Penetration hurts every first time!!

Girls i need help, i have been stressing out about this for 3 months and idk what to do anymore 😓

Every time my boyfriend puts it in it hurts and i feel so tight the first time to a point where i tell him to take it out

(despite spending alot of time on foreplay+lots of lube)

he has to take it out and put it in multiple time then the pain goes away completely and i feel less tight for some reason.

This obviously completely kills the mood 😓💔

This has been happening for 3 months since i lost my virginity. It is so weird that the pain completely disappears during third/second time.

Please let me know what can i do! 😢