Phimosis maybe ?
An_247663 posted:
I am an uncircumcised 21 year old male and I have noticed that my foreskin does not retract back at all (flaccid or erect). It kind of just gets stuck at the head and if I try to force it back it hurts. I'm in a relationship and this becomes a big problem during intimate periods as the foreskin would just not slide over the head and get stuck. This has been a problem for many years but I didn't really care about it before up to now. On researching techniques to stretch the skin, I have tried pulling it back in the shower everyday but that doesn't seem to help. I would really appreciate any advice on fixing this from experts or any other individuals with the same problems.
counterso responded:
You need to be persistent and may need some particular cream that a urologist can prescribe for you that softens the skin and makes it easier to stretch. It will take time every day for several weeks to stretch this skin, perhaps multiple times per day for more than a few minutes.

I will insist that it is essential you be able to fully retract your foreskin without pain (for multiple reasons), so you need to do the work to get to that point. Your alternative is to have the skin notched (you don't need a circumcision), to relieve that pressure.

You may have given up too soon, or not been persistent or aggressive enough to actually stretch the skin. It requires work (not pain), and diligence if you want to avoid surgery or the risks of not being able to retract properly.