is this normal? details in post

ok so my fwb and I had started doing anal back in May it took a few times to finally get it in(he is kinda bigger then most guys and he was the first I have ever done anal with) so we did it a few times and I really liked it. but we broke things off till a few days ago. we tried anal today and there was no way he was getting in. it was back to being painful like the first couple times we tried. is that normal? do we just need to redo everything we did before and get me use to it again or will it not work now that we stopped for a few months? comments and advice are welcome.