I Remember My First Skirt

Personal Stories, Advice, and Support 302 People

    I've always been a mini skirt lover I must have

    about 20 of them in different colours
    mischef mischef
    46-50, T
    Mar 15, 2016

    I Remember My First Skirting

    It would of been around the age of 11 1/2 or 12 while on school vacation while my siblings were otherwised engaged, I found a lovely tartan knee length tartan skirt of mommies and spend most of that morning and early afternoon in it having carefully found out when everyone was...
    deleted deleted
    Oct 13, 2012


    At school I was never into boys stuff like play-fighting, football (soccer) or any rough and tumble games you normally associate with boys. If ever I got hit by a ball I would immediately burst into tears and at seeing this boys in my class would call me a sissy, in fact, sissy...
    CorduroyBoy CorduroyBoy
    46-50, M
    4 Responses Jun 26, 2012

    Not exactly mine, but

    since I'm the only one in our house that ever wore it, that's close enough. There was a box of clothes in the hall closet that were hand-me-downs for my sister. They came from a friend of my mom's and when I was asked to come to school dressed as a girl for an end of school...
    AlbertSAT AlbertSAT
    66-70, M
    4 Responses Mar 30, 2016

    My First Skirt

    I remember my first skirt, it was a grey pinafore with knife pleats round the back and 4 buttons, 2 on each shoulder, okay so it wasn't a skirt but this year will see me hopefully come out of pnafores and into box pleats and allround pleated school skirts..mwah xxxxx
    Netballer Netballer
    1 Response Jan 4, 2012

    My First Skirt

    I remember my first skirt like it was yesterday that I bought after wearing pantyhose off & on since I was about 14/15 I thought it was time to expand my female wardrobe to more than pantyhose so I bought myself a black mini skirt & to wear along with it I bought a white top & a...
    xdpaul xdpaul
    56-60, M
    Jun 6, 2011

    My Skirt

    i bought my first skirt at the age of 15 yrs. It was a red plaid with a wide belt.Thought i was in heaven when i see all those skirts hanging on a rack.The hard part was figuring at the size
    herco565 herco565
    51-55, M
    May 29, 2009

    I never tried skirts

    when I was young, tried on moms and grandmas underware and pantyhose. One Christmas my wife bought me what she called a bath skirt made of terry cloth. I would wear it all I could, some times all day. It finally wore out, so I made a skirt from my old work jeans and wore it all...
    Frankinhose Frankinhose
    51-55, M
    1 Response Jun 8, 2015

    Mine was a simple navy blue pleated skirt.

    I wore it with a light blue blouse and and lace trimmed full slip, pastel panties, navy knee socks and saddle oxfords. I was so happy I cried.
    Bobbie1952 Bobbie1952
    61-65, M
    Apr 4, 2016

    Stylish - And All My Own!

    Grey cross-check, mid-length, warm and simply lovely ... It's funny, once I decided to actually buy a skirt and went shopping, I had a very clear idea of what was "me", as if I've always known. Yes, it was a wonderful new experience browsing the racks, checking all the...
    Fullcircle Fullcircle
    51-55, F
    1 Response Nov 13, 2010

    Sweet Pleats! Or "Beyond Just Panties"

    My first skirt was a black carwash skirt I bought at - what else - a church bazar. I had not been "dressing up" for long when I bought it. I had been contented with the "panty rush" I got from wearing panties, but after a while, I got bolder. I bought a pair of short-shorts...
    deleted deleted
    Sep 22, 2013

    My First Skirt

    hi there,Sissy Mercedes here with a snippet about my first experience in a skirt when I was a confused excited teenager discovering the unfolding joys of femininity.My Mother never found out about my secret dressing up sessions and one afternoon in particular, I spent a luxurious...
    sissymercedes sissymercedes
    2 Responses Nov 29, 2011

    Mine was at summer time home alone

    and I wore my mother's navy blue mini skirt and the feeling was like no other feeling I had before, so I took it off put on a pair of her pantyhose then put the skirt on again and felt even better, so I put on a pair of her sling back pumps and felt even better yet, then I got...
    wtbwoman wtbwoman
    46-50, T
    1 Response Mar 16, 2016

    My First Skirt

    Mine was a Cream Pleated Mini Skirt with attached brace,s and i went into the Girls toilets in town an got changed from trackie bottoms to wear it with White Ribbed Over Knee Socks - Fallen down like Legwarmers and navy blue nylon knickers, when i was 16
    stephaniegirl stephaniegirl
    41-45, T
    Oct 23, 2010

    Mine was a blue pleated miniskirt.

    .. of course I wore it with knee socks.
    schoolgyrlKaren schoolgyrlKaren
    2 Responses Nov 13, 2015

    It was a soft rayon fabric in burgundy.

    This skirt came from my moms closet. I was home alone and just had to get feminine! I went to her dresses and got a silky pair of panties. I slipped them on. Wonderful. Next came a pair of silk reflection pantyhose in gray. I felt exquisite. Then I stepped into my first skirt...
    Patriciagurl Patriciagurl
    36-40, T
    8 Responses Mar 10, 2016


    I remember my first skirt way back when I started crossdressing. It was a knee-length pleated floral skirt with white lace trim at the hem. My mom told me that the pleats can help to hide something if I get excited. I was so happy at that time because I was able to wear...
    sharinep sharinep
    26-30, T
    Jul 26, 2013

    Sure Do

    it's the one in the logo,a grey pleated school skirt!
    schoolskirt schoolskirt
    41-45, F
    10 Responses Aug 20, 2010

    It was a beautiful little double chiffon skirt

    attached to a nylon pantie with French cut leg openings. There was a split in the skirts on the left side and it looked like it was custom made to fit me. I remember that it took my mom quite a while to find just the right pair of panties to wear under my tights so that they...
    deleted deleted
    Mar 13, 2016

    I was about 13 and it was a navy gym skirt.

    I'd see it advertised in a catalogue. The girl wearing it had on a white polo shirt, navy gym skirt and white ankle socks. I already had girls white knee socks and white panties so I bought the skirt. It was so short I loved how it felt around my thighs and when worn with my...
    Kneesocks39 Kneesocks39
    46-50, M
    1 Response Oct 17, 2015

    First Skirt

    The first skirt that was really mine, rather than one borrowed from my sisters, was a brown corduroy. I remember purchasing it just before Christmas back in about 1980, it was nerve wracking going into a shop for the first time and asking for a women's skirt, I don't recall the...
    wetrev wetrev
    46-50, M
    1 Response Apr 12, 2013

    I try out my very first short miniskirts at a

    boutique in a dressing room. I was browsing only the short skirts department . ..not any others cloths or dress. Probably I have choose about 8 pieces of short skirts & walk straight into the dressing room. There's only one I love most. ..a very short mini. ..a blue demin. ..a...
    Tsgirl86 Tsgirl86
    31-35, T
    1 Response Dec 12, 2015

    Fred Perry Tennis Skirt

    The first skirt that I had for my own was a white fred perry tennis skirt that used to belong to my sister.  When she discarded it I rescued it for my growing collection of clothing.  It was a wrap-around style - with concertina style pleats aound the back and a smooth front...
    teather teather
    2 Responses Jan 12, 2012

    really was not a true skirt persay it was 1961

    and we had just got out of the 8 th grade and nana was staying with us for the first two weeks of summed helping my girl friend to learn some things and nana made us matching sun dress's and my gf was more toddler style with snaps between her legs so she could be changed easier...
    rickibrat2 rickibrat2
    61-65, M
    1 Response Mar 31, 2016

    I got my first skirt

    when I was 16, it was a mini black tube skirt and I absolutely loved matching it with some 60 denier black opaque tights :)
    deleted deleted
    4 Responses Nov 25, 2015

    It was a pleated hockey skirt.

    I'd saved up and on the way home from school went into a sports shop and said it was a skirt for my sister. I even got gym pants to go with it. It had a flat front panel with pleats around the sides and back. Side zip and a drop waist. I remember my hands shaking the first time...
    MyFeminineSide MyFeminineSide
    2 Responses Jan 18, 2016
More Stories