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I Enjoy Dressing As a Woman

Personal Stories, Advice, and Support 3,334 People

    I Do!!! - As the name of this group says, I DO! When I get all dolled up it makes me feel like I am a woman. I don’t pass very well but here in my closet I am “Queen for the...
    deleted deleted 26-30 1 Response Aug 13, 2012

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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...
    Margerie Margerie 66-70, M Jul 12, 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...
    deleted deleted 26-30 5 Responses Jul 16, 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...
    jamie50 jamie50 51-55 1 Response Nov 10, 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...
    Officestyle Officestyle 36-40, T 16 Responses Feb 20, 2013

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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...
    phyllisranger phyllisranger 66-70, T 1 Response Apr 19, 2013

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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...
    boitoy4wife boitoy4wife 26-30, M 29 Responses Aug 25, 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...
    anitasue22 anitasue22 26-30 5 Responses Dec 18, 2010

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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. ...
    Raeka Raeka 36-40, T 11 Responses Apr 29, 2010

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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...
    louisestjohn1 louisestjohn1 61-65, M 7 Responses Nov 16, 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...
    steve1016 steve1016 31-35, M Aug 9, 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...
    cdjo cdjo 41-45, M 3 Responses Jan 19

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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...
    deleted deleted 26-30 Jul 18, 2013

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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...
    smitha19802002 smitha19802002 31-35, M 3 Responses May 8, 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...
    HighheelWendy HighheelWendy 41-45, M 6 Responses Jan 9

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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...
    AmandaJosefine AmandaJosefine 18-21, M 5 Responses Aug 14, 2013

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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 1 Response Jan 5

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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...
    honeypot612002 honeypot612002 51-55, T 13 Responses Oct 5, 2009

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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...
    amandasilvers69 amandasilvers69 41-45, T 13 Responses Jul 15, 2011

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    Just Spent Several Hours Dressing, Taking Pictures And Posting Them On EP - It's crazy how much I enjoy that!
    jenniferoccasionally jenniferoccasionally 46-50 11 Responses Jun 8, 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...
    caits111 caits111 22-25, F 144 Responses Oct 11, 2009

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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...
    wetrev wetrev 46-50, M 11 Responses Apr 14, 2011

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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...
    christinexxy christinexxy 56-60, T 1 Response May 4, 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...
    Sugarbush44 Sugarbush44 41-45 2 Responses Jun 29, 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...
    deleted deleted 26-30 7 Responses Mar 20, 2013

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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...
    Sugarbush44 Sugarbush44 41-45 Jul 3, 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...
    TVCassandraSlut TVCassandraSlut 22-25, T 4 Responses Aug 4, 2013

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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...
    RunAroundSusan RunAroundSusan 22-25 Apr 20, 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...
    deleted deleted 26-30 May 3, 2013

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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...
    KEERTHICDR KEERTHICDR 18-21 1 Response Aug 19, 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...
    genivieveleduc genivieveleduc 46-50, T 5 Responses Mar 17, 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...
    wendym99x wendym99x 61-65 1 Response May 30, 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...
    MiaFoxy33 MiaFoxy33 31-35, F 3 Responses Sep 16, 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...
    randydad randydad 61-65 1 Response May 3, 2013

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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...
    paula3198 paula3198 46-50, F 11 Responses Jul 23, 2011

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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...
    Ellefem Ellefem 46-50, T 10 Responses Sep 5, 2012

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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...
    davis36a davis36a 61-65 8 Responses Jan 28, 2012

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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...
    pat85 pat85 56-60, M 17 Responses Jan 3, 2011

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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...
    scaff69 scaff69 36-40 1 Response Aug 12, 2012

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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...
    deleted deleted 26-30 10 Responses Oct 23, 2009

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    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...
    Margerie Margerie 66-70, M Jul 11, 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...
    caligurlx421 caligurlx421 18-21, T 9 Responses Jul 29, 2012

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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...
    aprildaynes aprildaynes 61-65, M 17 Responses Mar 20, 2008

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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...
    Bthegirl Bthegirl 26-30, M Apr 29, 2013

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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...
    Trisha60ts Trisha60ts 61-65, T 2 Responses Mar 23

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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...
    Officestyle Officestyle 36-40, T 5 Responses Jun 15, 2013

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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...
    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...
    deleted deleted 26-30 3 Responses Apr 22, 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...
    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...
    Victoriafinally Victoriafinally 66-70, T 8 Responses Nov 30, 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...
    ashleigh83 ashleigh83 41-45 6 Responses Aug 13, 2011