I am 16 and i can only retract it to a certain point where it starts to hurt can anyone tell me whats wrong or anything.
So, first of all, at the age you are your penis is still very much in the process of developing naturally - some refer to different names for sexual maturation.
Put simply, your penis will continue to develop until you are around 26 YOA - with most of the growth changes taking place prior to 20 YOA.
As it is now, your foreskin has not developed the natural suppleness and elasticity to accommodate and perform as it should, based on the size that the head of your penis has developed to now.
This is not a problem as this is a very common issue, and it is likely to change anyway as time goes on.
What you can do is learn about foreskin stretches as this will most likely help - you should also note frenulum stretches if you look up stuff online.
Always, if you do stretches start real easy, as you would a new gym exercise for example, and build on the amount you do - NEVER try to force change by exerting a great deal of pressure on your foreskin.
I can give you some examples of stretches to do, and a website to check out …