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

I Am a Crossdresser Who Loves to Wear Girls Shorts

Personal Stories, Advice, and Support 696 People

    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

    Your Response

    Cancel

    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...
    Brandie1960 Brandie1960 41-45, M 1 Response Apr 4, 2013

    Your Response

    Cancel

    Womens Short

    Love womens shorts.  My SO and I go working on walking trails, love to be seen in my short shorts.
    ginawr ginawr 70+, T 4 Responses Feb 18, 2011

    Your Response

    Cancel

    Wear It Regardless

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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Pop On Those Girls Shorts

    I'm more your TS adult little girl really but anyway amongst the wonderful world of the frillies and frocks there's always been a space for wearing the sort of shorts girls wear.For one thing as much as I adore dresses and skirts, sometimes shorts can be more practical for say...
    Joanne0chan Joanne0chan 31-35 May 2, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Bed Time

    I always wear ladies velvet dance style shorts in bed...
    manosamt manosamt 51-55, M Mar 7, 2011

    Your Response

    Cancel

    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 4 Responses Apr 28, 2011

    Your Response

    Cancel

    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 3 Responses Nov 27, 2009

    Your Response

    Cancel

    My Sensitive **** In Girls Shorts Or Mini Skirts

    Wearing girls shorts with no underwear feels sooo good against my ****. It turns me on to look at myself in the mirror, and it really turns me on to watch women stare at my **** in public. The ultimate rush is to wear a **** ring in girls shorts because the constriction of the...
    nrock nrock 31-35, M 1 Response Dec 5, 2012

    Your Response

    Cancel

    Im starting a Ki.K group chat ANY full time

    cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like their outfit of the days or stories of getting caught or telling people or going out in public in clothes. if you want to join. Ki.kme fhnvs86...
    lovevspink16 lovevspink16 18-21 Apr 5

    Your Response

    Cancel

    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 3 Responses Nov 7, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    At The Gym

    I lover wearing girls shorts, but I only really get to do it at the gym.  NAturally the shorts are snug and short, and when I wear them you can make out my vpl.  If I wear my white shorts you can really see my knickers through them.  Sometimes I wear an all in one...
    pantylover5099 pantylover5099 36-40, M 7 Responses Jan 5, 2010

    Your Response

    Cancel

    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 56-60, M 3 Responses Nov 1, 2012

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Apr 14, 2013

    Your Response

    Cancel

    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 31-35, M 8 Responses Sep 29, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 4 Responses Mar 1, 2013

    Your Response

    Cancel

    I Love Girls Shorts!

    I love to wear womens shorts. I love to wear them out. It's the only time I actually cross-dress out in the public. It turns me on, showing off my ***, and legs! When I first put them on, my **** starts to grow. I love the way they slide up the crack of my ***, It just gives me...
    w2bdonna w2bdonna 51-55, M 4 Responses Dec 8, 2010

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 11 Responses Jul 27, 2010

    Your Response

    Cancel

    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 1 Response May 28, 2011

    Your Response

    Cancel

    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 61-65 2 Responses Mar 22, 2011

    Your Response

    Cancel

    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 1 Response Apr 20, 2011

    Your Response

    Cancel

    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 61-65, M 4 hrs ago

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    My Wife's Shorts

     i love to wear my wife's shorts around the house they are short and denim and they are a bit tight on me but that's so hot i love to wear them with a pair of pantyhose my favorite at the moment is denim shorts and fishnet pantyhose and a huge hard on its so nice.
    jarviscooper jarviscooper 36-40, M 5 Responses Jul 3, 2009

    Your Response

    Cancel

    Why Not , They Feel So Right

    Girls shorts are all i own. They fit and look alot better than mens shorts. I like short-short cut-offs the best . I wore one pair so often,my wife loved me in them, they fell apart. I don't fully dress as a girl in the summer , but i sometimes wear shiny tights or pantyhose...
    cindyloulove cindyloulove 56-60, M 3 Responses Feb 20, 2011

    Your Response

    Cancel

    Related Experiences

    Every since I was in 4th grade I'd occasionally go into my sister's (who's 3.5 years older than me) bathroom to wear her underwear and (training) bras. Then when I was older in...
    BlackHedgehog24 BlackHedgehog24 16-17, M 3 Responses Apr 5

    Your Response

    Cancel
    If I'm not wearing diapers I'm in my bra, and panties!!
    sexual445 sexual445 26-30, M 3 Responses Mar 31

    Your Response

    Cancel
    I just love wearing thongs so much <3 it's the best
    ThinkDiff ThinkDiff 18-21, M 2 Responses Apr 5

    Your Response

    Cancel
    My girlfriend had a Ann summers party few weeks ago her cuz came to it. She is really hot... she ordered some butterfly panties. To night my girlfriend went to bed so I got them...
    24chris24 24chris24 22-25, M 5 Responses 6 days ago

    Your Response

    Cancel
    Today I have the whole house to myself with no one it! So I get to dress up like a girl completely! just uploaded more pics go check them out!
    mrman77 mrman77 22-25, M 4 Responses Apr 4

    Your Response

    Cancel
    The last two days I have been looking for a Swimsuit, seen a nice one today online, now going to the shop....
    amber8642 amber8642 51-55 4 Responses Mar 29

    Your Response

    Cancel
    I just had sex with a guy while I was dressed as a woman
    ray205 ray205 46-50, M 5 Responses Apr 4

    Your Response

    Cancel
    I've been told they suit me. I just like hats :3
    TwdFireflyy TwdFireflyy 16-17, F 6 days ago

    Your Response

    Cancel
    I am a chick who loves sports! I am big time into sports! For football I love the New England Patriots. For baseball, I love the Boston Red Sox. For College Basketball, I love...
    NYSlilAngel NYSlilAngel 26-30, F 4 Responses Mar 30

    Your Response

    Cancel
    There's nothing hotter than a woman who loves baseball. It's so sexy seeing a woman in a baseball jersey, cap and stirrups.
    dub000 dub000 26-30, M Apr 15

    Your Response

    Cancel
    I love woman in uniforms and would like to find woman who enjoy wearing uniforms
    kevefc kevefc 46-50, M 5 days ago

    Your Response

    Cancel
    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

    Your Response

    Cancel
    I love all women but I'm convinced that I personally are more equally yoked with white girls. I know that some white girls are just dating blacks cuz their rebelling against racist...
    TennesseeMandingo TennesseeMandingo 31-35, M 5 Responses Mar 24

    Your Response

    Cancel
    I dont know if this post is still working, but I want/need to share my story. I was married to a guy who was a psycho when I was not even 18. Coming from India, thats like a death...
    kindredspirit75 kindredspirit75 36-40, F 1 Response Apr 5

    Your Response

    Cancel
    At first I didn't like wearing boys underwear (I'm a nudist so I only have to wear these when I go outside) because they suffocate, cram my privates so I started to wear girl...
    TheGrandPoobah TheGrandPoobah 13-15, M Apr 10

    Your Response

    Cancel
    Love dresses! 💜 I grew up in a family mostly of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since...
    sissyyumi sissyyumi 22-25, M 6 Responses Apr 11