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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 215 People

    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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    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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    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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    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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    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 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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    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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    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.
    IwantDomination IwantDomination 13-15, M 3 Responses Nov 5, 2014

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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 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 5 Responses Sep 21, 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 4 Responses Jul 18, 2010

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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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    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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    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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    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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    Related Experiences

    I love wearing high heels! However, I find that its very hard to find comfortable heels that I can stand in day in and day out. I recently found this amazing product that I thought...
    Heelswaps Heelswaps 26-30, F 1 Response Jan 13

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    My dating began in the women shoe store. I went to a big shoe mall to buy heels. I was in 3 inch navy blue pumps. I was just looking at the racks for something new. sales girl...
    heellover4 heellover4 31-35, M 3 Responses Jan 14

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    The moment I put on my red high heels I start getting all kinds of ideals I feel like I am on top of the world So I dance around until I twirled In my red high heels I can do...
    Goldenfairy Goldenfairy 26-30, F 3 Responses 20 hrs ago

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    I finally went walking in pair of high heels last night. It wasn't too racy, it was after hours in a quiet neighborhood in the valley here, but the boots were Nine West brown...
    laheelsmusic laheelsmusic 22-25, M 2 Responses Jan 13

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    If wearing Chef Dansko's are considered heels then yes I wear heels! I wear Dansko's with my skirt too!!
    AsianTransGirl AsianTransGirl 26-30, T Jan 9

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    I just love how they look and love how they make a women feel confident.
    deleted deleted 26-30 2 Responses Jan 15

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    I didn't take off all my make up and a female student notice a little eye make up. Thought I got it all.
    Therealjason Therealjason 31-35, F 1 Response Jan 6

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    I do enjoy wearing high heels.... They not only accentuate a sharp outfit.... But give me added height, and elongate my legs.... When I'm in a pair of heels...they give me added...
    sexygirl39 sexygirl39 41-45, F 4 Responses Jan 17

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    In my late teens as I described earlier I stole a pair of high heels from my neighbourer she was a cute lovely lady in her early thirties. It happened one day I noticed no activity...
    heellover4 heellover4 31-35, M Jan 6

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    It all started when I was 16. My neigbour was a cute 30 year lady. Her feets were so lovely and choice of her high heels were sophisticated. I fell in love for her feet but never...
    heellover4 heellover4 31-35, M Jan 5

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    I love wearing leather high heels, a little selfie in the mirror here to show off the sleek look of my high heels. High heels make me feel so good.
    Donna717 Donna717 36-40, F 2 Responses 5 days ago

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    He also bought me new leather high heels, and I am wearing them to work tomorrow, its been a great night.
    Donna717 Donna717 36-40, F 6 Responses Jan 8

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    Me and my girlfriend just moved to a new town and she ask me if I would like to go shopping with her so I said yes as I had nothing else to do. When we got to the mall she asked me...
    Manudglh96 Manudglh96 18-21, M 3 Responses Jan 6

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    Lina and me heading out in our high heels to see how many guys notice us, lol
    Donna717 Donna717 36-40, F 9 Responses 4 days ago

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    I must have fifty pairs of high heels! I am tall with long tapered legs and love to wear heels! I think I look sexy (my husband loves for me to wear heels!)! I wear them either...
    deleted deleted 26-30 3 Responses Jan 16

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    When I am dressed up or causally dressed, I love to wear high heels with my different types of attire. I have long legs and high heels are an asset for me to wear when out in...
    momlovespatriots momlovespatriots 36-40, F 3 Responses a week ago

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    Nothing like high heels. It definitely adds a point to any female on the 10 scale. It doesn't hurt that I am a leg and feet man too. Heels will definitely get me rock hard000.
    lonestallion153 lonestallion153 31-35, M 1 Response Dec 26, 2014

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    Girls in high heels are so sexy to me. It's incredible.
    Warmonger100 Warmonger100 18-21, M 1 Response Dec 27, 2014

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    Legs, butt, high heels. Spiky ones too. Enjoy!
    jjoe01 jjoe01 41-45, M 4 Responses Dec 27, 2014

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    I wear high heels to work every day.
    Donna717 Donna717 36-40, F 33 Responses Dec 30, 2014

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    I love to see women in sexy high heels when you having sex
    luvps luvps 31-35, M Jan 3

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    The smell of a womans foot aroma left in leather high heels is one of my biggest turn ons!
    Renayde92 Renayde92 22-25, M 1 Response Jan 4

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    Whenever am unable to go out! I wear different pair high heels from my extra above average collection indoors & walk tip toe quite so no one else can hear what am upto, anyone like...
    cross2play cross2play 31-35 2 Responses Jan 5

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    I love to wear my bikini in high heels it makes me feel so god dam sexy
    mischef mischef 41-45, T 2 Responses Jan 9

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    I love when I have a "Same High Heels Disaster" with another girl at a party. It's not so disastrous. It's fun ;) Have you ever experienced the same situation?
    SurreptitiousTouch SurreptitiousTouch 31-35, F 4 Responses Jan 16

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    High heels make me feel feminine and powerful :)
    pushdolly pushdolly 18-21, F 11 Responses Jan 17

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    Anyone live in reading pennsylvania willing to get me high heels ?
    IwantDomination IwantDomination 13-15, M 1 Response 5 days ago

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    I used to wear stiletto high heels all the time Until u got knocked up and it started killing my feet and back.
    AiymaSnikies AiymaSnikies 22-25, F 2 Responses 3 days ago

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    So sexy to me plus heels were originally designed for men (make the taller ehh idk) All the same I find this hot and when I dress a guy in women's clothing I love them in heels...
    newasexy newasexy 26-30, F 8 Responses Dec 26, 2014

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    there is nothing more alluring than a woman in 4inch + heels. i just broke up with a gal who loved wearing them as much as i loved buying them for her. but in the end it was all...
    digitalcowboy digitalcowboy 51-55, M Jan 1

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    I recently ordered myself 2 new pairs of heels online. I couldn't wait for them to arrive. When they finally did, I put them in their hiding place and couldn't wait to slip into...
    jamie50 jamie50 51-55 7 Responses Dec 31, 2014

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    The Wife was out of town yesterday, so I decided to spend the day in my Blue Baby Doll , Blue Panties, Lace-Top Stockings and my new Blue Patent Platform Pumps that I had just...
    jamie50 jamie50 51-55 2 Responses Jan 4

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