What was the first thing you ever tried on that you can remember?

[LarrissaMurray]

For me, it was a body shirt when I was about 8 years old. It was silky and had the crotch snaps. I think my Step Mother should have just given it too me at that point because I think I wore it more in secret than she did. I was lucky enough to get away with trying on a lot of her things as I grew up, always in fear of getting caught. I know she had to have known, but she never said a word. I remember falling asleep one day in my teens dressed to the hilt under the covers. Panties, bra, blouse, skirt, everything. I wasn't expecting anyone home till late that night. My Father opened my bedroom door and said "get your butt up, it's 3 in the afternoon," and then shut the door. OMG I was never so freaked out in my life, not before or since. Then I had to undress and try to put everything back without him hearing me upstairs (it was an old house). I was never so happy to hear a lawnmower start in my life!

Just thought I'd share.

[heathr1]

A girl's blouse/top that mom bought me and asked me to wear.

[Julia_in_Pa]

A St. Louis Cardinals baseball cap.

[sierra_g]

I had just been let out of high school for the day and I was passing by WinCo. I went in, on a mission. I was going to go in, grab a leggs egg, and if anyone asked, I was buying the hose for my mom. I staked out the display a couple days before. When I got there, I didn't know there were so many types of panty hose. My emotions were excited, nervous, and turned on, plus I was confused as to which I wanted. After careful examining, I grabbed a pair of nude-full panty. I paid for them and no one asked a question or batted an eye. I was pleasantly surprised. When I got home, I locked myself in the bathroom and tried them on, only to find that my leg hair was very itchy. Luckily, we were going into November, so no reason to wear shorts. I shaved my legs for the first time a couple days later, when I had the time. The day after I shaved them, I woke up, and got ready for school. I put on my pantyhose and then my boxers, pants, socks, and shoes on over them (my secret) and went to school. No one saw. When I got home, my dad was getting ready to do wash and noticed my pants were kinda grungy and said I should throw them in. Usually in this scene, I just drop trow and go, but this time, not so much. He thought it was weird that I needed to pee before I gave them to him, but he chalked it up to cigarettes, which I was smoking and he didn't know (He actually did, but I thought I was smart). I stuffed the pantyhose behind a drawer, fought the erection I had all day from being in them, peed, pulled my boxers up, and handed him my pants.
I wore them again about a month later, but no incidents again till I was wearing them when my dad and step mom broke up and I was caught without any of my clothes and he and I were in a single motel room with a couple of Queen beds. 3 queens in that room, lol. I went into the bathroom took them off, hid them below some trash, in the can, and was nervous he would find them the entire rest of the night we were there.

[suzy1]

I lived in an old three storey house in south London.
When I was 4 years old my mum put me in the top bedroom.
There was a big box in the corner with old clothes in it and I found a silk nightdress.

I slept in it every night and when my mum came in to kiss me good night I always kept snuggled up with just my head showing above the sheets.

I remember as if it were yesterday. Have I been C.D.ing for a long time or what!

Happy memories.

[Lorenqt]

The first thing I remember trying on was pantyhose. I've been told, that I had tried on my sister's dresses. I can vaguely remember trying to walk around in my mom's shoes, as a todler.

[Antoinette]

I believe I first tried on my grandmothers heels and dresses. She's a buisness woman so most of her clothes were business attire. I was about 12 years old when I tried it.

[Kiva]

My mom's Jackie O white gloves when I was 4.

[LarrissaMurray]

Now that was the kind of story I was asking for, Thank-You so much for telling it Sierra. My heart raced as I read parts of it because of how much I can relate. 3 more posts just as I wrote this reply, Wow. Suzie, I'd have done exactly the same thing as you in that place in London at that time. I love that story too. Nylons, don't even get me started there. I believe they were the first thing I ever wore (under street clothes) as well. Years ago I think I thought spandex was a gift from above, very undetectable. "Layering up in the fall, couldn't wait! Some summers just went on forever." LOL

[tiffanyjo89]

A pair of my sister's tights...but I couldn't figure out how to get the danged things on, it was like they were something that you needed instructions, so I gave up. Later on, it'd be a pair of my sister's panties...then about a year later, my sister's panties, as many as I could try in one day.

[Simply Joslyn]

My first was a princess costume when I was five, my sister wanted to switch clothes to see what we would like in each others clothes no I wasn't a girly type of kid it just went that way go ahead laugh if need be I think its pretty funny myself, of course I also remember accidently wearing a girls skirt with the like shorts on the inside so I didn't realize till my older sister did when we entering a store that came around the same time but I remember all my first times so vividly just not the basis of time

[Julie Denier]

Mom's heels, as a youngster. Pantyhose, at maybe 10 or 12, then a dress in my early teens. Full head-to-toe en femme, about a year and a half ago.

[Jeannie]

If my memory is right it had to be a pair of my sisters panties. Mom made me wear a pair because I didn't have any clean. Thanks mom, if you could only see me now.

[RADER]

I think I was about 4 years old. I was rummaging around my mothers closet,
sited a pantie girdle with stockings still attached to the garter straps.
I tried to put them on, but it was backward. After a few attempts, I was trying
again when My mother walked in. "What are you doing"? well I was ashamed of being
caught red handed, But my mother said look, these are way to big for you, and
besides, you must take off the stockings first. She then did that and handed me the
Playtex girdle, I remember this because it smelled like rubber. I then tried it on, and
like she said, it was way to big for me.
A few years later, I could just about fit into a now pantie girdle, would sneak one and wear it to
bed at night.
At about 12 years old, I was caught again, she found a pantie girdle under the mattress; Got
a real talking to then. At 16 now, a lot more carefully, I was hiding my stash of girdles,3
long line jobs I bought at Montgomery Wards with my paper route money. I hid them in a
secret compartment I fixed up under the last drawer in my chest of drawers. I was learning
Carpentry by now and could build a lot of things in my dad's shop.
Well I do not know how she found them, but she did; More talking to and warning that I was
not normal. After I came back from the service, I got married, and started where I left off,
with you guessed it Girdles, but now I could mail order them, and I had about 25 different types.
My wife said that I was crazy, went to see a therapist. and he told m wife that I was doing no harm.
Well after 8 years, we divorced.
Now married to a real nice girl, 18+ years, who is OK with my dressing, as long as I stay in the closet.
Rader

[Jeannie]

I think it was a pair of my sisters panties and then some of my Moms undies.

[suzy1]

This is a nice thread Larrissa.

We can’t get too many of these. Glad you joined the forum girl.

Hug from, SUZY

[Cheryl T]

A striped railroad engineer's cap and shirt... hat-engineer-adult-sm-railroad-engr-9999907133.jpg


OHHHHH you mean femme things...LOL.
Well for me that was my mother's pink satin girdle with 6 garters. It was so pretty and sexy with the back lacing

[Joanna Maguire]

My mother first put me in a frilly white dress and panties I was 7yrs old.She did that on week ends and holidays and took me out in public dressed as a girl till I went to high school when I was 12. I really look like a girl in those days now long past. No one ever seem to notice I was a boy.Hated it the first few times. Then I began prefer being a girl.Somewhere in my collection there are 2 B&W pics of me and a GG both of us holding dolls ?? I had lots of dresses in the girly wardrobe But only 2 schoolboys uniforms shorts and shirts. When I left school With my first pay. I purchased a Berli Sarong Highwaisted girdle stockings and panties my self Thats when I became a CD That was in 1956 I still go out in public enfemme. My wife has know about my being A CD now for over 40 yrs. I am now retired and live as a housewife
My mother had wanted a girl baby not a boy She could not have any other children So I became her daughter Catherine when I was not at school. I became Joanna when A female workmate recognised me in the street. She was my first real girlfriend. Thats another complicated story as she also helped my wife accepting my dressing enfemme. I should have been born a girl I know that for certain Like the song I enjoy being a girl (Woman) I also have a hormone imbalance and have been diagnosed as a TS several times over the years I am now 71yrs old a woman full time. Impotent these days. So sex is no longer part of my life living As a Woman,
Joanna

[Maybelle]

1985 Nike women's light pink jogging shorts with built in panty! Instant turn on! Been going ever since.

[Frédérique]

What was the first thing you ever tried on that you can remember?

[SIZE="2"]The first thing I ever “tried on” was lipstick – I was very young at the time…

Years later I had a long shirt, actually a shirt-dress, and, since the buttons were on the wrong side, I felt very strange, yet intrigued. After that, I got into Lycra anything, enjoying the tactile feel of form-fitting fabrics as I started to dream about the impossible. From there, it was only a short jump to actual crossdressing, and I made the leap one day when my ex-girlfriend left her skirt at my house. About a week after I tried it on (which was inevitable), I had the beginnings of my femme wardrobe, gathered piece-by-piece during adventurous missions into No Man’s Land. I lived to tell the tale, thankfully, and I still wear lipstick, neatly book-ending my life (so far)…
[/SIZE]

[Being Paige]

First things that I dressed in were a bra, panty hose and a full slip.

[DonnaT]

A black velvet skirt and a white peasant blouse that had an elastic neck opening so it could be worn off shoulder, if desired. And I desired

[JaniceP]

It was a Lovely white half slip with pretty lace about 3 inches up from the hem.

I was Five and it just fit me so well-or so I thought--being Pretty is a matter of mind!

[katie_barns]

I'm going to show my age here but years ago woman wore long gloves that went to the elbows. Usually for special occasions. Mom had some that felt like silk. I loved putting them on and prancing around the house with her heels.

[Jeanna]

The first things I tried on were shoes and a skirt. I still love wearing skirts over 4o years later