what was your first thing you wore when you first started to dress

[krissy]

Me my first was my little sisters panty half slip i wore that all the time even to school when we played football i was so freaked out of getting caught when they tackled me but they didnt find out . But the one thing that stands out to me the most was my moms clothes i used to sit and watch her get dressed for her dates when i was younger she wore those old style Playtex bras you know 50s style and a black full-slip she would sit there smoke a cig and do her makeup i thought she was so beautiful .then after makeup she would put on this short blue full skirt and a silk blue top and her stockings and garter belt and out the door she would go .well let me tell you when ever she worked and i was home. guess where i was You know it, right in her closet getting dressed in that outfit i felt so pretty .I remember saying to myself when i grow up im only going to wear women's clothes .its so easy when your a kid you dont have to deal with lifes complications:bighug::cute:

[Dana44]

I rember way back, it was my moms heels. LOL she caught me. wow, i was in trouble. LOL if she only knew. Mine are both gone. so that is an old memory and I like hose so I bout them first.

[BLUE ORCHID]

Hi Kissy :hugs:, For me it was also Mom's:love:Heels. >Orchid...:daydreaming:...

[Lana Mae]

Mom's panties, I think! Not really sure! I know later I tried her long leg panty girdle, nylons, and full slip! Regressed back to panties until age 65! At 65, it was full bore! LOL Hugs Lana Mae

[sherri]

That's easy -- a mini skirt! :D

[Nikki A.]

I know it was my mothers clothing but I don;t remember the first item I tried on. However I do remember wearing the old style playtex rubber long leg girdles that women in those days wore.

[DIANEF]

I had worn many items like tights, knickers,bras ect, even my sisters swimming costume. One day when the house was empty I put on my sisters dress, a really nice flowy thing and thought; yes, this is it, and it switched from being a sexual thing to something more. That was way back in 1979.

[FrannGurl]

Panties and girls jeans in the 70s. What started as a fetish, has now become a part of me and is no longer a fetish.
Its kind of nice to see for myself, how I have evolved into my female self after 40 years

[Elizabeth G]

Something of my mother's I'm sure but since it was over forty years ago I can't remember specifics.

[Teresa]

Krissy ,
Thinking back it's a toss up between my sister's full paper petticoat,or a beautiful float blue silky satin dress or a very shapely swimsuit . The swimsuit was the item that triggered it all for me , at the age of 8-9 , I didn't know my T level was that active but I found out by accident and , that was when my GD problem surfaced along with AGP . The clothes to me weren't about being a woman but wanting to be with one , that was when my tangled web started , I can't believe it's taken so long to understand all this .

[Deborah2B]

For me it was my mother's lingerie, especially the black lace stuff. It was easy to try her things on when I was home sick from school. Funny how doing that made me feel better.

[Chelsea B]

Mom’s panties. But I graduated very quickly to her girdles, which I had been fascinated by. I loved the constriction. From there, stockings, and soon after I was never going to be satisfied without being fully dressed (true to this day).sadly, her shoes weren’t close to fitting me.

[happy2cd]

I wore my sisters panties to school in kindergarten and got caught at bedtime. Later it was a full slip. For some reason my great grandmother used to use it as a blanket for my nap time (still kindergarten-1st grade) and one day while she was out I slip into the bathroom and tried that blanket on-loved it. My family had a trunk of clothes in the basement for my sisters to play dress up with and it had wedding dresses and things in it, so I dabbled in there too.

Slips and lingerie still have a lot of power.

[Jean. Ann]

My college girl friends orange mini dresss

JAS

[Piora]

I was visiting my grandparents with my mom and dad on vacation, when I was 14. There wasn't enough room in my grandparent's small house, so they arranged that I should stay with a neighbour and friend of my grandmother's a few houses away. The neighbour put me in her daughter's room, which had only recently been vacated when her daughter had got married a few weeks prior. My grandmother's friend worked, and left in the morning, leaving me alone in the house. When I peeked in the drawers of the daughter's room, I found tons of bras, panties, slips, garter belts, panty girdles and stockings, which her daughter had not yet picked up. Since I was very tall at 14, everything fit me perfectly. Of course, in those days, everything was white. So, for the next several days, I dressed in everything I could lay my hands on. No dresses or skirts....the daughter had taken those with her, sadly. I was sad when that week came to an end. That was my very first crossdressing experience, but not one that I have ever forgotten.

[sometimes_miss]

A dark blue sailor girl dress.

[Tracy Irving]

I wish I had an answer that was fun, exciting or at least different. Nope. My mother's panties.

[AngieStone]

It was pantyhose for me.

[CarynPB]

my mother's white slip....Felt so good..even at that age.

[Megan b]

It was Moms pantyhose for me as well. I was hooked from that moment on. Next to follow would be panties, then a girdles and slips and finally a bra and a dress. I just loved all these things and thought what is wrong with me but I kept on coming back to it.

[Stephanielawrence]

My first was a pair of tights that was in a drawer in my bedroom! I loved slipping into them at a very young age! I of course graduated to my moms and sister dresses, lingerie, shoes, hose, etc! Oh the memories!

[Hollibelle]

Pantyhose.

[Jaymees22]

I did dress at 7 to play one of Cinderella's ugly sisters, I think I wore a long skirt, a peasant top and a white cap. Later at 17, I wore my mother's LBD, her blonde wig and panty hose. I really felt good but didn't know what to do about it.

[Janine cd]

I'm sure it was my mom's panties and slip but I also remembering trying on her nylon hose and garterbelt and lipstick.

[Judy-Somthing]

At about 8 my sister dressed me in her Ballerina outfit that didn't fit her any more.
I remember after that I put it on when ever no one around.

[Alice_2014_B]

High heels for me.
:)

[Tania75]

My sisters clothes, and as she was shorter than me, every dress became a miniskirt, which was fine by me.
A youth group Christmas party with a crossdressing theme was the first time I was fully dressed, and both my mother and my sister helped me.
Later I moved in to a share house with two women, so I had access to both their wardrobes, which was heaven, and where the crossdressing really started.

[Cherylgyno]

Krissy. The first time I put on a pair of my mom's pantyhose, I loved it so I looked in a drawer and found a bra, I had to fill the cups so I got grapefruits from the kitchen. I went back to Mom's room and got a red rib knit body suit. I Lost track of time. I heard Mom come in the front door and got in bed wearing everything.
I was 6 year's old when that happened, now 60. I almost purged when my wife caught me about 35 years ago. My wife stopped me.

[redtea]

Panties....I'm amazed at how many people didn't start at underwear.

[NancySue]

Nylon stockings. Still #1.

[Connie.Marie]

Krissy,
My answer depends on the meaning of "..dress" in your question.

I was mesmerized by the bright red lipstick my mother wore in the early 60's. I remember that as the first thing I "dressed" in at age 8 or so. I didn't know enough to hide so Mom & Dad found out about it, gave me a quick spanking & I stayed away from it for several years.

If you really mean clothing, then it would be my mothers bras as an early teen. We were about the same size at that time and it quickly spread to wearing her skirts & tops. She wore wigs every day so it was easy to use a spare one.

Thanks for reminding us of some pleasant memories.

Hugs,

[Vintage4sarah]

My mother's nylons around 11 years old !

[AlissaMurray]

For me it was Mom's nylon body shirt. Have no idea what possessed me to put it on but once I did I was hooked. Or snapped as the case may have been.

[xdress408]

My moms nylons and slip. :D

[Lacey New]

Mother and Sisters panties, then their bras and once a slip. I did not try pantyhose until I was away in college.

[SaraLin]

One of the earliest memories I have is back when I was 4 or 5. I had stayed overnight at my grandparents' house, but they didn't have any pajamas for me (of course), so my gram improvised. She took one of her house dresses and put it on me, using a belt around my waist to hike the skirt up enough that I wouldn't trip over it.

To her, it was just a nightshirt for me.
For me, it was heaven!
Needless to say, I found lots of excuses to stay overnight after that.

If you meant where I dressed on my own - well, it was around that time that I 'liberated' some of my sister's clothes to wear at night, in bed. My mom found the clothes, and - well - I never did that again.

[Sami Brown]

I got a later start than most of you ladies. I was on a business trip to New Orleans when I was in my early twenties. I decided to go to a small lingerie shop to look for a camisole. I settled upon a nice peach colored one. Shopping for it was one of scariest things I had ever done up to that point, but the need to experiment was so strong.

[sara66]

I was 5 and found 1 if mom's bras, the quickly found my sisters underwear.
Sara

[audreyinalbany]

I guess I'm the only crossdresser ever who tried on their Mom's 1950's playtex girdle...I wanted to say latex, but it was really, like, rubber, had built in clips for holding up the stockings

[Kayliedaskope]

Panties and pantyhose from my mother's drawer. I also snitched a nightgown, but only got to wear it when the parents were not around.

[wendy]

Must've been around 5, maybe 6, I tried on my mom's panties. It felt great, compared to my own underwear, women's panties felt so smooth and delicate vs. the burlap sack feeling of boys' underwear.

I progressed to my mom's swimsuit, then her skirts/blouses/dresses. Sadly, as I grew older my mom's clothes started to fit less and less, so I started to buy my own.

[Venessa_48]

Pantyhose and a slip. I was hooked from that day forward! Then I found the power I felt the fist time I slipped into a pair of heels. Wow!

[Joanne Curl]

It was so long ago but I'm pretty sure it was my mom's longline bra, stuffed with toilet paper and dirty socks and I very soon graduated to her panties and girdle. After that it was off to the races and nothing in her closet was safe from me trying on. She had this lavender glittery caftan that she wore only a couple times that was my favorite thing to wear,especially when I'd used her makeup and one of her gray wigs. So many memories.

[josie_S]

My mom's black lace bra...she left it draped over a towel rack in her bathroom and one day, I was about 9 or 10, I saw it and slipped it on without even thinking and I was enthralled. I even put tennis balls in the cups LOL...my mom, as much as she'd hate it, was my introduction to crossdressing lol

[Stephanie47]

For me it was my mother's white nylon full slips. I was totally attracted to the feel of the fabric which was like none of the boy clothes I wore. My older brother, mother, father and I lived in a two bedroom apartment. My mother would string a clothes line down the hallway to dry clothes. The way the line was hung it was necessary to move between the hanging clothes. I would stand and caress the slips. There was also a hanging drying rack in the sole bathroom. The slips were also hung there to dry. I finally got the nerve to take them down and try them on, even wet some times. I don't remember how old I was, but, surely less than ten. After that I moved on to taking her floor length nylon nightgowns out of the laundry hamper and trying them on. There was no sexual motivation involved. If I were to go to a psychologist I truly would be able to say I really do not have a clue why I progress further. It seems it is a stretch to go from trying on a slip to end up being fully en femme, including wig and makeup.

[Bailee]

I would trade underwear with a neighbor girl when I was about six, sister's panty hose a couple of years after that.

[Laura28]

It was my moms white full slip. I can still remember like it was yesterday. I was terrified to try her bra the first time. I thought that thought it was a line I shouldn't Cross. Needless to say it only took me a couple of time with her slip and I moved to her panties and bra and then nylons and lipstick

[RenneB]

While my mom will tell the story about how when I was 4 she found me putting lip stick on in the mirror... I can only remember as far back as 5 when I was at a friends house. My mom sent me to the neighbors house where my friend a girl who was 6 was at school. I saw a pink dance tutu and had to put it on. Then while I was upstairs looking at myself in the mirror with this great dance outfit on, she called me to the top of the stairs. I hesitated but she insisted. So I walked to the top of the stairs and she said 'Oh" then "go back and get dressed in your clothes and let's go". Not another word was ever spoken about it, but I knew what I wanted...... and the rest is history.....

Renne.....

[Julie Slowinski]

My mother left a pair of strappy 3" heels in the bathroom. At that time our feet were the same size. Before that day, the idea had never occurred to me. The idea has occurred to me almost every day since.

[Becky Blue]

Mum's Bra for me

[Glendy]

At about 8 my sister dressed me in her Ballerina outfit that didn't fit her any more.
I remember after that I put it on when ever no one around.

I remember putting on my sister's baby doll night gown, back in my early teens.

[Rosemary+]

I was preschool and I tried on my grandma floral sundress and I don’t know why I did it, but I loved the feeling of it.
I still love floral dresses.

[Krea]

It was some tights (and a few other things) that my wife had put aside for me to get rid of.
They just felt sooooo great. Everything else just carried on from there.....

[NicoleScott]

Panties....I'm amazed at how many people didn't start at underwear.

Yes, well we are all different. Not only were panties not first, they were last. I dress for the image in the mirror, so I can be wearing everything feminine but what underwear I'm wearing isn't visible (my skirts are short but not that short - haha). I wear panties now. It's not that I didn't like them, I just didn't need them.
While my age was in single digits, it was lipstick and high heels that interested me. For several teen years my sister's shoes fit me perfectly, and she wore some really pretty and high heels. Actual articles of clothing finally interested me in my late teens.

[Jayne44C]

First thing I remember was a pair of my mother's black patent heels. In terms of garments, a pair of a neighbor's recycled Playtex girdles. She had put out two bags, transparent plastic, of clothing for donation. One had undergarments. I stole the undergarment bag, while walking the dog after dark and kept the two girdles. I was always a little "hippy" or wide bottomed for a teen boy. They fit great and I had them for almost six months. They had that satin front panel and hugged my so tight. I always felt guilty about the incident but, that was far outweighed by the pleasure I felt while wearing those girdles.

[Ronnica]

My mother or grandmothers pantyhose, don't remember who's but I remember having them on. I was probably 6 years old or so. I've been hooked ever since.

[Morgan lace]

My sister dressed me when I was 12.

She put me in panties & bra plus her old school uniform.
I was about to start at the same school she had left.

I got to keep it all as well afterwards. It was the start of many dressing sessions with her.:o

[Diane Smith]

My mom used to fool around and put earrings, lipstick and nail polish on me from a very early age (2-1/2 or so), but the first actual clothing I got into was her girdles and stockings. They fit OK when I was little, but I soon outgrew them, and I ruined enough of her stockings that she must have been at least somewhat suspicious. I experimented with her shoes, but most were way too small for me by the time I was old enough to appreciate them. I didn't really get into outer clothes of any kind until my great aunt gave my mom some dresses she had outgrown, and mom stored them in the basement, which was my main play area in the house. There was one purple knit dress in particular that fit me very well and looked great, and I more or less wore it to tatters over the course of a few years in my teens.

- Diane

[Cdkym]

My very first time was when a babysitter dressed me up in a sundress and some make up at about age 10. She even put some lipstick and eye shadow on me. I then played with some of my mom's makeup and bras and pantyhose.

[kayegirl]

Never wore any of my mother's clothes, but I did take every opportunity to borrow my older sister's stuff, and I still remember that very first step outside wearing one of her dresses, white knee socks and kitten heel shoes. I also have a photo taken by my Dad and I'm wearing my sister's swimming costume, I would be around 5 at the time.

[Lindaa]

For me it was a pair of my cousins panties. i must have been 8 or 9 she was the same age as me. When she showed me her panties i was so jelous they were so much prettier then mine that she gave me a pair of hers. Wasnt long after that Mom saw them poking out of the top of my jeans and flipped out. Pulled my pants down and there i stood in my panties with her yelling at me and wanting to know if i sat down to pee to. And i had to tell her yes i did. That memory has never gone away. Now this was back in say 1962 and there was none of this understanding there is now. What i got was a spanking and told not to do it again.. Well we saw how well that worked out :o

[cdinmd206]

I was probably around 7 or 8 years old and staying with my single aunt and cousin during the summer. My female cousin was a year old than me and one day we were playing dress up. My aunt suggested I wear the proper underthings and dressed me in my cousins stockings, garter belt, panties and bra. OMG I was hooked on the feeling of the nylon against my body. I sure looked forward to my annual summer stays at my aunts house. As I grew old older my aunt would have me dress as a maid and help out with the house keeping. Unfortunately she passed away when I was a teenager and I never got a chance to dress again for many years. My cousin still likes to kid me about being a maid. You should have seen the look on her face when a few years ago when I whipped out my phone and showed her a few pictures!!!

[Linda P.]

I was 13 when I read a magazine that in an earlier issue had an article on what was then called transvestism. I hadn't read that but this issue had a large number of letters they had received in response. I was struck by both the number of persons writing and particularly their fervent enthusiasm. They all just went on and on about how much they loved wearing women's clothes. It didn't make sense to me. How could simply wearing clothes produce such strong and excited reactions? Fortunately I was alone at home at the time so I decided to see for myself what all the fuss was about by putting on one of my mom's skirts. My response was instantaneous: "Oh yes, now I get it."

[BillieJoEllen]

When I actually found I had a passion for women's clothes I put on panties, bra, slip, sweater, girdle and nylons and the one item that sent me over the top (when I first became excited) was a tight skirt.

[Susan Smokes]

The first thing I put on when I dressed for the first time, was my Bra and a pair of panties.