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I Want To Be A Shemale Prostitute

Personal Stories, Advice, and Support 238 People

    Need Some Incentive...

    I am extremely bicurious, although not especially bisexual and as such I find it difficult to find men attractive sexually. Because of this I am still an anal virgin, although I am desperate to find out what a **** feels like in my arse and mouth. I think that if anyone was to...
    melissa42 melissa42
    31-35, T
    8 Responses Aug 6, 2010

    Made To Please

    I really don't know what made me think I could act like a man, strolling down the street. I tried to hide the fact that I was a male to female transexual, but I guess didn't fool the prostitutes I passed in the street. As I passed, I heard them giggle and chatter away, about me...
    StephanieShaw69 StephanieShaw69
    61-65, T
    1 Response Jun 2, 2013

    I Luv To Be A Shemale Prostitute

    I wish to be one. I enjoy doggy style and being thrusted from behind though it could be painful at times. I especially love to sit on top moving my butt up and down. The sensation is just so horny and erotic. Well, I definitely luv to give oral to my client......
    magmagdalene magmagdalene
    36-40, T
    3 Responses Dec 7, 2012

    I Want To Be A Transexual Call Girl.!.

    I'm A Bi-Male In My 30's,w/ A Slim Body & A Sweet Sexy ***,Butt I'm Not Passable.!.My Face Is Fine,w/Make-up On Butt I Have Just ToO Much Hair On My Body n Face&Even Tho I Can Shave It All Off,I Still Have A 5 O'Clock Shadow.!.Butt When I Dress-UpAs A Woman,I Look Hot,(Atleast I...
    Sweetsexysubslut Sweetsexysubslut
    31-35
    1 Response Apr 9, 2012

    Become Shemale Help Needed

    hello, i'm a 25 years old boy, butt i feel more women. I look much younger than i am, and i can become a very pretty female looking shemale. In my childtime i often putting my sister clothes on when nobody was at home, and i feel very good in it. I have thought about to change to...
    tgirlshirley86 tgirlshirley86
    22-25
    2 Responses May 25, 2012

    I Was Turned Into A Shemale

    I have always wanted to sleep with a hot tranny. I fault the feelings that was calling me for a long time, but one day I was going through the personals on cragslist and there was a beautiful shemale next to my home town. I hesitated but the feelings grew stronger . SO I called...
    creel12 creel12
    36-40, M
    Jun 5, 2013

    How To Start The Journey?

    It's 2:22 in the morning and suddenly I have the urge to find someone, anyone who wants a *******. Thoughts flash through my head "Put on a dress, go out to the street, or the gas station or a public restroom and offer it to the first soul I see." "I need to swallow a load...
    Kosh27 Kosh27
    26-30, M
    Sep 14, 2013

    Be Careful

    I'd think twice about becoming a prostitute, forget any romantic notions you have of what the life is like. It's hard, dirty, you meet the lowest forms of pond scum, and you will not make a fortune. I came to London from the North East 8 years ago now, troubled family life...
    HannaWork HannaWork
    22-25
    Mar 20, 2012

    I Want To Be A Shemale Prostitute

    No real story yet to be honest I'm just a guy that loves being bottom and loves dressing up like a woman. I'm just so tired of crossdressing and then being forced to go back to bring a guy. I just want to be a shemale all the time. I hate having to hide what makes me happy. My...
    CJIKatie CJIKatie
    18-21, T
    Jun 21, 2012

    I Am In This Business

    If you are dreaming of becoming a shemale hooker you have to be absolutely sure that you really want it before you enter this business. If you decide to start working fulltime you shall be aware that this is not a job that you can just quit again. I started working fulltime about...
    LLadyboy LLadyboy
    18-21, T
    4 Responses Oct 21, 2010

    I Want To Be A Shemale Prostitute

    I am 58 and I have dreamed of being a prostitute my whole life.Being a woman in a man's body is the only thing that has stopped me but as I got older and I started to have many more male friends than girl, I soon realized the effect I had on them.Especially when I sucked them and...
    louisestjohn1 louisestjohn1
    61-65, M
    4 Responses Feb 9, 2011

    I Want To Be A She Male Prostitute

    What a sexy thought , anyone interested . Need training
    Stephiebabe Stephiebabe
    56-60, T
    May 31, 2013

    I Want To Be Owned

    I don't know where to start. I have since I was about 11 years old wanted an older man to own my body make it female and make me a ****. I have been a **** on my own sleep with over 100 different men. But I have yet to find that man that wants to make me whole. Totally Fem and...
    nikkir1000 nikkir1000
    36-40, F
    1 Response Nov 27, 2012

    I Have Thought About It.

    For some time I did think about being a prostitute partially because of money.But also, I always thought there could be a lot of fun in being an upscale prostitute, a high class escort.Then again I'm pretty picky about who I have sex with and lets face it in that business, you...
    Josie06 Josie06
    56-60, F
    4 Responses Feb 7, 2012

    I Would Love To Work As One...

    I love crossdressing... The moment I crossdress, I have the urge to just be a shemale prostitute working in a massage parlour or brothel, not mainly for the cause of cash, though it matters a little bit, but more for the thrill and sexual satisfaction of being drilled by male and...
    magmagdalene magmagdalene
    36-40, T
    1 Response Jul 6, 2012
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