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I Love Wearing Skirts, Stockings And High Heels

Personal Stories, Advice, and Support 1,152 People

    I Wish I Could Do This All The Time

    I love my high heels very much. I very so sexy an d pretty with how they make my legs look when I'm wearing them around my house with my tights and skirt. I hope one day to wear them around outside like to go for a walk or something. I'm praying that I'll get to dress on...
    glasscitycd90 glasscitycd90 22-25 Sep 20, 2012

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    My First Time Out

    I went out the first time dressed in my 6 inches Steve Madden heels. I wore a nice tight pencil skirt with a blouse and a waist corset over my blouse .. I had a lot of guys hitting on me and staring at me . I loved every minute of it . I wore my heels for 10 hours straight . I...
    lovelyjoann42 lovelyjoann42 36-40 1 Response Feb 17, 2012

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    The Works

    There is something so nice about dressing in a panty girdle, suspenders and stockings. The tautness feels great and is amplified with each step. Add to this a pretty skirt and real high heels and it only gets better. It makes me walk like a woman and enjoy every step and turn...
    MyFeminineSide MyFeminineSide 41-45 1 Response Aug 14, 2013

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    Caveat Emptor

    I never buy my "high" heels too much higher than medium high. Too High, Toes Hurt :(
    eleanorssong eleanorssong 56-60, F 1 Response Mar 21, 2012

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    Stockings And Short Mini Skirt

    I really love to put a  gartrerbelt and stockings a mini skirt 4 inch heels and go shopping for cloths makes me feel so sexy when i try something on,love to check out the ckerks too mmmmmm
    maninagarterbelt maninagarterbelt 41-45, M 4 Responses Nov 16, 2009

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    Wearing Skirts, Stockings And High Heels Really Turn Me On

    The first time I saw myself dressed like a woman I knew I was a mistake. I had shaved my whole body and smelled like a flower freshly plucked. I put this incredible cream all over my body and started to dress. First went on the panties, soft and black lace. Then the black...
    louisestjohn1 louisestjohn1 61-65, M 4 Responses Nov 17, 2010

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    When I Was Just A Child

    I have never wrote or told anyone, the truth of what happened,, when i was but a child,  where to start  I was a growing boy full of life never thinking that any one person could do, or try changing, a little boy, into a little girl to please there own ego, the mans...
    4ujolynn 4ujolynn 51-55, M 2 Responses Dec 26, 2009

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    Being Feminized

    I LOVE BEING FEMINIZED BY WOMAN , AND WEARING SKIRTS, PANTYS, GIRDLES, STOCKINGS AND HEELS,, I MAKES ME SO HORNY.
    mickjag mickjag 66-70, M 1 Response Sep 3, 2013

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    Evening Wear For A ****

    Over the last 3 or 4 years my Wife/Mistress has become more dominant. At first i just wore a CB, but over time this has progressed. Now, when we are alone in the evenings, I have to wear a short floaty skirt, a pair of hold ups and a pair of 4" pink heels. As a devoted slave/sex...
    Slaveofmisty Slaveofmisty 46-50 3 Responses Jan 1, 2011

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    Every Day Now

    For the last two weeks I have been able to dress 24/7 in women's clothes. Typically I wear pencil skirts. They are tight fitting and show off my legs very nicely. Yesterday after working at the computer for a few hours I stood up and straighten my skirt, I thought to myself how...
    jilliank jilliank 51-55, M 2 Responses Jun 18, 2013

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    A Far Better Way To Dress

    It is a far sexier way to dress, I have worn skirts and dresses for years now with stockings and heels and as I am 5'10" I have a lot of leg showing even although I never wear mini skirts now.Men and Women do notice, men stare, women give a knowing look.It is a far better way to...
    pamela8 pamela8 61-65, F 24 Responses Nov 24, 2011

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    I love dressing up, especially in black

    stockings, garter, tall black boots. Sometime a thong (or no knickers.) Plus a nice corset which let's my voluptuous breasts bulge out of the top. I just love feeling SO sexy.
    encamino67 encamino67 46-50, F 9 Responses May 5

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    Foolish Taboo

    I cannot fathom why women have allowed the wearing of sheer nylon stockings to be a fashion taboo! I refuse to follow such a nonsensical dictate. Little is more pleasing to me than to slip on a new pair of ultra-sheer nylon stockings after shaving and creaming my long legs. The...
    Lanainluv Lanainluv 26-30, F 6 Responses Apr 7, 2012

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    Skirts, Dresses And Slips

    Not a Story-Sorry---------I just have to ask, DON'T you just TOTALLY wearing cute Girl Clothes-Lingerie, Foundation Garments, stockings attached to the Garters of either a Girdle or GarterBelt, through skirts, dresses and heels--I like the 2 1/2" Pumps--easy to walk in. Be...
    carolannP carolannP 61-65, M Mar 16, 2011

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    Every Chance I Get

    ...and it's getting to be more often.My wife accepts that I do; so long as I keep it in the house (apt).She's away for the weekend. So, early this morning, I took the opportunity to venture out.I took the dog for a walk across the grounds. There are 5 buildings in the complex...
    JosetteLaRoc JosetteLaRoc 36-40 1 Response Jun 9, 2012

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    Pretty Ruffles

    OMG yes! I just adore wearing FEMININE skirts, RHT Stockings, ( I most ALWAYS Wear a Girdle with garters to hold up my Stockings, I find this quite Girly and FEMININE), cute blouse and lovely heels. I have just found and bought the cutest Skirt, I just adore it. It has a...
    carolannP carolannP 61-65, M 2 Responses Mar 1, 2011

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    My Long Cd Life

    been dressing asa female since i was a young boy..mom helped in my teens and now im and older man who loves dressing as a woman classy and conservative.love pantyhose heels makeup the works.  i go out often with no problem and just cant describe the feeling whenim all pretty in...
    margie4 margie4 46-50 Dec 30, 2010

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    My First Time Mother Dressed Me As A Girl

    My 8th birthday was the first time mother completely dressed me, and although it was so long ago I do remember my first dress was a light blue party dress. Being that I was young and challenged, with Cerebral Palsy that I had since birth, mom usually got me dressed. That birthday...
    betty3100 betty3100 51-55, T 3 Responses Feb 18, 2011

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    My Latest Kink

    I always wear stockings with my heels and usually a short skirt. Firstly for the feeling, slowly pulling on my stockings then slipping on, strapping, buckling or zipping my shoes or boots is like foreplay for me. Secondly because I so much enjoy matching the skirt and stockings...
    deleted deleted 26-30 3 Responses May 27, 2013

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    Wearing Heels And Skirts

    I love the feel of the wind gently blowing my mini skirt against my stockings as I walk in my 3 inch heels, while fully made up and presenting as a woman. I love the feel of stockings rather than pantyhose,as they feel more sexy too,especially when connected to suspenders on a...
    Georginamilnes50 Georginamilnes50 56-60, T 3 Responses Jun 20, 2011

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    This is a story about my new heels. The stockings and skirt I wore with them were a matching outfit.

    So yesterday during lunch I had to go out to run some errands. I had to go to the Post Office, and pick up some other items to take home after work. Since I was out, I stopped at the nearby Burlington Coat Factory to browse the clearance shoes and lingerie. Although I had no...
    deleted deleted 26-30 1 Response Jan 26, 2012

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    Legs

    I've long legs, it suits me, i like the smart look. Not black stockings with white stiletto's though, a bad combination. White with black is much better.
    AtomicWater AtomicWater 41-45, F 3 Responses Jun 11, 2010

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    Love Wearing

    I love the feel and the way it makes my legs look in this type of clothing nothing better
    CeeWade CeeWade 36-40 1 Response Feb 2, 2013

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    Cause

    It makes me feel GOOD! It makes me feel feminine. It makes me feel sexy. Men like it!!!                   
    Josie06 Josie06 56-60, F 8 Responses Oct 20, 2009

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    Me To

    i love wearing dresses and skirts and stockings they are so damn comfy and soft i love how dresses and skirtsd are loose from your body
    addguy3455 addguy3455 18-21, M 1 Response Oct 24, 2011

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    Exposing Whats Under My Skirt

    I have been cross dressing for many years now and the thrill of going out is incredible. I love to drive up next to a big rig truck and show my short dress, thigh highs, and panties. I often go by a major truck stop, park along the side of the road, and wait until a truck slowly...
    pantiescouple pantiescouple 26-30 1 Response Jul 20, 2010

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    First Time Out In Public

    True story. As I sat in my car I looked down at myself. I was wearing a short black skirt with lace around the edges. A black lace top through which you could see my bright blue bra. And thigh high stockings. So many times I had pull up to the bar before, only to chicken out...
    ForcedSissyGurl ForcedSissyGurl 31-35, M 10 Responses Mar 6, 2012

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    Garterbelts And Nylons Are Soooo Hot To Wear

    I absolutely love the feeling of putting on a sexy lacy garterbelt and then sitting down (on my plush pink fur cushioned stool with no panties on yet) and slowly sliding my jet black nylons over my freshly shaved sikly smooth legs prior to standing up al clipping them in place...
    SissyGena SissyGena 31-35, T 5 Responses Nov 28, 2009

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    Fitness Expert Andrea Metcalf Describes Three Simple Steps To Avoid Foot Pain Without Forsaking The Joy Of Wearing Heels.

    Don't we all love the way a woman's legs look in a dress with a great pair of high heels? I know I do and enjoy wearing the myself and wanting to look great doing so. Creaing a longer line, great calve's curve and sleek appearance. Luv it! Andrea Metcalf article 'My Aching Feet...
    Josie06 Josie06 56-60, F 1 Response Nov 16, 2010

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    Acceptance

    My wife of 15 years and I split up over a year ago. At the time she said one of the things she couldn't deal with was my wearing skirts, heels and hose. I told her when we first started dating and at the time she was ok with it. She moved out and we had little contact for the...
    Highheelsman Highheelsman 41-45, M 10 Responses Jun 9, 2013

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    Escatsy

    let me put on skirts and stockings and heels and i am there. i love it
    tiffani2009 tiffani2009 61-65 1 Response Oct 7, 2011

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    New Mini Skirts

    my new mini skirts arrived and mmmm the seller added some shiny pantyhose as i freshly shaven i couldnt wait. so i picked out my sexy 4 inch heels and dressed slowly and sensually raising my hosed leg as i slipped my pantyhose on mmmm each leg more exciting then the next mmmmmm i...
    sexyinhosesharon sexyinhosesharon 41-45, M 8 Responses Apr 25, 2011

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    I Love Wearing My Stockings.

    i have never loved more than anything less than wearing my girdles and my stockings and of course my dresses and high heels.
    phylisanne phylisanne 66-70, F Dec 18, 2010

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    Sometimes at weekends I like to wear a short

    flared mini skirt about 5" above the knee, pink silk knickers,hold up stockings and high heels.
    janeseymour janeseymour 22-25, F 6 Responses May 17

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    When I Dress Like This I Tend To Get Horny And Act Slutty.

    I commute an hour one way to work, so there are many times where I stop about half way to see if I can get any action. Most times I stop an exit before the cruizing turnoff and change in a gas station bathroom.I take off my male clothes and put on my stockings and panties and a...
    sissyskoolgurlatgmailcom sissyskoolgurlatgmailcom 46-50 Aug 6, 2013

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    Wife Caught Out By My Stockings..

    My ex wife knew of, was happy with and even encouraged my dressing up. One day I was dressed in a silky blouse, matching silky and lacy bra and panties, a camisole, skirt and high heels. Normally I would be wearing pantyhose but that day I had decided to wear suspenders and...
    SusanMarina SusanMarina 26-30 3 Responses Apr 25, 2013

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    Oh To Be In Them

    I love getting dressed in nice skirts with pantyhose and my 3 inch heels. I feel more like a lady in them. Hearing the click of my heels as I walk and feeling the stiffness of my caves with each step give me a sexy feeling. I feel like this was how I was supposed to be. It feels...
    Adam59 Adam59 56-60, M 1 Response Mar 4, 2013

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    Related Experiences

    I was on a business trip out of town last week and had the chance to do a little shopping. I found a cute pair of Wedge Sandals at Target and purchased them. My flight home was...
    jamie50 jamie50 51-55 1 Response Aug 17

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    I'm 28 and started out wearing high heels@ about nine every chance I could enjoy strutting in them
    whitwhit86 whitwhit86 26-30, M Jul 31

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    Back in high school I would wear shorts on the winter but I'm excited for this winter to stop wearing shorts and start wearing skirts! Also I usually hate winter and the snow but I...
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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    I find a girl wearing high heels such an absolute turn on
    Mustangkid2016 Mustangkid2016 22-25, M 4 Responses Aug 8

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    I love wearing hose and high heels when I am dressed, semi dressed, or nude.
    tammylynne tammylynne 41-45, F 14 Responses Aug 10

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    I love wearing high heels wherever I go and I don't understand why other girls look at me and say nasty things. Are they jealous or do they just think casual is the way forward...
    Abbierose93 Abbierose93 18-21, F 12 Responses 4 days ago

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    I'm straight, aged 37, and I have always loved high heels, ever since I can remember. Other than nylon ankle socks for some pairs, I don't cross-dress. It's just about the shoes...
    JayGovernor JayGovernor 36-40, M 6 Responses Aug 9

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    I love high heels, I wonder if it's because being a dancer I am use to being on my toes and feet arched. I love to clean in heels too, maybe I am just weird. I have a friend...
    Chicgeekgal Chicgeekgal 22-25, F 2 Responses Aug 18

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    My biggest question is why would you want where High Heels, its probably most redundant designed article, and many reaserch show it can easily destory your feet http://www...
    gypa gypa 26-30, M 1 Response Aug 7

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    This is such a turn on when a woman work's hard at work all day and her high heels are smelly and sweaty mmm
    Renayde92 Renayde92 22-25, M 4 days ago

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    Any one want to talk about high heels message me or add me
    Disturbedheels Disturbedheels 26-30, M 4 Responses 4 days ago

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    Just in from the pub, left early so I could enjoy wearing some stockings etc. Girls, you don't know how good you have it?! Imagine being able to wear what you want with no...
    susspender susspender 41-45, M 3 Responses Aug 15

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    The place to myself, basque, stockings & heels. What more can a guy want 💋👠
    susspender susspender 41-45, M 1 Response 4 days ago

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    I went to work earlier and took over from a lady colleague. She was going to a wedding so I asked if she had a new outfit to wear. She had. It's a blues dress. I asked if she would...
    hh4evry1 hh4evry1 36-40, M 2 Responses Aug 16

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