Sometimes you don't bleed, sometimes a little, so you don't exactly know if it happened. It might have already been partially or completely broken (it happens for unsexual reasons such as horsebackriding, tampons, ect.) You can have sex with it staying partially in tact I think, and that might be why it still hurts?
if you have sex, you're not a virgin. you "cherry" might have "popped" during any daily activity that you do
Perhaps his penis was too small.
I was with a girl once who had been with only one guy. She said that they had sex, often, but when I had sex with her, it hurt and she did end up bleeding a bit.
The answer I guess, is that there may be some hymen intact and your next boyfriend may fix that.
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