Make him develop feelings for you, than show him your penis

>>42793174
>he is super chuddy, and really really hates trannies
find someone that doesn't hate you
if you're just friends who cares, and it's not his business but also why talk to someone that hates you

>>42793174
He's prolly a repper himself.

>>42793207
honestly , he has been posting a suspicious number of "femboy memes"

>>42793174
Work on the foundation, not the roof. If you're helping him confront the things that frustrate him in life, and you're thoughtful in your approach, you can steadily and honestly cater to his needs while also setting the standards necessary to keep this train moving. Obsessive, personality eclipsing rage and hate don't come from places of deep and introspective engagement or maturity. they come from looking at things and feeling disgust, confusion, or discomfort of any fashion and thinking that it's some kind of fact of life that those feelings are informing you of, rather than a compulsive and anxious reaction to new things.

Is he talking about trans all the time and asking why they're so soft and neurotic? lamenting their representation in society because he has to imagine a woman but not as pretty?
If it doesn't come up, why does it matter? The reality is a bit manipulative, sure, but so are the strategies that led him to this thimble deep bias he has against people he's either never talked to, or never listened to. He doesn't hate trannies because of some essential nature he's divined through dozens of hours of sjw owned react compilations, he feels that way because he's made up an imaginary monster out of them and pretended they're satan for convenience and pleasure. It's satisfying and easy to imagine the world as a playground for monsters and heros, but it's not a rewarding or effective way to run your life. If he's actually a friend to you, i'm guessing you want him to be at least kind of balanced and prepared for life. In the worst case, you try your best to be decent and fair to him since he's unknowingly given you a chance to talk, and he ghosts you when he finds out. In that case, you can be sure you were at least one example for him, someone he can think "well they aren't all that bad despite", even if he thinks it's unreasonable to "trick" someone who he would abuse and objectify for fun at worst, and who he'd discount and patronize at best.