I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,336 People

    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
    50 Responses Jan 7, 2013

    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
    24 Responses Jan 31, 2013

    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

    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
    8 Responses Mar 28, 2015

    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

    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
    15 Responses Jan 22, 2013

    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

    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

    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
    61-65, M
    1 Response Oct 14, 2015

    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

    Deep down inside I am a woman

    and dressing like one allows me to be me!
    deleted deleted
    Nov 16, 2015

    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

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

    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
    3 Responses Apr 23, 2015

    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
    1 Response Jan 1, 2016

    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
    6 Responses Feb 5, 2013

    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
    2 Responses Mar 30, 2014

    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

    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
    1 Response Jan 21, 2016

    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

    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

    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

    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
    1 Response Apr 3, 2013

    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

    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
    1 Response Jan 10, 2012

    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

    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
    Mar 28, 2013

    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

    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

    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
    deleted deleted
    2 Responses May 3, 2015
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