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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 231 People

    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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    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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    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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    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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    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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    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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    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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    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.
    IwantoCrossdress IwantoCrossdress 13-15, M 4 Responses Nov 5, 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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    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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    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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    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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    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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    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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    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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    Related Experiences

    Being a busy wife and mom, I love dressing up and going out. When I am dressed up, I will always include wearing one of my many pairs of high heels with a pair of hose. I believe...
    oldermaturewife oldermaturewife 46-50, F 8 Responses May 6

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    As I am writing this I'm wearing my sisters high heeled boots and I love them! I don't know why but I really enjoy wearing high heels. They just make me feel like a women.
    TerminatorV1 TerminatorV1 18-21, T 3 Responses 3 days ago

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    ​I love wearing high heels so much, I have an entire collection. And how do you think they look on me?
    sonaydushi sonaydushi 18-21, F 9 Responses May 5

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    Hey, we needed another story up here. So I was caught wearing pantyhose. Now first off I do love to wear them. If I lived in a colder climate I would wear them all winter long as...
    cdLisas cdLisas 56-60, T 3 Responses May 22

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    Only 7 months ago I started wearing my high heels out into public. I have been wearing my boots etc for many years behind closed doors. Since I wore my boots out for the first...
    blindfoldstacy blindfoldstacy 41-45, T 1 Response 6 days ago

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    I grew up loving gymnastics tumbling and so full of energy, little did I know that I was never going to get much taller. I moved to cheer and then dance but seems that I topped out...
    ChloeGenovar ChloeGenovar 22-25, F 16 Responses May 15

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    I'm 5'9 standing barefoot.. But I feel confident in the highest heels! A lot of men hate tall women but I don't care. I do it for me. :)
    Mseducated18 Mseducated18 18-21, F 7 Responses May 15

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    Hi everybody, hope all you agree with me how difficult to hide feminism being male. This is a real incident how I was caught unaware by my wife with my anklets on. After my...
    gm2707 gm2707 22-25, M 5 Responses 5 days ago

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    I still remember wearing my mother heels as a little girl, clomping around and wishing I were big and imagining myself being soooo pretty. And how excited I was when I turned 13...
    bunnigirl bunnigirl 46-50, F 4 Responses May 18

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    It feels good wearing heels, it adds to a woman's confidence. There's a kind of sexiness you feel when you're in heels.
    lemongrass09 lemongrass09 46-50, F 8 Responses May 15

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    I love heels also I have spent the last two days wearing a pair of 4 1/2 heels doing work around the house
    jerbare jerbare 61-65, M 1 Response May 15

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    I see some heels calling me!
    Living2Heights Living2Heights 16-17, F May 7

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    My new wedge heels
    heel75 heel75 31-35, M 9 Responses May 14

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    I've always loved heels and I know my legs look better in them. I need to buy more shoes, I've been getting boring over recent years
    jayneclare jayneclare 41-45, F 6 Responses May 15

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    Always a girl thing. I like wearing wedge shoes and sandals ❤️
    lemongrass09 lemongrass09 46-50, F 23 Responses May 14

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    It was a funny story I was young and my friends dared me to put on my aunts underwear and my mom and aunt caught me
    stillwetsbed stillwetsbed 22-25, M 3 Responses May 22

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    Judge me by the colors of my sandals.
    lemongrass09 lemongrass09 46-50, F 10 Responses May 14

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    Some more pics
    heel75 heel75 31-35, M 4 Responses May 15

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    I opted to wear this open sandals in going to the parlor for nail cleaning and foot spa. I love my pamper time...
    lemongrass09 lemongrass09 46-50, F 9 Responses May 17

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    I'd be very surprised if I found my partner wearing high heels. The first thought would be :"Are those my shoes?!". I'd double check looking at them. Once I found out they weren't...
    1unusualLass 1unusualLass 31-35, F 6 Responses 4 days ago

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    I recently bought a pair of (4 inch) high heels, just because I wanted to know what it was like to walk in them. And if it is really so difficult. Well turns out it's not really...
    Sikarno Sikarno 31-35, M 5 Responses 4 days ago

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    I love wearing leather high heels!!!!!:)
    JennyTom JennyTom 36-40, F 1 Response May 20

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    Was caught by boyfriends girl friend wearing bra with tanktop panties (thong) and thigh high socks.
    Zap4you Zap4you 46-50, M 2 Responses May 22

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    A few years ago I was chatting on IM with a male friend I'd met online. It was early in the morning and I'd just gotten out of the shower and put on my Victoria's Secret cotton...
    secretdesires78 secretdesires78 36-40, F 8 Responses May 21

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    I'm a big guy. Not fat but big. I'm 6'6" 240lbs. One night last summer, I was driving through the mountains of NH. It was a gorgeous night. It was warm with a clear sky and no...
    toytaco05 toytaco05 31-35, M 2 Responses 6 days ago

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       Just got these two new heels for work the Charles wedges and these Bamboo T-straps sandals. 
    bajep bajep 56-60, M May 17

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    This is my "******** heels" as my daughter calls them. I generally don't wear them except to one of the topless clubs with my guy or in the bedroom. Reason being, they aren't very...
    zanyzoey zanyzoey 36-40, F 21 Responses 3 days ago

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    I got caught today at the urinal at the grocery store. My shorts had slipped down as I was peeing, and another guy walked in. He stood behind me for a few seconds, then went to the...
    Ninjaburgerq Ninjaburgerq 36-40, M 4 Responses May 7