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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 224 People

    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 4 Responses Nov 23, 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 6 Responses Mar 4, 2014

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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 4 Responses Dec 12, 2011

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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 6 Responses Apr 23, 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 5 Responses Jul 18, 2010

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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 16-17, M 4 Responses Mar 30, 2014

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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 2 Responses Mar 4, 2014

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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 2 Responses Aug 5, 2010

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    I went to fancy dress

    as this guy. https://www.youtube.com/watch?v=YQ643U7ccpMSeems The night was amazing. I strutted in, thankfully the hall was carpeted. I asked the first person inside the door "where's the birthday boy?" They pointed to 'Amy Winehouse over there. I turned and strutted through...
    Heellover Heellover 36-40, M Mar 15

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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 3 Responses Oct 30, 2011

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    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 3 Responses Sep 17, 2011

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    My friend let me borrow her high heels today

    and i came home when my mother saw me and me and then i told her to stay off and this is my life and i will not let u ruin it i want to be me you will not tell me who to be.
    Nick150 Nick150 13-15, M 4 Responses Nov 5, 2014

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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 2 Responses May 12, 2012

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    I had the day off so I decided I would put on

    my panty hose and geans and a top and my high heel boots with a strap that locks. I locked the locks and put the keys on my dresser. Well I drove to a city about two hours away and went to the mall did some Window shopping and just enjoying the sound of my heels on the tile. I...
    pmgurl pmgurl 51-55 7 Responses Sep 21, 2014

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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 May 9, 2012

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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 really love wearing high heel shoes with any of my outfits. I am tall and have shaved my long, tanned, and toned legs. I get great compliments from others on my appearance when...
    britishfemaleinusa britishfemaleinusa 41-45, F 7 Responses Mar 2

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    I love wearing High Heeled shoes,. It's viewed as a symbol of feminine frailty and makes me feel so feminine. I do wear sneakers and pumps etc, but when wearing a High Heeled shoe...
    KrisKrosSk8 KrisKrosSk8 22-25, F 6 Responses 1 day ago

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    So how many of you are looking forward to seeing the boots more in the closet and open toe heels being worn outside - especially in the north east.
    JessicaEvette JessicaEvette 22-25, F 23 Responses Mar 5

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    Makes me feel taller and shows off my legs and butt hahaha
    rubyroo15 rubyroo15 18-21, F 5 Responses Mar 1

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    New one and getting ready to go out....
    heel75 heel75 31-35, M 3 Responses Mar 6

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    Place the order for this online from MMC.  Will get in one week time....
    heel75 heel75 31-35, M 1 Response a week ago

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    by mom and it let to some great experiences and my eventual transition.
    Therealjason Therealjason 31-35, F Mar 16

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    I love wearing high heels, for me its just another part of expressing my femininity. Stepping out at night in my favourite evening dress with lovely 4 inch heels gives me such an...
    LISAMERCER LISAMERCER 51-55, T 1 Response Mar 21

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    I just bought my 5th pair of 4 inch heels in the past week. I just love my heels. Several years ago I made the discovery that my feet fit women's shoes much better and hen fit men...
    bajep bajep 56-60, M 1 Response Mar 16

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    I love to sleep wearing nothing but high heels.
    carsheelsandwomen carsheelsandwomen 36-40 1 Response Mar 18

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    I just love dressing in a corset with garters and stockings under my little dresses and high heels. Mistress enjoys seeing me go about my day dressed in in short babydolls and...
    Plugslave Plugslave 31-35 3 Responses Mar 1

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    I feel very dominant in my leather high heels today!!!! Wish there were a few guys laying down I could walk on, LOL!!!
    JennyTom JennyTom 36-40, F 11 Responses Mar 5

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    I am employed and I must dress up in a skirt and blouse, or dress, high heels and all the other things for my wardrobe attire of the day. I normally wear a 4 inch high heels when...
    olderfemalesunbathing olderfemalesunbathing 41-45, F 5 Responses Mar 14

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    When stopped at airport security I was wanded and set off the alarm so had to open my shirt and loosen my trouser belt. Still setting the alarm off I was asked to step into a side...
    SusanWST SusanWST 70+, M 6 Responses Mar 8

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    Just loving everything with high heels..boots, deccolete, mules but high heels sandals more than everything.
    Vralina Vralina 18-21, F 16 Responses Mar 10

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    My leather high heels for the day, indoors.
    JennyTom JennyTom 36-40, F 4 Responses Mar 12

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    I look at the platformed, seven inch high heels in store windows and practically feel my neck breaking, so I stick to a classic black heel that are soft leather and look chic. I...
    ladyPlum ladyPlum 26-30, F 7 Responses Mar 17

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    These aren't exactly high heels but they're wedges so close enough. I exchanged my other new ones for these, and I'm so obsessed with them :D
    Rosaalie Rosaalie 18-21, F 5 Responses Mar 17

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    I love high heels with nylon, I'm enjoying in this moment
    KayraCasanova KayraCasanova 46-50, M 3 Responses Mar 19

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    "I don't know who invented high heels, but all women owe him a lot!"-Marilyn Monroe
    AprilShowersMayFlowers88 AprilShowersMayFlowers88 22-25, F 5 Responses 2 days ago

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    I love high heels, I need to meet people in Orlando
    KayraCasanova KayraCasanova 46-50, M 3 Responses 1 day ago

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    Hi all! First post ever. After reading about all you guys I thought I'd join you.My high heel obsession started when I saw a few girls wearing them a few years ago. They just look...
    Junglist013 Junglist013 31-35, M 6 Responses Mar 11

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    There is something about high heel shoes that can't be quantified. The way they shape the foot and extend the calf. Wearing them lengthens the leg and appears to slim it down. When...
    luminesce luminesce 51-55, F 12 Responses Mar 11

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    Love wearing heels that can pump up my ***. Love wearing sandals as nude as possible:)
    Vralina Vralina 18-21, F 2 Responses Mar 14

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    This Friday I got myself a new pair, pretty cheap actually, walking in that specific store brought back memories , it's there that I also got the first ones a little over a year...
    Automx Automx 26-30, M 1 Response 1 day ago

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    If anyone wanted to view my brand new public gallery here's the link. After getting caught in my alternative wear at the beginning of the week, I've used this weekend to fill a lot...
    Junglist013 Junglist013 31-35, M 2 Responses Mar 15

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    The running in heels is not the interesting point. It is how I learned that is interesting. I was at a beach in Florida when I was younger and went into a shop that was decorated...
    Th3Nothing Th3Nothing 36-40, F Mar 6