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I Dressing Boys As Girls

Personal Stories, Advice, and Support 970 People

    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, 2014

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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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    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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    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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    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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    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 1 Response Nov 5, 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 Mar 3, 2013

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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 2 Responses Jul 23, 2014

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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, 2014

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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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    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 2 Responses Jun 17, 2014

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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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    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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    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 6 Responses Feb 15, 2011

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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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    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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    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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    }: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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    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, 2014

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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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    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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    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, 2014

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    aqww aqww 13-15, M 2 Responses 9 hrs ago

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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 4 Responses Jun 19, 2013

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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 8 Responses Jan 3, 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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    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 3 Responses Dec 9, 2013

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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 3 Responses Nov 24, 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, 2014

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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 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, 2014

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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 5 Responses Dec 20, 2013

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    Related Experiences

    I do agree, I think that all boys, at least at some stage of their lives, should be allowed to experience how wonderful wearing cloths made for girls could feel. They should be...
    mizmaid mizmaid 36-40, M 7 Responses Jan 11

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    So I'm going to repeat a post from another EP user, with some observations of my own. She says that /start quote It seems Mother Nature has planted a "Sappho Seed" in all females...
    ron383 ron383 36-40, M 2 Responses 14 hrs ago

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    So I'm going to repeat a post from another EP user, with some observations of my own. She says that /start quote It seems Mother Nature has planted a "Sappho Seed" in all females...
    ron383 ron383 36-40, M 14 hrs ago

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    Aight, I confess to liking both boys and girls. With boys I feel they are in control and with girls I feel I am in more of control. I can only be with a girl emotionally though. I...
    jakethesnake1342 jakethesnake1342 22-25, M 11 hrs ago

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    the way you smile especially, make me melting on the floor.. so please girls, keep that smile on your lips.
    IszRichardson IszRichardson 18-21, F 3 hrs ago

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    My boyfriend smokes but I don't. I get jealous of every girl I see with almost any drug habit. I know how insane it seems, but I still can't shake the jealousy that all these other...
    itsmetheresa itsmetheresa 18-21, F 2 hrs ago

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    Boys are so sexist! They always think that guys are always better than girls in everything but they never actually think about stuff that girls can only do and that's what makes...
    akicupcake9 akicupcake9 13-15, F 1 Response Jan 13

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    Hi my name is April Barbie just give me a yes maybe or no–boys can be just as pretty as girls with all types of girls clothes hair things such as ponytail holders hair barrettes...
    PrincessGirls2448 PrincessGirls2448 46-50, F 12 Responses Jan 16

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    I hate boys they ask for way too much!! Uggh
    BaileyMauto19 BaileyMauto19 18-21, F 4 Responses Jan 1

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    I would like to do a pee holding game with boys and girls. I am about 14 and like to hold my bladder.
    MMarce MMarce 18-21, M 1 Response Jan 3

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    I am tall but weak. I was always quite weak also as a child. My first experience was at school. I was 16 and a girl from the neighborhood who was swimming a lot once teased me by...
    lagavulin lagavulin 31-35, M 2 Responses Jan 5

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    I'm confused. I feel somewhat attracted to boys but for some girls I just feel this attraction towards them. Idk its hard because my parents are very homophobic and think anyone...
    jess965 jess965 13-15, F 3 Responses 6 days ago

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    Any virgin girls need mom to help u loose yr virgininty befour the new year come chat
    lezmummy lezmummy 31-35, F Dec 31, 2014

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    I have long thought about cross dressing. Only recently have I seriously tried it and it sure is exciting. I bought one sexy negligee and G-string. I took some pic's of me and...
    SunsetBreeze SunsetBreeze 56-60, M Dec 28, 2014

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    After my sexual initiation at school by a boy, I avoided any further humiliation by having a girlfriend. I enjoy being with my girlfriends sometimes more than with boys!
    Skjeggstad Skjeggstad 22-25, F 3 Responses Dec 29, 2014

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    I really have come to understand how women can be such teases when they dress provocatively. And I have a confession to make I really enjoy dressing this was in public and watching...
    StrictNewMom StrictNewMom 51-55, T 8 Responses Jan 11

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    Party dresses were a kind of thing that at the time had the allure of forbidden fruit in a gender conforming police state for I was kept apart from my real self, being in some...
    Joanne0chan Joanne0chan 31-35 1 Response Jan 13

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