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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 725 People

    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 13 Responses Mar 20

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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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    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 5 Responses Jan 31

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    I am wearing right now high waisted skinny jeans

    and a gold shimmery crop top.
    0hBrandie 0hBrandie 41-45, M 1 Response Oct 24, 2014

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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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    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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    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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    ​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 13 Responses Jul 23, 2014

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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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    ​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 73 Responses Jul 22, 2014

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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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    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 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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    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 2 Responses Mar 20

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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 19 Responses Mar 1

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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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    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, 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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    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 4 Responses Oct 24, 2014

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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 51-55, T 8 Responses Mar 20

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    stefiecdtv stefiecdtv 51-55, T 16 Responses May 27, 2014

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    In such a horny mood tonight,

    just wearing a pair of purple brief knickers and a pair of blue 3inch high heels. Feel amazing, message me :)
    GirlyLisaTG GirlyLisaTG 26-30, T 8 Responses Dec 29, 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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    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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    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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    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 4 Responses Sep 27, 2012

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    tvCorinne tvCorinne 51-55, T 10 Responses Oct 23, 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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    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 6 Responses May 12

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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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    Yyntnt80 Yyntnt80 46-50, M 3 Responses Nov 9, 2014

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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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    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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    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 3 Responses Apr 14

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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 6 Responses Nov 25, 2012

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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 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, 2014

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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 5 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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    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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    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 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 2 Responses Oct 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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    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 3 Responses Oct 27, 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'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 8 Responses Oct 29, 2014

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