I never bled during or after my first time having sex, now 2 years later, I had sex with my boyfriend and I stated bleeding randomly, is it possible he has finally broken my hymen?
How much should you bleed?
how long for?
should it hurt after it?

Your hymen broke long ago. Bleeding varies from none to gushing. No 2 women are alike.
I WISH you would keep your questions together!
You could be menstruating. You say you are like clockwork, but almost no woman is for very many years.
Where are you in your cycle?
You could have 'something' unusual too, of course. Anyone can. You've been feeling queasy for days. A virus can throw you off. But there are several female conditions such as fibroids and pcos and others that can be uncomfortable, bleed at odd times, and so on. Usually you get an ultrasound and a pelvic exam.
Very early miscarriage is another.
And so on.