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I Love Wearing Sissy Dresses

Anyone else like to dress in pretty sissy dresses? 715 People

    Sissy Dresses

    i love wearing sissy dresses being a sissybitch its a turn on and indicates my sissy status! My Mistress likes to take me out in public in a sissy dress its such a turn on and so sexy but so humiliating too soo very good!it so good to be dressed the way you want to be able to...
    mandiejune mandiejune 51-55, M Jun 5, 2010

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    Virgin Sissy Let Loose On The World!!!

    In the past month I have decided to live my fantasy rather than just dream about it. I have decided that life is just to short to sit and wonder what if. I am now the proud owner of four beautiful sissy dresses and accessories. I am having a fab time playing dress up, i just need...
    siswendy siswendy 46-50, M 2 Responses Jul 4, 2010

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    Made Into A Sissy

    In my teens i got caught spying on my friends sister and her friends at a sleepover. Her mom as punishment gave me a perm as she was a hairdresser. Thinking that was the end of it she told me they needed a ballet dancer in her daughters dance class. I was embrassed but had to go...
    userwn8543 userwn8543 46-50 3 Responses Apr 1, 2012

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    Love To Wear A Sissy Dress

    hi all i am looking to buy a sissy dress. But i don't know where to buy one if some one can help me. I live in Alberta Canada me email is alexandra166@hotmail.com
    alexandra166 alexandra166 41-45 2 Responses Nov 8, 2010

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    I Like to Dress Like a Girl

    I enjoy wearing sissy clothes. I have Since I was 10 or 11 years old. They make me feel more pretty. When I was young I could get away with being a girl, but now that I am older I look like a guy in a dress. I still like to dress like a young woman. It makes me feel like a sissy...
    sisypwimp sisypwimp 41-45, M 5 Responses Oct 4, 2009

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    I Soooo Love Warring Sissy Dresses

    Im most comfortable in a pretty dress.  The sissier the better and I love pretty shoes to match.   Kisses Denise
    deleted deleted 26-30 3 Responses Nov 18, 2009

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    Sissy Maid

    I enjoy wearing my maids uniforms and have a friend who becams my master and buts into my sissy dresses or one of my uniforms and keeps me in each room to clean. I am also there to show off my sissy dresses.
    sarahtmaid sarahtmaid 51-55, M Sep 5, 2011

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    Caught And Petticoated

    I was alone for the first time in awhile  my wife had gone shopping hich usually means hours.  Just as I had finished Pulling the pink cashmere sweater over my head   I heard the click of the camera.   I spun around and click again,  I had...
    SissyLisaMiddleton SissyLisaMiddleton 61-65, M 13 Responses Jan 16, 2010

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    Little Girl Sissy Dresses

    I love to wear pretty dresses. As an adult little girl, any dress with Peter Pan style collar, short puff sleeves and a very full skirt with a petticoat will melt my heart! I have so many pretty dresses to choose from but pink satin party dresses are my favourite! Pink is such a...
    sissylittlegirlkatie sissylittlegirlkatie 26-30 1 Response Nov 21, 2013

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    Bending Over In Front Of Mirror

    I have been crossdressing since a young age. I got married, I told her before we were married and she loved the idea of seeing me in panties and lingerie. She recently bought me a tight skirt and I walked around the house and bent over in front of the mirror to see the tight...
    pantiescouple pantiescouple 26-30 1 Response Jul 20, 2010

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    Mature Sissy

    Am a "mature" sissy and so love my pretty pink satin sissy dress's,mmm oh feel so good. I dress as the sissy i am every chance I get.Course as a sissy I do love to please,every sissy should. darling
    Darlinggurl Darlinggurl 70+, M 5 Responses Oct 15, 2011

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    A Pretty Sissy Girl

    I've been dressing for ages now and love the sissy little girl look so much with all the pretty silky frilly things they get to wear. Nothing is more fem then frilly sissy panties, nylons with pretty ankle socks in my pink Mary Jane shoes. Then a full petticoat, a satin sissy...
    frillysissy frillysissy 56-60, M 16 Responses Jul 23, 2011

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    Expect The Unexpected

    I am a 19 year old boy going to college, living in an aparment near campus. This semester i took a class that was taugh by 2 young beautiful hot girls with decent boob, awesome ab, and dress very sexy, their name is Abi and Jennifer. They are so close to each other i dont know...
    a009 a009 18-21, M Mar 5, 2010

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    Sissy Baby Wedding

    I remember the first time I got to war a sissy dress in public. We went to a sissy AB wedding at a Holiday Inn and I was asked to be best man, well maybe I should say the Maid of Honor. The groom was a sissy baby and was in his prettiest sissy dress, so I was to wear mine. It...
    babybearjean babybearjean 56-60, M 16 Responses Aug 19, 2009

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    So...

    where do you all get your sissy dresses from? I get mine from birchplaceshop.com but i'm always looking for alternatives :)
    sissyamelia sissyamelia 18-21, M Jul 21, 2011

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    i have a sissy little girl trapped inside

    Im a man split in two.  On the outside im the "normal" (as society would have me) man, but inside there is a sissy little girl tryng to get out.   Unfortunately ive never managed to find a way to actually get chance to dress as I want so it stays a...
    SissyGirlJessica SissyGirlJessica 41-45, T 4 Responses Nov 11, 2009

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    Sissy Dresser

    Hi, I love to wear sissy dresses. I have a maids dress & a satin party dress. (Plus lots of other dresses too). I love to wear sissy panties, suspender belt & stockings with my sissy dresses.
    zymack zymack 56-60, M Mar 5, 2010

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    Fantasy Wear

    I love playing dressup lol! I have 4 french maids outfits, 2 princess outfits a goldilocks outfit and a snowhite dress. I just love the really sissy fairytale looking dresses, wear panties all the time (all pink) trying to save up for the dress in my profile pic, i think...
    tonto1 tonto1 26-30, M 3 Responses Mar 4, 2010

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    One Of My Turn-ons

    Ohhhh yes, wearing a sissy dress will definately make me feel like the fem sissy that I love to be!  My favorites are the very short mini dresses that show off my panties when I bend over or sit down.  I usually wear crotchless panties with them so that more shows that...
    SissyGena SissyGena 31-35, T 1 Response Jan 22, 2010

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    Dressing Pretty

    I have been collecting dresses from various sources for more than ten years!  I find myself favoring little-girl styles, and love to wear petticoats, tights and patent mary janes with the dresses.
    kiersten kiersten 41-45, M 1 Response Apr 29, 2010

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    Being A Sissy Littel Gilry Girl

    Yes me to i would love nothing better then to dress in cute pretty little girly gilr cloths all of the time i love the very thought of being a little gilry girl in feminine cloths 
    eleventhdr eleventhdr 51-55, M 9 Responses Oct 25, 2009

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    Ryoko From Catgirl Florida

    Hello; Yes, I have lived my life as a boy but I am really a girl.  Sorry for all you to heae this, but, it is true that boys want to be girls.  Yes. Too bad for all you homophobes out there. Get over it.  I  am a boy but I FEEL female. There you have it. I...
    Ryoko123 Ryoko123 46-50, M 6 Responses Oct 27, 2009

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    How I Became My Grandmother;s Special Granddaughter

    My grandmother helped, and guided me into the world of femininity, that  I will never forget and will always be grateful to her for seeing the pretty girl that was insde me. She passed away many years ago, but is always with me,. She discovered my girlish desires...
    missprettypinktoes missprettypinktoes 61-65, M 4 Responses Jan 17, 2010

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    My First Sissy Dress

    I finally got my own cute frilly sissy dress. I ordered it from the sissy store online. I got the pink baby bows dress with full pink petticoats and the super high-heel pink serving shoes. I am wearing my new sissy dress right now! I feel so cute and girlie and feminine in this...
    bethanngirl bethanngirl 56-60, M 7 Responses May 31, 2013

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    How I Became My Grandmother;s Special Granddaughter

    My grandmother helped, and guided me into the world of femininity, that  I will never forget and will always be grateful to her for seeing the pretty girl that was insde me. She passed away many years ago, but is always with me,. She discovered my girlish desires...
    missprettypinktoes missprettypinktoes 61-65, M 6 Responses Jan 17, 2010

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    I Vote For ...

    Those wonderful satin 'sissy' dresses are for all of those virgins (or born-again virgins) who love the swish and thrill of satin dresses.     As well as one like these:   A question of personal style and expression maybe. Also considered passe or...
    Josie06 Josie06 56-60, F 7 Responses May 4, 2010

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    I Am A Real Sissy!

         From the first time that I tried my sister's clothing on, I was hooked!  This was back in the 60's.  The panties were 100% nylon.  She had a baby pink play dress, that I wore more than she did!
    OhioSissy OhioSissy 51-55, M 4 Responses Dec 3, 2010

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    Related Experiences

    I love wearing sissy lingerie and my wife buys my lingerie
    rimonty59 rimonty59 51-55, M 6 Responses Aug 30

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    Yes, It happened again. Yesterday night, the temperature was good and I proceeded to go roller skating wearing nothing else than one of my skating dresses. I choosed my very small...
    Nadia1977 Nadia1977 36-40, M Aug 24

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    Yesterday my Mistress allowed me to wear these super cute panties 😊👙💕🎀
    narttu narttu 41-45, M 12 Responses Aug 27

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    Yes im a boy but i look like a girl and love wearing the girlyest dresses
    tomgirl7499 tomgirl7499 18-21, T 3 Responses Sep 3

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    I love wearing anything nylon and feminine. The more feminine, the better! I love to wear lace trimmed nylon panties, slips, baby doll nighties and nightgowns. I also love to wear...
    closetedcd60 closetedcd60 56-60, M 4 Responses 3 days ago

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    i love wearing wigs to change up my look so many woman make fun of me but they wear weaves.... i dont see whats wrong with wearing wigs every now and then lol is it wrong that i...
    momoayami momoayami 18-21, F Aug 22

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    I recently purchased the skirt you can see in the picture which I am wearing which is a body contouring style made of soft polyester a wonderful multi purpose fabric. When I put...
    FontanaSlips FontanaSlips 41-45, M 2 Responses 6 days ago

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    hello i love wearing boilersuits, im a plumber and stand out wearing them, but like to have my work close clean under them for going to shop for lunch, etc ,
    coyle88 coyle88 22-25, M Aug 31

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    I love wearing shorts with a hoodie and vans but I don't like wearing a shirt under the hoodie. The most perfect outfit I like to wear ^~^ it's comfy
    ShantaleeCx ShantaleeCx 13-15, F 3 Responses a week ago

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    I love wearing low-rise jeans or shorts with a low cut tank top that show off my belly and cleavage ;-)
    SexyBellyButton80 SexyBellyButton80 31-35, F 12 Responses Aug 17

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    I love wearing my nice silver shiny high heels. I'm 4'10" n my shoe size is 5. I look so chic in them. They almost look like the Disco shoe from the 1970s. Disco Rules!
    DiscoNight1970s DiscoNight1970s 46-50, F 8 Responses Sep 4

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    I have just started writing a new blog chronicling the slow feminization and sissification of my partner by myself. This blog is not a work of fiction, nor is it in any way the...
    deleted deleted 26-30 4 Responses Sep 5

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    Today I dressed up femininely in the dress you can see in the picture and it gave me a beautiful feeling of femininity and sensuality. The dress is a body contouring style made of...
    FontanaSlips FontanaSlips 41-45, M 1 Response 6 days ago

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    Hi, I am a pantyhose and tights wearing biker and attending lost of biker rally's and jol's,, I love to wear pantyhose and tights, so i will wear pantyhose under my normal riding...
    hosebiker hosebiker 51-55, M 1 Response Aug 22

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses Aug 21

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    I love myself wearing men clothes! For example borrowing (or stealing lmao) a t-shirt or a hoodie and wearing it <3
    dropdeadwilma dropdeadwilma 16-17, F 10 Responses Aug 29

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    hehehe you wouldn't believe this...but look down at the story I wrote on August 14th. I'm still wearing those clothes!!!! Still! That is 23 days without changing clothes! It is...
    TotTotTotTot TotTotTotTot 18-21, F 2 Responses Sep 6

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    I not only love to wear pantyhose, i love showing it, too. a lot! So, if anybody is interested or likes to see men wearing pantyhose (my pictures come with my face, too. not just...
    Herzey Herzey 46-50, M 1 Response 6 days ago

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    any ladies/girls wearing tight sexy leggings today? what type and colour?
    wheels1972 wheels1972 41-45, M Aug 16

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    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F Aug 20

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    I have to wear satin panties under my clothes and at home my wife has me take off my pants and teases me through them and she tells her friends and I do all the kinky things asked...
    CCstnt45 CCstnt45 46-50, M 9 Responses Aug 23

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    I just saw a girl wearing short shorts and admired how she could fit an iPhone in the front pocket without having it fall out. Interesting!! From AEO of course! Tan color. Inspired...
    TransAsian TransAsian 26-30, T 1 Response Aug 23

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    Ordered a few pair of "training bras" to get more used to wearing them daily. Hopefully they'll be here soon :)
    artsyguy86 artsyguy86 26-30, M 1 Response Aug 24

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