Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Crossdressed For My Mother

Personal Stories, Advice, and Support 504 People

    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 Feb 21, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 7 Responses Oct 12, 2011

    Your Response

    Cancel

    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 6 Responses Mar 30, 2012

    Your Response

    Cancel

    I Cross-dressed For A Lot Of People Sides My Mom!

      My Life as a Young Boy About age six I began a career as a child model, modeling for a local agency with many national accounts. My mom was a licensed agent in this state and because of her own notoriety; she was able to keep me working regularly at the local and national...
    theBillyandBudBear theBillyandBudBear 66-70, M 4 Responses Jan 7, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 9 Responses May 1, 2011

    Your Response

    Cancel

    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 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 1 Response Sep 19, 2010

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    I Enjoyed The Best Of Both Genders As A Young Boy.

     (Read my 50 plus 'ventures on EP under I LOVED DRESSING LIKE A LITTLE GIRL, and follow me through my wonderful world as a young boy.)         About age six I began a career as a child model, modeling for a local agency with many national accounts. My mom was a licensed...
    theBillyandBudBear theBillyandBudBear 66-70, M 5 Responses Jan 25, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Sort Of Belongs Here 2

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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Guees It Sort Of Belongs Here

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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 2 Responses May 12, 2012

    Your Response

    Cancel

    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 11 Responses Apr 12, 2011

    Your Response

    Cancel

    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 8 Responses Dec 1, 2010

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 26 Responses Jan 15, 2011

    Your Response

    Cancel

    Related Experiences

    My daughter is not inviting me to her wedding this July and then when I saw her invitations at my other daughter's house, I couldn't believe my eyes! My daughter only put down that...
    JulieJi JulieJi 51-55, F 1 Response a week ago

    Your Response

    Cancel
    In one second a choice is made to give your baby a chance at a better life.This choice will forever change you and your baby's life forever.They tell you how great you are for...
    lovely2463 lovely2463 31-35, F 1 Response 6 days ago

    Your Response

    Cancel
    Its your fault. I love sharing in Experience Project, because I won't get blamed for mother behavior. "She forgets. You should remind her." "She didn't mean it. You misinterpret...
    fien fien 26-30, F 2 Responses Apr 1

    Your Response

    Cancel
    I was 16 when my mother got into a car accident. She was in a coma for 2 months before we decided to take her off life support. She was the coolest mom ever. Now I'm like desperate...
    Jill0829 Jill0829 18-21, F 2 Responses Apr 2

    Your Response

    Cancel
    Update: Sil (my husband’s brother’s wife) and I used to be good friends, after I moved out, she turned against me. She was upset that I moved out, and stated that I stole my...
    genie201 genie201 31-35, F 2 hrs ago

    Your Response

    Cancel
    As I'm making the transition from male to female, I have made my work aware of this and will be going to work as Lucy full time from the end of April :) My colleagues were told in...
    LucyTG LucyTG 26-30, T 5 Responses Mar 25

    Your Response

    Cancel
    Today I went on a bit of a shopping spree for living as Lucy full time. I got a few skirts, dresses, tights, some heels and flats and some bra and panties. I came out with quite a...
    LucyTG LucyTG 26-30, T 1 Response Apr 1

    Your Response

    Cancel
    Well that's me ready for my date, I'm so excited about meeting Alex at the local T Girl friendly bar :) I am wearing a royal blue dress, nude tights and nude heels. Underneath it...
    LucyTG LucyTG 26-30, T 6 Responses Apr 2

    Your Response

    Cancel
    Well that's me ready for my date, I'm so excited about meeting Alex at the local T Girl friendly bar :) I am wearing a royal blue dress, nude tights and nude heels. Underneath it...
    LucyTG LucyTG 26-30, T 3 Responses Apr 2

    Your Response

    Cancel
    Im starting a Ki.K group chat ANY full time cross dressers under the age of 30 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 1 Response Apr 5

    Your Response

    Cancel
    Right now I am wearing some shiny black tights with a garter belt and stockings over that. I have on a black 48DDD soft cup bra with two sets of breast forms inside (I like to have...
    kathej kathej 66-70, M 10 Responses Apr 7

    Your Response

    Cancel
    Today I'm heading out to meet some friends at a local bar for lunch and a few drinks. I'm wearing a nice red dress, black tights and some flats. Gone for the sensible option on...
    LucyTG LucyTG 26-30, T Apr 12

    Your Response

    Cancel
    Well I'm back from lunch and drinks with friends and had to write this to fill you all in :) I was having a wonderful time when I excused myself to go to the toilet. On my way back...
    LucyTG LucyTG 26-30, T 1 Response Apr 12

    Your Response

    Cancel
    Well I'm back from lunch and drinks with friends and had to write this to fill you all in :) I was having a wonderful time when I excused myself to go to the toilet. On my way back...
    LucyTG LucyTG 26-30, T 2 Responses Apr 12

    Your Response

    Cancel
    Yesterday was very warm, mid 70's and breezy so I took a walk around the park. About a mile loop. Quite crowded with others out enjoying the first nice days of spring. I wore...
    burkaboy burkaboy 26-30, M Apr 14

    Your Response

    Cancel
    Today was my first appointment at the Gender Clinic and it all went very well. The staff there were very welcoming and I was put at ease straight away talking to them. I made...
    LucyTG LucyTG 26-30, T 3 Responses a week ago

    Your Response

    Cancel
    I'm off out to meet some friends for a bank holiday catch up :) Love being out and about as Lucy. Today I'm wearing a nice black dress, 40 denier black tights and nude heels. I...
    LucyTG LucyTG 26-30, T 3 days ago

    Your Response

    Cancel
    That was Easter. Lovely warm day. I wore a tan dress with matching bonnet bedecked with flowers. Frilly collar light tan gloves. While I seldom wear anything under, this time...
    burkaboy burkaboy 26-30, M 1 Response 1 day ago

    Your Response

    Cancel
    Everyone if you haven't you should read my first story as this follows on. Well Karen and I talked to late and we decided we needed sleep so she gave me a nightie and gave me a...
    CDresser2 CDresser2 18-21, M 7 Responses Apr 15

    Your Response

    Cancel