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I Love Wearing Sissy Dresses

Anyone else like to dress in pretty sissy dresses? 729 People

    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

    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
    5 Responses Jan 17, 2010

    I only wish I had the money

    and room to buy some of the gorgeous sissy dresses that are on eBay and other add sites. My dream would be to have a sissy room where I can keep all my dresses for play.
    jasminemaine jasminemaine
    2 Responses Nov 26, 2015

    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


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

    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
    1 Response Jul 20, 2010

    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
    8 Responses Oct 25, 2009

    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
    3 Responses May 31, 2013

    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
    66-70, M
    Mar 5, 2010

    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
    61-65, M
    15 Responses Aug 19, 2009

    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
    4 Responses Apr 1, 2012

    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
    11 Responses Jan 16, 2010

    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
    2 Responses Nov 18, 2009

    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

    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
    56-60, M
    4 Responses Dec 3, 2010

    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

    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
    2 Responses Nov 21, 2013

    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
    3 Responses Jan 17, 2010

    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
    Jan 22, 2010

    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 alexandra166
    1 Response Nov 8, 2010
    timothy1994 timothy1994
    22-25, M
    2 Responses Aug 29, 2015

    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
    6 Responses May 4, 2010

    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

    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

    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
    1 Response Mar 4, 2010

    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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