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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,439 People

    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 15 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 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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    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 really feel like I am totally another person

    when I am in my feminine things. Just the feel of satin against my skin and a flowing dress down my legs takes me to a new place. I do sometimes have a fantasy of when I am getting dressed that I am getting ready for my boyfriend to come over to take me out somewhere.
    ReneeTalley ReneeTalley 56-60, M 1 Response Oct 14, 2015

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    Back when I was younger

    and had the time I dressed up often, and when it was possible I would remove as much body hair as possible. That's when I really felt like Feminine creature. Plus to have someone lay their hands on my legs or any other place there is no hair would excite me more. It still...
    rlt171720 rlt171720 61-65, T 1 Response Sep 11, 2015

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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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    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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    Deep down inside I am a woman

    and dressing like one allows me to be me!
    TrannyHannah TrannyHannah 41-45, T Nov 16, 2015

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    deleted deleted 26-30 2 Responses May 3, 2015

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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 8 Responses Jan 11, 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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    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, 2015

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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 2 Responses Aug 5, 2015

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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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    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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    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 26 Responses Jan 31, 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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    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 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 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 66-70 1 Response Jan 10, 2012

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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 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 3 Responses Apr 23, 2015

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    I think, that in my desire to be womanly I have

    succeeded in becoming like a woman of the 40's and 50's! I'm not sure if this is a good thing or not. My days now are filled by carrying what where traditionally womanly chores, washing, ironing, cleaning, shopping. I'm not being very liberated at all. My partner has gone along...
    deleted deleted 26-30 2 Responses Jan 1

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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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    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, 2015

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    women are beautiful and I like to dress

    as one to look beautiful. I shave my legs almost every day and I exercise my hips so I can try to have that feminine figure
    deleted deleted 26-30 1 Response Jan 21

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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 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 (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 18 Responses Jan 15, 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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    Related Experiences

    I dunno, A couple months ago I just gave up shaving, i felt like it was a waste of time, because of this i have a large bush and armpit hair, but honestly, I feel better like this...
    MettaBabe MettaBabe 13-15, F 7 mins ago

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    I found a book on the New York Times review that I plan on downloading on my kindle. "Alive, Alive, Oh!" The musings of a 98 year old former London book editor. I love reading...
    Tullia1510 Tullia1510 46-50, F 1 hr ago

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    Any cd's or tgirls out there that would like to chat and share experiences.
    luvtgcds luvtgcds 41-45, M 1 hr ago

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    This is not an "older" woman story but back in high school. I was 16 and my now wife was 18. We were not a couple, she was just a girl in my study hall and I was a shy long haired...
    Garraway Garraway 51-55, M 1 Response 2 hrs ago

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    Here are some ideas i like playing: Molding a figure of a person and then they grow like it. We take a class in sculpture and I decide my first project will be a pregnant woman. I...
    augustus2009 augustus2009 26-30, M 3 hrs ago

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    I would love to wear this dress
    Jasminesissy Jasminesissy 26-30, M 1 Response 3 hrs ago

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    One thing I have yet to do, in the 15 years I've been crossdressing, is find some one to host well I get all prettied up. Fix my makeup, throw a pretty wig on, and throw a sexy...
    Jasminesissy Jasminesissy 26-30, M 3 hrs ago

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    My favourite summer girly dress.
    TeresaGurl TeresaGurl 36-40, M 1 Response 5 hrs ago

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    Oh no, where did my dress go?!
    TeresaGurl TeresaGurl 36-40, M 2 Responses 8 hrs ago

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    My slutty red heels always make me feel like a girly girl
    TeresaGurl TeresaGurl 36-40, M 1 Response 8 hrs ago

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    It makes me feel like someone else. Dressing up gives me an alter ego, I'm not me I'm this new person who looks better than I originally did.
    Kirstyj19 Kirstyj19 16-17, F 3 Responses 18 hrs ago

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    Update on my social transition finaly got up the courage to be in this really pretty dress. So I got up early shaved did my make up and fixed my wig. I was looking as passable as...
    SolayTranswife SolayTranswife 26-30, T 1 Response 23 hrs ago