Losing virginity very soon- have some questions? (Contraception, other concerns)?

My boyfriend and I are 17, and we're both ready to have sex. We've been dating for a year and a half and I really love/trust him, but I'm still very worried (nothing to do with him- I have an anxiety disorder that makes me nervous about anything, especially when it's my first time- not just when it comes to sex). We were eachother's first kisses so obviously we're both inexperienced (we do talk about all of this together though), so I have a few questions that'll hopefully calm my worries- I apologize in advance if I sound absolutely clueless, I've tried to research as much as I can!

-We're only using a condom, as my parents don't want me to be on birth control pills. I think he's planning on pulling out as well if he can manage it, even with the condom on. Should I buy plan B online or something regardless and take it? I generally do not react well to medications (frequent upset stomachs) and that's one of the side effects of plan B, so I don't necessarily want to take it unless it's a very good idea to take in conjunction with the condom. There's no way I can have a baby right now, I still need to graduate and go to college. Is all of that effective enough for birth control?

-Whenever I get anxious, I tend to gag/get nauseous and come very close to vomiting. I often try to prevent it around him, and I've been successful. I definitely don't want this to happen while we're together, as intimacy (even making out- it's torture, as I want to enjoy it but worry the entire time) makes me anxious. How can I try to relax and prevent this?

-I have a health/period app, and it says that my fertile window is taking place at the exact same time we're planning on having sex. It says the chance is 7-9%. Is this bad?

-Should I put the condom on, or should I let him? I'm nervous that I won't put it on right, yet at the same time nervous that he wouldn't put it on right.

I'm sorry if any of this sounds ridiculous!!
Losing virginity very soon- have some questions? (Contraception, other concerns)?
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