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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 229 People

    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    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 26-30, F 6 Responses Mar 27

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    I bought these boots thinking i was going to offer them to my girlfriend . I got the biggest size they had in the store.So once i got home i had to try them on.....hands trembling...
    bootlove2 bootlove2 51-55, M 3 Responses Apr 11

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    Place the order for this online from MMC.  Will get in one week time....
    heel75 heel75 31-35, M 2 Responses Mar 22

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    The perfect shoes for a woman. The legs abd feet can become a great weapon of seduction because they are so sexy! I hate when they hurts, but it's to price to pay!
    Vralina Vralina 18-21, F 11 Responses 1 day ago

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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 love to wear high heels where ever I am regardless of what I am doing. At home, you will catch me wearing a pair of high heels regardless of what I am wearing or not wearing.
    singleredheadfemale singleredheadfemale 41-45, F 5 Responses Apr 10

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    Help me out here. I love wearing my heeled boots especially in public. I usually wear them under my jeans or if I'm in a private place with my skirt. How do I realize a dream of...
    shadowplt shadowplt 51-55, M 5 Responses 1 day ago

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    I love it when my wife sends me to the store wearing my heels. The sound of them clicking as I walk through the store seems so loud and I feel like everyone is looking at me. I...
    slavemissylee slavemissylee 56-60, M 2 Responses Mar 31

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    Getting some kinky new high heels soon to replace old ones which are too small for me now, so excited to slip my feet in them and lock them in tight.
    Heels4reals Heels4reals 18-21, M 1 Response Apr 7

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    As I get older, I realize they are ridiculously painful. Doesn't matter how good they look, I have no desire for blistered swollen feet. I don't need high heels to look feminine...
    ajrestless ajrestless 22-25, F 3 days ago

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    I love high my high heels and now they sit on a shelf untouched like they're in a Heel Museum for the once devoted twice demoted wearer all because I sustained a back injury 4...
    Quasimodo1987 Quasimodo1987 26-30, F 3 Responses 3 days ago

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    I got a pair of clip on 4.5 inch chandelier earrings in the mail today. I tried them on. Before I knew it, I was standing in the mirror, applying a dark coat of lipstick. I was...
    jessicavamp jessicavamp 41-45, M 2 Responses 3 days ago

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    I actually don't. I have an irrational hatred towards high heels. I find high heels really stupid.
    BrokenInnocence BrokenInnocence 13-15, F 3 Responses 1 day ago

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    I to love to dress as a woman and wear high heels with a 7 inch high heel and makeup and go out in public
    wissers wissers 66-70 2 Responses 4 days ago

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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 7 Responses Mar 26

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    I love high heels, I need to meet people in Orlando
    KayraCasanova KayraCasanova 46-50, M 4 Responses Mar 28

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    Definitely a benefit of working for a company with lots of professional women that enjoy dressing this way. Love seeing a woman in high heels, and a skirt. Showing off your calves...
    Kman4You Kman4You 36-40, M Apr 4

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    I to love to dress like a female away from work in a short pencil skirt sexy blouse high heels with a 7 inch heel full makeup and ecrtto me this is a real thrillfor me
    wissers wissers 66-70 4 days ago

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    Hubby brought me home some nice new leather high heels, I LOVE THEM!!!!
    JennyTom JennyTom 36-40, F 5 Responses 2 days ago

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    I was just wearing my kaftan this morning before I got dressed. I decided to paint my nails purple for fun. I had just finished painting them and was cleaning up the kitchen when...
    Sharon03 Sharon03 61-65 9 Responses a week ago

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    I was 5 years old when my Mom caught me wearing her red lipstick, and posing in the mirror with a cigarette. She didnt freak out. She just wiped my mouth and told me I was very...
    sillytilly2012 sillytilly2012 51-55, T 3 Responses Apr 8

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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 3 Responses Mar 28

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    Well here's what happen today I'm 16 in high school and I was wearing pink polka dot thong and spandex over and red sports bra and over my guy cloths so I went to school and went...
    AZCROSSDRESSER AZCROSSDRESSER 18-21, M 5 Responses Mar 29

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    I went out last week and did some banking wearing a pair of 6" platform heels. The trip included stopping at 2 banks, lowes, and a supermart I was wearing a pair of longer jeans...
    jerbare jerbare 56-60, M 2 Responses 20 hrs ago

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    this happend last year i was out and about at night time in my cream heels about 2/12 inche to 3 inche high open toe whit ankle strap heels just walking around listening to the...
    HighHeels24 HighHeels24 22-25, M 2 Responses Mar 24

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    nothing like a women that has some sexy *** feet in heels and wearing nothing but those in the bed.... IT JUST BRINGS THE FREAK NASTY OUT IF ME!!!
    Hypnobud Hypnobud 26-30, M Mar 26

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