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I Love Wearing Skirts, Stockings And High Heels

Personal Stories, Advice, and Support 1,145 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 7 Responses Apr 25, 2011

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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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    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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    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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    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 11 Responses Jun 9, 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Related Experiences

    During an orchestra concert, we were told to wear a black top and a black bottom but the teacher did not tell us whether or not we could wear tights so I wore a tight black Tshirt...
    conniejiang98 conniejiang98 16-17, F 1 Response Jun 28

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    I am extremely into to my woman when she wears her skirts, stockings, and high heels. I find it very sexy and turns me on in the worst way to wear I have to ravish her and satisfy...
    cassiescowboy cassiescowboy 26-30, M 2 Responses Jul 13

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    I absolutely love when a women with legs and a hot body that wears high heels. It just something about high heels that makes a women's sex appeal go up. I love the way it makes...
    HTAD HTAD 18-21, M 3 Responses Jun 25

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    I to love high heels. Especially platforms. Thanks to an understanding wife that realizes they are just a piece of footwear, has allowed me to to enjoy my heels. I am not at the...
    bnchmrk bnchmrk 46-50, M 1 Response 4 days ago

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    I have always liked wearing high heels even when I was a child. As I got older I was told I must not wear them, as they are for girls. I had to wear them secretly. After searching...
    hh4evry1 hh4evry1 36-40, M 4 Responses Jul 14

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    My wife and I were shopping and a lady walked by in short skirt and high heels my wife said she didn't know how they could wear heels all day. I said it wouldn't be that bad...
    pmgurl pmgurl 51-55 2 Responses 4 days ago

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    Ather a long absence im wearing my high heels i absolutely love them i miss thsoe heels
    Highheels23 Highheels23 22-25, M 1 day ago

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    Love making love women just wearing sexy high heels
    hotty35 hotty35 31-35, M Jul 14

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    I love Christian Louboutin's shoes and boots. I have two pairs. Absolutely love wearing them.
    hh4evry1 hh4evry1 36-40, M 8 Responses 4 days ago

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    Love my high heels. Feel so very sexy in them. Always get a thrill shopping for them.
    susiecdgurl susiecdgurl 56-60, T 3 Responses Jul 10

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    I also love to wear high heels
    boytoy66 boytoy66 46-50, T 5 Responses Jul 14

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    It's weird but I just feel pretty I guess when I wear them. When I go ago shopping I usually try on some high heeled shoe. This pic was obviously to small though :) lol
    thatgirlluvsred thatgirlluvsred 13-15, F 1 Response 3 hrs ago

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    Swimming in HeelsYesterday while the wife was at work, I have been going through some of my oldest hiding spots of clothing and shoes and have been getting rid of the things that...
    jamie50 jamie50 51-55 3 Responses Jul 4

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    Cleaning Out the Closet I have been cross dressing for many many years and have acquired a collection big enough to fill a walk in closet. Some of the items I have date all the way...
    jamie50 jamie50 51-55 5 Responses Jul 3

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