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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 225 People

    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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    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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    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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    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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    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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    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 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 2 Responses Jan 25, 2011

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    Related Experiences

    This story is a bit long but I wanted to share ny experience so I hope you enjoy. :) Normally I'm a very closed person, I like to keep to myself and not let anyone know about my...
    YouCanCallMeLucy YouCanCallMeLucy 16-17, M 21 hrs ago

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    `Hide and seek’ by JEANETTE STUDENT OK OK I will play,(me a fed up 13 year old boy looking after my little sister) there she stood with her hands on her hips, my seven year old...
    Jeanettestudent Jeanettestudent 51-55, T 1 Response Jan 15

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    This is...weird. I made this account a long time ago, but only recently came back on, because I need some tips. First off, I'm 14 years old and I crossdress. I have tried to stop...
    ImNotCreativeWithNames ImNotCreativeWithNames 13-15, M 1 Response 3 days ago

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    I got dared by my sister to dress in her clothes so she got me a a bra, thong, wig,high heel shoes and the most beautiful dress also she done my make up and I looked like a fairy...
    Manudglh96 Manudglh96 18-21, M 6 Responses Jan 7

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    I am a Househusband since last 5 years. I loved to crossdress in my childhood and was supported by my step mother. The day she came to know about my interest in crossdressing, her...
    cdhousehusband cdhousehusband 26-30, M 3 Responses Jan 4

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 4 days ago

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 12 Responses 4 days ago

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 4 days ago

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 1 Response 4 days ago

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    Hey everyone, i want to share my experience and need some advice, but i cant tell it to my friends or family since i promised to my boyfriend, so I found this site and decide to...
    DanielleMiranda DanielleMiranda 22-25, F 1 Response 4 days ago

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    So last year I shared my experience on this page about my wonderful caring, beautiful loving girlfriend whom of which I love with all of my heart and as does she. And even though...
    need4speed28 need4speed28 18-21, M 8 Responses 18 hrs ago

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    Adolescence in the early '70s, the fantastic days of pantyhose and miniskirts. Overstimulated by the beauty surrounding me, yet no girlfriend or sister. I wanted so badly to...
    barbarainside barbarainside 51-55, M 1 Response Jan 10

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    Interesting Holiday Story My wife and I were able to get out for a couple of weekends of Holiday fun recently, and had some very interesting experiences while I was dressed as...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 4

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    My wife and I were able to get out for a couple of weekends of Holiday fun recently, and had some very interesting experiences while I was dressed as Sarah. The first one was at a...
    1SarahAnn 1SarahAnn 46-50, M 4 Responses Jan 4

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    I have been caught or almost caught many, many times in my life and yesterday Jan. 9 2015 was the first time for this year. I wasn't exactly caught but nun the less an...
    silkydrawers silkydrawers 46-50 7 Responses Jan 10

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    I haven't written anything in the past few months but today is the last day before we start a new year. Let's see...it's been more than a year and seven months since I moved into...
    destinii3 destinii3 31-35, F Dec 31, 2014

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    My girlfriend has a male cross dressing friend so she told me over the phone stateing he was a really nice guy so I took the plunge & told her I to was s crossdresser but I think...
    mick69x mick69x 51-55, M 1 day ago

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    Mum was over at a friends place and my sister and I decided to stay at home. The whole day was full of blue sky's until 5:56 PM when there was a big patch of dark grey clouds...
    Delphi111 Delphi111 13-15, M Jan 2

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    when I was about 7,8 I found a half petticoat of my moms and decided to take it to my room and try it on. I pulled it up under my armpits and it was like a dress that any girl my...
    needtodo needtodo 56-60 2 Responses Jan 1

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    2014 Review 2014 was a year of firsts in my crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Jan 4

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    2014 Review 2014 was a year of firsts in my crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I...
    1SarahAnn 1SarahAnn 46-50, M Jan 4

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    2014 Review 2014 was a year of firsts in my crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I...
    1SarahAnn 1SarahAnn 46-50, M 1 Response Jan 4

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    I have only 2 that know that I regularly crossdress, my wife who has come a long way since I dropped the bomb about it and a good friend who here lately I have told him everything...
    Allyson02 Allyson02 31-35 2 Responses Dec 27, 2014

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    I crossdress. I can't help it. I'm 13, and I've tried about 3 times to stop crossdressing, and then something triggers it and the next thing I know is I'm wearing my moms panties...
    kylexdress kylexdress 13-15, M 5 Responses Jan 2

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    I have already told you how my wife has turned me into a woman, well I have been asked if I ever dressed before this experience, well the answer to this is yes, you see I had a...
    lisasecrett lisasecrett 56-60, T Jan 18

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    My older sister is amazing. She's tall, thin, beautiful, has great style, and the GREATEST PERSONALITY. She's nice to everyone and always knows the right thing to say. The only...
    ChildOfHarmony ChildOfHarmony 16-17, F Jan 1

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    That's my favorite way to get crossdressed tbh idk why I guess it's because everytime a girl teased me about it I said no and acted like I didn't want it because I didn't want my...
    ChristianCrossdresser ChristianCrossdresser 13-15, M Jan 2

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    I'd absolutely love it if I could find a crossdressing friend in Illinois, someone to talk to about crossdressing, go shopping together and dress up together! Compliment each...
    need4speed28 need4speed28 18-21, M 4 Responses Jan 4

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    I suspect that transgender and cross-dressing individuals are in the same invidious situation that gay people were several decades ago. Hopefully, prejudice against those who have...
    Ashanti Ashanti 51-55, T 1 Response Jan 6

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    I have been with my now husband for 16 yrs. In the beginning of our relationship about a month after meeting my husband's sister she came to my house with him so that she could...
    sjsmith38 sjsmith38 36-40, M 3 days ago

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    Am I the only ******* guy here? Well anyway I'm only here because of bad forced crossdressing experiences.
    Timelord47 Timelord47 18-21 Dec 29, 2014

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    Hi I'm Nikki and i love dressing up. I usually wear my sisters stuff coz she has really sexy things:)
    SissyTeenNikki SissyTeenNikki 18-21, T 1 Response Dec 31, 2014

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    So I was asked to take some pictures the other night to show off my new shoes. I have a pair of patent leather 4 inch stiletto pumps with locking ankle straps. I was told to get...
    Photogeek47 Photogeek47 26-30, M Jan 1

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    I love crossdressers they get me so hard
    maxi54321 maxi54321 18-21, M 1 Response Jan 3

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    Me and my girlfriend just moved to a new town and she ask me if I would like to go shopping with her so I said yes as I had nothing else to do. When we got to the mall she asked me...
    Manudglh96 Manudglh96 18-21, M 3 Responses Jan 6

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    I love crossdressing in private and feeling pretty/feminine, but in public I'm an average guy. I'm starting to consider expressing my feminine side in public by wearing more...
    WalterStuart22 WalterStuart22 18-21, M 5 Responses Jan 11

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    Yes, I of course currently manifest through a specifically sexed body. But when the realisation finally dawned that I am not the body and that I am in fact pure consciousness (a...
    Ashanti Ashanti 51-55, T Jan 17

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