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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,214 People

    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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    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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    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 (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, (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 10 Responses Jan 11, 2013

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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 16 Responses Jan 10, 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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    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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    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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    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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    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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    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 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 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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    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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    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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    deleted deleted 26-30 2 Responses May 3

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

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    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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    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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    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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    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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    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 (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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    Related Experiences

    On Saturday I spent the whole morning preparing myself so that I looked good to go and buy a dress. Then going into a popular department store I found gangs of girls all looking at...
    AWendy AWendy 41-45, T 1 Response May 12

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    Good Monday morning hope that your Mother's Day was good just getting over the day. I had a brunch for some close friends at the house. Everybody was looking good. Some had good...
    lvrofhose lvrofhose 56-60, M May 11

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    I love doing my hair, nails, face when going out alone or with others. When I put on my gown, dress, or skirt and blouse, along with my hose and heels, I feel like I am dressed to...
    oldermaturewife oldermaturewife 46-50, F 3 Responses May 6

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    i always dress up like i never dress down or watever i always wana look my best even if im just hanging out at my house with sum frends or watever i think its good 2 put in the...
    lacipink lacipink 18-21, F 3 Responses May 6

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    I just wanted to get dressed up and go out for the night. So over jeans and looking daggy. I just want to put on a nice dress and pair of heels. Do my hair, makeup and nails.
    Viviq66 Viviq66 18-21, F 3 Responses 5 days ago

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    I like being dressed to the nines, but honestly I also dislike the effort that goes into putting on all that makeup, accessories, and hair. When the pics turn out well or when I...
    iCuriousBabe iCuriousBabe 41-45, F 6 Responses a week ago

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    I have a performance with my new band today, and I only have a half hour after work to get dressed up for it, which is not nearly enough. I will most likely spend all day at work...
    Delphineidunna Delphineidunna 26-30, F 2 Responses 5 days ago

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    I love wearing dresses in warm weather. Short skirts are the best, especially ones that can blow up in the wind. And I love sleeveless tops, too. I love the sun and the breeze and...
    katiegray72 katiegray72 41-45, F 6 Responses 3 days ago

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    dresses make me feel so cute!!
    deleted deleted 26-30 2 Responses May 2

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    people always tell me to dress comfortably...they often fail to understand that in order to be comfortable I need to look my best, not to impress anyone , for me ...it's how I am...
    heartoverhead heartoverhead 18-21, M 1 Response May 17

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    Is this dress too sexy to wear to a formal business dinner. I would wear a matching black blazzer with it. Ladies what do you think?
    Lexyness Lexyness 22-25, F 2 Responses 4 days ago

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    I like pretending that I'm a teacher
    lesbiannica lesbiannica 18-21, F 5 Responses May 18

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    you know, just for the fun of it..I love clothes
    StevieOakley14 StevieOakley14 13-15, F Apr 28

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    Prom was wonderful!!! Now want to go be with my love<3
    Nottheaveragegirl Nottheaveragegirl 18-21, F 5 Responses May 2

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    I am gonna get myself a training corset.
    iCuriousBabe iCuriousBabe 41-45, F 2 Responses a week ago

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    Do you thin I'm a fuller figured girl ?
    sunnyup sunnyup 46-50, F 5 Responses May 15

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    My balls are so big love them licked
    wildreams wildreams 18-21, M May 17

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