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I Love to Cross Dress

Personal Stories, Advice, and Support 1,295 People

    My New Hobby

    Yesterday I bought myself a realistic you-know-what, just under 7 inches long and 2 1/2 inches thick. And is it ever gorgeous! So I got dressed up in my baby dolls, G-string, black bra and high heel shoes and started practicing my sucking technique, and I must say I was ok for...
    FrauleinKarla FrauleinKarla 61-65, F 1 Response Aug 7, 2013

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    It'S A Back To School Night, Can You Turn Up Dressed As A Schoolgirl?

    This was posed to me one evening by a critics daughter. Another theme night & I'm being asked to dress up. I hit the thrift shops & come up with an outfit that looks good , possibly something to do with 6" heels & large earrings, don't all schoogirls wear these, put on my makeup...
    Cherridarling Cherridarling 51-55, M 2 Responses Jun 17, 2013

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    Almost all of the clothes I dress in

    and that you see in my pictures belong to my girlfriend and her sister. Her sister doesn't know though... Shhhh(;
    sammixdress sammixdress 18-21, M 3 Responses Jun 18

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    1st Crossdress Love Story Of 2013

    I am really shocked a I love to cross dress story has not been posted in 2013 I love to cross dress, it is simple to do, relaxing and can make you look so pretty. The best part about cross dressing is you can become whomever you desire to be, a sweet girl, or a not so...
    sweetpeaDeby sweetpeaDeby 18-21, M 3 Responses Apr 20, 2013

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    Fabulous.

    I'd love to have cross dressing friends. Honestly, they're fabulous! And would be so much fun as friends. I've always wanted to have a sleepover with a cross dresser and let him do my makeup and pick out my outfit. That'd be awesome c: I just wanted to share that :D
    JustCammy JustCammy 16-17, F 1 Response Oct 15, 2013

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    First Video Chat

    Omg, just had my first video chat. He's a striaght guy and love the way I look. I did 2 different outfits...and dance on camera like a ********. I think I'm ready to go out dress.lol
    Jedimindtrick39 Jedimindtrick39 36-40 8 Responses Aug 17, 2013

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    I am a feminine man and am attracted to women,

    but I love women's clothing, especially bras as I find them feminine... When I first brought & wore a Victoria's Secret bra, I loved it. I felt so relaxing, cute, sexy, and feminine. Since then, I began to love crossdressing and shop for women's clothing, make-up, etc. By now, I...
    deleted deleted 26-30 4 Responses Feb 9

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    Late Developing Cross Dresser

    After 40 odd years in the wilderness I discovered cross dressing some 2 years ago ( a female friend who emigrated left some clothes here, and I had to try them on). While I accept I'll never be (and on some days don't want to be) a passable women, I just love wearing womens...
    biguybyc biguybyc 51-55, M Nov 17, 2012

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    Preface: My wife and I are having problems,

    separately from my secret cross dressing. She has no idea I do this. Last week I stayed at a motel to give us space. Big blow out fight. I was really happy to do this because I knew I would have a chance to spend the night as Alexis. I checked into a decent but kinda shady...
    Alexissmith Alexissmith 36-40, M 10 Responses Mar 9

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    The Day I Was A Girl

    it was the month of march when there was holidays .... i went on alone for a tour to ooty.the main reason i went there was to be a women the whole time.i biught big busty K sized breast forms and all the indian and western kind of cloths. i got into a htel room,took a bath and...
    lathakumar lathakumar 22-25 1 Response May 29, 2013

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    Being off today gave me another opportunity of

    going en femme for the day. One of my stops took me to a Laser Hair removal office. I had been concentrating on my facial hair for the last year, and a couple of more visits should rid my face of any facial hair and the need to shave. The people who run the office are very...
    SweetRhonda SweetRhonda 51-55, T 1 Response Sep 5

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    My Crossdressing

    my crossdressingstarted at about six years old i tried any women clothing i could findlater became easier as i have 2 sistersone three years younger the other 9 years younger so i could pick there clothes up put them on when they were not looking i also player games with them...
    raysst raysst 61-65, M 2 Responses Jan 14, 2012

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    It seems that the more I get dressed up

    as a girl, the more I feel like I am a real girl. Putting on my bra, panties, wig, and make up makes me feel like a woman. Then slipping in to a skirt and blouse or a pretty dress completes my feminization. I feel more like a woman every day. I think I could dress 24/7 if I...
    RandiHill RandiHill 51-55, M 3 Responses Aug 11

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    This Is Time For Prayer !

    The Energy takes over I open the hidden shelve and take out the white bra and two yellow balls and wear it body starts vibrating with energy the yellow balls becomes my breasts I look into the big mirror and enjoy my own boobs now this is the time to go on bed with my eyes...
    shikhasiss shikhasiss 46-50, M Dec 21, 2012

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    How I Became Fraulein Karla Liebrandt

    Hello, my name is Karla Liebrandt and here is how I transformed into this alter ego. I am actually a man who loves dressing up as a woman and wearing long hair. This all started innocently enough when I went out on Hallowe'en night of 2011 with my niece. She went as a wizard and...
    FrauleinKarla FrauleinKarla 61-65, F 5 Responses Aug 6, 2013

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    Cross Dress

    I always love panties and heels and dress and *** my *** with toys I always wanted to be a gurl
    richie82 richie82 22-25, M 2 Responses Jul 21, 2013

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    Pants And Skirt Outfits

    I have a number of matching pants and skirt outfits, and as long as I don't make the colors clash, cross dressing is not only fun, but saves a lot of money on having to buy new outfits. It's so easy to just take matching sets and see what skirt or pants goes with what blouse or...
    eleanorssong eleanorssong 56-60, F 5 Responses Nov 15, 2011

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    Hi Everyone , I wanted to explain a little bit

    on how I've been feeling lately towards a few different things. First I've kinda come out as a Cross-Dresser , I love wearing women's clothes , but not fully going out as a women. In that case I consider myself Androgynous , because I love the feeling & dressing like a guy & a...
    ThinkDiff ThinkDiff 18-21, M 4 Responses Sep 9

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    Yes, Its True

    I love being me! That includes dressing as me. Society may call it one thing but in my heart-of-hearts I know. I am just being myself. A woman.  
    Josie06 Josie06 56-60, F 2 Responses Oct 24, 2011

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    Male to Female unable to stop cross dressing urge

    Hello Forum - I recently posted 10/23/2009 sharing how I began living totally as a women discarding every bit of men's clothing and affects I 'd owned on New Years Day 2005.  NOW I'm going to share my story of how and why I got myself into becoming...
    sandradorothy sandradorothy 56-60 2 Responses Oct 24, 2009

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    I'm a cross dresser and I'm afraid to wear my

    girl's clothes in front of people I know.
    njames597 njames597 18-21 6 Responses Jun 4

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    i love to wear girls cloalthes i love the

    feeling the bra up aginst my boobs the feeling i get from the bra
    azza3421 azza3421 18-21, M 1 Response Aug 11

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    Wife Loves Me To Cross Dress,

    My wife loves for me to cross dress, Im the woman she is the man, she loves her strap on and I love it to
    charlett charlett 51-55, M 3 Responses Sep 5, 2013

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    Every Single Day

    I love to crossdress because that is when I feel complete. So much of life is going around being what other people want you to be. At work they want us men to be dressed in pants, skirts, and clod hopper shoes. When truly inside you want wear a dress, panty hose, and high heels...
    Adam59 Adam59 56-60, M Dec 13, 2012

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    Being off today because of Labor Day is giving

    me the opportunity to wear one of my favorite country and western outfits - a green prairie skirt with red and gold ribbons and a red chiffon blouse. My wife helped me a bit by touching up my makeup and fixing my wig. I'm loving it right now! At lunch time will go out to get...
    SweetRhonda SweetRhonda 51-55, T 2 Responses Sep 1

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    The Things I Love About Being A Woman

    Here are a few favourite things I love about being a woman. One is wearing my hair LONG. My hair just touches my bum and it feels so wonderful against my back! To look at myself in the mirror as I brush my lengthy mane is so arousing. It is so thick and silky and looong! I love...
    FrauleinKarla FrauleinKarla 61-65, F 1 Response Aug 16, 2013

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    From Ugly Duckling Into A Beautiful Swan.

    I first started to crossdress when my local sporting club had a theme night. I cant remember what the theme was but I decided that this club needed a drag queen. This started a passion In me to create a character called Cherridarling . Since this night I have done many such...
    Cherridarling Cherridarling 51-55, M 1 Response Jun 6, 2013

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    Haloween: Moms Pissed

    Well I said it. Last year I was a girl for haloween. This year I'm doing the same thing and my mom is mad. On one hand, her job is stressful and a lot of days she comes home from work angry at everyone and very cranky. This could be one of those days. On the other...
    SilverDragon419 SilverDragon419 16-17, T 6 Responses Oct 30, 2009

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    fercrox fercrox 46-50, M Apr 6

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    Yard Sale Work Jeans

    My now 4th ex wife was out yard saleing one day & picked up some used jeans for me as at the time I was building pole barns in North Eastern Arkansas & that job can be rough on clothes. When I got home & she presented them to me the first thing I did was check the size. They were...
    tinymuel tinymuel 46-50 5 Responses Dec 25, 2011

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    I have been researching gloryholes

    and am thinking of doing one dressed tomorrow. Any thoughts or advice ?
    Jess967 Jess967 18-21, M 3 Responses Apr 8

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    Funny Reations

    I love making people fell awkard.I am a full time crossdresser and i love a little fun. 1.I went to victoria street and i asked for a bra fitting!I knew which size bra i was but i wanted to make the sales girl feel awkard. 2.I went to the local pool and said i "forgot" my...
    deleted deleted 26-30 Feb 13, 2013

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    The sporting club that I am a member of held a

    goods and services auction a couple of weeks ago with donations from various people around the club. Two enterprising young chaps put themselves up as a double date as their contribution for the auction, however those that organised it thought that they could have done better...
    Cherridarling Cherridarling 51-55, M 3 Responses Aug 14

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    Need help with what to wear

    and buy !!!! Message me x
    xdresses xdresses 18-21, M 4 Responses Jun 21

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    The Highs & Lows Of A Country Town Crossdresser

    The fear of assault is something always in the back of my mind when I go out "dressed" to my local sporting club theme nights. I was asked if I would "frock up" for the footy club's annual ball several years ago & I was assured I would be okay. I wore a long gold ballgown & big...
    Cherridarling Cherridarling 51-55, M Oct 28, 2013

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    First Time In Pulbic

    I finally told a close friend of mine about me wanting to become a girl. She loved the idea and said we have to go shopping. I was so excited but so scared cause it would be the first time i went out in public in girls clothes. I didn't have any makeup at the time tho. : ( I only...
    girlyboy9 girlyboy9 18-21, M 4 Responses Oct 19, 2012

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    Girl's Jeans Again - The Best Disguise!

    I usually buy women's jeans at Wal-Mart - "LEI" brand, "Rider," "Signature," "Miss Tina," "Faded Glory," and others.  If I can get them in a 6T that works best.  But I need the length for most circumstances, so I get 8T if that is the smallest tall size.  I have some 4 & 6...
    Falecia0 Falecia0 61-65 4 Responses Aug 18, 2012

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    Girly Clothes In My "Other" Tool Case

    Several years ago, in keeping with my long standing tradition of taking my femme self on the sales road with me, I had the good fortune to work as a technical service representative for a motor coach company. My job was to replace computer controlled shock absorbers, and then...
    joseygurl23 joseygurl23 56-60 3 Responses Sep 17, 2013

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    Related Experiences

    Yesterday, my niece called me to let me know she was going to the bar she first saw me dressed up as a woman. It is ladies' night on Wednesdays at this bar. She invited me, as...
    SweetRhonda SweetRhonda 51-55, T 1 Response Sep 11

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    I have now lost nearly fifty pounds just this year and needed smaller clothing. I went back to the Layne Bryant store and fond the same sales lady, Ruth< and she so willingly...
    Varience Varience 70+, M Sep 1

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    I was cross dressed as an infant ??? During an extended stay with the sweetest human soul to that I have ever known (Gramma Minnie), I learned that my mother used to dress me as a...
    JessicaDale JessicaDale 51-55, T 2 Responses Sep 5

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    I absolutely love the fetishistic experience of cross-dressing....I would love it more if I could share it with another male...I never had the courage to admit this
    deleted deleted 26-30 2 Responses 3 days ago

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    I cross dress in leather...boots jackets pants skirts.
    leatherx leatherx 26-30, M 3 Responses 16 hrs ago

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    I love to cross dress and wher pull-ups but nobody knows
    Poshopads99 Poshopads99 13-15, M 2 Responses Sep 13

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    I have been confused lately and I need someone there for me I know there are plenty of people online but that's not enough for me I need someone in person to speak with dress with...
    JulieCakes JulieCakes 13-15, M 1 Response Sep 3

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    I had a great experience yesterday, I went out in a dress/bra /panties etc. I put on a drress with bra and panties, and went to the drive through. I did not put any make up on...
    mostlynatalie mostlynatalie 31-35, F 4 Responses Sep 9

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    I havent dressed in a while. I can hold in the urge of stepping into a pair of panties and pantyhose when i'm with my girlfriend and i get to do certain things with her:) but at...
    CDMichelle16 CDMichelle16 18-21 3 Responses Sep 3

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    My mother and aunts put panties on me when I wet my pants.I was 6 years old and remember they all laughed.I liked the attention and wanted to wear them all the time.My mother didn...
    edz21054 edz21054 36-40, M Sep 11

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    I just got in bed after slipping on my pink and black lace panties and matching strapless bra with my blue thigh length layered party dress. it's been a good night
    CDMichelle16 CDMichelle16 18-21 5 days ago

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    has anyone ever once,,,,,,seen a woman well dressed up or in casual clothes,,that looked hot ....and standing near them ....realize you might fit in what she has on,,,,,the the...
    zoner303 zoner303 51-55, M 5 Responses a week ago

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    So today has been a good day I am home alone for the rest of the week,and I get to dress up like I am pregnant which makes me so happy sleep in my belly wake up in my belly do...
    Iwannbeafemalewhoispregnant Iwannbeafemalewhoispregnant 18-21, M 1 Response Aug 23

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    on a cruise ship it's nice to dress up a little for dinner
    BettyLavender BettyLavender 61-65, F 1 Response