postions if it doesnt fit? please help

so me and my bf have tried having sex twice and it stung so bad both times and i told myself that i would just let him do whatever the second time and i would disregard the pain but it’s really bad i think i have a good pain tolerance he fingers me just fine and whenever we try we’re always lubed he’s totally respectful about it and im really lucky i’m having this issue with him rather the. anyone eles i think it just doesn’t fit in with any tips??