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

Personal Stories, Advice, and Support 711 People

    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 3 Responses Nov 12, 2012

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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 1 Response May 12, 2012

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    At My Grandma's House

    I was only twelve at the time when my grandmother became ill. My mother had packed my suitcase and when I came home from school I was told we were going to my grandmothers. She lived out of state in a rural area as she did not like the city life. Soon we were driving to her...
    Melodie13 Melodie13 61-65, M 9 Responses Dec 7, 2010

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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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    As A Child

    even always being told they wish i had died and my twin had lived. i do not remember being dress many times as a girl , but then i do not remeber a lot of earler childhood have seen pictures of me dress as a girl when very little and have seen a trick or treating picture of me...
    rickibrat2 rickibrat2 61-65, M 2 Responses Dec 15, 2010

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    I Learned From Day One To Hate It

    but then again most would if you got the idea you were only be dressed as a girl for some one to use as a girl
    rickibrat2 rickibrat2 61-65, M May 13, 2012

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    The Sweet Memmories

    OH those sweetmemmories I have of the smock type little cotton dresses and the excitement of having on those sweet little girlie panties are non to compare when i had to fallow along behind grandma when we went to get the cows from the pasture, or go with my wagon to get fire...
    karriefalon karriefalon 46-50, T Nov 27, 2011

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    Halloween

    my first time actually out and about as a girl was on Halloween. I decided I wanted to be a belly dancer. ask and I shall receive so thats what I went as to my friends party. at first no one recognized me, untill I spoke of course. well I had lots of complements on my costume and...
    loveme368 loveme368 18-21, T 3 Responses Jul 18, 2011

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    18 Years Old ...

    Although I had been frequenting my mum's clothes and stuff when I was younger, as detailed in other stories, I had not tried makeup or 'came out' as a tranny when I was 15, I spent my first few years just dressed at home....not having the guts to go out..... Come 18 and mum was...
    TVCassandraSlut TVCassandraSlut 26-30, T 1 Response May 27, 2013

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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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    First Time

    I do not know if this counts, my first time of being taken out dressed as a girl was last march at the age of 53 to have some photos taken of me dressed in female attire
    xdpaul xdpaul 56-60, M Jun 12, 2011

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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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    The Time I Enjoyed Best

    it started in 8 th grade when the person i loved want to go to schools as she had been born not how she had been forced to live in the past we were sitting in a big resteraunt eatting dinner and talking about summer coming up in just a week and we knew it was going to be busy...
    rickibrat2 rickibrat2 61-65, M May 13, 2012

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    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 11 Responses Feb 18

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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 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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    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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    Guess This Counts

    Do not know if this counts as being dressed as a girl by someone but here is my story It was the first day of summer school in 1960, and it had been an interesting summer so far and we had both grown a lot over the last month. ( a doctor made choices at her birth that would have...
    rickibrat2 rickibrat2 61-65, M 1 Response Dec 31, 2010

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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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    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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    Halloween '09

    The first and last time I went out as a girl was Halloween of 09. It was my last Halloween before boot camp and my friends had always teased me that I should dress like a girl because when we would play D&D (Dungeons&Dragons) I would often play female characters. So that...
    CDX21 CDX21 22-25, M 6 Responses May 26, 2011

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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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    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 12 Responses Oct 14, 2011

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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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    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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    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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    Related Experiences

    my "first time" is just my first time making out, but it was with a 17 year old & I'm only 14 & i don't know I just wished it was with someone I actually loved.
    maddielovee maddielovee 13-15, F 2 Responses Jul 6

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    I was 19 and had never even kissed a girl properly before, though I had had one or two one off incidents of breast touching etc that lead nowhere. I was also born with medical...
    RogerWaters1979 RogerWaters1979 31-35, M 1 Response Jul 6

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    When I was thirteen, my sister who was 25 was pretty much in command of the house as our parents had died. We were playing baseball and we made a bet: whoever won would have to do...
    Raxicorico1234 Raxicorico1234 22-25, M 2 Responses Jun 25

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    Ok so this happened in January last year my friend had just turned 16 so me him and our friends decided to have a few drinks, I was not wanting to as I had never tried Alcohol...
    michaelsshawn121 michaelsshawn121 18-21, M Jul 5

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    I went out 2 nights ago for work drinks except after 3 wine glasses I was completely out of it. I awoke at 5 am in a strangers bed realizing that I had blacked out, I barely still...
    Silvertwilight Silvertwilight 22-25, F 3 Responses 6 days ago

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    This happened last year. It was really hot and all we had was a kiddie pool. I filled it up with water and put on my swimsuit and sat in it for a while. After what seemed like a...
    fshlor fshlor 18-21, M 2 days ago

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    I was about 8 years old when I put on pantyhose for the first time. I remember my sister was using some of her torn pantyhose to make dolls and I took a pair and tried them on. It...
    natfranny natfranny 22-25 2 Responses Jul 11

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    I remember having ******* as early as six but I knew what they were before that even I just kind of knew "the weird feeling" though I didn't know how to cause it until I turned ten...
    sirsnoopy7 sirsnoopy7 22-25, M Jul 12

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    I was high on weed during school. A friend gave me a waterbottle full of vodka. I chugged some of it and I got drunk for the first time. It feels so much different than being high...
    vegasboi vegasboi 16-17, M 1 Response 2 days ago

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    I got drunk on vodka. First time ever that I got drunk. I ended up puking too.
    zacktr zacktr 41-45, M 2 Responses Jul 6

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    My first kiss was a french kiss. 😝 It happend to be in a car. I was high on coke. Though i never had any practise of kissing but i just copied whatever he did. Haha. And it...
    Xyanii Xyanii 22-25, F 1 Response 1 day ago

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    Well I have crushes all the time but have actually fall in love only twice. So the story of my first love goes like this: I just started high school, first time away from home (I...
    HannibalQ HannibalQ 16-17, F Jun 24

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    Well I have crushes all the time but have actually fall in love only twice. So the story of my first love goes like this: I just started high school, first time away from home (I...
    HannibalQ HannibalQ 16-17, F Jun 24

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    So I'm 16 I've been with this guy for about 2 years nd he's older than me nd we had sex about many times by now (10-20) but the thing is I find it still soooooooooooooooo painful...
    kungfuf kungfuf 16-17, F 2 Responses Jun 27

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    I really do like this girl, she knows that I like her. She likes someone else and I want to ask her out to somewhere. I recently started liking this girl. I liked her friend before...
    MainMan1999 MainMan1999 13-15, M Jul 2

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    I am one of the happiest people right now, after years of not dating or flirting or anything but non emotional flings, I have found a guy who is actually interested in me, he even...
    eviecain eviecain 18-21, F 2 Responses Jul 12

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    I got paddled for the first time since summer break!!! Today man it hurt
    brandonpatrick brandonpatrick 13-15, M 1 day ago

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    Well okay ! Now that i have your attention!! I guess the reason that im writing this. is to get some insight from other girls . Like other New Cds, i had this tremendous rush of...
    Mindi3107 Mindi3107 26-30 1 Response Jun 28

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    It's funny, how innocent you are growing up and then you get to a point, around 13, where all the ideas and good memories you had stop meaning anything and the realities of life...
    Canonomousjay Canonomousjay 18-21, M 1 Response Jun 28

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    When I was young my mom made me wait in the car while she got an abortion. I'm pretty sure this happened. I didn't put it together as a child but looking back it makes sense. As...
    poopoofacecharlie poopoofacecharlie 26-30, M Jul 5

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    Well I was trying to go with a girl last year, I told my good friend everything about her. After a while, I introduced my friend to that girl. After talking with her for 4 months I...
    WillsWill WillsWill 16-17, M 3 Responses Jul 10

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    My first marriage had ended and I had become close friends with a female friend. Nothing had happened between us, but I remember going away on holiday and feeling like part of me...
    Curiousboy007 Curiousboy007 36-40, M Jul 10

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    So my aunt smokes and i was with her and she asked me to go in her purse and get money for BK because we got diet cokes. As i was looking i found some cigarettes and i gave her the...
    Sealover22 Sealover22 16-17, F 2 Responses Jul 9

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    We moved to Scotland when I was 13 from England .I was somewhat of a rebel n have recieved cane over bottom previously. But scotland was a whole ne ball game...the tawse. I...
    thegaychef thegaychef 51-55, M 5 Responses a week ago