Post

I Was Caught Wearing High Heels I Am Guy

Personal Stories, Advice, and Support 196 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...
    Josie06 Josie06 56-60, F 1 Response Aug 5, 2010

    Your Response

    Cancel
    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...
    10Camaro 10Camaro 66-70, M 6 Responses Oct 17, 2012

    Your Response

    Cancel
    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...
    metalman9780 metalman9780 41-45, M 1 Response Mar 4

    Your Response

    Cancel
    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...
    miata21 miata21 26-30 7 Responses Apr 23, 2012

    Your Response

    Cancel
    Just When I Thought I Was Getting Away With It - I'm a guy that wears high heels. I have been doing this for some 20 years, secretly. The last few years have seen me become more...
    Heellover Heellover 36-40, M 3 Responses Nov 19, 2012

    Your Response

    Cancel
    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...
    Girlyprincess1401 Girlyprincess1401 18-21, M 1 Response Mar 30

    Your Response

    Cancel
    I'm Sorry! - It was my first pair of stillettos. I was in my teens and living at my parents in a small village. I had worn them around the house and loved them indoors...
    Heellover Heellover 36-40, M 8 Responses Dec 2, 2009

    Your Response

    Cancel
    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...
    spaz1177 spaz1177 46-50, T 3 Responses May 12, 2012

    Your Response

    Cancel
    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...
    rppshoes rppshoes 41-45 5 Responses Nov 23, 2011

    Your Response

    Cancel
    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...
    krisyca krisyca 41-45, T 4 Responses Mar 4

    Your Response

    Cancel

    Related Experiences

    My favourite pair of high heels are purple suede with one inch platform and five inch stiletto heel and thin ankle strap. They are just gorgeous and I love to wear them out and...
    karenhobbs karenhobbs 26-30, T 5 Responses Mar 25

    Your Response

    Cancel
    These are my favourites.... Yves Saint Laurent Tribute high heels  
    karenhobbs karenhobbs 26-30, T 3 Responses Mar 30

    Your Response

    Cancel
    I love High heels I love how they manage my legs look and i love the way my hips sway as I'm walking. They are my number one weakness. I love them think i have over 40 pairs but...
    deleted deleted 26-30 3 Responses Apr 3

    Your Response

    Cancel
    one time I was laying on my bed listening to music and I was just wearing a tshirt and one of my vstrings and apparently my boyfriend came over and my mom just told him I was in my...
    annabanana95 annabanana95 18-21, F 1 Response 12 hrs ago

    Your Response

    Cancel
    A woman really looks supersexy wearing heels. I just love heels and am a heel fanatic. I have quite a collection and I want more. I love the way my butt looks wearing heels. Gimme...
    prettytoes prettytoes 22-25, F 11 Responses Mar 22

    Your Response

    Cancel
    I love wearing my moms leather ballet boots they make me feel so tall and I feel sexy in them
    shelbss shelbss 18-21, F 3 Responses Apr 5

    Your Response

    Cancel
    For a long time I thought I was transgendered but at this point in life I have made many self discoveries. The biggest of them is that I know I am not transgendered and that I...
    Jericho7 Jericho7 36-40, M 5 days ago

    Your Response

    Cancel
    So I've been reading about some experiences here that relate to wearing high heels. I have been wearing heels on and off for many years, buying a pair and then throwing them away...
    GiselleB GiselleB 51-55, M 2 Responses Mar 21

    Your Response

    Cancel
    I love wearing extremely high heels, but sadly I'm 5'6 and wearing heels makes me tower over a lot of men so I feel really awkward when I'm wearing them.
    darkanddesolate darkanddesolate 16-17, F 13 Responses 4 days ago

    Your Response

    Cancel
    High heels is one of the timeless and ultimate feminine pieces of attire that I shall love for all time. The slant of a vamp and curve of a heel can transform posture, gait and leg...
    waxingpoetic77 waxingpoetic77 36-40, F 9 Responses Mar 19

    Your Response

    Cancel
    I'm a female who loves guys in high heels. It's a huge turn on, as all crossdressing is to me, and I would love to hear from you guys of all ages! Don't be shy and message me.
    ShainaNichole ShainaNichole 18-21, F 7 Responses Mar 29

    Your Response

    Cancel
    I am 5'9" tall and I love to wear high heels. I normally wear 4" heels. When I am in heels, I stand 6'1". This is great because my husband is 6'5" and great for dancing with him...
    ebonynbill ebonynbill 26-30, F 4 Responses 2 days ago

    Your Response

    Cancel
    Yes I do this a lot. Most of the time I don't realise I am doing it, such as when I'm watching TV or on the phone at my desk. I just slip my heels out and dangle my heels by my...
    karenhobbs karenhobbs 26-30, T Mar 30

    Your Response

    Cancel
    Ok, I guess I love high heels since I was 5 years old. Why ? well... its my old sister and my mother's fault. When my sister got her first payment at her first job (she was about...
    alexaduarte alexaduarte 31-35, T 3 Responses Mar 18

    Your Response

    Cancel
    I got caught wearing my Mum's panties when I was 14, I was wearing a pair of her silky purple briefs. I used to wear them so much and then put them back. I was walking around the...
    LucyTG LucyTG 26-30, T 4 Responses Mar 19

    Your Response

    Cancel
    I have ALWAYS loved high heels. As a teen, I probably had 10-20 pairs. Now, I have way less because it is not easy finding them in my size. It sucks!
    MrsGrisham MrsGrisham 22-25, F 3 Responses Apr 10

    Your Response

    Cancel
    This past weekend I decided to go shopping for shoes. I was dressed in skinny Aztec print jeans with knee high boots with 2.5" heels, a white ruffle blouse and a short black...
    Brandie1960 Brandie1960 41-45, M Apr 2

    Your Response

    Cancel
    I have shoe shopping problems .. I buy all the shoes I want and obsessed with heels , when I was a teenager I used to wear them all the time and after my daughter was born I didn't...
    daisy92 daisy92 18-21, F 3 Responses Apr 2

    Your Response

    Cancel
    Hey can I get a vote or opinion guys? and girls? what do you like better? Closed toe heels, open toe heels, or peep toe heels?
    JessicaEvette JessicaEvette 22-25, F 99 Responses Mar 21

    Your Response

    Cancel
    I don't wear heels but I surely would love to start wearing them especially these gusippie
    Reynastaxx Reynastaxx 26-30, F Apr 4

    Your Response

    Cancel
    Ladies: wearing heels is not sexy if you walk like a new born calf in them.
    jojo0915 jojo0915 31-35, M 12 Responses a week ago

    Your Response

    Cancel
    I just got back from Payless when I bought a pair of Women's Haley Ankle Strap Pumps (I have them on now). I liked them so much I just submitted a review for them: "I just love...
    kathej kathej 66-70, M 4 Responses Apr 7

    Your Response

    Cancel
    I've been caught many times wearing my sisters lingerie and it's funny because my crossdressing started because of my sister. My sister and I are only two years apart and when we...
    Dirtyblondeslut69 Dirtyblondeslut69 22-25, M 5 days ago

    Your Response

    Cancel
    Im wearing ultra sheer black seamless hold up stockings and 5 inch peep toe patent leather pumps. It's barely 9am and my feet already hurt but it's worth it. ;-)
    bellablush21 bellablush21 31-35, F 3 Responses Mar 26

    Your Response

    Cancel
    And I also like short guys haha go figure...
    shimmersandsparkles shimmersandsparkles 26-30, F 4 Responses 1 day ago

    Your Response

    Cancel
    My favorite heels are pumps, I love them so much but it's a challenge to walk in them.
    kaseymwt kaseymwt 22-25, F 5 Responses a week ago

    Your Response

    Cancel
    I want to go heels shopping with some of my female friends... Might even buy them some shoes!
    grahamc222 grahamc222 22-25, M 2 Responses 22 hrs ago

    Your Response

    Cancel
    I was 13 and spending a couple of weeks with my grandma and aunt's house for during the summer. they had gone to the store and left me to watch TV. I decided to explore my aunts...
    sissyroni sissyroni 51-55, M 1 Response a week ago

    Your Response

    Cancel
    I got caught by my ex wearing hers she made me take pics and videos and then she made me get diapers and a pink bow for my head
    Subsissy42 Subsissy42 41-45, M 1 day ago

    Your Response

    Cancel
    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

    Your Response

    Cancel
    A night out as Rhonda had me visiting a local establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was...
    SweetRhonda SweetRhonda 51-55, T 4 Responses Apr 8

    Your Response

    Cancel
    Tonight I got caught by my girlfriends best friend, do to panty lines. Who would of guess that is a dead give away
    tellmesomething1 tellmesomething1 22-25, M 2 Responses Mar 25

    Your Response

    Cancel
    This happened when I was 15. I'd finished rugby training (night training after school) and went into the shower room for a shower. To set the scene, it was a communal shower with...
    Zacey Zacey 31-35, M 1 Response Mar 22

    Your Response

    Cancel
    I was at a party and a group of us were playing kings cup, one of the cards was a dare card. Soon enough I got the dare card and my friend got to dare me. She dared me so I had to...
    Markhill111 Markhill111 22-25, M Mar 25

    Your Response

    Cancel
    today I went to my friend's house we went outside and did random thing but I fell in a lot of mud so I went inside to take a shower I didn't know anyone else was home so I didn't...
    deleted deleted 26-30 4 Responses Mar 26

    Your Response

    Cancel
    I was seven months pregnant with my first child. My husband and I had driven up the coast and attended church and then had a nice, romantic dinner overlooking the beach. On the...
    lostworlds lostworlds 46-50, F 2 Responses Apr 6

    Your Response

    Cancel
    The uncertainty is exciting. I will go for drives in a skirt nylons shoes and a blouse with no make up or wig. Then I will go into stores like corner store or a coffee shop or the...
    Brandie1960 Brandie1960 41-45, M 3 Responses Apr 9

    Your Response

    Cancel
    I remember once when me and my ex-husband were making love on the sofa as we thought we had the night too our selfs. All I remember was my daughter and her boyfriend at the time...
    SalinNY SalinNY 46-50, F 6 Responses 5 days ago

    Your Response

    Cancel
    This morning !! the bin man got an eyeful LOL
    kirstyisback kirstyisback 36-40, F 1 Response 7 hrs ago

    Your Response

    Cancel
    I where them only around the house, I'm a male love all women stuff
    astroboy4545 astroboy4545 61-65, M 3 Responses Mar 20

    Your Response

    Cancel