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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 227 People

    I Miss My Sister

    Last week I was informed that my sister was found dead at the age of 50. That was a great shock for me as she was the only other remaining member of my parents' family, the last link with my childhood after my parents are gone and only some distant relatives remain outside my...
    tightsvirus tightsvirus 41-45, M Oct 14, 2013

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    Actually she was more

    or less directly responsible. I have posted the story of how she caught me in her clothes and blackmailed me into doing it more just for her amusement. I pretended to hate the whole experience but secretly developed a passion for it all these years later. I still do it in front...
    nyloncrush nyloncrush 41-45, M 1 Response 5 days ago

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    I Told My Sister That I'm Tg

    I told her I was transgendered, and she didn't believe me. So I plastered on a smile and watched her walk away.
    Soarre Soarre 18-21, T 2 Responses Jan 25, 2011

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    I Mustered Up The Courage And It Paid Off

    I spent my childhood and teen years dressing up in my sisters clothes and occasionally using her makeup. I used to try on her dresses, skirts and blouses, her hells and nylons, and even her underwear. She went to school for fashion design and now works in the fashion industry, so...
    iheartdressing iheartdressing 26-30, M 13 Responses Jun 28, 2013

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    Sister

    I told her a year ago. She was suprised at first but then got used to it. She helps me get dressed in my dresses and makeup. She helps me with nail polish. I also love wearing her leggings and skirts.
    redleg19 redleg19 16-17, T 2 Responses Nov 11, 2013

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    Ever since i was little i liked wearing girls

    clothes. No one paid attention because they thought it was a phase. As I got older I would sneak into my room which i shared with my sister and wear her clothes. I did that every time she was gone. I would wear anything and made sure to cover it up. Sometimes she would find her...
    redleg19 redleg19 16-17, T 4 Responses Dec 26, 2013

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    A Blow To My Confidence

    I told my oldest sister that I crossdress. I told her as a lead in to the fact that I intend to become female. We were always very close. But not any more. She just couldn't handle it. Now I rarely see her, and when I do, we just nod at each other. My sister is lost to me...
    RoseViolet RoseViolet 46-50, F 12 Responses Jul 18, 2010

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    She Didn't Like That Too Much

     So I told her and things did not go well you could say. I told my mom too and both don't take kindly to the idea of me crossdressing. And so I am back where I started, dressing in total privacy. Huuuhhhh -_-
    Someguy94 Someguy94 18-21, M 6 Responses Jan 28, 2010

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    Crossdresed Me By Sister In Saree.

    I am male 36yrs. I like cd in saree, so I went aunty house her house is outside the city.There aunty daughter stay (my cousin sister). I told in friend place get-together was happen in last Sunday! In that chit pick I got chit to ware saree!!!She told me it good, I will help in...
    smks smks 36-40, M Jul 4, 2013

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    No Change

    I recently told my sister that I am a cross dresser.Initially, she was very surprised, never guessing that I might do this. She appreciated how hard it must have been for me to tell her. I was prepared for the cold shoulder, but instead got "Oh, Okay". Later in the week she...
    Becnme Becnme 56-60, F 10 Responses Jul 18, 2010

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    Related Experiences

    I have two sister's. I have fantasies about us having a naughty lingerie party :)
    SissyTeenNikki SissyTeenNikki 18-21, T 5 Responses 2 hrs ago

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    My first crossdressing was when I visited my sister at her house she is 25 years old and I was 13 years old today she was out so I was by myself I got bored so I went up to her...
    cutewolf197 cutewolf197 16-17, M 1 Response Mar 29

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    I wish I could crossdressing all the time, but my wife would freak . I feel stifled.
    simonsteane simonsteane 46-50, M 3 Responses 6 hrs ago

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    Any crossdressers want to talk I woke up horny I don't know and I feel sexy
    yuyu0079 yuyu0079 18-21, M 6 hrs ago

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    I've noticed most crossdressers on here are either from the UK or the US, are there actually any mainland Europe CD's on here ?
    PersonOfUninterest PersonOfUninterest 18-21, M 5 hrs ago

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    I never did it with either, yet they both played a crucial role. It began with my mom wanting a baby girl. She was so certain that I'd be a girl that she insisted on girl's things...
    AlbertSAT AlbertSAT 66-70, M 10 Responses Apr 9

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    Soo i had this fantasy: I had moved schools and for a school assignment i was partnered up with a guy called James. James was a kid that was shy and doesn't have too many friends...
    Stephsiszy Stephsiszy 22-25, T 4 Responses Mar 30

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    I am extremely lucky to have the group of friends that I have! Crossdressing has been a part of me since I was a little tyke, and I've kept it a secret all this time. I finally...
    kins101 kins101 26-30, M 2 Responses Mar 30

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    Hi. This is really the first time I'm really putting this out there. I've been secretly crossdressing on and off since I was 6. I'm turning 18 in July so it will be 12 years now. I...
    DecrepitSundew3 DecrepitSundew3 16-17, M Apr 1

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    I want to have a sister so bad
    AndyWickedclown AndyWickedclown 16-17, F 16 hrs ago

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    I love my sister. We have so much in common and she is always there for me. She was there when I had a mental break at school and stayed with me until I was placed in a psych ward...
    Ivygirl96 Ivygirl96 18-21, F 1 Response 4 hrs ago

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    Uhhhhggggggggggg. I have been having a crazy week. A bunch of people at work took the week off so I am working over time. And having a super rude sister just makes it worse. It's...
    LoveisBeautiful5013 LoveisBeautiful5013 18-21, F Apr 9

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    I was 14 at the time and was going to be home alone all day. My mother had this beautiful red nightgown hanging in the bathroom. It was soft and silky. I tried it on and it felt so...
    Stephaniegirl226 Stephaniegirl226 36-40, M 2 Responses Apr 1

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    Many people even seem to be angered by my crossdressing. Men are generally the most offended. Seeing a full figured girl wearing mens clothing is so damn offensive to them. I've...
    Annaelaine Annaelaine 16-17, F 3 Responses Apr 1

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    My sister has been mean and abusive all of my life (12 years). I'm sick and tired of her! Everyday she tells me to do all the chores and when I ask for help she yells at me. She is...
    hinesbv hinesbv 18-21, F 2 Responses Mar 31

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    Life's just so hard at times. A few months ago i was secretly crossdressing daily loving life, then the next thing i know i stop crossdressing and start going to the gym to make...
    Tyrone147 Tyrone147 18-21 8 Responses Apr 3

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    Took some of my sisters clothes and took a pic before she noticed! I don't really like the picture itself but the clothes felt so good!
    TrulyAGirl TrulyAGirl 13-15, T 4 Responses Mar 19

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    growing up I knew I was different wearing my sisters clothes at age 12 ..I wanted to dress up be girly then ...I knew I was gay to had first crush on neighborhood boy...now in my...
    spencersawtelle spencersawtelle 41-45, M 1 Response Apr 8

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    I started about 11 yr old when I had the urge to wear older sister's (16) panties she left on bathrm floor after showering. I remember how great they felt and the tight pressure...
    robbi95 robbi95 46-50, M 9 Responses 6 days ago

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    My teacher is so cute but he's married and won't be my friend either and like I never told him I like him
    jujufruit12345 jujufruit12345 18-21, F 1 Response 2 hrs ago

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    I don't feel welcome in the crossdress img community as I'm a female who dresses as a male. I don't know if it's just me personally or because we can't relate being to different...
    miskia0917 miskia0917 18-21, F 1 Response Mar 19

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    Recently I started feeling more and more like moving forward with the things that make me happy and excites me such as piercing my ears or buying some new stilettos. But The truth...
    Danairis Danairis 46-50, T 3 Responses Mar 22

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    Im a 21 year old and I want to meet and talk to crossdressers! I was in to crossdressing myself when I was younger but got out of it. Ive always just had an attraction to men in...
    nick191 nick191 18-21, M 3 Responses Mar 22

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    On weekends, unless I am going out on the town, I typically wear women's jeans, or capri pants to run my errands and do housework. I always wear makeup and try to look and be as...
    dianecarr dianecarr 61-65, T 4 Responses Mar 29

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    I am 15 years old crossdresser, maybe i was born a boy but its not me i want to be a girl i love wear sexy panties bras bikinis sexy lingeries and i love do my make up its me and...
    barbaraxoxo barbaraxoxo 13-15, T 1 Response Apr 3

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    I went to a friends fancy dressed birthday party.i was wearing my blond wig pvc skirt hose and knee boots she did my make up.i was the hit of the party i had my legs rubbed and my...
    Brandie9 Brandie9 31-35, M Apr 4

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    I recently found out my guy is a crossdresser. It took me completely by surprise, lots of crying and confusion. Because I love him I chose to stay. He only wears womens bra and...
    georgetta1994 georgetta1994 18-21, F 4 Responses Apr 7

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    I was 5 years old when my Mom caught me wearing her red lipstick, and posing in the mirror with a cigarette. She didnt freak out. She just wiped my mouth and told me I was very...
    sillytilly2012 sillytilly2012 51-55, T 3 Responses Apr 8

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    I would love nothing more than to make a few friends....been a crossdresser since childhood.....but as you know life as a crossdresser can be a lonely one
    jessilynn2015 jessilynn2015 41-45, T 2 Responses Apr 9

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    I have two sisters now.My oldest sister Cecilia was out of the house as I was growing up, so It was pretty much just me and my parents. But I was so surprised and excited when my...
    justerika justerika 26-30, F Mar 23

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    I really screwed up. One of my best friends (let's call her Jade)'s brother passed away a week ago. My other best friend (let's call her Angie) told me. She private messaged me...
    ArtLover24 ArtLover24 22-25, F Apr 5

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    My younger sister is 38 and I'm 44. She hates me for as long as I can remember. I was hoping that when we get older we would mature and be very close. Things seems to get worst...
    sparklyivy5 sparklyivy5 41-45, F 1 Response