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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 258 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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    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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    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 5 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 11 Responses Jun 28, 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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    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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    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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    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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    Related Experiences

    One thing I have yet to do, in the 15 years I've been crossdressing, is find some one to host well I get all prettied up. Fix my makeup, throw a pretty wig on, and throw a sexy...
    Jasminesissy Jasminesissy 26-30, M 6 hrs ago

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    I was 11yrs old when my Mom was telling my sister that she need to start wearing a bra. She went shopping earlier for her stuff that day. As my mother was pulling bras and new...
    PinkblueCD PinkblueCD 41-45, M 1 day ago

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    I was about 10 or so. I always had this fascination with panties. The first pair I tried on was from my aunt. But the girly rush I got from wearing em kept me hooked. I would...
    Jasminesissy Jasminesissy 26-30, M 1 day ago

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    I hate fake people.. My fiance's sister is fake as hell and I believe she's mentally ill. My fiance suffers from bipolar and goes crazy every now and then. Her starter had zero to...
    nuttiebud nuttiebud 36-40, F 1 Response 1 day ago

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    When I was little my mom was a nurse. She would leave and I would get sad, she would tell me to go get in my step dad's bed so I would go back to sleep, that was okay for a while...
    42chwgca 42chwgca 16-17, F 1 Response 4 days ago

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    it all started with my older sisters cloths... we use to have a lot of teen age baysitters when we were young and my sister always wanted to play dress up. I think the baby sitter...
    crossdresserfun crossdresserfun 22-25, T 2 Responses Feb 5

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    I am going to try and target 3 caught crossdressing stories by the weekend Here's story no1 they do come in parts. The bridesmaids story.... Hi my name Eric I am 17 and this is...
    EvaMarie1406 EvaMarie1406 22-25, M 3 Responses Feb 5

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    So I had always been dressing whenever my parents would leave and run errands. So every time they left the house I would race into my moms room and immediately throw on a dress...
    lcd6993 lcd6993 22-25 5 Responses Feb 4

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    Well, I wasn't really caught but almost was close enough. I was in my sister's room when no one was home. I started to parade around in her bra and panties when I heard the front...
    ReneeTalley ReneeTalley 56-60, M 2 Responses Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 1 Response Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 1 Response Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M Feb 3

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    This is somewhat of a different way of getting caught. I buy my cosmetics at my local drug store. It is nice because they have a self checkout line, and for a closet crossdresser...
    andreatcial andreatcial 26-30, M 3 Responses Jan 28

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    Crossdressers have always facinated me. So I enjoyed seekng them out in chat rooms hoping to find one showing off on a webcam. One particular night the chat room was dead. No...
    chrissyk48 chrissyk48 46-50, M 6 Responses Jan 27

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