You mentioned you're only "free" if you have no outside obligations, yet at the same time you call yourself "repressed" and even call it a "mental prison". I find that contradictory. It took me 35 years to get out of my mental prison, but I now realize it was entirely self-imposed. I was worried about my parents, brother and sister, they didn't mind. I was worried about my son, he told me he's proud of me. I didn't lose any friends over it either. I'm worried about my business, but am hearing about transgenders who are thriving. All the worst case scenarios I thought of so far turned out to be untrue.
So my idea is, that you should be true to your feeling and not repress anything. You're not in any way obliged to your environment to be male. If you feel numb, depressed, engage in extreme sexual behavior just to feel briefly acknowledged as woman, I believe that suffering is actually worse than transitioning.
It took me a heart attack to realize that. Last April, I didn't realize I was having one and was just sitting on the couch, waiting for the pain to subside. But it didn't, it just got worse. It was during one of the dates we're discussing, i was completely en femme and it was due to taking kamagra (I need that with gay men,not my natural center of attention) and poppers at the same time, that I had a heart attack to start with. When the pain started, i just sent my date home.
At some point I thought I was dying and at that moment, instead of resisting, I just embraced death. I survived, was dottered and had a stent placed, but the event made me wonder afterwards why I had so little to live for that I didn't even care about dying. Why I was so numb. So that's what repression does.