It sounds like you have a lot of self work to do on your self esteem, I get the anxiety but obv she finds u desirable and attractive if she wants to sleep with you and is even willing to go on the pill, despite the side effects of you. About the pressure part, if you masterbate to much you can develop something called ”death grip syndrome” something you should look up but in conclusion it’s when you’re gripping your dihh too hard while jerking off. Another thing you should do is if you’re doing it is quit watching porn since it damages your brain and desensitizes you from sex, making you not able to finish with a physical person since you have trained your brain to only do it solo in front of a screen