I Love Dressing As A Woman

Personal Stories, Advice, and Support 1,793 People

    Sadly though it has to be in secret,

    but I really do enjoy it. That feeling of somehow being free is great.
    Johnina Johnina
    70+, M
    3 Responses Jun 29, 2014

    Not sure if anyone is following this

    but Ron canceled our date for Saturday night because he said he had to work all day Saturday. I was upset to say the least-but decided to just not worry about any of it and let things fall where thy may. Later in the day i decided to go to the sports bar where we had our second...
    Kittenkiss76 Kittenkiss76
    66-70, M
    2 Responses Nov 17, 2015

    My salesman( his name is Ron) came back

    and wanted to chat over coffee. I met him at a local coffee shoppe and we spent almost 3 hrs chatting and having a great time together. He wasn't to forth coming with many details of his life-but i can feel the pain in his voice. Were going to meet for dinner later this week and...
    Kittenkiss76 Kittenkiss76
    66-70, M
    2 Responses Nov 2, 2015

    I would love to dress

    as a woman all the time. Going out in public so that everyone can see me. A few times at night I've got dressed up and drove around for a couple of hours. I've drove along the motorway with the interior light on, knowing that trucks passing can see into my car. Men wore dresses...
    albro1000 albro1000
    41-45, M
    3 Responses Jan 5, 2014

    Being able to bring out my inner woman

    and not hide her anymore is amazing! I've started coming out to close friends and I couldn't be happier about the feedback I've received!
    tgheather tgheather
    31-35, T
    5 Responses Oct 26, 2015

    Do I wear my floral dress today with pink pumps

    or my black and white outfit with cream peep toes? The choices us girls have to make
    deleted deleted
    8 Responses Dec 22, 2015


    i so love dressing as a woman it is the most amizing thing in the world to me the way i feel when i go out is like i am the person i was ment to be i love clothes and shoes and makeup and all the things that woman do dressing as a woman makes me so happy and i feel so free like i...
    stacyhopes stacyhopes
    31-35, M
    2 Responses Mar 22, 2013

    I love it so much and cannot stop myself dress

    up in women's clothing and sexy under wear and stocking
    janetjanet janetjanet
    51-55, T
    3 Responses Mar 30, 2016

    The other night my wife

    and I went out to eat. Enroute I reclined the front passenger seat and she says the front portion of your (my) bra cups were raising my top enough that my bra was noticeable. All I said was "really". There were 2 small mounds in my top. neither of us said a word the rest of...
    serinalynn serinalynn
    66-70, M
    2 Responses Aug 18, 2015

    So it had been about one

    or two weeks since the "game" and I have non stop dressed up as a girl as in my sweat pants drawer I have a skinny jeans, a dress, a bra, 2 pairs of panties and lipstick and lipgloss my mom has not noticed.
    mater717 mater717
    18-21, T
    Mar 30, 2016

    Prt 3: my mom makes me go out ALOT!

    After we got our nails done my mom took me out to a local restaurant she told me I have to eat slow like a lady and if any bathroom emergencys don't forget to use the lady's room with a smile. We went in I ordered my usual and then all of a sudden I had to use the restroom and I...
    mater717 mater717
    18-21, T
    Feb 15, 2016
    nj00001 nj00001
    22-25, T
    4 Responses Mar 19, 2016

    Sunday Dressing

    I find that on sundays I have mor time to myself and have gotten the urge to dress again. I stopped for awhile hoping that I could get back out in the dating game and have a nice relationship. But after many long drives ( which is where I do most of my thinking) I realize that...
    Julie4728 Julie4728
    51-55, M
    4 Responses Aug 5, 2012

    Thinking About Coming Out To My Girlfriend

    She has caught me dressing before. Not in person but on my phone. I had pics on my phone of me fully dressed with her make up and all. Her underwear, bra, stockings , mini skirt, heels and top. We kinda talked about it for a little but i was so embarrassed that i got the topic...
    lonleycdresser lonleycdresser
    22-25, M
    10 Responses Oct 28, 2012

    Check this out then or get it

    for a friend. http://www.amazon.com/Feminizing-Men-Achieve-Maximum-Feminization/dp/1502959674/
    AaronFel AaronFel
    3 Responses Nov 28, 2014

    Sisters Petticoat

    My first experience of female clothing was at the very young age of 6. I don't know why this happened but I woke up in the middle of the night & quite out of the blue with no previous thought, felt a sudden desire to try on my sisters petticoats & slips. I didn't question my urge...
    susanpod susanpod
    Aug 26, 2013

    Here is a picture of

    when I felt like dressing as a sorority school girl or something...😆😆😉
    deleted deleted
    1 Response Jul 5, 2015

    Went back to the doctor

    for my two week check-up and my glucose was almost back to normal.!!! YEA... Lost 11 lbs and i feel so much better. Now I'm so glad i cut out white sugar all together...That was the good news--Ron called me a few nights ago and he wants to start seeing me again. I just don't no...
    Kittenkiss76 Kittenkiss76
    66-70, M
    Jan 28, 2016

    My Wearing Of Women's Clothes

    I started wearing women's/girls clothes at the age of13/14 after nicking a pair of tights/pantyhose from a school mate's sister & I found out that I liked wearing them as I had a paper round at that time I decided to start buying my own, I got fed up a few years later of just...
    xdpaul xdpaul
    56-60, M
    Jun 9, 2012

    It's such a great feeling to have those tight

    clothes upon my skin. If I could dress in public and not be scared I'm going to get judged then I'd love it.
    deleted deleted
    4 Responses Jan 12, 2014

    Would anyone spank me over there knee

    as I have been a bad girl
    deleted deleted
    5 Responses Dec 22, 2015

    Yesterday after a stressful day at work i

    couldn't stop thinking about getting home and changing into my wonderful women's clothes. I stopped at the grocery store and got a steak and a few other things for dinner. Got home and showered and dressed in a nice white top-black skirt and black stockings. Started dinner and...
    Kittenkiss76 Kittenkiss76
    66-70, M
    5 Responses Oct 9, 2015
    JulieCakes JulieCakes
    18-21, M
    4 Responses Dec 24, 2015

    Having underdressed with bra

    and panties for about 5 years, I have recently gotten into wearing skirts! Long, flowing skirts, knee length skirts and even slutty little mini skirts - I love them all. (With my large beer belly, my favorite skirts are maternity skirts!) The feeling of airy openness and...
    DonnaSue10 DonnaSue10
    66-70, M
    1 Response Dec 1, 2014

    Changing Times

    I feel that i no longer can indulge in my crossdressing ways. It was so much more enjoyable when I could share it with women. I did so like having sex when dressed. Now that I kike being alone, it's not as much fun. I have started purging again. As I get older, don't want anyone...
    Julie4728 Julie4728
    51-55, M
    7 Responses Jan 20, 2013

    I Too Love Dressing As A Woman.

    I was surprised to see this title because I often think about how dressing and smelling like a female heightens my spirits. I am now 63 and have a grand daughter who is 23 and lesbian. I have no problem with her life-style except I often wonder why she won't be more feminine as...
    deleted deleted
    2 Responses Apr 26, 2013

    I Love This !

    hey everyone i have so much to say ! i'm new to this website !!! i wanna meet as many people like myself! so lets talk ??? so excited to talk to you ladies ! and men ! xoxo Marissa <3 message me add me ! i'm friendly
    deleted deleted
    6 Responses Nov 3, 2013

    I went shopping the other day,

    fully dressed except for not having any panties on. Lovely divine feeling
    deleted deleted
    6 Responses Dec 22, 2015

    So tomorrow me and my girlfriend are going on a

    belated valentines day date and I might wear some leggings and maybe a shirt. I'm not sure. I'm so glad she accepts me.
    deleted deleted
    Feb 14, 2014

    I Am Obsessed With Living As A Woman

    I have an obsession with being a woman. Like most I started dress when I was young, about 13. I started with a pair of panties, and panty hose. I was satisfied with this for a long time but when I was a senior in high school I had the chance to dress completely. I wore stockings...
    sissysuzy sissysuzy
    31-35, T
    5 Responses Aug 27, 2012

    The Karla Collection.

    I now have a drawer full and a chest full of woman's clothes to make me happy. I have a total of 9 maxi dresses, 4 push up bras, 6 pairs of panties, 2 skirts, 4 shorter dresses, one pair of slacks, one blouse, 2 tops, one white silk negligee and bathrobe, one short flannel...
    FrauleinKarla FrauleinKarla
    61-65, F
    2 Responses Dec 4, 2013

    This morning I put on my bra

    for the day, A Cacique Lace Plunge bra, a Boy Short Pantie and a white mini sun dress. The weather is cloudy and rainy until Wednesday, so my sun dress will not be outside much. It was fun getting dressed though.
    serinalynn serinalynn
    66-70, M
    1 Response Aug 17, 2015

    All The Time

    can't think of anything else I want to do now. I dont have to transform completely with wig and make up but totally dress in womens clothes with lipstick on. was in the gents in a pub yesterday and a guy apologised thinking he was in the ladies so I must be doing a good job of...
    christinemelody christinemelody
    56-60, T
    1 Response Jun 23, 2012

    I love to be with other women

    while dressed as a woman, going shopping, going to the beauty salon, ect, just being one of the girls,
    DawnR59 DawnR59
    56-60, T
    2 Responses May 4, 2014

    Sometimes i get confused about life-but i must

    forge ahead and try to make the best of this life. Ron called last night and wanted to talk and i should have hung up on him. But we chatted and settled a few of our differences. I was dwelling on myself and didn't think about his feeling about dating a cross dresser. Men can be...
    Kittenkiss76 Kittenkiss76
    66-70, M
    Dec 23, 2015

    My First Crossdressing In A Girl Slumber Party!(:

    ok lets start,hello im shay and im 16 years old. my story srart 4 yers ago , my parents were on a vacation for 2 weeks,some night my old sister (16, today shes 19) had a pajamas party with 2 friends.2 days before the party i got an F in a test in school and i didnt tell my...
    SHAY8877 SHAY8877
    18-21, M
    2 Responses Sep 21, 2012
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