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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 234 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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    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 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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    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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    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 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 14 Responses Jun 28, 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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    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 3 Responses Dec 26, 2013

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    Related Experiences

    When I was a kid, at around Halloween time, my older sister took me into her room and shut the door. She sat me down and told me to close my eyes and open my mouth. I complied...
    shredhead5 shredhead5 22-25, M 6 Responses Jul 21

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    I was at my sisters, we have always been closse. We were shopping at the mall and she decided to have nails done so we found a nail shop and she told the lady what she wanted and...
    pmgurl pmgurl 51-55 Jul 20

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 3 Responses 4 days ago

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 1 Response 4 days ago

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    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 1 Response 4 days ago

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    Work in Progress Hello, I'm new to the Experience Project so please do forgive me if I do something wrong or break a rule, it is not my intention. I'm a recent college graduate...
    CupcakeVenom CupcakeVenom 22-25, F 1 Response 4 days ago

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    Today I went over to my friends house. He has a really hot sister who's only one year younger than us. She's best friends with my girlfriends little sister. I wear my gf's little...
    sammixdress sammixdress 18-21, M 1 Response 2 days ago

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    I am in my early 40s and my sister is in her 50s. My sister and I had always been close, even though were do not have the same mother. I was raised in a home that "step" or "half...
    sunshinesammie sunshinesammie 41-45 1 Response Jul 9

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    When I was eleven I went to boarding school, leaving my three year old stepsister, Molly, at home. I had always been short for my age, and she had been rather tall but she was 3 so...
    betsy92 betsy92 18-21, F 1 Response Jul 13

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    I am 18 and a crossdresser I love the appearance of being a girl I put on bras and panties and get some of my sisters skinny jeans and put on a tight shirt and get my moms heels...
    Jlmendez15 Jlmendez15 18-21, M 2 Responses Jul 17

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    When I say annoying, I mean that she says and does things that makes me think "wtf? you really think thats funny?" or or "why would you even say/do that?" Shes a good sister, she...
    JosephMichaelSmith JosephMichaelSmith 18-21, M Jul 10

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    So I honestly just have to get all of this off of my chest because lately I've had way too much anger inside of me. So my girlfriend has 5 other siblings, two of which happen to be...
    lezbihonest18 lezbihonest18 18-21, F Jul 12

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    I never knew about my sister until I was 12, my mom and dad have her up 4 adoption when she was born, nobody told me anything about her, I didn't even know she existed until one...
    Kirakat14 Kirakat14 13-15, F Jul 7

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    Today my mum was at work and my brother and sister were asleep (for the whole day) so i decided to go through my mums cloths and i found the most beautiful see through silk dress...
    conankoller conankoller 22-25, M 4 Responses Jul 13

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    Not so big a Secret as it once was . . . As a child and young teen, my mom and sister knew I liked to wear panties. They also knew I had a nightie but never saw me wear it. My best...
    AmberFountaine AmberFountaine 66-70, M 2 Responses Jul 19

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    I really feel like I was meant to be a female. I even have a twin sister. I just had my 40th birthday. I have always been pretty healthy except for enlarged breast and smaller than...
    RontoRhonda RontoRhonda 36-40, T 2 Responses 1 day ago

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    I've known my ex for 15 years, her older brother for just as long. He was my best friend, we grew up together, and we were brothers. 8 Years ago, he was killed in Iraq, and over...
    bigbluecolonel bigbluecolonel 26-30, M Jul 16

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    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response Jul 19

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    It's been a little more than a year since I married my husband and I am fed up with his family, especially his sister. I live with my in laws, my sister in law, her husband, and...
    destinii3 destinii3 26-30, F 1 Response a week ago

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    My sister blames me for everything!! I don't know what the **** her problem is!! She bought a pack off hair bands and she gave me one to have! I lost it the day she gave it to me...
    sweetlove2014 sweetlove2014 16-17, F a week ago

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    HOW i told my parents and the results if u have not told ur parents and are thinking bout it read this NOW!!!!!!!!!!!!!!!!!!!!!so this is what happened i had written a note and...
    zoey764 zoey764 18-21 6 Responses Jul 19

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    Hi my name is ben I, live in swansea in wales, and im 17. I have long had fantasies about crossdressing, I would love to meet people on here to explore this aspect of my...
    swansea21 swansea21 18-21, M 2 days ago

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    Yesterday I got out of the shower and put on a white push-up T-shirt bra, my short shorts, a white "Wife Beater" style T-shirt, sandals, strawberry blonde wig and headed for the...
    davis36a davis36a 61-65 2 Responses 4 days ago

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    When my lesbian bi sister is horny she uses a stapon on me while i wear girls clothes and a wig
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    Tonight I went over to my girlfriend's house. Her step dad was at work and luckily her mom had to leave unexpectedly. She already had an outfit ready for me to put on. A black...
    sammixdress sammixdress 18-21, M Jul 8

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    When I was about 16 I found my Mom's red lipstick and decided to put it on, thought I would only leave it on for a few min. I had it on and was doing some things in my room when a...
    pmgurl pmgurl 51-55 Jul 9

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    I have been cross dressing ever since I was 9 years old I guess curiosity got to me and I tried on my sisters panties and her pjs I'm now 18 and Every time I try to stop I can't...
    DeenaMLuv DeenaMLuv 18-21, M 8 Responses Jul 18

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    I was at my sisters house at the time and I forgot to take off my green with pink dotted thong and she saw it over my jeans waist and she took all my underwear away and said if I...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 2 Responses 3 days ago

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    This was a very close call by seconds. I remember one night that my sister was out with friends till really late. It was my chance to raid her dresser. I would frequently make...
    double09 double09 22-25, M 5 hrs ago

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    well, yeah. basically, I have struggled with the crossdressing thing for some years. I don't go full out, makeup and dress out in public, I'm not that into it. Mainly just the...
    bigmacintosh22 bigmacintosh22 22-25, M 2 Responses Jul 10

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    ok, so im straight and went to a gay bar in madison hoping to meet some crossdressers but nobody was there. Well no crossdressers. I was so looking forward to some good advise...
    josephine39dd josephine39dd 26-30, T 2 Responses Jul 12

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    Finally! I had a chance to get into something "more comfortable" last night for a few hours. God, how I miss crossdressing if I have not done it in a few weeks (or more...
    chantelletv2 chantelletv2 41-45, T 4 Responses Jul 15

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    Well I do adore ladies who like crossdressers, but that's like, not the point. What I wanna say is - I'm a mtf trans (15) myself and I'd luv a bf who crossdresses, he may even...
    LindavdB LindavdB 13-15, T 5 Responses Jul 16

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    Hi i am a female still in middle school and i want to crossdress.But how can i hide it? i mean from my elders and maybe classmates...but anyways it would not be hard for me to fit...
    crosdreser123 crosdreser123 18-21, F 1 Response a week ago

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    i adore crossdressers so much!!! you all look so good. i have no idea why but im just so attracted to crossdressers. a bunch of cuties.
    sutsuki sutsuki 13-15, F 1 Response 3 days ago

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    Are there any women who respect male crossdressers? If so, I would like to hear from you and talk to you. I would also like to hear from women who don't and talk to you as well...
    closetedcd60 closetedcd60 56-60, M 1 Response 1 day ago

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    I was caught by my Mom it was when I was about 8 we were having some friends over for a party. I snuck off and found my Mom's high heels and put them on and was admiring myself in...
    pmgurl pmgurl 51-55 4 Responses Jul 9

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