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I Love Sissy Boys

Personal Stories, Advice, and Support 1,704 People

    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

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

    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
    51-55, F
    2 Responses Mar 26, 2013

    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
    56-60, M
    1 Response Apr 28, 2013

    I will add sissy boys,

    if you ask politely as a sissy should.
    deleted deleted
    5 Responses Jan 18, 2015

    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


    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
    19 Responses Apr 19, 2010

    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
    19 Responses Apr 25, 2013

    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
    2 Responses Oct 12, 2011

    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

    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

    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
    1 Response Mar 21, 2013

    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
    2 Responses Aug 24, 2012

    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
    6 Responses Jan 3, 2013


    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

    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
    1 Response Aug 17, 2012

    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

    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

    sissyboys in Dubai ..

    do u need to be spanked ?
    master4slv master4slv
    36-40, M
    Jan 20, 2015

    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

    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...
    deleted deleted
    3 Responses Feb 12, 2013

    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
    Mar 21, 2013


    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

    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...
    Cutiefboi Cutiefboi
    18-21, M
    10 Responses Feb 9, 2012

    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
    5 Responses Mar 21, 2011

    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
    8 Responses May 22, 2012
    toby200869 toby200869
    31-35, T
    1 Response Mar 9, 2016

    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
    12 Responses Mar 23, 2013

    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
    5 Responses Dec 21, 2011

    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

    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...
    johnny253 johnny253
    70+, M
    1 Response May 19, 2013

    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

    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
    6 Responses Sep 15, 2009

    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
    8 Responses Sep 12, 2011

    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

    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...
    deleted deleted
    1 Response Sep 3, 2012

    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 Words...
    golsa2 golsa2
    8 Responses Dec 31, 2011

    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
    15 Responses Apr 4, 2011

    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
    20 Responses Jul 28, 2013

    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
    1 Response Jul 20, 2010

    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
    26-30, F
    13 Responses Mar 26, 2013

    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
    6 Responses Apr 4, 2011

    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
    Apr 28, 2013


    Wouldn't mind talking to a girl/shemale/dickgirl/futa who is into a 17 year old aussie sissy ><
    mammamahegd mammamahegd
    22-25, M
    Jun 27, 2013

    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
    6 Responses Jul 26, 2011

    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
    2 Responses Dec 15, 2012

    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
    26-30, M
    1 Response Jul 6, 2013

    I love dressing and being girly.

    I want to find a man near me that likes me that way. I'm in Georgia south of Atlanta. Feel free to hmu guys.
    sexyalyssagurl sexyalyssagurl
    41-45, T
    4 Responses Mar 11, 2016
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