Does anal get any better?

My fiancé and I have been together goin on 4 years..up until a few months ago far all we had done sexually is missionary..but we switched things up a few months ago when I began "riding" him..well this past week we had a falling out and have been trying to spice things up in bed to find our spark again..the first 2 nights were intense we went longer and came more than I think we ever have before..but last night we tried anal..I've never tried anal before it was kinda a rule with me..it felt good at first when it was just his head but as soon as he began thrusting and he buried himself completely it hurt too much and I told him to stop which he did but then a little while later he asked to try again and I said ok and we went for awhile until I could feel him ejaculate and I couldn't handle it..it just felt too weird and it still kinda hurt..my question is does it get easier?? Or does it ever feel better? I'm willing to try it again maybe not tonight or anytime soon but I'll try again..it felt kinda good but the pain outweighed the pleasure.. Sorry for any tmi