So my boyfriend & I are doing long distance rn & before I left we tried anal (I'd done it before but he hadn't & wanted to try it, so we did it), it hurt a lot more than it had in the past & we ended up stopping because it hurt really bad. The times I'd done it with past boyfriends, it never hurt & I actually sorta enjoyed it, but it hurt so bad with him & idk why.

But yesterday we were sexting & he said that he wanted to do anal again because it felt really good, & I said ok because I don't not like it but it just hurt a lot last time so now I'm kinda scared it's going to hurt really bad again

Anyway to make it not hurt as bad so that I can actually enjoy it?

Also what's the best position to do it in, because I think maybe that might've had something to do with it because in the past I'd don't it in doggy, whereas the time I did it with him, I was on top.