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I Love Wearing Sissy Dresses

Anyone else like to dress in pretty sissy dresses? 711 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    I have been wearing exclusively panties now for 2 weeks. It feels so amazing. So liberating. I am going shopping tomorrow with my girlfriend to VS to pick out a few more items to...
    Winesissy Winesissy 46-50, M 9 Responses Jul 10

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    I can't decide if I should wear my baby blue, silky cheeks or pink silky bikinis tonight!!! Can anyone help a gurl out???
    Winesissy Winesissy 46-50, M 7 Responses 5 days ago

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    So guys and girls I am needing some help.I am wanting to pic has my first pair of thongs.Any suggestions on brand,fabric,any bigger size,etc.I love wearing panties and I think...
    Bigboylovinpanties Bigboylovinpanties 18-21, M 1 Response 19 hrs ago

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    I love wearing dresses, but changing into sweat pants and a hoodie is so much more comfortable! 😍
    TheSongPlaysWithin TheSongPlaysWithin 16-17, F 2 Responses Jun 25

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    I have recently "come out" so to speak in my love of leggings. I have always loved them, but since the social stigma of men wearing them has been / is so negative, for some reason...
    bigsalams bigsalams 36-40, M Jun 23

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    I love wearing crop tops they're so comfortable and i love wearing them when it's hot outside :3
    jaynick15 jaynick15 13-15, F Jun 23

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    I have loved wearing women's shoes and boots since I was a child. I wear them in public now after only wearing them indoors for years.
    hh4evry1 hh4evry1 36-40, M 6 Responses Jul 14

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    I just love wearing underwear which makes me feel desirable and sexy
    ashdavenport ashdavenport 18-21, F 11 Responses Jun 26

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    I love wearing them! They look and feel good :)
    JennyRose2 JennyRose2 13-15, F 3 Responses Jul 12

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    i love wearing pink leather ballet slippers and ballerina outfits i cant help it it turns me on lol
    deleted deleted 26-30 1 Response 6 days ago

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    i love wearing pink ballet tights with a pink silk leotard or pink silk ballet dress
    deleted deleted 26-30 1 Response 6 days ago

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    i love wearing anything related to ballet as long as its pinklooking for friends that share the same
    deleted deleted 26-30 6 days ago

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    I love wearing thongs so boys will see my thong and I wear my thong with a pair of low rise jeans and I like my but crack and thong is showing
    lauran2014 lauran2014 16-17, F 1 Response 2 days ago

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    Almost all of my female attire is second hand! I go to Garage sales a great deal. I have purchased; second hand panties, bras, slips, pantyhose, skirts, blouses dresses, and...
    OhioSissy OhioSissy 51-55, M 4 hrs ago

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    It was great when I was 12, 13 & 14 and I could get away with wearing a girls two- pice skimpy bikini, since my lack of full boobs wasn't such a giveaway at that age. I loved...
    LuvToWear LuvToWear 22-25 1 Response 9 hrs ago

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    Our religion (we are a Christian denomination that requires women to wear skirts and dresses, never pants) believes that pants are for men and skirts and dresses are for women. Our...
    IAmLovingLife1234 IAmLovingLife1234 41-45 3 Responses Jun 23

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     Look at this picture. I'm not afraid to show skin. I'm the one wearing the crop top if that wasn't obvious.
    teenally teenally 13-15, F 1 Response 11 hrs ago

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    Female underwear,bras,camisoles,bby dolls ,dresses,shorts, lipstick nylons and pantyhose. My fave route is heels. All a part of me
    sexipants sexipants 41-45 11 Responses Jun 23

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    I love so much dressing up wig makeup and Sexy underwear and high heals, Most the time that they way I spend my time at home, I love dresses but only to go out......
    amber8642 amber8642 51-55 1 Response Jun 29

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    Cleaning Out the Closet I have been cross dressing for many many years and have acquired a collection big enough to fill a walk in closet. Some of the items I have date all the way...
    jamie50 jamie50 51-55 5 Responses Jul 3

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    I also so would LOVE to buy this and can't pick it up at the store, I LOVE it it is sooooooooooo sexy!!!
    wtbwoman wtbwoman 41-45 3 Responses 2 hrs ago

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    i get these crazy feminine urges all the time and the only way to satisfy them is to dress in female lingerie. Now, I am still a guy and, like most guys, am generally lazy and I...
    DonnaSue10 DonnaSue10 66-70, M 8 Responses 12 hrs ago

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    I spent a second day wearing a skirt on my travels through France. Stopped at lots of service stations for petrol food and coffee. I got quite a long state from a older lady. It...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses Jun 23

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