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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 763 People

    I'm currently wearing a white satin victoria's

    secret 38b strapless bra, a white satin string bikini, and my favorite white satin nighty. I love the feel of the fabric, and it makes me feel like a sexy, gorgeous young girl.
    faellorien faellorien 26-30, M 5 Responses Jun 2, 2014

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    tvCorinne tvCorinne 51-55, T 11 Responses Oct 23, 2014

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    Currently wearing my black "Audrey" dress over

    a puffy long sleeved chiffon body suit, shiny sheer tights and my favourite black maryjane platform heels :)
    capeme capeme 46-50, M 5 Responses May 12

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    I wore a purple waist trainer corset purple

    thong hold up stockings a lil black dress 5" heels
    liziemary liziemary 36-40, T 2 Responses Jun 4

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    Black belted dress, white pantyhose,

    Nine West black patent pumps, black zippered panty, pearl necklace.
    wistfulmiles wistfulmiles 51-55, T 4 Responses Aug 14

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    clothes for today .Today i got up early to do

    some household jobs i put on a red pencil skirt with a skinny black belt a black scoop neck short sleeved t shirt underneath i have on some nude body shaper tights an all in one black underwired body shaper and black half slip on my feet i have some black court shoes with a...
    daverick daverick 51-55, M Jul 19

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    I wore a satin padded

    and non padded bra, satin pantie, green long satin dress and then over that a gold long satin dress. Further eith liquid liner, mascara, kajal, eye shadow, lipliner, lipstick amd foundation. Then I wore a pair of earrings and finslly a long brown wig. I carried a clutch alomg...
    Pinkygir Pinkygir 16-17, M Jun 17

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    mat2Robin43 mat2Robin43 51-55, M 11 Responses Jun 17

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    I'm wearing this right now.

    It's part of my Halloween costume. I'm transgendered, yes, but this is NOT how I normally dress. I do NOT normally dress this sluttyOn the outside. :)
    PennySterling PennySterling 56-60, T 9 Responses Oct 29, 2014

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    mat2Robin43 mat2Robin43 51-55, M 8 Responses Jun 13

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    capeme capeme 46-50, M 4 Responses Jul 13

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    prudance prudance 51-55, T 1 Response Jun 17

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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 10 Responses Sep 15, 2012

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    The Queen text me and said pink today.

    Pink g-string panty, pink bowtie at neck corset, beige stockings and pink stiletto heels.
    stefiecdtv stefiecdtv 51-55, T 7 Responses Jun 9

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    ​Short shorts;I just love slipping short

    shorts on in the morning. My wife said the pink shoes really didn't work so I should put some black ones on, What do you gurls think?Pink Pumps;Black Pumps;
    stefiecdtv stefiecdtv 51-55, T 14 Responses Jul 23, 2014

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    Well summer has not arrived quite yet,

    but I have felt myself drawn to one of my cutest new summer dresses today. It's a rather short, black flirty dress, with small white polka dots, a cinched in waist, with a soft, satin lining that feels delicious against my skin. Underneath, I have on a simple, but cute, black...
    AnnaliseB AnnaliseB 31-35, T 3 Responses Apr 22, 2014

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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 11 Responses Jul 12, 2013

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    Last night my wife wanted me to wear short

    white shorts, a leopard print top, pink VS tanga panties and extreme cleavage bra. Of course, makeup wig and accessories.How did I do?
    stefiecdtv stefiecdtv 51-55, T 5 Responses May 27, 2014

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    My cork heels black footless tights

    and a red pencil skirt. Black top and black bra. Blonde wig with braided pig tails with pink bows.
    cdjo cdjo 41-45, M 9 Responses Aug 17, 2014

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    I was dressed in my new matching gown with my

    wife, with blue mascara, purple eye shadow, light red blush, making love all night into this morning
    Melissa11520 Melissa11520 41-45 Apr 14

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    Right now, enjoying a bit of me time

    since my wife and her boyfriend have gone off to bed upstairs... short jean shorts and a white tank top with a red lace one with silver anchors all over it over top, and black wedge sandals. just finished doing my face and painting my nails to match my lipstick. it's a shame it...
    AliciaHalfcat AliciaHalfcat 36-40, T 4 Responses 3 days ago

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    so a few weeks ago I got busted,

    my activities found out by my wife. I was compelled to execute a purge and trash a lot of my wardrobe in the middle of the night under her supervision... but I didn't really get rid of everything. just the clothes I no longer wanted, but she doesn't know that. I still...
    AliciaHalfcat AliciaHalfcat 36-40, T 7 Responses Jan 31

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    ​A pair of grey jeans

    and a sweater. That's when I crossdress.Cute skirt, tights and a red top? This is me. This is who I am. 
    PennySterling PennySterling 56-60, T 8 Responses Mar 20

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    Not feeling so great today

    so it's a day on the sofa wearing a nice pink satin robe with a black babydoll and matching panties on underneath. Feel so feminine :)
    GirlyLisaTG GirlyLisaTG 26-30, T 9 Responses Feb 21

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    Ahhh, i get it. I just have to start my own

    story to share what I wore last.Yesterday chatting with a friend from here
    babybearjean babybearjean 61-65, M 9 Responses Jun 17

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    What I Am Wearing Now

    The last time I crossdressed is ..... right now! In fact I am always dressed when I get on EP. I am wearing a short pleated brown wool skirt, white fluffy angora sweater, little white sockies, black high heal strap shoes, and a blonde shoulder length wig with a small braid on...
    bethanngirl bethanngirl 56-60, M 6 Responses Jan 28, 2013

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    A tight, blue dress, a long brown wig with

    caramel highlights, large silver hoop earrings, black tights, padded underwear, a red lacy bra, two inch heels, liquid eyeliner, gold/brown eyeshadow, mascara, foundation, blush, lip liner and lipstick in Dark Cherry. It was the first time in about a year and I really needed it...
    jessicavamp jessicavamp 41-45, M 4 Responses Apr 14

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    Thigh high socks from American apparel white

    lacy panties and nothing else
    deleted deleted 26-30 1 Response Jun 4

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    Dressed for the day maybe.

    I always like to go on EP dressed and browse readers stories today i got up early and got dressed to to do some house hold work and spend some time on EP i have on a navy pencil skirt and white 3/4 sleeve slash neck t shirt with a pair of black 3 inch heel shoes i have on...
    daverick daverick 51-55, M 3 Responses Aug 14

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    10-23-14This is my new dress the Queen bought

    for me. Its so cute, maybe a little to short. If my wife wore it I'd call it a turtle dress because it would only be two inches below the snapper.Then, for sleep she wanted me to wear my sexy long green nighty. I so love waking up stil wearing my makeup and wig. I would love to...
    stefiecdtv stefiecdtv 51-55, T 20 Responses Oct 24, 2014

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    I went out and bought a new pair of heels at

    Payless with a blue jean skirt thigh high and ken high boots
    jerbare jerbare 61-65, M 7 Responses Mar 20

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    Finally! I had a chance to get into something

    "more comfortable" last night for a few hours. God, how I miss crossdressing if I have not done it in a few weeks (or more =-( For last night I wore: a pair of medium black DIM stay-ups, a La Vie En Rose black thong, and a stretch lace/nylon Vogue 36-C bra with silicone...
    chantelletv2 chantelletv2 41-45, T 5 Responses Jul 15, 2014

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    Today was a white silk slip,

    panties, a white cotton blouse, beige calf length skirt, white knee highs, and brown ballet flats. The color coordination was spot on for what I wanted to achieve, and am very happy as a result.
    wistfulmiles wistfulmiles 51-55, T 3 Responses Jul 18

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    Rago high waist open girdle,

    black stockings, pretty little black M&S bikini panties and a black bra. Heaven !
    BrightLight750 BrightLight750 46-50, M 8 Responses Jul 10

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    ​Last weekend {7/18-20/14) my wife allowed me

    to dress for her. It was so much fun waking in the morning with my makeup and everything still on.7-18-147-19-14
    stefiecdtv stefiecdtv 51-55, T 66 Responses Jul 22, 2014

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    I kept it simple. A red satin blouse,

    red bra, black pencil skirt and taupe no-nonsense pantyhose with nothing on under them. I simply love the feeling. It is hot as hell today so I feel a little damp there ;). Makes me wonder how a GG feels when she is damp.
    CrossdresserLauren CrossdresserLauren 46-50, T Jul 31

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    It was so hot and miserable today,

    I took off my red blouse and black skirt and had to jump into a cool shower wearing a pair of tan pantyhose, red bra and full slip. I took off the slip to wring the water out of it as best as I could and put it back on. I figured that should keep me feeling cool while I hung...
    CrossdresserLauren CrossdresserLauren 46-50, T 2 Responses Jun 23

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    The other day I wore one of my Rago 1294 OBG's

    as a skirt. I also wore one normally, and a black satin bra. I had on a pair of black No-Nonsense tights without any underwear. It felt oh so luscious.
    CrossdresserLauren CrossdresserLauren 46-50, T 3 Responses Dec 14, 2014

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    Some days it is a pretty dress

    and others (today) it is jeans and a sweater. looking at the photo, you can see why!
    tvCorinne tvCorinne 51-55, T 12 Responses Mar 20

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    Thursday I wore my brunette hair.

    red lips (of course), a red blouse, black midlength skirt and 4 inch heels. It was a nice latte but I was in too much of a hurry to really enjoy it. (Too many things in my plate).
    priebecl priebecl 61-65, M 1 Response Mar 20

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    Yesterday I wore a gray sweater dress,

    pink panties, bra and high heels
    waringpntiestex waringpntiestex 61-65, M Jun 27

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    "I did yoga today.  Ok,

    sat around in yoga pants drinking wine."Wife asked if I was going to go down for a little while tonight - I said yes, mostly if only because I need to do a little laundry and take care of some bookkeeping on the computer, and pack my laptop up for work tomorrow.  She knows...
    AliciaHalfcat AliciaHalfcat 36-40, T 1 Response 2 days ago

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    I wore a matching black lace bra

    and thong, black garter belt with red back-seamed stockings, red knit mini-dress, black high heel pumps, blond curly wig, make-up and a pearl neckless. I poured a glass of white wine, watched some adult videos, and pleasured myself (all the way). I ended up having to wash my...
    Chefsteve69 Chefsteve69 56-60, M 5 Responses Jun 25, 2014

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    I just woke up so all I have on is a pair of

    white bikini panties and white tank top with breast forms.
    Michelle1976 Michelle1976 36-40, T 3 Responses Apr 26

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    Pretty simple this morning,

    in case I have to get out of it quick if the wife wakes up earlier than normal. Blue Baby doll nightie, Suntan Pantyhose and my Blue Patent Platform Pumps.
    jamie50 jamie50 51-55 6 Responses Jun 14

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    Silver satin chemise with black lace trim,

    black satin panties with silver lace trim, black satin robe and black thigh highs. I'm wearing it right now as I practice my makeup for a Halloween party to which I've been invited. It's at the house of a friend of mine who keeps asking me to join his ManKind Project circle. I...
    PennySterling PennySterling 56-60, T 3 Responses