Is prostate enlargement painful?

Usually not. You refer to urine flow which becomes more difficult in men as the prostate enlarges with age. It pushes on the urine outflow tract cause the symptoms of urgency, night frequency, slow and low flow and incomplete emptying of the bladder. It is uncomfortable, but no actual pain. Evaluation by your urologist to rule out cancer is needed. Meds to increase flow are available which can help.
No. Prostate enlargement is a normal process for the aging male. It occurs very slowly throughout the years and does not and should not cause pain. Pain in this area is a sign of another problem that should be evaluated and treated. Prostate enlargement usually causes some difficulty with urination but is not painful.