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]

:heehee: 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... 178419


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?

The first thing I ever “tried on” was lipstick – I was very young at the time… :o

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)…
:battingeyelashes:

[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 :)

[Beth Mays]

My mom also start dressing me when I was about 7 or so. Dresses, hose, ribbon in my hair.. even some shoes too.
As I grew older it was pantyhose that I wanted the most.

[Barbara Ella]

Ah yes...mom's bra. Put a towel on my head, and the shadow on the bathroom wall looked so feminine. 8 years old.

Barbara

[xdressed]

My mum's bra when I was 14. Don't even know why, didn't think at the time I wanted to be a crossdresser or anything, just thought it would be funny even though I was on my own. How things change ^_^

[Aloha Jayne]

Roman soldier uniform. I've told this story on here before, so I appologize if you've heard it. I was in a school passion play with my best friend in first grade. We played the two roman soldiers that cast lots for Jesus' robes. Our moms made the costumes which was tin foil over cardboard for the breast armor, and basically a royal blue dress with a pleated skirt for the rest of it. google a picture of a roman soldier to see what I mean. So after the play, I beggggggged my mom to let me wear the roman soldier costume. Finally one summer day she gave in at my grandmother's house. I went out and played football, and climbed trees and did regular boy stuff,,,,,,,,but in a dress! The postman even called me girly. It was wonderful. Always dreamed of getting to wear the pretty dresses that the girls wore in school without anyone knowing I was really a boy underneath.

[jennifer1958]

My sister's green panties when I was 14; 39 years ago.

Jennifer

[Anne2345]

I remember when I was five years old, I snuck into my little sister's room to try on some of her clothes. Somehow, I knew I would get in trouble if I got caught, but I simply could not help myself.

The problem, though, was that I was much too big to properly fit in her clothes. Regardless, I was on a mission, and nothing was going to stop me. Nothing, that is, except getting stuck in my sister's shirt. Although I did manage to get it on, I could not get it back off. I was stuck. I tried and tried and tried to take it off, but to no avail.

In the end, I had to ask my mother for help removing the shirt. I started to cry, and attempted (in vain) to think of a story, any story, that would help get me out of my predicament. Whatever story I came up with (I do not recall the story), my mother did not buy. I was given a stern lecture on how inappropriate and wrong it was to wear my sister's clothing, and I was punished and spanked.

I did not recognize it at the time, but that day began a chain of events that would ultimately lead me deep, deep into the closet for the next three decades of my life. As well intentioned as she was, I wonder if my life would have been any different had my mother instead held me tight, told me everything would be all right, and that it was ok to be different from the other kids . . . .

[Carrie Ines]

About 10, its was my mums wedding dress, she's quite small, fitted amazingly, i was hooked after that x

[ELIZABETH46]

about 7 or younger, with my oldest sister as an acomplice.
Her skirts and panties got my heart speeding for more.
and more was as time went.

[Sarah-J]

I don't have an interesting tale nor do I recall my exact age, but... it was around the age when I was discovering that girls weren't so "icky" after all. I tried on my mom's bra from the hamper for no other reason than curiosity. I definitely liked it but didn't really like that I liked it (that whole 'social conditioning' thing, yaknow--boys just don't do that!) Fast forward about 30 or so years without the idea of dressing in anything feminine ever once crossing my mind... until a few years ago. And here I am. :)

[LoriFlores]

One day I was left at home by myself. I don't remember how old I was, somewear around 7 or 8, and I had always admired girls clothing. I suddenly realized the moment was mine. I raced upstairs to my sister's bedroom and after a quick search located her pink satin tutu that I had always especially liked. I undressed and slipped into it, found myself in heaven, and the rest is history...

[Diane Smith]

I was very, very young (less than five), so my memory is a little fuzzy on the sequence of things, but it was either my mom's high heels, or her girdles and stockings. I found out quickly that her shoes didn't fit me well at all, so I actually didn't disturb them very frequently. But I was into her lingerie drawer almost every time she left the house for more than a minute or two. She must have known about it (I wasn't that good at getting things put back exactly right, and I know I damaged several of her stockings), but pretended not to notice.

- Diane

[cindyc6]

I was either 5 or 6 and my 2 girl cousins were visiting my family. They where about 8 and 10 respectively and my aunt had bought them bikinis. All I remember is that i was strangely drawn to them. I waited until they went out and i ran to the room they were staying at in our house and i put the bikini on. It was love at first sight.

[aly01]

:battingeyelashes: I think it was a pair of my sisters panties or pantyhose. it felt and stills does feel oh so heavenly, to wear female clothes.

[Alice]

My older sister's gymnastics leotard when I was about seven years old. My older brother was the only one home at the time and he was playing video games in his room. I remember quietly sneaking past his room to get to my parent's bathroom to see if I could find anything of my mother's, but I was too afraid and went back into my sister's room. Prior to that I do vaguely remember being engrossed in my mother and sister painting their nails, and my mother let me paint mine with clear nail polish. After that nothing for about five years.

[Jacqueline Winona]

Mom's pantyhose, I fell in love at first sight. Then, I don't know what was next, a bra of my cousins, a leotard of another relative, or a girdle from yet another.

[eire emma]

My sister's red and black mini kilt and black tights,absolutely loved them, then they got thrown out, Damn!

[sometimes_miss]

Let's see; the first thing I remember was one of my sister's 'hand me down' dresses when I was a toddler, mom supposedly had me wearing them so I wouldn't ruin my 'good boy' clothes. Suuuuuure, and she also put off getting my hair cut to save money too (but managed to spend plenty on my sister's clothes, haircuts, and of course, new furniture).
The first thing someone else had me wear was his sister's sailor girl dress.
The first thing I tried on on my own, was my sister's old panties that she had grown out of.

[PretzelGirl]

Although I consider myself a late bloomer, I did go through about a 3 month period in my teens trying things on. How all of you can remember what was first exceeds my ability to remember. I do remember the favorites. A top of my sisters that was elastic and gathered throughout the body and the sleeves were chiffon. A dress my mother made for my sister as she competed in a lace queen contest. The dress of course, was pink and very lacy. The odd one was a halter gown stored in the basement. I later took a girl to a movie as my first ever date and then to a prom. She wore the exact dress that was in my basement. So I have a picture of her and I at the prom and along with remembering our good time, I get the visual to remember the dress.

[phylisanne]

my mothers stockings.

[Nicole76]

My sisters white mini skirt and white ballet flats. What a great feeling!!:)

[alinne_lima]

The first thing I ever tried was my mother panties, but I can´t remember with what age

[Bobbie S]

Aunts panties 4 0r 5 years old.

[JillyNylonz]

My Mother's Hanes reinforced sheer (415's) flat knit stockings and her pantygirdles at about age nine in 1959. Then slipping into her crocodile stilettos and I was hooked forever and a day !

[sue1965]

My older sister's black lace bra and matching panties....

[Didi]

My sister's stockings and girdle.

[Miriam-J]

My sister's halter-top dress. Sure was great back in those days when the hair was on top of the head rather than the chest and legs.

[Stephanie47]

My mother use to hang dry her nylon slips in the bathroom. Slips were my first feminine attire. I love slips, slips and more slips.

[RachelDenise]

I remember trying on one of my mother's bras. I was about 11 or so and then it was a girdle, pantyhose and a longline bra.ried her lipstick. Soon after, I began to get my own things.

[Sarah C.]

My mother use to hang dry her nylon slips in the bathroom. Slips were my first feminine attire. I love slips, slips and more slips.

I'm with you Stephanie! Slips were the first things I ever tried (as best as I can remember anyways!). My mom had quite the collection of nylon slips, and I'd sneak into her room to wear them as often as I could. I always tried to put them back exactly as I found them, but I'm pretty sure she knew that something was going on.

Love to hear these kind of stories - keep sharing everyone!

[Nahed]

The first thing I tried on was my mother Nylon nightgown

i felt like i'm in heaven ,i remember my age was 15 year old , i start sneaking to my mother bedroom every weekend when the house empty and trying on all mom lingerie

it's a good days

thank you for bring that up sister

[Brenda2246]

The first things I remember trying on was my sister's pantyhose! I have my own now! Smile

[Annie M]

First thing was the whole thing mom's panties, bra, slip, skirt, top and heels as I remember I was about 8, I got caught! But she didnt get real upset just helped me straighten things out and put on the make up. Mom always wanted a girl and I was happy to oblige! Dad was gone alot!

[PrettyPolly]

my sisters school dress and pantyhose, sheer black, i was about 12

[madcitycdph]

When I was really young, 4 or 5, my Grandma would let me where her knee high stockings. I also remember trying my mom's pantyhose on once about that age. I didn't start again until about age 12, and that was with my mom's pantyhose.

[Brittany CD]

I think it was a nurse halloween outfit, or maybe it was a bra

[silkiehosewearer]

The 1st thing I ever tried on was my mom's pantyhose. I was 10 yrs old, I don't even know why i wanted 2. Curiousity I guess. I remember sneaking into my mom's bedroom and found her pantyhose on the floor almost under the bed. I picked them up & went into the bathroom and slipt them on. Oh what a rush I got. I just looked at my legs for a bit but my trunks back on and went out into the living room and watched tv for a bit. Making sure the tv was quiet as I didn't want my mom or sis to hear me. After a bit i decided to take them off before they got up. I slipt them off and put them back in my mom's room on the floor. I was so scared as I thought she was going to catch me and say "what are u doing? And why do you have my pantyhose ?" After which I went back into the living room and watched a bit more tv and then went back to sleep a little while longer. Thinking of my mom's pantyhose and wanting to wear them again.

[erickka]

Spiky stiletto heels and stockings. That was such a rush at 6 or 7 years old!