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I Love to Cross Dress

Personal Stories, Advice, and Support 1,440 People

    One time I got all dressed up

    and tied myself up. After a bit I tried to untie myself and I couldn't my hands were tied to my feet and I was scared . I thought what if I can't get out I'm fully crossdressed even stuffed my bra as I struggled to get free I realized I might be unable to get out idk why but...
    deleted deleted 26-30 1 Response Feb 21

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    I love to be in bridal dress in my room!

    I love to wear saree blouse in Wich back open sexy type blouse.
    Anjumsultana Anjumsultana 36-40, F Jun 8

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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
    KatrinaBoyer41 KatrinaBoyer41 41-45 8 Responses Aug 17, 2013

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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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    I'm in a place right

    now where it is literally IMPOSSIBLE to be me...I can't even have any of MY things here, can't get away, all I can do for now is remember, dream, and wait until my situation changes...
    Allysoninaz Allysoninaz 46-50 4 Responses Apr 29

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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 7 Responses Sep 9, 2014

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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 5 Responses Jun 4, 2014

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    Today i cross dressed in high heels

    and a dress it felt amazing and if anyone wants to hate go away and go do something productive.
    IwantoCrossdress IwantoCrossdress 13-15, M 1 Response Nov 2, 2014

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    i went out last night with a corset mini skirt

    and boots it was so much fun I asked one of the girls that worked there if they would take a photo as i brought a camera for that She must have had as much fun as i she took 30 photos
    jerbare jerbare 61-65, M 4 Responses Mar 3

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    I got a loose style blue skirt

    that extends past my knees the other day what length should I have it cut down to? 11 inches, or shorter than 11 inches or longer than 11 inches. I had an 11 inch skirt a while ago before someone stole it from experience I couldn't bend over with out showing off my big bubble...
    Donpi Donpi 22-25, T Dec 17, 2014

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    I am a Married CD/TV.

    I made my wife to be very aware of this before we were married. For a while she was having fun with it and even used *****'s and vibes on me at times. Then the strap on was introduced but not long after that she lost interest it it 19 years later and were still together with 3...
    tammysometimes tammysometimes 46-50, T 1 Response Oct 5, 2014

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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
    deleted deleted 26-30 2 Responses Oct 15, 2013

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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 56-60, M 3 Responses Sep 5, 2013

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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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    Msg me some dares ill dress up

    for you and do any dare you tell me;) ill send pics proving I did dare ;) anything except telling or showing people I cross dress unless its a complete stranger lol
    deleted deleted 26-30 1 Response Feb 21

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    I love to wear mens clothing

    and I'm a girl. I feel more comfortable this way, more true to myself. I love expensive men's clothing, shoes, and accessories. It's pretty easy to get hand me downs. I have a thirteen year old brother who is growing so fast! (Already taller, stouter, and heavier than I am.) He...
    Annaelaine Annaelaine 16-17, F 3 Responses Dec 9, 2014

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    Male 34 frm hyd looking

    for cd! Friend how care me and dress me up and sexy bride for the day.olny caring people male or female intreasted than only message me
    Anjumsultana Anjumsultana 36-40, F Jun 7

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    jerbare jerbare 61-65, M 2 Responses Mar 2

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    You know what? I'm not gonna be embarrassed to

    admit this anymore. No, I don't do it in public. I've done it once and probably never will again, unless I'm with close friends making me feel comfortable. But at home, sometimes I like to dress as a guy - wig and all. Mostly for relaxation, fun and/or experimentation heh.
    imagine524 imagine524 18-21, F 6 Responses Dec 8, 2014

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    been doing it for years.

    usually 'borrowed' my mother's bras. on Monday i finally bought my first bra of my own and panties!
    bobjillcd609 bobjillcd609 22-25 3 Responses May 14

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    a week from now i'm using a dressing service to

    go out for a day en femme. i've asked for challenges, had some daft replies, but so far one good one, to try on a dress in a department store. i've never done that before. what other challenges , that don't involve using my voice or giving myself away, can anyone think of?
    donnaka donnaka 36-40 3 Responses Feb 16

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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 3 Responses Oct 19, 2012

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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 22-25, M 3 Responses Jun 18, 2014

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    I'm wearing my housemate's panties at work

    right now. it's my first time. I love it, feel so sexy
    illbc illbc 22-25 2 Responses Apr 27

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    Msg me some dares ill send pics

    as proof I did dare ;) ill. Do whatever you want except going into public en femme
    deleted deleted 26-30 1 Response Feb 20

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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 56-60, M 4 Responses Aug 14, 2014

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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, 2014

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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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    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 Sep 5, 2014

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    If you're into the TV show "Bones",

    there's an episode called "The Drama in the Queen". It's all about the murder of a drag queen and discusses how the wife feels. Good episode.
    shadowplt shadowplt 51-55, M May 26

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    Been getting more clothes

    for myself and slowly easing into a more feminine demeanor and I couldn't be happier! All I wish is that I had someone to go shopping with! Ugh I guess I can't have it all
    Rockitt Rockitt 18-21, M 1 Response Apr 28

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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 56-60, M Oct 28, 2013

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    I've never had the desire to dress en femme,

    but the look and feel of women's clothing (especially hosiery and heels) excites me. It's crazy to think that the only time I ever feel sexy is in women's clothing. I tried it when I was about 15 and I've been hooked ever since. I just been closeted.
    jkale324 jkale324 26-30, M 1 Response Feb 16

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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 56-60, M 1 Response Jun 6, 2013

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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, 2014

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    My wife informed me that she accepted an

    invitation to a Halloween party. I told her "Great!" I added that I'd like to go as a Southern Belle or in one of my square dance outfits. She didn't say "No." But she also didn't say "yes." I am hoping that lets me go to the party as a woman.
    SweetRhonda SweetRhonda 51-55, T 9 Responses Sep 25, 2014

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    I like to dress as a woman

    and feel feminine, I actually feel much more relaxed and 'me' when wearing a dress. I would love to chat with others who feel the same
    deleted deleted 26-30 3 Responses Dec 15, 2014

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    With Valentines day coming up

    now is a perfect time to shop for intimate apparel. As I have gotten older I find it becoming more difficult to be passable in public. I just got back from the mall shopping and bought a beautiful black baby doll nightgown and red Bustier. The Sales clerk was very helpful. I...
    Stephaniegirl226 Stephaniegirl226 36-40, M 7 Responses Feb 6

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    Anybody msg me and give me some kinky

    crossdressing dares will show proof of dare if requested ill do anythin ;)
    deleted deleted 26-30 1 Response Feb 19

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    I absolutely LOVE to Cross Dress

    and LOVE wearing nothing but dresses and skirts with blouses. Like every other cross dresser, I wish I could do it all the time. I find myself doing that a lot on my days off, and I am fortunate that my wife is accepting. She doesn't like to go out with me when I am en femme...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Oct 27, 2014

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    Last night my wife made a comment to me

    that made me feel real good. She asked me when I was going to shave. I thought she was talking about my face, but she was talking about my legs. She told me she liked the feel of my legs when they are shaven clean of all the hair. Now that summer is over and the shorts are put...
    SweetRhonda SweetRhonda 51-55, T 1 Response Oct 5, 2014

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    I have a thong,panties,

    tights,leggings,a black short dress,pink long dress,pink and black lingerie only for front upper body, pink top, black bra,pink thong msg me dareing me to wear any combo and ill send pic proof I did the dare ;)
    deleted deleted 26-30 1 Response Feb 19

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    any cute guys who are bi up to age 28 wanna

    talk about cross dressing? any who do it in their sisters or stepsisters lingerie?
    kinkyguy000 kinkyguy000 26-30, M 3 Responses Nov 28, 2014

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    Every crossdresser expresses their femininity

    in different ways, some are comfortable to stay in the closet, others are fortunate to be passable and go about their lives in their female persona. I have found that I can showcase my femininity through theme nights, whatever theme a party or function is ,I dress as the female...
    Cherridarling Cherridarling 56-60, M 4 Responses Feb 8

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    One small step nearer nirvana.

    I now have one of my girlfriends bras to wear - at least for now. The bra suffered from some black dye running into it and as a gesture of kindness I offered to see if I could get the dye out of it. I tried and got a lot of it out of the cups but the elastane sides are still...
    jane19502010 jane19502010 61-65, M 6 Responses Jan 3

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    Related Experiences

    Well, I'm here. Lonely. Ask your questions, pass your judgments. I think I'm ready for it.
    BrokenMelodies BrokenMelodies 22-25, M 2 Responses 3 hrs ago

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