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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 661 People

    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 1 Response Jul 23

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    I am wearing right now high waisted skinny jeans

    and a gold shimmery crop top.
    0hBrandie 0hBrandie 41-45, M 2 Responses Oct 24

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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 51-55, T 3 Responses 5 days ago

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    My new job has me working weekends,

    so my days off for the time being are Wednesdays and Thursdays. So I spend some of the time figuring out what I'm going to wear after I get out of work on Saturday night. I may wear this to the bar.
    PennySterling PennySterling 51-55, T 7 Responses Oct 15

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    A followup to my previous post.

    Here's how I looked out at the second club we went to last night. I'm not sure what made the bigger impression: the hair, the nails, or the 'girls.' I got the hair at one of the ubiquitous Halloween shops that pop up like toadstools this time of year. I've always nad a 'thing...
    PennySterling PennySterling 51-55, T 2 Responses Oct 19

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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 10 Responses Oct 24

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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 51-55, T 3 Responses Oct 23

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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 12 Responses Jul 23

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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 56 Responses Jul 22

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    Grey colored flutter skirt from Ricki's with a

    black and white horizontal striped cap sleeve Top from Blue Notes and a black 2 button blazer with 1/2 sleeves. Shoes were 1" heeled black sandals from Walmart. Panties and bra were a matching set from Wamart too featuring purple and white with black polka dots. Wore this...
    0hBrandie 0hBrandie 41-45, M 1 Response Aug 8

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    Wearing it now. A bauge

    and black striped dress. Black pantyhose with black flats. Underneath I have light blue panties on and a black panty girdle. A purple bra and stretch cami to smooth everything out.
    mat2Robin43 mat2Robin43 51-55, M 2 Responses Aug 9

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    Seeing I dress as a woman 99% of the time,

    I consider going out as a male to be crossdressing. Last month I wore grey slacks and a blue blazer, white button down, rep tie and brown loafers. I felt so weird.
    josilver josilver 56-60 4 Responses Oct 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 7 Responses Jan 28, 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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    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 7 Responses Jul 12, 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 10 Responses Jul 1, 2013

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    I am currently wearing my new hi heels I got

    yesterday,blue panties and a leopard print bra and a robe.
    lapsteel lapsteel 41-45, M 2 Responses Oct 2

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    I wore a Green maxi dress with nude coloured

    sandals. Underneath I had a matching black bra and knicker set. I really felt amazing and stayed in the outfit for the whole day. Love the sway of a maxi dress :)
    GirlyLisaTG GirlyLisaTG 26-30, T 1 Response Aug 18

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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 4 Responses Dec 14

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    Finally home from work

    and it's on with a nice green skater dress, 80 denier tights and a matching pink bra and panty set. I'm looking forward to a weekend of being Lisa, hoping to venture out shopping fully dressed to freshen up the wardrobe :)
    GirlyLisaTG GirlyLisaTG 26-30, T 5 Responses Oct 24

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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 10 Responses Oct 23

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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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    I wore a pair of black leggings,

    panties a white pushup bra, a nice t-shirt and a pair of sperry boat shoes with my legs shaved. I wish I had someone to do my makeup but I sadly have no one to do that for me :(
    cdux cdux 18-21, M 1 Response Oct 27

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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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    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

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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 2 Responses Jul 20

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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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    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 5 Responses Oct 5, 2013

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    The day after my custom-made dress showed up,

    I got this dress back! I had purchased it from a vendor at a street fair, but it was too tight in the chest, so I sent it back to them and they gave me the next larger size. I was wearing a black slip underneath it, but I realized it was too long, so I took it off. The slip...
    PennySterling PennySterling 51-55, T 4 Responses Aug 27

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    Yyntnt80 Yyntnt80 46-50, M 1 Response Nov 9

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    I had on a black leather skirt

    that went to my knee and black and white blouse white open bottom girdle tan stockings white nylon panty white playtex 18 hour bra wig make up and black 3" heels
    Betty9953 Betty9953 51-55, M 6 Responses Aug 21

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    First time in a long

    while yesterday I was able to dress up for a little bit while doing laundry... not even in anything special, black yoga pants with a folded down pink waistband and a white lace-trim shirt with pink sports bra and pink thongs under but I feel reenergized and happy today
    AliciaHalfcat AliciaHalfcat 36-40, T 1 Response Oct 27

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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

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    This is getting to be a difficult question to

    ask, since I incorporate so many feminine things in my daily attire. For example, my watch and purse are visible. Some of my sweaters are women's sweaters, as are most of my socks. And, of course, my undies. Sometimes it gets so hard to dress in the morning.Sometimes it...
    PennySterling PennySterling 51-55, T 4 Responses Aug 16

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    stefiecdtv stefiecdtv 51-55, T 16 Responses May 27

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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 4 Responses Jun 25

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    I'm getting dressed this evening.

    Having a new friend round. I have painted my toenails red and will wear a pair of see through blue knickers, very tight denim booty shorts, a short blue top with a red bra and high heeled sandals. What do you think?
    deleted deleted 26-30 4 Responses Jul 28

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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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    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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    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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    I'm wearing it right now!

    It's my brand-new, custom made dress from eshakti.com. I love it! And underneath it I'm wearing my rago waist cincher with opaque black stockings and a pair of demure pumps. I tried a lot of different looks, but I think I like using my green pashmina as a belt, with the pearls...
    PennySterling PennySterling 51-55, T 3 Responses Aug 26

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    I have just got out of bed.

    I was wearing a thong and animal print shortie nightie. Now I am dressed in a red bra, a very short blue vest and a pair of see through blue knickers - havn't had time yet to select a suitable miniskirt!
    deleted deleted 26-30 3 Responses Jul 28

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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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    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

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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 8 Responses Jan 9, 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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    tvCorinne tvCorinne 51-55, T 9 Responses Oct 23

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    Right now I'm wearing a denim mini skirt navy

    lace panties and navy bra top
    holly39 holly39 36-40, M Jul 23

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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 51-55, T 3 Responses Oct 29

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    Related Experiences

    I am just plain interested about what you wear
    bacon62 bacon62 51-55, M 8 Responses Nov 25

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    uhh.............khakis.....
    kiratropolis kiratropolis 18-21, F 6 Responses