i have browsed this board many times. i am 15yrs old and this is my first time posting. i too have a problem with my foreskin. when flaccid, it can only retract about halfway along the glans, and when erect, it can barely be pulled back.
now, too my problem. when flaccid, it can be pulled back halfway along the glans. i do not go any further, because it seems to roll up on itself, rather than smoothly being pulled back. what seems to be the problem, is the frenulum. im not sure if it is short, it may be. after going through this board, ive read that it should be on the underside of the penis. mine doesnt seem to be on the direct underside...but more to the front. it is still under the peehold, lacking a better a choice of words. so when i pull my foreskin back...the tip of the penis points down, also adding to the problem. im not sure if im imagining it, but i do think it should be more on the underside. if it were, i think i would have no problem retracting my foreskin, because i do not think it would roll but just go back easily.
any help is appreciated.

"On the underside of the glans, the foreskin's point of attachment is advanced toward the meatus (urethral opening) and forms a bandlike ligament called the frenulum. It is identical to the frenulum that secures the tongue to the floor of the mouth. The foreskin's frenulum holds it in place over the glans, and, in conjunction with the smooth muscle fibres, helps return the retracted foreskin to its usual forward position over the glans." ("Where Is My Foreskin? The Case Against Circumcision," by Paul M. Fleiss, MD, Mothering, Winter 1997) Quoted from the foreskin organisation site where there is a photo too.
I think they vary a bit so I don't think what you describe (re. the attachment site) is abnormal. I'm not sure what you mean about the foreskin rolling up on itself as I thought that was normal too. I suspect you might need to stretch both the foreskin opening and the frenulum (fraenulum for those in the Commonwealth). Have a look on this site for detailed instructions on what to do for both and get back to us with questions.

mine rolls too but i can just barely get it over my head when erect.