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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,309 People

    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 14 Responses Jan 10, 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 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 I started my latest phase (or Part 3).

    It was December 2013, I had been on a new job for a couple of months, through which I hadn't really been able to do anything but work. Years had passed since that last incursion to my aunt's closet and since we moved to our own home, but that weekend I had the house for myself...
    Automx Automx 26-30, M 3 Responses Aug 5

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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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    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'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 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 3 Responses Apr 23

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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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    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

    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 53 Responses Jan 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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    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 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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    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 27 Responses Jan 31, 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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    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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    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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    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 12 Responses Mar 28

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    deleted deleted 26-30 2 Responses May 3

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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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    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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    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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    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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    Related Experiences

    If I could I would wear a dress everyday
    lexi72 lexi72 41-45, M 1 hr ago

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    For the last three weeks, I’ve worn panties with napkins to hold me tucked, a bra, and nylons continuously. When I go to bed I put on pj’s and my you know what, it seems like...
    joanw joanw 61-65, M 1 day ago

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    i am a boy and i love to wear female dress and makeup and long hair wig since i was 12, i used to wear all feminine things and become bride(dulhan) whn i am alone at home and i...
    zarapakistani zarapakistani 22-25, T 1 Response 3 days ago

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    i am a boy and i love to wear female dress and makeup and long hair wig since i was 12, i used to wear all feminine things and become bride(dulhan) whn i am alone at home and i...
    zarapakistani zarapakistani 22-25, T 3 days ago

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    Wearing a bombshell bra and panties, black pullover, red plaid mini skirt, fishnet stockings and MaryJane shoes, foundation, black eye shadow, red lipstick and my Cleopatra wig. It...
    Foxanne Foxanne 22-25, T 4 Responses 4 days ago

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    My name is Vicky. I have cerebral palsy. I went to a boarding school near Brighton. I was a pretty girl then. I had long blond hair. I am slim as well as being quite small. I...
    vickybiggs vickybiggs 18-21 1 Response 4 days ago

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    I enjoyed my day. I needed some milk and other groceries so I decided to go out dressed as a girl. My legs are fairly tan but my toe nails were not done properly. I decided...
    RandiHill RandiHill 51-55, M 4 Responses 5 days ago

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    A big girl is a girl that has much more to love and enjoy...I for one like a woman with some extra pounds all over her big sexy body.If you're a big girl looking for a man who...
    thebustierthebetter thebustierthebetter 46-50, M 6 days ago

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    Dressing up can be the best thing ever. I never get bored because I love dressing up and it occupies me a lot. From makeup, clothing, accessories and shoes it's amazing. I love...
    Pinkygir Pinkygir 16-17, M 2 Responses 6 days ago

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    okay I love dressing up almost every day, wearing my makeup , wearing skirts and a nice top or sometimes even dresses , I'm not much of a fan wearing jeans I barely have 6. I dress...
    bloodyzombie19 bloodyzombie19 16-17, F 1 Response 6 days ago

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    I have never ever come across a woman who accepts, loves or forces their man to cross dress and be a female. If I ever come across a woman like that I'd love her until death. I'm...
    Pinkygir Pinkygir 16-17, M 1 Response a week ago

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    Tonight I'm out on my favorite walking trail listening to C&W music dressed in my favorite blue skirt and heels. Having a good time just being honest and myself. It's becoming more...
    shadowplt shadowplt 51-55, M 5 Responses a week ago

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    Not much went down today. Woke up as usual to the sounds of my sisters waking up in the next room. I actually felt decently well-rested. I lolled about before getting ready for the...
    PinkMellow PinkMellow 18-21, F Aug 23

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    When i'm alone i feel pretty
    ayeshadenji ayeshadenji 16-17, T 1 Response Aug 23

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    I love all types of clothing - Traditional, Dresses, Jeans, Party wear, skirts and Office. Various dresses but same person and loving girl underneath. What type of clothing do you...
    angelsndemons angelsndemons 22-25, F 5 Responses Aug 22

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    I've done it a couple times, first in my mid twenties and then again in my late thirties. The thrill I had gotten walking around a city at night, dressed as a woman, was...
    MnPantyBoy MnPantyBoy 51-55, M 2 Responses Aug 22