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I Like Dressing As A Woman

Personal Stories, Advice, and Support 1,630 People

    Dressing As A Woman

    As a youngster growing up my sister would dress me like a girl to make me behave which really did not work.  What she did do was light a fire in me by bringing out the feminity in me.  After some time she helped me become a complete cd showing me how to dress properly...
    robbiemaid robbiemaid
    22-25, M
    1 Response Apr 21, 2010

    Dressing As A Woman

    As I like dressing as a woman I have dressed as such every day for the last 20 months since I lost my job
    xdpaul xdpaul
    56-60, M
    Jul 14, 2011

    How I've Grown

    Like most of us I started dressing when I was little and love trying on anything that was sexy. I wanted to be dressed like all girls my age and what I wore the sky was the limit. As I grew into my teens I found I loved clothing being the sexier the better My aim was to excite...
    femboy4u femboy4u
    8 Responses Jun 23, 2011

    At Work Again

    well i did it again i went to work with a dress under my male clothes and when every one left i got my high heels out of my locker and took off my male cloth and all my work in a dress and heels it lelt good the next day i got called to the office thay seen me on cthe cam and...
    dragqueenpa dragqueenpa
    61-65, M
    3 Responses May 10, 2013


    I love dressing, but why? Perhaps just to be different. Maybe I'm bi? Maybe I'll never know
    Moddle Moddle
    70+, M
    3 Responses Jun 10, 2011

    I Like To Ware Pantys

    i enjoy gioing ot iny red panty and reb bra it makes me so sexy
    joeishere joeishere
    51-55, M
    1 Response May 28, 2012

    After working my short shift today,

    I stopped at the local Walmart to look at the halloween I do every year...and I bought one, it's mostly pink and reaches halfway down my back...but after half an hour or so, I switched back to my normal bob-cut.... I wanted to feel the hair gently caressing my neck...
    princesskendra princesskendra
    41-45, M
    1 Response Sep 12, 2015

    Adore Bras And Panties

    It all began with moms playtex magic fingers girdle with the air holes. The smell intoxicated me and it felt so wonderful, had to be very careful when wearing so i did not leave a telltale sign.
    curvationccup curvationccup
    51-55, M
    Jan 1, 2013

    Wanted To Show ...

    The below is two related, but different stories ... they are true. When I was living with a female friend of mine, I would often wear her panties, and bra, under my own stuff, and sometimes her dresses, shirts, and jeans. Well, one day I was putting on her jeans when she was...
    thebunny030 thebunny030
    22-25, M
    1 Response Jan 8, 2012

    I'm dressed right now a its the best feeling

    I'm just relaxed enjoying it. Taking lots of sissy selfies I LOVE IT! !!
    whitwhit86 whitwhit86
    31-35, M
    1 Response Sep 18, 2015

    I Am Soooo Lucky

    to have 2 young girls (real girls around 25) that support what i do and think its cool and sexy. one of them does my eyebrows for me and likes to put my makeup on. it really feels good to have female friends like that. the night staff at our 24 hour kmart are supportive too and...
    Mizsuzy Mizsuzy
    46-50, T
    Oct 23, 2011

    4am Knows All My Secrets

    I had to drop off the car I borrow for work three nights ago...I work nights and get home around 4am...I decided to take this opportunity to boost my already frisky mood and dress up a little for the 6 block walk back to my apartment, I went home first and put on...
    princesskendra princesskendra
    41-45, M
    Sep 28, 2013

    I Have Not Done It Yet.

    My wife is wanting me to wear a pair of her panties and a bra. I told her "Hell; let me wear a dress, shoes, and do my makeup".  She was in bisexualrelationships in the past and still enjoys looking at women. So I want to fulfill her fantasy of me being a woman. She does...
    Snookybear Snookybear
    36-40, M
    2 Responses Jun 22, 2010

    No More Clothes

    A little while back, I got laid off from my job, and decided I should go back to university, so I can get a decent job. In order to do so, I decided to move back in with my parents, since they agreed to pay for my tuition, and I get free food, and a place to stay - I don't have...
    thebunny030 thebunny030
    22-25, M
    1 Response Oct 2, 2011

    What A Weekend

    I new a bunch of crossdressers,one day we were talking and we all decided to go down to a Texas city for a 3 day getaway .I arrived on a Thursday evening rather late so I just went to bed, Friday morning ,my boy clothes were on vacation to ,Connie has come to play so I put them...
    deleted deleted
    Feb 10, 2011

    The Power Of Clothes

    What an interesting question: do you dress like a woman, dress up as a woman, dress in the same way a woman does, dress the "woman inside of you", or dress in a way that is simply right for you and ends up in being, to all intents and purposes, a woman?Maybe the real question is...
    Fullcircle Fullcircle
    51-55, F
    2 Responses Jan 27, 2012

    The Drive In

    my freind dave and i wanted to go to a movie but the only place it was playing was drive in which we told my older sister about it being weird that tw guys would go sister said why dont one of you dress as a girl and people will think it a boy and girl out on a date.i...
    wpjpt wpjpt
    56-60, M
    1 Response Sep 17, 2010

    Every Beginning...

    It all starts back to when I was a young boy (about 7?), and of course it started with the intrigue with your mum and sisters intimates. Then as I grew older, I found that it would turn me on until I blow my load, then I went back and would feel guilty, as I thought there was...
    asianxdresser asianxdresser
    1 Response May 6, 2011

    Long Time Dressing

    I have been dressing for many years, I just love the feeling of stockings and panties on my freshly shave body. I also enjoy sharing this with others. I have shared this with some girlfriends in the past with mixed results some good some not so good. I have been luck enough to...
    glorialamuse glorialamuse
    6 Responses Apr 29, 2010

    Extreme Enema Expulsion

    Extreme Enema Expulsion Margaret and Denise had met online, on a site designed for lesbians interested in more "unusual" sorts of sex play, and fetishes. They quickly learned they both had something of a penchant for anal pleasures and were intrigued by the games some like to...
    drn4321 drn4321
    46-50, M
    3 Responses Feb 1, 2011

    Dress As A Woman

    I would like to dress as a woman all the time but i can't so i wear my panties under my jeans all the time i love the feel of them i would like to wear a br to
    tammy2 tammy2
    56-60, M
    4 Responses Jun 6, 2010

    Forced To Dress - Now Loving It

    After my wife and I got married and I got laid off from work. I was just taking it easy since Jan had such a good job. This only lasted a couple of weeks when Jan insisted that I start doing everything around the house that a good wife would do. I truly balked at her...
    robin62 robin62
    26-30, M
    1 Response Jan 7, 2013

    Amy's Story!

    I'm a 28 year old transvestite male. I first became interested in women's clothes at the age of 11, I don't know where it came from and it has confused me for many years. Because it's a taboo subject, I have kept it a secret for a long time, a few girlfriends have found...
    deleted deleted
    10 Responses Mar 30, 2010

    Enema Transgressions 4

    Enema Transgressions "Yeah, fill me up! Fill up my *** with champagne!" she groaned. Nancy and Tina watched the full contents of the bottle empty into Alice's bowels, Alice squealing in delight as she felt the fizzy liquid fill her up. "Here goes," Alice said, expelling...
    drn4321 drn4321
    46-50, M
    Feb 1, 2011

    The River Flows To A Pink Sea

    In my session with my therapist this past Friday, I discussed with her my fears that I will indeed transition to full womanhood, that I feel, I can't avoid it. I had went to a deliverance seminar at my church the weekend before where there was good testimony on demon oppression...
    Ellefem Ellefem
    51-55, T
    2 Responses Jun 30, 2013

    The Secret Is Out

    I have already shared this in I want people to know who I am, but here goes again. I have lived most of my life with a secret that I was always affraid someone would find out. I was born the oldest son, and I had one sister and two brothers. I always knew that I was built...
    colocowgirl colocowgirl
    61-65, F
    5 Responses Mar 15, 2012

    New Title

    Whenever I see a nice sexy looking woman the first thing that pops into my head is "Oh how I wish I could be her, to feel how her clothes caress her soft smooth skin, to know what she's feeling and thinking, and to be so sexy and attractive". Everyone has heard the term MILF...
    51-55, T
    3 Responses Jul 26, 2010

    Enema Transgressions

    Enema Transgressions Tina and Alice had been lovers for almost six months now, after first meeting each other at a dyke bar off-campus one night. Two sleek and frisky Literature majors, they confessed to each other that even though both young and older men had been drooling over...
    drn4321 drn4321
    46-50, M
    Feb 1, 2011


    Some quick background info: I was living in my own for years, and in private I nearly always was wearing women's clothing; however due to some circumstances, I needed to make back in with my parents, and get rid if all my female clothing The problem: I miss it. A lot. The...
    thebunny030 thebunny030
    22-25, M
    2 Responses May 11, 2012

    What I Have On To-day

    To-days hidden clothing while I am out of the house  is a white body shaper no panties & white tights/pantyhose
    xdpaul xdpaul
    56-60, M
    May 24, 2012

    Dressing As A Woman

    To day I am wearing under my my clothing while I write this down at my local library, a looped towel, a black body shaper , no panties, black tights/pantyhose & a red dress which passes for a t-shirt tucked into my trousers
    xdpaul xdpaul
    56-60, M
    May 22, 2012

    What A Weekend

    I new a bunch of crossdressers,one day we were talking and we all decided to go down to a Texas city for a 3 day getaway .I arrived on a Thursday evening rather late so I just went to bed, Friday morning ,my boy clothes were on vacation to ,Connie has come to play so I put them...
    deleted deleted
    Feb 10, 2011

    Dressing As A Woman

    i like dressing as a woman since i was 13 and would dress full time if i could!  i started with the girl next door fully dressing me up as a girl! i soon realise that i was a sissybitch and was further feminised by my first Mistress!! just feel better when in a dress with...
    mandiejune mandiejune
    51-55, M
    1 Response Apr 29, 2010

    Got To Be Me

    I love dressing as a woman. It is so much fun.  I love wearing a bra, panties, girdle, nylon stockings, slip and a  dress with heels.  I have so much fun running about my errands dressed as a woman.I just have to be me.
    jml2000 jml2000
    61-65, M
    Sep 23, 2012

    For the first time in a long,

    long time I finally am able to spend the weekend en femme. Woke up this morning wearing a short chemise and panties. After taking a bath, I did my hair and make-up. Since I then needed to do the happy homemaker routine, I slipped on a thong and cropped jeans, a push-up bra and...
    SandyBG SandyBG
    56-60, T
    3 Responses May 10, 2014

    Nine Years Old Was The Magic Number

    Like so many I started when I was around 9, when my mother put stockings on me because it was so cold that winter going to school. It just didn't come to the surface till 12 years old. That was when my mother caught me in her dress. She paddled me and said she better not ever...
    deleted deleted
    1 Response Dec 25, 2010

    My Guilty Pleasure

    I'm going to start off by saying that i know what I did was wrong, so there's no need to say anything. Anyways, in my second year of university, I was living with four friends, all female. I was always checking out what they were dressed in, andI quite liked it. One afternoon...
    thebunny030 thebunny030
    22-25, M
    1 Response Sep 8, 2011

    Jessica's Return

    It's been almost 10 years since Jessica purged all her femme clothes, shoes, jewelry, wigs, and pics. Just a couple of years ago the urges came back progressively stronger until here I am in 2010 wanting to bring Jessica back to life. I thought I was done with it but I guess I...
    51-55, T
    1 Response Nov 8, 2010

    I often get this urge to dress fully

    as a woman with lingerie, nylons, dress, wig, makeup, heels and accessories. These feminine urges cannot be denied and must be fulfilled, it seems. I dress up at home when I;m alone, but to go get a complete makeover from an expert is a real treat and one which I relish. At...
    DonnaSue10 DonnaSue10
    66-70, M
    2 Responses May 8, 2014

    It Enhances And Extends Me

    Ask any woman if they feel more feminine going out in jeans and a t shirt or a LBD dressed to the 9's. It is psychological. But I do believe it does make most people feel more feminine when they look more feminine. Feminity is an expression of your inner self, my inner...
    Josie06 Josie06
    56-60, F
    3 Responses Jun 24, 2010

    I Just Do

    I don't want to write the cliché story of its great of more options al that's common Knowledge by now . So here is the deal, I like most crossdresser don't suffer and psychological damage or have repressed issues , I dress like a woman because 1.I can 2.Its fun. I just enjoy it...
    mazzz77 mazzz77
    18-21, M
    1 Response Jun 30, 2011

    Moved On To Wearing Makeup

    I've been crossdressing since I was 13-ish. At first, it was just clothes. Nothing more. Then shopping for them was an added thrill. Then telling the sales lady I was shopping for myself (which, by the way, makes the service level skyrocket). This weekend I bought my first bit...
    BlushGreen BlushGreen
    26-30, M
    1 Response Apr 21, 2013
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