Does he have a lip tie? Definitely try a nipple shield like @smilingwithmyawesome4kids suggested. It can definitely be hard at times. Just keep trying, you and LO should get the hang of it. But if you really can't do it, pump and give LO breast milk through bottle if he'll take it.
My daughter is the same way !! Drive me nuts until I bought a nipple shield & try to get him to latch on before he starts crying that's what my daughter pediatrician told me to do
agree with @js_mom