My school starts on August 23. I have an assignment due then including annotating 9 (more) short stories and writing an essay. How should I go about doing this? What do you think the consequences would be IF I decided to skip it? (edit: English is my worst + least favorite subject btw)

Just make a plan to do it, Nina. Even though you don't like the class and might actually want to hate to do the assignment, I would pose this question to you:

You get a job and your boss asks you to do something and inside your head, you're saying - there is NO WAY I want to do this. What do you do? Just walk away and say - I don't think so?

You need to find a way to just do things you don't like or are uncomfortable doing, because sooner or later, this will come up over and over again. If you refuse to do a task at your job because you don't want to, that leaves the boss the option to fire you for being insubordinate.

This is a learned skill. Don't walk away from the lesson.

I suggest you start reading a story a day and take notes. That will give you time to write your essay. Why would you try to skip it? One of the consequences is you start the school year in the hole and the teachers are going to peg you as a slacker.