well first off i am concerned that he is hassling you for sex. you shouldn't have sex with him just because he is putting pressure on you. do you think you are ready for sex? there can be serious emotional issues caused by rushing into sex too early or for the wrong reasons.
if you are contemplating sex you should be clear with each other about contraception unless you want to get pregnant. never have sex unprepared and unprotected as so many teenagers do. it only takes one sperm out of millions and having unprotected sex once to get pregnant.
also for the record, not all girls experience pain or bleed when they lose their virginity.
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