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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 234 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response 8 hrs ago

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    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 4 Responses 1 day ago

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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 2 days ago

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    I have a sister and a half sister who are both a bit younger than me. Quinn is my real sister and one year on fathers day when our dad was in jail my mum made me go to the fathers...
    LandonS LandonS 16-17, M 11 hrs ago

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    I started crossdressing when I was around ten years old. Womens clothes just feel right on me. I liked crossdressing since the first time I wore my sisters bathing suit. It was...
    Jessica1967 Jessica1967 41-45, T 6 Responses Jun 26

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    last weekend we drove to go see my gf's sister, it was a 500 mile trip and I had fun dressing up at night in the passenger seat as my gf drove most of the night. we checked into a...
    marysclothes marysclothes 51-55, M 2 Responses 2 days ago

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    I finally told my sister about my cross dressing and she let me wear her things :-)
    Zlayer99 Zlayer99 26-30, M 8 Responses Jun 22

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    Well I can honestly say that I don't remember what was the first item I wore . I suspect that it was my moms knee highs . I was maybe 6 or 7 . As I got older , I began to explore...
    Mindi3107 Mindi3107 26-30 1 Response Jun 28

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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 1 Response 5 days ago

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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 1 Response 3 days ago

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    I love crossdressers... and why. I always saw things from the girl's body, feeling like a boy point of view. It was natural for me to wonder about the other side, if there were any...
    DarkwingGoslyn DarkwingGoslyn 31-35 1 Response Jun 28

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    I've struggled with being a crossdresser all my life, and be Christian crossdresser for the last 21 years. When I was only a crossdresser I just though I was sick and something...
    DawnR59 DawnR59 51-55, T 7 Responses Jun 30

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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 6 days ago

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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 3 days ago

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    I Crossdressed As A House Wife Ive been crossdressing for as much as 8 years. Have been a closet crossdresser ever since. A basketball coach back in college days caught me with a...
    submisst submisst 26-30, T 3 Responses Jun 22

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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...
    jmallon764 jmallon764 18-21, M 4 Responses 3 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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    Well Like all of us . I started feeling more like a girl when I was young. My sister knew and let me wear her old cloths. Mom caught me so many times but wasn't supportive. I...
    Bobbie52C Bobbie52C 51-55, T 1 Response 6 days ago

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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 7 Responses 4 days 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 1 Response 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 a week ago

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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 6 days ago

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    This morning Dakota my sisters Best friend came over to visit me she is really nice to me unlike her brother. We spent the first part of the morning giving each other manicures...
    SummerLove16 SummerLove16 16-17, F Jun 22

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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 3 Responses Jul 9

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    Hi, I've been reading stories on here for a while but today I will post one of mine. Enjoy^^ I used to try on my cousin panties and bras as we where growing up. At first it was as...
    Selena512 Selena512 22-25, F 7 Responses Jul 12

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    me and my two sisters don't get along with my sister, i got two 1 older and 1 younger i'm the second oldest out of four of us. me and my older sister never get along anymore...
    iloveyonannan iloveyonannan 16-17, F Jun 27

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    *Killed **I WOULD NOT RECOMMEND THIS AS A METHOD OF ANIMAL EUTHANASIA** Today at 12:43 PM my sister's pet rat died. He was very old, had a large tumor, trouble moving around, and...
    WolfsongStorm WolfsongStorm 16-17, F 1 Response Jun 30

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