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I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 869 People

    Today I decided to put on a silk mid-thigh

    flower print skirt, black No Non-Sense Smart Support pantyhose, black satin panties, black Rago OBG size 6X, a white silk blouse, a black 44C bra, my silicon forms, and 3" strappy heels. I feel so together.
    CrossdresserLauren CrossdresserLauren 46-50, T 4 Responses Oct 22, 2015

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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 8 Responses Jun 4, 2015

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    leggs4me leggs4me 51-55, T 9 Responses Oct 2, 2015

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    Hanes cotton Stretch Bra with forms hanes

    cotton panties Maurices tank top under crocheted sweater Maurices skinny jeans black knee length boots
    Jena1976 Jena1976 36-40, T 1 Response Dec 31, 2015

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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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    deleted deleted 26-30 Oct 7, 2015

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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, 2015

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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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    House to myself all night last night.

    Wanted to keep things casual, so panties, bra, silicone forms, Capri pants, 4" black pumps, long sleeve polo, full make up and straight, dark wig with bangs and auburn steak. It was chill all night in girl mode.
    annalisadt annalisadt 56-60, T 4 Responses Dec 12, 2015

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    Since the sons moved out,

    The Queen ordered me to steam clean the carpets in their rooms. Since its been so long since I got to dress she told me to wear pink to get my sissy on. Which pink outfit should I wear to do it gurls?And which stockings also loves? 
    stefiecdtv stefiecdtv 51-55, T 12 Responses Sep 15, 2015

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    I went out to lunch today with my wife.

    I had on flowered thong panties, thigh-high black stockings, a white bralette with moderate-sized falsies, a white tank top, a Land's End shirt (pretty male-looking but with buttons on the left) and two male items: pants and sneakers. Nobody noticed.
    tyrihans45 tyrihans45 66-70, M 2 Responses Oct 29, 2015

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    Saturday my wife and her boyfriend went out

    shopping and to lunch, to spend the day together and get a jump on the holiday season.  She went by Torrid and bought me clothes to open in private on Christmas, but mutually they wanted me to have one thing early - shiny cat leggings with pokey out ears, meow :)  so I...
    MirandaAlicia MirandaAlicia 36-40, T 5 Responses Oct 12, 2015

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    Panties and pantyhose,

    with black faux leather jeggings.
    sabrinainpink sabrinainpink 26-30, T Dec 2, 2015

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    right now I'm wearing thong pantie with yoga

    pants sports bra with c cup breast forms and a tee shirt
    jamie172 jamie172 46-50, T Nov 21, 2015

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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 4 Responses Apr 22, 2014

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    The Queen said we are wearing purple today.

    After my Daughter-in-Law drops off our grandson's clothes for the weekend, I think I'll put this on.Black pencil skirt, purple camisole, purple print top. Purple bra and thong underneath with thigh high stockings and black patent leather pumps. Of course I'll need my makeup and...
    stefiecdtv stefiecdtv 51-55, T 14 Responses Oct 15, 2015

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    my black and white bodycon dress mini,

    black bra and panties, 60 denier opaque pantyhose and my 4" black court shoes.
    joannekoften joannekoften 36-40, M 2 Responses Sep 30, 2015

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    leggs4me leggs4me 51-55, T 5 Responses Dec 7, 2015

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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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    this is what I wore this morning

    before work.that time of year for sweaters and leggings
    leggs4me leggs4me 51-55, T 1 Response Oct 2, 2015

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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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    ​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, 2015

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    Today VS Sport tights pink supper soft panties

    and matching Very Sexy pushup bra with my C forms and save the tatas t-shirt. So comfy today.
    thisismeisthisyou thisismeisthisyou 41-45, M 2 Responses Nov 21, 2015

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    Mini green plaid skirt black stockings black

    cut off shirt pink panties blue lace bra
    kelliTxxx kelliTxxx 36-40, T 2 Responses Jan 9

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    11-16-15The Queen text me

    and told me to wear purple today and clean her bathroom. She had bought me leggings and I hadn't an opportunity to wear them. It was a lil cold out and decided to try them. My choices in purple are limited except the outfit I had posted previously. Then I remembered she had a...
    stefiecdtv stefiecdtv 51-55, T 6 Responses Nov 17, 2015

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    9-25-15, I had to finish the hallway.

    I could only do it in halfs otherwise we wouldn't have been able to get through. First I needed the right outfit, short shorts have been working so well, I borrowed a pair of sexy ones from The Queen.Then I had to do the same steps as previous. Vacuum, scrub, shampoo. I forgot...
    stefiecdtv stefiecdtv 51-55, T 11 Responses Sep 25, 2015

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    This is what I put on this morning

    for the drive into work. New black A line skirt from Lane Bryant. New pink sweater from Macy's. I tried both on in the store and the SAs were very helpful.
    mat2Robin43 mat2Robin43 51-55, M 8 Responses Oct 29, 2015

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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 19 Responses Jul 10, 2015

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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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    mat2Robin43 mat2Robin43 51-55, M 10 Responses Jun 17, 2015

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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 66 Responses Jul 22, 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 11 Responses Sep 15, 2012

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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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    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 31-35, T 9 Responses Feb 21, 2015

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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 21 Responses Mar 1, 2015

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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...
    MirandaAlicia MirandaAlicia 36-40, T 6 Responses Jan 31, 2015

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    mat2Robin43 mat2Robin43 51-55, M 8 Responses Jun 13, 2015

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    Right now, it's a pair of black leggings,

    black satin bra with some fill, and a light purple workout top thing. This is the best dressing has felt in a long time. I came home and just had to find things to wear, besides the pantyhose and stockings I bought on the way. The feeling looking in the mirror was and is...
    CynthiaKarin CynthiaKarin 31-35, T 1 Response Dec 27, 2015

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    Nyssa59 Nyssa59 56-60, T 3 Responses Oct 1, 2015

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    This morning I put on my black lace panties

    and bra with thigh high stockings and some 3 inch heels. I put on a little black dress and went about doing housework for the morning. I even went outside to take out the trash and walked around my yard a bit. A couple cars looked as they passed by and I loved the feeling I had...
    JessicainNH JessicainNH 46-50, T 4 Responses Dec 28, 2015

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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, 2015

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    purple g string black thigh highs

    and red pumps. still wearing them now ;)
    stefanigurl stefanigurl 22-25 1 Response Dec 13, 2015

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    leggs4me leggs4me 51-55, T 12 Responses Oct 5, 2015

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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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    Chelseaax Chelseaax 22-25, T 5 Responses Nov 30, 2015

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