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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 203 People

    In The K-mart Parking Lot!

    I was wearing a vanity fair 36C bra, underbra girdle with garters attached to some nude thigh high nylons, and a white lacy silk panty under mens jeans and a mens thick shirt. I had on mens sneakers and went into the local Kmart to do some lingerie shopping. I got a pretty...
    CandyKowal CandyKowal 46-50, T 2 Responses Sep 17, 2011

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    I don't think that u could actually call it

    caught if I do it on purpose. Several times I've driven to Macys, my favorite shoe store in my 4 inch pumps. So I park my car and walk in like I own the place. Most of the associates were very receptive of this, the ones that weren't I politely asked if they were jealous because...
    metalman9780 metalman9780 41-45, M 1 Response Mar 4

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    Wearing Heels In Public

    About 15 years ago, I decided to try something totally outrageous. I don't know what got into me, but I got this crazy idea and actually went through with it. I had recently bought a pair of clear platform mules with 8 inch heels. I've always loved clear heels and really liked...
    dondonna415 dondonna415 51-55, M 1 Response Oct 30, 2011

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    New Friend

    I was in my early 20's and dating this younger girl. She was a real tease and knew that I was into heels and shoes. But, she did not realize how much I was into it. One night after I dropped her off at home, I headed out for a quick slosh in the mud. I already had on my tight...
    wamclog wamclog 41-45 3 Responses Dec 12, 2011

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    I remember I went into a local Sears store to

    pay my credit card, walked in a pair of brown 5" heels, womens jeans, and a golf shirt. Went up to the cashier, paid my bill, looked around a bit, noting caught my eye so I left. As I walked out on the sidewalk in front of the store to step down into the roadway of the...
    krisyca krisyca 41-45, T 4 Responses Mar 4

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    Just When I Thought I Was Getting Away With It

    I'm a guy that wears high heels. I have been doing this for some 20 years, secretly. The last few years have seen me become more confident in wearing heels out doors. More and more I am realising that people generally don't notice, or aren't at all bothered. Recently, whilst...
    Heellover Heellover 36-40, M 3 Responses Nov 19, 2012

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    Few Times

    Think i got caught few times, but yesterday i pretty sure. I went "klicking" a hour long time in the city. I live not to far from the main street, so i decided to walk to the main street, then come back. But there was a lot of man, and i didn't want to risk, to meat some of my...
    VivienXX VivienXX 26-30, T 4 Responses Jul 18, 2010

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    Mother In Laws Boots

    i was caught by my wife wearing he moms boots she knew i dressed but freaked out
    louisetv louisetv 41-45 1 Response May 9, 2012

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    Caught In Cousins Heels

    When I was 14 yrs old I used to visit my aunt who lived in a rural town mostly on weekends.I used to stay overnight and on this one occasion my female cousin was gone for the weekend so my aunt let me stay in her room.My aunt had to go to the store so I was left alone in the...
    miata21 miata21 26-30 7 Responses Apr 23, 2012

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    Very Caught

    i drive a truck for a living and was traveling in El paso when i got stopped by the police. i was in a skirt and top with nylon's and heels on i was made to stand on the side of the road for 15 minutes while dressed this way
    spaz1177 spaz1177 46-50, T 3 Responses May 12, 2012

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    since i was 12 i liked wearing high heels

    because they make me feel as a girl but once i was in my bathroom and my mom was doing something in my room but i didnt notice and she heard the sound of the heels and later that day she asked me if i was wearing heels but i said no
    Girlyprincess1401 Girlyprincess1401 13-15, M 2 Responses Mar 30

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    I'm Sorry!

    It was my first pair of stillettos. I was in my teens and living at my parents in a small village. I had worn them around the house and loved them indoors, but I desperatly wanted to go out in them. I love the feeling of going somewhere in heels.  I waited...
    Heellover Heellover 36-40, M 9 Responses Dec 2, 2009

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    Kmart

    Once, about 20 or 30 years ago, I was in, I think it was a Kmart, trying on black pumps with 2 or 3 inch heels. A mother and her daughter, probably around 8 - 10 years old, came around the corner and saw me while I had one one and was putting the other one on. I was wearing...
    AndiSissy AndiSissy 51-55, M 1 Response Feb 24, 2011

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    Me Too! When I Was 5 Years Old.

    My first time in high heels was when I was about 5 years old. I would go into my parent's closet and try on the oversized shoes. I would always gravitate to my mother's 3-4"  heels. My mother loved it. She would giggle and tell me how fabulous I looked. From time to time...
    Josie06 Josie06 56-60, F 1 Response Aug 5, 2010

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    I Had No Choice...

    I was in college at the time, and had established a "normal" look wearing a Bass sandal (women's Sharon). It was the spring if my freshman year, and I needed a new pair, so I went to the bass outlet store. Of course, my staple sandal was in the women's section, and as I walked...
    rppshoes rppshoes 41-45 5 Responses Nov 23, 2011

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    Caught At K Mart

    It was a long time ago when I was in my 30;s. I had been wearing high heels a long time going out late at night and walking in places that I was reasonable safe. The urge to "kick it up a notch" had been in my mind for a long time. I was driving home one night about 9:00 wearing...
    10Camaro 10Camaro 66-70, M 6 Responses Oct 17, 2012

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    Related Experiences

    I have always liked wearing high heels even when I was a child. As I got older I was told I must not wear them, as they are for girls. I had to wear them secretly. After searching...
    hh4evry1 hh4evry1 36-40, M 4 Responses Jul 14

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    My wife and I were shopping and a lady walked by in short skirt and high heels my wife said she didn't know how they could wear heels all day. I said it wouldn't be that bad...
    pmgurl pmgurl 51-55 2 days ago

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    I love Christian Louboutin's shoes and boots. I have two pairs. Absolutely love wearing them.
    hh4evry1 hh4evry1 36-40, M 7 Responses 2 days ago

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    I like to be tall. I wear twenty centimetre heels! I am much taller then!
    Silfverberg Silfverberg 26-30, F 4 Responses Jun 29

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    I love dressing up, going casual, semi nude, or nude depending upon the occasion. When dressing I make sure I have a pair of high heel shoes to wear with any of my outfits.
    bustywifeinbikini bustywifeinbikini 41-45, F 1 Response 2 days ago

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    When ordering ladies shoes I post a review online stating I'm a male and wear ladies shoes.
    hh4evry1 hh4evry1 36-40, M 3 Responses Jul 14

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    I to love high heels. Especially platforms. Thanks to an understanding wife that realizes they are just a piece of footwear, has allowed me to to enjoy my heels. I am not at the...
    bnchmrk bnchmrk 46-50, M 1 Response 2 days ago

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    I absolutely love when a women with legs and a hot body that wears high heels. It just something about high heels that makes a women's sex appeal go up. I love the way it makes...
    HTAD HTAD 18-21, M 3 Responses Jun 25

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    I was caught by my Mom it was when I was about 8 we were having some friends over for a party. I snuck off and found my Mom's high heels and put them on and was admiring myself in...
    pmgurl pmgurl 51-55 3 Responses Jul 9

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    Love making love women just wearing sexy high heels
    hotty35 hotty35 31-35, M Jul 14

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    The first time i was caught crossdressing i wad 16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me...
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    During an orchestra concert, we were told to wear a black top and a black bottom but the teacher did not tell us whether or not we could wear tights so I wore a tight black Tshirt...
    conniejiang98 conniejiang98 16-17, F 1 Response Jun 28

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    Going strutting in my new high heels ☺️
    JessicaCD20 JessicaCD20 18-21, M 5 Responses Jul 1

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    Love my high heels. Feel so very sexy in them. Always get a thrill shopping for them.
    susiecdgurl susiecdgurl 56-60, T 3 Responses Jul 10

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    I am extremely into to my woman when she wears her skirts, stockings, and high heels. I find it very sexy and turns me on in the worst way to wear I have to ravish her and satisfy...
    cassiescowboy cassiescowboy 26-30, M 2 Responses Jul 13

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    I also love to wear high heels
    boytoy66 boytoy66 46-50, T 5 Responses Jul 14

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    I missed the mailman and needed a letter mailed. So I hopped into my car and drove to the post office. I was wearing a black bra with a oversized tank top and black shorts. It...
    meg1cdforyou meg1cdforyou 61-65, M 2 Responses Jul 13

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    During the times I was walking around naked, I was caught and almost caught being naked. Couple times I was outside being naked and my dad would come home from work and I was dash...
    thisguyrocks thisguyrocks 22-25, M 4 days ago

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    Swimming in HeelsYesterday while the wife was at work, I have been going through some of my oldest hiding spots of clothing and shoes and have been getting rid of the things that...
    jamie50 jamie50 51-55 2 Responses Jul 4

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    I own over 100 pairs of heels and Ballet Flats and recently decided to start going through some of them since a lot I have had since I wore a size 10. I now wear an 11 and wanted...
    jamie50 jamie50 51-55 1 Response Jun 25

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    I went out being the guy i am i was wearing my sexy black dress and heels when i was in a shop i saw my friend who noticed me i ran like hell and he followed i hid but he told my...
    conankoller conankoller 22-25, M 3 Responses Jul 13

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    I only wore em when my mom tried to go out (around 9th time in heels) and stumbled she said man its hard to walk in these things ... I was playing games so I didnt pay much...
    GinIyoku GinIyoku 26-30 1 Response 2 days ago

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    Nearly got caught today 😳. Walking around our local Brantano I spotted some delicious electric blue heels - I had to try them. Slipped off my shoe, popped the hot heel on and it...
    xAngiexx xAngiexx 41-45, M 4 Responses Jul 5

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    Ok... thanks everyone for participating in my opinion poll on which heels are your fav's (open toe or closed toe). Open toe was the fav with 41 votes, Closed toe 26 votes, and both...
    JessicaEvette JessicaEvette 22-25, F 15 Responses Jul 2

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    cannot get enough of my heels hihi love my white strappy sandals 2 1,2 inche heel cream white
    Highheels23 Highheels23 22-25, M 4 Responses Jun 28

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    Mowing the Grass in HeelsI had started mowing our yard Wednesday evening to get things ready for the 4th when several friends come over for the 4th and swim & BBQ. I had taken the...
    jamie50 jamie50 51-55 4 Responses Jul 4

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    Nothing better... Than to see a woman wearing a pair of black or red pumps underneath a pair of shapely long legs and some sexy stockings, never fails to catch my attention.
    BeardedDom BeardedDom 31-35, M 1 Response Jul 8

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    I find myself spending large amounts of time checking out all the amazing high heel designs and styles on the internet. I particularly like ALDO heels. They are often quite stylish...
    RobertaS RobertaS 36-40, F 10 Responses Jul 1

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    Yes I am male... and I walk in heels.I don't worry about what others think, and yes... I get weird looks sometimes; however I get more compliments from women who tell me they wish...
    WedgeHeelsRock WedgeHeelsRock 36-40, M 3 Responses Jun 27

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    I was 16 when she caught me wearing her panties and bra. I was in my room dressing up didn't know she came home and caught me she said you look cute let's go buy more
    LOVERPANTIES LOVERPANTIES 18-21, M 6 Responses 2 days ago

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    So glad I bought these today! Every girl out there knows how awesome it feels when you buy a new pair of shoes...my bad pair if heels! Some reason to get back to work now...
    atikin atikin 18-21, F 12 Responses Jun 28

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    Lily Allen wore gorgeous heels at Glastonbury last night, I would love a pair of these. The dress isn't bad either πŸ˜‰
    LisaTG LisaTG 26-30, T 4 Responses Jun 28

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    I love them so much. I buy them every chance I get. Nothing like coming home with a bag of new cute heels, I think lol.
    prettybella prettybella 22-25, F 13 Responses Jul 8