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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 228 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 16-17, T 2 Responses Nov 11, 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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    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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    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 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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    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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    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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    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 first crossdressing was when I visited my sister at her house she is 25 years old and I was 13 years old today she was out so I was by myself I got bored so I went up to her...
    cutewolf197 cutewolf197 16-17, M 2 days ago

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    It started when I was about 11 years old and she was 6. It had always been difficult with my sister bc she always needed attention and so she was my parents favourite kid, also...
    k2611 k2611 18-21, F 2 hrs ago

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    Soo i had this fantasy: I had moved schools and for a school assignment i was partnered up with a guy called James. James was a kid that was shy and doesn't have too many friends...
    Stephsiszy Stephsiszy 22-25, T 4 Responses 1 day ago

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    I am extremely lucky to have the group of friends that I have! Crossdressing has been a part of me since I was a little tyke, and I've kept it a secret all this time. I finally...
    kins101 kins101 26-30, M 2 Responses 13 hrs ago

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    I am a 17 year old cross dresser, it all started when I was 13. The way it all started was when I was home alone for a day and I got bored of video games. While I turned off my...
    Cristyy274 Cristyy274 22-25, M 8 Responses Mar 8

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    Part3 by ForceTied18 Slowly I turned to face her. Actually, that wasn't entirely true. I was so ashamed and scared that I choose to stare down at the ground instead. Suddenly a...
    ForcedTied18 ForcedTied18 18-21, M 1 Response Mar 11

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    I started wearing my sisters clothes when I was a young teen, panties bras at first, then it got to be I would put on her skirts, and tops, and I felt so feminine in them feeling...
    jennylace1 jennylace1 51-55, M Mar 16

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    Took some of my sisters clothes and took a pic before she noticed! I don't really like the picture itself but the clothes felt so good!
    TrulyAGirl TrulyAGirl 13-15, T 4 Responses Mar 19

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    This is a experience about the first time I cross-dressed. I typed it out to tell a friend on here so I might aswell post it with a tiny bit more detail... When I was very young...
    TakeAPicture TakeAPicture 16-17, T 3 Responses 2 days ago

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    Anyone wanna talk abot crossdress or help me crossdress? ;)
    Nick150 Nick150 13-15, M 2 Responses Mar 12

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    The first time I cross dressed I was super young like probably 5years old it just felt right im 22 now and still do it when I'm home alone im non binary im not gay I could possibly...
    Horseofdiffcolor Horseofdiffcolor 22-25, T 3 Responses Mar 15

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    I don't feel welcome in the crossdress img community as I'm a female who dresses as a male. I don't know if it's just me personally or because we can't relate being to different...
    miskia0917 miskia0917 18-21, F 4 Responses Mar 19

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    Recently I started feeling more and more like moving forward with the things that make me happy and excites me such as piercing my ears or buying some new stilettos. But The truth...
    Danairis Danairis 46-50, T 1 Response Mar 22

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    Im a 21 year old and I want to meet and talk to crossdressers! I was in to crossdressing myself when I was younger but got out of it. Ive always just had an attraction to men in...
    nick191 nick191 18-21, M 1 Response Mar 22

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    On weekends, unless I am going out on the town, I typically wear women's jeans, or capri pants to run my errands and do housework. I always wear makeup and try to look and be as...
    dianecarr dianecarr 61-65, T 4 Responses 2 days ago

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    Bidding adieu to my sister after her marriage was the memorable moment of my life. I never told neither did, I showed it to her, but she was the person who understood me. I love my...
    Lakshay1993 Lakshay1993 18-21, M 1 Response Mar 4

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    I have two sisters now.My oldest sister Cecilia was out of the house as I was growing up, so It was pretty much just me and my parents. But I was so surprised and excited when my...
    justerika justerika 26-30, F Mar 23

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    When I was young I was overweight my elder sisters are always praised for their looks and now it's the opposite since I've lost the weight and my elder sister one of them gained a...
    EnvysEnemy EnvysEnemy 22-25, F 2 Responses 2 days ago

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    omg where to start lol she tells us how to spend money and manage our time together. she lives an hour away but yet we see her once or twice a week my parents live around the...
    ashleynichole25 ashleynichole25 22-25, F Mar 11

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    So today, I was doing homework, my sister would not leave me alone because she wanted to play a game with me. I told her to play with my little brother or by herself because I need...
    Jgummy123 Jgummy123 13-15, F 4 Responses Mar 11

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    I was almost caught. I was wearing all girl clothes and went for a drive. Stopped at a clothing store and looked around. There was another clothing store a few doors down so I...
    mat2Robin43 mat2Robin43 51-55, M 8 Responses Mar 7

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    I too lost my sister to cancer, it has been one week and a day, still seems unreal. Her name was Melinda and she was only 55. she had aml leukemia. She was diagnosed in September...
    karensunfire00 karensunfire00 46-50, F Mar 11

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    Jumping Off A Cliff. This is what I have always told my sister. "I want to jump off a cliff!" Every time I am sad or feeling nasty, I say that. At first, my sister would just...
    mareliberum mareliberum 26-30 1 Response Mar 13

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    Today my sister and I were discussing relationships. Lately we have been getting along really well, I'm always trying to make her laugh. She is mean to me quite a bit, but I try to...
    thegalaxychild thegalaxychild 16-17, F 1 Response Mar 19

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    Every time I see some panties, a skirt, some heels I feel an urge to try them on. I've only told one person and I feel like my family will disown me
    deleted deleted 26-30 3 Responses Mar 21

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    When I was about six, Dad enjoyed watching The Benny Hill Show. The show always had beautiful girls in beautiful lingerie chasing him. I really enjoyed that part of the programme...
    torixdresser torixdresser 36-40, T 6 Responses Mar 4

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    If you like crossdressers, please come chat with me I want to know all about it and you.
    69hotstuff69 69hotstuff69 22-25, M 2 Responses Mar 5

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    Comment if you would transform me from a boy to a girl makeup and everything I don't care if I could never take the wig off I just want to be crossdressed by Simone else
    flamered1248 flamered1248 18-21, T Mar 5

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    i am visiting the crossdressing festival 2015 at Chamayavilakku (Kollam CD Festival) kerla . thos who are visiting same place mail me at ruchacdmumbai@gmail.com . if possible we...
    femboiindia femboiindia 31-35 1 Response Mar 6

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    I am a crossdresser just looking for someone females friends or just some ceossdressers just to talk to.
    yoshua12 yoshua12 18-21, M 2 Responses Mar 8

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    I am happy to chat with crossdressers
    crossdresser1065 crossdresser1065 13-15, M Mar 9

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    Is there any crossdressers on here who want to come over to my house today
    hannah357 hannah357 18-21, M 2 Responses Mar 9

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    I would love to meet a lady in Canada. I am sissy baby crossdresser who love a mommy to take me in as her daughter.
    RachelHill RachelHill 26-30 1 Response Mar 9

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