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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 235 People

    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 7 Responses Jan 28, 2010

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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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    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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    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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    Great

    Funny I was scared to tell her so I flipped a coin, I was great she completely understands and loves it she loves to dress me up she lets me wear any of her clothes and the best is she understands I am not gay , I told her last Friday we dressed up all she even asked if I...
    mazzz77 mazzz77 18-21, M 1 Response Mar 29, 2010

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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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    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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    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 15 Responses Jun 28, 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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    She Knew

    Although my sister saw me many a time wearing dresses while we were growing up, our lives separated when I went into the military and she went off to marry her first husband. She moved to Georgia and I stayed in Ohio. A few years later her marriage dissolved and she moved back to...
    Melodie13 Melodie13 61-65, M 6 Responses Feb 19, 2012

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    Related Experiences

    When I was 14 I started crossdressing. My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties...
    Stephaniegirl226 Stephaniegirl226 36-40, M 9 Responses Sep 13

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    It was my wife. I guess she couldn't help it but she told her mother and her sister and goodness knows who else is in that circle now. Anyone else had that happen to them ??
    LibbyLee LibbyLee 56-60, T 4 Responses Sep 12

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    found a bag of my sisters old clothes at my parents place well staying there when they were on holidays so like any crossdresser would do i looked though found somethings i liked...
    vjss vjss 22-25, M 4 Responses a week ago

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    Call me crazy, but a part of me almost wants to tell my older sister that I love crossdressing. Be like, "you know why I get all weird when you ask to use my pick up truck?, it's...
    JessicaCD20 JessicaCD20 18-21, M 4 Responses 2 days ago

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    I started crossdressing in my mother's clothes when I was 10 and became addicted to it almost immediately. A few years later, my little sister caught me at it. I became submissive...
    cdchrystal cdchrystal 46-50, M 5 Responses 1 day ago

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    Hi guys this is my second story and I'm still not sure if I'm doing it right but anyway here goes. My desire for crossdressing lessoned a little when I met someone, and I tried my...
    youngsissy14 youngsissy14 18-21, M 2 days ago

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    My little sister two: Let me start off by saying that I really didn't want to do this story but people keep asking me. That being said any perverted comments will be reported to EP...
    FatTeen11 FatTeen11 18-21, F 3 Responses a week ago

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    I feel I must give you a little back story. My sister is about 4 years younger than me and has always had a bit of a competitive side. I guess I was never paying much attention to...
    Trinitey779 Trinitey779 31-35, F 14 hrs ago

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    Wanted to go shopping while crossdressed with my Mother, However since we lived in a smaller town she was afraid we would run into someone we knew. Then one weekend we had to go to...
    Stephaniegirl226 Stephaniegirl226 36-40, M 7 Responses 6 days ago

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    Last night I was wearing my sisters clothes I had on her blue bra with matching getting on silky pantyhose black mini skirt pink crop top and 5 icnh pink heels on and I went to the...
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 2 Responses Aug 31

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    Looking For Light Friendly Chat, Or To Lend An Ear. Hey girls! I'm a young adult, bigendered and part time cross dresser. Just extending my hand to other like minded ladies who are...
    ViewtifulMe ViewtifulMe 26-30, T Sep 3

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    i keep passing over this experience as i feel embarrassed or maybe ashamed that this is even a part of me. i was good at hiding this side of me from the time i was seven years old...
    trailsonrails trailsonrails 51-55, M 2 Responses Sep 18

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    I can't stand my sister. She is a selfish, rude and abusive cow. We had a row this week as I am starting to get stronger and fight against people who try to bully me. She insults...
    firecracker1 firecracker1 26-30, F 4 days ago

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    So here it is, I am Proud to be a Bangalorean and proud to be a Cross dresser in this City. I am as normal as most Men, I work for an MNC , Drive a car in the mad Bangalore traffic...
    laaquila laaquila 31-35, M 1 Response Aug 30

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    Hi. I'm new to this site so is thought I would post! I'm 25 and in a committed relationship with a woman. I consider myself bisexual and have had encounters with both genders...
    Nikki1988x Nikki1988x 22-25, T 7 Responses Aug 31

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    i was staying the weekend with my ( unbiological ) sister. my parents give her permission if i was ever bad that she could spanked me. i never thought she would but she did . she...
    ladybearcrazygirl ladybearcrazygirl 13-15, F 1 Response Aug 31

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    I would really like to have a crossdresser friend to spend girl time with, but I am about to move out of the country soon. I don't want to start a friendship with someone local...
    Freja14 Freja14 31-35, T 1 Response Sep 5

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    My sister's boyfriend is a big kid. He and I have never really seen eye to eye. We've had several arguments and it tends to affect my relationship with my older sister. He once...
    endlessxriker endlessxriker 13-15, F 1 Response Sep 19

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    I have a gay friend that I think I can seduce if I wanted, but I asked him if he would be alright with it and he said yes, soon after that I felt huge regret and we never did it...
    fizzy711 fizzy711 13-15, M 2 Responses Sep 21

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    Well I finally did it, I told a female friend who I have been very open with about a lot of things. I sent her a picture of me all dressed saying "this is how bored I am tonight...
    Cdpantygurl Cdpantygurl 26-30, T 2 Responses Sep 1

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    Tonight both y parents went away so i had the house all to myself. I absolutely love going to the beach all dressed up so tonight was my big night to do it. About a week ago on my...
    CDcarly CDcarly 22-25, M Sep 12

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    I love my sister, I really do. I've done so many things for her. I wasn't the best big sister.. We were so young, I've spent so many years desperately trying to make up for by...
    krissybyul krissybyul 18-21 Sep 18

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    I am a crossdresser! I also love anal play x
    SluttyCP SluttyCP 18-21, M 2 Responses Aug 30

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    Hi guys. I'm a 25 year old guy and new to crossdressing. I only do this in private and no one knows. I live with my girlfriend and she does not know. Is anyone in a Similar...
    Nikki1988x Nikki1988x 22-25, T 4 Responses Aug 31

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    Very recently my gf and I were over in Bangkok and shopping we found a store where they were selling shoes in my size and oddly enough my gf told me to try them on and if I liked...
    SophieSeal SophieSeal 26-30, T Sep 2

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    any ladies or other crossdressers please message me!
    Gmailol Gmailol 26-30, M 6 Responses Sep 2

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    hey babes, if you ever want to talk to another crossdresser, just message/add me and ill add you back.
    Gmailol Gmailol 26-30, M 6 Responses Sep 2

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 1 Response Sep 3

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M Sep 3

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 4 Responses Sep 3

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 2 Responses Sep 3

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    Would this be the right group for this the only thing I wear is high heels and flats would this be considered crossdressing or not here is my collection
    Disturbedheels Disturbedheels 26-30, M 4 Responses Sep 5

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    This is a contination of my last two entries .... So my sister finally decided to talk to me last night, she explained to me how awkward it made her feel and I told her more about...
    HannatheBanana93 HannatheBanana93 18-21, F 5 Responses Sep 6

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    I lost my sister when I was 12. She was 24. My mother's daughter from a previous marriage. Prior to this, the only experience I had with a death in the family was when my grandma...
    SirenaVonLee SirenaVonLee 36-40, F 2 Responses Sep 8

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    I was in a fight with some guy and he slapped my lil sister an I told him that disrespect me idgaf but don't ******* touch my sister your lucky to still have that hand ******* and...
    PANDASAREAWESOME67 PANDASAREAWESOME67 13-15, M 2 Responses Sep 8

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    And I like to CROSSDRESSING a LOTE ONLY
    Nicholasdlf Nicholasdlf 13-15, T 1 Response Sep 8

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    I love crossdressing the feel of a sexy bra and thong are the best and sexy mini skirt
    harley80cu harley80cu 41-45, M 2 Responses Sep 11

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