Is it normal for sex to hurt everytime?

Hello, im a college student whose been sexually active since i was a teenager in hs, i lost my virginity to my hs boyfriend and everytime we did it, it never hurt. It just felt uncomfortable. Fast forward to a year after we broke up and didnt have any sex, i had my first encounter with a guy i was talking to and we just could not have sex because it hurt too much, even tho i was aroused.
I thought it was weird because ige never felt that way + i already had sex before. Now, i have been dating my boyfriend for 6 months and everytime we have sex it always hurts but the pain is maneagable sometimes, and sometimes i cant bear it. Is this normal?? I usually wear tampons too when im on my period so idk why it hurts so much to have sex.