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

[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.

[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