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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 234 People

    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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    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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    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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    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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    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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    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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    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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    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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    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 5 Responses a week ago

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    I want to cry right now I've taken up drinking because it numbs the pain of my self disgust I'm drunk right now and want to kill myself I hate myself because I crossdress I thought...
    JulieCakes JulieCakes 13-15, M 3 Responses Aug 24

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    I'm sure everyone says this about their sister, but I am serious.. She is a spawn from hell, she's not even fun. She's 20 years old, was homeschooled like me, doesn't have a job...
    Bflyboo14 Bflyboo14 13-15, F 2 Responses 8 hrs ago

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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 a week ago

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    My very first crossdressing experience was when I was about 6 or 7 my sister was fooling around with a camera and I love the spotlight so I said I would do anything to get on it so...
    Tigerbentz Tigerbentz 16-17, M 1 Response Aug 25

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    Yesterday started out like most days. I get up in the morning and take a number of my nightgowns, negligee sets out of my closet and put each one on until I find the one I want to...
    silkydrawers silkydrawers 46-50 4 Responses Aug 20

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    I have just told my girlfriend that i like to crossdress and would like some advice from a girl
    JohnnyGpoint JohnnyGpoint 36-40, M 2 Responses Aug 29

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    I have just told my girlfriend that i like to crossdress and would like some advice from a girl
    JohnnyGpoint JohnnyGpoint 36-40, M Aug 29

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    I have just told my girlfriend that i like to crossdress and would like some advice from a girl
    JohnnyGpoint JohnnyGpoint 36-40, M Aug 29

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    I don't consider myself a crossdresser. I do wear a lot of things that women wear... nail polish, panties, nylons, skirts, heels, sandals, sneakers, hiking boots, shorts, jeans...
    steve66oh steve66oh 46-50, M 4 Responses Aug 23

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    Great time last night.Seemed to take ages getting ready and a big thanks to my sister who done my hair and make up.I met a man yesterday who i went for a coffee with and he asked...
    girlynicole girlynicole 36-40, F 12 Responses Aug 21

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    I have a little sister who is developmentally disabled, she met a guy and got pregnant. She thinks that this guy will stay with her and help her. He has three domestic violence...
    keiraames keiraames 26-30, F Aug 25

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    When I was almost 14 my Mom dressed me as Little Bo Peep for an Easter Parade. I won the prize! My mom was an outstanding seamstress and rarely used patterns. She could create a...
    patty1650 patty1650 56-60, M 1 Response Aug 27

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    Yesterday the sister in law came around 2 pick summit up she left so I went and put my leggings on and knew nothing more then she came bk in 2 get her glasses I just sat and...
    24chris24 24chris24 22-25, M 1 Response Aug 29

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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, M 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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    Well, i've never been caught andi just want to tell you what I have. First I have no sisters only brothers. I only have 1 girl cousin and one day I hope to ask her to help me get...
    WhiteKyrem12 WhiteKyrem12 13-15, M 3 Responses 5 days ago

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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 1 Response 2 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 22 hrs ago

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    My friend came over to my house and he went to my room I forgot to put my pink thong away and he asked if I wear it I told him yes and he asked if I fully dressed I once again said...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 5 Responses Aug 23

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    I was caught by my mum a few months ago. I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around...
    tomcd95 tomcd95 18-21 6 Responses Aug 29

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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 22-25, 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 a week ago

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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 2 days ago

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    i have always wanted to be a crossdresser but dont wanna be gay or ewt what should i do
    ilovestorys1963 ilovestorys1963 13-15 1 Response Aug 20

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses Aug 21

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    im 13, the other day i found out i have an older sister, she was put up for adoption 9 years before my birth. i was really upset at my mum but, my mum was only 14 and she had been...
    scribble1 scribble1 13-15, F Aug 22

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 8 Responses Aug 22

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    I don't consider myself a crossdresser. I do wear a lot of things that women wear... nail polish, panties, nylons, skirts, heels, sandals, sneakers, hiking boots, shorts, jeans...
    steve66oh steve66oh 46-50, M 2 Responses Aug 23

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    I've always wanted to find someone to love who's a Crossdresser. But more than just sex a real relationship. Where I'm from it's very hard to impossible to meet anyone.
    skijunkie10 skijunkie10 22-25, M Aug 24

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    If just about any girl can help me crossdress it would be awesome
    Tigerbentz Tigerbentz 16-17, M 2 Responses Aug 25

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    my wife of thirty two years left me bcause i crossdress sah as known since are relation ship started
    victoriasize6 victoriasize6 51-55, T 12 Responses Aug 25

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    I would love a crossdresser pen pal from New York i'm from Ireland
    jodiK33 jodiK33 41-45, M Aug 25

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