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I Am a Sissy

Personal Stories, Advice, and Support 3,980 People

    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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    Did It! (Follow Up To: Tonight’S The Big Night)

    The deed is done. I did it. WE did it. First my wife shaved every body hair I had from the neck down not including my arms. Shower and then perfume she picked out. Next was the see through g-string and fishnet pantyhose. Then the cute little lady bug costume. Finally I put on...
    2muchexp 2muchexp 51-55, M 2 Responses Oct 28, 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 21 Responses Jun 1, 2012

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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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    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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    I Am A New Sissy!

    Hi all this is a big deal for me as I have never shared this secret with anyone! Im 21 and I have been cross dressing since I was 9 it started by me try my step moms gorgeous red Lacey corset with matching underwear and red stockings I felt amazing! I loved the Lacey feeling on...
    SissyBryany SissyBryany 18-21, M 3 Responses Nov 4, 2013

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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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    Tonight's The Big Night!

    OK tonight is the big night. Tonight I’m going out with my wife to a huge party in Houston.  I’ll be in my panties, stockings, petticoat, heels and this cute little lady bug costume.  I’ll have in my fake ****.  The world will finally see me as the sissy boy I really am...
    2muchexp 2muchexp 51-55, M 2 Responses Oct 26, 2013

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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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    Sissies

    i really love men u submit to women n her whims n fancies .. public calls them sissies .. n they r really useless worthless sissies .. but i respect them more than the alpha males ... all these "so called alpha males r arrogant bastards " i love sissies esp. wen who obey to their...
    ACHAMA ACHAMA 46-50, F 16 Responses Mar 19, 2011

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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 1 Response 4 days ago

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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 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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    Sissy Or Shemale Or What ?

    i become to understand what is my nature when i have 40 years old. Younger i used to wear my auntie's panties (she didn't know that....), one time at 17 i go in a gay place with girly outfits (i've stolen a dress of my sister, and panties too), after that i was ashamed...
    frenchsissy frenchsissy 51-55 1 Response May 5, 2010

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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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    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 6 Responses 6 days ago

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    Every time I think i've stopped I just end up

    back here. I should probably go back a bit, not all the way to the start but rewind 1 year. I had just started college. I only had a few friends who I knew well and knew me well and knew that I wore dresses. I thought it best if I didnt start wearing skirts until I had settled...
    agirlatheart8 agirlatheart8 18-21, T 8 Responses Jan 9

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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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    S.I.S.S.Y.

    I am a sissy, all ways have been and always will be. When I was little, while most boys my age where playing with hot wheels and other boy things I was secretly playing with Barbie dolls which I stole from my cousin, while wearing her Disney princess panties which I also stole...
    justasissyboi justasissyboi 22-25, M 3 Responses Nov 11, 2013

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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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    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 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 28 Responses Mar 10, 2012

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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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    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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    I Am A Sissy, An Adult Baby, A "housewife" And A Female-led Tiny Penis Husband

    I am in my CB 6000. I feel like i have been neutered. I have a clitty/pee-pee but i can't do anything with it. :-( Mommy says she like the way it looks and she likes having the chastity device on me and she likes that now she can leave the house and trust that i won't be able to...
    kent1973 kent1973 56-60, M 2 Responses Nov 26, 2013

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    sammi11 sammi11 41-45, T 12 Responses Mar 29, 2013

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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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    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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    As I've gotten more enmeshed in my sissy side,

    I've started to explore new things. I am communicating with another sissy. We will probably be chatting on the phone soon. I've given her both of my cell numbers, and believe it or not, I'm leaning towards agreeing to an intimate meeting with her. This sissy is definitely the...
    Lilly292 Lilly292 41-45 2 Responses Feb 1

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    My Life

    I was born to a single mother. Although men have been in and out of her life for the majority of mine, I never had a male roll model. But that only compensates for the male parental absence in my life. I believe..that my physical development has also played a major roll in my...
    xsugarpantsx xsugarpantsx 18-21, M 1 Response Oct 22, 2013

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    A Sissy CD Again For BBC And My GF - Oct 15th 2013 !

    My GF ( "jamieismy sissy' - she's here on EP ) and I placed an add on CL to find Lushes Black **** for my GF. We got a ton of responses and narrowed it down to just one ..."Mike" Mike is about 25 (?) y/o, 6 ft, kind of "thug looking" - lots of tats, very polite to my GF - but...
    Jamieisasissy Jamieisasissy 36-40, T Oct 22, 2013

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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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    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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    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 26 Responses May 22, 2012

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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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    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 5 Responses Mar 9

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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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    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 13 Responses Apr 17, 2013

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

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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...
    DanniChan DanniChan 22-25, T 3 Responses Apr 9

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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

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    mrman77 mrman77 22-25, T 3 Responses Mar 5

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    Any got REAL MEN out there ready to build a life

    and a home with a beautiful pretty limitless prissy sissy boi wife? I am naturally effeminate, I talk like a girl and act like one and I need a strong masculine man in my life to treat me like the queen diva I am! If your interested please send me message with a link to your...
    FemGayBottom FemGayBottom 26-30, T 5 Responses Apr 11

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    I Am A Sissy...and I Admit It

    I have always loved to wear panties. Then I moved on to garters w/stockings and heels. I then started wearing my wife's bra's with panties...they make me feel so alive, so feminine. At first it was a need a drive that I didn't understand. I love women, I really do. There is...
    PrissySissySara PrissySissySara 36-40, M 8 Responses Jun 26, 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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    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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    SaphireTracy SaphireTracy 18-21, T 3 Responses Mar 14

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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 4 Responses May 13

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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 6 Responses Sep 17, 2013

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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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    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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    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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    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 132 Responses Nov 14, 2010

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