I got my right nipple pierced about 30 year ago, long before I was cross dressing (damn it hurt). A number of coworkers (mostly female) had done it and it was talked about a bit since it was not quite a mainstream thing back then. So a younger coworker and I thought it would be cool to do. I don't think he was even 21 at the time and I was in my 30's.
About 10 years later I got my navel and left nipple pierced. I also had another piercing that I did myself around the same time. Non of these had anything to do with trying to be feminine. It was about 5 years later that I started wearing panties occasionally and then full time shortly after that. It was such a good feel going into the men's room at work and looking down to see my panties with that little bow in front. ❤️
About the same time I had brought a few dresses at an outlet and was occasionally wearing them at home.
For a number of years panties was enough, until I found some bra's that fit and could be worn under my shirts, with out being detected. Suddenly I found myself wearing bra's full time, except when sleeping.
Bra's and Panties got me by for a number of years. Up until then I thought it was still just a cross dressing thing. Eventually I moved to padded bras and shirts that were a little more feminine. Then I progressed to women's jeans, more feminine tops at times, and padding in my bras. Soon enough, that became most of the time.
One day about 3, 3 and a half years ago I was finishing up my annual checkup with my GP and I told her I needed breast. Not wanted, needed.
There still are a few times where I present 100% male, maybe 90% male but 99% of people don't notice that 10%. The rest of the time I present male with breasts, in women's clothing. I'm never going to pass but that's okay, I'm just fine with being me at this point. I'm not done though, still have a couple of things that are giving me a little heart ache.