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I Love Sissy Boys

Personal Stories, Advice, and Support 1,667 People

    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 apartment not know what to expect. As enter the bedroom to my surprise this ****** sissy was only in sheer panties...
    Blaconda Blaconda 51-55 6 Responses Mar 21, 2011

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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 urge with someone you love. There have been some instances where i have dressed for few other girls, but nothing serious or...
    pinksissy78 pinksissy78 31-35, M 6 Responses Sep 12, 2011

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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 me in every way, who wants to be completely feminised by me. Inexperience is a must - I want a shy submissive type who...
    masterguy78 masterguy78 26-30, M 1 Response Dec 15, 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 and love and adore terry nappys and yummy pink baby pins and pink baby reins ooh how i love to be in a baby life...
    sissymelissa69 sissymelissa69 36-40, T Feb 18, 2013

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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 graceful and feminine manner 2. The sissy will learn to curtsy properly which can useful once introduced to other females...
    danseuretoile danseuretoile 31-35, M 3 Responses Feb 12, 2013

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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 only dressed up for men a few times, I lost most of my ladies wardrobe. I love wearing lingerie sets and full length...
    Patricia699 Patricia699 41-45, M 2 Responses Oct 21, 2012

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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. I have been cummed in so many times my tummy is all squishy and soft. Oh yeah, men like me to take estrogen...
    girlyboy81chloe girlyboy81chloe 26-30, M 4 Responses May 27, 2010

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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. I also love when they have little clittys and realize that their place is being a girl.
    JessicaXoX003 JessicaXoX003 22-25, F 14 Responses Mar 26, 2013

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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 **** deep in his sissy mouth
    avram32 avram32 31-35, M 9 Responses May 22, 2012

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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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    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 normal day when I meet Angel. He was in the middle of sex change operation and something about him caught my attention. A...
    roseangellee roseangellee 18-21, F 2 Responses Feb 20, 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 up effeminate and all..I was pretty much an outcast, the girls didn't want me..because I wasn't masculine enough...
    fairdesire fairdesire 46-50, T 26 Responses Jul 28, 2013

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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 When puberty hit I didn't know what was happening to me, I cried when my voice changed I used to love singing the...
    420negaunee 420negaunee 26-30 1 Response Aug 17, 2012

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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 pantyboy , if anyone wants to laugh at him it mn.ryan@yahoo.ie
    kaka222 kaka222 22-25 7 Responses Dec 9, 2010

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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 thing!!.but wanted to see what i looked like......7 years later .......we still enjoy it ....not ALL the time...but when we want...
    phillipa phillipa 46-50 5 Responses Jul 26, 2011

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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 playing with my small penis at the age of four or five years old ... Then, my mother threatened to stop doing it, what I started doing in secret ... The word...
    rikyspanking rikyspanking 31-35, M Nov 21, 2012

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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 many men, mostly in cars and trucks curbside or in special parking lots where ****** loitered and also in parks and other places. There...
    CarolinaGayProstitute CarolinaGayProstitute 41-45, M 3 Responses Jan 21, 2013

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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 chastity and other stuff pvt me or see my page i hope to feel er pink collar very soon huggs sissy melissa pink x
    sissymelissa69 sissymelissa69 36-40, T Jul 24, 2013

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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 decided to pull my photos and back away. I was off the site for at least two weeks. Now I find myself coming back. A part of me still...
    Lilly292 Lilly292 41-45 4 Responses Jan 30, 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 as i always did and i walked in (we never locked our doors in our town) and she wasnt there i decided to go and dig...
    sissylover13 sissylover13 18-21 2 Responses Oct 12, 2011

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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 play dress up with. Here in Alaska.
    pattiemorgan pattiemorgan 51-55, M 1 Response Apr 28, 2013

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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 just love to have a little sissy to have sex with. Being all dressed in her sissy clothes and kneeling down to suck me...
    LittleLisa LittleLisa 61-65, M 8 Responses Oct 21, 2009

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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, play with him, spank him, use toys on him, and everything else you could think of. I just think that would be so hot...
    Bionical Bionical 18-21, F 9 Responses Jan 3, 2013

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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 that deep desire to be a girl! Pretty much behind closed doors, although i've had a few occassions where i was out of...
    fairdesire fairdesire 46-50, T 22 Responses Apr 25, 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 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 just..... meh. Then I ordered several pairs of panties, bras (I naturally have an A cup :D), and dresses from Amazon.com. Words...
    golsa2 golsa2 22-25 9 Responses Dec 31, 2011

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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 **** boys. I had a hump session with my best guy friend was i was young, but never anything real. but now as an adult every...
    devunwalsh devunwalsh 26-30 Apr 28, 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 story about my first kiss. Well i knew i belonged in a man's bed, and began to work on my body to turn men on. I toned up full wax, and was...
    Mansbedtoy Mansbedtoy 41-45 1 Response Mar 21, 2013

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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 gay bar) with my gf dressed as herself. I think I was more nervous than she was as we were getting ready to leave. She's a beautiful...
    TaylorJ23 TaylorJ23 22-25, F 13 Responses Mar 4, 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 feedback. hope you all like ;) this story begins about a year ago, i was 17 at the time and a bit confused. secretly i am a slutty...
    alexmenace02 alexmenace02 18-21 2 Responses Aug 24, 2012

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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 kissing after 69!!!!
    mandiejune mandiejune 51-55, M 7 Responses Sep 15, 2009

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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. he has no idea i have gay tendacies and tries to cover up. i tell him not to and wlk up to him and start kissing...
    Quinn1234 Quinn1234 22-25, M 3 Responses Aug 7, 2011

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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.  Then for her to be made to lift the front of her dress exposing her tented panties with a wet patch in them. I think...
    smiteenyb smiteenyb 56-60, M 6 Responses May 23, 2012

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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 nightie has risen and i can see your *** so i start to sroke your *** and thighs and move myself along side...
    Auchentoshen Auchentoshen 41-45, F 1 Response Sep 3, 2012

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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 be as open to his. He looks smokin hot in ruffled panties, and I'm discovering how turned on I can be by his...
    meanbaby meanbaby 46-50, F 4 Responses Mar 26, 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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    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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    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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    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 she will be down to pick you up soon. I was very mad about that and I was sure that she would give me one of her good talking to's...
    subjaye subjaye 61-65, M 1 Response Jun 19, 2013

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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 guys in pink, frilly outfits. So if anyone wants to chat send me a message.
    scarlet82 scarlet82 31-35, F 13 Responses Mar 23, 2013

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    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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    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 planned out. The day before, I came home from work to a wrapped box with a red bow and a note that said she was at the...
    pantiescouple pantiescouple 26-30 1 Response Jul 20, 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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    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-heeled boots. I wear blue jeans and pearl snap shirts. Yes, I do wear a stetson-style hat--when the weather or work call for...
    ArgleBargle ArgleBargle 41-45, M 3 Responses May 1, 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 neighbor’s bedroom. I had been invited over to Birdman’s townhouse many times before. Often we would chill while having a beer and he would do...
    keithblack keithblack 36-40, M 10 Responses Apr 4, 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 his door. He thought i was a wom ,i said i hear your a real man, and want to suck you ****. He said come in i Went thinking...
    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 off guard and I knew it, so I said," what the hell is going on here"? He stammered a bit and mumbled something about...
    keithblack keithblack 36-40, M 19 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 masculinity from childhood experiences which , I think, is the cause of these fantasies. I was also a bed wetter until I was 12 which also may have...
    ALincoln5 ALincoln5 66-70, M May 19, 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 I thought it was something erotic. I had already figured I was pretty much gay and by my looks I classified myself as a...
    AbusableUke AbusableUke 18-21, M 11 Responses Feb 9, 2012

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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 happen, so I just did it. “You’re a pretty girl James” I said as I shoved my phone back in my pocket. She snapped...
    AZDom AZDom 36-40, M 7 Responses Dec 21, 2011

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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, I've been dressing since I was 22, and enjoy it very much, I've had my lip's done, and alway's have my hair styled...
    Jan 29, 2013

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    Related Experiences

    Thank you for thinking about me today! I am an effeminate little pretty boi who loves to bottom and be the wife in a relationship!
    FemGayBottom FemGayBottom 26-30, T 2 Responses Apr 9

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    Having cute boys underwear is a real turn on for me.
    boicuddles boicuddles 26-30, M 1 Response Apr 5

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    ah every single guy I've ever been with has been real country. like down home, home grown, small town country. I guess that's just what I'm attracted to
    countryanon countryanon 16-17, F Mar 26

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    I just love bad boys. I love their ways. I find them very exciting to be with. I once asked my boyfriend to hit a guy as he was staring at me. My boyfriend bashed him up and threw...
    prettytoes prettytoes 22-25, F 7 hrs ago

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    Here's a little secret of mine... I love bad boys <3 and not only that but I'm addicted ... <3 any bad boys out there? (:
    beckebreez beckebreez 18-21, F 3 Responses Mar 25

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