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I Enjoy Dressing As a Woman

Personal Stories, Advice, and Support 3,346 People

    Dressing In Womens Cloths

    Have for yesrs been dressing on womens cloths.1/ because I like to 2/ because of the feel good aspect 3/ because of the choice and colours. Lwear underwear on most days particularly in the cool or colder weather. Ladies rainwear has always been a passion. In the past satinett...
    Margerie Margerie 66-70, M Jul 11, 2013

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    Dressing As A Women

    I have always enjoyed as a women. It all started when I was a pre-teen and really took of when I was a teenager. I can remember putting on my mothers black dress and wearing whatever else I could find. Normally bra, ,black panties, girdle, slip and pantyhose. I was just new to...
    deleted deleted 26-30 May 3, 2013

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    I love dressing and going out in public

    as a women. I do it when I travel on business. I let my guard down when travel. I do things that I normally wouldn't do in the city that I do. I love trying on clothes and shoes in the stores and never had a bad experience doing that.
    cdjo cdjo 41-45, M 3 Responses Jan 19

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    Bridal Shower

    My wife is out for the day at a friend's bridal shower. Since she's at an event where all the ladies have dressed up in skirts or dresses and heels - I thought I would take the opportunity to do the same as if I was also attending. Today I have on a white floral print...
    scaff69 scaff69 36-40 1 Response Aug 12, 2012

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    There are so many of us out there searching

    for happiness convinced that we would find it in womanhood. For a very few, some who are truly transsexuals – woman trapped in a man’s body -- they do find happiness. For too many others it was but an empty illusion. Cross dressers often experience such joy in the female...
    Trisha60ts Trisha60ts 61-65, T 2 Responses Mar 23

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    The Second Stage

    It wasn’t until I was married several years with 2 kids, a house, a career, and a second job in the army reserves that my next stage of cross dressing occurred. I was traveling in a 2 ½ ton army truck with parachutes on a training weekend reading girlie magazines.  I came to...
    phyllisranger phyllisranger 66-70, T 1 Response Apr 19, 2013

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    Love Long Dresses

    I just wanted to say that I love long dresses with a zipper in the back and all that lovey lingerie under it. I feel very girly and lady like when I am all dolled up like that. I sometimes think about being at a party or a night club and would someone try to run there hands up...
    cindyslip cindyslip 46-50 17 Responses Aug 4, 2011

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    Dressing in matching bra

    and panties, thigh highs and heels. Dress or a skirt and sexy tops is what I like. I also love shopping for my clothes and trying them on in the stores.
    cdjo cdjo 41-45, M Jan 5

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    Me In My Sisters Prom Dress!

    So a couple of weeks ago I was alone at home for a couple of days... So I went nuts, I recorded alot of crossdressing videos and have been uploading them when ever I get the time and internet is not being used! One of the videos was me in my sisters prom dress!! And yes it felt...
    AmandaJosefine AmandaJosefine 18-21, M 8 Responses Aug 14, 2013

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    Shopping Turns Dirty

    Wife took me shopping last night. We wound up at a little women clothing shop. My wife held up a pair of panties, "Bet you would look cute in these" a little too loud for me, The salesgirl and a young man both turned and looked. The man (Carl) spoke up and said "Lets see, try...
    deleted deleted 26-30 7 Responses Mar 20, 2013

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    Luxury Of Silk

    I can remember the first time I put on a pair of Mums panties. I was alone in the house, Mum and Dad out, very quiet. I went into Mums bedroom, can still remember how I always loved the room, it always smelled with delicious Chantilly perfume, so feminine. I open the dressing...
    Sugarbush44 Sugarbush44 41-45 2 Responses Jun 29, 2013

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    The Night Out - .... Happens

    Nice september evening in Sarajevo, little chilly with breeze. I was alone at home, bored till death so I decided to go dress-up, make-up and to go out little bit. Cause i'm shaved regulary I didnt need depilation now, so I just took shower and put some nice hydration lotion...
    MiaFoxy33 MiaFoxy33 31-35, F 3 Responses Sep 16, 2013

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    Cable Guy

    I was just finishing my makeup and hair and glueing on my 38dd breastforms and had a knock o the door. I wrapped in a robe and went and looked out peephole and asked who it was,he replied Cable man. I opened door and asked the problem. He said an upgrade that would take an hour...
    amandasilvers69 amandasilvers69 41-45, T 13 Responses Jul 15, 2011

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    I Enjoyed A Lot As Woman

    i am from small village, about me i am comfortable as woman body,hips, softner body, pure white color, looks like girl, woman character dominating on me. after complete 10th class exams i went my mami aunty house at hyderabad dilshuknagar, mu uncle working in dubai mami staying...
    smitha19802002 smitha19802002 31-35, M 4 Responses May 8, 2013

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    Surfer Girl On St. Paddy'S Eve

    Last night being St. Paddy's Eve, I found myself at home and no real plans. I was listening to music and felt like dancing, so I showered, shaved my legs, put on some make-up and began looking for a green dress. Turns out, green is not super common in my wardrobe, but did have...
    genivieveleduc genivieveleduc 46-50, T 5 Responses Mar 17, 2013

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    Pretty Dress

    i enjoy dressing as a woman so much that i can over come my fear of what people Will say or think about me if i shop for dresses alone. which i just did Saturday. i went to several stores and looked around at woman's clothes. it felt great and i was scared  to...
    honeypot612002 honeypot612002 51-55, T 13 Responses Oct 5, 2009

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    My First Time Cross Dressing Part2

    HI FRIENDS THANK U FOR MY PREVIOUS STORY COMMENTS. HERE IS MY CONTINUATION FOR MY PART 1 ,,,. MY MOM BOUGHT TWO NIGHTIES FOR HER, BUT WORING NIGHTIES IS NEW FOR HER SO SHE WAS UNCOMFORTABLE WITH THAT NIGHTIES AND SO SHE KEEP IT IN THE WARDROBE WITHOUT USING IT ANYMORE. ONE DAY MY...
    KEERTHICDR KEERTHICDR 18-21 1 Response Aug 19, 2013

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    I Love Guys That Dress Like Women

     i am a girl, so i really do enjoy dressing as a women, but seriously, cross dressing boys are so hot, I love guys in bright lipsticks and old school dresses, they drive me nuts. they way they try and walk in heels, and watching them try and put lipstick on  oh so...
    caits111 caits111 22-25, F 148 Responses Oct 11, 2009

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    My Coming Out

    Just the thought of dressing up gets me excited. It's a very sensual feeling for me. I love everything about women, the way they look (every curve), feel and smell. Being dressed up bring that feeling closer. The best part is, my wife enjoys it when I dress up. The sex is...
    deleted deleted 26-30 10 Responses Oct 23, 2009

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    So Much So

    I so much enjoyed-enjoy dressing as a woman that I accepted the opportunity to dress full time when my wife ask if I wanted my body altered to be more like a woman. Just on top and some work on the hips, and bottom I said yes.  After it was all done I loved my body, but then...
    RunAroundSusan RunAroundSusan 22-25 Apr 20, 2013

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    Stirrup Pants

    I have always enjoyed dressing up and wearing all the cute skirts, dresses, gowns and short shorts. But I usually change my dressing habits with the season, and with winter shortly upon us, it is time to break out my winter clothing.One of my favorite things to wear is Stirrup...
    jamie50 jamie50 51-55 1 Response Nov 10, 2013

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    Or I Wouldn't Be A T-girl ....

    I love shaving my legs, my arms, smelly baths, doing my hair, putting on makeup and perfume, putting on slutty clothes and high heels..... I love walking like a woman, talking like a woman, acting like a woman..... Yep......Love the whole lot about dressing like a woman...
    TVCassandraSlut TVCassandraSlut 26-30, T 3 Responses Aug 4, 2013

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    My Story

    My story starts like many other's you probably have heard i was 12 when i first found that special pair of panties in my aunts dresser it was love at first sight when i put them on i knew then this was going to be something that i would love for a very long time as i grew it...
    stacyhopes stacyhopes 31-35, M 7 Responses Dec 9, 2010

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    Sissy Hubby For Wifes Pleasure

    For the Pleasure of my Wife i have submitted to Her need to sissfy me, humilate me, and treat me like her submissive gurly boi even before we got married. i have worn only panties since before our marriage and i wear women's casual clothing around the house. She has shown me...
    boitoy4wife boitoy4wife 26-30, M 30 Responses Aug 25, 2013

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    I Enjoy Dressing As A Women

    There are a number of reasons why I like wearing womens cloths. I feel you ha ve more freedom , you are more confortable, you have a greater selection of cloths and the colous have no end. It make you feel real good when a women says you look good in s dress or skirt an blouse...
    Margerie Margerie 66-70, M Jul 12, 2013

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    I Do Enjoy Looking With Envy

    I'm a girl watcher, when I see an attractive women I can't take my eyes off of her and yet try not to be obvious about it. The thought of sex never enters my mind. It's about her clothes and the body I don't have, the style and how they fit. It's more envy, cute tennis outfits in...
    wendym99x wendym99x 61-65 1 Response May 30, 2013

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    Feeling Womanly

    yes, I'm a crossdresser/mtf transgender. I like to dress as a woman.  It can be just shorts and a top, oh and yes a bra and panties too. Makes me feel very feminine and sexy.  Calms me down make me feel in tune with who I am.  It can be very difficult to go back to male mode...
    Ellefem Ellefem 46-50, T 10 Responses Sep 5, 2012

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    The Big Thrill

    The biggest thrill for me is wearing my breast forms that make me feel like a women.  The clothes are the icing on the cake.
    phyllisranger phyllisranger 66-70, T 1 Response Apr 18, 2013

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    Work From Home

    One day last week I worked from home dressed as a woman. It felt nice to get up and primp for work, I wore a matching bra and panty set, stockings, a cute black dress, and high heels. It was a happy and productive day.
    ashleigh83 ashleigh83 41-45 6 Responses Aug 13, 2011

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    The Woman Inside Me

    I've enjoyed dressing in female clothes since my teenage years when I used to put on my mother's clothes when I was alone in the house. I started going out for walks dressed as a girl and the habit has remained ever since. Now, I'm 60 but feel much younger and always enjoy...
    aprildaynes aprildaynes 61-65, M 17 Responses Mar 20, 2008

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    IdleThoughts Of A Crossdressing Vicar (yes - A Vicar)

    I really enjoy dressing as a women but do not have the nerve to go out dressed - feel I am a bit too old and ugly for that these days! My wife enjoys it when I am dressed and helps me find the right outfits. I try to dress my age (48) and style (casual) so tend to go for jumper...
    wetrev wetrev 46-50, M 11 Responses Apr 14, 2011

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    Pretty Things

    I enjoy dressing as a woman everyday.  Women have more colorful clothes than men. Take pink for instance. a very feminine color,not many men wear pink.  Womans clothes have frills and lace.  They have sequins and beads.  The materials used in clothes are...
    Raeka Raeka 36-40, T 11 Responses Apr 29, 2010

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    Bubba

    im a man who likes to get dressed up i feel sexy when i do short skirts and dresses would liker to find a girl that would like to play dress up with a girl but would like guy if he wants to
    steve1016 steve1016 31-35, M Aug 9, 2013

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    Yepp Me Too

    the feelings i get when i dress up just makes me feel content and so fulfilled. idk but crossdressing to me is like a drug or an outlet...it relieves stress and makes me feel so happy, letting go of all my ambitions~! its sum wat of a rush for me especially because no one knows...
    caligurlx421 caligurlx421 18-21, T 11 Responses Jul 29, 2012

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    Find Me The Next Morning

    It was a late party. My boyfriend has gone out for the day. I'm standing at the sink gazing out at the pool. I've showered and made up my face. Hugging my body is a satin magenta sleepshirt. It's short enough that my pantyline peeks out from the hem. As I stand there, I think...
    Officestyle Officestyle 36-40, T 5 Responses Jun 15, 2013

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    What A Discovery

    I love dressing-up. Wearing panties, lipstick and perfume.  I love it.  I am so happy.  It feels so freeing.  So sensual, so sexy.  I call myself a hermaphrodite.I am still 100% male with masculine desires for women.  Yet, I also love experienceing the feminine side, and...
    randydad randydad 61-65 1 Response May 3, 2013

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    My Favorite Thing

    It is my highest desire when I slip on my panties, fasten my bra and slip a silky chemise on. I fix my makeup and hair. Then I put on a sexy garter belt, pull the straps under my panties. I attach my stockings. Next I wiggle into a slick dress and step into my heels. I'm ready
    Officestyle Officestyle 36-40, T 16 Responses Feb 20, 2013

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    Wondering

    Wondering if many woman. See why men wears female clothing for one they feel great pantys all diffrent types thongs g strings cheeks bathingsuits. I don't know why but wearing skirts is great I like them feel so free I like wearing female jeans and yoga pants you woman get to...
    Bthegirl Bthegirl 26-30, M Apr 29, 2013

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    Forced Maid

    I was forced by my girlfriend to become her french maid and ndertook all her domestic chores and those of her mother. I was forced in to a short black satin uniform, a tightly laced black satin coset, matching lacy bra, black frilly satin panties, black seamed stockings and 62...
    anitasue22 anitasue22 26-30 5 Responses Dec 18, 2010

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    Living A Secret

    It all started when  was about 10 I whent to live with my aunty as my dad had deid and my mothere whent into hospital.I had to shire the bed with a cousan 8 years older.One of his games was to take a pair of his mothers knickers and get me to weare them while in bed They where...
    pat85 pat85 56-60, M 17 Responses Jan 3, 2011

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    The Begining

    I was in junior high school when I first notice the high school friends of my sister when they visited. I remember they had the tight skirts and sweaters and blouses that showed their blossoming busts and swinging hips.  My groin seemed to get hot and almost explode just...
    phyllisranger phyllisranger 66-70, T 1 Response Apr 18, 2013

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    Watching What I Do!

    Oooops is all I could say this morning. After spending about 90% of my waking time this weekend as Diane and loving every minute of it I almost made what would have been an exciting mistake, to say the least. The weekends allow me the pleasure of waking and starting my day as...
    deleted deleted 26-30 3 Responses Apr 22, 2013

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    I am a 42 yr old straight guy

    but i love dressing as a woman. It started at a young age & been dressing on & off ever since. The last 5 yrs my crossdressing has really been intensed. I'm not sure what or why it is but i have really been in touch with my feminine side. I love the feeling after shaving my legs...
    HighheelWendy HighheelWendy 41-45, M 7 Responses Jan 9

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    If I Wasn'T Dressed As A Woman I Would Be Naked...

    To me, dressing as a woman isn't a fetish or a turn on.. Its a necessity. I feel better, look better and am more active when I put the time into myself to look good. Not to mention my breast bother the crap out of me unless they are encased in a bra to stop them from bouncing...
    christinexxy christinexxy 56-60, T 1 Response May 4, 2013

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    While She's Gone

    i am married and my wife doesn't know it... every time i can, when she goes to school on tuesdays and thursdays at 7pm, that's the moment i do it, i get into her closet, choose some nice high heels, a skirt and my secretly hidden stockings and i come out as the real me, i love to...
    deleted deleted 26-30 5 Responses Jul 16, 2013

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    Story Of That Night

    Me And My Life By: Me Written on July 17th, 2013 I was around 15 years old.One day I had gone to my friends house to complit my home work given by school.It was around 11pm.I told to my friend to get sleep.tomorrow we will do.Then we slept.In the mean time my friend had some bad...
    deleted deleted 26-30 Jul 18, 2013

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    Can't Wait

    I was out at the mall yesterday picking up a few things. I was not planning on buying any clothes. I went into a store to find a new pillow. I walked by the women's clothing section where I found a black and white color block sweater dress. I stopped to look at it and ended up...
    cdjo cdjo 41-45, M 4 Responses Oct 14, 2013

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    A Night To Remember

    My second time out fully fem to a CD club was quite memorable. I wore a black pencil skirt that rested just above the knee with a red satin blouse. Of course proper undergarments with a gaff to keep my girly presentation proper, c cup silicon forms, shoulder length wavy blond wig...
    Victoriafinally Victoriafinally 66-70, T 9 Responses Nov 30, 2013

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    "relaxation"

    For me, dressing up as a woman is a way for me to relax. I realize that might sound funny, because I am always worried about getting caught. Once I start the transformation, I start to feel like I am a real woman. I enjoy the feeling of the nylons covering my legs and the...
    davis36a davis36a 61-65 8 Responses Jan 28, 2012

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    How Else Would I Dress?

    I am a woman that is trapped in a male body. I wear panties and bras every day and when not at work skirts, tops and in summer dresses.. For me its perfectly natural for me to do this. I can pass as the expression goes if I take care with my looks (wearing make up)and  I sleep...
    paula3198 paula3198 46-50, F 12 Responses Jul 23, 2011

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    Luxuriating In A Sari

    There is a very lovely Indian lady that works in one on the West of England's bigger stores. I have always liked working with her, we seemed to 'gell' at once. She had no doubts, no worries, no concerns about me. Sometimes being treated as an equal, as a woman, doesn't happen...
    Sugarbush44 Sugarbush44 41-45 Jul 3, 2013

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    Dressing As A Girl Is A Turn On Greater Than A Climax

    I was only 8 or 9 the first time I felt the nylon on my skin. The feeling was so strong I could not explain it. I needed to feel it as often as possible. I reflect on it today and realize that it is like a drug.When my mother was not looking I would run through her silky drawer...
    louisestjohn1 louisestjohn1 61-65, M 7 Responses Nov 16, 2010

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    harley80cu harley80cu 41-45, M 1 Response Jul 8