I Wanted To Know Why Do You Cross Dress

Personal Stories, Advice, and Support 182 People

    Why Do I?

    This is something I have thought about a lot. I think I have always had this desire for feminine things. I first tried on panties at the age of 6 (got caught,did not repeat that putting on mom's panties). as a pre-teen, I was obsessed with the womens / teens underwear section of...
    mcmouse50 mcmouse50
    56-60, M
    1 Response Jan 12, 2011

    Why I Cross Dress

    I cross dress because women's clothing is comfortable and there is a better choice of textures and colours in women's clothes than mens
    aquarius3 aquarius3
    Jan 17, 2012

    It Feels So Good.

    I just love the feel of lingerie agains my body. I love to wear pretty dresses and high heels. Okay, maybe they aren't comfortable but they sure look nice. I think I have nice legs and want to show them off more. Crossdressing is my pleasure, but feminizing myself a little...
    PinksWoman PinksWoman
    61-65, T
    Sep 17, 2012

    From my earliest memory I have always wished I

    was female and dressing the part has always brought me closer to feeling the way I think I should be. I can't really say that I feel like it is crossdressing anymore. Now It just feels like it is me being the way I am suppose to be and dressing the way I am suppose to be...
    NitaCD NitaCD
    66-70, T
    6 Responses Aug 10, 2015

    You would be better off asking,

    "Why do I try to stop Cross Dressing!", it would be a lot easier to answer. But to answer your question .... Because it felt natural to do so.
    rlt171720 rlt171720
    61-65, T
    Oct 28, 2015

    I Cross Dress

    I cross dress because I like how female clothes feel on me & there is a bigger choice of what to wear & the range of colours is much bigger than mens clothing
    xdpaul xdpaul
    56-60, M
    1 Response Jul 4, 2011


    I started because it gave me a sexual thrill wearing my sisters clothes. I did it privately as an adult because even though I told my ex about my desire, she wanted nothing to do with it. Now I am 60 and have begun living as a woman full time because that is what I really want...
    PinksWoman PinksWoman
    61-65, T
    2 Responses Sep 25, 2012

    I Am Who I Am.

    I dress because it is a part of who I am. Yes all the silky clothes are wonderful but I can't remember ever not wanting to dress in feminine attire. It grounds my soul to who I really am. Not a boy not a girl but me. When I was little I used to pray that boys grow up to be women...
    softerside softerside
    7 Responses Nov 11, 2013

    Because there is no better feeling in life

    than the full expression of one's inner self. Plus I love the feel of soft silky fabrics against my skin, especially flowing skirts against my legs through pantyhose on a warm summer day. I crossdress, because if I couldn't, I would die.
    KatieTreat KatieTreat
    51-55, T
    4 Responses Mar 31, 2014

    Just Want To Feel Comfortable

    I have to admit that I started "Crossdressing" at an early age. It all started as I can best remember when i was about 9 or 10 playing in our down stairs laundry.  that is when i seem mom's panties and i thought I'd try them on for giggles and grins.  I felt this sensation...
    deleted deleted
    8 Responses Sep 4, 2012

    I love when I get out of the shower

    before bed and put on my Victoria 's Secret night shirt with a pair of bikini panties. it relaxes me sooooo much before bed and I sleep like a baby!
    deleted deleted
    Jul 13, 2015

    My Story

    I have crossdressed since I was five but have recently begun to feminize myself and live as a woman full time. I don't it crossdressing anymore. Wearing dresses is what a woman does. I have been out in public many times, always wearing pants though and blouses over my lingerie...
    PinksWoman PinksWoman
    61-65, T
    3 Responses Sep 20, 2012

    To Be The Woman

    that i wasnt born as it is a part way house that started about 10
    christinemelody christinemelody
    56-60, T
    1 Response Apr 7, 2013

    Don't Know Why....

    I don't know why i crossdress, but i love to crossdress. It started at my age 4 in the kindergarten... I tried a leaf green satin skirt, and a girls shoe, but the memories i lost, after i tired them... Few age later, my parents divorced, i left with my mom, and i start wearing...
    VivienXX VivienXX
    26-30, T
    1 Response Jul 13, 2010


    it makes me fell so good sexy pretty
    vpesce35 vpesce35
    46-50, M
    Apr 7, 2013

    Why Do I Cross Dress Why Not

    Why limited your self to just wearing pants and shirts most women don't always wear a dress or skirt or make up or high heels all the time does that mean there are trying to feel masculine when they wearing pants and shirts no it was a choice that they maid that day . Clothes are...
    notech64 notech64
    41-45, M
    2 Responses Jun 17, 2010
More Stories