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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 216 People

    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 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 16-17, M 4 Responses Mar 30, 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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    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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    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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    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 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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    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 4 Responses Nov 5, 2014

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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 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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    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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    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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    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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    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 am a straight male who loves wearing high heels. The other day, when I got out of work, I put on my black boots, with 4" stiletto heels, and ran all of my errands...got gas, when...
    Stilettoheelman Stilettoheelman 41-45, M 2 Responses Feb 9

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    I'm a shoe fanatic and wearing high heels are my shoes of choice.
    candyblu candyblu 46-50, F 4 Responses Feb 9

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    I am professionally employed as an attorney. I am expected to be properly dressed including underwear and heels. I love wearing my 4 inch high heels when I am dressed up and at...
    femaleofficeworker femaleofficeworker 51-55, F 10 Responses Feb 9

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    Regardless of what I am wearing I always include high heels with my outfits. I love to dress up, go casual, and wear a bikini with my high heel shoes.
    tallmomwithkids tallmomwithkids 31-35, F 5 Responses Feb 11

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    I just wish I could find cheap ones in my size! :'(
    JulieCakes JulieCakes 16-17, M 4 Responses Feb 9

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    You're 14, or 15, or 16, maybe even a little younger. You have this obsession about dressing as a girl. One of the things that gets you excited is wearing high heels. I can tell...
    MiriamK MiriamK 56-60, T 5 Responses Feb 13

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    I love wearing high heels. I have heels from 3 1/2 in. to 5 1/2 in. I always wear stockings with my heels they make my legs look so much better!
    alison56cd alison56cd 56-60, T 4 Responses 4 days ago

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    I love wearing high heels when dressing up, going casual, or dressing down. I wear my high heels with all of my outfits. I love the compliments I receive from others on my...
    dianefisher dianefisher 22-25, F 1 Response Feb 1

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    I just love dressing in a corset with garters and stockings under my little dresses and high heels. Mistress enjoys seeing me go about my day dressed in in short babydolls and...
    Plugslave Plugslave 31-35 1 Response 7 hrs ago

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    After a night of drinking n going home i decided 2 dress up. So i snuck in 2 my moms room while she was asleep tryn 2 b quiet as possible without waking her(stealth mode) crawling...
    whitwhit86 whitwhit86 26-30, M 4 Responses Feb 5

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    I have been caught twice. when I was 12, I used to wear my moms pantyhose, heels and dresses...also makeup and her wig. I hid them in the corner of the bathroom behind the tub...
    dressupgina dressupgina 41-45, M 1 Response 20 hrs ago

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    I am professionally employed as a CPA of a large business and accounting firm . Therefore, I must be appropriately dressed in my professional office attire or outfit at all times...
    businesswomanathome businesswomanathome 36-40, F 7 Responses Feb 15

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    I love shopping for and wearing my high heel shoes. I get so turned on by shopping for and wearing these types of shoes. I wear my high heels with everything and even when nude...
    tallmomwithkids tallmomwithkids 31-35, F 8 Responses Feb 12

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    When dressing in any of my outfits I love wearing my 4 inch high heels. I am quite tall with long legs and love to show them off in short dresses, skirts, shorts, lingerie, or...
    momfromcolorado momfromcolorado 41-45, F 10 Responses a week ago

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    One of my absolute FAVORITE parts about being a woman.. I love high heels! And they make my legs look great
    SarasXXXsecret SarasXXXsecret 31-35, F 13 Responses Feb 3

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    There is something sexy about a woman in high heels. I love when my gf wears a pair of stiletto's. So hot! I'll buy her a pair just to wear when we, ahem, you know.
    Jwalk954 Jwalk954 26-30, M 3 Responses Feb 13

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    As a real woman or lady, I love dressing up in a nice short dress or in a skirt with a nice looking blouse, appropriate and matching underwear, hose, and in my 4 inch high heels.
    businesswomanathome businesswomanathome 36-40, F 1 Response Feb 15

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    I really want to wear high heels but how can I do that without anyone knowing :(
    IneedPleasure IneedPleasure 13-15, M 5 Responses Feb 16

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    In my leather high heels today, had to have one day out of my leather boots, hehe
    JennyTom JennyTom 36-40, F 7 Responses Feb 18

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    When wife wears high heels I smile because she looks so good
    Oldermancda Oldermancda 61-65, M 2 Responses a week ago

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    Females and high heels are my weakness
    userxxxhook userxxxhook 31-35, M 3 Responses 1 day ago

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    I was caught by my landlord we told him we were having problems with the pipes in the bathroom for master bedroom I was home alone so I was crossdressed I did not realize he had...
    Edwardkarter Edwardkarter 36-40, M 2 Responses Feb 2

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    I think I was caught as week ago n the bathroom on the pot thought i locked the door but found out i didnt. i dont think I pulled my pants up quick enough n my boss probably seen...
    whitwhit86 whitwhit86 26-30, M Feb 16

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    I was caught crossdressing today it was my fault as i got the courage to try a dress on in the changing rooms of a clothing store the store clerk said" i looked good" i enjoyed the...
    LucyJarvis LucyJarvis 22-25, T 1 Response Feb 16

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    These are my newest pair of black booties. Last night, my girlfriend and I went for drinks, and she asked me to surprise her with what heels I would wear. She was wearing black...
    Stilettoheelman Stilettoheelman 41-45, M 2 days ago

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    so my wife already knows I dress, and I have been doing it openly with her for a few years now. Well a few nights ago my daughter came downstairs and caught me in my wig and no...
    Allyson02 Allyson02 31-35 3 Responses 11 hrs ago

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    Fancy dress party, and that TV commercial. Firstly, there is an add on telly here in the uk. It's for a price comparison website "money supermarket" the catch line is, on the...
    Heellover Heellover 36-40, M 4 Responses 1 day ago

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    I've been caught several times by my wife. She's not really cool with it but does tolerate. I've never dresses with wigs, make-up or anything female from the waist up. I Just like...
    shadowplt shadowplt 51-55, M 1 Response 4 days ago

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    I like wearing heels. One thing I hate I'm 5'8 It makes me way taller. I hear them people talking "your already tall remove them heels" I remove them so they can shut up
    lorrena19 lorrena19 18-21, F 3 Responses Feb 7

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    My girlfriend and I wearing our sexy peep toe heels. I'm in the red and she's in the fuschia. I love how our toes are kissing ♥ Which do you prefer, red or fuschia?
    SurreptitiousTouch SurreptitiousTouch 31-35, F 21 Responses Feb 2

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    The first time I became aware of the erotic sound of heels was when "Auntie" Mabel brought me a drink when I was 14. Her shoes had straps around her ankles and I wanted to have a...
    Lin79 Lin79 31-35, T 1 Response Feb 14

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    The higher the heel the closer to god right? Or....maybe that was hair? Either way I love heels is there really any other shoe lol. The best part is I get to have heels and only...
    Sunshinegal4u Sunshinegal4u 26-30, F 6 Responses 4 days ago

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