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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 752 People

    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 10 Responses Jul 12, 2013

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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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    Rago high waist open girdle,

    black stockings, pretty little black M&S bikini panties and a black bra. Heaven !
    BrightLight750 BrightLight750 46-50, M 6 Responses Jul 10

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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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    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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    prudance prudance 51-55, T 1 Response Jun 17

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    tvCorinne tvCorinne 51-55, T 9 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'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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    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 14 Responses Mar 20

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    Away Overnight.

    Went Interstate for one night and as well as the obligatory panties, since that's all I have, with matching push up bra in pink, I also took my cotton pink nightie with little whit love hearts, nothing fancy... Also wore some Victoria's Secret "Hello Darling " body spray...
    tammy96 tammy96 51-55, M 4 Responses Aug 23, 2013

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    I wore a red padded bra,

    red cotton panties, white camisole, suntan thigh-high stockings, a black pencil skirt, a draping light blue top, and my favorite black 3 1/2 inch pumps.
    Nyssa59 Nyssa59 56-60, T 5 Responses Dec 18, 2014

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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 7 Responses Jun 14

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    I know it's too cold

    for the top I wore outside but its not in the warm laundry area of the basement. Off white and black one shoulder top (strapless bra) with jeans and wedge flip flops.
    AliciaHalfcat AliciaHalfcat 36-40, T 1 Response Feb 15

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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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    I'm wearing two pair of shiny pink leotards

    over two pair of shimmery white tights, three pair of leg warmers with my pinks ones on top and then matching pink spike high heels. My little bulge is wrapped inside a small lycra sock.
    LadyLycra LadyLycra 18-21, M 22 Responses Mar 1

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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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    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 3 Responses Mar 20

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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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    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 8 Responses Oct 29, 2014

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    ​May 18th, 2015. I had about three hour break

    between taking my son to work and picking him up. The Queen told me to wear this and send her a pic. 
    stefiecdtv stefiecdtv 51-55, T 21 Responses May 27

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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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    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 1 Response Jun 23

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    capeme capeme 46-50, M 1 Response Jul 13

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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 3 days ago

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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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    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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    Yesterday I wore a gray sweater dress,

    pink panties, bra and high heels
    waringpntiestex waringpntiestex 56-60, M Jun 27

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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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    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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    mat2Robin43 mat2Robin43 51-55, M 12 Responses Jun 17

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    I wanted to go th whole way

    but school doesn't start until tomorrow so I'm watching my grandson. I did get a chance to put on what I wanted to wear though.I haved on a black thong, black shelf bra, thigh high stockings, my new skinny jeans, black camisole and brown/ornage blouse with belt. I wish I could...
    stefiecdtv stefiecdtv 51-55, T 2 Responses Jan 6, 2014

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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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    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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    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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    10-23-14This is what I'll be wearing tonight

    under my new dress my wife bought me. It has a white lace bodice and a short blue print bottom with capped sleeves. I think this is a good fit, although the dress is very short, because I'm tall. I think my stocking tops might show.I hope no one sneaks up behind me until I'm...
    stefiecdtv stefiecdtv 51-55, T 15 Responses Oct 23, 2014

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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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    capeme capeme 46-50, M 2 Responses Jul 13

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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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    ​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 70 Responses Jul 22, 2014

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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 5 Responses Jun 9

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    Thigh high socks from American apparel white

    lacy panties and nothing else
    deleted deleted 26-30 2 Responses Jun 4

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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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    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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    Right now I'm wearing a little black jumper

    over a white turtleneck, navy blue cable knit kneesocks, and black shoes. I feel good!
    schoolgyrlKaren schoolgyrlKaren 41-45 9 Responses Feb 12

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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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