So I think I found what he is talking about:
In usual Internet fashion he is is kinda exagerating it a little bit but basically, Flyon was attacked by guard unprovoked and he started taliking about how dumb is that the punishments for Pickpocketing it dead, he then started talking about how this happens in real life and he hates it, because the system makes it harder for people doing bad stuff to get out it, and how specially hates how people will go to people having a rough time and tell "You should have done better in life" like is just that easy to fix you problems.
The only thing about trans was at 54:51 he ask one of his viewers what the flag in his icon is, he know is a LGBTQ flag but doesn't remember which.