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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 269 People

    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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    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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    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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    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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    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 8 Responses Mar 4, 2014

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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 2 Responses Mar 15, 2015

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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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    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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    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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    Nowadays, as transgender I'm female 24/7

    and (very) high heels are part of my daily outfit now but things weren't always like this. I got 'caught' by a paperboy...In the late 70s my parents took me age 13 on vacation, house sitting a house of an uncle and aunt of me. One day, my parents wanted to do some shopping and I...
    DutchGasPedalGirl DutchGasPedalGirl 46-50, T 2 Responses Aug 22, 2015

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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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    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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    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 5 Responses Apr 23, 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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    In my cross dressing days there was (at least)

    one other occasion where I was in heels in public and most likely that some people saw my heels. I was dressed in a rather tight blue dress made of thick cotton stretch fabric and I was walking in block heeled summer sandals. I was driving in my car in these shoes as I wanted...
    DutchGasPedalGirl DutchGasPedalGirl 46-50, T 1 Response Sep 3, 2015

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    Related Experiences

    me and my beautyes :). you like them? let me know ;).
    overkneeplatformboots18 overkneeplatformboots18 18-21, M 2 Responses 6 hrs ago

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    I am going to try and target 3 caught crossdressing stories by the weekend Here's story no1 they do come in parts. The bridesmaids story.... Hi my name Eric I am 17 and this is...
    EvaMarie1406 EvaMarie1406 22-25, M 11 hrs ago

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    well 2 years ago for Halloween right before a party I had no costume ideas, with my girlfriend knowing im a crossdressing fanatic her and her friend suggested I dress as a classy...
    crossdresserfun crossdresserfun 22-25, T 1 Response 12 hrs ago

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    Last night after dinner we went to the Rockingham Mall, in NH....and my husband saw these heels and was drooling over them. The toes are way to long for me, LOL, then he calls them...
    JennyTom JennyTom 41-45, F 6 Responses 15 hrs ago

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    High heels on and nowhere to go. My new open toed pumps but is my skirt too short?
    MissyFem MissyFem 41-45, T 3 Responses 18 hrs ago

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    It was was the fist day summer break it was just me and my mom home .I was in her room dressing up in her clothes i hear her come up so i tried to hid in her closet but it was to...
    laura1974 laura1974 41-45, T 4 Responses 1 day ago

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    You can't beat high heels in ladies makes any leg look long and slender add to that a very short skirt you got it made so ladies would you wear these
    oldmanofuk oldmanofuk 56-60, M 5 Responses 1 day ago

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    I remember when I was a young boy my mother left for work, so I thought I would play. I had on a pair of her panties and had taken out most of her slips and soft dresses. I had...
    anotheritguy anotheritguy 31-35, M 1 Response 1 day ago

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    So I had always been dressing whenever my parents would leave and run errands. So every time they left the house I would race into my moms room and immediately throw on a dress...
    lcd6993 lcd6993 22-25 5 Responses 1 day ago

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    Like many people on here I cross dress but I can never find high heels in my size at regular shop does any one know anywhere in Orlando (currently here for 2 weeks) or uk ?
    Rich195 Rich195 18-21, M 6 Responses 1 day ago

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    I remember as a child in the sixties, women walking round in stilettos and I developed a fascination (being closer to the ground as a kid) with people's feet. I'm not saying this...
    LadyTea LadyTea 56-60, F 11 Responses 2 days ago

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    I see groups for those who love 4 inch heels. I see groups for those who love 6 inch heels. What happened to giving love to 5 inch high heels? I have a couple of pairs of shoes...
    BizSuitStacy BizSuitStacy 51-55, T 3 Responses 3 days ago

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    I just can't wear these heels enough!
    insideout25 insideout25 31-35, M 3 days ago

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    I would love to hear what guys think of seeing high heels on a woman at work
    michellelaso michellelaso 41-45, F 58 Responses 4 days ago

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    Even though I'm 5'11", I wear 6" heels.
    LBCC2016 LBCC2016 31-35 1 Response 4 days ago

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    I am a guy that likes to wear high heels. I am not into the cd aspect so I prefer skinny jeans. My skinny jeans can go with anything... Platform heels, knee high boots or thigh...
    Platforms Platforms 46-50, M 3 Responses 5 days ago

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    I'm 19 and I just recently got caught stealing from Macy's over $175 worth of merchandise . This was my first time because I seen my friend do it and get away with it many times I...
    Boyer17 Boyer17 18-21, F 5 days ago

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    What is it with my heels not just any heels they have to be high heels and open were you can see the foot and toes and ties around the leg when I have mine on I get so horny I find...
    sweetpinkrick sweetpinkrick 26-30, F 6 Responses 6 days ago

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    Andy you should be able to see the leather grain in these high heels, and if you could feel it, it would melt you, its real calfskin, LOL:)
    JennyTom JennyTom 41-45, F 9 Responses 6 days ago

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    Another pair of my leather high heels, look Andy its real calfskin leather pointing it right at you, LOL:)
    JennyTom JennyTom 41-45, F 4 Responses 6 days ago

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    Again a friend thinks my high heels are made from fake leather, and you see the leather in this older pair of my heels is real???? This is real calfskin leather, LOL:)
    JennyTom JennyTom 41-45, F 3 Responses 6 days ago

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    Breaking in my new high heels, very soft and comfortable:)
    JennyTom JennyTom 41-45, F 5 Responses 6 days ago

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    Got a brand new pair of leather high heels before the movie last night:)
    JennyTom JennyTom 41-45, F 1 Response a week ago

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    Bought a new pair of high heels in store a few days ago. They are a pair of peep toe heels with a snake pattern. It's really great that I now have the confidence to go in and...
    yoyojams yoyojams 18-21, M 2 Responses Jan 28

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    just been caught by a delivery driver wearing a Simon Jersey black dress and apron. The wife thought it was hilarious there she was in jeans, jumper and trainers and the driver...
    Bower99 Bower99 56-60 2 Responses Jan 27

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    Ep admin I won't bother post anymore stories as when I try too,,you won't post them and say they are in violation of this,that n the other...you won't even let me appeal against it...
    duranie duranie 36-40, M Jan 27

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    My favourite summer outfit Love Summer time here in Australia! Thinking of wearing my bikini by the pool when I get home but I do need someone to put on suntan lotion on my back?
    deleted deleted 26-30 2 Responses Jan 26