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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 228 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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    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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    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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    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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    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 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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    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

    When I was younger eight or nine my sister and I would play dress-up I would get to wear her panties an slip and one of her skirts and cute top. As I got older we would dress...
    jenna98jenna jenna98jenna 18-21, T 6 hrs ago

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    told my mom I crossdress today huge weight lifted of my chest!!
    russellbg russellbg 13-15, M 3 Responses 9 hrs ago

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    Ok this is not my fault . We r in 9 grade and my friend has a twin . They were born in a hour they told me but but a round midnight so he's one day older then her. Ok we'll any...
    BeachJosh15 BeachJosh15 13-15, M 3 hrs ago

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    My first time ever going out in public crossdresser. I was with my sister's friend, Tori who knew about my dressing before my sister and mom did. I had asked Tori for her phone...
    CDcarly CDcarly 22-25, T 4 Responses May 17

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    I enjoy crossdressing only at home. I wish I could find a female that was also into this.
    leebeonajetski leebeonajetski 26-30, M 6 hrs ago

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    Find Crossdressing stories & Pictures www.TwistBox.inStory: NeerajaPart 1Part 2Part 3Part 4Story: Raj Turns RashmiPart 1Part2Story:Beauty ContestStory: Wife of ThomasStory: A walk...
    mounicacdcd mounicacdcd 36-40, F May 5

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    The one time I was ever caught crossdressing was by my grandmother! I was in my sisters room wearing my favorite bra and panties when I heard someone reach the top of the stairs...
    MelissaCDr MelissaCDr 18-21, T 3 Responses 6 days ago

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    The one time I was ever caught crossdressing was by my grandmother! I was in my sisters room wearing my favorite bra and panties when I heard someone reach the top of the stairs...
    MelissaCDr MelissaCDr 18-21, T 4 Responses 6 days ago

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    Its hard for me to remember exactly what started it, but at a very young age I became fascinated with girls shoes. It could have started when in grade school and the girls I used...
    jamie50 jamie50 51-55 4 Responses May 23

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    I am just a closet Crossdressers, meaning I don't really do the make up because I normally have an hour before my parents get home. I wear my sister's dress or heels... Or any of...
    Crossdress4life Crossdress4life 18-21, M 1 Response May 11

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    i am a crossdresser. i like wearing female clothes,makeup,jewellery... i wear my moms saree, petticoat, nighty as i dont have a sister ..am really feminine and i like doing...
    Anjanacd Anjanacd 22-25, M May 24

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    Find Crossdressing stories & Pictures www.TwistBox.inStory: NeerajaPart 1Part 2Part 3Part 4Story: Raj Turns RashmiPart 1Part2Story:Beauty ContestStory: Wife of ThomasStory: A walk...
    mounicacdcd mounicacdcd 36-40, F May 5

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    Find Crossdressing stories & Pictures www.TwistBox.inStory: NeerajaPart 1Part 2Part 3Part 4Story: Raj Turns RashmiPart 1Part2Story:Beauty ContestStory: Wife of ThomasStory: A walk...
    mounicacdcd mounicacdcd 36-40, F May 5

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    Find Crossdressing stories & Pictures www.TwistBox.in Story: Neeraja Part 1 Part 2 Part 3 Part 4 Story: Raj Turns Rashmi Part 1 Part2 Story:Beauty Contest Story: Wife of...
    mounicacdcd mounicacdcd 36-40, F 1 Response May 5

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    I think it is entirely logical that as one's burgeoning sexuality begins to express itself, that the normal desire to see -- and learn about -- a body other than our own would...
    sttos sttos 56-60, M 1 Response 9 hrs ago

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    i told my family three years ago i was a crossdresser. resently told a coworker and she wanted to see mee dress up. i gave here a fashin show over the phone. she said i looked nice...
    eddiepeasley eddiepeasley 41-45, M 1 Response May 6

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    Sister is the best friend in the world
    Ramisan Ramisan 26-30, M 14 hrs ago

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    My entire life I have enjoyed wearing girls clothes, it all started when my sister would dress me up in her clothes it started when I was 7 and continued until I was 10, then when...
    ArejayakaRegina ArejayakaRegina 22-25 2 Responses May 15

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    When I was 13 my big sister's friend would stay over at our house every so often and when ever they went or when they were sleeping I would seek into my sisters room and take some...
    ArejayakaRegina ArejayakaRegina 22-25 4 Responses May 18

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    I have been crossdressing for many years. I consider it to be a part of who I am. It started with a girlfriend years ago, who convinced me to dress as a cheerleader for Halloween...
    KaseyLeggs KaseyLeggs 36-40, M 13 Responses May 12

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    Basically this is going to be a short story of when i tried to come out to my mum last year... i wrote her a note/ letter and sat beside her as she read it, because i knew i...
    Sarah147 Sarah147 18-21 10 Responses May 14

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    I'm out of town for the next couple days and since I don't know anyone here really, I figured I'd go to the mall and crossdress :] I wore some navy blue short shorts, a T shirt...
    WalterStuart22 WalterStuart22 18-21, M May 21

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    Crossdressing? Is a relative word. For me I the meaning chances last year, I was teaching borne male. So growing up I and would wear girls or women's clothing I thought I was...
    DawnR59 DawnR59 51-55, T 5 Responses May 20

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    I hey guy this is my frist story..I began crossdressing when I was 16 I was just cerus of what it would feel like to were women's nylons and bra turns out I liked it then it lead...
    buggy6395 buggy6395 36-40 5 Responses 6 days ago

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    My first experience was in my first foster home. Jodi was 19 I was 10. The room smelled ok, just like her perfume & her with perfume. those of us that started cross dressing know...
    chaztrisexualnow chaztrisexualnow 46-50, M 4 Responses May 3

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    one night when I was 11 it was like any other night but I couldn't my sleep. I saw a pair of panties on my sister's bed earlier that day so that night I went into her...
    crossdresser1065 crossdresser1065 13-15, M 4 Responses May 9

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    Hello all, this is just a short little story about me over the past few months and today. Over a long time there, i hated myself for dressing. then at a stage i was under dressing...
    Sarah147 Sarah147 18-21 7 Responses May 11

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    I'm just a panty and bra guy... I got started when I was being poty trained my sister she is a little older than me and I got her old panty when she out grew them and I have worn...
    onomaine onomaine 22-25, M 2 Responses May 20

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    sisters will you let your brother to be in your dress and if yes then what will u tell to your mother???
    raman000001 raman000001 13-15, M 1 Response May 21

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    Yey I've already mentioned this but I wanted to say something!!!! My family get a lot of faces whenever we talk about ages!!! Well let me explain why??? Because of the whole...
    ItsJustRebecca ItsJustRebecca 13-15, F 1 Response a week ago

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    it all started on halloween for me i have been a witch twice, woman, hooker, redneck woman,and a twin sister.I use to hate myself over it.me on the mustang that is my real hair
    Jazonx Jazonx 36-40 3 Responses 2 days ago

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    Tomorrow afternoon, my little sister will begin the biggest adventure of her life so far-- serving an LDS 1.5 year mission in Brazil. I am so proud of her for her choice to go...
    quirkygirl520 quirkygirl520 22-25, F May 6

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    I've always loved crossdressers! I've learned half my makeup tricks from them. They're gorgeous, and definitely my "crowd". I've noticed half my friends are drag queens...
    muckwitch muckwitch 18-21, F 2 Responses May 5

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