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I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 225 People

    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 10 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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    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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    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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    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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    Related Experiences

    Well i guess everyone all had different experience,but my first crossdressing experience was when i was about 7 and i used to try on my mum cloths and shoes and bags and walk...
    princess221 princess221 22-25, T Feb 23

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    I was having fun on a day off of school crossdressing I had a pink bra and a nice thing on and my sisters old prom dress on and my cousin happend to stop by and he thought that it...
    Cdkyle Cdkyle 18-21, T 5 Responses Feb 13

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    Some notes about the meeting at the Ingersoll Gender Center on Wednesday; I arrived early as I was unsure of the location and allowed extra time to get there. It's dark and rainy...
    JessicaDale JessicaDale 51-55 13 Responses Feb 6

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    I have dated my boyfriend for 3 years and close to completing our first full year together he opened up to me about his fascination with women's makeup. At first I thought it would...
    luna811 luna811 18-21, F Feb 16

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    I have dated my boyfriend for 3 years and close to completing our first full year together he opened up to me about his fascination with women's makeup. At first I thought it would...
    luna811 luna811 18-21, F 4 Responses Feb 16

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    Now that I think about it, I have no idea. I started secretly dressing in my Mom and sister's panties at 9 or 10. I'm 28 now and now I have my own collection of lingerie but I...
    AnonymousSissy86 AnonymousSissy86 26-30, M 3 Responses 4 days ago

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    My 3 step sister's they forced me to wear a school girl uniform and then told there mum who took great fun in forcing me to never wear boy clothes again i...
    subsissy1989 subsissy1989 26-30, M 4 Responses Feb 14

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    My older sister spanked me one time growing up. I was around 10 or 11 and she was around 14 or 15. My parents were both at work and my sister was in charge. I was playing...
    tdw195 tdw195 26-30, M 1 Response 4 days ago

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    As I was literally hitting post telling about my first experience wearing ladies jeans in public. I didn't have courage to wear more than that. Though I did have black heels and...
    tpc2001 tpc2001 31-35, M 1 Response Feb 16

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    I love to crossdress my mother caught me in her clothing and started dressing me up like a woman
    sexybaby6988 sexybaby6988 51-55, M 4 Responses Feb 22

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    We went for a pedicure and I got my toes painted glittery gold. Then we speed at the beauty supply store and I bought some matte finish top coat polish for my fingers. As we drove...
    Sharon03 Sharon03 61-65 12 Responses Feb 19

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    Today, just a few hours ago, I found out that my twin sister was transgender bisexual. She told me right after we got home from school when I asked her if she was okay. She looked...
    clv321 clv321 18-21, F Feb 5

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    I went over to my mums with my son to bake some cakes with my sister Vicky. My sister alison had a sour face and was being verbally aggressive the minute we got through the door...
    Whinny00 Whinny00 26-30, F 1 Response Feb 16

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    I cannot even begin to express how much my little sister hurts me. And I mean the mental kind of pain, not physical. A few years ago I was talking to this boy, and I even went as...
    courtneylightsupthesky courtneylightsupthesky 18-21, F 1 Response 6 days ago

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    I am a strait male crossdresser, and I enjoy thinking about myself as a pole dancer. I would like to feel that energy of femininity. It all started in my puberty during stressful...
    levalo levalo 31-35, M 4 Responses Feb 7

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    I am a long time crossdresser. I have been wearing female clothes whenever I can from about the age of 10. No I do not concider myself a freak or bad. I just have a strong female...
    taracd55 taracd55 56-60, M 2 Responses 4 days ago

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    I have been caught twice. when I was 12, I used to wear my moms pantyhose, heels and dresses...also makeup and her wig. I hid them in the corner of the bathroom behind the tub...
    dressupgina dressupgina 41-45, M 2 Responses 4 days ago

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    My husband loves me we have 1 daughter but My mother inlaw always jealous of me she always conpet with me specially in cooking....My Sister Inlaw All of them !! They hate me...
    Romechan Romechan 31-35, F 6 days ago

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    Part 1 As one day mom an sister were gone for the weekend as I got from work. I walk to my room to change. As I walk by my sisters as it. Was across the hall. from mying. As I...
    safty0700 safty0700 56-60, M Feb 24

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    Well thanks to a couple of friends here on Ep they helped me understand that its fine if i crossdress. I have learned that purging my crossdressing does nothing and that i should...
    HaydenJT HaydenJT 18-21, M 5 Responses 1 day ago

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    I think its two things that did it for me. my mom left my dad when I was 5 months old spent the fist 5 years with just her and my brother and always wanted to be strong like her...
    jamie172 jamie172 46-50, T 1 Response Feb 8

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    I don't know why I picked up that pair of my Mum's panties out of the laundry hamper when I was about 12 but wow they felt incredible on. Just blew my mind. I think it was...
    BrightLight750 BrightLight750 46-50, M 6 Responses Feb 21

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    My earliest experience with dressing in girls clothes, I was 5 years old. My Older brother encouraged me to put on my sister's bathing suit. It felt so good next to my skin. I...
    mandywantsit mandywantsit 51-55, M 1 Response 4 days ago

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    Today, 5 years ago was the day that my sister in law showed her true colors when she walked into the hospital room and announced her self to everyone as" THE SISTER!" ( side note...
    DisowningSIL DisowningSIL 51-55 2 Responses Feb 17

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    I used to be friends with a female co-worker who adored the fact that I enjoyed wearing female attire. It took a long time for us to realise this. I got invited to her flat one...
    crosser50 crosser50 61-65, M 1 Response Feb 20

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    its been a month since I found out that terrible news. the pain isn't easier or lighter, I've just gotten better at distracting myself from it because time doesn't stop. and life...
    HealingMyHeart HealingMyHeart 18-21, F 1 Response Feb 22

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    I crossdress and my wife loves that I crossdress. She agrees that lingerie is certainly not just for women to wear us men can wear sexy things also and she appreciates that I wear...
    pantiescouple pantiescouple 26-30 6 Responses Feb 23

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    I first crossdressed as a teenager, I have no recollection of desiring to crossdress pre teenage. My initial dressing was in knickers (panties), and as teenager I always wanted...
    MandytgAndy MandytgAndy 70+, T 6 Responses a week ago

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    When I was 16, my parents separated. It was devastating for my 2 sisters and I (let alone our mom). From the day our parents sat us down and told us, we made a pact that we will...
    Yankeegurl1216 Yankeegurl1216 41-45, F 1 Response 6 days ago

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    Didn't know if I should write this but..its nice to talk to people and to share my stories So growing up with my older sister and two younger brothers, wasn't amazing. I mean yeah...
    Artyhallows111 Artyhallows111 18-21, F 3 Responses Feb 19

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    Bidding adieu to my sister after her marriage was the memorable moment of my life. I never told neither did, I showed it to her, but she was the person who understood me. I love my...
    Lakshay1993 Lakshay1993 18-21, M 1 Response 14 hrs ago

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    Part two So my mum came back with bags full of shopping and told me to sit down she said I knew you was dressing up in my stuff I just never caught you and I wasn't going to bring...
    missjazzmin missjazzmin 18-21 7 Responses Feb 5

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    Went out fully dressed a few weeks ago. Wore a white and purple striped top, black skirt and black 5 inch pumps. Looked and felt awesome. Left very early in the morning. Went...
    83218tb 83218tb 36-40, M 2 Responses Feb 7

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