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I Remember The First Time I Was Taken Out Dressed As A Girl

Personal Stories, Advice, and Support 714 People

    It was a Friday night

    and I had just arrived to a hotel in New Orleans. I was with one of my friends that knew i wanted to be a girl and she had been planning to take me out as a girl the whole time. She had brought enough clothes and then some for both of us for the week. The previous week she had...
    Kristen72 Kristen72 18-21, T 7 Responses Feb 18

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    My First Halloween

    My first memmory of being dressed like a girl was at halloween, i was about 4yo and i wanted to go out trick or treating as it was a last minute thing i did not have a costume to wear so my mother said she would borrow one frm my cousin, at that point i was happy, until she came...
    jane1976 jane1976 31-35, T 13 Responses Oct 26, 2013

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    This One Is For My Leah.....

    I am already female, so going out for the first time in a dress was no big deal. For Leah however going out dressed enfemme is a thrill for him. When I first met him two years ago at a drag show he was dressed very fashionably and even trendy for his age. I especially liked the...
    crsdrsr61 crsdrsr61 41-45, F 2 Responses Nov 12, 2012

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    When Daddy Is Gone

    I am among many of those who were little boys during WW II. All of the men, including my father, had gone to war, and the women at home idolized their little boys, above all. As is well known, many of the mothers, who had been left alone, found solace in letting their sons...
    BobbiJo2 BobbiJo2 56-60 1 Response Jan 3, 2013

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    Trip To The Grocery Store

    I spent much of my childhood being raised by my grandmother. My father was in the military, and was a pilot, and was often away. My mother very much liked to just hand me off to my grandmother and let her raise me. I would see my parents often, but spent the substantial...
    ThomasCarroll ThomasCarroll 31-35 1 Response Nov 29, 2013

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    I Do Not Remember The First Time I Was Taken Out Dressed As A Girl

    i do not remember the first time i was taken out dressed as a girl as i had always been dressed as a girl from when i was born. i remember the first time i went out dressed as a boy as it was after two weeks after first starting school the school had sent me home with a letter...
    PoppyAnn PoppyAnn 56-60, T 3 Responses Jun 28, 2011

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    New Neighborhood

    when i was 7 years old, my family decided to move. i don't remember where we lived before then though. now my dad left before my mother knew she was pregnant so... yeah. and i had a twin sister.As we were moved in, i wanted to ride my bike. my mom said it was ok if they have...
    nicole9000 nicole9000 18-21 3 Responses Apr 8, 2013

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    Aunties Little Sissygirl

    I was 10 years old when my aunt decided to put me in dresses at home. She put me ina yellow dress and lace panties with a training bra.maryjane shoes and knee socks.she took me to a salon and had my hair curled and put a bow in my hair.we spent all day at the mall practicing...
    Tracygellar7 Tracygellar7 22-25 13 Responses Oct 14, 2011

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    At 14

    At the age of 14 I was dressed as a girl by my mom for a costume party. I loved every minute of it. Here I was walking into a room full of people I knew wearing a dress and 4 inch heels. I was dressed from the panties up in moms clothes. They actually thought I was a girl just...
    Adam59 Adam59 56-60, M 5 Responses Feb 26, 2013

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    My First Time

    I was ten my first time. I had been dressing for about two years but aside from a few quick forays on the back porch I had never really been out in public. On this day father had some papers for a guy in a nearby town. Normally he would have mailed them, but on this day he...
    deleted deleted 26-30 6 Responses Apr 1, 2012

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    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 Feb 9

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    Shopping Trips With Mom.

    My 2 olders sisters started dressing as a girl when I was 5. I was out and about but didn't really know what was going on at that age. When I was 10 my mother took a real interest and started dressing me as a 10 year old girl. I had just finished school and was out for the summer...
    femboy4u femboy4u 22-25 16 Responses Apr 20, 2011

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    The Dentist

    I doubt this was my first time taken out by mom as a girl ,but it is a time I remember, I now feel free to share and let others know what I did ,it is okay to share. Mom dressed me in a old faded print dress ,it once kinda pink, but it looked aged,I wore hose with a runs in...
    Kristen4 Kristen4 18-21, F 2 Responses May 12, 2012

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    Going Out Dressed Like A Girl Wasn't Necessarily What I Was Planning,

    I was young, probably about 8 or so and I had been playing all day with my sister (10 year old stepsister actually). My father passed away about a year earlier. It didn't seem like a big deal but somehow I let my sister talk me into dressing like her girlfriend to play house...
    kayleew2000 kayleew2000 18-21 18 Responses Mar 25, 2012

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    My Gf 21st Birthday

    the first time i went out dressed as a girl was for my girlfriends 21st birthday we had been dating for just under 2 years.about 2 months after we started dating i told her that i had always wanted to dress in womans clothing and that i had done it a few times when i knew that i...
    outdoors49366 outdoors49366 36-40, M 4 Responses Dec 30, 2011

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    First Time Out Dressed As A Girl

    Well, I finally did it a couple of weeks ago, after seeing an event on Transtastic.com, I got up the courage and mentioned it to my girlfriend. I have never been out of the house dressed up and she dared me to do it. Of course, I didn't need much persuasion and we were soon...
    algina algina 36-40 6 Responses Jun 9, 2013

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    Related Experiences

    On Saturday April %th I am having my first night out dressed as a woman. Going to town with a group of natural girls foe food, show and drinks. just cant wait. Plenty of shopping...
    cperry3105 cperry3105 51-55 1 Response Mar 23

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    well, it used to happen abnormally often, but I guess the earliest times I remember doing it, while awake, was in kindergarten. I was too afraid to ask the teacher where the...
    seminormalhuman seminormalhuman 18-21, M 1 day ago

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    .....I cut myself for the first time about 3 weeks ago.... It stung. I remember the night so clearly. I was depressed because I found out my crush had sex with another girl when I...
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    I remember the first time I took LSD . I was seventeen and had been smoking hash for about six months and the LSD era was starting to catch on in a big way. There was four of us...
    omgspinner omgspinner 61-65, M 4 Responses Apr 4

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    I admit it - I like to cross-dress. Sometimes, I would put something on, and just for a bit of a rush, take a quick walk around the outside of the house (either from the front door...
    KatieTreat KatieTreat 51-55, T 1 Response Mar 28

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    Life is full of surprises, irony and twists, and one night at work I had one in mine. A few years ago after a satisfying Easter dinner with my family, I set off for an overtime...
    Justint2014 Justint2014 31-35, M Mar 24

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    Jessii. God Damn you. The first time I cut, it was for a friend of mine, her name was Jessii. She told me if I cut once with her, she'd stop Cutting for good. I did it and I...
    KOOLKAT446 KOOLKAT446 13-15, F 1 Response Apr 6

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    I was in pre-school, and things were going normally. All of a sudden, the phone rang and the preschool teachers told us that we were all going home early. They didn't tell us why...
    whitemiddleclassteengirl whitemiddleclassteengirl 16-17, F 1 Response Apr 9

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    I live in a house with a bunch of girls(16,18,17, year old sisters and a mom)We were in the car driving to church and my sister spills her soda all over me and it was worse cause I...
    jonathonfalcon jonathonfalcon 16-17, M 1 Response a week ago

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    I was six, and playing with my cars and dolls when my parents turned the TV on to CNN and I saw the buildings being bombed. I thought at first it was a movie, but my mom started...
    allonsyalexa allonsyalexa 18-21, F 6 days ago

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    When I got waxed for the first time, I was nervous and worried about how much it would hurt but I was so curious to how it felt, I had to do it. So I called this salon and made an...
    laud23 laud23 31-35, M 1 Response Apr 6

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    Well what happened was my French ex girlfriend was kissing another girl and I walked in on em...for some reason I laughed
    MixedLesbian MixedLesbian 16-17, F 1 Response Apr 8

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    The first time I had sex was with my best friends older brother one night when I stayed the night over there and she fell asleep. To this day she doesnt know he slept with me on...
    rebelbbygirl rebelbbygirl 18-21, F 1 Response Apr 12

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    I was mistaken for a girl was in a clothing store and decided to try on some different clothes. before you go in they check to see how many item you have, when she was done she...
    olsentrisha olsentrisha 41-45, T 3 Responses 1 day ago

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    I had this friend, we were so close. Lets call him Fred. Also though on the edge of being together for quite some time. I got a new boyfriend, after a few months we were perfect...
    BlooRae BlooRae 16-17, F 4 days ago

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    First off I am a girl. When I was 13 and getting ready for my confirmation my mom bought me my first pantyhose. My older sister showed me how to put them on. I wore pantyhose...
    trojan83 trojan83 26-30, F 4 Responses Apr 2

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    April 5, 2014 I went to the mall by myself to go shopping. I went to Macy's and some other stores. After I got something to eat I was thinking. Should I go in the girl store or not...
    Sarahismygirlname Sarahismygirlname 13-15, T 2 Responses Apr 6

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    I was with my dog T and my step bro E. We both were spending the night at Ts house. They've both gotten drunk before but I haven't. T had a friend pick up a bunch of beer and a...
    Anonymous13brah Anonymous13brah 16-17, M 1 Response Mar 23

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    Girls can be ******** to guys too, it's not always the innocent girl in the relationship getting hurt- guys get hurt all the time but they're not allowed to show it, so i will in...
    Gerald6 Gerald6 18-21, M Mar 23

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    It was about a year ago I think, me and my sister was fighting (as usual) just cuz I wouldn't go outside with her! She told me I should go slit my wrists and die! Then she grabs a...
    InMemoryOfMe InMemoryOfMe 16-17, F Apr 6

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    I remember I was home alone and I was very horny so I decided to go try on a pair of my sisters panties. I've been wearing panties ever since.
    jfc327 jfc327 13-15 5 hrs ago

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    I was 8 and I was desperate to go but I was sleepy so I didn't. That nite I dreamed of me going to the toilet and sitting there and peeing. I guess I really did that but on the bed...
    peepants700 peepants700 16-17, F 5 Responses Mar 24

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    I was 10 and we were at sunfest, at the waterpark. I really needed to go but i didnt want to use the bathrooms so i asked my mom if i could go play in the water she told me ok but...
    LizWasNotHere LizWasNotHere 13-15, F 5 Responses Mar 27

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    when you freak out because you so badly want to remember some songs she always used to play in the car but you can't just pick up the phone and ask her. </3 I just want to...
    Ray1787 Ray1787 18-21, F Mar 23

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    I was with my dad lol. There were crazy kids knocking at the door, I was scared as fukk lol
    vividdreamer97 vividdreamer97 16-17, F Mar 24

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    I think i was in 6th grade and me and my mom got in a huge fight. She went to walk the dog so I sat down int the bathroom crying, and cut a few short lines on my left wrist.
    emmakitti emmakitti 16-17, F Apr 6

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    i was 18 and at a club, it was awsome
    sammie666 sammie666 36-40, M 1 Response 4 days ago

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    :( I was sitting in my first grade classroom, and we were getting ready to watch a movie. The teacher turned the tv on so we could put the movie in and it was on the news channel...
    Belieber4Life Belieber4Life 18-21, F 2 Responses 4 days ago

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    It was a weekend fishing trip to Queens Charlotte Sounds in Marlborough. It must of been about 1969 or 70. My sister was courting an English boyfriend who looked and talked like...
    lafsnack lafsnack 51-55, M 1 Response Mar 21

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    I am a transgendered person who came out to my wife in 2001 year after 20+ years of marriage (actually, I was originally discovered by my wife in the early 1980's, but I spent a...
    Trisha60ts Trisha60ts 61-65, T 2 Responses Apr 6

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    I was a funeral director at the time based in Virginia. Started off a calm morning (suppose to report at work at 2PM) - eating breakfast when 9-11 happened. My work called me...
    daveredding daveredding 36-40, M 1 Response 6 days ago

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    My father was orphaned in WWII. Everyone in his family was killed in the London Blitz except an older sister who was safely away at school. She grew up, got married and had four...
    TandSMichael TandSMichael 51-55, M 3 days ago

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    Been looking into spankings for awhile and didn't know how to get my husband into it, but turns out he knew all about it. So we got out the paddle and it was so great I want it...
    Badgirlfornow Badgirlfornow 26-30, F 11 hrs ago

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    A little while ago, I opened up a package of push pins and a thought came into my mind. Why not just scratch myself with it? I kept scratching and scratching, and on one of the...
    haileybean89 haileybean89 13-15, F 2 Responses 4 hrs ago

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    I was partying because thats my birthday
    Nashes13 Nashes13 22-25, M Mar 24

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    I have recently started cross dressing in what ever clothes I can get from my sisters cupboard, but I though it looked stupid when my pubes were sticking out of these tiny pink...
    Jess967 Jess967 18-21, M 5 Responses Apr 7

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