at least 20, by which time I was sobbing quietly.  Ramon
then lifted up the object he had just collected and fitted it around
my waist.  As he clicked the lock shut I realized it was a chastity
belt.

I was so shocked I just looked at him with my mouth open for 10
seconds. Eventually Ramon laughed and reached over to stroke my hair.
He told me I was his little sissy whore now and I would have to wear
the chastity belt to make sure I only thought sweet, girlish thoughts
and didn't stray from my man.  I was amazed but more turned on than
I'd ever been that this man had taken control of me in such an
intimate way. Suddenly I winced as the belt did its work, Ramon just
laughed again and told me I'd get used to it. If I pleased him he
would allow me short periods of relief.  As I got dressed again I
tugged at the leather band of the chastity belt but couldn't shift
it. Eventually Ramon got his driver to take me back to the hotel. As
I sat in the back I wriggled around trying to get comfortable and
coming to terms with the fact that Ramon now controlled my sexual
pleasure.

When I woke up the next day I thought it was all a dream at first -
until I felt the metal tube cut off my errection.  The girls crowded
round me when I walked in the club, demanding to know what had
happened. Shyly I lifted my skirt to show them. Of course they all
thought it was hilarious.  Ramon showed up early that night and was
very attentive.  The chastity belt was really frustrating; I was
desperate for relief and probably would have done anything he asked.
He added to my frustration by teasing me by waving the key in front
of me.  We went out again after my shift; he did take the chastity
belt off for a short period like he promised but only after I had
spent half an hour on my knees giving him another blowjob.

The next night was my last night at the club and Ramon said he would
let me go out with the girls afterwards but he wanted to go to dinner
with me the following night.  I got back to my hotel really late and
was woken by a knock on my door at 8:00AM.  It was John (Ramon's
driver). He handed me two packages and told me I was to be ready for
dinner at 7:00PM wearing exactly what was in the bags.  After he had
gone I had a look and found a beautiful white full-length evening
dress with spaghetti straps, low front and a straight skirt with a
split up one side almost to the waist.  I would have to be careful
wearing that or everyone would see my chastity belt!  There was also
a corset, knickers, stockings and 5 inch spike heels.  I spent most
of the day getting ready for my date with Ramon, starting with a long
luxurious bubble bath and another shave to make sure my body was
totally free of hair. Eventually I squeezed into the corset and
zipped the dress up. John knocked on my door again at 7:00PM sharp
and I stood up to go.  Even though he had hardly acknowledged my
existence before he smiled broadly when he saw me and told me I
'looked great'. I was feeling a little exposed so I picked up a wrap.
John immediately took it out of my hands telling me that Ramon's
instructions had been very specific. I was to wear only the clothes I
had been given.

Needless to say there were lots of people staring at me as I walked
out of the hotel. I even attracted a wolf whistle.  John just smiled
and steered me to the car. Ramon was already at the restaurant and
stood up to greet me. I could feel his eyes all over me and blushed
deep red. Dinner was lovely, Ramon kept telling me how beautiful I
looked. Towards the end he told me he had a surprise but first he
wanted to test my devotion.  He told me to go to the Ladies, remove
my knickers and hand them to him.  I was so much under his spell by
then I just did as I was told without question. I felt a little
thrill as I realized Ramon had demonstrated his complete mastery over
me again.  When I sat down Ramon told me his surprise.  As I was now
unemployed he wanted me to move in to his house.  He would pay me
pocket money and in return I would be at his side whenever he wanted.
He told me that while we had been eating his staff had packed all my
things and settled the hotel bill.  He gave no thought to the
possibility that I might not agree - I was coming home with him that
night.  As we drove back to the house I reflected that a few short
weeks ago I had been just another guy.  Now I was dressed as a
beautiful woman being driven to the house of this man who had just
taken ownership of me, as though my wishes did not matter.  This
really was my fantasy come true, I was so turned on by the fact that
I didn't know where this was heading and had no control over events.
Ramon was obviously turned on as well; we had some of our best sex
ever that night. We started in the kitchen and I think I was screwed
in most rooms in the house. I must have kept the staff awake into the
small hours with my screams of ecstasy.

Ramon spent most of his time away on business trips so I found I was
left alone for 3 or 4 days and then with him constantly for 24 hours.
He had sent someone out shopping to make sure I had a fully stocked
wardrobe, although I noticed I didn't have any trousers or shoes
without heels.  It was also clear there was no way Ramon's staff
would let me leave the compound; everything would be brought in for
me.  One day about a week later Caroline and Suzie came to visit
me.  Ramon had put me on a strict diet and they were amazed at how
much weight I had lost. We were sitting around laughing and chatting
when Ramon rang to tell me he would be home in a few hours. While he
was away I got to dress in more comfortable clothes but he liked me
to dress as sexy as possible when he was around.  This time he
instructed me to go and remove the loose summer dress I had on and
change into a white blouse, a very short and tight black leather
miniskirt, sheer stockings and 4" strappy sandals.  Of course the
girls teased me and told me I was a good little wife doing what my
husband told me. I didn't care - the chastity belt was driving me
wild with frustration by then. If this was what it took to please
Ramon and get him to unlock me for a few hours then it was worth it.
When he arrived he pulled me to him and kissed me.  He was delighted
to see the girls there; he immediately started teasing me by patting
his crotch and telling me how he had a big present for me. The girls
thought all this was hilarious, especially when Ramon got me to serve
all 3 of them during dinner later. As usual on the nights when he got
back from one of his trips I received many loads of his precious cum
in both ends of my body that night.

Perhaps the strangest thing that happened was a few weeks later just
before I was due to come back to the UK. As you may have realized by
now Ramon had a healthy interest in BDSM and he belonged to a local
Dominants club. Most of the members exercised varying degrees of
control over their slaves and one woman with a house in the hills
outside the city had decided to marry her live in feminized sissy
maid. Ramon had volunteered me as one of the bridesmaids.  As I got
into my dress on the day of the wedding I had some of my worst
jitters ever. I was wearing a full-length cream silk dress with a
tight bodice and straight skirt.  My hair was a lot longer by now and
Ramon arranged for a hairdresser to come in that morning. By the time
he had finished my hair was teased into a very elaborate arrangement
and decorated with flowers.  When we got to the house I found the
other two bridesmaids and bride were already there.  We were put away
in a room on our own while the guests got drunk waiting for the
ceremony to start. They told me all sorts of stories about the way
their Masters treated them and I realized the humiliations Ramon put
me through were mild by comparison. Jane (the bride) had even been
made to serve dinner in a Victorian Maids uniform for two of her ex
girlfriends who her Mistress had tracked down. Throughout the meal
she had been forbidden from talking unless it was in French. One of
the other girls had been made to walk into a bar and offer a blowjob
to the first guy to join her outside.  They asked me about Ramon and
told me they were very jealous my Master was so good looking.  I was
about to object and tell them Ramon was not my Master when I realized
how silly that was.  After all Ramon had subjected me to it was clear
that he owned me body and soul. I had never disagreed or objected to
a single order he had given me and I couldn't see myself starting
now. In a few short weeks he had turned me into an obedient, feminine
creature whose only goal was to make him happy.

It was a lovely sunny day and the ceremony was out in the garden.
The only problem with this was that our heels kept sinking into the
lawn.  Of course Jane had to promise to obey her Mistress and was
made to kneel while a collar was locked around her neck.  After the
ceremony a magician had been booked to entertain the guests.  The
bridesmaids had to serve drinks while Jane was made to change into a
gold lame bikini and heels and act as the assistant to the magician.
The poor girl was sawn in two, made to disappear and shut into a box
which the magician then stuck swords into.  At the end of the final
trick Jane found herself in handcuffs chained to a ring in the ground
without the top half of her bikini. She was just left there for 30
minutes while all the guests crowded around feeling her up.

After we had served dinner Jane's Mistress called the bridesmaids
into a big bedroom at the top of the house. On the bed were 3 gold,
white and red cotton cheerleaders dresses which we were ordered to
change into.  We then put on track shoes and braided each other's
hair into pigtails.  Mistress produced some leg irons and chained the
three of us together. She then locked collars around our necks. Each
of the collars was attached to the others with a short length of
chain.  Once we were securely fastened Mistress led us back
downstairs as we shuffled behind her.  She stopped outside one of the
dining rooms and knocked.  When we entered we saw our owners sitting
around a large table covered with a white tablecloth playing cards.
We were ordered to get under the table and give our owners a blowjob.
We must have bee under there for hours!  The women all thought this
was hilarious and clapped us every time we managed to bring one of
them to orgasm.

Shortly afterwards it was time for me to go home. Ramon never
suggested we had a long-term future together, he always told me he
would let me go when the time came.  Even so he was determined to
keep me under control for as long as possible.  I was allowed to get
a hair cut and dress in t-shirt, jeans, trainers and jacket for the
journey to the airport but he made me wear a corset, knickers and
suspenders underneath and would not release me from my chastity belt.
He also made sure all my clothes were packed in the suitcase so
I would not be able to change during the flight. When the time came
to say goodbye he kissed me on the lips in front of all the other
passengers and handed me a key.  Then he walked off.

I ended up undressing in the toilet on the aircraft and leaving my
lingerie in the rubbish bin.  Luckily the key he gave me was for the
chastity belt so I was finally able to remove that too.  I've often
wondered what the cleaners must have thought when they found all that
sexy underwear and a chastity belt when they were cleaning the plane!


I hope everyone enjoyed the story; it is my first effort. I welcome
any comments or suggestions.