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I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 216 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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    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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    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 3 Responses Mar 30

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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 2 Responses Nov 5

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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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    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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    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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    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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    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 5 Responses Mar 4

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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

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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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    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 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 4 Responses Sep 21

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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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    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

    Hi let me share my story on high heels. I love wearing high heels from my teens. I'm addicted to the height power and dominating authority i feel on top of two ultra skinny steel...
    sajeesmiles sajeesmiles 31-35, F 8 Responses Nov 30

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    i love slutty high heels, i want to be locked into them, trained to wear ballet heels
    pinksissy78 pinksissy78 31-35, M 3 Responses Dec 2

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    It happened when I was 15. I used to house sit for my aunt. I did this for probably three or four summers in a row. Just a few nights here or a week there,never more than a week or...
    johndoe2701 johndoe2701 31-35, M 3 Responses Dec 8

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    love love love problem is larger sizes with good styles are scarce
    Efoile Efoile 22-25, M 2 Responses Nov 30

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    >Wouldn't mind taking these for a spin ^///^
    LittleBastet9 LittleBastet9 22-25, F 11 Responses Dec 18

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    I should love them but what I experienced yesterday for birthday celebration.. I am a short lady and wearing high heels is great, it gives allure and makes you feel taller than...
    MissM12 MissM12 18-21, F 5 Responses Dec 15

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    I will be wearing high heels today after a long time yeah :) he he
    cross2play cross2play 31-35 5 Responses 4 days ago

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    The story of the Pink Pumps.So I had just seen a movie, and it was a cute love story about a girl and a guy. Anyway, she wore these really cute pink kitten heeled pumps. I was...
    wistfulmiles wistfulmiles 51-55, T 8 Responses Dec 4

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    So many years ago, I had one of my first experiences wearing women's high heels. My family had gone away for a holiday, and because of clubs I was in, it was decided that I could...
    wistfulmiles wistfulmiles 51-55, T 3 Responses Dec 3

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    Watching the news tonight about a French study about high heels powerful sexy men would answer questions when a women is wearing heels us girls wearing heels because they are sexy...
    lvrofhose lvrofhose 56-60, M 6 Responses Dec 9

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    I'm a crossdresser and would like to buy some high heels for the first time I only bought flats before. I would love advice on how to walk in high heels before I buy them and how...
    Hiddensissy69 Hiddensissy69 26-30, M 9 Responses Nov 30

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    It was not my first time he caught but the first time I was caught by my mother (i grew up with step mom). It happened today. I'm 39 years old and I wear panties pretty much every...
    alexhawke alexhawke 36-40, M 2 Responses Dec 16

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    I am playing around at my desk in my stocking feet waiting for my high heels to dry and I just ordered these new high heels online. I love the pointed leather toes, if my husband...
    Shelley3457 Shelley3457 31-35, F 9 Responses Dec 10

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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 2 days ago

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    The first time I tried it was an EPIC fail XD, but now I can walk in high heels with ease :)
    ALostSiren ALostSiren 13-15, F 3 Responses Dec 2

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    I was caught by my mom when I was 17. I often slept wearing a a black and red teddiette that I had borrowed from her, along with some seamed stockings. She came into my room when I...
    LadyAndrea LadyAndrea 46-50, T 4 Responses 3 days ago

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    This pair of high heels is what I have , I bought them last year and I could walk directly a way with them no problem at all. The are very comfortable .
    Erikswimsuit Erikswimsuit 36-40, M 6 Responses Dec 2

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    My leather high heels got a little wet today in the rain and snowy slush. All the snow is gone and its just raining now. The leather got wet and I am drying them out now. It is a...
    Shelley3457 Shelley3457 31-35, F 13 Responses Dec 10

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    I just bought these pair of leather high heels to go to a few Christmas Parties in. The salesman over the phone promised me they use the best leather to make them and my feet will...
    Shelley3457 Shelley3457 31-35, F 5 Responses Dec 11

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    I love high heels. They give me a beauty life. They can transform.my mood from tamed and timid to wild and daring.
    Shi7 Shi7 41-45, F 7 Responses Dec 12

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    Oh high heels! So sexy, so incredibly awesome, I can be taller....nope I would die in the first 15 min! Seriously I'm better off using them as a bug killer, stabbing my eyes out...
    orchids2blu orchids2blu 36-40, F 8 Responses Dec 19

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    My husband bought me these calfskin high heels today. He said he will buy me leather every day for the 7 days of Christmas. What better way to Celebrate Christmas than with...
    Shelley3457 Shelley3457 31-35, F 6 Responses Dec 20

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    I love my toes painted red, This might be a thing for me to take from the holidays. The red toes are flattered by my leather high heels. I just LOVE them!!!!
    carla3457 carla3457 31-35, F 8 Responses Dec 20

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    A women in high heels so much sexier than those who wear flat shoes mmmm
    TeddyboyUK72 TeddyboyUK72 41-45, M 1 Response Dec 21

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    hi friends,my name is pradip. i am a teenager of 19. i am adicteed to high heels very much so plz message me on my account if any one is such as me
    Yagnipd Yagnipd 18-21 a week ago

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    I met my friend for a Brunch today, and my Fiance sat at the table behind us so we could do some girl chat. I didn't even realize we were playing with our high heels, and he took...
    carla3457 carla3457 31-35, F 3 Responses a week ago

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    I love nothing more than the feeling of slipping into a pair of sexy 5-6 inch high heels and touching myself. My ******* are mindblowing.
    hhfetish hhfetish 22-25, M 3 Responses 5 days ago

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    I only wear corsets on special occasions. They make me feel very sexy and feminine especially with nylons and high heels. I find they are too restrictive for everyday wear but I...
    kirsten29 kirsten29 26-30, F 1 Response 4 days ago

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

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    Legs, butt, high heels. Spiky ones too. Enjoy!
    jjoe01 jjoe01 41-45, M 4 Responses 1 day ago

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    Didn't think I would actually ever share this but yes I do. I keep it low key and only wear them outside when no one else is around. I have no interest in wearing any other form...
    jambo33 jambo33 51-55, M 1 Response 3 days ago

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    Around 12 months ago I went to a friend's place for the weekend. We had some drinks and did some jamming, he knows I wear heels so I wore some while I was there. I took a pair of 5...
    Luvnheels Luvnheels 51-55, M 1 Response Dec 13

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