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I Crossdressed For My Mother

Personal Stories, Advice, and Support 482 People

    Something My Mother Would Have Loved...

    We were in Target yesterday to get some things for my daughter before she goes on a several day field trip with school. As we walked from the young girls section back toward the back of the store, we passed through the boys section. What surprised me was how the store had chosen...
    analogguy analogguy
    41-45, M
    3 Responses Sep 30, 2013

    Sort Of Belongs Here 2

    removed same reason
    rickibrat2 rickibrat2
    61-65, M
    Dec 8, 2010

    Mother's Wishes

    It all started as a punishment when i was about 13. When i had done something wrong in her eyes mother dressed me up completely as her pretty daughter. And as our family was seriously wealthy she did it in style and costs did not play a role she really went all out with it. It...
    misszaskia misszaskia
    51-55, M
    Oct 21, 2012

    Mom Helped

    i have an older sis who didnt want yunger brother so aroung age 3 or 4 started dressing me up mom thought it was cute and then found out it was also cheaper as i could wear most of sisters 2nd hand clothes it was different wierd and wonderful read my other stories
    sissykrisb sissykrisb
    51-55, T
    Dec 25, 2012

    I Hope You Are Not Offened By The Stories

    sorry for the posts but in many ways it helps to share things from the past to just deakl with the ghost this time of year brings guess most will never understand the pain of the ghost how crazy i was back rthen and how a few silly thing got me thought what was a living hdell in...
    rickibrat2 rickibrat2
    61-65, M
    Dec 8, 2010

    I Was Diapered And Dressed In Little Girl Style Dresses And Outfits By My Mom Until I Was Almost 19 Years Old.

    In my case, it all had to do with my father abandoning me and my mom, shortly after i was born. from then on, my mom hated men so much, that she dedicated the rest of her life towards raising me in ways, that would make sure i would always remain dependant on her like a diapered...
    AlanisAlicetoo AlanisAlicetoo
    56-60, T
    6 Responses Sep 18, 2010

    Not For My Mother, But For 3 Of Her Sisters...

    I was trained to dress with and for 3 of 13 Aunts from about the age 0of 5 or mother was one of the girls but didn't know what her sisters were doing with me on weekends (it was "our secret")... The whole maternal family was, I think, afraid of men since their father...
    SuzanneLebizarre SuzanneLebizarre
    70+, M
    1 Response Sep 19, 2010

    Sisters Playmate

    I'm sure that my Mother did not intend to make me a sissy, she was only trying to provide a playmate for my younger sister. She did this simply by providing yarn wigs so we both had long hair. It was fun pretending to be a girl with my sister and we did it often. I had many...
    EvieDrag EvieDrag
    66-70, T
    4 Responses Jan 17, 2011

    My Sister Dressed Me As A Little Girl.

    When I was 6 my older sister who was 12 would dress me as a 4 yr old girl. Her girl friend had little sister my size and I was quite small for my age. Her friend would come over with her sister and they would dress me. I had real curly hair and with a couple of bows and pink nail...
    deleted deleted
    1 Response Mar 18, 2011

    I Have Crossdressed For My Mother

           I, if you have read my stories, began crossdressing by the encouragement of my mother.   At the tender age of 11 she began to dress me as a girl. Over the next  5 years my closet grew with a whole assortment of dresses. ...
    bobbie13 bobbie13
    56-60, T
    13 Responses Aug 16, 2010

    Mom and Me...our Little Secrets

    My Mother knew I was "different" from my 2 older brothers. They were like my father, a true "man's man" in every sense. As a youngster, it was not uncommon to see her naked or nearly so with her knowledge. She also knew I had interest in her undies & would watch her don her nylon...
    janusatv janusatv
    61-65, T
    3 Responses Dec 1, 2010

    My Story Starts With My Aunt

    I went to spend a summer with my Aunt and Uncle in the country. I was 12 years old at the time. My Uncle owned a large farm, and he was out working 12+ hours each day. I was too young to do this work, and of course, I was a sissy. Even he knew this. But my Aunt was a seamstress...
    ChristinaMarietg ChristinaMarietg
    51-55, T
    5 Responses Sep 22, 2010

    mommyscdgirl mommyscdgirl
    36-40, M
    1 Response Feb 25, 2016

    Once again I find myself thinking how I became

    my mother’s girly son. I was driving to my mother’s house a few days ago to pick her up for our traditional weekly outing to Olive Garden for lunch. On the way my head was swirling with all sorts of doubts and random images of what I should have worn. And then I began to...
    deleted deleted
    7 Responses Aug 7, 2014


    My mother has known I have been a crossdresser since I was three or four. She has always embraced the femme side of me and that is sooo awesome. Makes life much better. Our favorite thing to do is have cocktails at lunch, go to the mall, and shop. She's Fab! She will help my with...
    rachelbgoodman rachelbgoodman
    41-45, T
    15 Responses Sep 12, 2010

    Parents Also Wanted A Girl

    i know as a little child i was dressed as a girl a lot of the time my parents wanted a girl and i was born a twin [which greated amny other problems along the way] but the twin die right after birth for some reason, i can remember my grandmother sewing clothing by had and make...
    rickibrat2 rickibrat2
    61-65, M
    Sep 12, 2010

    Teens Were The Best Years

    While I had started dressing as a girl when I was 5 by my 2 older sisters and then my mother. To me dressing up just meant putting on clothes. I was too young to know or understand what crossdressing was. As I entered my teens I became aware of crossdressing and being born a boy...
    femboy4u femboy4u
    7 Responses May 12, 2011

    How Jess Came To Be

    When I was growing up my parents divorced and I live with mom. It was the summer before high school and I had already been accepted to a coed private school. My mom was at work so I put on some of her clothes. I had on a pair of pink panties, a black bra, a pink blouse and a...
    supergirl0 supergirl0
    26-30, T
    4 Responses Jul 30, 2013

    Crossdressing With My Aunt.

    My crossdressing started when I was little by my sister then by my mother. It was a truely enjoyable experience and I have not regrets. While being dressed by my mother I was taught how to look and act like a girl. I developed all the feminine mannerisms associated with being...
    femboy4u femboy4u
    8 Responses Apr 12, 2011

    I've Been A Cross-dresser All My Life, It Started With My Sister Treating Me Like One Of Her Dollies

    I started cross dressing when I was very young at three years old. I had one older sister, who was five and she liked to treat me like one of her dollies and dress me up in her clothes. I didn’t mind, I liked the attention and from what my mother says I always liked it when my...
    amyast amyast
    8 Responses May 1, 2011

    Marcia (and Her Delightfull Wicked Stepmother)

    Follow up on "date boys"but to match it a bit better i included the first part with some minor adaptations in this one.Marcia part 1(made to date boys)My stepmother never really disapproved of my dressing up as girl, which i discovered in my early teens. She actually encouraged...
    misszaskia misszaskia
    51-55, M
    1 Response Mar 1, 2013

    Out In The Open

    Mom had not only caught me but also accepted me as Lisa and I went many places as Lisa with her but people only saw and knew me as a girl. No one knew or at least let on I was anything but a young girl. I was 11 when I started going out as a girl and here I was just past my 18th...
    LaceyLisa LaceyLisa
    61-65, T
    5 Responses Jul 29, 2012

    The Shopping Trip

    Hi Folks: I still owe you the second part of the true story about my GF. I had a hard drive crash and I'm still trying to recover my files. Like a dummy, I did not back anything up. I hope to recover the files rather than have to start from scratch. In the mean time I'd like to...
    francenemarch francenemarch
    66-70, F
    Jun 19, 2013

    Best Day Ever

    ok i was home alone so I went into my mums wardrobe and found a bra panties, pantyhose and a slutty French maids uniform. I went into my bedroom and jerked off. as I was cleaning the *** of my her uniform when my mum walked in and I was fully dressed. she stared at me an didn't...
    undercoverdresser2 undercoverdresser2
    18-21, M
    4 Responses Oct 12, 2011

    Moms Sexy Legs

    I use to watch mom get dressed for work when I was young that is when I found the luv for pantyhose they looked so good on her an felt so smooth as soon as she got home an got undressed I would sneak in her room an put her nylons on an the feeling I had is unreal it give me a...
    darla111 darla111
    41-45, M
    1 Response Dec 2, 2010

    For Mom And By Mom!

      When I was very young I can remember many, many times Mom would say, "You should have been a girl" I even was given a girls name at birth. I had a sister younger than me but I was small for my age and we both wore the same size clothes. Mom not having much money bought...
    boystud boystud
    2 Responses Oct 30, 2010

    Guees It Sort Of Belongs Here

    removed due to ameassge i was not wanted here
    rickibrat2 rickibrat2
    61-65, M
    Dec 8, 2010

    Not For My Mother, But For 3 Of Her Sisters...

    I was trained to dress with and for 3 (of 13!) Aunts from about the age of 5 or mother was one of the girls but didn't know what her sisters were doing with me on weekends (it was "our secret")... The whole maternal family was, I think, afraid of men since their father...
    SuzanneLebizarre SuzanneLebizarre
    70+, M
    2 Responses Sep 19, 2010

    Friday Night Movies

    The feeling of the silky teddie falling across my nipples the first time I tried it on for my Mom is one of my favorites from that time of my life.  It was the early '50s and I was around 10 yrs old and we lived near the naval base where my father was stationed and, of course...
    deleted deleted
    1 Response Mar 9, 2011
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