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I Am a Sissy

Personal Stories, Advice, and Support 4,023 People

    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 12 Responses Apr 17, 2013

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    My first experience with being bi

    and wearing panties came when I was about 11. At my friends house we would always go to this room that was at the back of the house by the laundry room to watch TV. His sister usually lived in it but she had been out of town for awhile I can't remember why. Well my friend was...
    Bradhowd Bradhowd 22-25, M 2 Responses Aug 14

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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 7 Responses May 15, 2008

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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 24 Responses Mar 15, 2012

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    hi im saphire im really slutty

    even if i dont always send pics and i love to chat so if you got the time swing my way for a little play
    SaphireTracy SaphireTracy 18-21, T 2 Responses Feb 9

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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 7 Responses Aug 14

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    mrman77 mrman77 22-25, T 3 Responses Mar 5

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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 5 Responses Apr 15, 2011

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    My Dream For First Real Anal

    I'd be dressed to the nines wearing a plaid short mini skirt that has mid ruffles and a lace hem it'd be so short on me that while walking I'd get a peekaboo butt then I'd wear classic white Cotten panties simple and cute they'd have two pink bows on the front for each leg the...
    Marissatgsissy Marissatgsissy 18-21, T 9 Responses Nov 21, 2012

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    Conversion To Feminization

    I'm a35 year old separated married man who for many years has been attracted to experiencing sex as a sissy.My wife told me very early in our relationship that she was in no way receptive to being a part of these activities and as a result we went our separate ways.After about...
    Stefffi Stefffi 36-40, M 10 Responses Jul 28, 2010

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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

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    hey saphire here wondering

    if theres any doms who would like to play, im very board and need so master to love me.
    SaphireTracy SaphireTracy 18-21, T 1 Response Jul 7

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    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21, T 1 Response Jul 23

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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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    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 18-21, M 11 Responses Aug 12

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    Most masculine men don't love pretty little

    smooth effeminate bottom Bois like me so it would be so cool to meet a great masculine guys that a are cool and even actually love precious little queens!
    FemGayBottom FemGayBottom 26-30, T 1 Response Apr 9

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    I am a 16 year old ****sucking,

    submissive boy , who loves to suck **** , and take it in the but , and loves wearing panties. I snuck out last night at like 12:00 and went for a night run in a singlet and the pink pair :) i ran thru a bush walk and bumped into some drunk men haha No pants, just a singlet and...
    Cameronsissy Cameronsissy 22-25, M 3 Responses 6 days ago

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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 51-55, M 10 Responses Mar 9

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    I am a black closet sissy I would love to have

    a dominate white man who loves raceplay message me if you are in the DC metro area
    sissykhandi sissykhandi 46-50, M 2 Responses Apr 6

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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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    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 4 Responses Apr 4

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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 6 Responses May 23

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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 21 Responses Jun 1, 2012

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    sammi11 sammi11 41-45, T 5 Responses Dec 28, 2012

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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

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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 61-65, M 3 Responses Sep 12

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    SaphireTracy SaphireTracy 18-21, T 3 Responses Mar 14

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    Today i lost my virginity to a group of girls

    in my ballet class. IN MY FAVORITE leggings
    sissy699 sissy699 18-21, M 1 Response Feb 6

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    NOBOYS NOBOYS 18-21, F 2 Responses Sep 4

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    I like to wear pretty woman's clothes

    and lingerie. I love to paint my nails and wear makeup, lipstick and heels. If that's not a sissy I don't know what is. I'm happy.
    MsRobyn MsRobyn 51-55, T 9 Responses Feb 2

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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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    One Of Those Difficult Times

    In the early days of my journey, I was dressing quite a lot but none of our friends and certainly no family knew about my femme interests. I had, however, finished beauty school and was working doing hair. My step daughter was at the house for the weekend so that I could do her...
    MsMitzieKelly MsMitzieKelly 66-70, T 4 Responses Sep 17, 2013

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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

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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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    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 7 Responses Sep 7, 2011

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    My Name Is Dana .....and I Am A Sissygurl...just A Reflection Of The Past Ten Years

    Recently, I had a rather heated exchange with a sibling, my older sister. I think she thinks it is her time to "heal me". However, during our exchange, she asked a simple, but direct question and it made me think about everything that has transpired over the past ten years. Her...
    danagurl danagurl 26-30, T 22 Responses Sep 13, 2011

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    My Wife Returned

    Two weeks ago, I was sleeping to night, when my ex-wife arrives, wakes me with a slap on the *** and say - I'm back. At the time I froze. And she continued - you liked so much of live like my wife, who continues sleeping in her nightgown. I bet you felt my absence. Then now I'm...
    helinha helinha 36-40, M 12 Responses Oct 28, 2012

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    I am a *** hungry **** worshiping transexual

    loving sissy *** ****. And I ******* love it! I do not think we should be ashamed to say exactly what we are. Who we are and what we enjoy no matter how other people think of you afterwards So yeh I am a sissy and I love it he he Jasmine Xx
    tvsissiejasminee tvsissiejasminee 22-25, T 7 Responses Dec 8, 2013

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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 4 Responses Aug 21, 2012

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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 8 Responses Sep 2, 2012

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    I left my curtains open

    so my neighbour cud see ;) I'm such a slutty sissy boy hehe
    Cameronsissy Cameronsissy 22-25, M 1 Response 6 days ago

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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

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    sammi11 sammi11 41-45, T 13 Responses Mar 29, 2013

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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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    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 142 Responses Nov 14, 2010

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    After 45 years as a macho male,

    I started fantasizing I was a sissy. For the last few months I have been playing ( fetishizing?) at it. I have finally come to the realization, I am a sissy.
    wpg90 wpg90 41-45, M 5 Responses Apr 27

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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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    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 3 Responses Sep 10

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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 28 Responses May 22, 2012

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    So my girl friend and I have been talking about

    getting a sissy together as co. doms mistresses if you will. So were looking at names any sugestions .
    SaphireTracy SaphireTracy 18-21, T 3 Responses Aug 25

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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 10 Responses Mar 13

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    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 13 Responses Jun 5, 2013

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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

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    Never been sure what to class myself as,

    crossdresser, transgender sissy. Really im all 3 but i enjoy being a sissy allot more. Here i am in a bright pink satin dress with petticoat, short enough my nappy pokes out underneath and i love it. My dream is to dress, act and like like a sissy 24/7, even have a job that...