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I Dressing Boys As Girls

Personal Stories, Advice, and Support 892 People

    Dressing Up Games

    I remember the first time I was dressed as a girl. My sister had a handful of girlfriends around the house...she'd have been about 7 then, and so were her girlfriends. They were playing dressup, and being the younger brother...about 6 then, I wanted to play too. So, all the girls...
    sissifyme sissifyme 46-50, M 7 Responses Feb 15, 2011

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    Mommy Little Girl

    I was raised in a rural area in a female dominated house. We were poor and my mother found it easier to dress me in girls castoff clothing than buying me boys cloths. In order for it to work she also let my hair grow so that I looked more like a girl. I loved it and as I had...
    SharronT SharronT 66-70 4 Responses Sep 13, 2013

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    Mothers new hairstyle part 1 A little

    backstory I'm an 7 year old boy named sam. Since my mother is an extremely experienced hair stylist and beautician, she has always given me my haircuts all my life. Most of the time though lately, I've been just getting my hair cut down pretty short from her because summer in...
    Thegirlinside88 Thegirlinside88 31-35, M 2 Responses Mar 5

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    Dressing Up My Little Cousin.

    one day i was alone in the house babysitting my 10 year old cousin,his name is lee and he always got bored really easy.we had already tried playing 2 board games,tried 6 different games on my playstation and played hide and seek. i found him after our last game hiding in my...
    cdBethany cdBethany 22-25, M 1 Response Apr 10, 2013

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    Dress Me Up!

    Today I decided I want to try to crossdress. However, Im god awful at putting on makeup and deciding what clothes to wear. Im really not sure how far I want to go with all this but in order to make it all work I will most likely need a girl to help me out along the way. Im open...
    poppacherry poppacherry 18-21, M 1 Response Mar 3, 2013

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    Where To Get High Quality Clothes Online At Best Price?

    I googled to buy dress online and came across FlowerGirlDressForLess . Here I got myself a pearly white dress with pink organza sash with 70% discount for sell out price! The company claims that they will give highest quality product at guaranteed low price! There are other high...
    Jessigomes Jessigomes 26-30, F Nov 5, 2013

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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 3 Responses Jun 19, 2013

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    Ok so I don't get off work

    for another week but my Gf alrdy sent me pics of my Christmas present :D she got to be the best Gf ever. She bought me a beautiful colorful panty along with another pink panty, a night gown and a lot of makeup! God I can't wait to get off and I love her so much and she sure...
    boattrash boattrash 22-25, M 2 Responses Dec 9, 2013

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    What did i get myself into?

    part 1 Fiction My mother always wanted a girl, instead she got boys. I was the only boy left from her new marriage and i was probably her last child. All she ever talked about as I grew up was that she wanted a girl and she would have named her Katie. Then on one unusual day...
    Thegirlinside88 Thegirlinside88 31-35, M 2 Responses Dec 20, 2013

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    To Live Freely

    I wholehearted believe boys and men should wear or at least be allowed to wear dresses and or skirts. Since World War II women have had the privelege of dressing in mens clothing and girls have now adopted wearing mens/boys underwear as well (Boxers). Yet we as males are held...
    Melodie13 Melodie13 61-65, M 7 Responses Dec 30, 2010

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    Mummy's Girl

    I remember coming home from school to find that all of my wardrobe had been thrown out and replaced with girls clothes, a majority of which were uniforms. My mother even made me join the girl guides and went even as far as joining the majorette troop.....but i loved it!, far...
    Netballer Netballer 22-25 10 Responses Jan 3, 2012

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    A Personal Story Of Friend Dressing Her Little Brother.

    My friend HAD a little brother who WAS a household pest. He would never find anyway to entertain himself ,instead he made a pest of himself , always annoying a household member. He didn't play with his video games, or his skateboard , every toy he owned gathered dust . At...
    MissPenny MissPenny 18-21, F 7 Responses Dec 5, 2012

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    How It Started

    When I was young around 5-8 can't quite remember but my cousin used to babysit me and my 2 sisters. One day she went get my step sisters princess dress and made me go in the bathroom and put it on. She got a laugh from that. I loved it since it was a first time experience as a...
    boattrash boattrash 22-25, M 2 Responses Nov 24, 2013

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    Cedar Point

    OKSo mom wants me to pretend to be a girl the whole time we are gone to Cedar Point.So Mom gave me this after I got up from my nap.She wants me to re-write it in my own handwriting and give it to her tomorrow night right before bed:Dear Mommy,I love you.I want to ask you...
    14yobabyboy 14yobabyboy 22-25, M Aug 28, 2013

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    AgeMeet.com is the #1 Age Gap Dating Site

    for younger women older men dating . It is Free to post & browse 550,000+ active members. We have been in the online dating business for over 11 years and has achieved tremendous success bringing younger women and older men together! younger women looking for older men mainly...
    kellycc11 kellycc11 22-25, F Mar 7

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    Well I know it's really a kilt

    but I'll bet this little boy is enjoying feeling like one of the girls.
    silkydrawers silkydrawers 46-50 5 Responses Mar 10

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    What Would It Have Been Like?

    If I had been forced to dress in feminine garments as a boy, what would it have been like? Possibly I was to an extent. There was a sweater that had been my older sister's, which I wore when she outgrew it. I also seem to remember wearing some of my sister's panties after she...
    hollywoodlegs hollywoodlegs 56-60, M 2 Responses Nov 9, 2012

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    In The 1800'S It Was The Norm.

    I read that in the 1800's it was common to dress boys just like girls until the age of 5 or 6.I found this picture of FDR in a dressDo you think this practice created more crossdresser back in the day? I know if I was dressed like that when I was young you never would have...
    silkydrawers silkydrawers 46-50 2 Responses Jun 3, 2013

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    My First Time Mother Dressed Me As A Girl

    My 8th birthday was the first time mother completely dressed me, and although it was so long ago I do remember my first dress was a light blue party dress. Being that I was young and challenged, with Cerebral Palsy that I had since birth, mom usually got me dressed. That birthday...
    betty3100 betty3100 51-55, T 13 Responses Feb 18, 2011

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    What did I get myself into?

    Part 2 Fiction On the way home with my mother, I was really nervous. I tried taking my mind off of it, but every time my mother took a turn with the car, I could hear my girly wardrobe rolling and rustling in the back of the car. On the way, i also noticed my mother was driving...
    Thegirlinside88 Thegirlinside88 31-35, M 6 Responses Dec 20, 2013

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    The beauty salon Part 1 My name is Sam

    and I'm a 7 year old boy who's suppose to get a haircut today. Right now, my mother is driving me to the beauty salon and I'm very excited. See, my mother usually gives me my haircuts herself, but they never turn out that great to be honest. So for today, she said she'd treat me...
    Thegirlinside88 Thegirlinside88 31-35, M 6 Responses Mar 12

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    Boys Dressed As Girls

    I'm all for dressing boys as girls as there are many parents who only dress their girs in trousers/jeans and never a skirt/dress even for school
    xdpaul xdpaul 56-60, M 4 Responses Jul 10, 2011

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    Four Years Old, Makeup, Hair And A Cigarette

    I was a four-year-old boy, and my mom's friends had always commented that I had pretty red lips like a girl. My mom had always wanted a girl to dress up. One night, her friend Caroline came over to give my mom a home perm. Caroline was a hairdresser and a chainsmoker, and seemed...
    Onetruenutcase Onetruenutcase 51-55, M 2 Responses Dec 22, 2012

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    I'd like to hear what you like about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 1 Response Feb 9

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    What did I get myself into?

    Part 4 Fiction On the way home in the car with my mother, I was truly at peace with myself. I mean everything just felt so right to me. Even though I was a boy when the day began, I truly feel like a girl at heart now. I don't know why I feel so good, but I just do. Maybe it's...
    Thegirlinside88 Thegirlinside88 31-35, M 7 Responses Jan 7

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    I Dressed Mi Nephew Like A Proper Lady For The Summer

    My nephew had 12 years old, and one summer, he made a big mistake with her cousin (my daughter) to up her skirt infront of people in the mall; at this same time I wanted to apply him a petticoat punishment; with the help of my daughter and my sister, (his mother) we went to...
    rosepro rosepro 36-40 6 Responses Aug 15, 2012

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    Like Mommy Or Like Daddy?

    A wedding we were invited to attend when I was nine years old my mother sat down with me one afternoon and told me we were attending.  This was over a year since mother started to feminize me, and the first formal event that I would be going to.  She told me that I had a...
    betty3100 betty3100 51-55, T 9 Responses Mar 6, 2011

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    The Beauty Salon Part 2 Watching my mother

    running her hands through my hair for a few seconds, one of the little girls smiled and asked my mother, "are you getting a perm too miss?" Right away from hearing the girls question, my mother leaned over my chair, began hugging my body very tightly, and estatically said back...
    Thegirlinside88 Thegirlinside88 31-35, M 5 Responses Mar 20

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    What did I get myself into?

    part 3 Fiction After being dolled up and put through one heck of a few hours, my mother decided to make us both lunch before our trip back to the mall. She said, "your going to need your energy for what I have in store for you!" I looked at her with a puzzled look, it was...
    Thegirlinside88 Thegirlinside88 31-35, M 6 Responses Dec 28, 2013

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    Mothers new hairstyle part 1(with pictures

    now)A little backstoryI'm an 7 year old boy named sam. Since my mother is an extremely experienced hair stylist and beautician, she has always given me my haircuts all my life. Most of the time though lately, I've been just getting my hair cut down pretty short from her because...
    Thegirlinside88 Thegirlinside88 31-35, M 3 Responses Jun 17

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    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21 Jul 23

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    My Sweet Toby

    I dress my boy in a lot of his sister's outgrown clothes. He actually has come to feel very comfortable in girl's clothing and prefers pretty girl's undies to jockey shorts. It started when I simply used his sister's baby things for him. It seemed a waste to spend so much...
    Lanainluv Lanainluv 26-30, F 32 Responses Jul 19, 2012

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    My Son Or Now Daughter

    We have a 7 yo son and 2 daughters 14 and 9. My son always loved touching the panties that the girls would be wearing. It wouldn't matter if they were cotton or nylon. Briefs or bikini type ones. He just loved the touch of them. Not to long ago he was seen wearing one of their...
    deleted deleted 26-30 4 Responses Aug 14, 2013

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    Related Experiences

    Ever since I was 12 or 13 I've been cross dressing in secret. My mother caught me once when I was about 13 or 14. She was okay with it and asked me if I liked cross dressing. I...
    masspink masspink 18-21, M 3 Responses Jul 2

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    Ever since I was a little girl I was always attracted to other girls. When I was little I'd play house and I would offer to be the dad just so I could have a "Wife". As I grew up I...
    TheGirlFromJupiter TheGirlFromJupiter 18-21, F 4 Responses Jul 4

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    I go to an all girls school and there's an all boys school across the road but we hardly ever do anything with them. All my guy friends go to the boys school and lets not lie; they...
    untitled360 untitled360 13-15, F 1 Response Jul 10

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    I went to London yesterday to an theme park where a lot of people around my age are there. At home and school, I don't really get any attention from boys. It's not because they...
    SilkyDoughnut SilkyDoughnut 16-17, F 3 days ago

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    Me too. Some girls mimic boys. But most girls prove they are the better of the two genders.
    converted converted 46-50, M Jul 1

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    i was about twelve when I realized that I had an attraction to both girls and boys. i had a crush on my bestfriend, how awkward right? well, a couple months ago I told her she was...
    winksviolently winksviolently 13-15, F 1 Response Jul 7

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    I have such fond memories of childhood. I was the last of four children, 14 years behind my oldest sister and the only boy in the family. I have only scant memories of a father...
    Varience Varience 70+, M 1 Response Jul 9

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    I know this sounds stupid to most of people but I've tried to find a boy that I like. I can be like wow if I see a guy that looks good in my eyes and if I notice that he likes me I...
    realandtrue realandtrue 18-21, F 3 Responses a week ago

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    I am a lesbian. Where I live you really can't speak about it. I've known I liked girls for as long as I could remember and I remember when my female friends would talk about boys...
    Alexandra987 Alexandra987 18-21 2 Responses Jul 7

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    I like boys and I like girls. I have an amazing boyfriend whom I love with all my heart. I couldn't imagine spending my life with someone else. But I also love girls. I am really...
    Nemessie Nemessie 22-25, F 3 Responses Jul 21

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    I'm bi but I prefer girls waaaay more than I do guys. I can remember having small crushes on girls from as young as around seven years old I just didn't know what I was feeling. I...
    gardengirl17 gardengirl17 22-25, F 2 Responses 6 days ago

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    Huh. You would think that there would me a lot more girls in this group. I look down the stories briefly and it's only boys and transgenders. Did I not notice that this was a...
    InternationalDarkness InternationalDarkness 13-15, F 2 Responses 6 days ago

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    When I was 8, I was staying at my sister Amory and her friend Diana's house. My sister thought that for ***** and giggles, she have me try on a girls outfit. First, she dressed me...
    SamHarris SamHarris 22-25, M 1 Response Jul 13

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    I used to get teased by girls because I was different. I think that girls who liked boys strictly had phobias thinking if I made them feel funny they were that way. Nope! I'm bi...
    exoticlotus21 exoticlotus21 26-30, F 4 Responses Jul 16

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    Just call me your modern day Audrey Hepburn. I love perfume, putting on lipstick, and eyeliner. From the little black dress to floral flowing dresses. I love to loose for the...
    MissingBoston MissingBoston 26-30, F 5 Responses 3 days ago

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    All my life I thought dating boys was the only dating there was.. So that's exactly what I did. The couple relationships I had were difficult, slow, and would end the moment he...
    JacieMarie JacieMarie 16-17, F 5 Responses Jul 6

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    Aye I'm bi and looking for any girls on snaochat I'm 18 add me at horny_biguy ;)
    Hornybiguy96 Hornybiguy96 18-21, M 10 hrs ago

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    Why do guys want to message me all the time I would like it girls to would message me to
    bicurious68 bicurious68 18-21, F 10 hrs ago