I was over weight most of my life until last year when I lost over 100 lbs. I was virgin up until last year when I got my first girlfriend after loosing all the weight. Sex for me is extremely painful, not enjoyable at all. I am not circumcised and when I have size, I have ALOT of pain around the "Frenulum of Prepuce" When my penis is not Erect, I can roll the foreskin all the way down to completely expose the head of my penis. When my Penis is erect however, I can't roll it down as far, just barely below the the base of the head. When I have sex, the area the Frenulum connects to my penis gets very sore and the Frenulum as well. Not just during sex...my Girlfriend was using her hand the other day and was a bit too forceful and it hurt, just like during sex. Is this something that will likely get better the more sex I have or is this likely going to be an ongoing problem?