Sissy in the City

Discussion in 'Member fiction' started by sissy_charlotte, Jun 6, 2010.

  1. sissy_charlotte

    sissy_charlotte [url=http://www.chastitym

    May 8, 2010
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    Sissy In The City

    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 three
    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

    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 Maid's 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, four 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 with 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
    they got 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 girls 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 me 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

    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
    erection. 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 five
    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 three or four 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

    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 four inch
    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 three 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
    Maid's 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
    June 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 sawed 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 three 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 been under there for hours! The
    women all thought this was hilarious and clapped
    every time we managed to bring one of them to

    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!
  2. Amber

    Amber Senior Member

    Apr 21, 2009
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    1:15 AM

    I loved reading this!!

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