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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,124 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 8 Responses Feb 5, 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 20 Responses Jan 22, 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 22 Responses Jan 10, 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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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 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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    Yes I Do And Love It

    Yes I like to dress like a woman. What is not to like? The soft and silky nylon panties? The support and massaging effect from panty hose and the smooth feeling of your legs? The support and firmness for a good bra for your breasts? The silky feeling and coolness from a slip...
    Adam59 Adam59 56-60, M Aug 29, 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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    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 13 Responses Jan 11, 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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    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 6 Responses Jan 21, 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'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 4 Responses Jun 20

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    But Don't Want To Be One

    Even though i love to dress like a woman,i don't need to be one.I am happy being a male.I only like dressing as a woman.
    cindyloulove cindyloulove 56-60, M 1 Response Feb 7, 2012

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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 4 Responses Mar 30

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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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    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 (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 24 Responses Jan 15, 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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    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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    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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    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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    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 40 Responses Jan 31, 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 67 Responses Jan 7, 2013

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    Related Experiences

    In my younger days there was some occasions I wore a dress or girls clothes (see my other stories) but until I lived at home with my parents I never really wore dresses on a...
    ToShareStories ToShareStories 22-25, M Jun 26

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    I got up early on Sunday dressed and makeup, wearing a maxi dress with flowers on,I had a great day shopping and drinking coffee in brighton, I got looked at by two woman after...
    amber8642 amber8642 51-55 1 Response Jul 1

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    jmallon764 jmallon764 18-21, M 1 Response 6 hrs ago

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    i am a male cd i always wear female dress at night when i go to bed with my wife she accept my hobby of cd she helping me for this she help me in purchase my ladies clothes she...
    surekha57rpandya surekha57rpandya 56-60, M 6 Responses Jun 27

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    I love cross-dressing specially when my mistress punish me because of not cleaning correctly the toilet, sometimes I hate her because she makes me wear heels all the day
    sashaching sashaching 16-17, T Jun 23

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    A sense of fashion is an integral part of class. While having an eclectic style may be considered “cool,” as a classy dresser, you can hardly go wrong with a business...
    Mastertist Mastertist 31-35, M 1 Response Jul 1

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    Someone who loves you listens to what you say. He will value your opinion and take it into account when making decisions that affect both of you. If a guy puts your opinions down...
    lemongrass09 lemongrass09 46-50, F 2 Responses Jun 26

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    I am in bed wearing pink panties and a red nighty and wishing that man was with me.
    Rossie1703 Rossie1703 26-30, M 3 Responses Jul 9

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    + You have a sense of fashion as an integral part of class. You can hardly go wrong with a business/casual look or a simple, clean cut, fitting attire. Simple, straight colors...
    Mastertist Mastertist 31-35, M Jul 1

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    …because deep inside me is a little girl, so vulnerable, so helpless, weak, scared, full of longing....so when the tears stream down my face, and I don’t have anything to say...
    lemongrass09 lemongrass09 46-50, F 2 Responses Jul 2

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    Ever since I was 12 or 13 I've been cross dressing in secret. My mother caught me once when I was about 13 or 14. She was okay with it and asked me if I liked cross dressing. I...
    masspink masspink 18-21, M 2 Responses Jul 2

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    I am now 71, and too old to do anything about this. But I have always longed to be a woman. To dress sexily like a woman can, to have sex like a woman, to teeter on tiptoe like a...
    peter13942 peter13942 70+, M 4 Responses Jun 29

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    More like a woman. I like wearing dresses and skirts, pretty Lacey underwear and bras. I like curling my hair and smelling good. I like baking and helping people. There is...
    theyrereal theyrereal 31-35, F 7 Responses Jun 24

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    Check out lisagirl.net.....this guy is living the dream, he really looks like a woman. Mainly he has tips about how to pass as a woman in public....it is so fun to shop for women...
    susanwarfie susanwarfie 41-45, M 1 Response 5 days ago

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    This is dedicated to all women that are naturally hairy and are brave enough to let people know and that do not hide in shame. This is the way God intended us to be, he did not...
    Pmacphoto Pmacphoto 66-70, M Jun 29

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    A plane passed through a severe storm. The turbulence was awful, and things went from bad to worse when one wing was struck by lightning. One woman lost it completely. She stood...
    ScotsQueen ScotsQueen 51-55, F 1 Response Jul 10

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    Bad things always seem to happen to me when I begin to really like someone. Here is one example. At the beginning of this year, I started talking to this guy more. Eventually I...
    Diamondgirly Diamondgirly 18-21, F 3 Responses Jul 13

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    I like a woman in my chest acarcie privacy. because I also enjoy her breasts
    ommmar ommmar 31-35, M 3 days ago

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    I don't care if you are coming over or not, I love wearing lingerie and have amassed quite a collection. I wish there could be lingerie days so I could wear it in public too.I love...
    theyrereal theyrereal 31-35, F 8 Responses Jun 24

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    I just love how they're raised with good manners. They're always polite and hold the door open for the ladies. They all love and respect their mamas and grandmas. I have not met...
    texaschic35 texaschic35 31-35, F Jun 30

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    I like my woman how I like my chocolate....White, with no nuts.
    jojo0915 jojo0915 31-35, M 1 Response Jul 12

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    Exactly , it you're a man and ever hit a woman (even once), you're less of a man than I am, and I ware dresses.
    DawnR59 DawnR59 51-55, T 6 hrs ago

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    Oh what a title we hold. So glorious in thought, crappy when it comes to reality. It takes a strong woman to be in this position, despite what others think. To be the "perfect...
    Brokenhearted14 Brokenhearted14 22-25, F 2 Responses 5 hrs ago

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    I'm so happy that times have changed and it's possible for transgender children to become their true gender at such a younger age than I was able to. I am a girl. I've always...
    SaharaSands SaharaSands 46-50, T 1 Response Jul 7

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