I've dated a trans girl who to this day I believe was my soul mate. I met her on a dating site and started chatting, but only met in person after a month or so. She was a student and I was working but outside of that we spent every minute together. We liked the same videogames, movies, food, and could talk for hours without getting bored. She's from an upper class family and I'm not, so I was way more anxious interacting with her social circle than I was with going out in public just the two of us.
Sex was awesome both on a physical and on an emotional level. I never connected with anyone like that, and probably never will. Topped most of the time, but tried bottoming once. Unfortunately I came so fast that she wasn't even able to enjoy it as I jumped off her cock and wasn't brave enough to get it back in. Oral was absolutely awesome, as well.
To me the best part of dating her was that I didn't need to guess whether she was actually having pleasure or pretending to have pleasure. A rock hard cock raining cum like it's monsoon season tells no lies, and for us it created this loop where she gets hard, which turns me on so I get harder, making her harder still, until we reach a climax that just doesn't happen the same way or as often with cis girls.
Anyway, our relation lasted for almost 8 months, but our social differences and the fact that I always wanted to have kids and be a family man led me to break up with her which was absolutely gut-wrenching and devastating for both of us. I obviously didn't mention those things, as I was actually relocating to another country for work and used the distance as an excuse. To this day as far as emotional self-harm goes that was the most damage I did to myself and another (beautiful) human being.
I ended up married with children and have an incredibly happy life, but after 12 years, still find myself wishing I could have cloned myself in order to take both paths in life without having to lose her.