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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 234 People

    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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    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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    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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    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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    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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    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 13 Responses Jun 28, 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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    Related Experiences

    I started dressing in my mothers clothes when I was 10 with her leotards and tights. By the time I was fourteen I was wearing all of her clothes and dressing anytime I was home...
    MichelleTiedup MichelleTiedup 22-25, M 1 Response 1 hr ago

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    I'm a 20 year old guy looking for a crossdresser who wants a relationship with another guy. I will do anything u desire. I don't have any requirement but u have to be a...
    ilovecrossdressers ilovecrossdressers 18-21, M 2 hrs ago

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    I'm a guy looking for a crossdresser
    ilovecrossdressers ilovecrossdressers 18-21, M 2 hrs ago

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    I'm a guy looking for a crossdresser
    ilovecrossdressers ilovecrossdressers 18-21, M 2 hrs ago

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    I'm a 20 year old guy. Who is looking for a crossdresser. I will do anything with u. Msg me
    ilovecrossdressers ilovecrossdressers 18-21, M 2 hrs ago

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    Hi. I'm 20 years old and I'm looking for a crossdresser to be my girlfriend please msg me
    ilovecrossdressers ilovecrossdressers 18-21, M 2 hrs ago

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    oh I love leggings so much, a really sexy look and they feel amazing. A nice pair of panties underneath and it all feels great :) I really like to see leggings on women and other...
    GirlyLisaTG GirlyLisaTG 26-30, T 2 Responses 3 hrs ago

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    My first time I was 10 years old I was playing in my sister room and I was going through her dresser I found her bras and panties so no one was home I try them on and I though I...
    aliciafox55 aliciafox55 56-60, T 1 Response 6 hrs ago

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    I started Crossdressing about 40 years ago,Yes even old guys like it.Any way when I was 16 I decided to try on my mother's bra when she was not home.I loved the way it felt ,then I...
    Eav44dd Eav44dd 61-65, T 4 Responses 1 day ago

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    I remember mom trying on one of my older sister's skirts at age five. I also remember women saying I was a cute little girl, My response was "I'm a boy." What influenced me is...
    1della 1della 46-50, T 2 Responses 1 day ago

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    Hi friends my name is samiha(sameer) i am from vizag this is my real life story My crossdressing fantasy started when I was 16 I was studying my 9th standard.I didn't get any...
    samiharao samiharao 26-30 3 Responses 2 days ago

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    When I was younger I would sneak into my sisters room and put on her clothes. I loved being a woman. The feeling of the soft tight clothes around my body. Every time I made a new...
    clevername11 clevername11 18-21, M 3 Responses 2 days ago

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    I don't remember what specifically made me want to crossdress. I remember it started when I was very young. In fact, I don't have a memory of a time when I didn't do it. I have a...
    princessaliciacd princessaliciacd 36-40, M 2 Responses 3 days ago

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    I was 5 and wanted to be like my sister, so I took a dress and wore it. My sister found me out and let me wear it around the house and we played together as girls. As I got older I...
    bobbylee111 bobbylee111 41-45, T 4 Responses 4 days ago

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    My husband and I have been together for approximately 11 years, married for 4, and I am tired of absolutely FEARING getting together with my in-laws. They are such a judgmental...
    disarmlily1979 disarmlily1979 26-30, F 4 days ago

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    Another step forward today! I spoke to my boss, my immediate line manager, told him I want to come to work in a skirt, this is the bit I was dreading. His reply: "That is...
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 2 Responses 6 days ago

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    I decided to do sort of a crossdress dare to go in public without the possibility to chicken out. If you've read my previous story, I explained how I got caught and had to dress up...
    DCYDDON DCYDDON 18-21 7 Responses a week ago

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    I was raised by women my entire life. Throughout my childhood, women's clothing was not scarce by any means. I was the only boy in the house in fact (5 sisters, 3 aunts, mom...
    BoyNbraNpanties BoyNbraNpanties 26-30, M 7 Responses Aug 21

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    My first crossdressing experience startet with 23. Compared to others, i was late ;-) just found white stay ups from my gf and wondered how they would feel. It was love on first...
    Phoeni Phoeni 31-35, M 1 Response Aug 20

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 1 Response Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 3 Responses Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 1 Response Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 2 Responses Aug 19

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 2 Responses Aug 19

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    I am a 15 year old boy who is a sissy I wear my 18 year old sisters cloth, panties, lingerie leggings,bra,panties,dresses,make up secretly and Im attracted to masculine tough...
    deleted deleted 26-30 Aug 16

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    I am a 15 year old boy who is a sissy I wear my 18 year old sisters cloth, panties, lingerie leggings,bra,panties,dresses,make up secretly and Im attracted to masculine tough...
    deleted deleted 26-30 Aug 16

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    Cancel
    I am a 15 year old boy who is a sissy I wear my 18 year old sisters cloth, panties, lingerie leggings,bra,panties,dresses,make up secretly and Im attracted to masculine tough...
    deleted deleted 26-30 Aug 16

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    it was a long time ago when i was 16 but hope you enjoy this story as its true. It was August and my parents had booked a family holiday in Spain. there was 10 of us going my...
    louisetv louisetv 41-45 2 Responses Aug 14

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    most men talk about first time crossdressing was either mothers or sisters panties,bra or whatever,my first time was when I was around eighteen,was skipping school at a friends...
    charleen1952 charleen1952 61-65, M Aug 14

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    Part1 What a great day! I needed a new pair of shoes and so I had decided to go to the mall and see what I could find. I put on my bra, panties and pantyhose. I added a body...
    mat2Robin43 mat2Robin43 51-55, M 4 Responses Aug 13

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    Part 2 I walked out of the store and was feeling great about the encounter I had purchasing the shoes so I decided to walk the mall before I left. I had walked almost half of the...
    mat2Robin43 mat2Robin43