Do I need to pay taxes on taxed money coming in on a monthly base

It depends on the nature of the income.

Salary/wages under Form W-2 have taxes withheld from each paycheck.

Contractor income has NO money withheld, so you have to make quarterly estimated payments usi.g Form 1040-ES.

Social Security is not taxable if that is your only income.

Pensions will normally witjhpld income taxes for both federal and state if you ask them to.