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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 587 People

    The Last Time I Crossdressed.

    Before I moved house, I purged my wardrobe, and gave a lot of my clothes to a local Charity. I thought that I had gotten it out of my system, leaving only a jacket and a pair of black slacks. I hadn't and I haven't. I have just ordered a black dress and am waiting for it to...
    leprechaunz leprechaunz 56-60, M 2 Responses Nov 5, 2012

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    Little Black Business Suit

    It was last night (8/4/13) and I put on a black business suit. I wore sheer to waist black pantyhose with a sandal toe, no panties, a white corset style cami with foundation bra built in, a semi-sheer white blouse, a form fitting pencil skirt and matching jacket. I also wore...
    BizSuitStacy BizSuitStacy 46-50, T 3 Responses Aug 5, 2013

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    Good Morning

    Feeling amazing this morning. Wearing my white thong, off black pantyhose, my blue tye dye maxis dress, black ballet slippers, Mabelline make me pink lipstick,and my toe nails polished red. Its only the 3rd time I have ever wore a dress so still a little nervous but happy too.
    JeanW1 JeanW1 56-60, M Sep 28, 2013

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    Tonight I am slightly underdressed ;) I'm just

    wearing a small black t shirt with purple brief knickers and matching bra. Feel amazing just walking around the house :)
    LucyTG LucyTG 26-30, T 2 Responses Mar 10

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    Tonight (Feminus Interruptus)

    So I had just finished dressing up: black bikini panties with lace trim, black bra with a dark purple racerback tank over it, black cable-knit stockings, short jean shorts and my fave purple tee with black sequins on the front that read 'Broken Heart' (and my fluffy fuzzy black...
    AliciaHalfcat AliciaHalfcat 36-40 1 Response Sep 22, 2013

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    I wore to bed last night,

    my tiny pj short shorts, white sting top, hoodie, hair loose, red bra with a big white bow, red cotton thong with red lace over the v part.
    shylilpaige shylilpaige 18-21, T 1 Response Mar 23

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    First time caught - I was wearing my leopard

    print leggings, flats shoes, ankle bracelet, purple lace leopard thong, white cotton bra with purple lace trim and bow, brown string top, with a shirt over it, long blonde hair, covered in make up, ears, rings, chain, bracelets and sun glass cause the sun was beaming (25degrees...
    shylilpaige shylilpaige 18-21, T 2 Responses Mar 23

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    I wore my navy blue schoolgirl minidress,

    white kneesocks and my shiny black MJ's.
    schoolgyrlKaren schoolgyrlKaren 41-45 6 Responses Apr 8

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    Right Now

    I feel wonderful! Finialy home from work. I am wearing my bubblegum pink padded pushup bra, matching nylon panties, my lite blue slacks, white tee shirt, my mabelline make me pink lipstick.
    JeanW1 JeanW1 56-60, M 3 Responses Sep 25, 2013

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    And Today

    omg nervous as hell but excited too. wearing my red padded pushup bra with lace trimed cups (38B) matching red panties, black pantyhose, black skirt, maroon tee shirt, black ballet slippers, red toe nails and red fake finger nails ( nervous she never seen me with nails) red...
    JeanW1 JeanW1 56-60, M Sep 29, 2013

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    Last Time Out

    last time out I wore A button front jeans mini skirt with a camisole and a black lace top over that. Black fishnet leggings and 3" high heel black boots. A shore black wig, b cup pads, thong panties, black danglely earrings, and false eyelashes with make up. Right now that is the...
    Brandie1960 Brandie1960 41-45, M 3 Responses Jul 23, 2013

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    Today 12/7/2013

    Its really warm today so im wearing a white halter neck top, teen girls knickers [panties] and pink skimpy hotpants its warm for tights, with a pair or open toe sandals to finish the off the outfit , its just a shame i cant sit in the garden dressed like this the neighbours...
    ukgirlyboy ukgirlyboy 51-55, M 6 Responses Jul 12, 2013

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    Sunday

    On Sunday I had half a day of work and after that I went to town to do a little shopping. So when i left home I packed a simple little bag of clothes that I could change into.  I wore my pink runners and black jeggings with a pink thong and for a top I wore a dusty rose colored...
    Brandie1960 Brandie1960 41-45, M 1 Response Apr 23, 2013

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    It's Home Alone Time Again

    Once again I have the house to myself, for the next 24 hours or so. Right now I am dressed in an office-style outfit, consisting of a close-fitting grey V-neck blouse, which shows my boobs well, and a lined navy knee-length pencil skirt, with smooth pantyhose that feel wonderful...
    davina1407 davina1407 56-60, M 3 Responses Jul 11, 2013

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    What I Wore Last

    It was a few weekends ago now but I wore a pink and black bra and pantie set. Bra was low cut and had a frilly edge. Over the top I wore a blue dress with white sleeves. Felt perfect! I usually wear panties under my boy clothes as well.
    brentteenboy69 brentteenboy69 18-21, M 4 Responses Sep 15, 2012

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    Last Night (aug 27)

    I need to go shopping for one of those wing bras, the kind you wear that tape to your sides with nothing in the back. Mistress Lady Blue apparently wanted me to go a very little glam last night; she requested I wear a dress I have that's a long velour dress, slim, with...
    AliciaHalfcat AliciaHalfcat 36-40 Aug 27, 2012

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    For My Future Friends.

    Hi everyone. I just recently joined this website. I have 0 friends but I hope that changes in due time. I don't no what most crossdressers wear so I joined this group to play a little game to get to know each other. So please comment what you last wore when cross dressing
    YoungFreeSingle1 YoungFreeSingle1 18-21, M 3 Responses Jul 6, 2013

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    New Years Eve

    i wore a low cut black top, knee length black skirt, new 30 denier tights and high heeled ankle boots, just a shame i had nowhere to go
    ukgirlyboy ukgirlyboy 51-55, M 2 Responses Jan 1, 2013

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    Last Night

    I was able to dress as Kimmi last night and as usual I loved it. After I picked out the skirt and blouse I was going to wear I started putting on my under garments.  I started with a white thong and tucked my man parts between my legs.  Next I put on a matching white pantie (I...
    KimmiCD KimmiCD 41-45, T 6 Responses Jan 25, 2013

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    This Is What I Last Wore Out.

    I am the one on the left and that is the outfit that I wore last a few days ago but with tan hose and black knee high high heel stiletto heel boots when I went to a club to meet new friends. I just love dressing up and going out, no more hiding behind closed doors for me. This...
    RobynTheBeautiful RobynTheBeautiful 41-45 3 Responses Oct 1, 2012

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    Expecting Visitors???

    Well, I might be expecting visitors today, so I thought that a quick change option would be advisable. Normal top, but with a lovely skimpy pair of peach coloured panties, nude pantyhose and a short, black pleated skirt. Skirt off in a flash and jeans pulled on - sorted for any...
    AnnaliseB AnnaliseB 31-35, T 3 Responses Mar 7, 2013

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    My last time I was fully dressed was yesterday.

    I dress everyday in nappy(diaper). White bra and panty set with a white camisole with lace on the bust. Yesterday was no different with a blue dress over the top. On my feet I had blue sandles with a bar on top. I don't wear makeup or a wig. I know I don't pass but I rarery go...
    babyannie57 babyannie57 56-60, M Apr 11

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    Happy New Year !! So my first ever girl new year

    and woke up feeling amazing. Dressed in my red padded pushup bra ,red nylon and lace boyshort panties,tan knee high nylons, black skirt, white sweater,black ballet flats. Also glue on nails (3rd time ever) done in red, and red toe nails, my make me pink maybeline lipstick, 2...
    JeanW1 JeanW1 56-60, M 2 Responses Jan 1

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    Last Night (september 2)

    Wing bra has been obtained, as well as some cute black knit fall/winterish slipper/boot contraptions - alas none of these were able to make their way into my stash last night, so I made do with a rufflish kneelength purple cotton skirt, and a knit black tank top. Of course...
    AliciaHalfcat AliciaHalfcat 36-40 Sep 3, 2012

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    Saturday 12/1/2013

    today im wearing white bra and matching knickers, low cut top, jeggings, socks and boots what i call smart but casual got some housework to do later
    ukgirlyboy ukgirlyboy 51-55, M 1 Response Jan 12, 2013

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    Eye Of The Tiger (print-dress)

    I cross dress daily, but last time I went 'big' was this past Saturday. My ex girlfriend has been wanting to introduce me to her new boyfriend. She knew Genivieve well and is quite the Diva so she taught me quite a bit about fashion, make-up, etiquette and so on. In any event...
    genivieveleduc genivieveleduc 46-50, T 5 Responses Sep 27, 2012

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    Last Time

    Pretty shy with this as its fairly new for me having my wife accept my feeling feminine sometimes. It was a couple weeks ago I wore the new dress she bought me with red panties my toe nails red also. Still feel really nervous having her see me dressed
    JeanW1 JeanW1 56-60, M 2 Responses Sep 2, 2013

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    What I Wore When I Was Crossed Dressed Out In Public.

    This is my new white outfit. A friend picked this out for me and I tried it on in the shop and I had to get it. These pics where taken last Thursday night when we went for more shopping. http://www.flickr.com/photos/47209402@N04/10096653895/in/photostream http://www.flickr.com...
    RobynTheBeautiful RobynTheBeautiful 41-45 1 Response Oct 5, 2013

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    Amazing Day

    all day in the first dress I have ever had or worn. white thong barely black pantyhose, ( finially cool enough to wear pantyhose) my blue maxiedress black ballet slippers, red toe nails, pink lipstick, Paris Hilton's can/can body spray, white satin clutch purse. my wife bought me...
    JeanW1 JeanW1 56-60, M Sep 29, 2013

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    It's Been A While.

    Ever since my one computer died, I haven't been spending as much time down in my office on Sunday nights as I used to. Consequently, my time to be Me has suffered.  Not tonight.I'm about to try to frankenstein a bunch of computers together to get the broken one working again...
    AliciaHalfcat AliciaHalfcat 36-40 2 Responses Nov 17, 2013

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    Cowl Neck Sweater Dress

    The last time i cross dressed i wore a sage colured sweater dress from VS. UNDER IT I HAD ON VS WONDER BRA B CUP AND MATCHING PANTIES. i CHOOSE ANNE KLIEN BROWN RIBBED TIGHTS AND SOME GREY JESSICA SIMPSON ANKLE BOOTS TO FINNISH THE LOOK. As soon as i was dressed i put a 6 in...
    mical7 mical7 31-35, M 7 Responses Nov 25, 2012

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    Fun Time

    I last wire some pink lacy panties, some tan coloured tights which added to my legs, they made them look sexy, a black nightie that came to my high thighs, then black 4 inch heels, anyone who wants to see message me and I can add you on kik :) Have fun girlies! :) xx
    Crossdressheels Crossdressheels 18-21 2 Responses May 13, 2013

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    Tonight - all weekend I wanted to be a little

    more partyglam and wear a dress that was one of the first things in my collection and that I never wear because it's mostly backless (little straps) and I never had a bra that worked with it successfully. But now I have the form prosthesis with clear straps so I can wear that...
    AliciaHalfcat AliciaHalfcat 36-40 3 Responses Jan 20

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    Dressed Again Today

    Hi everyone. I am feeling so soft and feminine today. I am wearing my purple lace panties matching pushup bra, tan pantyhose, grey slacks, purple tee shirt. It feels so good to not have to hide from my wife now. Thank-you for this place too. Its nice to know I am not the only one...
    JeanW1 JeanW1 56-60, M 1 Response Sep 26, 2013

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    Last night for my date at the local t girl

    friendly club I was wearing a Red dress, black tights and heels. Felt wonderful being out fully dressed and the outfit looked lovely :) The date was fantastic ;)
    LucyTG LucyTG 26-30, T 3 Responses Mar 22

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    Nearing 2 Weeks

    Been dressing everyday for 2 weeks now. Just home from work showered and dressed. Wearing my black padded pushup bra, teal lace bikini panties, black spandex mini skirt, grey tshirt, black ballet slippers. My toe nails are red, putting on my maybeline make me pink lipstick. I am...
    JeanW1 JeanW1 56-60, M Oct 2, 2013

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    What I Wore Last Time

    I was wearing the outfit you see in my avatar, which was taken in a park, I love being dressed up in public. Anyway last time I got the train into the big city all myself to meet friends there and it is a 2 1/2 hour trip. I enjoyed the trip so much I forgot I was wearing 4in...
    RobynTheBeautiful RobynTheBeautiful 41-45 5 Responses Jul 3, 2013

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    Yesterday was very warm,

    mid 70's and breezy so I took a walk around the park. About a mile loop. Quite crowded with others out enjoying the first nice days of spring. I wore my yellow Adidas running shoes with white bobby sox. A light blue vertical ******** in varying shades of blue with a touch...
    burkaboy burkaboy 26-30, M 5 days ago

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    Wow, this new interface is.

    .. something... Anyway - first time go go full up Me tonight. So, the rundown: Red cotton VS thong. Red wire-free Curvations bra, with my forms inside. Black stretch miniskirt (it's midthigh). White shortsleeve blouse with a sort of white dot pattern on it. Black heels with...
    AliciaHalfcat AliciaHalfcat 36-40 Jan 12

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    Last Time Dressed

    Dark brown pantyhose, light red skirt, red bra with pads, seethru white blouse and a smile.
    cdsparky cdsparky 66-70, T 1 Response Jan 1, 2013

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    Lesse, let me list out what I am wearing

    as I type this... Nine West Blue Indigo Martina pumps Blue G-string from Victoria's Secret Blue and White lace hip panties Off white long/tall pantyhose Blue lace bra from Victoria's Secret White Lace and Satin top Eyeliner, shadow, red lipstick, blue nailpolish. ... and a...
    wistfulmiles wistfulmiles 51-55, M 1 Response Mar 23

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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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    Tonight (Mood Lighting)

    Slowly I am making more floor space in my office. Overtly it is to get it complete.  Realistically it's to give more room to pose in front of the camera.I was down here for an hour and some odd not knowing what I wanted to wear.   Slowly an outfit began to assemble: black...
    AliciaHalfcat AliciaHalfcat 36-40 2 Responses Sep 30, 2013

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    Right now I am wearing some shiny black tights

    with a garter belt and stockings over that. I have on a black 48DDD soft cup bra with two sets of breast forms inside (I like to have a big bust that bounces), Over my bra I am wearing a black chiffon blouse that has ruffles. Over my stockings, I am wearing a red petticoat with...
    kathej kathej 66-70, M 10 Responses Apr 7

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    Eye Of The Tiger (print-dress)

    I cross dress daily, but last time I went 'big' was this past Saturday. My ex girlfriend has been wanting to introduce me to her new boyfriend. She knew Genivieve well and is quite the Diva so she taught me quite a bit about fashion, make-up, etiquette and so on. In any event...
    genivieveleduc genivieveleduc 46-50, T 3 Responses Sep 27, 2012

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    Feeling Free

    i was wearing red capri pants by lee my thigh high suntan and pair white vans tennie padded pantie my breast forms 40 c cup and white pull over tank top to show breast off i had bra on
    debbiehose debbiehose 56-60, M 4 Responses Sep 4, 2012

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    Me Crossdressing?

    I myself have not dressed yet but want to....I get turned on sometimes by crossdressers and or TVs You do good work keep it up
    Ticklor Ticklor 61-65, M 7 Responses Oct 1, 2012

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    Today

    hi everyone today my black Vs bikini panties, my black padded pushup bra with lace trimmed cups, barely black pantyhose, long black skirt. red tshirt ballet flats, my lipstick (is make me pink) my wife gave me a pedicure this morning with pink polish
    JeanW1 JeanW1 56-60, M 2 Responses Nov 10, 2013

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    Related Experiences

    Whatever I was wearing that day, minus the jean though.
    TheObviousAnswer TheObviousAnswer 18-21, M Mar 29

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    I always wear an adult diaper to bed now. In the warmer weather with just a T-shirt. When it is cold I put on nice flannel pajamas with footies on over my diaper.
    kellycares kellycares 41-45, F 3 Responses 3 days ago

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    Tights are nice.....however I'll change from my daytime ones to another pair
    tightlybound tightlybound 51-55, M Mar 28

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    Nude feels good soooo comfy
    adamsoweird adamsoweird 18-21, M 2 Responses Mar 28

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    In the buff all my life. Otherwise I get too hot.
    CharlieKilo1 CharlieKilo1 46-50, M 1 Response Apr 8

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    A onsie :) :) :) :) :) :) :)
    JadenLangVageta JadenLangVageta 13-15, F 1 Response Apr 8

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    Well, right now, nothing XD hahaha
    DrowningInEmotion DrowningInEmotion 13-15, M Apr 8

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    You entered: Talynn _____ _______ You like to control everyone within your influence, to shape things to your own liking. If positive, you develop high spirituality, as you have a...
    Talynn Talynn 18-21, F 5 days ago