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I Dressing Boys As Girls

Personal Stories, Advice, and Support 919 People

    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 4 Responses Jun 17

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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 7 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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    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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    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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    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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    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 36 Responses Jul 19, 2012

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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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    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 6 Responses Dec 5, 2012

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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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    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'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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    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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    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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    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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    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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    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 6 Responses Mar 20

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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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    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 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 8 Responses Jan 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 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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    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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    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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    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 26-30, F Mar 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 7 Responses Aug 15, 2012

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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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    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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    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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    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 2 Responses Apr 10, 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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    Related Experiences

    think girls are superior to boys. all girls should put boys through petticoating and femininze them to turn boys into pretty girls.
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 3 Responses Oct 23

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    Sometimes the modern world seems rather topsy turvy to me and especially as it applies to raising children. There is scarcely a day when one doesn't read of a challenge to how...
    Joanne0chan Joanne0chan 31-35 1 Response Oct 14

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    Not all boys necessarily , but in general, I think boys should be able to wear skirts and dresses and have it be fine. Girls wear pantsuits and they're perceived as powerful. Boys...
    laracomn laracomn 16-17, F 18 Responses Oct 18

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    What turns you on most about young girls
    pervlikes pervlikes 36-40, M 2 Responses 4 hrs ago

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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 3 days ago

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    i really do think girls clothes are better than boys as from a male point of view i just look at ladies skirts, dresses, coats, etc and think to myself i want to be wearing them as...
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 4 Responses Oct 3

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    As I've mentioned in my other stories, I've often had girl bullies pin me down. Most of the time this happened, the girl pinning me was bigger then me. But this one time it...
    SmallGuywimp SmallGuywimp 26-30, M Oct 8

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    It is inaccurate to say some girls like bad boys. Broken is more like it. We see through them, they're just like us, good souls; wounded hearts. It doesn't stop at broken boys...
    Darnguyen Darnguyen 22-25, F 4 days ago

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    Lol just this week I've confessed to myself that I might actually like girls. I like both boys and girls though. I've never been with a girl so I'm not sure which one I prefer but...
    LexiK88 LexiK88 16-17, F 3 Responses 4 days ago

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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 20 hrs ago

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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 2 Responses 3 days ago

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    i am a girl born in a boys body as i have always felt i should of been a girl as i have always been interested in girly things like makeup, girls clothes, etc
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Oct 23

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    I'm not gunna lie. But girls do have wider clothes variety:D
    B2ST B2ST 16-17, M 1 Response Oct 4

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    I think other girls are pretty and that they look good and stuff you know but like I like boys
    ZebraUnicorn ZebraUnicorn 13-15, F 2 Responses Oct 9

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    I went to a fancy dress party dressed as Charlie Chaplin. For some reason I loved it, I was just a horny dressing up in mens clothing as i am with dressing up in a slutty fancy...
    AnnieJF AnnieJF 18-21, F 2 Responses Oct 11

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    So I know this is going to sound silly but my cousin is having a halloween party and she wants all the girls to dress up as Monster High characters. I have been looking up most of...
    Janasai Janasai 18-21, F Oct 12

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    Thinking of getting a little dress and panties or a girls Halloween outfit
    Mews4you Mews4you 22-25, M 1 Response Oct 16

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