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I Enjoy Crossdressing

Personal Stories, Advice, and Support 1,033 People

    My Wife Finally Knows - I've been crossdressing since I was about 10 years old. At the time I loved to put on some of my mother's stockings and sometimes my younger sister's...
    BettyLouAnne BettyLouAnne 46-50 1 Response Oct 31, 2012

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    Crossdressing For Life - Well, almost. Since age of seven I have been dressing in women's clothes. First my mom and sister's. Then Aunt caught me in her panties. She helped me...
    fatsissypauline fatsissypauline 61-65 2 Responses Sep 26, 2013

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    Often Misunderstood... - EP has given me the opportnity the last few months to find out more about myself. In particular why I am how I am, why I like what I like, and if I am...
    garterbeltgirl19 garterbeltgirl19 36-40, M Sep 22, 2011

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    My Story - I started fully cross dressing at the age of 23 after wearing pantyhose off & on since the age of about 14/15 but at first I could only do it in the confines of my...
    xdpaul xdpaul 56-60, M Jun 8, 2011

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    i had a wonderful weekend. It started friday. got to paint my fingernails.(toes always done) and off my mistress and I went. I was able to go through her closet and pick out three...
    jamie123T jamie123T 46-50, M 1 Response Jan 13

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    Love Crossdressing - nothing better dressing up in 6inch heels thigh high silk stockings miniskirt, with a thong **** tucked away looking for ****. they bend me over while in...
    goforit514 goforit514 46-50, M 1 Response Jun 25, 2012

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    I Enjoy Crossdressing - i started crossdressing back in 1998 it started when i accidently bought a womans tank top from a thrift store i wasn't sure at first why it felt the way it...
    kaitlinrenee24 kaitlinrenee24 41-45, T 9 Responses Jul 28, 2012

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    Neighbor Caught Me Crossdressing! Had Foursome With Her And Her Husband! - had a little mishap, that may turn into something fun. :)so, when at home, i am 95% of the time dressed...
    jenrip jenrip 26-30, T 5 Responses Apr 4, 2013

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    More Than Enjoy! - I don't know how to describe it. Yes, I enjoy it but it is so much more. It just seems so RIGHT. If I didn't enjoy it, I wouldn't do it. I would spend my...
    robyn2801 robyn2801 56-60, T 2 Responses Jul 26, 2013

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    The Experience - I have been cross dressing for over 40 years now. That is to say , I have been wearing what is usually designated women's clothing for that time. I started with...
    miranda69 miranda69 46-50 1 Response May 24, 2013

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    I Feel Much Better When I Have Lingerie To Wear. - Throughout my high school days I dressed whenever I got the chance, in a house of 10 people and 1 bathroom not much. But i did...
    cosmadee cosmadee 56-60 1 Response Mar 28, 2013

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    Why I Enjoy Dressing In Lingerie - I want to do it because I enjoy it so much. I can’t express the feelings and sensations I get while dressed in words. Dressing in silky...
    jamiesissycd jamiesissycd 61-65, M 2 Responses Dec 20, 2011

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    Of Course - I just love to wear my lingerie. I wear panties 24/7 (except for Dr. appointments). On weekends I will sometimes wear my thigh high stockings under my jeans.I don't...
    happilymarriedguy happilymarriedguy 51-55, M 1 Response Apr 4, 2013

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    I enjoy crossdressing - Check out my pics,please leave comments(: maybe we can talk, share stories and trade pics? (:
    blazin0cd blazin0cd 18-21 4 Responses Dec 3, 2013

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    Cross-dressing Like A Girl - I like to dress like a girl. I have a fantasy to dress like a girl in sexy costume and want to seduce a nice hunk man and want to have sex with him
    rajeevpathak100 rajeevpathak100 31-35, M 1 Response May 30, 2012

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    I Love Crossdressing - Crossdressing is everything to me! Because I feel I was supposed to be born a girl and not a guy so I wear girls clothes, right now I'm wearing a khaki...
    pantylover95 pantylover95 18-21, M 1 Response Nov 16, 2013

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    My Dream Outfit - my dream outfit would be a nice pink bra and a matching thong, id then have some black high heels on with some knee high socks! then over my beautiful thong id...
    stranger123456 stranger123456 18-21 3 Responses Aug 11, 2013

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    My beautiful wife and Mistress have decided to start our pages on here looking for friends and networking. I am 40 bi m who loves to be humiliated and made to dress up by my wife...
    hersissycuck hersissycuck 41-45, M Dec 9, 2013

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    Im starting crossdressing any old dress skirt wigs shoes will b a big help i can pay for post if u wish
    crossdresskatie crossdresskatie 22-25, M Dec 8, 2013

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    Unconsciously Crossdressing! - I have purchasing women's jeans and blouses from a local Good Will with my wife, it seemed like the cool thing to do since I typically do not...
    43454345an 43454345an 56-60, M 1 Response Mar 14, 2013

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    We Enjoy Crossdressing - I've been into crossdressing since I was younger. I love wearing stockings and suspenders and satin panties. I've been bi since I was young, but I love...
    pantiescouple pantiescouple 26-30 1 Response Jul 19, 2010

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    First Time I Wore Womans Clothes - I have been fascinated with feminine clothing from my earliest memory. They were so mysteriously constructed. Their but the buttons were on the...
    cosmadee cosmadee 56-60 2 Responses Jan 15, 2013

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    The Beginning And Scared - Hello i am a 20 year old guy and I love to Crossdress. It started when my mom past away and I was 9 years old that was when I started I was home alone...
    crossdressboy10 crossdressboy10 18-21, T 1 Response Mar 19, 2013

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    Total Fail - So today I thought I was being really cute and sweet not to mention sexy when I went shopping for my boyfriend. I found these really cute thigh high red stiletto pumps...
    Ladysound Ladysound 22-25, F 2 Responses Jan 2, 2013

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    Webcam Crossdressing - When I'm home alone i go into my mums closet and put on her C cup bra and fill it up with tissue. I then go into my sisters room and put on a tight thong and...
    matty7326 matty7326 13-15, M Aug 27, 2013

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    I love wearing high heel leather boots, shoes, long leather gloves, corsets and leggings!
    LondonGuy1 LondonGuy1 26-30, M 3 Responses Dec 3, 2013

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    Finding Myself.... - when I was alot younger, like in early middle school years I started changing inside. Like most boys I was hitting puberty, curiosity and all that jazz. Now I...
    LuCyFuRs LuCyFuRs 26-30, M Oct 14, 2013

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    I Enjoy Crossdressing - I so enjoy cross dressing. I enjoy it  so much that i look forward to everyday.  I like to decide what to wear each day and then decide what I can change...
    jml2000 jml2000 56-60, M 1 Response Oct 29, 2012

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    And Now I'm A Mature Cd Servant , And I Have Never Been Happier! - i grew up in the south with a military dad, and a mom who worked for the govt. i can remember touching my moms...
    zanderb zanderb 41-45, T 2 Responses May 28, 2012

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    hello, my last story was over a yr ago. Now i'm living in charlotte with my girlfriend/mistress. She is all about dressing and exploring everything. We even have talked about go to...
    jamie123T jamie123T 46-50, M 4 Responses Jan 3

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    Dressing For A Wedding - So this past weekend we had to attend a wedding, I jumped in the shower and shaved what I am allowed to share. ( I feel like a child, shave what I'm...
    mpenner mpenner 51-55 3 Responses Sep 9, 2012

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    Where To Begin... - I am not sure when I first became aware of my desire to wear feminine clothing...but I know now that the beginning is not the focus...It is where do I want to...
    jyd1 jyd1 51-55, M 2 Responses Aug 19, 2010

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    The Advantages Of Having A Crossdressing Boyfriend Or Husband! - YOU have a live in cosmetologist. If he wears a skirt it's easy access. He always envies you because he would...
    jamiesissycd jamiesissycd 61-65, M 1 Response Feb 27, 2012

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    Love To Shave My Legs - I love the way thigh high fish net stocking feel over my shaved body. My legs are long and slim and I 1st started wearing the female clothing of a friend...
    NewTGurl NewTGurl 41-45, T 2 Responses Oct 29, 2011

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    CD And Sex Drive - I am a closet CD. Over the last year, my CDing has been increasing in intensity. I started off underdressing, trying my best to hide every trace of CDing. Now, I...
    ClosetTrans ClosetTrans 26-30, T Oct 2, 2013

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    The I Wear Panties Hat - I once hatched the idea of having a custom hat made at an embroidery shop "Embroider_me". My thought was to work on the design with a lady from the shop...
    mattr4u2 mattr4u2 56-60, M Jul 28, 2013

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    Letting That Femme Side Out! - Crossdressing is such a wonderful way to let out your emotions in a positive and healthy way. I live in a society where men are taught to be macho...
    Camifemme Camifemme 31-35, T 4 Responses Jul 22, 2012

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    Wow - Francine what can i say ok WOW you are a sweety hugs  Nadia
    deleted deleted 26-30 1 Response Jun 20, 2008

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    How It Started - i enjoy crossdressing as it makes me feel sexy all over.. as i have a strong love for lingerie.. and then it started when i was younger and would go over to...
    CathyCD CathyCD 26-30 2 Responses Jun 28, 2008

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    Crossdressing - Crossdressing i have crossdressed off and on since 1998 it all started when i got rid of some clothes after a garage sale for my mom also that same summer i bought...
    deleted deleted 26-30 Jul 22, 2013

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    Buying Lingere As A Man - I actually went to a local sex shop yesterday and bought two pair of sexy stockings. Also had mentioned to the girl behind the counter that I am into...
    swallowbig swallowbig 31-35, T 1 Response Mar 10, 2013

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    Shopping Cross Dressed! - What a great experience! I have been playing around with dressing for a while, but I've only gone out in public once before- and I was not confident then...
    stevekone stevekone 51-55 1 Response May 6, 2013

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    Crossdressing With Husband - AS I SAID I LOVE CROSSDRESSING , I MAKE MY HUSBAND WEAR SAREE AND ALL MY DRESSES EVERY NIGHT. WHEN WE STARTED THIS PROCESS I USE TO HELP HIM IN...
    sanjeetaklk sanjeetaklk 26-30, F 3 Responses Sep 27, 2012

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    She Let Her Friends **** Me - While I was in her lingerie she brought her friends in the room, and one by one they used their strap ons on my little sissy *** as I could only lay...
    curiouslycurious17 curiouslycurious17 22-25, M 1 Response Oct 24, 2013

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    I Find Panties, Pantyhose, And Stockings Orgasmic - i first started wearing panties at 13, and i havent stopped. just the sight of a hard **** in panties or hose is enough to make...
    jenrip jenrip 26-30, T 3 Responses Apr 4, 2013

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    That'S When I'M Me - I enjoy crossdressing because when I do that is the true me. I have always felt that I was a girl. Now dressing like one give me the feeling of completeness...
    Adam59 Adam59 56-60, M 2 Responses Mar 30, 2013

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    Creature Comforts - I just enjoy being in anything that a woman wears. The clothing is nice and soft and fits nicely. I have never shared my secret with anyone in my physical...
    deleted deleted 26-30 Aug 24, 2013

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    Related Experiences

    I do enjoy listening to myself. So yeh. I enjoy funny people :P
    pappa94 pappa94 18-21, M 7 hrs ago

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    I can't remember the first time I did get caught coz I think I was around 6 or 7 and it was just dismissed by people as I didn't understand what I was really doing. But earliest...
    apwnn apwnn 16-17, M 2 Responses Mar 17

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    My first crossdressing experience was with my Mum's knickers. I remember I wanted to recreate a scene from a film where I saw a beautiful woman walking around in just her underwear...
    LucyTG LucyTG 26-30, T 4 Responses Mar 19

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    It really is a fantastic feeling slipping in to a nice skirt or dress and complimenting it with other nice items :) I love wearing dresses and the feeling of how free everything...
    LucyTG LucyTG 26-30, T 4 Responses Mar 20

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30