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I Have Worn Women's Shoes

for crossdressers who have done this 1,142 People

    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 30, 2015

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    if anyone wants to talk I'm 15 years old

    and I am a sissyboy I just love the feeling I secretly wear my sisters cloth she's 17 I like wearing panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans bras and I'm secretly attracted to masculine tough and hairy men ooh
    deleted deleted 26-30 Jan 9

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    Sure have. I find myself liking women's shoes

    more than men's if I am just doing casual things. Especially a pair of tight leather boots and pants, makes me feel very sexy. I buy them smaller than normal (8 womens usually, others 8.5) because I love super snug boots.
    Harukana Harukana 22-25, M Nov 22, 2015

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    No More Mens Shoes

    I started to wear female sneakers (keds) when my wife begged me to let her go to Las Vegas. Deal was she had to buy me a pair of keds. I have not looked back. Slowly I got rid of all of my mens shoes. I even have womens dress shoes that pass off as mens but if you look close...
    sneakerlover1 sneakerlover1 61-65, M 4 Responses Jul 9, 2013

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    I would rather where high heels ALL THE TIME

    than men's shoes. It just feels better to me om a shoeholic. I have way more heels than guy shoes and most of the women o know funny enough but not to me hehe
    whitwhit86 whitwhit86 26-30, M 3 Responses Jul 24, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 11, 2015

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    Making Friends at Payless.

    .. Don't be afraid guys..."TRY THEM ON" Those are the three magical words my favorite sales associate, Maribel told me in 2010, and they still ring true four and a half years later. To this day she remains a great friend. The sales associates at Payless will appreciate you...
    esthr009 esthr009 51-55, M 9 Responses Sep 15, 2014

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    Is it noticeable if you wear heels with jeans I

    usually wear cowboy boots so my jeans a a bit long
    Camocrossing Camocrossing 22-25, M 4 Responses Sep 3, 2015

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    Why does the garment industry hate women?

    Why haven't clothing and bra sizes been standardized. Shopping is a nightmare in the woman's department. Each brands size fits differently. I could be a five, 3 or 7 in jeans and dresses. Shirts are a little easier. I can just eyeball those. The reason I buy clothes every five...
    NotApplicable NotApplicable 22-25, F 3 Responses Jun 19, 2014

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    Hi I'm Jennifer. I'm a gay flamboyant sissyboy

    who isn't afraid to be herself. I am interested in meeting other fembois, gay men and genetic females for chat and ....well I haven't set a limit on where we could end up!!! Don't respond without a pic (pathetic) because I'll ban you from my world. MY Google+ link: https://plus...
    JenniferSissygirl JenniferSissygirl 26-30, T Oct 2, 2015

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    New Black Flats

    Last Friday I wanted to go out dressed. Decided to wear my new black flats from Lane Bryant. They had a neat silver buckle (non functional). After showering I stepped into a matching beige bra and beige panties. Then black tights and a black dress. Stepped into the shoes and...
    jml2000 jml2000 61-65, M 1 Response Sep 1, 2013

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    More often it is boots

    rather than shoes
    ib14fun ib14fun 46-50 8 Responses Aug 6, 2014

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    Shoes, Shoes, Shoes!

    Women's shoes are my favorite thing to wear.  Platform pumps, boots, round toe pumps, heels with ankle straps, clogs, mules, even ballet flats all are in my wardrobe!  Even like to wear lower heel boots in guy mode.
    denisegurl2 denisegurl2 46-50, T 3 Responses Feb 10, 2010

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    Like many who share this experience,

    I was fascinated by women's shoes as a child, and I went through the whole phase of trying on my Mom's shoes (both heels and flats) as well as other female relatives. As I grew older, my fascination grew more pronounced to the point that I finally bought my first pair of shoes...
    esthr009 esthr009 51-55, M 7 Responses Jan 27, 2014

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns skinny jeans heels and definetly make up and shoes and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 5, 2015

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    Mum gets me to wear her shoes to break them in

    when they are new just around the house
    deleted deleted 26-30 3 Responses Dec 17, 2014

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    Nursing Clogs

    I've written about the Body Shop before (no not that one) in my local area. I was shopping one day and found clearance nursing clogs that fit.  The shoes were in blue and lavender.  Well, I just had to have both pairs.Tried them on and they fit.  Great, sold!  Been wearing...
    jml2000 jml2000 61-65, M 3 Responses Aug 1, 2012

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    I Wear Ballet Flats

    First of all, I am not gay or a crossdresser, but I do have a love of women's flats, especially ballet flat with a very low or no heel. I wore my first pair of girls flats when I was 12. My parents bought a pair of patient leather flats for my younger sister whose feet were a...
    yeongju2010 yeongju2010 51-55, M 6 Responses Sep 22, 2012

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    Warning !!!!! Wearing Women's Shoes Can Be Addictive!

    This is a picture of my collection over 10 years ago and I have since purchased another 40 pair, I have so many now that it would take several hours to get them all out and get another picture, then put them back. I just recently purchased another 4 pair. 3 pairs of Ellie heels...
    jamie50 jamie50 51-55 9 Responses Dec 30, 2012

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    Ok so lets be honest here,

    I wear women's shoes everyday because I can and because I want to.
    TrannyHannah TrannyHannah 41-45, T 3 Responses Jan 19

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    My Closet Is Full Of Womens Shoes

    I am a 45 year old male who owns about 10 pairs of mens shoes and 200 pair of womens. I try not to buy mens shoes unless i have to for business. I wear womens casual shoes as much as possible. I have found many styles which I can wear as a male and get away with such as Asics...
    Deedeeteevee Deedeeteevee 41-45, T 7 Responses Jul 5, 2011

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    I Still Wear Them

    When I was young, my sister and I we were playing dress up, an I have to say that the game itself wasn't hurtful, actually it was in a way how I discovered that I was attracted to the patent leader, there is something about the shine of those shoes that I think is really cute...
    Car12345 Car12345 26-30, M 4 Responses Aug 18, 2012

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    So Many Shoes To Choose From

    I grew up with 2 older sisters and my mother. They dressed me since I was little and the shoes that were available as I got older-WOW. I got all the shoes my sisters no longer wore, flats, pumps, sandles, loafers and heels. Then I started to get my moms old heels which were...
    femboy4u femboy4u 22-25 4 Responses Apr 22, 2011

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    My mum came home from shopping with some new

    shoes and tried them on, she then passed them into myself saying you are size 5 walk around the house in these for a bit to break them in. Now mum can be a bit bad tempered so I put them on, they were just normal heeled shoes with a 3inch heel. She was right they did pinch and I...
    deleted deleted 26-30 3 Responses Aug 11, 2015

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    Wearing The Real Estate Agents Ballet Flats

    About 21 years ago my wife and I had decided it was time to move from the city into a more rural area. I was making good money in sales and it was time to leave our starter home and upgrade. We had decided on an area about an hour from the city where we lived and knew we could...
    jamie50 jamie50 51-55 2 Responses Nov 26, 2013

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    As a crossdresser myself I'm really interested

    on buying Women's Sandals made of Patent/PVC with heels in Black. As for Women's Shoes I usually wear a Size 11M. Yesterday I went to Kmart to look for Women's sandals and I found exactly what I wanted, but I'm thinking about buying that pair later. I was able to try on the...
    deleted deleted 26-30 3 Responses Apr 17, 2014

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    Please Help Ladies, I Need New Boots

    hello ladies, I have a problem, last month I went shopping for new boots. I felt that I was due a new pair. I walked en drab into Nine West and asked the SA for help, she had me try on several pairs of shoes and two pairs of boots. none fit that were comfortable enough for me so...
    lindad378 lindad378 51-55, T 6 Responses Jan 8, 2012

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I secretly am attracted to masculine tough and hairy men god I love heels
    deleted deleted 26-30 Jan 4

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    Wearing Women's Shoes Whenever I Can

    I have many pairs of women's shoes and boots. My wife only wants me to wear flats but she is slowly accepting me in boots and even some short heels. A few she has even approved for me with a 1" heels. I wish I could wear higher but so far my wife will not give in. Even my...
    cddude75 cddude75 51-55 7 Responses Jul 14, 2013

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    DonnaSt DonnaSt 66-70, M 5 Responses Jun 1, 2013

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    fercrox fercrox 46-50, M Apr 6, 2014

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    Longislandjones Longislandjones 26-30, M 3 Responses Nov 1, 2015

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    I have worn and own many pairs of woman's shoes.

    And have now lived in most continents and trust me the conversions are still annoying. Best not of advice is to try them on before u buy or buy them try them and return if the don't fit. (That's what I used to do when I was much younger). Now other than for work I'm always...
    SophieSeal SophieSeal 26-30, T 5 Responses Sep 2, 2014

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    top-bottom, 7$, 37$ and 45$ I need to stop

     but its too addicting :) 
    MelissaTheSexyCd MelissaTheSexyCd 18-21 1 Response Nov 13, 2015

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    Im starting crossdressing any old dress skirt

    wigs shoes will b a big help i can pay for post if u wish
    crossdresskatie crossdresskatie 22-25, M Dec 8, 2013

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    I have a large collection of women's open toe

    slippers. Love them and love driving in them
    Longislandjones Longislandjones 26-30, M 3 Responses Oct 29, 2015

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    I have a strong addiction to women's ballet

    flats. I can't stop buying them and wearing them. Most of the time I will just wear them around at home when I'm alone. I am starting to get more brave and wear them out in public. I just got some new Blowfish flats that I absolutely love. I'm going to wear them out shopping...
    FlatsFetish FlatsFetish 36-40, M 4 Responses Dec 4, 2015

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    New Shoes!

    Went out with my wife tonight. I was wearing women's jeans and a polo shirt. We walked into Cathy Jean which was having a big sale on summer shoes. I was surprised my wife didn't complain when I asked to try on a couple pairs. I tried on a pair with 3 inch heels which is much...
    cddude75 cddude75 51-55 3 Responses Aug 3, 2013

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    Payless

    is my favorite place to buy my heels because they always have my size (12 womens) and they are very friendly and helpfull to me. of course i always go en femme since i now live fulltime as a female and i wear my heels every single day, weather i am going out or not, they are just...
    Mizsuzy Mizsuzy 46-50, T 4 Responses Nov 29, 2011

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    I had a pair of shooties in the late 70's

    that I wore until the mid 90's when they fell apart. Great heels, just wore them out. 5 years ago I decided to see if I could find a pair of 2 inch booties that I could wear. Went to DSW and the first pair I tried fit, Bare Traps, got two more from Macy's. Shopping a very busy...
    bajep bajep 56-60, M 1 Response Jun 18, 2015

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    Anyone know a good place to buy women's size 12

    shoes besides payless and online?
    deleted deleted 26-30 6 Responses Jan 13

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    Lewis47 Lewis47 46-50, M 2 Responses Nov 15, 2014

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    Buys Ladies Tall Boots

    Last weekend i decided to go shoe shopping for some black tall ladies low heel boots. I went to Aldo shoes first because i know they do carry some ladies styles in size 11. Because it was Saturday there were 3 salesladies working and one lady customer in the store. As it was that...
    0hBrandie 0hBrandie 41-45, M 18 Responses Sep 24, 2011

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    I love, love, love high heels!

    I wear them as often as I can, which is usually just in the car on long commutes. I'd love to hear stories about your shoes!
    overhere951 overhere951 46-50, M 9 Responses Feb 27, 2015

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