Tips to make it as painless as possible? Lube recommendations?

So my boyfriend (22M) and I (21F) have been together for 4 1/2 years and we both tried anal for the first time about 3 1/2 years ago. After that we used to do it every time we had sex and really enjoyed it. The first few times it hurt a lot but then as we started doing it all the time and I wore plugs before sex it didn’t anymore. We had a period where we were going through some stuff and didn’t have much sex so when we tried to do anal again awhile later it started to hurt really bad of course. We’ve tried to again a few times since but It would hurt so bad because I wasn’t used to it so I’d end up telling him to pull out before he was even halfway in. So now it’s been about a year and a 1/2 since when we stopped having anal and I bought another plug to wear so we can try again. I want to buy a lube to try but I need some advice. Does desentizing lube like Anal-eze and Xesso work well? What are the pros/cons? Am i better off just getting a normal lube? I’ve never purchased one before but I feel like it will help and I’d love some recommendations. Thank you!