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 Am a Crossdresser Who Loves to Wear Girls Shorts

Personal Stories, Advice, and Support 710 People

    Locker Room Adventure

    Miss White was the 8th grade girls gym class teacher. The boys gym class was held in the other half of the gym. It was torture for the adolescent boys with raging hormones to watch the girls and their mature teacher (probably 30 years old) go through their exercises. I had...
    tecontrol tecontrol
    51-55, M
    5 Responses Apr 14, 2013

    Of Course

    I wear ladies shorts all the time. other than being shorter than mens shorts and sometimes the pockets are smaller I find they fit me better. plus knowing your wearing girls shorts over your panties adds some of the thrill for me. all womens clothing are softer and more...
    sissiegirl sissiegirl
    51-55, T
    9 Responses Jul 27, 2010

    White Mesh Shorts

    I went to the beach with my wife and she made me wear my pink and white panties under my Soffe white mesh shorts, a pink bikini top under a white spaghetti strap tank top and walk to a resteraunt about two blocks away and get food for us. It was quite embarrasing and i got a few...
    deleted deleted
    26-30
    May 28, 2011

    Love Wearing Girly Short Shorts

    I found that if I wear my short shorts to the store I get some looks. Men clearly love they ride up my butt and that my panties show through them. Women try not to look but i can tell they are appalled that I have tiny equipment that barely shows because its so small. I do hike...
    trishboy trishboy
    51-55
    2 Responses Apr 28, 2011

    Shorts

    I crossdress now and then, but I do love the way that girl shorts fit. I can get away with getting some that kind of look like they could be for girls or for guys since my wife isn't supportive of my dressing. Even so when I do go short shopping I try and find some men's shorts...
    JESSICAKNIGHT JESSICAKNIGHT
    51-55, T
    Jul 27, 2010

    Denim Shorts

    I just love the way girls jeans shorts fit!  I have several pair that I wear both when completely dressed up and in guy mode.  From the low rise style to cute designs on the back pocket, they are just too cute!
    denisegurl2 denisegurl2
    46-50, T
    3 Responses Mar 8, 2010

    Wear It Regardless

    idc what i'm wearing i'll wear girl shorts no matter what!
    BS1993 BS1993
    18-21, M
    May 1, 2011

    I Wear Short Shorts

    I visited my local Goodwill Store a month ago. It was a rewarding experience as I found a nice pair of denim short shorts. They are nice and short and very tight. The girls look so nice in theirs. I look and feel just as sexy as the girls do. Have been wearing them often and...
    kfsteve kfsteve
    61-65, M
    2 Responses Jun 7, 2010

    I Like To Wear Girls Shorts, But Feel Too Self Concious.

    I look good in them, I lke the little pockets, belt loops, decorations. Right now I prefer cut-off mens shorts or men's very short shorts, because of the way they fit in the crotch. I have a couple of mens pairs like that. 1" - 2" inseam. Around here, I feel very self concious...
    gypsylover gypsylover
    51-55
    Apr 20, 2011

    I Wear Girls Shorts

    I love to wear girls shorts. This past summer when I was home I wore girls shorts just about every day.  They are much more fun to wear than guy's shorts.They pair well with clogs or flats.I love to shop for girls shorts and try them on at the store.  Not that it's  fall I'm...
    jml2000 jml2000
    61-65, M
    3 Responses Nov 1, 2012

    I am alone here at Chennai.

    searching cross dresser at chennai
    bablisharma bablisharma
    41-45, T
    Apr 20

    I Love Wearing Them In Public

    i disregard The W signal on the tag, and buy any shorts i deem cute. My most favorete whcih comes in every girly color known to man, is nike tempo short shorts, i just love them. so much i wear em almost every where, i love going shopping in short shorts, (note, i dont loke...
    norwegianguygirl norwegianguygirl
    18-21, M
    5 Responses Apr 25, 2010

    Jean Shorts

    I like to wear women's clothing and usualyy enjoy skirts and dresses. But a week or so ago, I tried on those tight jean shorts. And with them dark black tights. This made me feel more sexual than I imagined it might. I went on to a web cam with them.
    mandyoh mandyoh
    41-45, T
    Nov 23, 2009

    I like wearing girls shorts, and **********

    I really do. I like wearing them and ************ with them. i like any kinds of girls shorts.  denim, cuffed ones with side buttons, twill shorts, cotton.  striped ones from the 90s are hot.    I enjoy especially tight short ones with butt pockets.  That's just sexy as...
    wilbur78 wilbur78
    31-35
    Jan 1, 2013

    I Love The Look Of Womans Shorts And Slacks

    I love to wear woman’s shorts. They fit better and shape my rear in such a way that the rear seam cups my cheeks. If I wear a thong, it is even more noticeable. Some of my shorts, and woman’s slacks, have no rear pockets, which allows my panty line to show, or more...
    kayes60 kayes60
    70+, T
    3 Responses Mar 1, 2013

    How Else Should You Dress To Relax?

    I love to wear a pair that's one size smaller(elastic waist of course). It's comfortable, snug (love when it ride up), shows alot of leg (smooth of course) and just feels sexy.
    deleted deleted
    26-30
    2 Responses Nov 27, 2009

    I love wearing very short girls shorts over a

    nice pair of silky panties.
    timothysknickers timothysknickers
    26-30, M
    May 17, 2014

    Caught In My White Mesh Shorts

    I am feeling a little embarrassed because i was walking on a trail this morning wearing a cute little pair of pink panties under my Soffe white mesh shorts with just a hint of my *** showing when this city truck with four men came up to do work on the trail. they were giving me...
    deleted deleted
    26-30
    3 Responses Jun 8, 2011

    Wearing Women's Shorts

    I love the short denim daisy duke look. Women have alot more options when it comes to "crossdressing". My wife wears men's jeans and shirts and I wear womens jeans, panties, and short shorts. She says the men's jeans fit better and she likes the baggy kind of look. I shave my...
    michelleats michelleats
    56-60, F
    1 Response Sep 19, 2010

    As with all male verses female,

    with me the female wins hands down. There are so many different lengths, colors styles and texture of fabric. Pair the shorts with a matching jacket and you have a classy suit, jacket off a leisure summer look. Tank or tee great relaxed look. The combinations are endless.
    CdKimmi CdKimmi
    66-70, M
    2 Responses Apr 24, 2014

    Heck Yes

    If it's females clothes it is in my wardrobe. You won't catch me wearing long baggy men's shorts.
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    Nov 1, 2012

    Short Shorts

    When i shave and soak in a comfy bubble bath i just feel so gurly. Each week i prepare for this ritual. i always start with a fresh blade (never use the inferior disposables) . i gather the other supplies i will need: a feminine scented shaving cream, an aloe based lotion for...
    redlace redlace
    61-65, M
    Jul 4, 2010

    Short Shorts

    I like to wear short shorts just like the girls wear. Mine are girl's shorts. I get them at thrift stores and always search for the absolute shortest ones they have. I like to wear them with my strappy high heel sandals. They are very sexy and I feel great in them.
    kfsteve kfsteve
    61-65, M
    5 Responses Sep 12, 2013

    Shorts

    I love wearing girls shorts. I wear volleyball shorts, and junior shorts. I do have some denim short shorts, i would love to wear out some day. In the fall i buy my shorts, i get them on clearence, it turns me on looking in the womens clothes section, then going to the cashier...
    bikermeat bikermeat
    46-50, M
    2 Responses Nov 7, 2011

    I Had Sex With My Girl Wearing A Shorts Romper

    i like having sex with my girl while she's wearing shorts. i don't get to have it as often as I like. but when I do, I sure cherish it. I got her a pair of black cotton romper shorts with zip up front. i made her wear it with no underwear. she didn't like it, but I loved it. I...
    wilbur78 wilbur78
    31-35
    1 Response Jan 1, 2013

    I am so sad that the thrift stores here in the

    north country are removing their inventory of girl's cutoffs and short shorts from their racks for the winter. Judging by all the incredibly sexy ones I saw being worn this summer, there should be a great crop of them on the racks next spring. I guess I will have to make my own...
    wet2wet wet2wet
    51-55
    9 Responses Sep 13, 2014

    Short And Tight

    I fully agree that the best way to get a short tight fit is to go for girl's shorts. I prefer ones without rear pockets, prefer the smooth line. And they're usually tight enough so that just wearing them is a turn on. I have several friends who can't keep their hands off them and...
    shortshorts shortshorts
    36-40, M
    6 Responses Sep 29, 2011

    They Are All I Have

    I never liked the baggy guys shorts. A number of years ago I got up the courage to buy a pair of ladies blue jeans shorts and loved the feeling and the look. Since then my shorts collection has grown to include those with color and more girlish style. Nobody minds and now I I do...
    0hBrandie 0hBrandie
    41-45, M
    2 Responses Apr 4, 2013

    Once You Get Used To Wearing Them, Girls Shorts Are A Must, Inside Or Out.

    I now have a collection of girls shorts, and shirts, all of which I am really happy to wear either around the house or when I go to town, even visiting my sister. All as a str8 older man. My favorites, the white nautical shorts with a big wide belt. My black girls shorts look...
    Moddle Moddle
    66-70, M
    2 Responses Mar 22, 2011

    Girls Shorts

    i am a crossdresser who loves to wear girls shorts they display my shaved legs and tight *** so well!i tuck my sissyclitty when in tight girlshorts so there is no unsightly look t the front of my shorts!!
    mandiejune mandiejune
    51-55, M
    Jun 5, 2010

    Love My Women's Shorts

    I like women's sports shorts for those times I'm busy in the house or working outside. They're coolish on hot days & the colors are so much more vivid than the bland choices of men's shorts. I like longer shorts (dress or casual) when out in the public.  A nice pair of...
    janusatv janusatv
    61-65, T
    Jun 28, 2010

    Cheerleader Shorts

    When i was in high school in the early 80's i was in class their was a pair of cheerleader shorts with our school logo on them left under my desk by one of the prettiest cheerleaders at my school. When class let out i picked those shorts up in between my books. I took them home...
    deleted deleted
    26-30
    2 Responses Jun 6, 2011

    Love To Dress With Wife

    I have become a girl, and a **** at that. I am straight when not dressed and bi when dressed. I have met with many men and have really enjoyed it. Meeting with men is so much easier. No strings, just pleasure. When I was younger I started to wear women’s panties and loved them...
    pantiescouple pantiescouple
    26-30
    Jul 19, 2010

    Panties Are So Cool

    Yes some nice silk panties next to my skin makes my day lovely ,
    buyitnow buyitnow
    66-70
    1 Response Apr 22, 2011

    I have 6 pair of girl short shorts

    and I love then all. One pair isn't denim but the rest are. I wear them in public and so far no-one has said anything to me, but I've had a few weird looks, don't care. Love them.
    irieone irieone
    41-45, M
    1 Response Feb 21
More Stories