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I Love Crossdressing

Personal Stories, Advice, and Support 4,104 People

    So today was a huge step

    for me. It started out very innocent. I was home alone and I dressed up. Then I put on some jeans but kept my thigh highs on and garter belt and nice lace thong. I then went to some sex shops and while I talked to people I played with the garter straps. it was so much fun...
    DillonSmith DillonSmith 36-40, M 2 Responses Aug 20, 2015

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    Learning Along The Way. How To Feel My Sexiest.

    Hmmm... I guess I'll begin by saying I've learned a few things that turn me on.Getting dressed up is fun but getting attention from men and women is the biggest thrill (sexually) of my life. I have continual fantasies about meeting men and/or other CD's for real and I don't just...
    BlackSkirt BlackSkirt 46-50, M 8 Responses Jun 28, 2012

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    My wife and I went shopping

    for nighties and panties last night. She is becoming more accepting each day. I have a renewed love for her, as she understands me and allows my Femme side to share our lives. It's taken over 30 years to get this far!!! Don't give up.
    parttimelisa parttimelisa 51-55, M 5 Responses Jul 4, 2015

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    Summer before college,

    obviously old enough to be alone in a department store.Yet I feel like that same preteen slipping into my first silky panties. Exhilarated yet the amount of anxiety was almost more tha I could handle. Oh such a gurlie feeling surrounded by panties, bras, slips, nylons of every...
    Cassiegurl Cassiegurl 36-40 3 Responses Oct 12, 2014

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    nygax nygax 18-21, T Jan 31, 2015

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    I always wear silk lingerie under my Male

    clothes but when I get home I slip into a knee length dress. Underneath my dress I wear silk French Knickers stockings and suspenders. I love wearing dresses.
    timothy1994 timothy1994 22-25, M 1 Response May 27, 2015

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    Crossdressing In Your Senior Years.

    I have found that as I get older my love for cross dressing grows stronger. I have been dressing for years, from a boy of 15, and have found as the years progress my urge to cross dress increases. Since retirement I am cross dressed every day, with my wife accepting this part...
    deleted deleted 26-30 4 Responses Jul 27, 2013

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    First Crossdressing And Sex With My Friend

    I've been crossdressing for several years but was too shy to dress with another CD. I finally met with my friend today and let another person see me in my outfits. I've enjoy posting my pics for this cyber CDing but couldn't get the courage to dress with someone else. I...
    robbi95 robbi95 46-50, M 5 Responses Jun 5, 2012

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    I love to crossdress

    so much. There is something about it that is just so indescribable. I believe what it is for me is the feeling of having a female's outfit or undergarments against my body gives me a intense feeling.
    12rak38 12rak38 36-40, M 2 Responses Jan 16

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    How I First Realised Who I Am

    hi im amy and i am a crossdresser. i first wore girls clothes when i was at a friends house and we decided to play dress up. i was about 11 or so my best mate and his sister decided to pretend we were at school. she was to be the teacher and me and my mate were to be the...
    xdsubamy xdsubamy 26-30, T 6 Responses May 9, 2013

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    Open Bottom Girdles

    I love wearing an open bottom girdle...it clutches my midriff so nicely, exposes by clitty and my butt to view, looks so 60's, straightens me out up & down, pushes my breasts up....and makes me think erotic thoughts. I have a pink one, a black, and a white one. I got all of...
    Nel1966 Nel1966 66-70, T 11 Responses Nov 30, 2012

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    So, I've been a casual reader of this site

    for years, now it's time to share a small bit of my experience. I am a 50 something married male with two amazing and successful children. The kids are out of the house and it is wonderful! I thought it was time to finally come out to my dear wife of 30 years and share my...
    parttimelisa parttimelisa 51-55, M 5 Responses Oct 18, 2014

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    Caught Crossdressing By Sister

    I have been secretly wearing my sister's clothes since my early teens, and have always had the thought of what a thrill it would be to get caught! Well a recent summer saw my parents go away for a couple of weeks on holiday. Me and my sister stayed at home, however she was dog...
    20nik 20nik 18-21, M 6 Responses May 1, 2012

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    Confusion Sets In

    I spent the night tossing and turning and wondering what I had done. I had just revealed my lifelong secret to my friend of many years. He is now fully aware the I am a bisexual cross dresser. To complicate matters further, I performed ******* on him. I'm not going to say I...
    Kristi2002 Kristi2002 41-45, M 9 Responses May 2, 2011

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    My wife has always told me

    that I have the tiniest and most unmanliest looking penis she has ever seen and that in fact it looks more feminine than masculine and she tells me that guys like me should wear lingerie and women's skirts etc, we always go out on a Friday night and under my jacket and jeans I...
    deleted deleted 26-30 Nov 27, 2015

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    I put this dress on after my wife left do work

    the other day. I had the day off. I did some laundry, paid some bills and some light cleaning. Then I had to get changed to go mow the lawn. Still had my ladies shorts on.
    mat2Robin43 mat2Robin43 51-55, M 8 Responses Aug 26, 2015

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    Good, But Not As Great As

    I've used ****** and plugs on several ocassions and those are just fine for those special solo times. But nothing in this world compares with the feeling of a guy behind you, or on top, sliding in and out. That first push as your opened up, that tiny hint of pain, just awakens...
    PaperDollCD PaperDollCD 51-55, T 10 Responses Aug 8, 2012

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    Not so much a story but need advice.

    Where can one find some sexy shoes without breaking the bank. I am a size 15 in ladys shoes and it is murder trying to find the bigger sizes that isnt priced at 100.00. Need to find some sexy 4 inch heels so the wife can critique and teach me that oh so sexy glide.
    new2thiscpl new2thiscpl 36-40, M 7 Responses Oct 24, 2014

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    Quite Possibly The Best Night Of My CD'Ing Life! Makeover!!!

    So If you've happened to read my previous stories you may know that I found a T-friendly shoppe in Massachusetts. I went there before and found some great things including shoes and breast forms. When I was there the clerk asked me if I'd be interested in a makeover. At the time...
    iheartdressing iheartdressing 26-30, M 8 Responses Jun 8, 2013

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    Must Read For Crossdressers

    Like many people on E P we long to be understood. We are not freaks and our hearts are always true. Like many Crossdressers I can't explain why I do this , but I can say, I have always loved it. I have a different personality when I am a girl. I am much sweeter and I...
    LisaMichaels LisaMichaels 41-45, M 14 Responses Nov 18, 2008

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    Lovely Night

    I had a long day today and couldnt wait till i got home.  First thing i did was run a hot  bath.  I soaked in the tub and sipped on a glass of wine while i let all my tension and maleness go.  I shaved my legs, slipped into a pair of heels...
    vanessacarr vanessacarr 36-40, T 15 Responses Jun 24, 2008

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    I got up early this morning

    and put on all fem clothes. Panties, bra, tights and a dress. A went to the store and picked up some donuts for everyone at work. I am now at a hotel down the street from my work setting in the lobby in my dress. I just love to be in a dress.
    mat2Robin43 mat2Robin43 51-55, M 4 Responses Dec 24, 2014

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    A Short Trip With My Wife.

    I had an opportunity to go away with my wife for a couple of days and be free to dress the way I wanted to. It was exhilarating ! My wife was so supportive of me the entire time. The first night we went to a casino, had a few drinks and did some gambling. We never really won...
    SissyErinn SissyErinn 41-45, M 20 Responses Nov 24, 2013

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    My ultimate dream is finally coming true.

    I am house sitting for this unbelaibeiblely hot girls family while they are on a two week vacation. I have fanatasized about cross dressing in her cloths for years and the time has come now that they have left. I can only imagine what a sexy young girl will have in store for me...
    Zoe24 Zoe24 22-25, M 4 Responses Jun 7, 2014

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    My First

    Im bisexual and my first time cross dressing was when i was 17 i put on a g string pantyhose lace bra tight cocktail dress and high heels luckily i wasnt walking long my bf tied me up and ****** me so hard
    Aaronxdress21x Aaronxdress21x 31-35, M 9 Responses Oct 24, 2012

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    I Love It !!

    I just love all the different things you can wear. It's really a turn on when i slip on a pair if panties, then a bra and everything else. I love going through draws and looking for boy shorts and thongs. I love the smell to ! It's just a joy getting dressed up and walking around...
    pantynhose pantynhose 18-21 6 Responses Apr 27, 2013

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    The Bra!

    The bra. I feel so femine when I put on a bra. I love to wear a bra.
    CindyLinda CindyLinda 56-60, M 14 Responses Nov 11, 2012

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    Could Never Give It Up

    Cross Dressing is something i could never give up. I feel so much more comfortable dressed in womens clothing than mens.  I started wearing panties every day about 3 years ago when my wife found out about my cross dressing, and i no longer own any mens underwear.  I also love...
    AmberRosecd AmberRosecd 36-40, T 5 Responses Apr 27, 2013

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    First experiences who can ever forget.

    The exhilaration and anxiety of that first time alone as a child slipping those silky sweet nylon material brief panties from the hamper. The feeling between my fingers the softness against my cheek.The immediate rise in my shorts that surprised me.These were mommys lovely...
    Cassiegurl Cassiegurl 36-40 8 Responses Oct 10, 2014

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    My wife and I went to a fabric store today

    where she bought some pink polyester-cotton for pajama pants, and some pretty ruffled cotton eyelet for the leg hems. I can' wait till they''re made and I can wear them!
    zetayoni zetayoni 70+, M 2 Responses Sep 21, 2015

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    Ive been dressing since i was 13 yrs.

    Old. I was the only male in a house of 7 women. Only one was younger than me and that was my little sister. I had 2 aunts 2 cousins my mom and my mom's friend. My mom her friend and my older aunt wore that sexy vintage lingerie. Girdles and slips and garter belts and stockings...
    Letshavefun70 Letshavefun70 41-45, M 2 Responses Oct 22, 2015

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    Today I needed to get my inner female out

    and needed to dress up bad! I slipped on my red bra, matching panties with padded bum and hips, sweater tights, 3" heeled shoes. I have a short blue bodycon dress with see through sleeves from Forever 21. I put on large silver hoop earrings and some necklaces. I then did my...
    jessicavamp jessicavamp 41-45, M 4 Responses Oct 19, 2015

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    Wish all ladies a great begining to.

    .. "Twenty Sixteen (2016)".... Feel Twenty & Look Sixteen....??
    kamyani kamyani 31-35 Dec 31, 2015

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    I Love To Dress Up

    I started crossdressing at a young age. It all began when my parents went out and my 3 older sisters would dress me up in their clothes, at first I hated it, as they would make fun of me, but the more they done it the more I liked it, I would always protest to them that I didn't...
    2wzh7i1t0h 2wzh7i1t0h 56-60, M 1 Response Dec 16, 2011

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    I am currently sitting at home fully dressed

    as a woman. I feel so relaxed ,comfortable, and Right this way. I am always amazed at how different i look and feel when i am a woman. I have on full makeup ,nail polish, and perfume. I am wearing panties ,bra, suntan pantyhose, a bodyshaper , and silicone breast enhancers...
    MichelleG444 MichelleG444 41-45, M 4 Responses Dec 3, 2014

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    Today after a long day at work I Came home had

    a shower and got dressed in my girly clothes. First I put on my satin pink panties, carefully pull on my black tights I then I got my favourite black top put it on I choose my favourite calf length satin floral skirt slipped it on. I'm now sitting here totally relaxed all...
    johnny1505 johnny1505 46-50, M 5 Responses Oct 13, 2015

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    Alex And Vanessa

    For the wife of crossdresser perhaps the most difficult thing is to understand that crossdresser feels when he was in the women's. I hear this question all the time from women, the partners of which is crossdresser, and I often asked this question.A few years ago I had a friend...
    Cassandra69 Cassandra69 22-25, T 11 Responses Jul 28, 2012

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    More details in the comments.

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    wannabepreggers wannabepreggers 36-40, M 1 Response Aug 22, 2015

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    Hello I am 26 year male.

    . I had a childhood desire to dress like girl... Since then it is now fulfilled .. Today first time I wore panty to my workplace.. I feel awesome and very satisfied ... Usually in night I dress like girl ...!! I just so love it. I am interested in women only.. I am not gay or...
    Samc7 Samc7 26-30, M 3 Responses Mar 7, 2015

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    Love It!

    i wear as little male's clothing as i can get by with anymore. i always wear at least panties and camisole. Lately i've been wearing Female shorts, cami, socks, shoes, bracelet, dangly ear rings, lipstick, eyeliner and mascara. i love knowing i don't have any men's clothing on me...
    sissyslavejamie sissyslavejamie 51-55, T 14 Responses Jun 17, 2008

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    I love when I get the chance to dress up in a

    beautiful dress and feel pretty. I don't do it very often but it makes me happy when I do. I am a man that likes girly things.
    deleted deleted 26-30 2 Responses Jan 24

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    I'm home alone and going to put on bra panties

    and pantyhose. high heels and a dress.
    deleted deleted 26-30 Jul 15, 2015

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    Traveling for business this week.

    Great opportunity to dress and shopfor cclothes. Wore my black heels into Lane Bryant. Tried on a few things. Found a pair of black leggings and brown riding boots. Red top as well. Paid for them decided to ask if I could change into my new outfit as I walked out. Sales...
    cdjo cdjo 41-45, M 9 Responses Jan 28, 2015

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    Thank u gurls for all your responses.

    My wish is that we could all be together in a house for a day filled with vintage lovely silky panties lingerie makeup perfumes lotions sissy pink and pastel bedrooms . A weekend bed and breakfast staffed by sexy transgenders in maid and schoolgurl outfits with one mother in all...
    Cassiegurl Cassiegurl 36-40 1 Response Sep 18, 2015

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