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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 225 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 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 12 Responses Jun 28, 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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    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 10 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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    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

    I have only 2 that know that I regularly crossdress, my wife who has come a long way since I dropped the bomb about it and a good friend who here lately I have told him everything...
    Allyson02 Allyson02 31-35 1 Response 22 hrs ago

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    I kissed my sister .. After she had died .. I was her best freind she always told me that to me she was more than that . A person I admired and doted on . My only sibling . A bond...
    Homejames Homejames 51-55, M 1 Response 22 hrs ago

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    My husband always likes me to cross dress as a man and he cross dresses as woman.Though sometimes embarrassing,sometimes it is relaxing after week's hectic work schedules.It all...
    ankletfeet ankletfeet 16-17, F Dec 1

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    I was potty trained in my sisters panties and loved them. We could not afford reg boys underwear all the time so I always got my sisters. I loved whin she switched to thongs. The...
    onomaine onomaine 22-25, M Dec 15

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    Thinking about coming out to my sister. Over the past couple of months, I've realized that I'm a crossdresser. I've already debated for a while about coming out to my family and...
    Cmoor007 Cmoor007 22-25, M 3 Responses Dec 7

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    Hi, im 15 years old and have been lightly crossdressing for the past 2 years. I usual cd when i have to watch friends house while theyre on vacation so i use their moms and sisters...
    bfetishes bfetishes 22-25 Dec 4

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    My future sister-in-law stayed with us one summer. I would have been about 13 or 14. Once I was home alone and, for some unknown reason, found myself drawn to her room. I went...
    Niqqi Niqqi 46-50, M 3 Responses Dec 13

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    I spent the whole day crossdressed in public today. Well not the whole day since I didn't leave the house till 1:30. I started out by going and playing bingo, which I do every...
    Michelle1976 Michelle1976 36-40, T 2 Responses 5 days ago

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    I a guy who loves to wears girls clothes, I would love it I a girl adopted me as their special sister, we could dress up together, and go shopping together, and all that fun stuff...
    LexyCD LexyCD 18-21, M 5 hrs ago

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    I don't even know where to begin with this woman!!! This is how irritated she has me! She thinks and makes my husband think she is such a great nice person because she is very...
    gemini61289 gemini61289 22-25, F 2 hrs ago

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    Been dressing since age 13 at 14 was found out by a friend he told me I knew you were gay because all the girls like you I told him we play dress up and I want you to be my...
    lvrofhose lvrofhose 56-60, M 1 Response Dec 3

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    My boyfriend of over a year came out and told me he wants to Crossdress. I love him more than I ever thought I could love someone. The idea of it is new to me so I'm not sure what...
    tallchick003 tallchick003 22-25, F 1 Response Dec 19

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    I was hooked by a pair of pink panties with ruffles along the waistband and the leg holes. They were laying there, spread out like on display, on the corner of the older sister's...
    cdsubalice cdsubalice 56-60, M 4 Responses Nov 30

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    The 1st 2 pairs of underwear I got and was potty trained in come from my sister. I fell in love with comfyness of them. later on my mom got me more now they are all I wear. I love...
    onomaine onomaine 22-25, M 1 Response Dec 15

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    God doesn't make mistakes. I was just reading some comments to another Christian Crossdresser story, and came across these words. In the comments I was reading just now they were...
    AzabethTV AzabethTV 51-55, T 1 Response Dec 11

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    I told my girlfriend that I would like to crossdresser, explained her all about it and especially that I am not gay and it's not that I like to dress everyday. Now everytime I try...
    JohnnyGpoint JohnnyGpoint 36-40, M 1 Response Dec 16

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    Im a 18 year old boy who has just finished high school. Ive always loved the idea of wearing girly clothes as they are often really cute and nice.. im always checking girls out but...
    Giles2142 Giles2142 16-17, M 1 Response 3 days ago

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    When i Was 13 And My Sister Was 15 I Was In My Room ************ Around 11Pm ( My Parent's Where Sleeping ) Then My Sister Came Inside My Room To ask Me Something Then She Caught...
    LoveThatGuy LoveThatGuy 18-21, M 4 days ago

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    New to ep been crossdressing since 13 now 56 love to crossdress wearing hose,skirts,sweaters,panties, heels, makeup,wigs,body shapers,and bras. Love sexy lingerie had sales ladies...
    lvrofhose lvrofhose 56-60, M Dec 2

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    I know i haven't posted a picture of me in a while but tomorrow i will be able to crossdress for the whole night without anyone calling me or going into my room so i will post...
    Ruby1997 Ruby1997 18-21, T 1 Response Dec 19

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    hi, I used to crossdress a lot and I used to have a lot of pictures on this website but out of fear of being caught I deleted them all. anyway I was just wondering, does your...
    Tyrone147 Tyrone147 18-21 4 Responses a week ago

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    No idea but I've been told quite a few times that there's something about my voice, lol. Maybe it's the mixed accent...or the actual sound of my voice...no idea. But it's pretty...
    ibak12 ibak12 16-17, F 9 hrs ago

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    The actual first time I wore girls clothes was when I was 7. My family and I were away from home visiting some friends. They had all girls and very close to the same ages as us. It...
    Adam59 Adam59 56-60, M 1 Response Dec 4

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    Last Super Bowl I made a bet with a girl who I was seeing at the time named Mary who was a huge Seahawks fan. We decided that the loser had to wear what the winner decided for 1...
    wildcard23 wildcard23 22-25, M 2 Responses 3 days ago

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    hi there I got a wedding dress for a girl friend to ware for sex :) she told me that it was not for her but for me to ware she took me out in it for holoween she told me I need...
    pitsfield pitsfield 41-45, T 3 Responses Dec 6

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    I love being a crossdresser sometimes. Every time I go shopping for women's clothes, I always love trying them on at the Fitting Room. Normally I look for leggings, bra, panties...
    Pretty7Pretty Pretty7Pretty 26-30, M 2 Responses Dec 6

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    I have this desire to crossdress, but don't have clothes. I used to have a lot, but I donated them all away one day to try and get myself to stop crossdressing. I love how women...
    cranblueberries cranblueberries 26-30, M Dec 9

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    Some of the best friends I've ever had are transsexuals and crossdressers. I helped one of my past boyfriends of two years even realize he was a male. I helped him pick his male...
    AlysonBlack AlysonBlack 18-21, F 1 Response Dec 13

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    Found this website cause i was searching crossdressing stories and came across this... Im new to crossdressing.. Its fun..
    over13 over13 13-15, M 2 Responses Dec 14

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    Today one of my fantasies is starting to come true. I took my girlfriend out the other day and she had the sexiest dress on with these beige stiletto heels on, she turns me on in...
    Zoe24 Zoe24 22-25, M Dec 16

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    I have been crossdressers since my teens am now in my 40's I have accepted me as I am. If anyone has a problem with it is not my problem. I don't think I will stop crossdressing I...
    bloubulsarel bloubulsarel 41-45, M 1 Response a week ago

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    I try not to call it crossdressing. At least not until all those girls in jeans and tee shirts start calling themselves crossdressers. But yes. Yesterday was a wonderful...
    MrsJoanieBNH MrsJoanieBNH 56-60, T 7 Responses 5 days ago

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    Part 2: When i Was 14 And My Sister Was 16 ( It Was Summer Time ) My Parent Always Worked From 8:00Am Till 4:30Pm Exept Fridays. Well it Was Around 7:30Pm And Me And My Sister...
    LoveThatGuy LoveThatGuy 18-21, M 2 days ago

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    I have 4 siblings, one older brother (25), one older sister (23) I'm 19, and two younger sisters (15 and 9). The 15 year old is tougher and stronger than me and knows it. She likes...
    Draves700 Draves700 22-25, M Dec 10

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    Recently my mother in law moved in with me. It was not a planned move. She has mental problems, and other health issues, and my husband and I knew that she could not live alone...
    CCM13 CCM13 31-35, F 2 Responses Dec 12

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    I don't think I look like an angel but several people had told me that I do look like an angel.
    velvetybat velvetybat 13-15, F 1 Response 9 hrs ago

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    Left college,entered the work place. Got a seasonal position job at a resort. Worked there for 5 years before moving on, met April , 2nd year, worked together in 3rd year. She...
    lvrofhose lvrofhose 56-60, M Dec 3