I think the writing is pretty clean. Very easy to scan, not too much description. Personally I think there may be too many ellipses but that's just my preference. The dialogue feels realistic. I'm not really "getting" what's in the logline though - it feels like Caiden is actually pretty secure in his gender and sexuality. He's just new and shy with his teammates. I think any new kid would act this way at school. I don't know if you're using mastectomy scars to make sure the audience knows he's trans? that felt a little off to me since most young teens just go on puberty blockers and hormones. if you really want it to be more clear that Caiden still deals with gender dysphoria, what if he still binds and can't have surgery? Just a thought.
As for the chemistry between him and Rory, it was obvious at the last scene but wasn't really in the first scene together. Rory seemed just kind of lumped in with the other boys. You could probably differentiate him better, write some action lines about what he's doing while the other boys lightly tease Caiden.