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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 232 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    The last time I was "caught" my neighbor lady who is in her 70's caught a glimpse of my pumps under my jeans while i was walking to the garage. A couple days later she asked if I...
    Brin41 Brin41 46-50, M 4 Responses 1 hr ago

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    I was caught by my wife one morning, the kids spent the night at grandmas house and I had the day off. The wife left for work in the morning, I got up right away after she left...
    Brin41 Brin41 46-50, M 2 Responses 2 hrs ago

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    i was hanging with a friend and i was wearing my favorite high rise pink thong and he just laughed at me and then firced me to do stuff for him after his mom gave my the clothes...
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 3 hrs ago

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    Tonight I took my usual evening walk on the city trail system. I've said this many times before, no make-up, wigs, breast forms or anything female above the waist. I was stopped by...
    shadowplt shadowplt 51-55, M 3 Responses 3 days ago

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    It is such a pain to find nice heels in my size, I am a size 10.5 mens, so you can imagine the hassle that I am going through.
    Tonyanal Tonyanal 41-45, M 3 Responses 3 days ago

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    i was caught by the paper lady. i don't know her personally. she must have told her husband. he slowed down every time he was on the route after that.i have been a little more...
    sbjj sbjj 51-55, T 3 Responses 3 days ago

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    But I cant walk in them!! My mum bought me these heels to wear to a wedding but I dont know how I'll last a day in them! Any girls here have any tips on walking in these and not...
    amyp98 amyp98 16-17, F 1 Response 3 days ago

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    Those 4" were a bit too high to start but still i loved everything about it. The way my *** is lifted a bit , the hipswing , the sound they make... Everything is about getting all...
    Hlstg Hlstg 26-30, M 5 Responses 5 days ago

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    This evening I went to my local convince store to get a soda, I usually wear my heeled boots and jeans when running errands. The store clerk, a nice young lady, asked me "Can I ask...
    shadowplt shadowplt 51-55, M 2 Responses 5 days ago

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    What is it about girls in heels?? Obviously its best with a short dress/skirt on, but even with jeans, so, damn sexy!
    MrMeAndYou MrMeAndYou 31-35, M 5 days ago

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    I love to wear a short dress with high heels.
    TheSubmissiveX TheSubmissiveX 22-25, F 19 Responses 6 days ago

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    When going to work and other places, I love to dress up in a short dress or skirt and blouse. With my wardrobe ensemble, I wear hose and my high heels. Being a tall woman, I...
    femalemusiclover femalemusiclover 46-50, F 3 Responses 6 days ago

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    As the new work week started, it was time to put Kimberly away for a few hours. As I got up, I looked in the mirror, barely recognizing my male face, I decided to do something...
    crosskimmy crosskimmy 26-30 4 Responses a week ago

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    love to see woman in heels
    tommygun522 tommygun522 51-55, M 2 Responses a week ago

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    high heels and cfm boots,what a turnon for me,such a wonder to behold
    waxfootback waxfootback 46-50, M Jun 24

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    Attempt in 5 inch heels with saree...
    heel75 heel75 31-35, M 2 Responses Jun 24

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    Attempt in 5 inch heels with saree... 
    heel75 heel75 31-35, M 1 Response Jun 24

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    I must have about 40 pair of highhels I cant help it whenever I have the time and the money I just have to get a pair or two of heels ,I mostly get mine from thift stores mainly...
    highonheels45 highonheels45 41-45, M Jun 24

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    I want high heels so badly they are so good looking :)
    IwantoCrossdress IwantoCrossdress 13-15, M 1 Response Jun 22

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    Today's high heel pic. Enjoy
    vegasdoc vegasdoc 51-55, M Jun 21

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    I enjoy wearing high heels at home and when out in public. I have about 50 pairs of heels to wear. Some of my heels are 4 and others are 5 inches in length.
    matureblondefemale matureblondefemale 41-45, F 10 Responses Jun 18

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    I need help on what to wear give me some suggestions girls
    deleted deleted 26-30 Jun 18

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    I am a heels lover. I could run in heels but wouldn't know how to walk in flat shoes! Heels are the only type of shoes I got at home and non of them are below 4 inches!
    Wynee Wynee 36-40, F 10 Responses Jun 17

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    I brought a really nice pair of heeled brogues fairly recently, and I must say I want to wear them pretty frequently. Yeah, I am a straight guy who loves to experiment and wear...
    liveinlondon liveinlondon 36-40, M 3 Responses Jun 17

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    i used to wear heels but today i wore leggings for the first time. i will nver forget this feeling
    deleted deleted 26-30 Jun 17

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    Sitting in my usual spot in the park. Love when a lady strolls by in heels. Todays heels I saw were simple yet sexy. A tall blonde lady with slacks on. She had about 2 inch peep...
    highheelsrule highheelsrule 18-21, M Jun 16

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    My favorite high heels have peep toe, 4-5 inch heels, w/sling back. I wear heels in a variety of colors, materials, and accents. Often in the privacy of my house, I wear high...
    lascruces1971 lascruces1971 41-45, M 4 Responses Jun 16

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    Tomorrows heels are waiting for me on the bedroom floor:)
    JennyTom JennyTom 36-40, F 2 Responses Jun 15

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    The toes on my heels look sharp, but Tom says they don't hurt at all the leather is so soft:)
    JennyTom JennyTom 36-40, F 1 Response Jun 15