I'm cis, so I'm not gonna try to give you advice about your feelings because that's not my place. I can maybe help with the makeup though - check out Lisa Eldridge on youtube. She has some great tutorials for simple looks that are a good place to start. Alexandra Anele is another one who does tutorials focused on the way certain techniques change the way your features look and she's a great resource for learning to blend. Drag queens are obviously the masters of things like color correcting a 5 o'clock shadow and feminizing features, but their other makeup is generally super advanced shit I wouldn't even try to imitate.