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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 246 People

    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 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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    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 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 7 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 1 Response Mar 15

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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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    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 1 Response Aug 22

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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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    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 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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    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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    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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    Related Experiences

    My heels clicking on the floor as I open the door you know it's coming as I tease you stripping my clothes off slowly and just taking every bit of letting you caress all over my...
    Lightdreamer11 Lightdreamer11 18-21, F 16 Responses 3 hrs ago

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    My newest calfskin heels:)
    JennyTom JennyTom 36-40, F 6 hrs ago

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    I love for my wife to wear heels stockings anklets short skirts and go out to run errands I enjoy the looks she gets from other men and I love for her to flirt and do what ever she...
    karpaul karpaul 51-55, M 1 Response 1 day ago

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    No matter how nice the clothes are, the shoes make the outfit!
    Mrskatearch Mrskatearch 31-35, F 1 Response 1 day ago

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    I enjoy wearing high heels. When we go out I put on my heels and a short little black dress. There is a pole where we party and I like dancing on it. They make me a little taller...
    Timeparadox1 Timeparadox1 46-50, F 7 Responses 2 days ago

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       This is also posted under "I Got Myself Into A Self-bondage Experience I Could Not Get Out Of ".  I started dressing in my mothers clothes when I was ten with her...
    MichelleTiedup MichelleTiedup 56-60, M 3 Responses 3 days ago

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    So this just happened about 15 minutes ago, I went downstairs to get some stuff from my car and before coming back up I decided to sit on the steps and have a smoke. As I had just...
    sparkzones sparkzones 26-30, M 4 days ago

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    As you will see from other posts over time, my wife is so extreme in many ways. She really loves wearing heels as high as five or six inches, with a thin sole and needle thick...
    rocky139 rocky139 70+, M 1 Response 4 days ago

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    So love women (men also) wearing heels so high their feet stand straight down! Even better with a needle thin heel!
    rocky139 rocky139 70+, M 1 Response 4 days ago

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    I am a 15 year old bit and ever since I was young I have loved wearing high heels and I have mastered walking in them. My cousin likes to party so I normally wear hers as they are...
    Alluakbar69 Alluakbar69 70+, T 1 Response 5 days ago

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    Being a tg of course I used to be a guy in heels, but the feeling of wearing them is still the same for me, it feels great!
    DutchGasPedalGirl DutchGasPedalGirl 46-50, T 3 Responses 6 days ago

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    The last time i was caught I'd been out drinking with friends and as i was i no state to drive decided to stop over at my friends house as i wasnt at home i didnt have any hose...
    deleted deleted 26-30 6 days ago

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    I love wearing heels in bed..... So sexy
    thighspread thighspread 18-21, F 5 Responses 6 days ago

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    There's never anybody on here late who will chat about heels. If you would like to I'm usually on at this time. Please let me know
    highheelsrule highheelsrule 18-21, M 2 Responses Aug 25

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    My 42 year old female neighbor went out of town for a few days and she wanted my parents to watch her house but they got me to. On the second day I got curious and was in no hurry...
    deleted deleted 26-30 2 Responses Aug 25

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    Ok guys my plan didn't work, I didn't ask but it's ok now, I'm chillin In Bed tucked up (ball*) nice and cosey in a nice pair of black tights, night heels, short dress and pulkadot...
    Lucy14CROSSDRSSER Lucy14CROSSDRSSER 13-15, T 1 Response Aug 24

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    I love high heels and favorite color is blue heels is my favorite accessories.
    Kelly72898 Kelly72898 16-17, F 5 Responses Aug 24

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    I am just sick and tired of this EP Allie removing my stuff. This one is not even offensive, just a country girl wearing a daisy dukes and fully clothed. I am outta here! This is f...
    jjoe01 jjoe01 41-45, M 5 Responses Aug 23

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    New found love for heels and pretty obsessed with them at the moment! Message me if anyones in the mood for some shoe talk :)
    amyp98 amyp98 16-17, F Aug 22

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    I didnt start wearing stockings until I was 18 and understood the power stockings had over men :) I wore thigh highs in my teen years, was like wearing stockings, but its not the...
    satnlacy satnlacy 22-25, T 6 Responses Aug 22

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    I love the look of them (stylish, sexy, beautiful leather) and I love wearing them and I love the way they look on me. I wish I could afford designer shoes (Jimmy Choo, Manolo...
    Heidiaimelesfemmes Heidiaimelesfemmes 26-30, F 10 Responses Aug 22

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    Hello everyone! I'm a guy and I love to wear heels. Maybe I love high heels more than my girlfriend. I use to wear them and watch my female part in the mirror and I like it a lot...
    CDL17 CDL17 18-21, M 5 Responses Aug 22

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    As a young boy I was fascinated by the look of a female foot in high heels stepping on a pedal. I watched TV looking for girl bands with a female drum player, I sat in the back...
    DutchGasPedalGirl DutchGasPedalGirl 46-50, T 3 Responses Aug 21

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    A beautiful looking woman in stiletto boots, strutting her way home with supermarket bags dangling from either arm, not perhaps the exact image she was looking for but what can you...
    Gavriella Gavriella 26-30, F 1 Response Aug 21

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    I didn't know how to go about this at first. I tried eBay first only to find that heels in my size were way overpriced. Things all changed when I went to the Goodwill store one day...
    BoyNbraNpanties BoyNbraNpanties 26-30, M 4 Responses Aug 21

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    Duality of thoughts about a heeled lady! Last week, i came across a lady in her early 30's in a London Underground train. She was seated about 5 meters from me. I couldn't help...
    lockedheels lockedheels 31-35, M 7 Responses Aug 20

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    high heels in the bedroom is very nice
    jackbiker jackbiker 41-45, M 4 Responses Aug 19

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