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I Like To Dress Like A Woman

Personal Stories, Advice, and Support 1,246 People

    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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    deleted deleted 26-30 2 Responses May 3

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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

    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 54 Responses Jan 7, 2013

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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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    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 2 Responses Apr 23

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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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    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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    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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    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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    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 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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    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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    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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    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 28 Responses Jan 31, 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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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 2013

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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 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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    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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    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 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 (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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    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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    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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    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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    Related Experiences

    It's been extremely muggy and hot the past few days. I chose to go out without a blazer or suit jacket on today. I thought it made sense as it was so hot out. I think it's the...
    cufflinks78 cufflinks78 36-40, M 1 hr ago

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    Luv my wife getting dressed up showing off her sexy slim legs and body and walking Into a bar.... Her beautiful breasts and face.. Luv the attention
    Vecci4u2 Vecci4u2 36-40, M 1 Response 2 hrs ago

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    I got a bit hooked to being controlled and psychologically manipulated by a dominant woman. I get weak and submissive when a woman gets off by humiliating me, creatively...
    fluge fluge 46-50, M 2 hrs ago

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    Give me some thick juicy steaks and two big hot buns.A woman with some meat on her bones, is a woman that's a whole lot of fun.Heavy up top some junk in her trunk whip me up some...
    thebustierthebetter thebustierthebetter 46-50, M 3 hrs ago

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    So my friend Emma has been planning her birthday party for a loooong time. I'm usually prepared and this instance was no different. I always wear dresses (black to be exact) but...
    MilkJune MilkJune 16-17, F 4 hrs ago

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    The next woman that I get into a relationship with, hopefully will love getting daily massages from me. I love the female body and I love caressing it all over.What better way to...
    thebustierthebetter thebustierthebetter 46-50, M 5 hrs ago

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    Surprise ,surprise,surprise....a group about liking busty women. Is that a thing? I just thought it was my second nature or part of my DNA. I more then like busty women. I bask in...
    thebustierthebetter thebustierthebetter 46-50, M 2 Responses 7 hrs ago

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    Though who are in relationships with lover with age gap between two of you like some guys like to be called daddy do you like call your lover that or to be called mama?
    ForbiddenFruitLove95 ForbiddenFruitLove95 18-21, F 3 Responses 7 hrs ago

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    The Babysitter Murders Chapter Twenty Mommy made me wait in the hall a second while she checked on everyone else. Mike, Barry and Suzy were all back in bed and in various states...
    MaryJanine MaryJanine 56-60, F 9 hrs ago

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    Quality vs quantity I've had a hard time with this one because I haven't been able to see him as much recently. When we are together though, it feels like we are really 'together...
    RedSheep2 RedSheep2 26-30, F 9 Responses 10 hrs ago

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    I like girls and guys and girls that dress like boys... identify as pansexual but it's so hard to explain
    tifalockheart123 tifalockheart123 26-30, F 1 Response 10 hrs ago

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    It my fav thing to have done!!! Last time I got dressed up met a Dom at his place. Got tied up in his basement. Tied to a chair gagged blindfolded! He had some fun then went...
    Brandybondage Brandybondage 36-40 1 Response 10 hrs ago

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    I hate getting dressed every morning cause I hate putting on clothes. I wait till the last second to put them on the I take them off the first thing when I get home.
    Nakedtoday Nakedtoday 26-30, M 2 Responses 12 hrs ago

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    So I wrote this off the top of my head. I wanted to get it down before I lost it. Any suggestions are appreciated and I'm ok with constructive criticism. Rough draft: Once there...
    Bingbongbingbong Bingbongbingbong 13-15, M 1 Response 17 hrs ago

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    Bridesmaids always come in different natural colourings, such as Blondes, brunettes, redheads. And the bride should choose a colour to suit each bridesmaid. However - not all...
    flywishes flywishes 26-30, F 17 hrs ago

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    I thought I'd never kiss a man, never but after I started dressing like a women I wonted to be treated as a woman. I was in a bar dressed to the nines, a man came on to me so I...
    stoflicken stoflicken 66-70, T 1 day ago

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    I really love dressing up wearing women's clothing
    lopez7879mc lopez7879mc 31-35, T 1 Response 2 days ago

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