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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,198 People

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

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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 a week ago

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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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    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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    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 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 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, (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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    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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    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, (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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    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

    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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    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 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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    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 1 day ago

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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 9 Responses Mar 28

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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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    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 (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 29 Responses Jan 31, 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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    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 Mar 27

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    I DONT REALLY KNOW HOW TO ACT LIKE A WOMAN, I HAVENT HAD TO YET, I JUST TAKE PICS IN MY ROOM THEN GET ON THE COMPUTER. I JUST SIT HERE. HAHA
    MacksInner MacksInner 31-35 Apr 12

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    OMG! I love dressing up for any occasion! I went out dressed as a hula girl a couple of weeks ago! It was awesome x
    Laurainthepink Laurainthepink 18-21, F 4 Responses 3 hrs ago

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    I am a married Male to female Cross-dresser.  I recently came out to my family.  So far its a pretty good.  I dress mostly when Im in my job.  I work alone, and usually spend...
    liziemary liziemary 36-40, M 5 Responses Apr 16

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    I have kept it a secret for a long time. Dressing only behind closed doors. The problem is that I wanted to step out into real world and be the girl I was hiding. Where I loved...
    rlt171720 rlt171720 61-65, T 1 Response 2 days ago

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    This is less about dressing, but anyway. I really want to buy a highly feminine shampoo.. but I feel embarrassed whenever I go to the shops to buy one. Any tips? I want to buy it...
    hairy96 hairy96 18-21, M 7 Responses Mar 31

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    I wish I knew more people like me in real life, I would love to host a teaparty where we all dressed up, drank tea and discussed our lives and show off our clothes! I bet it would...
    KitchenGun KitchenGun 18-21, T 4 Responses 5 days ago

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    On my days off I dress in my intimate wear and just walk around the house. I love the feel of satin all over my body. I even wear my maxi-pad and tampon underneath, it feel sooooo...
    Sissycolleen Sissycolleen 36-40, T 1 Response 1 day ago

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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 Mar 26

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    I love dressing up for work, eating out at restaurants, going to movies with my sons, shopping, running errands, and going to other places. I love wearing a nice short dress or...
    singleredheadfemale singleredheadfemale 41-45, F 4 Responses Apr 10

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    I love dresses i waer them alot in my boreding school.
    Emogirlriley Emogirlriley 13-15, F 1 Response Apr 10

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    Love this style:) Polo - Dress!!! #boyishtogirly #creative
    RedThatDescribesMe RedThatDescribesMe 18-21, F 8 Responses Apr 14

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    As comfy as I am in jeans and a hoodie, sometimes it's nice to dress up, go somewhere lush and have some classy time and spoil myself.
    Happyindark Happyindark 18-21, F 3 Responses a week ago

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    Sometimes I dress up as a Disney princess for no reason. (YOLO seems to be thge saying with today's generation of hormonal teens) My wife on a rare occasion will do the same, but...
    ThatGayGirl187 ThatGayGirl187 26-30, F 2 Responses a week ago

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    I guess there are men who are like this. It's just that sometimes women are too aggressive now compared to men.
    lemongrass09 lemongrass09 46-50, F 5 Responses Apr 9

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    I would never go with a skinny I did that one time and hated it was like hugging stick. Fat girls are soft and warm to hug feels so nice to not be able to put my arms around her...
    Chubbyhubby230 Chubbyhubby230 31-35, M 1 Response Apr 10

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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 6 Responses Mar 27

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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 2 Responses Mar 28

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