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I Dressing Boys As Girls

Personal Stories, Advice, and Support 896 People

    I Want A Girl To Do This To Me

    I want a girl to dress me like a girl and have fun with me. I can never seem to find anyone to do it for me. This is something I really want to do. Can anyone help me?
    deleted deleted 26-30 1 Response Feb 22, 2011

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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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    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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    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 12 Responses Feb 18, 2011

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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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    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 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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    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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    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 1 Response Mar 5

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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 10 Responses Mar 6, 2011

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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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    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 4 Responses Dec 20, 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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    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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    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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    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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    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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    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, T 1 Response Jul 23

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    }:o)

    I loved dressing up as a child and I love dressing up now. Not much has changed. I love waring pretty things. Kisses Dennis / Denise
    deleted deleted 26-30 1 Response Dec 24, 2010

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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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    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 3 Responses Sep 13, 2013

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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 5 Responses Dec 28, 2013

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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 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 28 Responses Jul 19, 2012

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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 5 Responses Aug 15, 2012

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    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 5 Responses Feb 15, 2011

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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 7 Responses Jan 3, 2012

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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 Mar 3, 2013

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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 6 Responses Jan 7

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    Related Experiences

    the time my friend Freddie became a girl part 1 I leaped out the other side of the table and ran for my life, I heard the girls shouting at each other behind me in unison ?You let...
    Jaitheboy Jaitheboy 13-15, T 2 hrs ago

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    the time my friend Freddie became a girl part 4 ?Great! Some boy shoes.? I nodded excitedly, she grinned back at me and left the room to get them. While she was gone, I gave the...
    Jaitheboy Jaitheboy 13-15, T 2 hrs ago

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    the time my friend Freddie became a girl part 2 If she saw what I could see in the mirror, then we were going to be fine. And I was right. As soon as she entered the room, a wide...
    Jaitheboy Jaitheboy 13-15, T 2 hrs ago

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    The time my friend Freddie became a girl part 5 the end of chapter 1 ?This sports bra makes it look like your boobies are starting to grow, girls your age wear these.? I nodded...
    Jaitheboy Jaitheboy 13-15, T 2 hrs ago

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    Recently I've discovered I really really love boys younger than me..... especially if they are a girly boy or a sissy ^-^ so adorable <3
    TheCasualChick TheCasualChick 18-21, F 2 Responses 3 hrs ago

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    Dressing as a girl meant wearing dresses and skirts and all girls underclothing. Today putting on a pair of pants and a T shirt I can say I dress like a girl. Because girls have it...
    Adam59 Adam59 56-60, M 1 day ago

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    I was shopping yesterday and I was bursting for a p**. This happens quite a lot when I'm shopping because I hate using public toilets. I just keep shopping... and shopping. I've p...
    Lin1293 Lin1293 18-21, F 12 Responses Nov 15

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    Women goes through lots of tough times. In my country, boys have to go for national service but girls don't and boys are like, ITS NOT FAIR! Let me tell you boys,95% of what...
    MayDiana MayDiana 16-17, F 2 Responses Nov 5

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    My girlfriend is making me fatter- I've only been with my girlfriend for six months but she's already made me so much bigger. I weigh 238 pounds now and before I met her I was 150...
    breeannbelly breeannbelly 18-21, F 1 Response Oct 27

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    This started when my brother was around 4 years old and I was around 8. One day, after school and it was nasty outside, I decided that I wanted to play house and pretend I was my...
    titelips titelips 31-35, F 6 Responses Nov 17

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    I'm a gymnast and if you know anything about it you know that boys and girls do different apparatuses. (apparati?) Our gymnastics is based on grace and elegance while the guys...
    nothingnobodynowhere nothingnobodynowhere 26-30, F 4 Responses Nov 10

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    I'm a gymnast and if you know anything about it you know that boys and girls do different apparatuses. (apparati?) Our gymnastics is based on grace and elegance while the guys...
    nothingnobodynowhere nothingnobodynowhere 26-30, F Nov 10

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    Without a doubt. They are softer than med clothes and fit me better. Why should I be stuck with heavy rough clothes? So if I want the softer clothes and need to wear women's...
    Adam59 Adam59 56-60, M 2 Responses Nov 18

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    Us girls got better clothes then boys. Women we got better clothes then men
    lorrena19 lorrena19 18-21, F 1 Response Nov 18

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    It bothers me a little when girls say rude things about all other girls and try to disassociate themselves with the female gender. Most of the girls I've known that say they mostly...
    anonymoussouthernbabe anonymoussouthernbabe 16-17, F Oct 30

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    I will never ever be with a man ever. Girls are so much softer to touch, cuddle and kiss. I can connect with girls on levels that would never be able to with a guy
    romanalanski romanalanski 18-21, F 1 Response Oct 27

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    Is that really bad? I mean I flirt with girls for appearances (I'm gay btw) but I don't really have any good friends who are girls. Apparently most gay guys have girl friends, but...
    smikey00 smikey00 13-15, M 2 Responses Oct 31

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    Well today is my birthday and I got exactly what I wanted....some crazy hot and passionate birthday sex from my girlfriend. We have been dating for a month (officially) and after...
    atheGAYlouise atheGAYlouise 22-25, F 5 Responses 6 hrs ago

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