Let's just start with his inability to "make room for [you]" and his inability or unwillingness to "move forward in the grieving process."  These are HUGE relationship red flags.  They indicate he is not ready to commit to another relationship or to another woman.  And if you continue to stay involved with him romantically and sexually, on the basis of promise and potential, you are letting yourself in for a large degree of uncertainty and anxiety.
   Add in the crossdressing: you are "trying to deal with" it.  Another layer of difficulty and uncertainty in an already unsteady relationship.
  Now add in his sexuality--he isn't heterosexual.  He's an autogynephilic trans identified male.  You already sense that sex is "different."  Well, you can expect it to get more so over time, as he accustoms you to accepting more and more.  It's likely you will be asked to step into the role of initiator and he into passivity, because he will define woman as passive and done to.  You will not have a sexual relationship in which you meet as equals, or in which you can play around with your roles.  It will be important for him to act out his desires; he will be making love to himself as a woman as much as he is making love to you--you will be a prop--not even a supporting character--in the play he is writing, scripting, and starring in.  
  Don't you wonder why he told you he's a crossdresser and a man who wants to be a woman just as you were about to leave him?  Did he do this in order to test you, to see what you could tolerate?  Did he tell you this in order to win your sympathy, to resecure you?  Did he tell you because in telling you a secret he thought you would feel special or would want to help him?  Was it a species of ultimatum?  That is, did he tell you in order to tell you what you would have to accept if you wanted a relationship?  My ex did this, I realized later: in the first stages, he said to me, "To the extent you can enjoy me as a woman we have a future together."  At the time, I did not recognize this for the ultimatum it was, and a pronouncement that my role would be adapt and accept, that he was not willing to compromise in any way, shape, or form.  
   Add these all up and I see a lot of grief for you in the future. 
   You asked for advice: mine is to stop teaching with him and cut off all contact, because otherwise you will remain subject to emotional manipulation.  He's not good relationship material.  He's the walking disordered who would like to bring you into his closet and isolate you there.  
    In short, run like your hair's on fire.  

Last edited by OutofHisCloset (April 13, 2019 11:14 am)

Ying, for what it's worth I agree with Outof his and with Duped;  RUN

I agree with the others, get out of it!  It will only get worse. I’m in the process of starting to get out of a 32+ year marriage.  It gets worse every day. They aren’t concerned with our feelings, it’s all about them
Good Luck.

You have invested 7 months - get out now before you end up like me and invest 10 years only to have it demoralize yourself and everything you feel. Unless you want a woman for a partner - get out now.

I wish someone would have told me that 7 months in. I thought it was just some clothing, but its not. That is what they like to think and tell you but its not true. I have no desire to live with a woman and yet here I am stuck now.
Good luck.