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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,236 People

    I'm wearing a dress, heels,

    wig, and jewelry, and I enjoy it. The next step is to explore some makeup to transform my face.
    mistypink mistypink 41-45, T 6 Responses Jun 20, 2014

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    I Like To Wear Womans Clothes

    now that my wife left me because of me wearing womans clothes i an wear what I want when i want. i have not yet had the courage to venture out in public yet. maybe some day?
    billylee60 billylee60 61-65, M 3 Responses Jun 22, 2010

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    I Like To Dress Like A Woman

    Im 16 and i love to put on panties and a bra and then have the bra wrap around my chest and the feeling of starps on my shoulders, then i love to wear pantyhose over my panties because it feels good, i then love to put on a dress and high heels and go walk around the backyard or...
    addguy3455 addguy3455 18-21, M Oct 9, 2011

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    A Good Find

    I found this wonderful poem today, I thought I would share the final part which I felt was the most poignant for my son and many of you. The poem was written by Kimberly Hilliker. If nurture naturally embraced you, have gratitude. Be joyful in the acceptance of you and those...
    Cute30sMom Cute30sMom 31-35, F 5 Responses Jan 21, 2013

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    After All, It Is Really Me!

    All my life I have know I was a girl. A woman! Despite my birth defect. When I was young I experienced much, most of my younger life as a girl. Had a boyfriend and all. I had a supportive Mom and friends who gathered around me and protected me cause the times were not the best...
    Josie06 Josie06 56-60, F 2 Responses Jan 16, 2012

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    deleted deleted 26-30 2 Responses May 3

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    You Can Say That But

    I'm not a woman but I really enjoy wearing dresses and skirts I love the look and the comforted of them to me it's a simple and easy way of dressing there are the clothes I like to wear not that I feel or try to look like a woman but it makes feel like myself to me and I'm very...
    notech64 notech64 41-45, M 2 Responses Apr 4, 2011

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    Advice For A Son, (2) Continued.

    First of all I want to thank each of my new friends who were so generous as to provide your ideas and your heart felt assistance with the issues related to my son. Each of you had something important to say and I deeply appreciate your efforts. I thought I would catch you gals up...
    Cute30sMom Cute30sMom 31-35, F 14 Responses Jan 10, 2013

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    I saw a post where they were talking about how

    they hide the bump from showing while wearing female clothes and I want to know how you keep it tucked or hidden and anyone have any tips to help hide 5 o'clock shadow my facial grows fast and dark and when I shave you can see a 5 o'clock shadow I would appreciate any advice...
    raider4421 raider4421 26-30, M 3 Responses Mar 30, 2014

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    SO, in celebration of my new acquisition,

    and the tokens I got for a bit more photo slots, I got myself in full attire...
    Automx Automx 26-30, M 11 Responses Mar 28

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    Advice For A Son, (3) Next Chapter

    For those of you who are following my son and I on this journey, I have a small update. Yesterday I went shopping while he was in school and I purchased some new clothes with the intention of just a little trickery but all in the effort of helping my son come to terms with his...
    Cute30sMom Cute30sMom 31-35, F 9 Responses Jan 11, 2013

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    I Share My Feelings

    I share my feelings with you here. I am not working currently, and that makes paying the bills a little difficult (to say the least) A couple years ago I started a blog, using word press, thinking I was going to make money with it. Then I saw the websites of other...
    mslade mslade 61-65, M 2 Responses Sep 12, 2013

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    Why Tranquilise When One Can Accessorise..............

    It's true....I am nearly the third gender. The battle is lodt and the gender is ambiguous. I'm male and I live as a male and I have no hang ups about my maleness nut I diverge from total mascukinity and always have. I just accept it now. I do find comfort in wearing female...
    MorphAble MorphAble 41-45, M Oct 18, 2011

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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 2013

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    I Like To Dress Like A Woman

    I like to dress like a woman.. because it's fun and the clothes are comfortable   no other reasons
    aquarius3 aquarius3 61-65 1 Response Jan 10, 2012

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    Wedding Dress

    I was recently by a Bridal shop and was in there just looking at the dresses. They have aisles up near the front and you had to go through aisles of dresses just to get to the washroom. They get you to take off your shoes, so I was in socks, no jacket, walking through this aisle...
    deleted deleted 26-30 1 Response Mar 28, 2013

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    Advice For A Son (6) Confession

    Ok, time to update my loyal friends on the past couple weeks. I have been pretty busy and haven’t had much time to write so I hope to catch everyone up with this. My son has definitely become more and more comfortable in his new routines and to some degree, I guess I have too...
    Cute30sMom Cute30sMom 31-35, F 28 Responses Jan 31, 2013

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    My Life

    i would say i love to dress as a female. lets face it they have a much bigger chose of clothing. feel like flirting a nice top and short skirt will work want to be elegant long satiny dress off to play jeans or shorts and t shirt. as a man you get pants only
    spaz1177 spaz1177 46-50, T Jul 7, 2013

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    Like A Real Woman

    I don't just like to dress like a woman, I love it. But I mean dress like a real woman rather than a disco bunny or drag queen and I think there is a difference. There are men who like to dress in the clothes as a woman and there is nothing wrong with that, then there are those...
    wetrev wetrev 46-50, M 2 Responses Apr 3, 2013

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    I have always loved dressing like a woman

    but my parents always told me it was bad. Ever since I was young I would hide and dress as a girl and would try to be alone to dress as one. I'm not slutty but I do fantasize lol and I have had my share of experiences but all I have to say is that it feels good to know that...
    deleted deleted 26-30 2 Responses Apr 23

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    How it all started? One of my oldest memories,

    on preschool, so I must have been like 5, in class we coloured and cut out some paper dolls, one male, one female, and some separte paper pieces for clothes too, a dress for the girl, shirt and jeans for the guy. At school I did the "proper" thing and dressed them in that order...
    Automx Automx 26-30, M Apr 17

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    How Much

    The question is: How much do I like dressing as a woman? Well, how does one measure such a thing? By the amount of time dressed, by the number of days dressed, by the number of years as a CD, by the "passibility" of one's dressing? None of these quite works because anything...
    DonnaSt DonnaSt 66-70, M 3 Responses Dec 26, 2011

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    Source Of Happiness

    Dress like a woman, than go outside, is one of the greatest thing. Few days ago, I needed to look like a normal, man, so I forced myself into some of my remaining mens clothes. Ouch, it was terrible. Next day: only womens clothes, such a blessing, more comfortable, and I feel...
    VivienXX VivienXX 26-30, T 2 Responses Sep 13, 2010

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    Advice For A Son (4) New Beginnings

    For those of you who are keeping up with the events and struggles of my son and this incredibly complex journey we are on, I thought I would provide for you a narrative of how he is doing and the directions I am taking to mother him. When I last reported to you, he had accepted...
    Cute30sMom Cute30sMom 31-35, F 19 Responses Jan 15, 2013

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    Advice For A Son

    I hope you don't mind if I ask for a little advice here. But this seems like a great place to learn. I am a mid 30's mom, living in the south, married to a southern rugged red-neck, deer hunting type of guy who travels for his profession. Our son, a 12 year old who is quite...
    Cute30sMom Cute30sMom 31-35, F 54 Responses Jan 7, 2013

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    Advice For A Son (5) Update

    For those of you who have invested in my son through your unselfish contributions of love and advice, I thought I would give you an update on how he is doing.   I think I last left you with he and I having a discussion about keeping his interests between him and I for now and...
    Cute30sMom Cute30sMom 31-35, F 16 Responses Jan 22, 2013

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    I Love Dresses

    I have been obsessed with dresses since I was a little boy I was about six years old. My first dress was a short little yellow sundress with matching panties that I found in the attic. It was one of my sisters old toddler dresses. The dress itself was quite short and the panties...
    tammynicolesmith tammynicolesmith 56-60, T 7 Responses Feb 5, 2013

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    Related Experiences

    I remember being 14 years old, hearing about those "nasty" women who homewreck married relationships- thinking, "ugh! How disgusting! Don't they have feelings or emotions? How...
    RedShootingStar RedShootingStar 18-21, F 6 mins ago

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    i sometimes dress in women s clothing i have had the pleasure of being a woman's' sissy
    bytchboi bytchboi 51-55, M 1 hr ago

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    There's nothing like a heavy bottomed woman on top who knows how to use her hips and bottom to slap down into me and pull all that seed out!
    WarmMilk4Me WarmMilk4Me 36-40, M 1 hr ago

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    I've driven down a really quite road at night bout 2 miles down I pulled over got out to get my cloths from the boot as I finished getting dressed a cop car driven past. I was...
    mybuttcrack mybuttcrack 22-25, M 3 hrs ago

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    Terror on Extension 29 Thirty-One - Eileen Duke From bad to worse. Absolutely the worst day of my young life. Daddy didn't see it, but because I was so late and the school was...
    MaryJanine MaryJanine 56-60, F 4 hrs ago

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    I was stuck in traffic yesterday and so I decided to have some fun with the truck driver next to me... I wasn't wearing underwear to begin with so all I had to do was hike up the...
    Ladybugx Ladybugx 26-30, F 3 Responses 7 hrs ago

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    Im 17 and im with my gf for 8 months she knows i have a strong girly side she knows i like to wear dresses and have my nails painted which she paints them and also puts me in her...
    Lukexlewis Lukexlewis 18-21, M 8 hrs ago

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    You Are Somewhat Renaissance You are an independent learner and thinker. You like to follow...
    fatternfatter fatternfatter 56-60, M 8 hrs ago

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    This is my dream to drink milk from a woman anytime I want
    WarmMilk4Me WarmMilk4Me 36-40, M 1 Response 8 hrs ago

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    first time out: i have been out a few times in the past but allways when i was sure i nobody could see me, or atleast nobdu would be albe to se my face from the distance, but then...
    bodylower bodylower 36-40, M 9 hrs ago

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    i have done it a few times in the past but allways when i was sure i nobody could see me, or atleast nobdu would be albe to se my face from the distance, but then a few days ago we...
    bodylower bodylower 36-40, M 1 Response 9 hrs ago

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    If you hold your wedding in fall, it's time to choose bridesmaid dresses! The styles for fall are different than those you might choose for a summer wedding. Here are some useful...
    flywishes flywishes 26-30, F 13 hrs ago

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    l would love to share the experience with someone else it would make it much more fun
    dresscross dresscross 51-55, M 5 Responses 1 day ago

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    I absolutely love it I cannot get enough of it love the under wear so must to try on it is never ending love it love it
    dresscross dresscross 51-55, M 1 Response 2 days ago

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    Every night before I go to bed I act like I'm being forced into a sex change that I choose it to stop... I like doing that for some reason and I wish I was a female. I love doing...
    Crossdress4life Crossdress4life 18-21, M 2 days ago

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    I am always terrified of being discovered, but still love the feel I have when in pretty femine clothing. Right now I am sitting in my kitchen wearing a bra, panty, and green...
    julia09 julia09 56-60, M 8 Responses 3 days ago

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    Women jeans was my first outer garment I wore, soon to be neutral short sets and as my male clothes were replaced my wife kept enlarging my female apparel until I had no choice...
    CdKimmi CdKimmi 66-70, M 7 Responses 3 days ago

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