Can anyone help me figure out what's going on with my dick?

Please don’t try to do anything on your own, but go see a urologist who is recommended by your primary physician. This is probably rather simple to correct, and it needs to be done safely so that it will heal correctly and you don’t develop an infection. Good luck!
 
I am not a medical doctor, and you should see one. The normal foreskin adheres to the head of the penis, but eventually separates naturally when masturbation begins. If that is what this is then you would be able to roll it back little by little each day. This looks more like a skin bridge which is reasonably common after infant circumcision - do a web search for penile adhesions and skin bridges - this is where the head and shaft skin (or foreskin in your case) permanently fuse, and require relatively simple surgery to separate (nothing like a full circumcision) - and I would recommend having a professional do it because you only get one penis, and you don't want unnecessary scar tissue.

This may even fix your phimosis.