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.
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.....
"The only way is onward. There is no turning back."
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.
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.
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.
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.
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
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.
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.
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
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!!!
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."
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.
The first thing I put on when I dressed for the first time, was my Bra and a pair of panties.