When you are devoloping a relationship with someone, you need to feel comfortable. When you don't feel comfortable, it's because the power balance is moving one sided. When someone pays, you are in a lower power position. This position makes you harder to have a proper negotiating position. This is the root cause why you don't feel comfortable about him paying, because you feel as if you owe him something, owe him a favour, that he has done something for you. And because the power balance shift, you subconsciously feel uncomfortable.
There are other ways how power might shift. For example if you establish a structural vertical position eg if you become his secretary. Since you are in school, this could mean if he is your CCA head, or if he is a popular guy in school, or if he's the class prefect. Another is if you move into his zone of power. This could mean if you go to his house, or his other zones where he will display more dominance.
To maintain a comfortable relationship, you need to have a neutral-power, balanced position. This way you can approach and develop the relationship.
If you don't feel comfortable, as you are currently describing, the relationship will be unhealthy if you continue. You will feel presurized, guilty, doubtful, uneasy. You will feel ambiguous subconsciously as to whether to fight for more neutrality or to accept and accede your lower power position. The initial lower power position resulting in lower negotiating position would also present orientation problem for you. Such as not knowing exactly how to reject him. That is an example.
My advice is, you need to neutralize the balance. At least for now during initial development phases of the relationship. As the relationship progresses, you might comfortably settle down in a certain degree of position where both of you are comfortable in.
SO TO SUMMARIZE my long reply, for now balance the power and dont make yourself uncomfortable in any way. If you're unable to balance it, then he's not the right man for you.
