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I Am a Man Who Loves Wearing High Heels

Personal Stories, Advice, and Support 753 People

    Heels At Work

    When I got in this morning the boss asked me if I would mind checking the out buildings, the guy that usually does it had called in sick. I had done this once before, most people hate it coz you are by yourself all day long. I didn't mind at all coz I knew I could do it all in...
    Heellover Heellover
    36-40, M
    5 Responses Nov 16, 2011

    My wife has me heeled

    when home. Not much in public
    plrvs64 plrvs64
    41-45, M
    3 Responses Jan 12, 2016

    Always Looking For More

    I absolutely love wearing high heels....can't get enough of them. I presently have about 45 pairs and am always looking for more. My wife has a pair that I love and have been on the look out for a pair for myself. Problem is, I can't seem to find them. Her's are from Club...
    scaff69 scaff69
    2 Responses May 19, 2011

    Why I Love Wearing High Heels

    Because I am a man I know to some it is odd that I love wearing high heels, but I love the feel of them.  How they make me feel taller and thinner.  How they make me feel more sensuous.  How they make my feet appear smaller and enhance the shape of my legs.  I...
    shoestodiefor shoestodiefor
    2 Responses Apr 12, 2009

    I'm Definitely That Kind Of Man

    Oh, yes I do. I love to wear high heels. I started to get over to my fear and went out sometimes in high heels in daytime. The first few steps its like a thrill, but the truth is its better to do that in daytime. Okay, there is more people on the street, and its a reasonable fear...
    VivienXX VivienXX
    26-30, T
    3 Responses Nov 17, 2010

    My Second, First Time

    I went back to her place after a friends party. When I got there I had an attack of guilt. Even though my wife could do that to me, I can't do it to her, I'm just not like that! She had a pair of stilletoes by the sofa, I saw that they were my size. I don't know what I said or...
    Heellover Heellover
    36-40, M
    1 Response Nov 8, 2010

    Skid Marks

    I began wearing high heels at a very early age, and after some initial fun and humor, it was understood that I shouldn't be wearing my Mom's high heels. Any time I had the opportunity, however, I'd be sashaying around the house with a free spirit. When Mom would ask if I had been...
    GinaViz GinaViz
    56-60, F
    3 Responses Aug 22, 2012

    I Love To Wear My Heels

    I have an addiction to womens shoes and boots. Since moving from a big city in Texas to a small town in Oklahoma I dont get to wear my heels when I go out anymore. Fortunately there are a few good stores to shop for them in town but the people here dont know what metrosexual is...
    PupJoJo PupJoJo
    31-35, M
    4 Responses Feb 25, 2011

    Well, truth of the matter I love wearing all

    female clothing. And I'm wearing 5 inch black heels as I type this.
    RayanneA RayanneA
    56-60, M
    1 Response May 23, 2014

    My Loves

    One of my first experiences in CD was putting my mom's classic black pantyhose and some high heels. When I put on those heels its like it just fit into my foot. It felt so incredible to wear them, although they hurt, I'm not gonna lie. But the heels and the hose made my legs look...
    deleted deleted
    3 Responses Nov 29, 2010

    Shopped For Heels By Myself For The First Time Today

    What a wonderful day, I set out today to get a pair of heels. I drove to a store I knew had something I wanted. Well as Im looking at what I wanted, a sales girl walked up to me and said, those would look cute on you. OMG !!!!! did she really say that????. I tryed to think of...
    EricaDress EricaDress
    41-45, M
    10 Responses Mar 11, 2013

    Have You Ever Dated A Girl For Her Shoes

    I know this sounds shallow but I could never date a girl who wears flats. I have always been open about my fetish for heels and although it has occasionally caused problems it certainly beets living a lie. I have been seeing my current girl for 5 years, we both have bi tendencies...
    deleted deleted
    1 Response May 25, 2013

    Friends Continue To Accept It

    I was at an old friends house for a few drinks and BBQ. (Dressed entirely in man clothes).we were all talking about shoes and one of the guys mentioned a pair of converse I used to have. I said I still have them, but I don't wear them coz they kill my feet. Another guy called out...
    Heellover Heellover
    36-40, M
    3 Responses Jun 22, 2013

    My First Pair Of Real High Heels

    I can still remember my 1st pair of real 'store bought' high heels. I made a few experimental attempts when I was out on my own after graduating college and working at my 1st job. I didn't try to make a shoe, more like a platform heel that I added to some cheap sandals to...
    41-45, M
    1 Response Apr 16, 2012

    I think high slender heels look really

    beautiful! Over the years I have walmed more and more in hugh heels; these days I usually wear only five or six inch heels all day and evening. Being held high so I must walk on my toes is so great. Also the needle thin heels so limit my stride as I need to balance carefully. My...
    deleted deleted
    Aug 29, 2015

    Rocky Horror Picture Show Again

    Last night I got all dolled up and went to see the show again. I went without my wife this time. I went with a group of girls and met up with some friends that I've made that are also fans of the show. Our group went by train (about 45 minute ride). I wore my latest massive high...
    Heellover Heellover
    36-40, M
    4 Responses Apr 27, 2013

    Cuban Heeled Hiking Boots

    My favorite footwear is the Cuban heeled hiking boot. They have a full 4"heel and can be worn under trouSers or with the cuffs rolled up. I walk about 3 or4 kilometer each time in a park where there are a lot of people. I wear a pair of gold hoop earrings to which I feel adds to...
    Blacksheep557 Blacksheep557
    2 Responses Dec 13, 2011

    Wearing Heels

    I have been wearing heel since college. In college one of my friends GF bet me that I could not wear a pair of heels all day. No one knew that I was a closet CD. I tried on her heels but they didn't fit so she had a friend that she thought might have a pair. So we all went to her...
    Ryan1kc Ryan1kc
    31-35, M
    2 Responses Feb 17, 2013

    I Love Heels, But Have A Solution For Those Men Who Don't

    I love wearing heels and how they make my legs look. I am actually getting better walking in them too (that took awhile) But I  do have a solution for for a man that doesn't love wearing high heels, well actually for the person that wants the unwilling man to wear them
    babybearjean babybearjean
    61-65, M
    1 Response Jun 23, 2010

    New Shoes

     I treated my self to a new pair of shoes earlier today. I was in the town center getting some other bits, so while I was there I had a look round the shoe shops. In the last shop, right up the back in the sale section, there was this seriously cute pair of mary janes. They...
    Heellover Heellover
    36-40, M
    6 Responses Jun 1, 2010

    Just One Pair

    I only have one pair of high heels, but I enjoy wearing them.I can not wear them for much more than 4 hours, but I enjoy just sitting here on the computer looking at them down on my feet.I really enjoy going downstairs and walking across the cement floor, I really enjoy hearing...
    happilymarriedguy happilymarriedguy
    51-55, M
    3 Responses Apr 22, 2012

    Wearing Heels

    I am a man who likes to wear high heel shoes. I have had this fetish since I was little. I own about 100+ pairs of high heels all with heels no less than 4 inches. My highest pair I have are 6 3/4 stiletto pumps that I bought from a local woman shoe store. Recently I have been...
    6inchstilettos 6inchstilettos
    36-40, M
    Nov 5, 2013

    I went out shopping with a female friend

    recently and I bought a gorgeous pair of heels. I stayed in a hotel when I went to visit her and loved walking around the room during the late evenings. What do you think of them.? :)
    cdlovingguy cdlovingguy
    36-40, M
    3 Responses Oct 29, 2014

    For 20 Years

    I aquired my first pair when I was 13. I don't know how many pairs I've had since but I have 3 pairs now. Every now and then I would throw out my dressing up box in a fit of I want to be normal. I wish I hadn't. I've lost some gorgeous shoes that way.
    Heellover Heellover
    36-40, M
    7 Responses Aug 5, 2009

    Well Here Goes Nothing At All

    well it happen around 5 am the other day .4 my mother was a sleep . I was awake and looking for my favorite high heel brown erth shoes sandals . there my favorite fits like a glove . I feel so sexy wearing em . Ahh what a rush it is . So I find em and go for a walk at 5 am ! Out...
    antoine15 antoine15
    26-30, M
    May 6, 2013

    I Love To Wear Heels And Black Nylons To Bed

    I rent a motel room at least once a month. I love to spend 24 hours as a woman all alone with my thoughts. My wife told me that having alone time with "me" would help me assume totally the woman I am inside. She was right. I have the greatest time of my life being dressed in my...
    louisestjohn1 louisestjohn1
    61-65, M
    7 Responses Jan 4, 2011

    It's 1am here and my friend had a craving

    for chocolate so here's how I drove her to the shop. Felt amazing even tho I didn't have the guts to go into the shop but just to be out and able to drive in these shoes felt awesome
    GirlyPyjamaLover GirlyPyjamaLover
    26-30, T
    4 Responses Jul 18, 2014

    My Husband Wearing Heels

    I love seeing my husband wearing nylons and heels. I love seeing men with nice toned or muscular legs in nylons and heels. Men just have much more toned and muscular lower bodies than many of us woman and I love how nylons cling to ever toned part on a man. It turns me on so much...
    pantiescouple pantiescouple
    Mar 1, 2013

    I Want 5 Inch Heels..but....

    Anyone have advice on how I can get some? I could order online, but my parents always view my bank statement and would see I ordered from a site i normally wouldn't, I can't drive either....I dont know any girls who wear high heels either or any who would be understand...
    hermislefthand hermislefthand
    22-25, M
    3 Responses Sep 2, 2011

    First Time

    i have always wanted high heels but they are so expensive, but recently found an online store were they were only about £25. so i bought them , just 3 inch heels ,plus some sexy stockings. they gave me such an erotic thrill i want to buy more, i thinki,m going to get some 6 inch...
    aliciasuks aliciasuks
    51-55, T
    9 Responses Apr 15, 2012

    Lover Of Highheels

    well like all others it started at a young age first my mothers shoes then my sisters always have to wear pantyhose also after mothers and sisters got to small i bought my own 4inch blk strappy sandals the several others but my favorite are my 6inch pumps and sandals from...
    36-40, M
    1 Response Oct 31, 2012

    Oops, I Did It Again...

    ...I went and bought myself another pair.I don't think my wife will be too happy. I think they're cute though.
    JosetteLaRoc JosetteLaRoc
    2 Responses Jun 9, 2012

    Surprise With Knee High Boots

    So I found that some women would tuck their phones into their tighter fitting boots as a spare pocket. Now I find that my skinny jeans aren't very comfortable to store things like keys or coins in the back pockets, so I really could do with an extra pocket. So I tried the trick...
    heelsfan heelsfan
    1 Response Feb 20, 2013

    Here's a pic of me wearing my heels.

    From the hotel room I stayed in. My phones camera was being derpy all weekend so I didn't take any other pics unfortunately.
    cdlovingguy cdlovingguy
    36-40, M
    6 Responses Oct 29, 2014

    Heels Are A Girl's Best Friend

    Forget diamonds and ludicrous junk like that that simply cost waaaaay to much money, the statement should be re-written to say that "heels should be a girl's best friend" I love my heels so much and they love me in return (at least i hope they do) i am always extremely careful...
    LucyBlack LucyBlack
    26-30, M
    4 Responses Dec 21, 2011


    As a lifelong stiletto addict one of wonders of wearing heels is how they transform me. Every pair I own gives me a completely different feeling. A few examples. Black pumps: sophisticated, gorgeous, almost unobtainable. Red pumps: a **** hungry *****. Strappy sandals: bondage...
    deleted deleted
    May 27, 2013

    How I Got Re-hooked On Wearing Female Shoes.

    While this is not a story about wearing heels, it's about wearing female sandals in general and this is how I got re-hooked too it after a break from it. So this was back when I was 17 years old, I was with a girl who was, too be honest, a big fat ****. I was at her place, in a...
    MrEvil MrEvil
    18-21, M
    Dec 22, 2011

    I used to have a small collection of high heels

    but sadly, I purged them last year. Over time, I have come to regret that decision. The siren song of clicking heels has been calling to me. Combine this with a few days of alone time, commencing tomorrow and I couldn't resist ordering a pair of heels to treat myself ! My...
    bobbieCD bobbieCD
    41-45, M
    2 Responses Jun 27, 2014
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