First clothes worn from opposite gender

[ClaudTheBear]

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

I can relate to a lot of what you said there. After finding my sisters costumes I found all of her old leotards and would wear those too. Infact I remember color coding the days of the week and would wear that color leotard to bed to sleep in. By about age 13 my mother found my stash and threw them all out. It wasn't till I moved out on my own and found the internet that I bought my own and wore again.
Also you talked about the outfit your aunt wore for band, I can relate to that as well. Around junior high school I started seeing class mates in cheerleader uniforms. I became fascinated with those that when I got yo my junior year I joined the cheerleader team and did if for 4 seasons, fall and winter x2. Sadly I never got to find or wear a cheerleaders outfit.
Since my incontinence happened, I have tried onesies (body suits) and found them to be very similar to the old leotards and swimsuits from my past.

 

[mistysummers]

I can relate to a lot of what you said there. After finding my sisters costumes I found all of her old leotards and would wear those too. Infact I remember color coding the days of the week and would wear that color leotard to bed to sleep in. By about age 13 my mother found my stash and threw them all out. It wasn't till I moved out on my own and found the internet that I bought my own and wore again.
Also you talked about the outfit your aunt wore for band, I can relate to that as well. Around junior high school I started seeing class mates in cheerleader uniforms. I became fascinated with those that when I got yo my junior year I joined the cheerleader team and did if for 4 seasons, fall and winter x2. Sadly I never got to find or wear a cheerleaders outfit.
Since my incontinence happened, I have tried onesies (body suits) and found them to be very similar to the old leotards and swimsuits from my past.

Cheerleading really isnt a thing here but always love the uniform, when i saw the show glee and the girls had those uniforms with the fly away skirts i just had to get one, lucky for me they are easy to find on ebay

 

[BobbiSueEllen]

Cheerleading really isnt a thing here but always love the uniform, when i saw the show glee and the girls had those uniforms with the fly away skirts i just had to get one, lucky for me they are easy to find on ebay

"Rea-dy? Oh...kay!"

Pssst, there's your cue...

 

[LonelyFOX]

Cheerleading really isnt a thing here but always love the uniform, when i saw the show glee and the girls had those uniforms with the fly away skirts i just had to get one, lucky for me they are easy to find on ebay

I wear cheerleader briefs and nfinity sneakers. One of the granddaughters of the lady where I share accommodations, she practices cheerleading.
She gave me some warming up pants, briefs, shorts and two pairs of nfinity sneakers too because she doesn't need them anymore and also she gets for me some shorts, pants and sneakers from her cheerleading mates who doesn't need them anymore. They know that I'm in a precarious situation.

 

[irnub]

My first was probably trying on my sister's swimsuit once in the bathroom after swim practice. I may have tried on some kind of dress or bloomer or something forgotten in a closet at some point as well, but most of that was me being curious from a technical standpoint more than kink-related.

My first real intentional crossdressing items were a red dress and some self-adhesive bra cups to try and simulate cleavage.

 

[BobbiSueEllen]

I prefer to wear only a little frill and no lace. Which is fine since I'm only a little tomboy girl with no need for a bra...and wearing diapers . And no bold, loud shades of girl colors. Other'n that...I'm all girl!

 

[Jonethesissy1]

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

I wore a yellow sun dress with my sisters bathing suit bottom when I was 11.

 

[Jonethesissy1]

I wore a yellow sun dress with my sisters bathing suit bottom when I was 11.

 

[LonelyFOX]

Summer is coming and after trying women's ripped jeans and block heel sandals I felt more comfortable. Also I look a little bit taller in women's block heel sandals. I wear Nike wedge sneakers too because I don't want to look like a dwarf and nowadays women prefer 6'0" tall men.

 

[Jonethesissy1]

But now I have my things to wear .

 

[LonelyFOX]

I remember when I was 11 years old, when I went to bed during the winter, my mom put me on my sister's stirrup pants.

 

[BabyFee]

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

The first type of female clothing that I can recall wearing was a girly frock (not dissimilar to what are otherwise called lolita dresses). I had had an interest in nappies for some time and one day came across the concept of a Lolita dress.
Anyway, my first one arrived following a particularly stressful day at work and the sense of release I got from getting dolled up in the dress spawned the birth of my use of female clothes as a form of stress release. I now regularly wear a skirt and blouse if working from home as I find that I put less pressure in myself when wearing them.

 

[casualdiaper]

I remember when I was young and still sharing a bedroom with my sister that we switched pajamas. I remember wearing her LIttle Mermaid nightgown but after that nothing until Oct. 2014 when I started wearing panties full time.

Now I have a ton of panties and a closet full of nightgowns, sleep shirts and other lingerie. I have a few bras and dress or two though I don't try to present that is just for my private enjoyment. Though I do have some women's jeans and shirts that I have worn out in public but are not easily discernible as women's clothes.

 

[BabyHailey1977]

I still wanna kinda know if my sister knew I wore her clothes lol.

 

[Diaper44]

Lace low cut bodysuit with skinny jeans. I still

I haven’t done any, I know underwear is excluded but that is what I would try if I were to. Definitely worth trying. Just cant beat that relaxing feeling you get when your dressed. The feeling of wearing a bra is amazing. You also have a better selection of clothes to choose from and your imagination will run wild especially in the lingerie isle.

 

[SparkleBunny]

My very first time wearing a piece of clothing from the opposite sex was when i was 15 yrs. old and shopping at the mall. Me and my mom were at Aeropostale and I saw a graphic T-shirt in the boys section that I wanted to wear. It was a sideways flag with a colorful galaxy as the inside design for the flag. Later on when i was in high school i had gotten a few more graphic T-shirts as gifts (batcat and pokemon) for my closet.

 

[LonelyFOX]

On this summer I'm gonna wear women's ripped jeans. More breathable and comfy.

 

[Mickeymic]

In highschool I wore my girlfriends panties and shorts home from her house after swimming there because I didn't want to get my car seats wet. The shorts were unisex but tight and showed my panty lines, the panties had little blue flowers and frills around the waist and legs. I found the panties so comfortable I never returned them she thought they were cute and bought me more. I thought my mom (Devout Catholic would freak when she did the wash, but she didn't. Instead she bought me more. I wore them all the rest of school. I wonder what the Nuns would have done if they found out. Except for my years in Marines and a few in the Army til I got my own room. I have mostly either been commando, diapered, or in ladies panties. Styles depend on the temperature. Around the yard I have started wearing skirts I find them much more comfortable during warm weather.

 

[ClaudTheBear]

I wrote about the first time I wore. The first time I purchased my own, I was living by myself and found a Sears Catalog that had Speedo swimsuits. I had to guess on the size but did a fairly good job. I got a size 12 racer back in navy blue. That was probably my most favorite swimsuit I ever owned.

 

[CommanderCrayfish]

I'm actually wearing my first girls clothes right now, since panties don't count: I bought a pair of girls athletic shorts, since I've wanted some for a while now. Like Claud above, I had to guess on sizing, but I seem to have gotten it right on the money (a medium), and they feel great! Not nearly as tight as I thought they would be at first, and they're very breathable. Will definitely be getting more once I find some.