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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 207 People

    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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    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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    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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    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 3 Responses Mar 30

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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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    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 2 Responses Oct 30, 2011

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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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    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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    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 5 Responses Mar 4

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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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    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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    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 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

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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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    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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    Related Experiences

    Began wearing my boots at work. I'm in a job that's VERY anal about what men vs women wear. So far I've been complemented by the ladies at work and kinda weirded looks from the...
    shadowplt shadowplt 46-50, M 5 Responses Jul 28

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    I want to talk about heels any male female or trans feel free to add and message me
    Disturbedheels Disturbedheels 26-30, M 2 Responses Aug 9

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    Want to know what types of women's heels look good on a man in slacks and dress shirt. Don't want it too fem. just nice looking and no toes. Any ideas?
    shadowplt shadowplt 46-50, M 5 Responses Aug 13

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    Any one female make trans want to talk about heels message me or add me
    Disturbedheels Disturbedheels 26-30, M 2 Responses 18 hrs ago

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    I was 15 and had been wearing pantyhose regularly by that time. My wearing was usually limited to the 45 minutes I had home alone between getting home from school and when my...
    deleted deleted 26-30 1 Response Aug 5

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    I'm 28 and started out wearing high heels@ about nine every chance I could enjoy strutting in them
    whitwhit86 whitwhit86 26-30, M Jul 31

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    I find a girl wearing high heels such an absolute turn on
    Mustangkid2016 Mustangkid2016 22-25, M 4 Responses Aug 8

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    I love wearing high heels wherever I go and I don't understand why other girls look at me and say nasty things. Are they jealous or do they just think casual is the way forward...
    Abbierose93 Abbierose93 18-21, F 12 Responses 10 hrs ago

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    I was home alone my GF was gone for the weekend so I took the opportunity to dress. I went and got a sports bra and suntan panty hose I put on a nice dress and some high heels, a...
    pmgurl pmgurl 51-55 1 Response Aug 16

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    I'm straight, aged 37, and I have always loved high heels, ever since I can remember. Other than nylon ankle socks for some pairs, I don't cross-dress. It's just about the shoes...
    JayGovernor JayGovernor 36-40, M 5 Responses Aug 9

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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jul 31

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    I love wearing hose and high heels when I am dressed, semi dressed, or nude.
    tammylynne tammylynne 41-45, F 13 Responses Aug 10

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    This is about the embarrassing moment I had during this weekend, visiting my girlfriend at her parents' house. But a little background info first. I have been with my girlfriend...
    Nailpolishaddict Nailpolishaddict 26-30, M 3 Responses Aug 10

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    I love high heels, I wonder if it's because being a dancer I am use to being on my toes and feet arched. I love to clean in heels too, maybe I am just weird. I have a friend...
    Chicgeekgal Chicgeekgal 22-25, F 2 Responses Aug 18

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    Any women want to share some pics of mini skirt and high heels over 18 only please
    alexwarr123 alexwarr123 18-21, M 3 Responses Jul 28

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    My biggest question is why would you want where High Heels, its probably most redundant designed article, and many reaserch show it can easily destory your feet http://www...
    gypa gypa 26-30, M 1 Response Aug 7

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    This is such a turn on when a woman work's hard at work all day and her high heels are smelly and sweaty mmm
    Renayde92 Renayde92 22-25, M 22 hrs ago

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    Any one want to talk about high heels message me or add me
    Disturbedheels Disturbedheels 26-30, M 3 Responses 18 hrs ago

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    I geuss first it was the cutest little white cotton and lace nighty about mid thigh length well i wasnt actually wearing it at the time, I used to keep it in the back of one of my...
    sadei sadei 31-35, F Aug 16

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses 5 days ago

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    I was caught by my auntie in her swimsuit in the bath when I was 14 I thought she was at work allday so I found one of her onepiece swimsuits slipped it on and got in the bath I...
    markwet markwet 46-50, M 1 day ago

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    I went to work earlier and took over from a lady colleague. She was going to a wedding so I asked if she had a new outfit to wear. She had. It's a blues dress. I asked if she would...
    hh4evry1 hh4evry1 36-40, M 2 Responses Aug 16

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    High heeled commute to work. I sucked it up this morning. When I left the house to walk to the train station, I was wearing heels and long jeans. It's about 1/2 mile to the...
    Heellover Heellover 36-40, M 1 Response Aug 6

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    I was on a business trip out of town last week and had the chance to do a little shopping. I found a cute pair of Wedge Sandals at Target and purchased them. My flight home was...
    jamie50 jamie50 51-55 1 Response Aug 17

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    I swiped my first pair of panties from a friends sister when I was 9. By the time I was 11, I had collected quite a few pairs from her and my cousins. I kept them in a shoe box...
    Bobbie1952 Bobbie1952 61-65, M 4 Responses Aug 7

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    My best friend saw the bright blue thong I was wearing at his house... He told me to follow him inside we went to his mums room because nobody was home. He made me put on her blue...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 4 Responses Jul 27

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    Just in from the pub, left early so I could enjoy wearing some stockings etc. Girls, you don't know how good you have it?! Imagine being able to wear what you want with no...
    susspender susspender 41-45, M 3 Responses Aug 15

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    Not many people know I wear woman's underwear. I got caught in a thong by a sales assistant at ann summers. Yesterday I went into ann summers and seen a white thong with...
    nikolas444 nikolas444 18-21, M 2 Responses 2 days ago

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    The place to myself, basque, stockings & heels. What more can a guy want 💋👠
    susspender susspender 41-45, M 12 hrs ago

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    I have always wanted to get caught cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night...
    Robertredlips Robertredlips 56-60, M 3 hrs ago

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    I was pantsed by a guy half the size of my big muscular, **** diesel self, while I was wearing very tacky, leopard print bikinis. He knew he had no shot of winning any fight w...
    Relent34 Relent34 26-30, M Aug 6

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    This is a famous joke. Not true, but fun to repeat. Sam walked into the locker room to change into his softball uniform. The guys spotted the bra he was wearing and shouted "What...
    Robertredlips Robertredlips 56-60, M 4 days ago

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