I have always known I was transgender for as long as I can remember, I would fashion my own skirts and dresses out of whatever I could find, in only the way a toddler could. Whilst my dad was very transphobic (this was the start of the seventies) and would make extremely hateful comments, mum was more enlightened and actually bought me some girl's knickers and girl's trousers when I was about seven years old.
Abigail.
When I don't count few times He tried His mom's bra and panties, when he was in early teens and just fooling around I went all in few weeks ago. I ordered all the basic of wardrobe from underwear and bras to t-shirts and skirts. And then I found out my black knee-long summer dress looks AWESOME when wearing with His white shirt that's knotted under my breasts.
at age 11, panties & bras from my mother.. the feeling never got lost I then had to steal form other female relatives/friends but then it was very hard to keep them hidden.
Early teens or a bit before
I know I tried on my sisters and mom?s stuff early on. But it was in early college days that I bought my first pair of panties, a vivid recollection. They were made to look like denim and actually had a zipper up the front. I had to have them and bought them at Treasure Island. Owned by JC Penney?s and long gone now. They eventually got tossed in a guilt purge, but I remember it took me a huge amount of strength to step into that checkout line back then.
Later I stole a pair of pantyhose at a department store I worked at. I would never steal anything, but wanted them so bad. To this day I have thought about sending them the $1.25 to pay for them. Unfortunately after 50 years they were driven out by Walmart. I hope the good Lord can forgive a young guy driven by this desire and society?s negative guidelines.
I tried on my mom's bra when I was like 10. But I don't think I tried on panties until I was like 12-13. No sisters, so all I could try on was my mom's clothes. But every now and again one of my girl cousins would stay with us for a while or I would stay with them and I loved the selection more because they were sexier than what my mom would choose
After almost a year of just lipstick, One day, at age 13 or so, I had the opportunity when I was home alone so I just decided, to go "Whole Hog" with my mom's stuff in the laundry basket, and a slip and house dress hanging on the back of the bathroom door. Panties, Girdle, hose, bra, slip and dress, along with the makeup. It all actually fit well (just a little bit loose). And that was the routine from then on.
I used to wear panties to my first to junior School. So about 7 or 8. Though I had played dress up with my, all girl, cousins long before then. Bra would be about 13 or 14.
Panties at 9yrs old. Early teens for a lace bra which was irresistible. I know I realized it was tabu at 8 for some reason. Never knew how I came up with that fear.
Somewhere around my early teens I first tried on a bra and panties with what I could find around my house. As soon as i could drive I went out and purchased my own set and that was more memorable.