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I Am a Sissy

Personal Stories, Advice, and Support 4,130 People

    My First Outing

    Recently I found a girl who I was willing to trust with everything. And she was totally fine with it, she even liked it a little. She encouraged me to do it more. So I did. She worked at a subway on the ground floor of an apartment building near my school. Nobody ever went their...
    agirlatheart8 agirlatheart8 18-21, T 12 Responses Jun 5, 2013

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    I'm a Sissy ~ Luckily

    My story … well … as my name suggest, I’m a sissy. I’m not complaining … just the opposite … it’s like a stroke of luck. I love it. Life would be so dull and boring if I weren’t. I’m really happy to be so special and...
    CherrySissy CherrySissy 46-50, T 23 Responses Aug 15, 2008

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    I'm a guy and I like being girly.

    . I just wish someone would help me embrace it, and make me more like a girly girl, I want a girl to use a ******* on me while I'm all dressed up in girly things!
    fun47 fun47 18-21, M 5 Responses May 13, 2014

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    I love wearing panties

    and sexy lingerie. I love wearing stocking and slutty heels. I love painting my toes it makes me feel so feminine. I want to dress up and be a mans play toy. being with a straight married man is a big fantasy of mine ive done it once lol. It was amazing. I want to give a man a...
    deleted deleted 26-30 7 Responses Mar 13, 2014

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    Anybody seen the book Help!

    I think I'm a sissy!? It is right on target! http://brassiered.com/helpithinkimasissy/index.html
    Chares184 Chares184 46-50, M 2 Responses Dec 6, 2014

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    I am a depraved diaper sissy,

    anything goes with me. There are no limits, I am looking for somebody to message with and humiliate me. Pls send me messages
    diapeelover23 diapeelover23 18-21, M 1 Response Oct 13, 2014

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    I never thought of being a sissy.

    While in college, it was obvious that I was not to dominate any of the men, but rather was there to make sure they were very satisfied. The guys told other guys I was available, and easy. I always was the female in the sack.
    donn2 donn2 61-65, M 5 Responses Aug 11, 2014

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    Sissy Sex At The Drive In.

    I remember when I was a teenager many years ago we used to go to the drive-in theatre almost every weekend during the summer. It was the best thing to do if you didn´t have a party to crash or money to spend at clubs. It was also the best place to have sex if you couldn´t...
    Sissydoll56 Sissydoll56 56-60, M 27 Responses May 22, 2012

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    last night i got to dress up

    and go out on a date with a very attractive and respect full man. we sat down to dinner and watched a movie at his place. it was amazing! he showered me with compliments and affection. i had the most amazing time
    tinatimmy tinatimmy 22-25, M 2 Responses Feb 9

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    diaper sissy with small pee pee looking

    for degradation and humiliation in my messages ASAP. Please message as soon as possible.
    diapeelover23 diapeelover23 18-21, M Oct 22, 2014

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    Getting smaller - I've noticed that

    since relations with my wife (continued below)
    Bellringer2c Bellringer2c 56-60, T 4 Responses Sep 28, 2014

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    Sissy is derived from sister it is a pejorative

    term for a boy or man who violates or does not meet the traditional male gender role. Generally, sissy implies a lack of courage and stoicism, which are thought important to the male role. A man might also be considered a sissy for being interested in traditionally feminine...
    CdKimmi CdKimmi 66-70, M 3 Responses Sep 12, 2014

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    More to follow!

    A while ago I had a girlfriend. We met through a friend. She knew I was interested in guys but didn't mind, actually - she told me that she loved gay boys, and loved making them have sex with each other. She told me that she was going to make me much, much more gay that what I am...
    girlydimpale girlydimpale 18-21, M 7 Responses Sep 2, 2012

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    Loving Being a Sissy Maid

    i worked at fairplay in staten island ny for two years and every tuesday i came to my mistresses house and did all her chores.since she runs a shop for girls like us and she also does makeovers i became one of her maids.i always came to her as a girl and i was able to buy nic...
    phylisanne phylisanne 66-70, F 5 Responses May 15, 2008

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    small pee pee diaper sissy looking

    for humiliation and degradation ASAP please message
    diapeelover23 diapeelover23 18-21, M 2 Responses Nov 28, 2014

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    Today I have the whole house to myself with no

    one it! So I get to dress up like a girl completely! just uploaded more pics go check them out!
    mrman77 mrman77 22-25, T 5 Responses Apr 4, 2014

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    I am definitely becoming more fem every day.

    Over the past two weeks, I've purchased several women's tops. Last week, I went out wearing a women's top with jeans and makeup. When the women at starbucks handed me my iced coffee, she called me hun :)
    Lilly292 Lilly292 41-45 1 Response Oct 6, 2014

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    .... Schoolgirl Who Likes To Have Her ***** Filled When Dressed. (Updated with new pics of me)

    Currently, my favorite is to get dressed up when my wife is out of the house running errands and I know she will be gone for awhile. I have aquired several very short tartan/plaid schoolgirl skirts from the local thrift store that I can barely get over my hips ($1.00 each from...
    deleted deleted 26-30 19 Responses Dec 8, 2011

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    I'm a 71 year old crossdresser

    and I have strong feminine feelings and urges all of the time. To satisfy those urges, I need to wear a bra, panties and occasionally have a need to dress fully en femme. In addition to my being a crossdresser, though, I also am a sissy because I love to serve and to satisfy...
    DonnaSue10 DonnaSue10 66-70, M 4 Responses Sep 25, 2014

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    I love to talk about

    and look at girly clothes, be great to be able to go shopping with someone but is there anyone here who would like to chat about clothing and girly stuff?
    cdjanine cdjanine 41-45 8 Responses Jul 21, 2014

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    mliza301 mliza301 22-25, T 4 Responses Apr 18

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    I joined alt.com a few months ago.

    I have to say, I have gone through quite a transformation over the last six months. A year and a half ago, if you had told me that I would be meeting with another sissy for an intimate encounter, I would have told you that you were crazy. Right now, I'm in communication with...
    Lilly292 Lilly292 41-45 3 Responses Jul 30, 2014

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    The Sentence. (Part Four.

    ) On returning with my Mistress, she informed me that so far all I have done is pay the emotional fine, now I must carry out my sentence. She further explained that she will instruction me on what I must do once we arrive at her place. The rest of the conversation was...
    chloesiobhan chloesiobhan 56-60, M 7 Responses Mar 9, 2014

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    From Lady Lovin Jock To A Sissy **** ****

    Hey there, I now go by the name Kristi! Im 24 years old and up until recently i was a 100%straight jock man that enjoyed the ladies probably more than i should of... Recently while in a horny haze i truly ACCIDENTALLY stumbled onto a video on fem/sissy blackmail of a husband, to...
    AFslut4u AFslut4u 22-25, T 4 Responses Jan 20, 2012

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    Sissy , i really don't like

    that term. But i like to wear heels and mini skirts and hose and love long hair. i love to serve others. i played football as a wide receiver for 17 years on a semi pro team. hang around a lot of guys and get lots of hugs from them. they don't know about my dressing.
    slavesindee slavesindee 56-60, M 2 Responses Sep 24, 2014

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    My Sisters Sissy

    When I was seven I started spending summers in Michigans Upper Penninsula with my much older unmarried sister who I adored for getting me out of my Fathers abusive reach. She was always my cool sister as she always had a new convertable, always dressed nice, always pretty. She...
    prettylace prettylace 56-60, M 128 Responses Nov 14, 2010

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    That's pretty much it.

    I've been curious about crossdressing and feminization for as long as I can remember, but I've always supressed and denied it. I've told myself a thousand ways why it's wrong for a male to dress in Women's clothing, but after 21 long years, I'm finally giving in and accepting...
    SissyslaveVanessa SissyslaveVanessa 22-25, M 8 Responses Aug 12, 2014

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    I am a sissy because i like to wear womens

    clothes and act girly, i also like to have sex with men but i also like women too, so i guess i'm bisexual, when i have sex wih a guy, i have to be dressed up appropriately, normally in a sexy nghtie or some hot lingerie
    NicolaCD NicolaCD 51-55, M 4 Responses May 9

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    Hi, I'm looking to chat with someone

    who would be willing to help me overcome the last of my inhibitions that are preventing me from becoming the sissy slave I so desire. A part of me wants to become intimate with another sissy or pre op, but those pesky voices keep me from doing so. Your loving sissy gurl...
    Lilly292 Lilly292 41-45 3 Responses May 11

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    The Day It Came To Me I Am A Sissy

    Well I have been wearing pantys and things from the age 7. In the late 80's I had a job on the road as a service man,the job took me all over the state mostly by myself. Most day I would get up and after I cleaned up I put on a bra and pantys then my work clothes. I would get i...
    laciebottoms laciebottoms 56-60, T 4 Responses Apr 15, 2011

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    Visit To The Bath House

    Many years ago I read on a local gay newspaper, about a sauna for this community. Meaning the gay community. After giving it plenty of thought I finally built up the courage one Saturday to go and try out this place. I found the place easily and after driving around the block a...
    Sissydoll56 Sissydoll56 56-60, M 22 Responses Mar 15, 2012

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    My Wife's Sissy

    Having been through two other failed marriages because of my feminine ways I choose to tell my future wife about who I was. Fortunately for me she has a "thing" for my soft feminine side and we have escalated from there. We buy ALL my clothes together and I have become quite good...
    marysgirl marysgirl 61-65, T 5 Responses Sep 7, 2011

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    When My Wife Found Out That I Was A Sissy

    So about 3 yrs ago my girlfriend at the time was a work so I thought. Well she left for work. So I figured I would dress up and do some house work. Well as the time went by I was danceing singing like a sissy. When she walk in the door. The look on her face surpirsed that I was...
    Sissyjim3 Sissyjim3 31-35, M 3 Responses Aug 21, 2012

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    I Guess Its Official.

    Last night my wife called our dog a pansy, and joking i said don't talk about me like that. Her reply was "if i was going to call you anything it would be a sissy".  and now a little more of an update yesterday afternoon i ordered my first wig, so i can be a little more passable...
    AmberRosecd AmberRosecd 31-35, T 11 Responses Apr 17, 2013

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    Mistress Guided My First *********** Experience

    This is my true tale of the first time I was 'encouraged' to suck a real man... I had seen a few pro dommes in person by the time I was in my late 30's. Also chatted with some phone dommes occationally. Well, I had been chatting with this phone domme for a few months. She...
    tvshannon tvshannon 51-55, T 24 Responses Jun 1, 2012

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    i have found a chastity master ep im

    so excited hes going to put me in a pretty pink chastity device lol i cant wait to finally be the sissy slave i always wanted to be ill keep everyone posted lol text me if you want some pics and videos lol
    Samantha779 Samantha779 22-25, M 3 Responses Dec 31, 2014

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    NOBOYS NOBOYS 18-21, F 2 Responses Sep 4, 2014

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    My First Time.

    My first time? Well, I can't remember the moment precisely for it happened a very long time ago. As a young boy I was apparently straight. I'd had a crush or two on girls although I was extremely shy to do anything about it. I'd ********** to fantasies with girls or movie stars...
    Sissydoll56 Sissydoll56 56-60, M 29 Responses Mar 10, 2012

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    if any female want to me to model

    for them. reply back and ill give you a Skype/email
    sissy699 sissy699 18-21, M May 22, 2014

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    I've always thought the term "Sissy" was WAY

    too limiting. I've never considered myself a "sissy" even though most of the time I wear woman's panties and even pantyhose under my male clothing. And (mostly in private) I dress up completely in woman's clothing--wearing makeup and all. And although I'm at least mostly...
    RayanneA RayanneA 56-60, M 5 Responses May 23, 2014

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    Caught Lying To My Mistress. (Part One.)

    Enjoying the delights of this scorching heatwave in England last week, I was enticed to tell my gorgeous, understanding Mistress a total lie. She rang me whilst I was at work, stating that she required my services as soon as I had finished, then she would come and pick me up. I...
    chloesiobhan chloesiobhan 56-60, M 9 Responses Jul 19, 2013

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    Being the Real Me

    I finally decided to quit fighting & allow my feminine side to come out to the world.  The "she" part of me was dominant & I was tired of living the macho charade  which brought little else but frustration & disappointment. I wanted to be ME, the...
    dvdfg9 dvdfg9 41-45, T 17 Responses Mar 1, 2008

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    A Couple Used Me

    I once answered an ad to play with a couple. I was a cross-dresser and so was the husband. It turned out that the wanted to just use me. yes the husband did cross-dress and his wife was cuckolding him with her boss which he husband enjoyed. The husband had a 9" thick tool I can...
    glorialamuse glorialamuse 56-60 10 Responses Jan 23, 2011

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    I don't think I'm a sissy yet,

    but maybe I'm in danger of entering sissy territory. I have 24 pairs of my own panties. That's not a lot for a man to own, is it? Of course I also own several skirts, some stockings, a corset and at least one garterbellt. I just love the feeling of satin and the way I look in...
    VictoriaFredericks VictoriaFredericks 36-40, M 6 Responses Aug 14, 2014

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    Sissybitch21 Sissybitch21 22-25 Sep 27, 2014

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    Went outside dressed in a very short baby doll

    to put the garbage in the can. when I tried to come back in the house, my cat got out! I tried to catch him, but my call to Mistress about the cat, made her turn the outside light on to see better! Well, there I was, outside in a really short nighty, trying to catch our cat...
    michelle4446 michelle4446 51-55, T 7 Responses Sep 10, 2014

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