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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 232 People

    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    my sister is 17 and bites me very hard and pulls my hair and bashes me with objects and gouges me with her fingernails and tries to kill me. my parents do nothing to help me...
    BrutalNoodle BrutalNoodle 16-17, F 1 Response 1 hr ago

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    I was a my friend's place and were playing in the pool with his younger sister. We may had 14 and her 12 at the time. I got into the bathroom after she went to change and the...
    Uphilthis Uphilthis 36-40, M 14 hrs ago

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    I am lookin for friends I want to keep crossdressing and get more help need people. to talk to. want to find other crossdress to hang out with dress up go shopping. out for a drink...
    Mybritt Mybritt 31-35, M 3 Responses 20 hrs ago

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    so, im a teen crossdresser (17) and iv been dressing since i was 10 or so. im so happy i can have this life and its so exciting. At this point i have a nice little collection of...
    CDArseni CDArseni 18-21, T 1 day ago

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    My sister is an idiot. I love god with all of my heart and I can't believe he created her. She fights with me everyday and gets everything that she wants. Even the stuff that I...
    hlanecki hlanecki 22-25, F 1 Response 1 day ago

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    Just now found this site, Yes I won't to Join with my special Sisters, I'm Kaydi from Prescott Az. xoxo KD.
    stoflicken stoflicken 66-70, T 1 day ago

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    She's always being mean to me. Calling me bald head and ugly and stupid. I wish that somebody in this family understood me. I literally have no one to talk to that would understand...
    LoveDimpless LoveDimpless 13-15, F 2 days ago

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    Hi all I am new to crossdressing and just started at the age off 50 when I had low testosterone but now I am on the correct medication I still love to and want to dress and act...
    Robbie0306 Robbie0306 51-55, M 5 Responses 3 days ago

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    I have recently been told that my fiance is a crossdresser/Siss (his wording). I was shocked for a moment. What shocked me more was how much it didn't bother me. I felt just as...
    cnb15 cnb15 31-35, F 4 Responses 4 days ago

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    My sister has just come in with her friends, i have no man clothes or anything in my room. She was meant to be out all night, And now theyre staying here. I could just wait until...
    crossdresser1963 crossdresser1963 22-25, M 4 days ago

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    . Its 20 to 12 in the UK, eveyrones out. My sister is out with her mates, she is sleeping there. My mum and dad are on holidays. No one else can intrude me. Probably doing an all...
    crossdresser1963 crossdresser1963 22-25, M 7 Responses 4 days ago

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    Hi guys my 2nd post I think, I have a problem, I want to be a girl and wear mini skirts and make up, I want my parents to understand me if I say to them "I want a sex change and...
    Lucy14CROSSDRSSER Lucy14CROSSDRSSER 13-15, T 2 Responses 5 days ago

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    I currently have what is called a Maximillian-that is a beard and moustache- but I have been told many times that I look like my late mother. I have quite high cheekbones and have...
    comfi comfi 51-55, M 6 days ago

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    Up until I was about 13 me and my sister would get along fairly well. We weren't perfect but we had a good relationship. In 7th grade I was diagnosed with anxiety and mild...
    Doglover231 Doglover231 26-30, F 2 Responses 6 days ago

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    I've gone out a few times crossdressed as a girl, but the other day it was my 2nd time to put myself into a public place, and actually interacted with someone.First, just some...
    kilv777 kilv777 26-30, F 5 Responses 6 days ago

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    I am disabled and when I was young money was tight. When I had no clean pyjamas sometimes my Mum put me into one of my sisters. My brother was bigger than me but my sisters were...
    comfi comfi 51-55, M 2 Responses a week ago

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    Today I took my first step to coming out as a cross dresser to my family. I have to cross dress for certain after school activities, which they know, but I've never before gone out...
    RedHeadedNinja RedHeadedNinja 13-15, F 4 Responses a week ago

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    My family was leaving for dinner and I didn't wanna go, right when they left I rushed to my sisters room and I had this all planned out. I put on a thong and sports bra. Put in...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 1 Response a week ago

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    Im a 20 year old muslim girl. Part of our culture is we have arranged marragies where the mother or father of the guy comes to the girls family and ask for her hand in marriage...
    Zozolove Zozolove 18-21, F 4 Responses a week ago

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    I was with my grandma for weekend. I went there wearing my boy clothes and under I wore, garter belt, nylons, thong, girdle and a bra. All my girl clothes u couldn't see. So my...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 1 Response a week ago

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    So Sunday I was going to tell my GF that I am a cross dresser when she came home from her trip home. When we got home from the airport she sat down I fix her a glass of wine and...
    Kamryn83 Kamryn83 31-35, M 5 Responses Jul 20

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    I Hate My MIL Experience Project: Stories about every Life Experiences Home Search Groups Stories Questions People Post 1 tarabull Me Content Removal Appeal It looks like...
    tarabull tarabull 31-35, F Jul 19

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    So, my sister got married this weekend. I received an invitation and declined to go. We haven't spoken in years and that's how I like it. She told my mother to make me go but...
    Quiettimeplease Quiettimeplease 31-35, F 1 Response Jul 18

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    So my parents caught me wearing my sister's underwear and got really mad at me and said well if that's what you want to wear then you can ask her if you can wear them. Well I...
    ryan1229 ryan1229 18-21, M 8 Responses Jul 18

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    I was 15 when I was caught by Mr. Gunderson, a neighbor who lived down the street. I'd found a summer job and got to stay home alone when everyone else went on vacation. Sixteen...
    amandatrane1 amandatrane1 51-55, T 3 Responses Jul 18

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    i know i wasnt ready for a baby. i feel that i made a resposible decision by getting an early abortion. i made the mistake of telling my sister with two kids about it. she is being...
    gofey gofey 18-21, F 1 Response Jul 17

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    Telling someone is so different every time. My family know but never mention it after I came out to them tho for awhile none called me or invited me over and I never tried to...
    amandatrane1 amandatrane1 51-55, T Jul 16

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    when I was 16 my Sister caught me wearing her panties and bra and nylons, she wasn't happy with me at all, I was very scared and didn't know what to do, She used that fact that I...
    deleted deleted 26-30 1 Response Jul 16

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    I'm 15 year old secretly stealing from my sister dresses and make up and gowns and bra and panties she has so mutch she doesn't notice I'm secretly attracted to men message me let...
    sissyboy20000 sissyboy20000 13-15, M Jul 16

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    I'm 15 year old secretly stealing from my sister dresses and make up and gowns and bra and panties she has so mutch she doesn't notice I'm secretly attracted to men message me let...
    sissyboy20000 sissyboy20000 13-15, M 1 Response Jul 16

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    I secretly wear my 18 year old sisters garment bra lingerie panties gowns dresses and make up she has so much that's she doesn't no I wear it in my room secretly I'm 15 I'm...
    sissyboy20000 sissyboy20000 13-15, M 1 Response Jul 16

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    My sister is nothing but an attention seeker. I'll start at the beginning, when I was about 12 my sister began stealing from me and my family It started with DVD's and things then...
    BlairGarnet BlairGarnet 18-21, F Jul 16

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    I'm a sister, the youngest in fact, but I feel so alone. My two eldest sisters are like peas in a pod while I'm the odd one out. They live together, work-out together, work...
    agathashelly agathashelly 26-30, F 2 Responses Jul 16

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