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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 625 People

    Last Time Dressed

    Since I wear panties 24-7 I am technically always cross dressing. The last time I was fully dressed I had on a bra, panty and garter belt set with beige stockings a just above the knees black skirt with a pumpkin colored blouse and finished it off with a pair of 5 1/4" cream...
    BarbieCD BarbieCD 41-45, T 4 Responses Aug 30, 2013

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    My new Rago waist cincher,

    black seamed stockings, black satin opera gloves, and black thong panties. The panties were only on for the briefest (get it) of time. I wore this while playing on Skype with my girlfriend.
    PennySterling PennySterling 51-55, M 2 Responses May 6

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    white pocket Tshirt cornflower blue bikini

    cotton panties dark blue denim with spandex miniskirt
    wcurnow wcurnow 46-50 2 Responses Jun 10

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    Red lace boyshorts, and white thigh hi

    stockings. Still wearing them, in fact
    PennySterling PennySterling 51-55, M 1 Response May 3

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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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    Right now I am wearing taupe No Non-Sense

    pantyhose without underwear, a black Rago 1294 HWOBG, and Black 42C plunge bra by Lane Bryant under my male things.
    CrossdresserLauren CrossdresserLauren 46-50, T 2 Responses 3 days ago

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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...
    atoyboy atoyboy 18-21 1 Response Apr 14

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    stefiecdtv stefiecdtv 51-55, T 12 Responses May 27

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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

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    Well today 07/20/14 I am wearing a navy blue

    and white polka dot long skirt Navy Pantiehose a boyshort microfiber pantie. a smooth Push Up Plunge Bra and a orange women's ruffeled top and 4 inch espadrille shoes.. My wife does not force me to dress like a woman, I do it because I like wearing women's clothing. I like...
    serinalynn serinalynn 61-65, M 1 Response 4 days ago

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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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    Monday, March 3, 2014.

    I came home from hunting and it was a beautiful day. My wife was wearing her new shorts she bought on vacation and I wanted to wear my short shorts but my family was here so I couldn't. This is what Stefie is wearing underneath her ugly man clothes.Again, I hope no one is...
    stefiecdtv stefiecdtv 51-55, T 3 Responses Mar 3

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    I just woke up so while sitting hear drinking

    my coffee its simple... just wearing my bra and all in one a thong and some suntan pantyhose. I have on some satin gym shorts and a satin top... gota go need some relief later... jilly
    jilliank jilliank 51-55, M 2 days ago

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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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    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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    I'm wearing this lovely dress at the moment,

    over a black triple layer petticoat, black lacy suspender panties, black stockings and my new red heels!! Just been sitting and watching a movie with my wife. What a great way to relax!! XX
    capeme capeme 46-50, M 6 Responses Apr 16

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    This afternoon. Before I did battle with a

    large cucumber. I know there's not much continuity of styles but Im just starting to build my wardrobe.
    PennySterling PennySterling 51-55, M 4 Responses May 2

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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 6 Responses Jun 2

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    a pair of white lace panties with matching 40 c

    bra, light blue green t shirt brown knee length skirt. tan hose and brown wedge heels. with French tip nails and clip on earrings.
    jamie172 jamie172 46-50, T 6 Responses Jun 23

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    Today while doing my chores.

    My wife chose for me to be a pretty gurl. 
    stefiecdtv stefiecdtv 51-55, T 6 Responses May 16

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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 4 Responses Jul 15

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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 10 Responses 3 days ago

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    Today While Webcamming

    I wore and older red cocktail dress we had bought for my wife for a Marine Corps ball several years ago and cute, red Fredericks heeled sandals. I had my makeup on and my jewelry and of course my wig with a cute silver barrette in it. Underneath I had on pretty reddish pink...
    stefiecdtv stefiecdtv 51-55, T 7 Responses Jan 9, 2013

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    Whatever My Wife Tells Me To Wear

    Yesterday, 6-30-13, my wife wanted me to wear what she made me put on Friday morning for my chores. It was this purple, blue and black colored top, short bluejean skirt, Thigh high stockings, waist cincher w/ garters, red bra and panties, my blue-striped 5" open toe pumps. Of...
    stefiecdtv stefiecdtv 51-55, T 12 Responses Jul 1, 2013

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    Thursday, May 22, 2013: That morning I had

    gotten a call from the company I was interviewing with for a job. They had an assignment for me: come up with a story idea for one of two collegiate sports teams I don't follow, in sports that were off-season. "Sure," I said. Can I get it to you on Monday?" "Tomorrow," I was...
    PennySterling PennySterling 51-55, M 1 Response May 23

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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 51-55, M 4 Responses Jun 25

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    7-1-14I wore the brown dress

    but my wife didn't like it. She wanted me to be sluttier. I had to put on her slinky, black cocktail dress and of course change the shoes.
    stefiecdtv stefiecdtv 51-55, T 6 Responses Jul 2

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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, T 3 Responses Jan 20

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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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    A black gothic lolita blouse,

    black and red plaid skirt with red plaid pockets hanging off the black corset, and of corse black thigh high socks
    Poopoohead17 Poopoohead17 18-21, M 2 Responses May 30

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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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    Well I dress every day.

    .. So today I tried something a little different. It all starts with a satin thong panty. Then long-line bra filling out a ‘D’ size and ivory all in one; I like the tightness and shape that it is giving me body. My favorite pantyhose; L’eggs Taupe all sheer..... I shaved...
    jilliank jilliank 51-55, M 3 Responses Apr 2

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    That was Easter. Lovely warm day.

    I wore a tan dress with matching bonnet bedecked with flowers. Frilly collar light tan gloves. While I seldom wear anything under, this time I wore tan pantie hose and low tan leather heels great for walking. I met a nice gentleman of close to my own age who took me to an...
    atoyboy atoyboy 18-21 1 Response Apr 22

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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 7 Responses Sep 15, 2012

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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 8 Responses Jan 28, 2013

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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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    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 4 Responses Aug 5, 2013

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    Last night I wore a mid length mini skirt.

    ..bright pink lace backed panties with lycra front in black panties....black stockings and a green short shirt from areopostle....I loved it! I wore 4 inch heels in black and I felt like a girl...really did...I wanted a man to seduce me soooo BAD!!!
    biman3391 biman3391 41-45, M 2 Responses May 28

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    7-2-14This morning the Queen made me wear my

    maid outfit to finish cleaning the house before our guests get here for the weekend.She made me tired from the list of things to accomplish, anyone want to join me for a nap?
    stefiecdtv stefiecdtv 51-55, T 6 Responses Jul 2

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    Rago waist cincher, black seamed stockings,

    knee-length slip and calf-lenght purple sheath dress. Everything but the cincher was purchased for my by my girlfriend.
    PennySterling PennySterling 51-55, M 2 Responses May 16

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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 4 Responses Jul 6, 2013

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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

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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 4 Responses Oct 5, 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 8 Responses Jul 12, 2013

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    daysleeper2 daysleeper2 51-55, M 8 Responses Jun 1

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    Second outfit, which I wore

    for the rest of the day was a top and jeans, fully femmed out though, just casual :-)
    Abilohman Abilohman 26-30 2 Responses May 23

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    what your fav thing to where

    when you crossdress?
    Zoe24 Zoe24 22-25, M 6 Responses Apr 29

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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 1 Response 2 days ago

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    A wedding gown was the first outfit.

    Bought it cheap and a friend altered it to fit :-)
    Abilohman Abilohman 26-30 May 23

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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 4 Responses May 27

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    My red and black bra with black thong

    and thigh highs that feel so good on my legs.
    stellacd132 stellacd132 18-21, M 5 Responses May 13

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    Right now I am wearing my favorite tight black

    underwire bra in 42C, sheer white full slip and black pantyhose with no panties on. I just love how it feels against my skin. So sensuous.
    CrossdresserLauren CrossdresserLauren 46-50, T 1 Response Jun 4

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    Twittlebug Twittlebug 22-25 1 Response May 16

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