I'm not 100% sure on the question...
-"how many times do you have to bench press"
Do you mean how many repetitions per set? That varies based on your goals. If you're trying to build muscle size it's generally recommened between 8-15 times. Less times is generally geared more towards strength and more is generally more for endurance.
Personally I like to make small increases of 5-10 lbs depending on the exercise, and focus on steady progress which will add up in time.