I Told My Sister That I Crossdress

Personal Stories, Advice, and Support 254 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

    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
    11 Responses Jul 18, 2010

    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

    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

    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

    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
    5 Responses Jan 28, 2010

    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

    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

    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

    told my sister that I like to wear her clothes

    today, I've been wearing her clothes for years since I was around 9 years old,(I'm 18 now) but anyway it's always bugged me that I've never told her about my habit for wearing her clothes, I started thinking about this last Friday, but couldn't build up the courage until today...
    deleted deleted
    26-30
    1 Response Mar 20

    Related Experiences

    I miss crossdressing. I need to own some clothes. Last time I did, it was just borrowed.
    Meow1357 Meow1357
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    1 Response Apr 20
    my sister I just found out was switched at birth, so now I have 2 sisters. 1 I grew up with the past 15 years of my life and 1 who is my biological sister that I just met! :)
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    lvrofhose lvrofhose
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    When I was 14 how I get feel I don't no but my heart told me to try this salwar kameez dress but my brain told me u r boy u can't wear such dresses then I didn't wear on that day...
    meghana120 meghana120
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    Hey EP is closing in two days. Im giving this a try. I Have always longed for a sisterly connection with someone, Anyone out there who wishes to have a sister to talk to frequently...
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    Lee124 Lee124
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    I tried getting along with her, I tried being nice.. But I can't ******* stand her! She's such a *****! She's ALWAYS bothering me and making fun of me! For no reason other than...
    ChocolateRain1309 ChocolateRain1309
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    1 Response Apr 16
    I told my last girlfriend. I commented on the fact that her bra and panties didn't match. She said she needed to buy new. I told her that I had some that would fit her. We spent a...
    Thejannettearmet Thejannettearmet
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    today my mom lift home for work after she lift I put a pair of panties on than my jeans a bra than my shirt I went to are apartment to check are mail I get back and that when I...
    gueenemma418 gueenemma418
    18-21, T
    1 Response Apr 14
    I have 2 sisters the elderly I haven't seen for years, as for next one I would get the chance to see her at holidays times.... Yesterday my mom was on skype and she call me to come...
    deleted deleted
    26-30
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    I'm not going to say that it runs in the family, but yesterday I was tending my grandkids when my two year old grandson went in the bedroom and brought out a dress that he wanted...
    Sharon03 Sharon03
    61-65
    3 Responses Apr 13
    Today I went to the thrift store to find some new clothes (well, old clothes i guess) and I almost got seen by a coworker that happened to be there with her boyfriend. Lucky I...
    CDMichelle16 CDMichelle16
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    This is embarrassing My name is Damien I am a male teen crossdresser It was a school day and I forgot that I had painted my nails last night red so it was no problem really. I...
    EvaMarie1406 EvaMarie1406
    22-25, F
    3 Responses Apr 11
    My sister in law.Is an amazing mother to my nieces and nephew.I don't know but it seems she cares about her father mother than my brothers.He barely sees his side of family.Which I...
    deleted deleted
    26-30
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    I don't "crossdress"! I femulate I express in the feminine I wear clothing that suits my expressions Q: Why don't we say tomboys are crossdressers? A: Crossdressing is a...
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    6 Responses Apr 10
    This is awkward. My sister just asked if I would ever have a three-way with her and a guy. I mean I love my sister but I don't know if I would take it that far.
    Syntagram Syntagram
    16-17, F
    1 Response Apr 9
    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
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    deleted deleted
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    deleted deleted
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    deleted deleted
    26-30
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    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
    deleted deleted
    26-30
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    deleted deleted
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    deleted deleted
    26-30
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    deleted deleted
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    deleted deleted
    26-30
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    deleted deleted
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    deleted deleted
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    deleted deleted
    26-30
    2 Responses Apr 8
    I'm a 15 year old sissy boy who secretly wears his 18 year old sisters bikini bra panties lingerie tights leggings panty house yoga pants dresses gowns tank top skirts and lipstick...
    deleted deleted
    26-30
    2 Responses Apr 8
    I am 16 years old and I adore crossdressing! Unfortunately, that means I have to wear my mom's clothing, which is a little awkward, but I can't help myself! I haven't worn panties...
    zmlmbnlfh zmlmbnlfh
    18-21, M
    1 Response Apr 8
    I have 3 sisters who outgrew me. i'm not very tall at 5ft. I went to summer camp for the summer. My 3 sisters were 12, 11, 9. I am 16. My oldest sister was 4'9 when I left, so...
    thyprinker thyprinker
    18-21, M
    1 Response Apr 7
    My sister is 14 and so am I. She is my step sister. She also lives in another city. She has tanned skin and mine is not pale or tan. It's bleh. She is extremely pretty. She is on...
    Lexibenson01 Lexibenson01
    13-15, F
    Apr 7
    My sister is 14 and so am I. She is my step sister. She also lives in another city. She has tanned skin and mine is not pale or tan. It's bleh. She is extremely pretty. She is on...
    Lexibenson01 Lexibenson01
    13-15, F
    Apr 7
    My sister is 14 and so am I. She is my step sister. She also lives in another city. She has tanned skin and mine is not pale or tan. It's bleh. She is extremely pretty. She is on...
    Lexibenson01 Lexibenson01
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    Sisters FOREVER!!!!!!
    JennyTom JennyTom
    41-45, F
    Apr 7
    Stopped by to see my sister before she left for work and had to take this selfie of her beautiful high heels, Love the SIS!!!!!
    JennyTom JennyTom
    41-45, F
    3 Responses Apr 7
    If all the crossdressers could pick up the underwear and toys on their way out. That would be great. -shakes head- We'll never get the deposit back....
    JessicaMarie35 JessicaMarie35
    36-40, T
    3 Responses Apr 7
    I miss the sister I never had. So do my parents. They kept trying to have a girl, and I'm the sixth and last attempt. They gave up. I'm sorry I was not the girl they wanted. I...
    9minute 9minute
    18-21, M
    1 Response Apr 6
    For me to say that I like to crossdress would be understating it. I absolutely love cross-dressing. I hope to get my life in order so I can become as feminine as possible. Females...
    Thejannettearmet Thejannettearmet
    51-55, T
    3 Responses Apr 6
    I am a fiftyfour year young crossdresser. I have been cross-dressing since I have been seven. I can think of many things that I would enjoy discussing with other crossdressers...
    Thejannettearmet Thejannettearmet
    51-55, T
    Apr 6
    My first time really getting caught I was 11 or so. I had been cross dressing for a while, but don't think that I had been caught. One night when I thought everyone was out, I...
    lauratdc lauratdc
    46-50, T
    Apr 6
    I first found my sisters underwear when I was about 6 years old, and put them on. They felt so natural, that i kept wearing them. I haven't stopped since.
    lauratdc lauratdc
    46-50, T
    3 Responses Apr 6
    Two weeks ago my sister in law and I were having wonderful sex when her daughter walked in on us. Talk about being embarrassed.
    deleted deleted
    26-30
    Apr 6
    My sister sent me this selfie, I cropped her head, on her new leather skirt she will wear to my pig roast Saturday!!!!!
    JennyTom JennyTom
    41-45, F
    11 Responses Apr 6
    I FEEL very bad about this but I can't stop myself. I know I will hurt my sister very bad one day but I can't stop from hurting her. She makes me so mad sometimes. I don't know how...
    jack197576 jack197576
    41-45, T
    Apr 6
    Last weekend a young male teenager who was a crossdresser was assaulted and ran over and is in critical condition. The newspaper,La Times, had this has their lead paragraph, Young...
    lvrofhose lvrofhose
    56-60, M
    1 Response Apr 5
    I love crossdressers because it takes courage. The further you go the more courage you have. I really hope I can get good enough to go out on a date as a woman.
    Thejannettearmet Thejannettearmet
    51-55, T
    1 Response Apr 5
    No I don't!, You know I don't, but if you want to tell me all about your older sister, go ahead, little sister always has the juiciest stories 😃😃😃
    1LikeMind 1LikeMind
    51-55, M
    Apr 5
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