Sissy's Back In The City

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  1. sissy_charlotte

    sissy_charlotte [url=http://www.chastitym

    May 8, 2010
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    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.

    This is the second part of Sissy in the City.

    As the aircraft banked over the Northern California coast a stewardess announced
    we would be landing in thirty minutes. I rose from my seat and walked to the toilet
    carrying my hand luggage. It was time to get ready! As I locked the door behind me
    I pulled a small cardboard box out of my bag and gingerly opened it. I carefully
    lifted the tissue paper to reveal the delicate lingerie I had bought the previous week.
    The girl who served me thought it was a gift for my girlfriend and she had sprinkled
    some rose petals in the box. Now, a week later, the feminine smell almost
    overpowered me as I held the panties to my face. I quickly removed my tracksuit
    and very carefully fastened the suspender belt around my waist and pulled the sheer
    stockings up my newly shaved legs. I paused as I felt my cock begin to respond - it
    had been a long time since I had been able to wear something so soft and feminine.

    Quickly now I found the french cut black silk panties and pulled them up my legs. I
    fastened the bra around my chest with the hooks in front of me before pulling it
    round and slipping the straps over my shoulder. By now my cock was ramrod hard
    and I realised I would have to do something about it if I was going to be able to put
    on the last item. I wasn't looking forward to this but my instructions had been very
    clear, I had to be wearing everything he sent me when I arrived or I would be on the
    first flight home.

    As fast as I could I jerked off into the pan. It didn't take much because I was so
    turned on by the thought of what would be happening to me in the next few hours.
    Then I reached into the bag again and pulled out a metal tube with a leather harness
    fitted around it and a lock at the front. I lowered my panties and carefully fitted my
    flaccid penis into the tube and stretched the leather belt around my waist until it met
    the strap between my legs. I took a deep breath and counted to five before clicking
    the lock shut. There was no going back now. The only person with a key to the
    chastity belt was Ramon, my Master and the man who would be meeting me at the
    airport in a few minutes. I checked to make sure my stockings were straight before
    slipping my tracksuit back on, flushing the toilet and walking back to my seat.

    As I settled back into my seat I thought of Ramon and everything that had happened
    the previous year. Twelve months ago I had been a student in California on a 3
    month work visa. I'd always been keen to explore my feminine side and when the
    chance had come up to work as a waitress in a transvestite club I had gone for it.
    Ramon had met me there and immediately recognised my submissive, darker needs.
    He had claimed ownership of me, moving me into his villa outside LA and exerting
    control over every part of my life. He even controlled how I dressed, making sure I
    was always wore skimpy ultra feminine outfits. He transformed me from a shy
    teenage boy into a submissive slut. By the time I left to go back to my final year at
    College I was totally under his spell.

    I had thought I could just walk away at the end of the summer but I quickly found I
    could not. Ramon had awakened a need in me and even in the aircraft on the way
    home I realised how difficult it would be to go back to my normal existence, wearing
    rough male clothes and taking responsibility for my own decisions. I began to
    experiment, spending hundreds of pounds on visiting Doms in London. None of
    them came close to what Ramon had given me and I began to feel I would never find
    another Master like him. Eventually I accepted my fate, there was no chance of me
    ever seeing Ramon again.

    Then, one morning just after Christmas, I saw a letter with a California postmark on
    my front door mat. It could only be from one person and I found my hands where
    shaking as I tore it open. I began to read;


    I have given a lot of thought to this letter. When I met you last year I thought you
    were just another sissy slut who needed my guidance to bring out your true feelings
    and abilities. I have met dozens of similar girls in the past and each time I eventually
    allow them to return to their previous lives. I look upon it as training, a short term
    arrangement of mutual benefit. I have never looked for a longer reltionship. Until

    In your short time with me you exhibited remarkable ability. You submitted
    willingly to my authority and I was able to quickly bring you to a level of
    submission that took other sissys weeks to reach. You immediately recognised what
    you were - a sissy slut under my total control. Most fight the truth when they are
    faced with it, you embraced it with none of the tantrums I am used to. That it why I
    am about to make an exception to my rule. I want to fly you back to California this

    This time our relationship will be different. I am not looking for another girlfriend, if
    you return it will be as my maid. You will have to accept me as your Master. I will
    provide for you in every way and dress you in clothes that will make every man
    desire you. After a short trial period you will begin taking hormones and I will pay
    for operations to turn you into a beautiful wanton slut.

    Be warned, discipline will be harsh and you will have to accept that I own you in
    every way. Body and soul. Your status will be low. You will be my slave. If I am
    right there is no decision for you to make, this is what you have been longing for
    since you left me six months ago.

    Understand one thing, if you have any doubts at all you should not return. If you do
    accept my offer it means accepting a new harsh and cruel existence where your only
    purpose will be to please me and you will be severely disciplined if you fail. Think
    carefully before replying.

    Best Wishes


    I stood staring at the letter with my mouth open. Could it really be happening?
    Ramon was inviting me to change my life. If I went through with this I would have
    to leave my life in England (such as it was) behind for ever. There could be no
    second thoughts, I would be turned into a feminised sissy slave and would live the
    rest of my life according to Ramon's wishes.

    The next day was Sunday and I went for a long walk. I couldn't sleep so I left my
    flat at 4:00 in the morning and did not return until after dark that night. I just
    wondered around and around and around thinking about Ramon's offer and what it
    would mean to me. I kept coming back to one fact. I had never felt happier or more
    fulfilled than when I was with Ramon. I ached to be back in the short skirts and
    heels he had dressed me in and to be subject to his every whim. I worshiped him in
    every way and truly saw him as my Master. On Monday morning I wrote a carefully
    worded letter accepting his offer.

    Over the next few months we exchanged several more letters. It was agreed that I
    would stay at College and take my final exams in June. I would fly out immediately
    afterwards for an initial trial period of two months. I would have to come to San
    Francisco airport this time as Ramon was living in a property he owned in the hills
    for a few months while he negotiated a business deal. After my trial period we
    would both consider my future and if I still wanted to proceed I would sign a
    contract of slavery. I would become Ramon's property, to do with as he wished. I
    was immediately put on a strict diet and told what I was to bring with me and what I
    was to wear for the journey.

    As I walked through the terminal after landing I could feel the soft pull of my
    stockings against the suspender belt. I imagined that everyone must be able to see
    what I was wearing and I blushed deep red. Going through Customs was reasonably
    quick, although the officer did keep asking me if I was feeling OK. I collected my
    one small suitcase and walked into the Arrivals Hall where I knew Ramon would be
    waiting for me. As I got closer my ears began to roar and my vision narrowed until I
    could no longer see the crowds milling around. Desperate, I spun around. I couldn't
    see him! He wasn't here! There were too many people. Then I looked over at a small
    coffee shop on the far side of the hall. Sitting at one of the tables smiling at me was

    My legs turned to jelly and I swayed slightly. As quickly as I could I walked over to
    him and, as instructed, dropped to my knees in front of him.

    'Your slave Charlotte is here Master. I beg to serve you.'

    Ramon ignored me for a few seconds and then bent down and spoke softly into my

    'Say it LOUDER slut'.

    I blushed as people began to stare at me and laugh. Quickly I repeated my lines as
    loudly as I could. There was another long pause and then Ramon stood up and
    signalled for me to follow him. Obediently I trailed behind him carrying my one
    small bag as we headed out of the airport into one of the huge car parks. We seemed
    to be walking for ages but eventually we stopped by a top of the line Range Rover.
    Ramon turned to speak to me again;

    'Take off your tracksuit. I want to see if you are dressed as I instructed'.

    I was shocked. He wanted me to strip in the carpark! It was dusk now and there
    were few people around but the idea of standing in this car park wearing just my
    ultra feminine underwear was incredibly humiliating. Ramon noticed by hesitation;

    'Do it now slut. Or I'll strip you myself and leave you here. I hope you took my
    warnings seriously, this is nothing compared to the treatment you can expect'.

    I had no choice and I knew it. I began to strip and was soon standing on the cold
    concrete floor in my lingerie and chastity belt. Ramon looked me up and down.
    Then he smiled. My heart leapt as I saw him smile and knew that I had pleased him.
    He opened the tailgate of the Land Rover and signalled for me to climb in the back.
    The rear of the car was a large mesh cage of the sort used to transport large dogs.
    When I was in the cage he locked it shut and then shut the car boot. He climbed into
    the drivers seat and drove off.

    Luckily the windows in the back were quite high and I found that if I rolled next to
    them I could only be seen by cars right alongside ours. Even so I heard a few
    shouted comments as we travelled along the freeway. We drove for hours, heading
    out of the city and into the hills. Eventually I felt the car stop as some gates opened.
    We were here. The car headed up a long tree lined gravel drive and stopped outside
    a large villa. The design reminded me of the ranch houses you sometimes see in
    Westerns. It was two floors high and painted white. There was a large lawn (about
    500 foot) out front.

    Ramon opened the cage to let me out and I followed him into my new home. He
    walked upstairs to one of the bedrooms and turned to face me. He looked me up and
    down, as if he was appraising a new work of art he had just bought. Then he smiled
    again and ran his hands over my tummy.

    ' I've missed you Charlotte. I am so glad you came back. we're going to have so
    much fun together. I've missed your cocksucking lips and slut's body. You have lost
    a lot of weight my dear. That's good, it shows you have been following my orders. I
    want you to put on your uniform now. It's in the closet over there. When you've
    finished come downstairs and find me'.

    When he had gone I walked over to the closet and opened it. Hanging in it was a
    French Maid's uniform. I ran my hands up and down it, feeling the smooth silk
    between my fingers. I noticed there was some makeup on the dressing table by the
    window and shoes and underwear on the floor by the closet. I had lost so much
    weight I didn't really need a corset so to save time I put on a short slip that had been
    left out for me. I sat down at the dressing table to do my makeup, applying heavy
    blusher, mascara and a deep red lipstick to highlight my cocksucking lips. I found
    some strappy black sandals with a 4" heel and sat on the bed to put them on. I was
    unused to wearing heels and I stumbled slightly as I stood up. I walked up and
    down the room to get back into practise, I caught sight of my reflection in the mirror
    and instantly gave myself a hard on admiring the shape of my legs in the heels. This
    was a mistake, the chastity belt cut off the blood supply to my cock and I winced as
    the pain shot through me. In spite of the pain I purred softly to myself, I loved the
    fact that the only way I was going to get any relief tonight was by pleasing Ramon.

    I lifted the dress out on its hanger. It was black silk with a narrow waist, very small
    skirt and full length sleeves. With trembling hands I unzipped it and stepped in, in
    spite of all the weight I had lost it fit me like a second skin and I had to really
    breathe in to zip it up. I picked up some white lace underskirts, stepped into them
    and pulled them up to my waist. They peaked out from under the skirt and pushed it
    out so my stocking tops could clearly be seen. Next I found a large white apron and
    tied it around my waist with a large bow at the back. Finally I sat down at the
    dressing table and teased my hair out into a more feminine style. I had kept it
    shoulder length for most of the year and with help from a little mousse I was able to
    come up with a very stylish look. After carefully pinned a mop cap to my hair with
    the aid of some hair grips I stood up to inspect myself in the mirror. Staring back at
    me was a sexy little minx dressed in one of the most alluring outfits I had ever seen.
    Ramon wasn't going to be able to keep his hands off me! All the thoughts I had had
    the previous year came flooding back to me. I loved the way this outfit made me feel,
    dressed like this I was the submissive plaything of my Master.

    I found Ramon sitting on a sofa downstairs in the front room. I executed a perfect
    curtsy for him and asked if I could be of service. He was clearly impressed, he ran
    his eyes up and down my body taking in every curve. Eventually he spoke.

    'Delightful my dear, even better than I had hoped. In time we will make you a
    stunning beauty. For now, I want to see if you have remembered what I taught you
    last year. Come and kneel between my feet'.

    I blushed and slipped to my knees between my Master's legs. Now the time had
    finally arrived I was worried that I had forgotten too much over the last 12 months,
    worried that I would make some silly mistake which would anger him. Very
    carefully I reached up, unzipped his pants and pulled his cock out. I gently
    massaged it, watching in wonder as it grew to my touch. It looked even longer than I
    remembered! Carefully I opened my moist red lips as wide as I could and slipped
    his wonderful cock into my mouth. It banged against the back of my throat but I
    managed to swallow it all. Very gently I closed my lips and began to suck.

    In and out, faster and faster I ran his cock over my lips. It felt totally natural,
    kneeling there pleasing my man as his balls banged against my chin. His cock grew
    even bigger as blood and cum flooded in. I almost choked. I didn't care, I was lost in
    the moment. I ran my tongue along the underside, stopping to circle that spot just
    below the head. Faster and faster I went, as I used one hand to cup his balls.
    Suddenly I tasted his pre cum dribbling down my throat, how I had missed the salty

    Ramon began to groan louder and louder, suddenly seizing my head with both
    hands and forcing me deeper onto his cock. Now his cock was half way down my
    throat and I was feeling alternating pain and ecstasy as my own little sissy clitty (as
    Ramon liked me to call it) strained in its metal prison. Suddenly Ramon exploded
    and I felt hot, sticky cum flooding down my throat. Desperately I swallowed as fast
    as I could but I could feel cum dribbling down my chin.

    Eventually he was done and I collapsed in a heap on the floor, looking up at my

    Master. Ramon laughed as he played with my hair. He was pleased that I had
    remembered most of what I had been taught and I blushed at his praise. Then he
    rose and commanded me to follow him. He led me into the kitchen and then
    unlocked a heavy iron grill covering a doorway. He led me down some stone steps
    into a dark basement.

    'It is time for you to meet your playmate'.

    As my eyes adjusted to the dark I could see we were in a dungeon. There were
    whips and chains along the walls and a large flogging horse and many other torture
    devices in the room. In the corner was a low box covered by a dark sheet. Ramon
    walked over to the box, theatrically raised the sheet and tossed it to one side so I
    could see it was actually a cage. Lying in the cage was a woman dressed head to toe
    in a one piece black latex catsuit. Around her neck was a leather collar secured to the
    bars with a short length of chain. Her head was covered by a latex mask with slits
    for the mouth and eyes and a zip across the crown, which was locked to the catsuit
    under her collar. Her hands were secured in mittans with no fingers or thumbs. She
    was also wearing 5" spikes which appeared to be part of the catsuit.

    She looked up startled as the light hit her and I saw a tail hanging between her legs.
    Ramon unlocked the end of the cage and fastened a lead around her collar to pull
    her out. I realised she was dressed as a cat, with little pointy ears on her head. As
    she shuffled out of the cage on hands and knees she meow'ed and rubbed herself
    against Ramon's leg. He laughed delightedly and patted her ass;

    'Charlotte, this delightful creature is Rebecca. When she is not my household pet
    she is my devoted slave. Unlike you she is not a sissy, she was actually born female.
    You two will get to know each other very well. I have very few rules, Rebecca will fill
    you in on the details but in summary I expect you to do absolutely anything I order
    immediately and without hesitation. Any problems with any aspect of your daily
    duties will be harshly punished and Rebecca will tell you that I have some very
    ingenious punishments. Your purpose here is solely to please me, to concentrate
    your minds I insist that you both wear chastity belts. I am not averse to releasing
    you for a short time if you show particular devotion but your sexual happiness will
    always be controlled by me. I may choose to give you to someone else it will never -
    underline never - be another one of my slaves. Rebecca is strictly out of bounds for
    you, if I was ever to catch either of you without my permission I would sell you both

    For now I will leave you to get better acquainted - have my dinner on the table at

    With that he handed me the key to her collar and turned and left us alone. I was
    amazed, I had never considered the possibility that Ramon would have another slave.
    I unlocked Rebecca's collar and helped her pull off the mask, she looked a bit hot as
    she shook out her long blonde hair. She looked just like a cheerleader from high

    'Hi babe. He told me you were coming back a couple of weeks ago. He's talked
    about you constantly, about his plans to make you my sister. You look gorgeous
    already honey'.

    I laughed nervously. For the next 30 minutes we just talked, Rebecca told me how
    much she had heard about me and how much she was looking forward to meeting

    I learnt that until 6 months ago she had been a student at UCLA. She had met
    Ramon at a club and he had given her a chance to fulfil her submissive tendencies. A
    month ago he made her sign a contract of slavery. Although she still attended
    College she now spent most of her spare time serving Ramon and being humiliated
    by him.

    The dungeon was larger than I realised and Rebecca showed me a small side room
    containing stalls similar to those in stables for horses. Each contained a metal bed
    with a thin mattress and she explained that this is where we would be living. There
    were some wardrobes against the wall containing our uniforms (shared, of course!)
    and a small bathroom to one side. We chatted as Rebecca changed into a maids
    uniform similar to mine. Watching her change was a mistake, she had a gorgeous
    body and I soon had a painful reminder of my chastity belt. Although I thought I
    was pretty sexy in my uniform she was amazing! It was all I could do not to stare at

    She led me up to the kitchen to start preparing dinner. We were chatting away like
    two sisters by now, heels clicking on the stone floor as we walked up the stairs.
    Ramon was standing in the kitchen fixing himself a drink and we immediately
    dropped our eyes and curtsied. Rebecca had warned me that this was one of the
    house rules. Our Master also appeared to be taken by the site of Rebecca is her
    skimpy uniform but he soon left us again so we busied ourselves preparing dinner.
    Rebecca warned me that we were not allowed to eat anything until after Ramon, he
    would whip us if he caught us picking at his food.

    After we had served dinner we chatted in the kitchen as we cleared up and ate our
    own meals. Ramon had a bell in the front room which he rang if he wanted anything
    and we took turns serving him. I had already slipped back into my role as the
    subservient feminine slave and it felt totally natural to be at the beck and call of this
    man. The reality of my position was brought home to me as we were finishing up.
    Rebecca suddenly went quiet and I realised Ramon must have entered the room.
    Before I could turn round I felt strong hands on my waist. I was lifted up onto the
    worktop, still on my front. Ramon didn't say a word but he grunted as he pulled my
    knickers down. I felt his fingers begin to explore my hole, probing and feeling. He
    signalled to Rebecca to carry on working and I could see her busy drying plates out
    of the corner of my eye. Ramon was fumbling with his pants, he still hadn't said a
    word. He bent me forward even further and I felt his hot, warm cock against my ass.
    This was an incredible turn on for me. Here was this man treating me as his sexual
    toy. He began to enter me, because he hadn't lubricated himself it was incredibly
    painful at first. Then he began to pump deep into me, filling me up until I thought
    my ass would split in two. I began to moan softly as I clenched my muscles to ride
    my Master. He was thrusting into me faster and faster now, pushing me into the
    workbench. I could feel his cock growing, ramrod straight as it penetrated me.
    Suddenly he exploded, filling me up with his hot cum. I had my own little sissy
    orgasm at the same time, the experience of being used like that was so erotic.

    When he was done Ramon just zipped himself up and strolled out of the room. I
    was lying on the floor, too exhausted to move. Rebecca had started playing with
    herself as soon as Ramon left. She looked down at me;

    'You lucky, lucky bitch. It's going to be SO much fun having you around here'.

    We soon fell into a routine. The metal grill on our basement home had a timelock,
    each night Ramon locked us in and each morning we rose at 5:30AM in order to put
    on our uniforms, make ourselves pretty and prepare breakfast for our Master.
    Ramon's standards were very high, I was frequently canned in those first few weeks
    because the seems on my stockings were not straight, or my opera pumps were
    scuffed or my hair had a tangle in it. Ramon liked to eat well but we had to make do
    with scraps - one of his favourite sayings was that a fat maid was no good to him.

    He spent weekdays at the office but even then we were not free. On most days we
    were secured by chains to radiators or pipes with only enough chain to reach the
    areas of the house we were working in. Rebecca was often away for 3 or 4 days at
    once at College so this could get very dull. One day he made me drink 3 pints of
    water before he left and fixed the chain so I could almost - but not quite - reach the
    bathroom. He told me that I could pee in the flowerpot if I needed to but if I did he
    would make me drink it when he got back. That was one of his hardest tests, I tried
    my best but I couldn't hold it in. He did make me drink my pee when he returned
    and it was horrible. He sometimes gave Rebecca a golden shower but he never made
    me drink his urine, which was something I was very glad about.

    By this time I had slipped back quite happily into my old life, but occasionally
    Ramon reminded me that there was a world full of normal people outside the villa

    One weekend I prepared a salad for his lunch. I didn't realise the dressing was off
    so I took it through for him as normal. He covered the salad in dressing and
    immediately spat out the first mouthful. His meal was ruined and I knew I was in
    big trouble. Like a fool I tried to justify myself by telling him we didn't have any
    other dressing in the house. His punishment was to take me shopping. Normally
    when I had to go out shopping I was allowed to change into a normal dress or skirt
    and blouse. This time he made me go in my uniform. He made me climb into his car
    wearing my skimpy little French Maid's uniform. stockings and heels. Luckily he
    didn't take me to the local store I normally used, instead we went to a large
    supermarket about five miles away. My face was burning red as we walked in!
    Everyone was staring and some lads even started trying to chat me up. There were
    kids playing in one of the aisles and they started chasing me and trying to look up
    my skirt (not difficult!) By the time we had found the salad dressing we were being
    followed by a crowd of about twenty people. Some thought I was doing it for a bet,
    some thought I was mad. The security guard was chatting to Ramon and patted my
    fanny whenever I was close enough. They all assumed I was female and Ramon did
    not set them straight - until we got to the checkout. The girl on the till asked him
    why 'she' was dressed like that.

    'Oh no, Charlotte isn't a real girl. This is a little sissy boy who enjoys dressing in
    pretty clothes'.

    When I heard his reply I wished the ground would open up and swallow me. This
    was so humiliating! The crowd erupted in laughter and I had to run a gauntlet of
    hands trying to pinch my ass on the way back out to the car. Embarrassing as the
    experience was I was incredibly excited by the way Ramon had treated me. He was
    obviously turned on as well, I spent most of the ride back with my head in his lap
    giving him a blowjob.

    Rebecca was back the next day and she thought it was very funny when I told her
    what had happened. She explained that Ramon had once punished her by taking her
    shopping in a baby doll nightie, knickers and high heels. He had stopped twice in
    the woods on the way back to screw her!

    Ramon belonged to a local BDSM club and there was a meeting every few weeks he
    liked to bring us to. Usually he would dress us in some sexy outfit and we would
    have to stand perfectly still for hours at a time while the other members felt us up.
    Slaves were made to put on shows to entertain their owners and I remember one
    where I was a cheerleader dressed in a lovely satin uniform. Our team won their
    game and kidnapped us. We were made to do some disgusting acts before they
    would release us, as a finale the entire team lined up at the front of the stage and
    cheerleaders had to work their way down the line sucking each one off. The
    audience loved it!

    Ramon's turn to host the club coincided with the 21st birthday of two brothers called
    Dean and Bob (although we called them Sir and Sir!). Rebecca and I would be
    serving and we spent all week getting ready. It was a lovely hot summer day and
    most of the guests were out on the lawn. I was serving drinks when Ramon asked
    me to go and wait for him in the bedroom on the second floor.

    When I got there the first thing I saw was Rebecca standing in the middle of the
    room. She was stark naked except for white stay-up stockings, heels, elbow length
    white lace gloves and a satin choker around her neck. All she was wearing around
    her waist was a large white ribbon. It had been doubled up, passed between her legs
    and then around her waist twice before being tied in a large bow behind her. It was
    obvious that all it would take to remove the ribbon was a quick tug on the bow at the
    back. She looked absolutely stunning. When she saw me she blushed.

    'I don't know what he's got planned but I'm feeling a little exposed. I think I'm the
    birthday present'.

    Just then Ramon walked in, we turned and curtsied. He walked over to Rebecca and
    locked a dog collar around her neck. He attached a lead and called me over.

    'Rebecca; from this point on you are forbidden from speaking. Charlotte; We are
    going downstairs now. I want you to take this lead and follow me.'

    Ramon then walked downstairs, with me following him holding Rebecca's lead.
    When the guests saw us they immediately fell silent as 100 eyes explored Rebecca's
    glorious body. Ramon led us through the room and into a smaller dining room that
    was separated from the main room by some screens. I saw there was a large table in
    the middle of the room with a short length of chain attached to the nearside legs. On
    the end of each chain was a handcuff bracelet. I led Rebecca to the table and then
    stood to one side as Ramon removed the screens so the guests could see what was

    As subtly as I could I stole a quick glance at Rebecca's body. Her nipples were as
    large as saucers. She saw me looking and winked. Very quietly she whispered.

    'It's showtime Babe'.

    The guests surged forward so they could see what was happening. Ramon ordered
    Rebecca to spread her legs so that they were next to the nearside table legs. I then
    bent down to snap a bracelet shut on each of those lovely, delicate ankles. Rebecca
    was now facing away from her audience with her legs secured four foot apart.
    Ramon ordered her to stretch forward so that her bare breasts were against the cold
    wood. I was then instructed to cuff her arms to the other two table legs. I snapped
    the handcuff shut over the thin lace covering each wrist. Rebecca was now helpless,
    presenting her most intimate area to the guests with her modesty protected by a thin
    piece of ribbon. I was overcome with jealousy. How I wished to take her place.

    Ramon crossed to a chair on one side of the room and called Dean and Bob over.

    'My friends, this is my present to you both. As a token of our friendship I am
    offering you my slave for the afternoon. Use her in any way you wish.'

    I nearly came on the spot. Better was to come. Ramon patted his lap.

    'You've been working too hard Charlotte. Come and sit down my dear'.

    A ripple of laughter ran through the audience. I turned and saw that Ramon had
    unzipped his pants. He was sitting in an armchair with his marvellous cock standing
    hard and tall in his lap. It was wet and glistening with precum. Despite my training I
    couldn't help squealing with delight. We had been so busy Ramon had not touched
    me for three days. It would be exquisite to be screwed by him in front of all these
    people. I minced over to my Master and daintily slipped off my knickers. I could
    not resist throwing them over my shoulder into the guests. For a moment I thought
    my presumptuous behaviour had angered him but then I saw him smile. Very
    carefully I lowered my ass down onto his cock. I had to use my free hand to guide
    him into me but I was a lot looser than when I arrived so it was quite easy. Suddenly
    I was sitting on Ramon's lap, locked to him by his rock hard cock. I felt him fill me
    up, growing and pushing into me.

    I looked over at Rebecca. Dean was standing behind her and as I watched he ripped
    away the ribbon, exposing her to everyone while Rebecca greedily sucked at Bob's
    cock. She let out a contented groan as Dean entered her from behind and began to
    pump away. Ramon began to rock me gently on his lap and I felt waves and waves
    of pure pleasure cut into the pain as the chastity belt did its work.

    Rebecca looked over at me and we locked eyes. No words were needed as the erotic
    situation overtook us. Dean and Bob came almost immediately, Bob pulled his cock
    out of her mouth at the last moment and showered her face and hair in cum. Rebecca
    was straining against her bonds, swinging her ass desperate for more cock. From
    where I was sitting I could see the cum and sweat glistening as it ran down her leg.
    The boys had swapped ends now Rebecca was working like a mad woman,
    desperate to drain them again. Ramon bucked as he rode me nearer and nearer to
    orgasm. I had lost control by now, gripping him tightly with my thighs as I tried to
    force him deeper into me. I felt him explode, hot cum filling my ass as my own
    sissy orgasm hit me at the same time. For a moment I slumped forward, fastened to
    my Master by his still hard cock. The crowd erupted with wild cheering and
    applause as I screamed in ecstasy.

    From out of the corner of my eye I could see Rebecca with cum dribbling down the
    corner of her chin. Bob and Dean were exhausted, slumped in front of her.
    Eventually I managed to crawl over to the table and release her. Ramon insisted that
    we didn't have time to go and clean ourselves up so Rebecca and I picked up a tray
    and carried on serving the guests. After seeing our display the guests couldn't keep
    their hands off us and my bottom was black and blue by the end of the day. Rebecca
    wasn't allowed to put any more clothes on and served the guests almost naked for
    the rest of the afternoon. Needless to say we were both very popular and there were
    many requests to borrow us to provide the entertainment at the next party.

    One afternoon soon afterwards I was serving Ramon on my own when he signalled
    me to come closer. Nervously I walked over to him, my heels clicking on the bare
    wood floor. As I waited for him to speak I smoothed down my skirt and hoped I
    hadn't earned another punishment.

    'I have a job for you my dear. Over the last few weeks I have been negotiating a
    business deal with an Asian company. I want to partner with them to build a new
    hotel in India. Their senior management are in California next week to sign the
    contract and it is vital to me that everything goes well. To help establish the working
    relationship I have asked them to join me for dinner in the city on their first night
    here. The company is very ~ ahem ~ family orientated and they think I am married.
    That's where you come in.'

    He paused to stroke my stockinged leg before continuing.

    'You will be my wife for the night. I will take you to dinner and we will tell them we
    are man and wife. It wont be difficult for you, you are already highly convincing. No
    one would ever guess you were born a boy, you are a wonderfully feminine creature.
    Normally I would use Rebecca but she will not be here so it has to be you. No
    matter, you will make a very convincing wife. All you have to do is fuss over me and
    treat me like the centre of your universe. And you know how to do that, don't you...?'

    I laughed nervously. If I could pull this off it would show that I really was
    convincing. I would be spending hours in close contact with these men, if anyone
    was going to 'make' me it would be them. At the same time it was a great honour,
    Ramon obviously trusted me enough to rely on my looks to help him secure the
    contract. If the company found out the truth there was no chance they would ever go
    into partnership with him. I was determined to put on the best possible show for my

    The following Saturday Ramon gave me the afternoon off to get ready. He chose
    my clothes for the night, I would be wearing a black crushed velvet cocktail dress,
    sheer stockings and 4 inch spiked heels. I started with a long luxurious bath, before
    carefully shaving all the hair below my head. I plucked my eyebrows to remove
    some of the recent growth and used the dryer to add loads of bangs and curls to my
    hair, before brushing it out into a very feminine arrangement. I pulled the corset as
    tight as I could and sat down to do my make up. Ramon had told me to go for the
    sophisticated look so I contented myself with foundation, mascara and lipstick. The
    dress was very tight and I was glad I was wearing the corset. It gave me the most
    wonderful curves and I could only get the dress on once I had pulled the strings as
    tight as possible. The shoes gave me a lot of trouble, it was almost impossible to do
    up the straps with my long red fingernails. The heel was a lot thinner than I was
    used to and it took me a few moments walking up and down to get used to them.
    They certainly made my ass sway, I caught a glance as I walked out of the room.
    The boys were in for a treat tonight!

    Even Ramon was moved to compliment me, he told me I looked stunning as I came
    down the stairs. I blushed and thanked him. He couldn't keep off me on the way to
    the restaurant, running his hands up and down my legs. We arrived before Ramon's
    guests and went to the basement bar for a drink. Actually, the drink only took a few
    minutes, my Master was so randy by now he dragged me out the fire escape and
    into an alley at the back of the building after a few minutes. I spent the next ten
    minutes on my knees giving Ramon a blowjob. Lucky there was no one else

    When Ramon's business partners did arrive we all went upstairs to have dinner at
    the restaurant. There were no other women there and even though they couldn't keep
    their eyes off me they were perfect gentlemen, holding the door open and pulling the
    chair back for me to sit down. We had invented a story about how I was involved in
    charity work and spent most of my time organising benefits. I found it was more
    difficult than I thought it would be, I was used to not thinking for myself and doing
    whatever I was told without question. Suddenly I found I had to deal with intelligent
    questions and provide thoughtful answers. Ramon had to come to my rescue a lot, I
    think I came across as a bit of an airhead. Our guests where charmed, they thought I
    was just another pretty young wife who had hooked her older man. To be honest
    when they talked about business a lot of it was over my head. I just sat back between
    the men and enjoyed the attention.

    It was obvious even to me that the evening was a success. Although they were more
    than slightly drunk Ramon's guests were smiling and laughing and when they stood
    up to leave they told him they were sure it would be easy to resolve the few
    remaining issues and he would have his contract in the next few days.

    After they had gone I nervously looked at Ramon, he was smiling from ear to ear.
    My heart leapt, my Master was pleased! He kept patting me, telling me how well I
    had done and offering me all sorts of rewards. It was lovely to be sitting there, just
    me and him being praised and told how I had pleased him.

    Suddenly I felt the mood change. Ramon leaned over to me.

    'There is one more thing to discuss my dear. Last Friday was your anniversary. You
    have been back with me for two months. It is time to decide your future.'

    I was shocked, the time had passed so quickly I had completely forgotten I was on
    trial. Ramon continued.

    'I have no doubts about your suitability as a slave. You have slipped back into your
    old life quite naturally and given me a lot of pleasure. However it is your decision as
    well. This is the last point at which I will allow you to express your will. If you stay
    with me it means accepting my wishes - whatever they may be. I may turn you into a
    hooker. I may sell you. You will be expected to accept whatever I decide without
    question, or be punished severely.

    If you stay it also means accepting your physical transformation. You will be
    expected to take hormones and eventually undergo a series of operations until you
    are indistinguishable from a natural woman - apart of course from the one memento
    of your past that I intend to leave you with. You will always have your little sissy
    clitty but in every other aspect you will be female. I will pay for the entire process
    and afterwards I guarantee that you will be the most beautiful creature in any room
    that you walk into. In return I expect absolute and unquestioning loyalty'.

    He paused as he saw the look on my face.

    'Do not be alarmed my dear. Change can be unsettling but this will only happen if
    you want it. Look deep inside yourself. In a few years I can turn you into a woman
    as beautiful as Rebecca. Is that truly what you want?'

    I leaned forward, sobbing. Ramon put his arm around me.

    'Courage my dear. You do not have to decide immediately, I will give you a few days
    to make your mind up'.

    I turned to look up at him, my cheeks wet with tears.

    'You don't understand....I can't imagine any other life than this one. I know what I
    want now. Please....please.....I want this so much'.

    Ramon reached out and hugged me. I was so used to seeing him as untouchable I
    almost recoiled. I had thought long and hard before coming back to the United
    States but now I was here, now I was sitting next to my Master dressed as a
    beautiful woman I knew I could never go back to my old life. I wanted to be
    transformed - I wanted to live the rest of my life under his control.

    When I turned to look at Ramon he was beaming, I had never seen him looking so

    'You have made me very happy my dear. After you've cleaned yourself up we're
    going to celebrate your new life'.

    Obediently I went to the Ladies to freshen my make up. We had a few more drinks
    and talked about the future. It was late but neither of us wanted to go home so
    Ramon took me to a nightclub. By now it was 2:00AM, the place was packed with
    guests. Ramon was more excited than I'd ever seen him, talking constantly about the
    fun we would have.

    After another hour we were both beginning to tire and Ramon decided it was time to
    head for home. He called his chauffeur and arranged to meet him in about thirty

    When we left the nightclub we had to walk a short way to get to the right point to
    meet the car. Ramon decided to cut across a patch of rough ground, with me
    following him picking through the debris in my heels. He walked into an alleyway
    and suddenly stopped next to a fire escape. As he turned I saw a glint in his eyes.

    'Take your dress off slut'.

    Dutifully I reached behind me and unzipped my dress. I stepped out of it and left it
    on the fire escape ladder.


    I looked into his eyes and feel to my knees on the path.

    Ramon pulled a pair of handcuffs out of his coat and secured my arms behind me.

    Then he produced a short length of chain, attached one end to the cuffs and the other
    end to the fire escape. He stood over me, looking down at me. I saw him reach into
    his pocket and produce a blindfold, which he fastened around my eyes.

    'Now know what to do'.

    I shuffled forward to my rightful position between my Master's legs. He had already
    unzipped his pants and his cock brushed against my cheek, warm and semi erect. I
    caught it between my lips and began to suck, blissfully unaware of anything else
    going on around me. I was caught in the moment, so happy that my future had been
    decided. This was where I belonged, I could no longer imagine going back to my
    old life. I used my whole mouth to worship Ramon, proud of the fact that I could
    turn him on like this and determined to please him.

    Suddenly I felt Ramon pushed to one side. Rough hands seized me and ripped my
    blindfold off. I looked up - shocked - straight into the beam of a torch. It took a
    moment for my eyes to adjust and then, suddenly, I saw it. A police car behind
    Ramon with the two front doors open and the officers standing next to him pointing
    their guns at us.

    I was crying as they put me in the back of the car - I can only remember little things.
    I remember wondering why they had taken off my handcuffs only to cuff me again
    with their own set. I remember thinking how big and clean the police station was. I
    can remember how terrified I was that they would send me to prison and I would
    end up as the cum receptacle of lot of horrible cons. A little faggot like me stood no
    chance in prison. I was convinced the police would rape me before I even got to

    I was actually treated very well. They put me in the sick bay so I wasn't locked up. I
    was interviewed by two female officers, the most humiliating part was when they
    arranged for a locksmith to come in to cut off my chastity belt. They gave me some
    pills to let me sleep and I spent most of the next day telling them my story. I left
    almost nothing out but I was careful to stress that I had been a willing participant
    and Ramon had not forced me to do anything. I asked about him but they refused
    even to tell me if he had been arrested.

    They left me alone for most of the next day while they considered what to do with
    me. I was still convinced I was going to jail. Early that evening the lieutenant and
    one of the officers that had interviewed me came to the sick bay. They introduced
    me to a man they said was a lawyer appointed by the court and left us alone.

    I don't remember all of the conversation but the point was that I was guilty of
    violating several public indecency laws carrying a maximum term of ten years jail.
    At the same time no one really wanted to prosecute me because everything had
    happened between consenting adults and we had been arrested in the middle of the
    night in a secluded spot far away from any residential areas. The state of California
    was not interested in spending thousands of dollars each year to keep me in jail.
    They were however interested in the fact that I was an illegal alien with no right to be
    in the United States (my visa had long since run out). The Prosecutors Office would
    be in court at 9:00AM the following morning to recommend to the judge that I be
    deported. They didn't want to prosecute me but they did want to send me home. I
    was warned that there was no possibility of me ever getting another visa so I should
    not attempt to return. I had no rights in this process, if the judge ruled against me I
    would be deported immediately.

    I don't think I slept at all that night. I started crying a few minutes after the lawyer
    left and I couldn't stop. I was shaking uncontrollably, it was a horrible choice. Going
    to jail for ten years or never seeing Ramon again. I couldn't see a way out.

    They came to see me again just before lunch the next day. The lieutenant read me
    the judgement. I wasn't listening, just staring at the wall in shock. I already knew
    what was happening. When they entered the room they were carrying the same bag I
    had brought with me from the UK. They had been to Ramon's house to collect my
    belongings. I was going home.

    They drove me to the airport in a squad car with the siren on. By then I had given
    up, I was totally devastated and fully aware that I had no choice over my fate. The
    girl on the checkout looked at me strangely, no doubt she was wondering about this
    short weedy guy with a rather feminine hair style, thin arched eyebrows and pierced
    ears. Why did he have a police escort? I can remember looking at her and thinking
    how lucky she was to be young and pretty and feminine.

    I was taken straight through to the plane after checking in. The officers stayed with
    me until just before the doors were closed, luckily the plane was nearly empty so
    there was plently of room. I ran it over and over in my head - I had no options, no
    opportunity for escape. Even if I managed to slip off the plane somehow I would
    never get out of the airport without being picked up. I had come so close - I knew
    that I couldn't go back to my old life but I also knew I didn't have any other option.

    Soon enough the plane was hurtling down the runway and my time had run out. As
    we banked over the coast before heading east I looked down on the city and said
    goodbye to Ramon. My eyes filled with tears, I thought I would never see him
  2. Mistress Michelle

    Mistress Michelle Magical Mistress

    May 17, 2008
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    What a wonderful story!!! Please continue charlotte...I am sooo intrigued now, and cant wait for the next chapter.

    Mistress Michelle
  3. Rachel

    Rachel Owned by Mistress Michelle

    Feb 19, 2009
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    FANTASTIC writing sissy charlotte simply FANTASTIC.

    MM's sweetpea
  4. vickitransgirl

    vickitransgirl Junior Member

    May 31, 2008
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    I have to agree! fantastic.... please continue the story
  5. kathyann24ts

    kathyann24ts New member

    Aug 26, 2010
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    Yes, please tells us how it ends. You left me on the edge of my seat & I need to know what happens next.
  6. Leatherelf

    Leatherelf New member

    Jul 5, 2011
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    11:45 PM
    Being new to this site I have just finished reading both parts to this story and I found it very well written and exciting to read. I see it has been over a year now since you posted this and I do hope you will consider finishing this story.

    Well Done girl.

  7. MissKelly

    MissKelly Member

    Dec 9, 2011
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    Omg yes please finish I need to know what happened
  8. Strict Sir

    Strict Sir Active member

    Mar 9, 2011
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    Very good... yes, please continue and share!
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