If you're not married and not willing to risk pregnancy, you absolutely need to be using condoms. Really, you should be using contraception as well.
A condom mostly prevents enough "drag" being exerted on the foreskin, to cause it to be pulled back, so is considerably more comfortable if there is a problem with tightness. If the foreskin is quite tight and cannot be retract when flaccid, then it will be even less possible for it to be retracted when erect, and there will be negligible tension at the opening to cause discomfort. Only when it is almost retractable will it come back far enough over the glans that the glans tends to stretch it open that last degree and cause pain.
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