Hey, mrenziboi!
I'm so glad that you've found the way to connect a rich heritage of Jewish texts and knowledge with the trans issues. As you've already learned, you are not alone - there are many trans Jewish people and trans allies who are doing the same in this very moment.
Perhaps you already know, but there's a TransTorah project that struggles with this topic - maybe you'll find it interesting (or maybe you know about the project already!):
http://www.transtorah.org/aboutus.htmlThen there is also this site:
http://www.ritualwell.org/ that works on a possibility of developing Jewish rituals, blessings etc. adjusting many "new" circumstances in nowadays society (or a circumstances that are just getting more visibility these days - they are not "new" at all really!) - there is also a section for LGBTTIQ issues and life circumstances. Personally I don't know to how extent I am comfortable with the idea of so many
new rituals that we can just come up with (I'm sure that the old texts have as much potential in the mean of interpretation/interpretability as the new ones and basically I'm more interested in older texts right now), although I definitely see the potential of innovation and adjustment to a contemporary society and individual problems and issues in Judaism and I agree that Judaism has a capacity to stay in touch with the contemporary living in theory as in practical life.
Then there is this book
http://www.amazon.com/Torah-Queeries-Weekly-Commentaries-Hebrew/dp/0814720129, which follows weekly Torah portions interpreting them from a queer and gender theory perspective.
Since I'm familiar with gender and queer theory (it's my major on PhD studies, particularly postfeminism studies), feel free to ask anything from that domain if you are interested in discussion or sharing thoughts.