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I When I First Dressed As a Girl

Personal Stories, Advice, and Support 1,329 People

    Thank You Vanessa

    I can vividly remember when I was about 7 playing with the girl next door. She was a little older than me. The same age as my brother. We quite often went in their hut in the garden, particularly when it was raining, as it was today. Out of the blue she suggested that why do we...
    sarahuniform sarahuniform
    51-55, M
    4 Responses Mar 14, 2011

    As A Girl

    my mother dressed me as a girl in sisters clothes till i was 4 and i loved being dressed in panties and dresses
    pntyguy pntyguy
    Nov 13, 2011

    The first time i dressed i was having sex with

    my exwife we were fooling around and i looked at her and said i would love to wear women clothes she didnt know its really started when i was ten but back then it was only panties and bras as i was saying i told her i wanted to dress like a woman she was ok with it so i borrowed...
    deleted deleted
    1 Response Aug 16, 2014

    By My Aunt

    The first time I can remember being dressed like a girl was when I was about 5 or 6 years old. I had gone to my aunt and uncle's house to stay for a few days. My mum let me pack my own clothes for the stay, and didn't check what I put in my bag. I remember that I chose mum's...
    femininityforme femininityforme
    46-50, T
    7 Responses Jan 25, 2011

    Aunt Dressed Me Up

    i must have been around 12 or 13 my aunt asked me if i wanted to play dressup, i said sure, so she dressed me like a girl and we took pics, it was silly and innocent....when i went home though i began trying on moms panties, first in my room, then when i went outside , the thrill...
    deleted deleted
    1 Response Dec 6, 2012

    First Time

    at age 6 put on first pair of panties. six weeks later first time fully dressed been at ever since
    spaz2692 spaz2692
    1 Response Jan 2, 2012

    The first time I dressed

    as a girl was either when my sister would give me makeovers which I enjoyed Or when I was older I would not go out for dinner and the house would be empty and I would take my sisters clothes makeup and shoes. I will tell you both stories. When I was 5 or 6 my sister D (I...
    EvaMarie1406 EvaMarie1406
    22-25, F
    2 Responses Jan 23, 2016

    First Outfittup

     I was riding my bike home when I was 7 years old. I saw something laying on the ground and stopped and picked it up. I thought it was a blouse made of a nylon/spandex type material, and I just loved the feeling of the material and had been wanting to try on girls clothes...
    loverhumbapanties loverhumbapanties
    41-45, M
    6 Responses Jul 1, 2009

    My Girlfriends House

    Now I don't know if this one counts as I have dressed up as a girl when it was halloween to go to the mascarade dance.  But it is a first time I dressed up as a girl at my girlfriends house.  So here it goes.  When I was 16 yrs old I was going out with this girl...
    sexyblackpantyhose sexyblackpantyhose
    31-35, M
    11 Responses Jun 29, 2009

    I remember my first time dressing

    as a girl. My parents were gone for a week and my sister had moved into her college dorm, so I was home alone. I wasn't really into any weird stuff, I was just curious to try on some women's clothing, as I never had before. I remember picking out a short skirt, a tight white...
    deleted deleted
    5 Responses Sep 21, 2014

    So It Begins

    This would of been in around 9 when I first found the spare clothes box and preceeded to gingerly take a blouse, skirt and socks from there and stood up and thought "Wow". I loved how it felt - it just seemed right - and from that day on whenever my folks were out I'd spend time...
    deleted deleted
    Jul 27, 2012

    The Play's The Thing

    As a prepubescent boy, I sang soprano in a boys’ choir. One year, the director decided we would put on a production of Gilbert and Sullivan’s’ “trial by Jury”. The older boys whose voices had changed played the male parts and the rest of us were assigned girls parts...
    NikkiDare NikkiDare
    Oct 2, 2013

    The First Time I Dressed

    I started wearing my sisters panties when I was 5. As time went on I tried more and more of her clothes. When I was 12 it was Holloween and I was going to dress as a sexy girl for a party. I was going with my best freind and he thought it would be fun for me to dress up like that...
    jiminpanties jiminpanties
    36-40, M
    4 Responses Apr 11, 2013

    My First Summer As A Girl

    it was back in the late 70s i spent the summer in Kansas at my aunts house she didn't know any things about boys so i had to dress as a girl and and i had to have my nails done and all the 9 yards i even had to wear night gowns my couison and i was the same age so when my aunt...
    Donna16 Donna16
    2 Responses Oct 12, 2013

    I First Dressed As a Girl For My Friend.

    One day when I was staying at my friend's house.  His mom had already gone off to work and Terry and I were still sleeping.  The night before he and I were watching the Crying game.  We thought that would be real cool to have sex with someone like that as he...
    silkiehosewearer silkiehosewearer
    31-35, M
    25 Responses Jun 30, 2009

    I Can Recall Fairly Well That Trial That Changed My Life

    I grew up in a home with three sisters, so there was a lot of feminity around. There was a lot of borrowing of clothes, so something being not exactly where one last left it or expected it was not particularly uncommon. I don't remember how old I was, probably pre-teen, but it...
    wcurnow wcurnow
    51-55, M
    2 Responses Sep 26, 2012

    Hardee's Ladies Room

    It wasn't my first time to go out dressed, but another post triggered this memory. I used to love to be away from the office for the day. Once safely out of town I would pull into a safe spot and carefully remove my undershorts and slide into a pair of panties. I'd typically...
    kimthomas2013 kimthomas2013
    41-45, M
    32 Responses Jan 15, 2013

    Now then when the family would leave I would go

    and sneak my sisters nail polish bright Red. I would paint my toes with it
    EvaMarie1406 EvaMarie1406
    22-25, F
    Jan 23, 2016

    I Just Remember Opening Tights,and Thinking Hurry Up And Get Them On.

    pinkfloyd1973 pinkfloyd1973
    36-40, M
    Apr 8, 2012

    First Time Out Completely Dressed As A Girl

    I probably mentioned in some of my posts that I have been crossdressing since I was 5 or 6. I have gone out on occassion completely dressed and made up, but only late at night where no one saw me. This story is about the first time I went out where people did see me. I was in...
    dondonna415 dondonna415
    51-55, M
    2 Responses Feb 9, 2011

    Something Just Occured To Me!

    I had one idea which might be useful in teasing sissy boy! Ladies, why not dress your panty boy in a 1- or 2-piece GIRL'S bathing suit, Get him a glorious very brown tan and then take him to a normal beach or even a clothing optional one? This might make for an i9nteresting time...
    noellecasely noellecasely
    31-35, F
    28 Responses Jul 3, 2012

    First Time Dressed

    Having read through a lot of the stories its seems quite common for some girls to have their first experience dressing up for a school play. mine is a somewhat similar experience though not quite as typical. I was 7 when we had to put on a school play and i was picked...
    suzifromek suzifromek
    26-30, M
    5 Responses Jan 5, 2010

    I spent a good amount of time from the time I

    was in the 7th grade dressing up when I was alone, or playing around my house outside dressed as a girl. I never found that I felt the clothes for better, or that it was liberating, or anything like that... I wore it because I really wanted to experience getting f*cked wearing...
    WillingStudent WillingStudent
    41-45, M
    May 20, 2014

    Dressed To Be A Grade 10 *****

    I've already told the story of how I became the school **********. By the second semestre of Grade 9, I was arriving at parties and being directed to a bedroom where I'd undress and wait for guys to come and **** me - in the face or in the ***. Often thheir girlfriennds...
    onmyknees4strangers onmyknees4strangers
    6 Responses Feb 21, 2011

    Not Too Sure

    I am not too sure of my first time but I do remember wearing at a very early age and I swiftly became obsessed with stockings, nighties, slips, and body suits. In my early teens or just before I began to absolutely love bras and began experimenting with a wide range of others...
    Aeslyn Aeslyn
    36-40, T
    Apr 7, 2012

    My Friend's Opinion

    My mother started dressing me when I was 11 and this how it started. I was at a friends house who is a girl in fact while my mother was working as a cashier at a grocery store. We were riding our bikes having a lot of fun. Later my friends mom called us in for lunch, she made us...
    Jacklyn13 Jacklyn13
    61-65, M
    1 Response Jun 10, 2012

    My Feminization Process

    When I was 11, I went to live with my uncle and his much younger wife who was only 10 years older than I (my parents had both died in a car crash).  My aunt (by marriage) I thought was a hottie and when my uncle was away (he traveled a lot) she would mostly go about the...
    SissyGena SissyGena
    31-35, T
    13 Responses Nov 12, 2009

    Dress To Go Out

    It was when I was about nineteen over the the years I got my set of pantys and garter belt with a bra or two, and some fish net nylons and regular nylons,but my biggest thing I got was a mini skirt and a top so the next weekend I decided to get dress and drive around and see...
    michellmartinez4 michellmartinez4
    11 Responses Mar 11, 2011

    Dressed And Having Fun

    The first time my mom caught me dressed as a girl i was 16.I was out having fun and came home about 11:00pm.with a friend of mine.Nobody was home.My mom worked as a bartender then.It was Friday night i knew she didn't get off work uti 2 in the morning.Me and my friend was fooling...
    scotsil scotsil
    51-55, M
    3 Responses Jul 9, 2013

    It Is All My Mum's Fault !!!

    When I first dressed as a girl, I was only 6 or 7. My mum made a ballet/dance dress for a friend's daughter and because we were the same size, I had to try it on. For years after that, when we went to visit these friends, me and this girl would dress-up in her bedroom, she had...
    LauraJaneW LauraJaneW
    10 Responses Dec 10, 2010

    My First Time Dressed.

    It all happened when I was in the 3rd grade. My little brother Al (2 years younger) and I went to visit with friends that lived down the road in rural West Virginia. Trevor was the same age as I, and Jennifer was the same age as Al. Being those ages, we didn't want to play...
    beher12 beher12
    41-45, M
    17 Responses Nov 21, 2011

    First Time Dressing

    My first time dressed as a girl was I put on my mom's one piece yellow bathing suit and a pair of pantyhose, with a added breasts and I don't know why I did it but I found a pair of pantyhose that had a run in them so I decided to put some rice in them to make my breasts.    I...
    deleted deleted
    3 Responses Apr 16, 2013

    Hotpants Outfit Was Probably The First Time Fully Dressed.

    The first thing i tried was my mother's stockings when i was around 5 or 6. They were way too big and baggy at that age, but i loved the way that it made my legs feel - a kind of weird cool feeling as the air passed through the mesh.The next thing i can remember about being...
    teather teather
    1 Response Feb 6, 2011

    Dressed For The First Time

    I was 11 years old and home alone during summer days. I had been having dreams and fantasies about being a girl and actually had breasts at that age.  One day i pilfered in my mom's closet and dresser, and found an old pair of nylon brief panties and a bra, then dug out a...
    CissiGail CissiGail
    51-55, T
    8 Responses May 6, 2013

    I Wanted To Never Wanted To Take The Dress Off

    I was young, wasn't in high school yet. I was at a friend of my mom's house. The wives were downstairs bitching about their husbands while drinking. I was upstairs with the friends daughter who was a few years older than me. We were talking about stupid stuff while looking...
    stacygurl86 stacygurl86
    31-35, T
    5 Responses May 2, 2013

    Dress All the Way,

    ii was 14 mom left me home buy myself for the weekend.i started with blue silkpanties and a laced blue bra then i put on tan pantyhose then alight silk blue blouse then i slip on a blue jean miniskirt and i but on hiheels. after that i put on makeup did my hair witch is long...
    aprilwalls aprilwalls
    46-50, T
    5 Responses Jun 2, 2009

    1st Time Out For Real

    just left school 17 years old mum has been very helpfull over the years.althought i had been out with her as young 13 14 year old girl, dress, socks and panties yuk. mum said i should stop doing it or do it right. 2months later in sept 1977 we went on holiday great yarmouth,we...
    girlslegs girlslegs
    46-50, T
    Aug 8, 2009

    Lost A Dare (or won one depends on your POV)

    It seems most stories start like this.  I had been wearing pantyhose for years. Sneaking them out of the trash,  trying them on at night when I could but it finally happened when I was in High school.  On night my G/f and I were hanging out in my den.  We had been out...
    deleted deleted
    7 Responses May 19, 2011

    Junior School Concert

    My earliest recollection of dressing as a girl was when I was in the second grade. The class play for the junior school concert involved having half the class play the role of girls. Possibly since I was small-made and very shy and timid, I was selected for one of the girl...
    deleted deleted
    4 Responses Mar 13, 2010

    My First Time

    if you read my stories you will find a lot about how i started down this path and how i got to where i am now. my first memories of becoming the sissy i am today started with my sisters dressing me as a bridesmaid as a punishment for being unruly at around the age of 4 or 5...
    sissypolly sissypolly
    41-45, T
    7 Responses Oct 12, 2010

    My Summer At Aunt Betty's House

    This was the first summer that my parents decided to go on vacation without me. They were going to be gone for 4 months and wanted me to stay with my Dads sister and family. I wasn't sure I would like spending my whole summer vacation with Aunt Betty and her two daughters. We...
    wantabgirl wantabgirl
    56-60, M
    4 Responses Oct 6, 2012

    Not Sure

    I'm not sure when I really dressed as a girl for the first time. There were no female clothes even remotely close to size in my house but I started putting makeup on when I was about 7 or 8, and that continued to this day. And I didn't really have any kind of girls wardrobe for...
    deleted deleted
    Jul 13, 2012

    Dress To Go Out

    It was when I was about nineteen over the the years I got my set of pantys and garter belt with a bra or two, and some fish net nylons and regular nylons,but my biggest thing I got was a mini skirt and a top so the next weekend I decided to get dress and drive around and see...
    michellmartinez4 michellmartinez4
    5 Responses Mar 11, 2011

    First Time

    I was 6 years old and had a minor role in a school play about Midas the king for whom everything turned to gold, the day before we were due to perform the play in front of the school one of the lead girls went home sick. My teacher asked for volunteers to play her role but none...
    Jennianne Jennianne
    41-45, T
    3 Responses Nov 27, 2009

    When I First Dresed As A Girl

    Going out? At ten, with mom, to buy a skirt, blouse,slip, stockings, girdle and shoes. Mom had always encouraged me but this was our first time out together. Went first to the dept store, and then to a specialist store for my girdle. I had to try it on even tho I was...
    MaryRoberta MaryRoberta
    66-70, T
    2 Responses Oct 31, 2011

    When I First Dresed As A Girl

    Going out? At ten, with mom, to buy a skirt, blouse,slip, stockings, girdle and shoes. Mom had always encouraged me but this was our first time out together. Went first to the dept store, and then to a specialist store for my girdle. I had to try it on even tho I was...
    MaryRoberta MaryRoberta
    66-70, T
    Oct 31, 2011

    First Time

    It started when I was 10 or 11. I was infatuated by women's lingerie. My sister was 17 & worked on Saturday's as did both my parents. So every Saturday I had the whole house to myself to wear my sister's clothes & parade around like the femmy little sissy that I was! When I...
    saracd4 saracd4
    56-60, T
    8 Responses Jun 30, 2012

    First Time Dressing As A Girl

    I remember when I was 11 or 12 going into my mom's room and taking her bra and panties from her dresser drawer. I took my clothes off and put on her panties.  They felt so soft and comfortable.  Then I put on her bra and adjusted the straps,  She must have known after putting...
    jml2000 jml2000
    61-65, M
    1 Response Dec 6, 2012

    I must have been 8 or 9 at the time.

    The girl who lived next door to us. I was playing hot wheels with her younger brother. When we were dividing the cars I picked the pink trans am. Later she took me into her bedroom and we played in there for a while. Eventually it led to me trying on her Girl Scout uniform, knee...
    deleted deleted
    2 Responses Nov 13, 2015
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