My wife and two daughters know of my crossdressing. My wife has been part of this from the beginning, Mid-August 2019. There were lots of hints before that of this oddness inside me. And we still haven't figured out exactly what triggered Jessie Mae's full epiphany.
My wife and I both agreed that at some point it would be wise to let the girls in on it (both are in their 30's and married). Especially the youngest who lives in the same town. Couldn't have her stopping by unannounced some Saturday and NOT finding dad, but Jessie. But we weren't quite ready.

For some reason that escapes me now, it seemed like a good idea for Jessie to have her own Facebook account and to have a photo album. She only had two friends (boy me and wife), what could possibly go wrong? On October 8th I started uploading some photos my wife had taken of me. (Did I mention I'm 64 and hate Facebook and don't really understand how it works?). These popups kept appearing asking if I wanted to tag "boy-me" in the pictures. I thought I'd click no each time?..

Later that day, at exactly 4:14, a text arrives from my oldest "Saw your pictures on Facebook!" ( pictures?, what pictures?)

"Oh? What'd you think?" was my sheepish reply.

"Interesting. Is this a new look?"

I tried to explain how this was another aspect of me, blah, blah blah.
She explained to me that I had tagged my boy-self! Panic!!! Frantically I started deleting pictures on FB. And after a few more texts we scheduled a phone call for later.

The first thing I said was "Do you have any questions?" She asked if I was still going to be dad or if Jessie was going to show up for Thanksgiving dinner. I assured her that this was only one side of me whose time had come to be expressed, but only in private. Then she mentioned that she had contacted her sister before texting me! Oh, s@#t.

My wife insisted that I talk to our youngest right away. She has her own business, so we scheduled a meeting for the next evening. That was a very long 24 hours. Every possible disaster scenario went through my head. Closing time finally comes, we sit down and I ask "So, what did your sister tell you?" "Oh, she sent me a picture, but we weren't sure who it was." She also asked if she now going to have two moms. Turned out, she was incredibly accepting and supportive.

Now the three most important women in my life know that I am also Jessie Mae. I don't have to worry about how or went to tell them. Facebook (or my ignorance of FB) took care of that.

I am bless with a great wife and two fantastic daughters. So far, so good.

BTW, I don't recommend this method for coming out!