Firsts

[transfeminate]

This is my third attempt to post this. I lost the previous two when I tried to submit. Let's hope third time lucky works.
I cam across this photo the other day and in it I am wearing the first 'girl' piece of clothing I ever wore. It is a leather mini skirt that my wife dug out from her closet when we both discovered we liked me as a woman it occurred to me this might be an interesting topic of discussion, every-ones first time , what they wore and how did it make them feel.
In a similar vein, there was an earlier post on what made us feel most feminine and lipstick came top, so I thought I'd add mine. Although lipstick is a big favorite, my number one is thigh highs. I just love the feel of pulling on mine258814

[Liz57]

I'm with you, I love the feeling of nylons on my legs and the constant pressure where they're stuck to your thighs. But...the feel of garter belt straps running down your thighs, delish!

I don't wear lipstick often so yeah, stockings.

Liz57:battingeyelashes:

[docrobbysherry]

The first thing I ever tried on was a pair of women's jeans. I was in my 50's. They made such an impression on me, I didn't try on anything else fem for a year!:heehee:

[lingerieLiz]

Other than panties my mom had me wear. The first thing that I tried on and wore was my mother's sun dress.

[Jennie2]

A little blue full slip, when I was about 8 years old.
The best sensation ever was putting stockings on for the first time, what a feeling on your legs.
The one thing that makes me feel most feminine is wearing a sexy bra

[ZO e]

I remember my first time I was 7 my sisters dressed me up. I was hooked of course it fun for they did not know what they started.I loved the way the fabric's felt

[Beverley Sims]

One of my firsts was being dressed as a baby girl when I was five.

All in frilly baby dresses etc.

The best part I remember was being taken down the street in the pram.

Yep! It was a great ride.

[SheriM]

I cant remember the first time. I was probably 4 or 5 and pulled on my mothers girdle. I do know that the girdle was the first piece of clothing that I was drawn to and shortly thereafter the nylon stockings.

[cdterri]

My first item was a little blue dress around the age of 5. No idea why!

[Jennifer in CO]

as stated in other posts, I have seen pictures of when I was very young (2, 3, 4, etc) in this or that of my sisters but remember none of it. First time I kinda remember was a movie from Christmas when I was 7 or 8 in which Sis and I came into the living room to see what Santa left and we're both in long flannel gowns. Movie stops and next frame I'm wearing a long dark blue robe that covered all the gown, all except the bottom 3-4 inches of ruffle. First time I remember enjoying wearing girls clothes I was 10. Spent 3 weeks with my Aunt/cousins and all I had to wear was 10 year old girl cousins clothes...including her bikini (its a looong story). First time I wore girls clothes and they didn't "feel" like girls clothes...as in they felt "right"...was when I was 15 and spent the whole summer with my Grand parents and the above mentioned Aunt as Jennifer. First time I found out girls clothes could be erotic was when my girlfriend (now Wife) found out I wore girls clothe. That if she "kept" me in them long enough I got about 1/2 as horny as she was if she kept playing with me, so needless to say she "kept" me dressed as often as she could. That particular "first" was when we left our wedding...in matching lace yoked blouses and red pants with matching trousseau's underneath...and flew to NO so dressed (another looong story)....

lots of firsts...

[Tracii G]

Great pic and I'm glad you finally posted it.
My first time dressed I was 17 by my then GF and her sisters. I loved it.
I had really long hair so they rolled it and put make up on me,some of my GF's clothes and we walked around the neighborhood.Loved that too.
My GF's Mom thought it was a hoot and suggested I go to the prom which I did as well a few weeks later.

[Diversity]

As best as I can recall, my first was putting on my mother's panties and bra. The second for me was her stockings followed by her garter belt.
All this was in my pre-teen years. Of course it wasn't long before all were donned at the same session, one afternoon, after school, before anyone came home.
Di

[transfeminate]

Wonderful collection of replies everyone. Thank you all

[Liz57]

I was thinking I couldn't remember my first time but now that I think on it, it was almost certainly in 6th grade. Our school had several fund raisers for the annual sixth grade trip to Silver Springs. One was a beauty contest where the girls dressed the boys up as girls and we were in a pageant. I guess technically a lot of people have seen me cross dressed but I don't think that counts. I do think that's probably why I like to cross dress because a bashful, rather homely, insecure adolescent got all prettied up and people made a fuss over me and I won one of the categories as well. (That was to be expected since my dad and my partners mom were both teachers in the sixth grade) I've often wondered if any of the other boys likes to cross dress now. Our local high school has a similar contest to raise funds for project graduation and I've wondered if any of those boys like to dress now. It was scary how pretty a couple of them were. One of my sons-in-law was in that contest and I wonder about him. Maybe one day I'll get the chance to ask him. Definitely have to bring some of this up when coming out to my as an explanation to her.

Liz57:battingeyelashes: