This experience may contain mature content, as flagged by the community.
Please click away if you do not want to see this content.
To report inappropriate content, please email us.

I Love Wearing Skirts, Stockings And High Heels

Personal Stories, Advice, and Support 1,171 People

    I love wearing either a skirt

    and blouse or a dress with stocking and my 4 inch high heel shoes. This is my attire for work.
    femaleatthelake femaleatthelake
    41-45, F
    7 Responses Jun 11, 2015

    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
    1 Response Jun 9, 2012


    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

    Being Feminized

    mickjag mickjag
    66-70, T
    1 Response Sep 3, 2013

    Being Dressed So Good

    just can't wait until  i get home from wok or weekends so i can wear skirt,stockings and high heels and get fully dressed!!!just love the feel of hose on my shaved legs and panties over my saved public area which often results in my sissyclitty getting hard!!! its the feel...
    mandiejune mandiejune
    51-55, M
    Feb 12, 2010

    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

    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
    4 Responses Nov 28, 2009


    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

    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
    56-60, M
    2 Responses Dec 26, 2009

    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
    70+, F
    Dec 18, 2010

    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...
    deleted deleted
    Sep 20, 2012

    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
    Aug 6, 2013
    janetjanet janetjanet
    51-55, T
    Dec 10, 2015

    Wearing For Cds

    Wearing skirts and stockings with high heels are the core of Crossdressing , it is a joy and fun to wear around the house .....It make me feel as a woman a lovely wanted one ....
    lilianne lilianne
    46-50, M
    2 Responses Dec 25, 2009

    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
    2 Responses Aug 14, 2013

    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
    1 Response Jan 26, 2012

    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

    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
    2 Responses May 27, 2013

    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, M
    3 Responses Jan 1, 2011

    My Long Cd Life

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

    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

    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
    4 Responses Jun 20, 2011

    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
    1 Response Feb 17, 2012

    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
    66-70, F
    23 Responses Nov 24, 2011

    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
    26-30, F
    5 Responses May 17, 2014

    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
    1 Response Jun 18, 2013

    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
    1 Response Jul 20, 2010

    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


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

    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

    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
    8 Responses May 5, 2014

    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

    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
    3 Responses Apr 7, 2012

    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
    2 Responses Apr 25, 2013


    i love wearing stocking and suspenders and mini skirts and exposing my self to others iw anyt to go out dressed as a slutty crossdresser
    aliciasuks aliciasuks
    51-55, T
    1 Response Feb 24, 2010
More Stories