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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,271 People

    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 13 Responses Mar 28

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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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    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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    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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    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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    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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    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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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 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 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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    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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    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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    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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    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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    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 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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    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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    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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    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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    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'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 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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    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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    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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    deleted deleted 26-30 2 Responses May 3

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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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    Related Experiences

    Really need a naughty woman with a dirty mind to tease me ;) ... message me.
    scott1123 scott1123 56-60, M 42 mins ago

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    the greatest of both worlds i adore a woman with a heavy all natural large chest and a backside as wide as a bus.... 
    thebustierthebetter thebustierthebetter 46-50, M 1 Response 51 mins ago

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    I like the way the light material just lays on a woman's every curve. Every movement of her body shows--very enticing. The skirts hiding what lies beneath, slight hint of breast...
    TW8NY TW8NY 41-45, M 2 Responses 1 hr ago

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    I love dressing up. I love the feeling you get when you're all dolled up and looking and dressing sexy. I love the way it makes me feel and I love the way people look at me when I...
    axylleigh axylleigh 18-21, F 1 Response 3 hrs ago

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    The gift basket delivered yesterday afternoon. I saw him later at work, he just stared at me while he walked past my dept. So a little later I called him from our work number. He...
    plusisamust plusisamust 26-30, F 2 Responses 3 hrs ago

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    Today has been one of those days. I feel like throwing in the towel on this whole thing. I have a guy at home who doesn't appreciate me and now an ap who seems to like to reel me...
    joyfulcloudofsorrow joyfulcloudofsorrow 31-35, F 6 Responses 7 hrs ago

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    I'd prefer if you smelled like fresh strawberries picked by Jesus at all times
    TOR0NTOguy TOR0NTOguy 22-25, M 14 hrs ago

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    I love to dress up and doing my hair everyday. Growing up watching my mother dress up for every occasion. Up every morning before 6am to attend to her beauty routine. It's only...
    Sofiamafia Sofiamafia 26-30, F 6 Responses 2 days ago

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    Had the best girlfriend night last night with my bestie and gf. She lets my inner bad girl come out and love every minute of it. Can't wait till the next time Robin comes out to...
    chigirl68 chigirl68 46-50, M 2 days ago

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    Hi girls, I decided to go out in public again as a woman again and I start to run every morning with pants or shorts and tank top under my regular clothes, last time, I was wearing...
    Loren18 Loren18 18-21, T 2 days ago

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    My preference resides in a woman in a lil' black dress for an nite out, an evening with friends, or simply that one-on-one close encounter in the confines of your home. After all...
    DidISayThat69 DidISayThat69 56-60, M 2 days ago

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    This isn't so much about getting caught dressed, (I was but that story is in " I got caught Crossdressing"), so much as it's about the consequences. My ex mother in law was...
    amandatrane1 amandatrane1 51-55, T 1 Response 2 days ago

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    I have been wearing pantyhose for many years. I started in my teens. At home, under my clothes, or fully dressed up in high heels, panties, bra, and short dresses, I enjoy how...
    lascruces1971 lascruces1971 41-45, M 1 Response 3 days ago

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    I would be willing to do anything, go to any length to be accepted by someone as their woman and only their woman. Hormones, surgery, or nothing at all if that was what they wished...
    amandatrane1 amandatrane1 51-55, T 1 Response 3 days ago

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    Right now I am wearing a short black PU dress with stripes. Also my black knee high boots. This feels so very comfortable right now. I could wear it all day.
    12rak38 12rak38 36-40, M 3 Responses 3 days ago

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    My username is candywhite26, so to avoid any further confusion like what happened the other day, while chatting with a male friend, I was politely asked If I cross dressed to which...
    candywhite26 candywhite26 56-60, M 2 Responses 4 days ago

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    I was walking down the hall at work, when a young woman in her twenties came around the corner. She must have been 6'2" in flats and was wearing a dress. It wasn't particularly...
    Longlegs2014 Longlegs2014 41-45, T 4 days ago