I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 258 People

    Mother In Laws Boots

    i was caught by my wife wearing he moms boots she knew i dressed but freaked out
    louisetv louisetv
    May 9, 2012

    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
    3 Responses Mar 4, 2014

    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

    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

    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

    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
    4 Responses Nov 23, 2011

    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
    5 Responses Oct 17, 2012

    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

    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
    2 Responses Mar 15, 2015

    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
    7 Responses Mar 4, 2014

    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
    4 Responses Nov 5, 2014

    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

    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
    5 Responses Apr 23, 2012
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