Problem with tight foreskin

When I’m pulling the foreskin over the head of the penis, it is tightening so tightly under it and is not going all the way till end. There is this ligament which I definitely don’t want to tear, but it really hurts when I’m making out. Is it possible to cut it or do something else? (Male, 20 y. o.)

It would be recommended for you to cut the frenulum. The pain during sex comes from stretching this frenulum too hard, if you don’t cut it now with time it may start to tear from itself. At places of fissures there might adhesions form which will make it even harder for foreskin to move over head of the penis. Usually in such cases there are also partially narrowed ring of the foreskin which during full erection may cause pain and traumas.

It's not standing for me long enough and I don't manage to cum
How safe is that - to lick woman's "pussy"?