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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,156 People

    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 (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, (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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    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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    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 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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    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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    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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    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 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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    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, (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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    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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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 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 31 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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    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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    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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    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 55 Responses Jan 7, 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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    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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    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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    Related Experiences

    So I was asked to take some pictures the other night to show off my new shoes. I have a pair of patent leather 4 inch stiletto pumps with locking ankle straps. I was told to get...
    Photogeek47 Photogeek47 26-30, M Jan 1

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    Ever since I was 4 or 5 I felt like a girl. I was jealous of my sister by her body I didn't understand what was wrong with me I always would dress in her clothes when everyone was...
    jessicw jessicw 41-45 Jan 8

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    I dress up mainly for my man because it's fun and he always compliments me even when I don't dress up :) my man goes crazy when I put on a cute dress and straighten my hair and put...
    Mizpoppy Mizpoppy 26-30, F 1 Response 3 days ago

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    Woke up with the desire this morning. Wife had left for work, so out came the panty girdle from its secret hiding place. Maidenform, beige or creamy yellow, with a floral design...
    barbarainside barbarainside 51-55, M 3 Responses 1 day ago

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    I'm always excited when I have the opportunity to dress up. In August my uncle is getting married and I"m already looking at dresses to buy. I own five pairs of heels!
    Kayleehere Kayleehere 18-21, F 2 Responses Jan 8

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    I am 45 was married for 20 years and i had bad experience work ,family ,death , and work to long ours but in twenty years newer had a problem in our marrieds till i meet young girl...
    BOMKOP BOMKOP 41-45, M 1 Response Jan 11

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    I love shopping as a woman for feminine clothes and products and enjoying traditional feminine experiences like manis/pedis with feminine nail colors, leg & underarm waxings...
    debbienc debbienc 61-65, M 1 Response 2 days ago

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    I like having my balls squeezed by a women
    dj100a dj100a 18-21, M Jan 5

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    They look so smart and comfortable.
    bnaesf bnaesf 36-40, M a week ago

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    Thinking about changing my hair debating on going blonde or a purple to pink hombre
    AshleyNicolee AshleyNicolee 18-21, T 4 Responses Jan 14

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    i am wearing panty for my work its so soft and so comfortable..........
    daya55 daya55 26-30, M 1 Response Jan 15

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    i am going to buy a new nightgown tody....
    daya55 daya55 26-30, M 1 Response Jan 16

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    there's something lovely about the feeling when a girl starts choosing clothes to put on you and makes you go along with it :P
    charkzilla20 charkzilla20 16-17, M Jan 20

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    I love it. It's just so sexy.
    dj100a dj100a 18-21, M 1 Response Jan 5

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    No experience that yet.haha
    rpeace89 rpeace89 22-25, M 1 Response Jan 11

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    I've alwayse wanted to but never had the chance.
    gsand15 gsand15 18-21, M 3 Responses Jan 19

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    everyone has different taste but my favorite thing about my wife is how tiny and petite she is. that and her sexy feet
    Matthews6288 Matthews6288 31-35, M 20 hrs ago

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    I do agree, I think that all boys, at least at some stage of their lives, should be allowed to experience how wonderful wearing cloths made for girls could feel. They should be...
    mizmaid mizmaid 36-40, M 7 Responses Jan 11

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    I try to get out at leasy weekly. Lately i have toned it down a bit, age appropriate clothing & makeup. I seem to get fewer looks this way. I'll be heading out in a few minutes. I...
    ta61 ta61 51-55, T 2 Responses Jan 7

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    i like dressing uop as a girl i like how it feels to wear a dress and i want to look more like a girl
    guyinadress guyinadress 22-25, F 1 Response Jan 11

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    I desire this again. Mutual linger shopping is always a joy with a like minded woman. Can be so much fun.
    MichaelS41074 MichaelS41074 36-40, M Jan 18

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    Hi there I have a YouTube channel that I upload a video on every week! I like to do top ten videos like this video; top ten weirdest Holiday traditions! It includes things like...
    TheBellaBubbles TheBellaBubbles 16-17, F 1 Response Dec 31, 2014

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    The Baby Sitter. I love a woman a gut! Ever since I was a kid I've felt this way and there's a story behind it. I'll try to type it out as I remember it to the best of my ability...
    iloveflabbiness iloveflabbiness 18-21, M 1 Response 6 hrs ago

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    I am a colorful person, I work under the radar in a very stuffy environment that is completely controlled by preppy republican party members. I was out of work with a personal...
    severalanimals severalanimals 56-60, M 1 Response 2 hrs ago

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    I started like three years ago and because she lives away from home it has become very easy to do this. It feels so good!