I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 269 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
    5 Responses Apr 23, 2012

    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

    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
    3 Responses Mar 4, 2014

    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

    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

    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

    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

    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
    3 Responses May 12, 2012

    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

    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

    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

    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

    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

    Related Experiences

    I told you these leather heels are comfortable, I bought so many pairs just different shades, LOL
    JennyTom JennyTom
    41-45, F
    1 Response Apr 21
    I have over 30 pairs of high heels in my closet alone. I love all kinds of shoes; especially my high heels. I love my 4 inch heels because it makes me stand over 6 foot tall.
    femaleslovesummer femaleslovesummer
    36-40, F
    7 Responses Apr 21
    Thanks E P. As long as you are remembered you will never ever be forgotten. 😇
    isacallandra isacallandra
    26-30, T
    Apr 20
    These are made from top quality leather, my FEET love them so much:) so does my husband, LOL:)
    JennyTom JennyTom
    41-45, F
    1 Response Apr 20
    As a Phy Ed teacher for years, you find out that briefs and boxers don't cut it as underwear for work. No matter what my parts just kept falling out and hanging in view at...
    talking4fun talking4fun
    51-55, M
    1 Response Apr 20
    Was caught this morning by my 70year old neighbor he come around the house I was sitting in the patio he coughed I looked up reading paper and drinking coffee .i was wearing a...
    lvrofhose lvrofhose
    56-60, M
    2 Responses Apr 19
    I was out walking on my land near the county road today. I was on my driveway, maybe 100 feet or so from the road when I hears noise of an approaching vehicle. We usually get 3...
    Earthbob Earthbob
    66-70, M
    Apr 18
    Today I only wore a red blouse, black skirt and black tights with converse, but last week was a little better. I got to wear a white blouse with the company logo and my name...
    Talltonedgirl Talltonedgirl
    26-30, F
    1 Response Apr 18
    I love wearing high heels the higher the better they look so sexy
    jennnjay jennnjay
    56-60, F
    12 Responses Apr 18
    I should of worn thee shoes again today, the leather is so comfortable on my feet:) But I never were the same pair 2 days in a rom, LOL, This is good soft thin leather:)
    JennyTom JennyTom
    41-45, F
    2 Responses Apr 18
    I want to worship them on women or man I'm 15
    MaleSlaveHighHeel MaleSlaveHighHeel
    18-21, M
    2 Responses Apr 18
    I got caught shoplifting by my mom omg this sucks *** btw (I'm black) I did this more than once I took some makeup from target I put them in my pocket of my bomber jacket in the...
    Doobty Doobty
    18-21, F
    1 Response Apr 17
    I love wearing nylon stockings with suspenders. They make me feel so feminen and sexy too The feel of the suspenders tight on my thighs and butt makes me feel so good
    Lisagcup Lisagcup
    26-30, F
    2 Responses Apr 17
    This was just like an hour ago, but I was with my friend at the mall and she introduced me to shoplifting. We go a thing and other things and this was my first time. We then when...
    raspberri raspberri
    18-21, F
    3 Responses Apr 17
    Ever since I was little, I've been so shy that I'm practically hostile around guys. I have two brothers that I love and of course a dad, so it's not like I think they're some kind...
    BellaGrace1 BellaGrace1
    16-17, F
    1 Response Apr 16
    I was 14-15 years old. I made the first steps in the knowledge of joy naked body. My first favorite place for experiments was the roof of our house. I was there frolicking naked...
    tara0 tara0
    36-40, F
    2 Responses Apr 16
    Well you can't see the heels but I love the bling on these sandals!
    KathleenD13 KathleenD13
    51-55, F
    3 Responses Apr 16
    Two years ago, I got caught shoplifting at store called Sears. What makes it worse is I stole small chain that only 8$. After I stepped out the door, LP agent called me and ask...
    deleted deleted
    26-30
    2 Responses Apr 14
    so you know the story of the new guy next door ok so today I come out to get the newspaper in a white t-shirt and panties to tease him because he getting back from his run...
    gueenemma418 gueenemma418
    18-21, T
    2 Responses Apr 14
    I was about 14, my sister was a WPC and one evening she and 4 other girls from her shift were at our house They were having a girly night in, and one of them said, if I was to be...
    wilcunhut wilcunhut
    46-50, M
    Apr 14
    I love to wear my mini skirts with my heels
    mischef mischef
    46-50, T
    3 Responses Apr 14
    I just love my high heels they are so cute
    mischef mischef
    46-50, T
    3 Responses Apr 14
    today my mom lift home for work after she lift I put a pair of panties on than my jeans a bra than my shirt I went to are apartment to check are mail I get back and that when I...
    gueenemma418 gueenemma418
    18-21, T
    1 Response Apr 14
    5 inch heels are about all i can handle. going any higher, I feel like I'm going to fall over and break something.
    lauratdc lauratdc
    46-50, T
    1 Response Apr 13
    My pile of need to be shined, most are all scuffed up from wearing out, the work NEVER ends!!!!!!!
    JennyTom JennyTom
    41-45, F
    13 Responses Apr 13
    This is what the spikes look like on my leather high heels, OUCH!!!!!! ::)
    JennyTom JennyTom
    41-45, F
    Apr 13
    -Life In Transition: A Compilation of Memories-I was born biologically male, but over the course of my life, have realized that my mind and soul on the inside feels female. Women...
    KayleeBehrens KayleeBehrens
    18-21, T
    Apr 13
    sht :/ . she z fadinf a bit . or . shying away or sumin . posibly jus tired / exhausted / a bit burnt out .. hav had to b a guy too much .. n she was tryin to set us n her free...
    cdwishimatgurlCalandraBelle cdwishimatgurlCalandraBelle
    36-40, T
    1 Response Apr 13
    I would love to be a male bridesmaid in a wedding. Of course, I'd wear the same dress that the female bridesmaids are wearing. I'd let my hair grow out before the wedding and I'd...
    steevo895 steevo895
    51-55, M
    1 Response Apr 12
    ForcedCrosssdressingStory Pt1 Hey people! Well...This was a huge embarrassing experience that has happened recently. I went to my Aunt Kaitlen's house for 2 weeks because my...
    HiMyNameIsBlank101 HiMyNameIsBlank101
    22-25, M
    Apr 12
    no . {ok not relly jealous but efin wow !} . even tho u can utube guys dancin in heelz . mkez . i triedddd to do so for quite a while . like maybe 14 minutes . dagnabit not easy n...
    cdwishimatgurlCalandraBelle cdwishimatgurlCalandraBelle
    36-40, T
    1 Response Apr 12
    My fiance and I have moved to a place out in the undeveloped countryside of Florida. We were sitting in our living room drinking coffee and reading, with the curtains open, when...
    feelsogd feelsogd
    61-65, M
    3 Responses Apr 12
    heel75 heel75
    31-35, M
    2 Responses Apr 12
    I love wearing girls panties and underwear, makes me feel so sexy! I just love being girly!! :)
    MattCD95 MattCD95
    18-21, M
    2 Responses Apr 11
    This is embarrassing My name is Damien I am a male teen crossdresser It was a school day and I forgot that I had painted my nails last night red so it was no problem really. I...
    EvaMarie1406 EvaMarie1406
    22-25, F
    3 Responses Apr 11
    I was in a store the other day starring at a woman wearing jet black hose & shinny black heels as I was standing there near the pantyhose section she asked what I was looking at...
    Iwearpantyhoseallthetime11 Iwearpantyhoseallthetime11
    36-40, M
    Apr 10
    I love to wear my heels around the house while I'm relaxing and playing around on the net.
    blfdwvjlee blfdwvjlee
    31-35, M
    1 Response Apr 10
    I stared wearing heels when i was a teenager I saw the return to oz for the first time thought it was awesome a man was wearing the ruby slippers and since then I have been total...
    blfdwvjlee blfdwvjlee
    31-35, M
    Apr 10
    I never liked the idea of arranged marriage. Because I can't just marry a guy who don't even know. My mom's was one. The result she's separated from my father because he's a psycho...
    imasurvivor92 imasurvivor92
    22-25, F
    2 Responses Apr 10
    So do I. What do you think of these
    Chase02 Chase02
    41-45
    7 Responses Apr 9
    School Days,Good Ol Golden Rule Days-In my elementary school it was required that all students wear tennis shoes,tucked in shirt every day regardless of the type for boys and for...
    2ndBorn1stSon 2ndBorn1stSon
    22-25, M
    1 Response Apr 8
    wasnt really caught as she let me wear them but when i was younger my sister used to let me wear her footie pajamas and her bright pink juicy couture velour hoodie! they were so...
    kinkyturtle95 kinkyturtle95
    18-21, M
    Apr 8
    I love wearing high heels when I am dressing up to go to work or out for the day or evening with family and/or friends. I have many different colored high heels for all occasions...
    familynudiststogether familynudiststogether
    36-40, F
    5 Responses Apr 8
    For the last year I have not touched a single pair of high heels. I don't know why i ever wore them unless they are orthopedic ally designed and cushioned they are horrible...
    moonlightflower moonlightflower
    22-25, F
    Apr 7
    In school days I used to wear my aunt's boots and high heels.
    nylonpassion007 nylonpassion007
    18-21, M
    1 Response Apr 7
    loveofheels loveofheels
    46-50, M
    Apr 7
    loveofheels loveofheels
    46-50, M
    Apr 7
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