First clothes worn from opposite gender

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mistysummers

Transage little sissy who want to marry Fluttershy
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Photo of school dress
So just wondering what was the first item of clothing you crossdressed in, underwear is excluded for this, as imo its a cheap answer that most crossdressers would put down as 1st clothes. So only outerwear.
For me i did get hand me downs from older sister, ie shirts and shorts, pretty much gender netural stuff with some exceptions, but the first thing i can say i wore, that was a girls was a red gingham school girl uniform dress when i was 13
 
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The first thing I wore was a long sleeved bodysuit that clasped at the crotch, and a skirt. They belonged to my sister. It was an amazing feeling until I looked in the mirror. What I saw didn’t match my mind.
 
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I put on a lace bodysuit of my girlfriend's when I was like 18 and wore lingerie quite often after but proper outerwear is a crazy story.

I was at a place in life where I could burst into tears at any time, just the slightest thing, I was tense, desperate. I snapped on a lunch break went and bought a dress and some flat ladies shoes, changed in the toilets and wore it back to my car. Boy hair, facial hair the lot. People pointed and laughed but nothing bad happened, the rest is history. 15 years later and I'm happy and healthy.

Still not had the confidence to wear a dress and no make up in public again 😂
 
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First clothes I have worn from the opposite gender are panties. I love panties and diapers on my wife, or wearing them myself. In particular, shiny ones and ruffled ones are my favorite.
 
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I am not a cross dresser but when I was in 2nd or 3rd grade, one of my friends had a surprise birthday party and everyone had to come in a costume. Well, this was back in early 70's so the stores didn't really carry things like they do now, so my mom and my sister made me up as a little girl. I was full on in a dress makeup and all. No one at the party knew who I was and because of that I won the best costume award. It was a fun time and no one even teased me about it afterwards.
 
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I think for me it was a skirt, then a nightie.
 
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Grendale said:
First clothes I have worn from the opposite gender are panties. I love panties and diapers on my wife, or wearing them myself. In particular, shiny ones and ruffled ones are my favorite.
Please read the op in full as the question did exculde panties as its a typical answer
 
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Pantyhose are the first and only for me, still only very occasionally. I love the sensual feel of my legs and feet being completely encased like the skin around a sausage.
 
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DippyDawg said:
Pantyhose are the first and only for me, still only very occasionally. I love the sensual feel of my legs and feet being completely encased like the skin around a sausage.
Strange reference. Me likey!
 
Yessir, that's my baby...


And for some reason, Misty, your avatar (when small on my phone) sends my mind instantly to an image of Isabella from Phineas and Ferb. No idea why... :unsure:
 
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I figure why not share. For me, I was about 7 and I found my sisters old costumes when she was taking dance. It was a white dress that had the brief part made as part of the outfit. It was kind of like a leotard with a sown on tutu. It has some sequences on it and a big image of a rose over the front. The skirt part was just barely long enough to cover the crotch area and it also had a lace part under the skirt like a petticoat.
I would stand on the edge of the tub and look at myself in the mirror.

Ballet-Tutu-Child-Pink-Rose-Professional-Tutu-Ballet-Dance-Costumes-Girls-Ballerina-Party-Panc...jpg
Very similar to this.
 
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For me it was a cousin's leotard
 
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I don't remember the exact color/type but it was my mother's dress.
 
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I haven’t done any, I know underwear is excluded but that is what I would try if I were to.
 
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I suppose this kind of counts as cross dressing...around age 12, I kept stealing my older brother's shirts and would pretty much refuse to wear anything else. (Mostly they were shirts he had grown out of anyway, so he didn't really care.) I hit puberty really early so while my classmates were still in the early stages of it, at that age my body was pretty much fully grown with all the annoying curves that come with it. Since I didn't connect well with most girls in my class anyway, that led me to trying to hide my body and reject everything feminine - I cut my hair, refused to wear makeup, and wore the aforementioned shirts that were not flattering in the slightest.
I still like to shop in the men's section when it comes to comfortable clothes like hoodies and long sleeve shirts, but I think I have a much healthier attitude towards it now.
 
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For me it was my sisters Navy blue wrap around netball skirt.
Loved it so much I now have several.
 
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SashaNicole said:
For me it was my sisters Navy blue wrap around netball skirt.
Loved it so much I now have several.
Ive worn them afew times as my sister did netball, you do see girls wear them any more, they were kinda a casual wear for kids in the 90s and even a part of some public schools uniform. Now netballer wear the bodysuits which i kinda want to try on
 
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Due to precarious situation, I'm sleeping in a nightie and stirrup pants, I'm wearing women's ripped jeans with block heel sandals or ballerina flats. I feel barefooted but my feet feel relaxed after work. I wear steel toe boots and when I tried those ballerina flats they were so light and comfy.
 
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When I was in elementary school I would watch my High School aged aunt practice her baton in the back yard every day and envy her cute, shiny majorette costumes. I found one of her old elementary school costumes from when she first started out and tried it on one day. When she caught me, she just laughed, put makeup on me to match and when none of the adults were around, she let me wear it while she taught me to twirl her smaller batons. Eventually we got caught. No one got in trouble but I was told to leave her old costumes alone. I was the "good kid" (yeah... right.. if only they knew! <g>) so I did what I was told.

She did let me have the bloomers though and I kept them for the year it took me to outgrow them. Wore them to school a couple times a week.

The theater department at the tiny parochial High School I went to provided costumes for our productions and most of the time the base for the costumes came from the girls section of the catalogs. We had 3 boys in the theater class and 15 girls so they just bought all girls parts of the costumes except the specifically male character clothing. I quite often forgot to turn in things like tights, leotards, unitards, etc... cost my parents a fortune over those 3 years.

If my grandmother (she raised me) were still around today, I doubt she'd be surprised to see me living as a girl (or woman if necessary... adulting.. blehhh.. we hates it precious...). I suspect she knew I was Tabby long before I did.

Tabby
 
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