Anal?...

Sorry in advance if TMI...So, my SO has wanted to do anal, but has never pushed me to do it. I've always initiated telling him I was ok to try it, and he did everything 'by the book' (foreplay, lots of lube, etc). We've done it maybe five times, and I just CAN'T do it! It's not that it doesn't feel good during, especially the last couple times we tried a desensitizing cream along with lots of lube. It's the after part that hurts a lot, and before we got the numbing cream even just his fingers going in a bit hurt like the dickens, and we never went farther than that after I told him it hurt. I've really wanted to just make him happy as he does enjoy it, but I also know he doesn't like seeing me in pain after..and I don't like being in pain after...I think our trying anal days are done though :P