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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 745 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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    ​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 14 Responses May 27

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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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    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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    ​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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    on and off all day today

    while finishing laundry, black stretch short shorts under my favorite purple tee, because it's fast to put on and take off.
    AliciaHalfcat AliciaHalfcat 36-40, T 4 Responses Feb 1

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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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    It has been a while since I went out.

    I was in a long purple dress, black 4 inch heels and blonde hair. I lost my brooch and wished I replaced it with a slender red belt. That would have been so nice, and the bar owner likes to see me in that dress too. A boyfriend wants to go driving and dancing as I wear my...
    priebecl priebecl 61-65, M 3 Responses Jan 5

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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 4 Responses Jun 9

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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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    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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    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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    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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    A black and white cap-sleeve striped dress over

    black capri leggings, and black sneakers.
    AliciaHalfcat AliciaHalfcat 36-40, T Feb 9

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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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    I wore a white garter belt with dark grey

    stocking. I had a blue set of lacy panty with matching bra. Then I wore a spandex girdle helping to tuck my belly. With my wig and make up ( a little base, eyes lashes and a dark red lipstick). I was perusing a lingerie catalogue while sipping wine and fell asleep en femme. So...
    SoumisCH SoumisCH 41-45, M 4 Responses Aug 23, 2014

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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 69 Responses Jul 22, 2014

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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 2 Responses Jun 4

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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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    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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    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 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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    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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    mat2Robin43 mat2Robin43 51-55, M 9 Responses Jun 13

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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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    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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    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 4 Responses Sep 27, 2012

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    prudance prudance 51-55, T 1 Response Jun 17

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    I am on a mid-winter business trip to a place

    where it was warm and sunny. So I had to get out and enjoy the sun. I went to Payless and bought a pair of sandals (male style). Finding a place in the mall where I could sit with my back to most people, I removed my male shoes and socks, which revealed my pantyhose covered...
    cdsubalice cdsubalice 56-60, M 5 Responses Feb 11

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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 7 Responses Jun 17

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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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    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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    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 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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    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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    Jeans and a t-shirt - wait oh you mean

    as a girl ;-) Denim mini skirt, purple crinkle cami, panties and bra, hose and 4" heel, 1/2" platform pumps.
    VeronicaJane1 VeronicaJane1 31-35, T 1 Response a week ago

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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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    ​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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    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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    mat2Robin43 mat2Robin43 51-55, M 13 Responses Jun 17

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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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    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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    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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