Sex advice needed! (anal)

Hello ladies! So I've come to a conclusion that I'm ready to try it.

My boyfriend and I are both adventurous. He's wanted to try anal for months now and I've tried using toys but it just makes me so uncomfortable. I want to be able to do it and am willing to try but do you have any advice on how to go about it effectively and/or ways to make it easier on yourself? I've tried lubes and plugs and even cold turkey attempts in the shower with him(at one point it almost worked out well). My ass is also extremely tight to the point where it hurts me and it takes a lot of effort to get a plug in there. Altough if it's his finger or a small plug I love it.

Thanks!