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I Love Sissy Boys

Personal Stories, Advice, and Support 1,661 People

    Sissy Boys - i love feeling soft and feminine win i wear girls clothes and love to see sissy like me
    tammy2 tammy2 56-60, M 3 Responses Nov 11, 2011

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    New To This - I have until recently thought of myself as a sub, until I started seeing a guy that wanted to switch. Since he was so wonderful in playing out my fantasy, I wanted to...
    meanbaby meanbaby 46-50, F 4 Responses Mar 26, 2013

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    Girly-boy - I've been occasionally dressing in girls clothes since I was 11. It's great to feel those soft feminine clothes and to be treated like a girl!
    Debrasimone Debrasimone 18-21, M 20 Responses Apr 19, 2010

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    I Love Sissy Boys........... - .....es[ecially when they have my **** in their mouth.....................
    phildavis15 phildavis15 51-55, M 3 Responses Oct 13, 2012

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    Sissy Paige - Well..I must say I do and always have taken pleasure in my femininity, and taken pride in looking as pretty as I can. I guess I was always self conscious, growing...
    fairdesire fairdesire 46-50, T 26 Responses Jul 28, 2013

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    Girlfriend Dresses Me - well sweeties, i decided to tell my gf of one week that i dressed as a girlie sometimes , when i felt like it!!!.She said she had never heard of such a...
    phillipa phillipa 46-50 5 Responses Jul 26, 2011

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    A Girl At Heart - Hi, my names Paige... I've been a crossdresser all my life, for as far back as i can remember. At 7 yr.s old I was sneaking my mom's nylons to wear. I always had...
    fairdesire fairdesire 46-50, T 20 Responses Apr 25, 2013

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    Jane...i Have Her - I was so turned on by what was happening, I could barely stand it and I was more than a little with what I was about to do! I had to jump though and make it...
    AZDom AZDom 36-40, M 7 Responses Dec 21, 2011

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    I Was A Transvestite Street ***** - Hello, my name is Michael For over 12 years I worked as a transvestite street *****. Here I am leaving my pimp's car: Each night I sucked off...
    CarolinaGayProstitute CarolinaGayProstitute 41-45, M 3 Responses Jan 21, 2013

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    Dressing For Wife - In the weeks leading up to Valentine's Day, my wife expressed that she wanted a special day. She said I was to get her nothing for it, but that she had it all...
    pantiescouple pantiescouple 26-30 1 Response Jul 20, 2010

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    Bully To Sissy In Two Weeks! - I knew I was in trouble when Mrs. Mathews the assistant principal at my middle school came out of her office and said I got a hold of your mother and...
    subjaye subjaye 61-65, M 1 Response Jun 19, 2013

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    Crossdress - I m cd in Dhaka,I want to be cd lover girl or boy for fndship.
    tomakhan tomakhan 22-25, F 1 Response Nov 3, 2012

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    My Turn On - When i look at **** whit a sissy boy in the room and we are both horny watching shemales ******* each other. He go on his knees and start to moan like a girl taking my...
    avram32 avram32 31-35, M 9 Responses May 22, 2012

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    Always Been Fascinated - I've always had a big transsexual/shemale fetish, and I think my love for sissy boys is a part of that. I love boys who are into being/actling like girls...
    JessicaXoX003 JessicaXoX003 22-25, F 14 Responses Mar 26, 2013

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    First Time Seeing An ***-***** King In Action - First time seeing an ***-***** king in action The first time I actually saw an ***-***** King in action was when I walked into my...
    keithblack keithblack 36-40, M 10 Responses Apr 4, 2011

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    Sissy Boys And Sissy Baby Stories Turn Me On. - I don't cross dress or act out sissy baby fantasies, however, Their stories turn me on.I have a deep seated insecurity about my...
    ALincoln5 ALincoln5 66-70, M May 19, 2013

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    The Secret Of My Shorts Child ... Reflections Perversity. - I do not know why I always, as a child, I had the crazy idea that the shorts were associated with spanking. I started...
    rikyspanking rikyspanking 31-35, M Nov 21, 2012

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    My First Sissy - I met this sissy online and decided to meet. He invited me over for afternoon play. I was told the door would be open to come in and enter the bedroom. I enter the...
    Blaconda Blaconda 51-55 5 Responses Mar 21, 2011

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    Sissy Boys And Ballet - Let me share the 10 reasons why sissy boys should be really taking ballet class to become real girly sissy boys 1. Ballet will teach the sissy to move in a...
    danseuretoile danseuretoile 31-35, M 3 Responses Feb 12, 2013

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    New Adventures - I need to try some new things, you know, have a new sexual adventure. I've always wanted to play with a sissy boy. It's just so naughty. I want to dress him up...
    Bionical Bionical 18-21, F 8 Responses Jan 3, 2013

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    I Adore Sissy Boys - I am not a sissy boy. In no way do I resemble a sissy boy. My hair is short. I wear a (usually) trimmed mustache and goatee. My footwear is unadorned, low...
    ArgleBargle ArgleBargle 41-45, M 3 Responses May 1, 2013

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    Love Men To Let Me Know I Am A Sexy Sissy. - I would like to tell you how men treat me. I dress as a woman 24/7 now, and am proud to be a man's sexy toy. I told you all in my first...
    Mansbedtoy Mansbedtoy 41-45 1 Response Mar 21, 2013

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    I Recently Found Out My Boyfriend - i recently found out my boyfriend cheated on me , I want revenge and no he likes to dress girly I told him I wanted real man and not a sissy...
    kaka222 kaka222 22-25 7 Responses Dec 9, 2010

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    Lingerie To Lace. - When I was a teenager, I got curious, and one day, with nobody else home. I tried on my mothers slip, panties, and dress. I've been hooked ever since. I've...
    Patricia699 Patricia699 41-45, M 2 Responses Oct 21, 2012

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    Tried... But Couldn'T Stay Away. - Hi, This is Lilly. I and my photos are back online. About two weeks ago, I started to get a little scared about what I had gotten myself into. I...
    Lilly292 Lilly292 41-45 4 Responses Jan 30, 2013

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    Sissy Boy Gives Public Show - this story is real and i cant help but share it. i know its long but i wrote every sexy detail and encourage all of you to read it and give me your...
    alexmenace02 alexmenace02 18-21 2 Responses Aug 24, 2012

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    Sexy Sissy - I love for my sissy to be dressed in sexy fem clothing for me, It just drives me crazy!!!
    sissiluvr sissiluvr 31-35, F 1 Response Jul 19, 2010

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    I Love - Ilove dressing in panties and nylons. Just bought me a little pink dress can't wait to feel it on it should feel good with my pink panties. I wish I could find a sissy to...
    pattiemorgan pattiemorgan 51-55, M 1 Response Apr 28, 2013

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    Hmmmmm - Wouldn't mind talking to a girl/shemale/dickgirl/futa who is into a 17 year old aussie sissy ><
    mammamahegd mammamahegd 18-21, M Jun 27, 2013

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    I Love Being A Sissy Boy! - I was never comfortable with being a man in the world and I had no real interest in dating or pursuing women. I tried having sex with them and it was...
    golsa2 golsa2 22-25 9 Responses Dec 31, 2011

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    My Fi Kiss From A Man. - The man that i wanted was my wife's ex Boyfriend. She would tell me he was a real man, and knew how to **** her. I put on my sexy black dress and went to...
    Mansbedtoy Mansbedtoy 41-45 Mar 21, 2013

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    Sissy Justina - Sissy Justina I had been on my job few a few months when I caught my very feminine White boy coworker having lipstick applied by a female coworker. He was caught...
    keithblack keithblack 36-40, M 19 Responses Apr 4, 2011

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    Sissy Boys. Yum! - I simply love little sissy boys. Seeing them dressed in their frilly and lace clothes. they are just so cute. I haven't had the pleasure yet but I would ...
    LittleLisa LittleLisa 61-65, M 8 Responses Oct 21, 2009

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    I Lov Sissy Boys - being a sissy i lov to play with other sissy boys,since they wear sexy sissy wear keep their bodies shaved and love to 69 and share our sissy *** by french...
    mandiejune mandiejune 51-55, M 7 Responses Sep 15, 2009

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    Are You Out There?? - There has only been one time in my life when I dated a girl who found out I dressed and actually liked it, it was an amazing feeling not having to hide this...
    pinksissy78 pinksissy78 31-35, M 6 Responses Sep 12, 2011

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    Sissyboy - i am an unfortunate wimpy little man who needs to dress in panties and bras, whilst i do this i service men from my area, i will do anything a man asks me to, ANYTHING...
    girlyboy81chloe girlyboy81chloe 26-30, M 4 Responses May 27, 2010

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    I Ready Now X - one single cute sissy subby seeking her very kinky bi or lez Femdom in Southwest of uk i adore d,s rship and been her lil dolly or baby girl or home maid in to...
    sissymelissa69 sissymelissa69 36-40, T Jul 24, 2013

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    Sissy Boys - I am a sissy boy and I like other sissy boys. Feel free to add me and send me a message. :)
    JayBird1991 JayBird1991 22-25, M 1 Response Jul 6, 2013

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    Tenting Panties - I can't think of anything more erotic than seeing a sissy being shown off by her daddy, against her will, with her erection pushing out the front of her dress...
    smiteenyb smiteenyb 56-60, M 6 Responses May 23, 2012

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    Lil Ab Me - Ello all one very cute ab sissy here single 40 and very subby too i love a Mommy or Daddy or Dom tv or sissy to baby me very much so i love all pretty pink baby wear...
    sissymelissa69 sissymelissa69 36-40, T Feb 18, 2013

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    This Is How I Was Born - the crazy part is is ive banged many girls in my life. expected where i grew up i guess, and it was ok. but since ive been self aware all i wanted was to...
    devunwalsh devunwalsh 26-30 Apr 28, 2013

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    Mistress To A Sissy - Never thought it would happen to me, being mistress. The thought never entered my head until I meet the sissy I named after me, Angel. Back in 2010 it was a...
    roseangellee roseangellee 18-21, F 2 Responses Feb 20, 2012

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    My Fantasy - i wish i had a very feminine gay friend and went over to his house to visit i go in the door is open and bump into him in the lounge and he is completely dressed up...
    Quinn1234 Quinn1234 22-25, M 3 Responses Aug 7, 2011

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    New To Sissy'S - The whole sissy boy idea is someting I've only stumbled upon recently but as a girl with a dominant streak the idea is very appealing especially the more girly...
    scarlet82 scarlet82 31-35, F 13 Responses Mar 23, 2013

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    Master Seeks Sissy - I am a 28 year old, baby-faced, 5' 8", 70 kg City professional living and working in London. I am looking for a reasonably local sissy aged 18-23, smaller than...
    masterguy78 masterguy78 26-30, M 1 Response Dec 15, 2012

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    Torment Within - I Started Early 6 or 7 I guess, my sister would dress me up, put makeup on me I would hide privately in a toy chest secretly enjoying the feeling of girly clothing...
    420negaunee 420negaunee 26-30 1 Response Aug 17, 2012

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    Ashlee'S Story - Hello, ladies, my name's Ashlee, or Ash for short, I'm a 53 year old gay sissy, who enjoy's cross dressing, and been femmine, I love dressing up, and love lingere...
    Jan 29, 2013

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    Why Im A Sissy - i was about twelve when the verry atractive misses cathrine moved next door she was tall blond and had what i thought was a nice butt one day i went over to talk...
    sissylover13 sissylover13 18-21 2 Responses Oct 12, 2011

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    To Ron - Last night it was a clear night and i can see the moon its so bright its also warm so we dont have a quilt on .... I can see by the moonlight you laying on your belly your...
    Auchentoshen Auchentoshen 41-45, F 1 Response Sep 3, 2012

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    Going Shopping With My Girl ;) - I just thought I would share a fun story that happened recently :) A couple of months ago, for the first time I went out (somewhere besides a dark...
    TaylorJ23 TaylorJ23 22-25, F 12 Responses Mar 4, 2013

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    Androgynous Body.. - I used to hate it when I was younger. I was androgynous. I looked more like a girl than a boy and people would often get confused. But when I hit the age of 16...
    AbusableUke AbusableUke 18-21, M 11 Responses Feb 9, 2012

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