I Want To Know What You Wore When You Crossdressed Last

Personal Stories, Advice, and Support 814 People

    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
    7 Responses Oct 29, 2014

    It's Sunday and I have a lot of chores to do

    around the house and outside which means jeans and tee shirt :( But that does not stop me from crossdressing, so I decided to do a Rago shapewear day. First a 511 panty in black, then my black 1294 OBG hiked up to under my boobs which is a lot higher than I normally wear it...
    CrossdresserLauren CrossdresserLauren
    46-50, T
    1 Response Feb 28

    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
    7 Responses Oct 29, 2015

    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
    16 Responses Mar 1, 2015

    I wore a black lace bra

    and panties set a grey sweater dress and black pantyhose
    holly39 holly39
    41-45, M
    Apr 10

    Need input from the brain trust out there.

    Attending a conference next week away from home. It's my chance to enjoy several evenings en-femme. I don't want to shave my legs( I know yuk! Unshaven legs, right?) but warm weather is here, and I hate not having tan legs when they're smooth during shorts weather. Have...
    deleted deleted
    26-30
    4 Responses Mar 20

    right now I'm wearing thong pantie with yoga

    pants sports bra with c cup breast forms and a tee shirt
    deleted deleted
    26-30
    Nov 21, 2015

    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
    2 Responses Dec 14, 2014

    Mini green plaid skirt black stockings black

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

    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

    I have the house ALL to myself

    until tomorrow. I'm plotting my experience, and would love a little input...
    deleted deleted
    26-30
    1 Response Dec 11, 2015

    Sometimes being Me is

    so liberating.
    MirandaAlicia MirandaAlicia
    36-40, T
    1 Response Feb 22

    im wearing my girlfriends clothes right

    now - black leggings and tights, black long sleeve tight turtleneck top...i love it
    mysoginist155 mysoginist155
    36-40, M
    1 Response Feb 26

    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 :)
    deleted deleted
    26-30
    7 Responses Feb 21, 2015

    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

    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.
    deleted deleted
    26-30
    3 Responses Dec 12, 2015

    purple g string black thigh highs

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

    3-15-16It's dressup day gurls,

    hmmm, trying to put together a cute outfit. What should I wear with these clothes?Red camisole, bra, garters and thong?Red corset and thong?Black or white thigh highs?Black or Red pumps?Most votes wins. I'll post pics later.
    stefiecdtv stefiecdtv
    51-55, T
    8 Responses Mar 15

    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

    I don't "crossdress"!

    I femulate I express in the feminine I wear clothing that suits my expressions Q: Why don't we say tomboys are crossdressers? A: Crossdressing is a derogatory word used to stigmatize feminine expressive boys.
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    6 Responses Apr 10

    I just got a new little skater dress.

    It's so cute! I'll post a pic soon.
    schoolgyrlKaren schoolgyrlKaren
    46-50
    4 Responses Dec 3, 2015
    Chelseaax Chelseaax
    26-30, T
    5 Responses Nov 30, 2015

    Black dress and sheer to waist pantyhose only

    need someone to share it with
    holly39 holly39
    41-45, M
    1 Response Apr 11

    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
    46-50
    Apr 14, 2015
    capeme capeme
    46-50, M
    2 Responses Feb 28

    As of right now, I am wearing black high heels

    w/peep toe, tan thigh high pantyhose, and a short, black dress. A large vibrator fills my behind and I am squeezing my tied up balls. That is what I wore last/am wearing now.
    lascruces1971 lascruces1971
    41-45, M
    3 Responses Oct 5, 2015

    Torn between choosing what to wear this evening,

    I plumped for the following:- Matching black bra and panties. Black 'body' with a crotch fastening. Fitted sweater. Dark red opaque tights. Red heels. Genuine wool, red pleated mini kilt. Do you approve?
    AnnaliseB AnnaliseB
    31-35, T
    6 Responses Mar 4

    ​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
    54 Responses Jul 22, 2014

    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

    This has been a Me-themed weekend,

    with the wife off on a weekend trip with her boyfriend. Even though I've been home watching the kids, they had school on Friday so I went out and bought more shoes than I've ever owned at one time as a male (bringing my total collection up to 11 different pairs for different...
    MirandaAlicia MirandaAlicia
    36-40, T
    2 Responses Mar 13

    Unfortunately I'm a little sick.

    I have so much coughing. I have to be covered. The legs do not feel the cold. I covered them with a pair of black stockings. It is always a good feeling.
    didone didone
    41-45, M
    4 Responses Feb 23

    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
    8 Responses Sep 25, 2015

    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
    9 Responses Sep 15, 2015

    ​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
    7 Responses Mar 20, 2015

    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
    Dec 27, 2015

    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
    10 Responses Oct 15, 2015

    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...
    deleted deleted
    26-30
    3 Responses Dec 28, 2015

    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
    14 Responses Oct 23, 2014
    mat2Robin43 mat2Robin43
    51-55, M
    5 Responses Apr 9

    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
    14 Responses Oct 24, 2014

    ​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
    16 Responses May 27, 2015

    I wore a purple waist trainer corset purple

    thong hold up stockings a lil black dress 5" heels
    liziemary liziemary
    36-40, T
    5 Responses Jun 4, 2015

    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

    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

    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
    3 Responses Oct 22, 2015

    Currently wearing my new plastic gingham sissy

    dress with matching panties, petticoat plastic underskirt, heels and my jingley sissy anklet. My mistress/wife took the photo :)
    capeme capeme
    46-50, M
    5 Responses Feb 28

    My wife went away for a few weeks to visit her

    sister. A dream come true for me. When I get in at night, I get out of all my male things and make myself comfortable. First a pair of black satin panties, then a black satin bra, of course black pantyhose are a must. Then to top it I slip into a semi-sheer pink nightgown...
    CrossdresserLauren CrossdresserLauren
    46-50, T
    2 Responses Feb 28
    capeme capeme
    46-50, M
    2 Responses Feb 21

    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

    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
    5 Responses Jan 31, 2015

    A risky' steampunk number

    that I made myself!
    Daniel2Danielle Daniel2Danielle
    26-30, T
    Mar 25

    Last time I dressed to the nines,

    I wore a faux suede crop top and a textured daisy print skirt, with a white bra and panty set, and some strappy 3" pumps. I straightened my hair, got dolled up with foundation, eyeliner, eyeshadow, lipstick, and mascara, and topped it off with some red nail polish :)
    alexphoenix alexphoenix
    22-25, T
    3 Responses Mar 4

    Daisy Dukes with suspenders,

    cowgirl boots, white bra and panties, tied up plaid shirt and bandanas round my neck, in my hair and round my wrist. Yee-haa cowgirl
    BDSMisintheblood BDSMisintheblood
    26-30, M
    1 Response Mar 4
    mat2Robin43 mat2Robin43
    51-55, M
    10 Responses Jun 17, 2015

    ​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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