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I Have Worn Women's Shoes

for crossdressers who have done this 1,004 People

    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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    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 56-60, M 1 Response Sep 1, 2013

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    fercrox fercrox 46-50, M Apr 6, 2014

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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 8 Responses Sep 15, 2014

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    I finally made a big step no pun intended

    but I went out in my flats for the first time ever it was only for 5 minutes or so but I did it next will be around the block
    AllanJ86 AllanJ86 26-30, M 11 Responses Dec 3, 2014

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    A Very Old Story Of Outlet Mall Shopping

    This is a story of an experience I had almost 15 years ago wearing women's flats... I had the day off so I decided to do a little "gender-bending" at an outlet mall about two hours away. To begin I had to dress as a shopper... White turtle neck, women's jeans, Hanes soft-touch...
    BrennK BrennK 41-45, M 2 Responses Dec 30, 2012

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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 4 Responses Sep 2, 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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    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 56-60, M 3 Responses Aug 1, 2012

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    DonnaSt DonnaSt 66-70, M 4 Responses Jun 1, 2013

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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 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 5 Responses Jul 5, 2011

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

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    AllanJ86 AllanJ86 26-30, M 1 Response Oct 1, 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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    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 3 Responses Aug 18, 2012

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    A Small History About Me And My Love For Wearing Heels And "Womens Shoes".

    For as long as I've been able to walk, I have ALWAYS loved wearing high heels. The look, the style, the feeling, it is something that I have always been loving to do. My story starts way back then, since I was able to walk, way back in the very early 1990s. I always found...
    converselover110 converselover110 26-30 2 Responses Mar 2, 2013

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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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    Men Who Love Womens Shoes.

    Here is an article explaining why men like to wear womens shoes. Let me know what you think. http://wizzley.com/men-who-love-womens-shoes/#comments
    FlatsFetish FlatsFetish 36-40, M 5 Responses Oct 21, 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 7 Responses Dec 30, 2012

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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 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 Jun 18

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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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    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 3 Responses Jul 9, 2013

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    Shoe Story

    I love wearing women's shoes when I can. One time around Halloween, I decided to use holiday to my advantage. I went into a shoe store wearing blue thigh high stockings underneath my jeans and sneakers. I was very scared and almost left the store. Then the lady in the store...
    deleted deleted 26-30 Mar 12, 2012

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    Shopping

    I wore a pair of plain black lace-up ankle boots with a 2 inch heel and 10 denier hold-up stockings under my jeans whilst doing my weekly supermarket shop.  I was in the place an hour and walked up and down every aisle.  I dont know how, but ...
    teather teather 46-50 2 Responses Feb 22, 2010

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    Size

    Crossdressing found a nice sexy pair of heels but hard to get my size n dnt wana go in shop to buy womens shoes n clothes ect ne help plz xx
    crossdresskatie crossdresskatie 22-25, M 4 Responses Aug 11, 2013

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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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    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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    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 41-45, M 8 Responses Feb 27

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    AllanJ86 AllanJ86 26-30, M 1 Response Sep 4, 2014

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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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    I Love Heels But...

    hii I am a 15 year old gay male and I love to crossdress, I like to wear all types of shoes like girls converse, boots, ballet flats, ankle boots etc however I also love to wear heels because they are one of the most feminine pieces of clothing and I love feeling girly. But the...
    Geohow Geohow 13-15, M 1 Response May 17, 2013

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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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    Mum gets me to wear her shoes to break them in

    when they are new just around the house
    deleted deleted 26-30 4 Responses Dec 17, 2014

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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 2 Responses Aug 3, 2013

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    Every Day!

    Thank you DSW, Rack Room Shoes and Payless!So many shoes and so many I like.And the sales seem to happen at just the right time.Flats, chunky heels and spike heels ... each have their place.Oh, yes! It is women's shoes each and every day for me.The latest for work, business...
    Josie06 Josie06 56-60, F 1 Response Jul 8, 2012

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    More often it is boots

    rather than shoes
    ib14fun ib14fun 41-45 6 Responses Aug 6, 2014

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    For about two and a half years now, since the start of 2013 or earlier. It really deterred me from any activity on my feet when it wasn't necessary. (I use to be able to take 4...
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    I love it when women wear skirts and dresses. The flow of the fabric teases and tantalizes. However much skin is showing just hints powerfully at the skin that isn't. Elegance...
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    I like watching a women's body reaction when I please them orally