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I could see cum dripping out of her dilated...

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  • I could see cum dripping out of her dilated...

    Let me introduce myself. My name is Jenny. I used to be called James but
    that was over a year ago. I moved to Singapore to further my studies. I am
    small for a guy, only 5 foot 8 and not very well built. Still I feel almost
    average height in Singapore where everyone is the same height as me.

    My story begins when I read an article about a street in Singapore where
    lots of transsexuals hang out. I had never really thought about these
    things before and as I had nothing better to do I went down that night to
    have a look. There were so many beautiful transsexuals. Most of them really
    beautiful. They were from either Malaysia or Indonesia and if I did not
    know better I would have said they were real women. I was approached by
    many and eventually persuaded to follow one into her room. I gave her 50
    dollars and she began to strip. She had lovely breasts and I was extremely
    turned on. She removed the rest of her clothing and I fucked her artificial
    pussy. In fact it felt very much like the real thing, only with the use of
    some KY jelly.

    Over the next few days I could not get the image out of my mind. I felt so
    dirty fucking not only a prostitute (this was my first time) but also
    someone who had started life as a man. I have only ever had girlfriends and
    I cannot name one man whom I am attracted to. Anyway, it was only a matter
    of time before I found myself down Desker road for a second time. I could
    not find the girl I had fucked before, even after waiting around for over
    one hour. Anyway I had seen another one that took my fancy, called Candy
    and I followed her. She had long black hair and a naughty sparkle in her
    eye. I knew she had fantastic breasts, because she was wearing a see-
    through black top with no bra. Sitting down I paid her and as she was
    standing she moved between my legs. She leant down and I kissed her. She
    kissed so gently that I could have come right there and then. I moved my
    hands over her c-cup firm silicon breast before licking her nipples through
    her blouse. She moaned as I did this and leaning forward started to rub my
    cock through me jeans. I moved my hands up under her miniskirt and on to
    her silk panties. The she took my hand and moved it around and started to
    rub her crotch. It was so smooth and I could feel her pubic hair under the
    thin material of her panties. I rubbed harder trying to find her slit,
    wanting to feel what I was about to fuck, but there was no slit. All I
    could feel was a lump and I suddenly realized that she actually had a cock
    which was tucked between her legs and was now straining to get out as it
    was hard. I pulled my hand away, not sure what to think. I knew I was not
    gay but then again I did not feel gay as I was kissing a beautiful woman.

    "You can fuck me here" she said moving my hand round to her firm arse.

    She then moved my hand back to her cock which had appeared from its hiding
    place between her legs. It was not big, maybe only 5 inches long, and not
    fat either. It gently strained against the thin material of her panties and
    almost instinctively I started to run my hands over it. I could feel myself
    really hard as she unbuttoned my flies and herself moved her hand over my
    cock. Almost as if she was telling me what to do she moved her hand inside
    my shorts and took hold of my cock, which was considerably larger than
    hers. I did the same and for the first time in my life felt the smooth skin
    of an Asian's shemale clit. It felt so warm as she undid her skirt which
    fell to the floor. Almost as if she was paying me she moved her panties to
    the side and her cock stood out in front of my face, as I was still
    sitting. Without even thinking I took her into my mouth. I wanted to know
    what it felt like.

    It tasted wonderful as I slowly started to move my mouth up and down her
    shaft, sucking harder as I savoured her scent. She spoke like a little
    angle that she was and moaned as I continued to give her cock attention.

    "Do you want to fuck me now?" she said, but I was more interested in
    sucking this beautiful cock which was in my mouth. I cupped her sweet small
    balls and then tried my best to give her the most pleasure. I soon leant
    that running my tongue up and down her shaft as I looked up into her eyes
    really turned her on and I also found out that she got really excited as I
    fingered her arse hole. Her I was a respectable business man sucking the
    cock of a common street whore who dressed as a man...and I was loving every
    minute of it.

    She moved over to the bed and I took off the rest of my clothes as she did
    the same. I don't know if it is an Asian thing but she looked just like a
    women with a cock. I lay next to her and she started to lick my cock before
    moving lower and licking my arse hole. I have never found a women willing
    to do that and it felt fantastic. I motioned her to move around and she did
    offering herself in the same way. I licked down the length of her cock this
    time as we were in a 69 with me on the bottom and started to take her small
    balls into my mouth. like the rest of her they were hairless. Then I wanted
    to please her as she had me and moved my tongue to her anus, licking
    gently, she spread her legs wider and as she did this her anus opened up
    slightly and I started to dip my tongue into her. She moaned in delight as
    I did, taking my cock out of her mouth long enough to tell me that I was
    her first customer of the evening. Somehow I felt privileged at hearing
    this and doubled my efforts to please her. Without warning she started to
    cum in my mouth. I was gagging as she forced her cock deeper into my
    throat. There was nothing I could do except savour the pleasures of her
    warm cum shooting into my mouth and down my throat. She pulled her cock
    from my mouth allowing a spurt of warm cum to land all over my face. I
    swallowed what I had in my mouth before licking her little cock dry. I felt
    I was serving her instead of the other way around. All this was too much as
    I began to cum in her mouth. She then moved around and kissed me again and
    we shared my cum licking it from each others mouths.

    The next day or two I was in a real state. Almost disgusted with myself at
    what I had done, I was confused by how much I enjoyed it and the pleasure
    it gave me to suck cock. Of course I went back and sucked Candie's little
    she-cock many times over the next month and she mine. I also fucked her
    many times and enjoyed the pleasure and pain on her face as I did this (I
    have a large thick cock).

    And then she was gone. I returned to Desker road one night and there was no
    sign of her. I was lost for words. So I started to look around for another
    one. There was one I had noticed many times and I chose her. It was at that
    moment that my life changed. Her name was Rebecca, she was from Singapore
    and she was beautiful. Long dark hair, heavy firm breasts, such a cute arse
    which wiggled when she walked, and those large rosy lips. She also acted
    very feminine and I would never have known that she was born male unless I
    could feel that 6 inches of cock pounding the back of my throat almost
    every night.

    So that was that, I had found perfection. I was never so satisfied sexually
    and she new it. It was at this point that she started to take more of an
    interest in me, asking questions like

    "why do you like sucking my cock so much?" and "do you like the taste of my
    cum?" She always asked me these questions when I was busy working on the
    beautiful slender soft cock of hers, and therefore could only look into her
    eyes and show that the pleasure I was having meant yes to both.

    She wanted to fuck me and I was so excited by the idea that I could not say
    no. She took my virginity away slowly and painfully with me staring up into
    her eyes, cupping her firm breasts and she started to fuck me until I felt
    her cum in my arse. It felt wonderful and the pleasure was even more
    intense feeling some of her cum drip out of my arse hole as she removed her
    cock.

    "You like that didn't you?" she asked. "You like getting your white arse
    fucked by a lovely cock don't you?". There was only one answer and she knew
    it.

    I saw her everyday for three months, paying her S$50 every time. Soon I was
    running out of cash and I dreaded the day that I was not going to be able
    to pay. That day came soon enough and I told her that I had left my wallet
    and that I could pay the next day. She agreed, but was not so convinced the
    next day when I could not pay either. When she confronted me about it I
    told her that I had given all me money to her and had no more. I also told
    her that I did not think that I could live without her. Could she be my
    girlfriend?

    "And let you fuck me for nothing?" she laughed "Then where am I going to
    get my money from?"

    I sat there in silence wondering how I was going to be able to keep seeing
    this angel with a cock.

    "OK, I have an idea" she said, "I won't be your girlfriend but you will be
    my boyfriend, OK?" I was confused at this, not sure what she meant. "In
    other words, you will serve me whenever I want you too. Fuck me whenever I
    like and let me fuck you whenever I like, agreed?" This sounded
    perfect. "One other thing", she continued almost as an afterthought, "do
    exactly as I say."

    "Agreed" I laughed moving forward to hug her. she kissed me and I moved my
    hands down on to her arse.

    "Oh no you don't" she said "I don't feel like it right now" Simply by
    saying that she had made the extent of our agreement obvious. She was now
    in charge. I was no longer the customer. If anything the roles were changed
    and I was to serve her needs from now on.

    It went on like this for a week or so. I met up with her at agreed times
    (her agreed times) and we fucked at her convenience. She made me clean her
    room sometimes, removing the used condoms and cum stained tissues from her
    bin which customers had left behind. She told me she always uses a condom
    unless she is sure the man is clean, which was very rarely.

    Then one day she gave me a pair of her soiled white cotton panties and I
    assumed I was to wash them.

    "Where are you going?" she asked as I went towards the sink. "They are for
    you".

    "A present?" I asked.

    "You could say that." she said. "I want you to wear them and that way we
    will be connected all day. You shall wear them tomorrow, all tomorrow and
    be wearing them when you come to see me"

    She knew this was a turning point in our relationship but I had not
    realized. in fact I was very excited about wearing her panties. I took them
    home and sniffed them, clearly making out her scent that she had left
    behind. I wanked as I did this and was surprised how quickly I orgasmed.

    The next day I wore her soiled panties to work all day. They were tight
    which just reminded me I was wearing them. On two separate occasions I had
    to relieve myself in the men's room. When I turned up to see Rebecca she
    was angry though.

    "What do you think this is?" she said looking at me wearing her panties. I
    was confused "but i thought..."

    "When you wear a pair of ladies panties you must tuck your nasty cock
    between your legs where is belongs." I was still confused but at why I was
    aroused by the concept of seeing myself "tucked" and behaving like Rebecca
    did.

    "Go ahead" she said. I tucked my cock between my legs and looked down at my
    new smooth feminine crotch. "That's right sweetie. Now, how does it make
    you feel"

    "Feminine" I said, "and a little bit silly".

    "That is because you are not behaving like a girl. Of course if you wear a
    pair of panties you must play the part. Now, what do girls do?"

    "Look sexy?" I replied after some thought.

    "No silly...they suck cocks. Girls LOVE to suck cocks." She hitched her
    skirt up and pulled her knickers to the side. Her erect cock sprang to
    attention in front of me.

    "Now, I want you to suck it." I knelt down obediently and took it into my
    mouth tasting the familiar scent of her. "Not like that!" she said pulling
    her cock away. She lifted my head up with her hands and looking me in the
    eyes from above said "Imagine you are a girl and this is a real man's
    cock. Imagine it is your job to please him. Imagine he has paid you to suck
    him dry, as a girl not a man. Now go ahead. Imagine I am a man and you are
    a sissy transsexual like me trying to please him."

    I leant forward again and this time tried to suck the cock gently and
    delicately as girls often had in my previous life. I gently cupped her
    balls and took the cock slowly down my throat, all the time moaning like a
    little slut would.

    "That's good darling. Now look at me in the eyes and tell me what you are
    and what you are doing."

    I instinctively knew what to say. I pulled the cock out of my mouth,
    leaving the tip next to my lips so I never quite lost contact. Looking up
    into her eyes I said

    "I am a little slut sucking a real man's cock"

    "AND" she said...

    "and I want to make my customer happy by making him come"

    Obviously I had said the right thing because at that moment I felt a warm
    jet of my lovers cum shoot over my face.

    "Now little sluts like you also need to clean a real man up. It is part of
    the service" I licked his cock dry. It tasted different this time. As
    though I really was a little slut who had earned her cum.

    "Now get dressed" Rebecca said. I did wiping my face clean with my fingers
    and licking them dry as instructed.

    "Here" she said, passing me $10. " I laughed

    "I am not a hooker, and besides, I give you $50"

    "And when you learn to suck real men properly, maybe they will give you
    $50"

    At home that evening was about the time I realized that the roles had
    completely turned. I was still desperate to be in her company and never
    felt so content sexually, but there was no denying the fact that she was
    starting to treat me a transsexual myself, which I was not, and had no
    intention of becoming. I was unaware at that time of the gradual process of
    forced feminization that had begun. Maybe I should have been a little
    suspicious when I thought to myself, stroking my cock in bed through the
    silky material of a pink thong she had given me, but it was kinda fun.

    Over the course of the next few weeks Rebecca started to teach me the ins
    and outs of prostitution without even knowing it. I only ever "serviced"
    her but she made me do it in the most degrading fashion with me having no
    control over when, where or how. I leant to suck her cock like she would
    suck mine, she taught me to arch my back and moan softly for more as she
    fucked my tight arse. She taught me to clean her cock with me mouth and
    lick her arse with my dirty tongue.

    In the meantime I had lost my job. I put this down to the economic
    recession but the reality was that I was no longer thinking about work,
    preoccupied with serving my mistress. I simply could not leave Singapore
    and Rebecca and almost naturally I moved in with her and was living as an
    illegal alien. I shared her flat and she made me sit tied up in a chair
    watching men come in and fuck her for $50 a shot. I was angry that they
    were touching my girl and upset that she seemed to enjoy it so much.

    "You just better get used to it" she said "cos I need the money and like
    the action."

    I had a little money which Rebecca had given me, usually as a present after
    a degrading act like licking her arsehole when she woke up in the
    mornings. she loved that. But it was not much and soon she told me that I
    had to start earning my keep. I was terrified that she was going to suggest
    that I service men too, but she laughed at the suggestion saying

    "who would pay good money to fuck you? I have long silky hair, great tits
    and a willing hole. You have just got a hole and it seems it is not even
    willing. No, you shall service me. Each time I have a customer you will
    lick me clean."

    I was not sure exactly what she meant, but that night after a man had
    pumped his load into Rebecca's arse she untied me and got on her hands and
    knees. I could see cum dripping out of her still dilated arsehole and
    instinctively knew what I had to do. I licked the cum dripping down her
    soft thighs before using my tongue to dip into her arse and lick her
    clean. I felt so degraded and she would not even let me wipe my face clean,
    which was covered in cum, before another customer came in. I had to sit
    there like a little cum-covered bitch, watching my next job being created.

    Another week passed and Rebecca's plans became more intense. I had to
    remove all body hair, have a perm and have my ears and nipples pierced. I
    was also put on hormones (I don't know what) and I could feel my skin
    becoming softer.

    Over the next 12 weeks, I was basically Rebecca's maid-in-waiting. Cleaning
    after her, licking her arse clean and doing anything else she requested. In
    return, she would let me fuck her occasionally and sometimes even suck me
    off.

    All this time I had been restricted to t-shirts and jeans. I knew that soon
    I would be wearing female clothes, which I originally dreaded, but by
    denying me for so long, I was keen in the end, just so that she would let
    me. She took me shopping, and bought me my first bra and panties set. It
    was cotton and white. She told me it was a trainer bra for my little AA-cup
    titties and that soon I would need a bigger one.

    "These are for him" she told the girl serving us. I was so embarrassed. The
    sales girl looked at me oddly, and with disgust and I could have shriveled
    up and died. She also bought me a pink dress which hugged my body
    beautifully, especially as I was so slim after not being allowed to eat
    much for so many months. Next stop was the makeup counter. Rebecca was so
    generous and she made me say

    "thank you for buying me my first lipstick" or "I am so pleased to have my
    very first blusher". It was all part of her game to make me more obedient.

    That night I was allowed to wear my new outfit and she made me up. I was
    still tied to the chair but this time I looked more female than male. In
    fact I was beautiful and there were even customers who were looking at me
    with desire as they fucked Rebecca.

    Then the day finally came. Two Chinese males had come in and one was
    fucking Rebecca while she sucked the other. She said that she had to go to
    the bathroom and pulled away from them.

    "Here, Jenny will take care of you while I am gone" she said as she untied
    me. Then she left without another word and I was sitting there alone in my
    bra and panties with these two erect Chinese cocks in the room with me. I
    was taken completely by surprise when one of them came over and stood with
    his cock in front of me. I just looked at him. But he slapped me and told
    me he had paid good money and wanted his cock sucked. I leant forward and
    took him into my mouth. He was the one who had been fucking Rebecca and I
    could taste her familiar taste of her arse as I sucked him. The other
    Chinese guy came up behind me and now standing, pulled up my skirt. Before
    I could remove the cock firmly embedded in my mouth he had pulled my
    knickers to the side and had pushed his cock into my tight arse. I could
    tell he had lubricated it well and he began to fuck me hard. I well to my
    knees still sucking that beautiful cock in front of me except this time I
    was pushing my arse back to meet the strokes of the cock entering me.

    "I see you are getting along just fine" said Rebecca as she walked into the
    room. She knelt next to me and felt for my cock in my panties, slowly
    wanking me off almost as a reward. The two men came together, and I was a
    mess with cum everywhere when they left. Rebecca licked my arse clean this
    time, kissing me on the lips afterwards so I could taste my "work" and then
    gave me my cut. A full $50. I was so proud.

    Now a year has passed. I have had c-cup implants done in Thailand and I am
    slowly paying off the borrowed money for the operation to Rebecca. I
    service maybe 10 guys a night. Sometimes Rebecca and I work together,
    sometimes alone. One thing is for sure. Ever night our arses end up
    saturated with cum and we always clean each other. I have a full wardrobe
    of beautiful clothes, g-strings, frilly pink bras etc. which I love. I
    would never change my life back to what it is. I am a little whole slut
    with a cock that services dirty men I don't even know for a living and I
    would not change it for the world. Thank you Rebecca.

    End


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