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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,175 People

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

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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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    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 4 Responses 7 hrs ago

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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 30 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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    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 55 Responses Jan 7, 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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    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 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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    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 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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    Related Experiences

    Sissy test : do you really feel like a woman ? Total for lori = 149 Good girl! Your score is really high! You feel like a woman, and that's why you dress like them...
    gandyr gandyr 56-60, M 19 hrs ago

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    I am a long time crossdresser. I have been wearing female clothes whenever I can from about the age of 10. No I do not concider myself a freak or bad. I just have a strong female...
    taracd55 taracd55 56-60, M 3 Responses Feb 28

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    I love to dress up as a women I get really excited when I get dressed up as a women looking forward to hearing from other people who like to chat with me I love to wear black...
    RosieinStockings RosieinStockings 56-60, M 3 Responses Mar 4

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    One thing I dislike more than cheese is shopping for a formal dress. ( probably because I'm picky lol) Guys have it easy when it comes to clothes. We have to look for dresses in...
    Nottheaveragegirl Nottheaveragegirl 18-21, F 10 Responses Mar 20

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    IHATE wearing make up! Hate it! But I cannot stand sweatpants or bad looking shirts (worn down old) unless i am building ir painting something...I have to be dressed good (semi...
    Mariferb86 Mariferb86 18-21, F 2 Responses 2 days ago

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    Dressed up today 😃 Black dress, tights and some gorgeous high heels. My hair I in a French braid. I just feel magic 😚
    ActingOut ActingOut 18-21, F 9 Responses Mar 16

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    Whether it's a simple collared shirt or a whole suit and tie, dressing up is awesome. There's no feeling like being dapper!
    Blue707 Blue707 16-17, M 2 Responses Mar 1

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    I've a slight obsession with high heels and dresses.
    bleuswain bleuswain 18-21, F 3 Responses Mar 10

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    I can't stand lighter blue jeans. Ever. They have to be really dark (so they're almost formal-looking), or wear some other pants. Sweatpants I can NEVER wear out and about during...
    Makaidos8 Makaidos8 18-21, M 1 Response 5 days ago

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    what is your outfit for today ? I love checking outfit on Instagram and follow their hashtags, they gives me idea of my outfit..just being a typical girl ,love clothes and shoes.
    sadwife82 sadwife82 31-35, F 1 Response 9 hrs ago

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    Just another morning waking up in my pretty pink nighty and bra...I feel wonderful !!!❤️
    Goodtimes13 Goodtimes13 56-60, M 1 Response Mar 9

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    Well all I have on is a lime green thong.
    razgrizizzy razgrizizzy 22-25, M 2 Responses Mar 9

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    It's true I do! Well then again I want to transition to a female completely! How do I look??
    LucyAshley LucyAshley 18-21, T 5 Responses Mar 3

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    Yea feeling ugly all day everyday
    LucyAshley LucyAshley 18-21, T Mar 12

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    I'm currently seeking out my Prince Charming. I neeeed a boy friend so badly
    LucyAshley LucyAshley 18-21, T 3 Responses Mar 16

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    Yea I'm one of those girls who looks terrible in both genders
    LucyAshley LucyAshley 18-21, T 7 Responses Mar 18

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    It makes me feel better about myself and helps me believe I look nice.
    planter715 planter715 51-55, M 2 Responses Mar 6

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    I post my outfit almost everyday on my Instagram.. some pictures I'm wearing stockings, or sexy sleepwear/lingerie I love them ..
    sadwife82 sadwife82 31-35, F 4 Responses 1 day ago

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    Went to the gym early morning came back and got the bath ready, relaxed for a few minutes, shaved legs and body.put cream on to moisten the legs and body.put on black hipster...
    lvrofhose lvrofhose 56-60, M 4 Responses Mar 3

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    I want that traditional gentleman. He opens the door, looks after me, man of the house, pays when we go out and I take care of him, love him, cook for him - we can cook together...
    confusednormalness confusednormalness 18-21, F 1 Response Mar 10

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