One thing crossdressers and all others on the gender spectrum end up doing is choosing a femme name. A name separate from yourself but also represents yourself. This could be a screen name or as I used it a pen name to add some privacy. It may also be a character name for a role you play. Or maybe it’s the name you want to use eventually for everyday life. Or all of them. I was using Jess as my middle name is Jesse so it seems like a good enough fit with people assuming it was short for Jessica. Which worked but I never really used it offline and just used my first name and have never really had any particular attachment to my middle name.
So what changed? Simply put I accepted that it was more than crossdressing and that I am Bigendered, a term that hadn’t existed years before. So everything started to click in my brain and I wanted a name for her distinct from him. I tried Jessica for a while and poked around but nothing really stuck. Then I found that Jessie is simply the feminine spelling of Jesse and goes back just as far in Scottish usage which lends itself to my heritage. So I tried it out for awhile and tried writing it out along with Jessica to see which seemed more natural. And so Jessie won out.
What has been the result? Honestly I have grown to really like my middle name and actually feel like it represents me well. Having a feminine name that relates to me is great, though I still respond to either. For me it is not as much as having a pen name or a name for her but a name that represents me as both a man and a woman. So choose one or don’t, it is nice to have one though.