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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 234 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 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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    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 6 Responses Mar 30, 2014

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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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    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 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 1 Response Mar 15

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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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    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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    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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    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.
    deleted deleted 26-30 4 Responses Nov 5, 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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    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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    Related Experiences

    Having been cross dressing since I was 6, high heels have always been a staple of my female projection. Even when it was my childish feet in adult heels, I had to have them. How...
    cdsubalice cdsubalice 56-60, M 1 Response 1 day ago

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    Its rare but I do, Sometimes outfit calls for heels. I learned to walk and be comfy in them in the mid 90s.
    Averageguy41011 Averageguy41011 41-45, M 1 day ago

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    Story two, after work i ussualy stop at a place i know and switch from me to Serenity. And because it was a cloudy mild little bit of rain i know that no one was going to be...
    Puddles420 Puddles420 22-25, T 1 Response 1 day ago

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    I new to hear but here is a kind of caught story, i ussualy drive back from work when im alone en femme and its roughly a 9 hour drive so when I do drive alone im dressed...
    Puddles420 Puddles420 22-25, T 1 Response 1 day ago

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    I have been wearing pantyhose for many years. I started in my teens. At home, under my clothes, or fully dressed up in high heels, panties, bra, and short dresses, I enjoy how...
    lascruces1971 lascruces1971 41-45, M 1 Response 2 days ago

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    I enjoy wearing heels and the way they force me to walk femininely. I enjoy the way they make me stand and the way they shape my legs and buns and help to slenderise my figure. I...
    amandatrane1 amandatrane1 51-55, T 3 days ago

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    When I wore my first pair of heels I was ecstatic. My mother gave me a black pair of five inch ankle straps she had because we both took the same size shoe. I was in my early teens...
    Teamouse Teamouse 26-30, F 5 Responses 4 days ago

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    I recently ordered my 14th pair of high heels wedges from Torrid. I submitted a product review that was approved and posted. Now there is a pic of my feet n the Caged Black...
    serinalynn serinalynn 66-70, M 5 days ago

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    I once saw a gorgeous young lady who wore beautiful stiletto boots, strutting home with supermarket bags dangling from her arm. Walking along I noticed she placed each foot...
    Teamouse Teamouse 26-30, F 2 Responses 5 days ago

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    Didn't used to when I was younger but wore these out yesterday and I think I'm finally starting to figure it out!
    amyp98 amyp98 13-15, F 4 Responses 6 days ago

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    Anyone that wants to chat about heels with me. Please let me know! I love heels very much.
    highheelsrule highheelsrule 18-21, M 1 Response 6 days ago

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    Who doesn't ? I am a man, but my wife is a petite only 5ft15. So she looks so much better in heels, her booty is more pronounced and her chest points out when wearing high heels...
    Luckyguy1970 Luckyguy1970 41-45, M 1 Response a week ago

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    So hot and make you walk in a walk thats hot and so many variations of them too and Im a guy and i have one pair and i love them but i wish someone could help me get more pairs...
    Iwantocrossdress Iwantocrossdress 13-15, M a week ago

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    I love my high hills and stocking I feel so sexy when I'm wearing new stocking my hills ar 4in I do love boots as well now thay are very sexy with stocking I would love to have...
    deleted deleted 26-30 2 Responses Jul 26

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    Absolutely love them! My love affair with them runs so deep. My first retail job in high school was at Nine West and it solidified the relationship lol!. I wear heels everyday at...
    SimplyserendipitousXoxo SimplyserendipitousXoxo 26-30, F 11 Responses Jul 26

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    I was caught twice the same morning,. I went outside dressed to check if garbage man had came. My neighbor also came out to check at the same time, he just said Hi and waved. I...
    meg1cdforyou meg1cdforyou 66-70, M 1 Response Jul 25

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    How are you planning this weekend girls...I was planning to go for shopping wearing butt length skirts with no panties wearing ..and the whole sunday cleaning the house wearing...
    Suhanicrossy Suhanicrossy 22-25, F 2 Responses Jul 25

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    I'm a certified shoe junky. I use to hate shoes, because I could never find a pair that fit. Always too long to get my toes in, and then my heel would slide around. A few years...
    bajep bajep 56-60, M Jul 25

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    Love wearing my Blcak Leather high heels:)
    JennyTom JennyTom 36-40, F 3 Responses Jul 25

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    Heels feeling sexy nice and taller then I am love turning heads!
    Analisa70 Analisa70 41-45, F 15 Responses Jul 24

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    I am working on it, I really have to wear some of this leather, but I only want to buy NEW LEATHER HEELS!!!!!!
    JennyTom JennyTom 36-40, F 1 Response Jul 24

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    Tom read me the RIOT ACT!!!!! Clean up your high heel closet, or NO more high heel purchases!!!!!! Some I still haven't worn, others I have only worn once and I still want more...
    JennyTom JennyTom 36-40, F 2 Responses Jul 24

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    I am 5'11 1/2" tall barefoot. With my 4" high heels I stand about 6'3 1/2" tall. I love being tall for many reasons; such as reaching things above my head, dancing, and enjoy...
    familycamping familycamping 31-35, F 7 Responses Jul 23

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    My family had told me they were going on vacation the week of my birthday. They left that Friday and I had the house to myself. Or so I thought. Saturday at noon I put on my...
    MsElle88 MsElle88 22-25, M Jul 23

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    I'm 15 and I wear heels in public almost everyday and I get loads of compliments on my shoes and my courage
    blakethomas0077 blakethomas0077 18-21, M 3 Responses Jul 22

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    What's up everyone, I go by highheellover23 and I am a straight married male that loves to wear high heels. I have been wearing heels since I was the age of 12. One day my cousin...
    hiheellover23 hiheellover23 31-35, M 7 Responses Jul 22

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    My family was leaving for dinner and I didn't wanna go, right when they left I rushed to my sisters room and I had this all planned out. I put on a thong and sports bra. Put in...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 1 Response Jul 21

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    I was with my grandma for weekend. I went there wearing my boy clothes and under I wore, garter belt, nylons, thong, girdle and a bra. All my girl clothes u couldn't see. So my...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 2 Responses Jul 21

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    Girls really do love heels, while guys do love Kicks....
    jasminpao jasminpao 26-30, F 8 Responses Jul 21