For most sissies, I think their first fascination with crossdressing involves panties. Panties are also probably the most popular item that helps symbolize or reinforce a Femdom/sub sissy male relationship. Phrases like "She keeps me in panties 24/7..." are very popular when people describe such things.
I'm no different. I owned many pairs of panties before I got my own bra, and that bra was"outnumbered" by the various styles of panties I had for many, many years. As my cd fetish and submission to Diane evolved into a lifestyle, more bras were added and I was made to wear them more often.
Today, they are part of my everyday wear. This morning while getting dressed, I thought about the first time I wore one, and how difficult it was to put on. That first time, I was alone and just couldn't get the darned thing hooked in the back. I finally decided to hook it together before putting it on and slid it over my head and shoulders and finally got it adjusted correctly. My struggle that day was far from feminine in appearance!
Diane would just giggle and tell me to start over. Once I would get one bra "hooked on" I was given another to try. This went on for hours, until I got it just right. I got the hang of it and by the end of the practice session, was slipping the bras on just like a woman.
This morning as I slipped on the bra I'm wearing while looking in the mirror, I realized just how feminine I look while doing it. It's all the result of that initial practice session, and all the practice I've gotten since then.