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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 234 People

    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 13-15, M 1 Response Nov 11, 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 11 Responses Jul 18, 2010

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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 13-15, M 3 Responses Dec 26, 2013

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    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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    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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    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 11 Responses Jul 18, 2010

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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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    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 3 Responses Jan 25, 2011

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    Related Experiences

    I'm 16 years old and my older sister (by 17 years) has agreed to let me stay at her house for the rest of the school year until mom gets back from visiting her brother. (I couldn't...
    ThatelfR ThatelfR 16-17, F 2 Responses 3 hrs ago

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    Any crossdressers in Northern Ireland? :) x 18 cd ni here
    Crossdressheels Crossdressheels 18-21 3 hrs ago

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    She asked my wife if she could sit on my lap in the car one day. I got hard and poking her in her couche and she told my wife and mother in law. They thought it was funny.
    rbowm031 rbowm031 31-35 2 hrs ago

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    I am falling for a crossdresser. I love him and who he is and I would never change him. I told my family, which consist of my mother and sister. Mom was accepting, my sister was...
    bbsw1963 bbsw1963 46-50, F 2 Responses Mar 24

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    Ok this is my first time writing about this and I am nervous about doing so. Ok i have crossdressed for as far back as I remember. The first time I can recall was at the age of 4...
    deleted deleted 26-30 4 Responses Apr 6

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    Okay so lets say my name is "Peter" and her name is "Anna" and my friends name is "Chris". Chris and i were really good friends. He was my first friend when i moved to Chicago. His...
    new29 new29 18-21, M 1 Response 6 hrs ago

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    I've been caught many times wearing my sisters lingerie and it's funny because my crossdressing started because of my sister. My sister and I are only two years apart and when we...
    Dirtyblondeslut69 Dirtyblondeslut69 22-25, M 6 days ago

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    I've always loved the idea of dating a crossdresser. I'm what some people might call a "tomboy" and I just always found the juxtaposition ( I that's the right word I'm not really...
    BrahmaDonna BrahmaDonna 22-25, F 16 Responses Mar 22

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    While we aren't biological sister's and im a crossdresser I love my little sister here on ep and I know she loves me shes cute sweet funny kind awesome and one of the best little...
    Nicolecdwolf Nicolecdwolf 13-15, T Mar 23

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    Aahh the nostalgia... Back into my sisters panties. Lol, my photo looks like a pair of boobs
    Jess967 Jess967 18-21, M 2 Responses Apr 10

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    My younger sister is very rude, dramatic, and very annoying. I used love my sister, I have pictures of me kissing her and hugging her as a child. Many pictures. She is like 15...
    ll0205 ll0205 13-15 Mar 30

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    I think my sister has to be the worst human being in the world. When she was a freshman in high school she started a rumor that she got pregnant and had an abortion. Her Junior...
    blisster blisster 26-30, F 1 Response Mar 28

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    I like Crossdressing. But I have never told anyone. Do you think I should?
    Pinklovemaddie Pinklovemaddie 13-15 3 Responses 4 days ago

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    I hate my older sister. I am a 15 year old korean girl. I had a decent life, and I have decent friends. I even have a boyfriend I really admire, but there's somebody who's always...
    mymood mymood 13-15, F Mar 30

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    I dont know when my cd begin..i my child hood my mom wears my sisters skirt and top,pants etc..mom always tell about my attraction to the girls properties.. so this will be the...
    deleted deleted 26-30 1 Response Mar 21

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    My sister is gonna give me her old clothes that fit tonight:) it has everything from underwear to dresses and skirts. message me if you want pics. Sorry for the no posting in a...
    Pantylova Pantylova 18-21, M 9 Responses Mar 22

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    I really want a slightly older sister to dress me up and teach me everything it is to be a woman. If anyone is willing to do this pls let me know
    apwnn apwnn 16-17, M 1 Response Mar 25

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    After stumbling across a cross-dresser in p**n, all I think about when I'm in public out of my feminine personality is that I wish I was wearing more than just my sisters tight...
    Jess967 Jess967 18-21, M 4 Responses Apr 7

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    Got into my sisters bikini and loving it!! Pink frilly bottoms with white and baby pink stripes and a frill top with stripes and polka dots!! Lovin this
    Jess967 Jess967 18-21, M 4 Responses Apr 8

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    Tried some of my sister clothes on did a sexy secretary look, pics on profile
    CarlyGirly2040 CarlyGirly2040 18-21, M Apr 9

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    One of my first times I was around 16 I tried on one of my sister's miniskirts and then I was hooked. And of course I was always attracted to girls in knee socks, so I had to try...
    schoolgyrlKaren schoolgyrlKaren 41-45 2 Responses a week ago

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    I found this site so please give advice if you have any. I am currently 19 years old. I am really short. 4'9 to be exact. I was the tallest in my class kindergarten through 2nd...
    veryshort4 veryshort4 18-21, M Mar 25

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    Um... Hi im a aspiring crossdresser Id kinda like help crossdressing if anyone would want to My kick is josef3303664
    deathtrap12 deathtrap12 18-21, M 2 Responses 6 days ago

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    Growing up was fun for me... Until like around 7th grade. My sister is 3 years younger than me. I'm 14 and she's 11. I've always been taller than her until the beginning of 7th...
    unclecj4 unclecj4 13-15, M Mar 24

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    As I'm making the transition from male to female, I have made my work aware of this and will be going to work as Lucy full time from the end of April :) My colleagues were told in...
    LucyTG LucyTG 26-30, T 5 Responses Mar 25

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    My boyfriend and I have been dating for over a year now, and I am completely in love with him. He' my best friend and the love of my life. I can't imagine life without him. He...
    lithium123 lithium123 22-25 6 Responses Mar 30

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    Hate is a very strong word I would like to use dislike.. Because when it comes down to it I do love her. I have four sisters and one of them is only a half My dad had her in a...
    FreeThoughtz FreeThoughtz 22-25, F 1 Response Apr 4

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    I have an older sister she is 17 and i am 15 i always feel pretty i look at myself and i don't think my sister is preetier than me, when we meet people they tell us we are like...
    Victoriastyles Victoriastyles 13-15, F 2 Responses 13 hrs ago

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    I have a thing for guys who crossdress:3 I just find them so appealing!
    alpaqqa alpaqqa 13-15, F 1 Response Mar 19

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    My first crossdressing experience was with my Mum's knickers. I remember I wanted to recreate a scene from a film where I saw a beautiful woman walking around in just her underwear...
    LucyTG LucyTG 26-30, T 4 Responses Mar 19

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    I'd love to crossdress but I'm scared of doing so, because I'm worried I won't be able to like what I see in the mirror when I do so. But I adore make-up and women's clothes.
    lyolyo1 lyolyo1 22-25, M 4 Responses Mar 20

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    It really is a fantastic feeling slipping in to a nice skirt or dress and complimenting it with other nice items :) I love wearing dresses and the feeling of how free everything...
    LucyTG LucyTG 26-30, T 4 Responses Mar 20

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    If there any girls here willing to add me or help with a 0% chance of girls clothes for me to wear or you wanna be friends please message me i am a male crossdresser and by the way...
    lovepink73 lovepink73 13-15, M 1 Response Mar 22

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    I love wearing girls clothes the more girly the better. I'd love to chat to other crossdressers so send me a message :)
    deleted deleted 26-30 1 Response Mar 25

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    I crossdress every chance I get. My wife knows but does not participate.
    cdtommy cdtommy 66-70, M 2 Responses Mar 28

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    I absolutely adore crossdressers. I kind of run a small business where I help boys and men get dressed up. I would love to hear all of your stories. Any age can message me, and I...
    ShainaNichole ShainaNichole 18-21, F 12 Responses Mar 29

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

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    I live in GA and would like to meet other crossdressers and transgenders.
    sexidancer sexidancer 41-45, T 2 Responses Mar 30

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    Any sissy or crossdressers here from central Ohio? I'm a sissy admirer and would love to meet some girls! Muah!!!
    ChrisP1279 ChrisP1279 31-35, M 1 Response Mar 31

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    Anyone from Harrogate or North East Yorkshire that crossdresses or anything to do with that pls message me
    apwnn apwnn 16-17, M 2 Responses Mar 31

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