I was gonna start a new thread here about this, but here's a much better place to do it - advance warning, this is likely to be tealdeer, so I hope you like to read..
I'm a genderqueer FTM (mentally fluid/neutral, physically transitioning to male). I got found on OKCupid by this guy I'll refer to as K; he marked his profile as male and mentioned that he's transgendered, so the automatic response was to think he was also FTM. Two months of messaging and a month of texting later, we met up for a semi-awkward first date, partly 'cause it had been a while for both of us and partly 'cause it turns out he's actually going the other way - "physically male but doesn't want to be" was how he put it. Oops. Mind you, once the air was cleared and no I don't mind which way you're going, he showed over text the following day that he was really keen for a relationship

We've met twice more since, still texting each other a lot; in real terms it's been about 2 months since we started dating. However, in getting to know a little more about where we both stand in terms of transition (or not, in his case), gender identity etc, things are starting to bother me. Not in a bad way, far from it, but still...
I say "he" at this point only because he's still full time living/presenting as male, but it turns out we're about the same - mentally GQ, physically needing to transition. K however feels stuck; after looking into transition while at Uni several years ago, he's now back living with his parents and in a job he's not too happy in, but has a car to run. In a lot of ways he's where I used to be: quiet, withdrawn, barely going out, not good around people, that kind of thing. I could tell before this last meeting that he wasn't happy, but we had quite a chat about this last time (Saturday just gone).
The date itself was amazing. The idea was to take him round this abbey nearby since it's in a quiet area, but what actually happened was a whole day spent cuddling - among other things

- in my room. When he complained about his bits I asked if he was alright using them before we got up to anything, although I did notice he was gazing at/stroking my chest a lot, sometimes with his eyes closed, and it was sad to watch knowing why

During one of our chats I finally told him that I was concerned, because I know it doesn't go away, and I'm currently feeling a little helpless - at this early stage I don't want to start pushing him, especially if he's not ready yet, but being so far down the line and seeing him suffer the same way I used to is hard

On a more positive note, I'm pretty sure my trans status was partly what drew him to me in the first place, and it's certainly formed a good part of the bond we have

Feels so nice for us to be able to complain about things like society and its attitudes, being included in conversations etc, and to respond to each other with "Know exactly what you mean".