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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 233 People

    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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    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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    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 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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    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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    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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    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 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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    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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    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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    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

    Great time last night.Seemed to take ages getting ready and a big thanks to my sister who done my hair and make up.I met a man yesterday who i went for a coffee with and he asked...
    girlynicole girlynicole 36-40, T 9 Responses 12 hrs ago

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 5 Responses 9 hrs ago

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    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 16-17, M 4 Responses Jul 31

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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 6 Responses Jul 21

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    Today something weird happend to me i am 30 years old and my sisters are 26 and 24 years old. They where trying dresses because they are invited to their friend wedding I was...
    Frrameh Frrameh 26-30, M 7 hrs ago

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    My sister is 2 1/2 years older than me. Long dark hair, bluish eyes,and a shy smile that hides the devil. She is beautiful and intelligent but few people realize how cunning and...
    SolomonSaul SolomonSaul 16-17, M 41 mins ago

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    I've been crossdressing as far back as I could remember. My first time was when I was at a day care (I was 3 Y.O.) and there was a dress-up bin. I took out the dress, put it on...
    necxo necxo 18-21, M 1 Response Aug 8

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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 Jul 26

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    After my parents got divorced when I was ten, I was living with my Dad. He was bisexual and had a boyfriend that stayed with us. On some weekends I would stay at his boyfriends...
    Michelle1976 Michelle1976 36-40, T 4 Responses 5 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 2 Responses Jul 26

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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 2 Responses Jul 26

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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 3 Responses Jul 26

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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jul 31

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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 Jul 29

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    I swiped my first pair of panties from a friends sister when I was 9. By the time I was 11, I had collected quite a few pairs from her and my cousins. I kept them in a shoe box...
    Bobbie1952 Bobbie1952 61-65, M 4 Responses Aug 7

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    I love my sister Alyson so very much. She is special, pretty upbeat regardless of her condition with Macromastia. Sure it get's her down sometimes but I manage to find ways to...
    ChristyyS ChristyyS 22-25, F 3 Responses 7 hrs ago

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    So, I am fairly new to crossdressing (been at it for about half a year). I keep it a secret and I'm perfectly content with it staying that way. But it has always been a desire of...
    SuperCornstock SuperCornstock 16-17, M 2 Responses Aug 10

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    I was always close to my brother when we were growing up. When we grew up and moved into our own lives, I lost contact with him for a few years. Then I signed up on Facebook and we...
    Baralinel Baralinel 26-30, F 2 days ago

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    So this is a big step for me. I've never been incredibly public about my crossdressing. This is the first thing i've ever done online relative to it with any kind of public...
    EmilyRose15 EmilyRose15 16-17, T 3 Responses Aug 7

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    As a child I was the younger by almost 2 years. My father told me my sister never liked me from the time I was brought home. She used to hit me until I would finally fight back...
    irishicould irishicould 31-35, F Aug 12

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    It started when I was around 12 I had a friend that was a girl and we were playin truth or dare and she dared me to wear one of my sisters thongs for a few days and I did I love...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 3 Responses Jul 31

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    I'm a 22 year old man and I am 5-2. Now you are reading this and thinking, "he's so short, not very hard for his sister to be taller than him". Well not only do I have 3 sisters...
    Carlsoncarly Carlsoncarly 18-21, M 2 Responses Jul 31

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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 Jul 23

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    Do I think crossdressers are gay, you ask me? Are they honest, is my counter question. I know is not exactly legimate to answer a question with another question but. But this...
    gypa gypa 26-30, M 6 Responses Aug 5

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    My sad story about my sister. I am a girl; I am 16 years of age. My sister is 18. This long story is mostly about us two. Therefore, please read this carefully and help me get out...
    Miserabelle Miserabelle 16-17, F 2 Responses Aug 8

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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 Jul 23

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    I have been married for 15 years. The crossdressing came out about 8 years ago. I was really supportive and loving about it. Felt sorry for Husband that he had had to hide it all...
    LadyLana39 LadyLana39 51-55, F 5 Responses Aug 1

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    Yesterday started out like most days. I get up in the morning and take a number of my nightgowns, negligee sets out of my closet and put each one on until I find the one I want to...
    silkydrawers silkydrawers 46-50 1 Response 1 day ago

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    She's just perfect like ever since she was little. I don't really like to admit it, but yes I am jealous of her. She's good at everything: studying, sports, making polymer clay...
    Weirdestone Weirdestone 16-17, F 1 Response Aug 12

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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 Jul 28

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    My sister and I used to share a room together when we were younger. At the time, I was 7 and she was 11. We were always close in a way but it changed when my parents decided for us...
    fairytailmage fairytailmage 18-21 2 Responses Aug 5

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    I had joined this group and thought I should really add a story no matter how short. The above type of man can also be termed as a Transvestic Fetishist Under-dresser not simply a...
    manslip manslip 56-60, M 3 Responses Aug 7

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    Lately I've been crossdressing a lot less but, I've been having dreams where I'm crossdressing a lot more, it's been frustrating I'm trying to break my habit of crossdressing...
    JulieCakes JulieCakes 13-15, M 3 Responses Aug 11

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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 Jul 26

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    My younger sister always has male attention, I remember being in 7th grade and my sister being in the fourth and this guy who was also in 7th grade said he had a crush on my sister...
    onemorelonelygirl onemorelonelygirl 22-25, F 1 Response Aug 3

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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 3 Responses Jul 28

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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...
    banannasplitz09 banannasplitz09 22-25, M 2 Responses Jul 31

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