Hey I Am Not A Virgin And Did Not Bleed

hey i am not a virgin and did not bleed my first time but my last few times having intercorse have hurt so badly. he tries to insert his penis and i try to guide it correctly but no matter what angle we go at it it still makes me bleed and i feel this sharp stretching pain. it goes away the more we continue on with the session but when he pulls out of me i find i am bleeding.