Reading this thread was very strange for me, and I hope you don't mind me posting.
In my early 20s I was with someone who I think was in the early stages of all of this. He talked a lot about wanting to wear women's clothes and experimented with women's underwear, high heals and make up. None of this really bothered me as I was young and I felt like we were exploring our sexualities together. Sometimes he talked about wanting to be a woman, and I think if he was a teenager now he would probably end up medically transitioning (I don't think that would have actually helped him, as I think it was very much a sexual fetish).
He was very controlling and claimed to be depressed/suicidal at times. Our relationship was all one way- I was never allowed to ask for emotional support from him, it was always all about him and his needs. The one time I tried, when I really needed some support as I was worried about redundancies/restructuring being announced at work he just wasn't interested and made it all about him. He was also a drug addict and even his best friend admitted he was a dick when he drank.
We didn't live together, so every weekend I had to drive to his house to see him. After work I was expected to skype him from the moment I got in to the moment I went to bed. If I pushed back, I got the guilt trips etc. He would never admit to being abusive though and I think in everything will forever see himself as the victim. I should have left the relationship long before I did, but I was genuinely afraid he would kill himself and it would be "my fault".
I never linked these things with the cross dressing thing until reading this thread, but I wonder if they are linked. He did blame his "depression" on "wanting to be a woman" but at the time he would never make actual steps towards transition, just dressing at home. He was very into a certain sort of look for me- corsets and leggings and so on. I was expected to perform femininity at all times, but somehow also not spend lots of time on my hair and make up as this was very upsetting for him as he couldn't do this out of the house (he absolutely could have done, his friends were nearly all the liberal accepting types).
Anyway, in the end he saw a text between me and his friend which made him think I had told the friend about his cross-dressing (I hadn't, because obviously that would be a dick move). His response was to physically throw me out of his house, knowing we had both been drinking and so couldn't drive. He lived very rurally and it was winter. I effectively had nowhere to go and he put me at massive risk. Apparently, I supposed to beg him to let me back in, but I didn't- instead I walked into town and stayed with a mutual friend, arguably putting myself at risk walking down dark country roads in the middle of the night, but whatever. The same friend went and got my stuff from him, and I was lucky to be able to cut him out of my life and move on.
Reading this thread has made me see just how lucky I was and how my life could have gone differently! I just want to say that I do get it and I do understand, and if I can ever be practical help for anyone in this situation, I would be. I am listening and I see you and support you.