My girlfriend and I just started having sex, and one time we were using a condom (non-lubricated). When I first entered her, I felt a sharp pain initially. Then as we got going, I still felt sore so we stopped. Turns out that my foreskin got torn a little bit and was bleeding. It's fine now, but I wanted to know if changing to a lubricated condom would help this. I'd always felt a bit of stretching when entering, but nothing like this before.
This is typical enough. The frenulum is one of the least strong parts of the body. If you want it to heal faster, no sex or masturbation until it is fully healed. Otherwise, it will often tear again. A lubed condom is a great idea.