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I Crossdressed For My Mother

Personal Stories, Advice, and Support 496 People

    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 22-25 10 Responses Apr 12, 2011

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    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 6 Responses Oct 12, 2011

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    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

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    Shopping

    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 16 Responses Sep 12, 2010

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    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 2 Responses Sep 30, 2013

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    I Love Women's Worn Lingarie

    I am an Indian. Male wearing women’s dresses. But I am not gay. Am straight, married and have child. At the age of 8 or so first I took my mother’s saree piece and privately wrapped around my waist Immediately I got erection.I pressed my penis with that saree piece. With...
    lingarielover lingarielover 31-35, M 1 Response Mar 3, 2012

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    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 6 Responses Sep 22, 2010

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    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 51-55 1 Response Oct 30, 2010

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    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

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    I Love To Wear Women's Worn Dresses.

    I am an Indian. Male wearing women’s dresses. But I am not gay. Am straight, married and have child. At the age of 8 or so first I took my mother’s saree piece and privately wrapped around my waist Immediately I got erection.I pressed my penis with that saree piece. With...
    lingarielover lingarielover 31-35, M Mar 3, 2012

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    When I was in my 40s

    and was very accomplished dressing and went out often, I invited my mother to visit for a week. I had told her about me as a woman and this was my chance to show her. She was surprised that I looked as good as I did and in a very motherly fashion told me I wore too much...
    slipgirl274 slipgirl274 61-65, T 2 Responses 4 days ago

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    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

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    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

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    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 22-25 8 Responses May 12, 2011

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    Sort Of Belongs Here 2

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

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    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

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    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 26-30 1 Response Mar 18, 2011

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    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 5 Responses Sep 18, 2010

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    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

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    Guees It Sort Of Belongs Here

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

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    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 31-35 8 Responses May 1, 2011

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    She Did It

    I do believe mom dressed me in dresses when dad was at work because she wanted a little girl. That was until my first sister was born 3 1/2 years later. I have always wanted to wear dresses when I was young and tried to wear my sisters clothes but they were really tight. But the...
    Adam59 Adam59 56-60, M 1 Response Feb 21, 2013

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    With Her Approval

    I'd been crossdressing, rather amaturely, for a while, before my mother found out. She was mad because I told her I was snitching things from laundry rooms and she insisted I stop. Stealing the clothes, not wearing them. I was able to keep all I had taken. After a while she came...
    josilver josilver 56-60 5 Responses Feb 21, 2012

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    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 26-30 1 Response Mar 9, 2011

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    Mom "made" Me Do It.

    My mom always wanted a girl to dress up and fuss over. She started dressing me as a girl for halloween, when i was 2. Each year it was lipstick, nail polish, tights or stockings etc. princess, ballerina, cheerleader, etc. When I started protesting, as I got older, she begged me...
    sissyjackie2008 sissyjackie2008 46-50, T 27 Responses Jan 15, 2011

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    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 7 Responses Dec 1, 2010

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    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 1 Response Oct 21, 2012

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    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 so...my 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

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    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

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    Kristen Pleased His Mother

    Submitted for kritsen4 ,unable to post in the group due to her being under 18 Kristen tells me at a early age3 or 4 his mother started holding his older sisters dresses infront of him and she made comments about the dresses still being in great shape even after his sister had...
    LadyBeverly LadyBeverly 18-21, F 5 Responses Mar 30, 2012

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    Chapped Lips

    I remember being little and getting chapped lips in the wintr time, one time it was really dry air and my lips were so chapped they bled, Mom decided to protect my lips, she started applying a lipstick to them and it really helped. My lips never dried out again that winter as...
    Kristen4 Kristen4 18-21, F 1 Response May 12, 2012

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    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 61-65, T 4 Responses Jan 17, 2011

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    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

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    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...
    kayleew2000 kayleew2000 18-21 4 Responses Aug 7

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    I live in los Angeles and want to go out crossdressed. im not afraid to I just want a friend to do it with!
    advertadrien advertadrien 22-25, M 2 Responses Aug 4

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    ​Last weekend {7/18-20/14) my wife allowed me to dress for her. It was so much fun waking in the morning with my makeup and everything still on.7-18-147-19-14
    stefiecdtv stefiecdtv 51-55, T 17 Responses Jul 22

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    I go out cross dressed regularly. I am very comfortable as my feminine self. I have the opportunity to go out as I travel regularly. One of the special times I have had lately...
    RandiHill RandiHill 51-55, M 4 Responses Jul 22

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    This is getting to be a difficult question to ask, since I incorporate so many feminine things in my daily attire. For example, my watch and purse are visible. Some of my sweaters...
    PennySterling PennySterling 51-55, T 3 Responses 5 days ago

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    I wore a Green maxi dress with nude coloured sandals. Underneath I had a matching black bra and knicker set. I really felt amazing and stayed in the outfit for the whole day. Love...
    LisaTG LisaTG 26-30, T 1 Response 3 days ago

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    Been asked out on a date but what to wear ? should I wear my new blue dress which is a mid length or a silk blouse and pvc pencil skirt cant wait for tonight.
    girlynicole girlynicole 36-40, T 4 Responses 1 day ago

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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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    One of my favorite activities is shopping for my own clothing while dressed as a girl. I am fairly passable but I am sure I get read. It is truly enjoyable trying on all the nice...
    RandiHill RandiHill 51-55, M 7 Responses Aug 11

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    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 17 hrs ago

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    i hate that person who gave birth to me she is not fit to be called a mother she has not got a loving caring bone in her body,and i will shed no tears over her when she is dead...
    siac siac 56-60, F 2 Responses Aug 3

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    Hello everyone. I never wanted to resort to this, but I feel I am out of other options. Let me start from the beginning. When my mother, Dee, was 9, her father was shot in the head...
    NikkiNINTR NikkiNINTR 18-21, F 2 Responses Aug 6

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    I miss my all mothers. I miss my mother who gave birth to me. I miss my Other Race mother, who taught me to dress,cook, clean, read, write, wash dishes to sweep and mom floor. I...
    PathologicalLair PathologicalLair 26-30, F Aug 13

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    I will not rant or moan and I no longer hate my mother as much as I use to,but I hope I NEVER see her again and haven't since the last time I went before a judge aged 10 and her...
    Selah94 Selah94 18-21, F 3 Responses Jul 23

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    I was unfortunate enough to land myself in a house that includes not only my husband but along with my in laws, sister in law, her husband, and two kids. Everyone knows and can...
    destinii3 destinii3 26-30, F 4 Responses Jul 23

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