When should I test?

Jadah • ♡here for a good time♡

I took a test 5 days before my period because my breasts were swollen and sore, in a way that they never have been before, it came out negative. I was having the worst headaches, and my period is late on one app and will soon be late on another (this one is like clockwork, says I'm supposed to start tomorrow). When should I test again? A week after clockwork or ASAP? I always have mild nausea due to digestion issues so I can never trust my stomach. I have a history of cysts that have stopped my period and my birth control (implant) can get wonky. My boyfriend and I have sex without condoms all the time but he pulls out, and when he does use one he busts inside me. I'm spooked all to hell, when should I test... I'm starting the EMT program in a few days and I am so scared.