I Love Wearing Pencil Skirts

For all those whom love wearing the best item of clothing - pencil skirts 776 People

    Me Too

    After reading the stories I have come to the realization that although I prefer dresses over skirts I also like pencil skirts. In fact the types of dresses that I look for are the types with pencil skirt type bottoms. I really love that confining feel and look. I guess is the...
    57Peggy 57Peggy
    56-60, M
    Mar 14, 2012

    Afraid Of Them At First

    I am a transitioning MtF person. I could never wear them until the last 6 months or so. I, thanks to my hormone therapy, now have enough curves in the hips and butt to actually wear them and look decent in them. Now I can't enough of pencil skirts! I love them, so feminine...
    Melissa89 Melissa89
    26-30, T
    2 Responses May 20, 2013

    Check out this fashion blog Pretty dope

    chanelconoco.tumblr.com also chanelsconoco.blogspot.com Instagram chanelconoco
    someoneforyou12 someoneforyou12
    22-25, F
    Mar 22, 2015

    Pencil Skirt

    im a 23 year old crossdresser and while i know that this is mostly for women, i just wanted to share my love for pencil skirts. i am a straight 23 year old male and i love wearing pencil skirts. im very athletic and again straight, however i love endulging in my feminine side. i...
    str8cd88 str8cd88
    1 Response Feb 25, 2012

    My Favaroute Skirt Too

    Love to wear pencil skirts as well infact got my favaroute black one on now.
    frieda123 frieda123
    31-35, F
    1 Response Aug 12, 2012
    cotygal123 cotygal123
    16-17, F
    1 Response Jun 23, 2014

    I Absolutely Luv Them

    To me they are so feminine! They are also very professional for office attire, a beautiful secretary look.  They remind me of how women use to look, guess I'm a bit old fashioned. I think that can be slimming and give a more shapely sillohoute when worn with a nice...
    Josie06 Josie06
    56-60, F
    2 Responses Apr 27, 2010

    Enhancing The Feminine Form

    I love pencil skirts. Being a transvestite means finding women's clothing that can flatter your figure. Guys do not have nice full hips like women, so a pencil skirt is perfect article of clothing for the crossdresser. I like the skirt to have a nice high waist, suitable for...
    BizSuitStacy BizSuitStacy
    56-60, T
    1 Response Jan 1, 2012

    A Little Old Fashioned

    I may be a little old fashioned but I feel a woman should wear skirts and dresses. Now I may not always do that but most of the time especially when I am working I wear a skirt or dress and pencil skirts are my absolute favorite. A pencil skirt, nice blouse, and high heels make...
    Kelli1409 Kelli1409
    36-40, F
    8 Responses Jan 15, 2013

    I Am Sorry To Say I Forgot About Mine

    I have a couple of pencil skirts in my wardrobe.  I tend to wear more flowing or bohemian skirts typically but enjoy wearing the pencil skirts when the mood hits me. As others have said, they do a good job of showing your curves, especially hips & bottom.  I have a...
    lezfemme lezfemme
    51-55, F
    2 Responses May 20, 2010

    I Love My New Ann Taylor Pencil Skirt

    I just LOVE my new Ann Taylor pencil skirt (light gray) and teal ruffled blouse- it is adorable! I found some 3" court shoes in gray that work perfectly! I'm such a girl!
    sissie5470 sissie5470
    14 Responses Mar 20, 2010

    Sharpening The Point

    My bigger aside has always liked the secretarial look and to me nothing does it better than a lined pencil skirt with a slit at the back for ease of movement.It looks so classy with tights and a plain blouse.I currently have two such skirts.
    deleted deleted
    2 Responses Dec 7, 2012

    Pencil Skirt Love

    I really like wearing pencil skirts, especially with buttons on the slit so I can wear them a little tighter than normal. Also leather pencil skirts are really nice too. Tight is always better especially as it highlights my bottom and forces me to take smaller more feminine steps...
    MyFeminineSide MyFeminineSide
    2 Responses Aug 16, 2013

    Working From Home

    Nothing says office wear to me more than a nice pencil skirt. So, today, as I am working at home, I decided to pull out my grey pencil skirt - matched it with a grey ruffled blouse. Underneath I am wearing a beige lace bra and panty set with a brown Victoria's Secret garter and...
    scaff69 scaff69
    2 Responses Aug 25, 2011

    Pencil Skirts

    I absolutely love wearing pencil skirts, so comfortable around your waist and legs unlike trousers and the material feel so nice.  Everyone should wear them.
    deleted deleted
    3 Responses Mar 16, 2010

    Yes I Do

    I am not sure why but when I watch tv and channel surf always wind up watching the Kardashians, House Hunters, Ice Road Truckers. There is something voyeuristic to watching these shows. The Kardashians are just to weird for this world. House Hunters is almost like a real life...
    josycd josycd
    51-55, T
    2 Responses Feb 25, 2012


    I'm quite tall so they seem to suit me very well, particularly with stiletto heels, i've a black one, another black one and a black one.
    AtomicWater AtomicWater
    41-45, F
    4 Responses Sep 15, 2010

    My Favorite

    My pencil skirts are absolutely my favorites.I love to wear them as often as I can. I love the way they hug my hips, ***, and thighs. I don't think I have enough of them.
    JosetteLaRoc JosetteLaRoc
    Jan 11, 2013

    Me Too

    After reading these stories about pencil skirts I realize these are the types of dresses I look for with that type of bottom. I have always preferred single piece dresses for their ease of quick removal if need be (1 piece versus 2.) I guess that the reason that I have stayed...
    57Peggy 57Peggy
    56-60, M
    2 Responses Mar 14, 2012

    I've not had much experience of it,

    but it's a potent image for me 💋💋
    1LikeMind 1LikeMind
    51-55, M
    Mar 11, 2016

    Yes I Do

    Pencil skirts are one of those inventions that panders so beautifully to the female form. The pencil fits like a glove, displays the *** perfectly and promotes the feminine walk better than any other item of clothing. Now, I don't quite have the requisite *** to pour into a...
    DonnaSt DonnaSt
    66-70, M
    7 Responses Nov 6, 2011

    I am thinking about wearing a blue jean pencil

    skirt on a road trip from SD to DEGA in 2weeks it takes us 18 hrs to do the trip. It would be three of us my 40 year old son and his girl friend I think they would be cool about it the good thing if they are not I could change. I will keep you posted
    jerbare jerbare
    61-65, M
    3 Responses Apr 20, 2015

    Oh how i love Pencil Skirts!

    ! the feeling of the material hugging tight to my body. I love how they make me feel almost trapped in them. i love to wear a tight fitting stretch top with them to.
    deleted deleted
    May 9, 2015

    Figure Hugging Pencil Skirt.

    Nothing more sexy then putting on a tight pencil skirt. I always wear high heels with this type of skirt and it give me a delicious feminine wiggle when I walk.
    deleted deleted
    7 Responses Jul 13, 2013

    Last Night

    Last night, I was a little more bold than ever.I ventured to one of the local RedBox sites wearing one of my pencil skirts; I love them. It's one that is outside one of the local Walgreen's stores. It also happens to be facing one of the towns main streets.Granted it was about 1...
    JosetteLaRoc JosetteLaRoc
    1 Response Feb 15, 2013

    My Favourite Skirts!!!

    pencil skirts turned me on to wearing skirts after years slobbing around in jeans. I found myself in a job where girls couldnt wear trousers and to my surprise found i loved the way I felt in a skirt - professional for work, but softer and more feminine.. I still feel that skirts...
    carolyn25 carolyn25
    22-25, F
    1 Response Feb 25, 2013

    I DONT MYSELF but I would love to hear about

    if any of you girls on here like pooping your panties with a pencil skirt on over the top or if you have had a experience of that weather it was a accident or on purpose I would love to honestly know!
    Mushypanties12 Mushypanties12
    18-21, M
    Mar 22, 2015

    Time For House Work

    Its another Sunday morning. So I showered and shaved my legs.. put on a nice black pencil skirt from Newport News, suntan hose and a sleeveless turtleneck and cardigan. The pencil skirt really shows off my butt and well the leggs are smooth and shiney... I need to catch up on...
    jilliank jilliank
    51-55, M
    1 Response May 16, 2010


    I like pencil skirts very much.  They are flattering and sexy and draw attention to a womanly shape.  I have a couple and are among my favourite things to wear.  When I wear a pencil skirt with high shoes and sheer stockings it makes me feel really good.  A...
    womaninbliss womaninbliss
    51-55, F
    3 Responses Mar 17, 2010

    All-time Favorite

    I just love to wear a snug fitting black pencil skirt with a white satin blouse.  I think this is the most feminine outfit in my wardrobe. When wearing this skirt it is always with a very firm HiWaisted OBG that has boning and satin panels. Also wear a firm and boned...
    BrigitteB BrigitteB
    66-70, T
    1 Response Aug 22, 2012

    Sexy Yet Understated!

    I love this kind of skirt and  find it to be one of the most versatile pieces in my professional wardrobe. Although I still struggle with being a "bbw," I am happy to have been blessed with a round booty and few things show it off more than a snug skirt! I feel...
    choctawgrrrl choctawgrrrl
    41-45, F
    10 Responses Sep 15, 2010
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