virginity problems

ok my boyfriend & i have tried this shit way too many times but it hurts A LOT so we couldn’t ever really do it. we’ve bought lube and we did lots of foreplay, i know i was pretty wet so that’s not the issue. im gonna be really honest with yall ive practiced a couple of times with a fucking cucumber but still every time i do it hurts. though i don’t do it a lot like i mainly focus on getting it in there as much as i can and when i do i just pull it out. this is a really embarrassing fucking story but i’m desperate it just always seems to hurt????