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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 212 People

    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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    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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    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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    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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    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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    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 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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    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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    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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    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 3 Responses Mar 30

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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 May 9, 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 2 Responses 2 days ago

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    Related Experiences

    I love wearing my nice silver shiny high heels. I'm 4'10" n my shoe size is 5. I look so chic in them. They almost look like the Disco shoe from the 1970s. Disco Rules!
    DiscoNight1970s DiscoNight1970s 46-50, F 9 Responses Sep 4

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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 Aug 26

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    Here are my new heels I love them
    Disturbedheels Disturbedheels 26-30, M 2 Responses Sep 10

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    My full collection feel free to add or message me
    Disturbedheels Disturbedheels 26-30, M Sep 3

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    They're just sooooooo pretty
    jaquelynlupi123 jaquelynlupi123 13-15, F 2 Responses Sep 3

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    I am a male who loves wearing high heels but not confident enough to wear in public :-( I probably have a bigger collection of high heels than some of you females ;-)x
    MaleInHighHeels MaleInHighHeels 36-40 5 Responses 6 days ago

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    I love wearing high heels with my short dresses or a skirts and a blouses. I also wear them when wearing other outfits as well as in lingerie.
    momandher2girls momandher2girls 36-40, F 10 Responses Sep 15

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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 13 Responses Aug 26

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    I love wearing high heels when I am dressed, semi dressed, or nude. I love showing off my very long legs.
    nudistwifeandmother nudistwifeandmother 41-45, F 1 Response 4 days ago

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    I was caught by my mum a few months ago. I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around...
    tomcd95 tomcd95 18-21 7 Responses Aug 29

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    My public service rant for all my sisters out there: I like high heels. They are beautiful. But some women, including me, should NEVER wear heels! Geeze. Some of you walk like...
    Deedle623 Deedle623 51-55, F 6 Responses Sep 4

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    When I was 14 I started crossdressing. My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties...
    Stephaniegirl226 Stephaniegirl226 36-40, M 6 Responses Sep 13

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    I was caught cross-dressing. I sometimes travel to different cities for work. In nice cities (San Francisco) I rent a motorcycle on my days off and ride to the nice places. In SF...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    My friend - her name is Kaila, just took 5 new professional pictures of my feet in high heels and I'm so excited to share them with you! After school I met her at her mom's photo...
    bluetoesonly bluetoesonly 18-21, F 2 Responses Sep 12

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    Hello I am a very nice man that likes to see women in high heels. Over the years I have bought and given away over 150 to 200 pairs of high heels to women that I meet or know...
    SilkPantyhose SilkPantyhose 56-60, M Sep 11

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    idk if u find this odd, but i began to love men in high heels after i seen Prince in them.... he so dang handsome and the heels added to his sex appeal.... 😊
    aijmeerah aijmeerah 16-17, F 2 Responses Sep 4

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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 Aug 26

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    Any one want to talk about high heels message me or add me
    Disturbedheels Disturbedheels 26-30, M 4 Responses Aug 26

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    i love everything about high heels, even the sound they make when i walk in them, i feel sexy when i wear them!! hehe
    mistressDonna mistressDonna 26-30, F 4 Responses Aug 31

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    I like short girls in high heels. I'm 5"7 but I like toss-able girls
    Alylovespuppies Alylovespuppies 16-17, F Sep 9

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    There is nothing sexier then seeing a woman in nothing but high heels and stockings.
    lonewolf2060 lonewolf2060 51-55, M a week ago

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    I am professionally employed outside my home. My work attire includes skirts and blouses, dresses, and of course my high heels. I never wear pants to work. I love to show off my...
    momwithsons momwithsons 36-40, F 6 Responses 2 days ago

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    I love high heels but I'm too tall to wear them. 5'7 ..
    dropdeadwilma dropdeadwilma 16-17, F 12 Responses 2 days ago

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    I thought that I was alone in the building and decided it was a good time to try on some new knee boots with a black bra, cami, panties, and nylons. I had accidentally trigger the...
    JessicaDale JessicaDale 51-55, T 1 Response Sep 13

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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 Aug 25

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    In the middle of the summer I was caught naked out side enbarising and funny. My uncials house has outdoor showers .my aunt told me and my friend jack to get in the showers and...
    jst135 jst135 13-15, M Sep 5

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    I have been wearing my boots with 3 inch heels as of late every day I have had no comments made but have had some second looks
    jamie172 jamie172 46-50, T 2 Responses 4 days ago

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    I'm a very fat girl and I love wearing heels. Usually 3-4 inches since I am already 5'10. The last time I ran was to get from the reception area towards the hotel. Ran through...
    FattyAndLovingMyself FattyAndLovingMyself 26-30, F 3 Responses 6 days ago

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    I went out to the mailbox today wearing my new 4" mary janes. Usually I am pretty discrete, but today I missed and as I was nearing the end of the driveway a woman drove buy and...
    tvCorinne tvCorinne 51-55, T 5 Responses 6 days ago

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    I love wearing women's shoes in general, but I think men should be able to wear wedge heels freely. In my humble option, I don't think stilettos suit men. By the way, I've lost...
    Wedgeslave Wedgeslave 41-45, M 1 Response Sep 4

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    Last night I was wearing my sisters clothes I had on her blue bra with matching getting on silky pantyhose black mini skirt pink crop top and 5 icnh pink heels on and I went to the...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 2 Responses Aug 31

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    i went downstairs to go outside to smoke,i thought my aunt was asleep in her room.im out smoking when i see the front room light come on.i start to get real nervous,then the front...
    SISSYGUYMARIGAIL SISSYGUYMARIGAIL 46-50, M 6 Responses Sep 9

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    Heels. Heels heels. Why do so many men find heels so much of a turn on. I just met up with some one that all he wanted to do when we got to the bed room was kiss and lick my heels...
    Smarty123xxx Smarty123xxx 26-30, F 10 Responses 4 days ago

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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...