Anal Sex- Its a Love Hate relationship for me, and its been 10 Years.

If my hubby had it his way he would take anal EVERY CHANCE he had but me I like to save it for special occasions or maybe just those nights where I suprise him by telling him he can stick it in my ass. Now I HONESTLY DONT MIND doing anal but every once in a while its like my ass is telling me " alright lady, why do you keep doing this to me?" its not painful its just Uncomortable, you know like the first time you ever had anal. Does this happen to anyone else or is it just me? Now I have another inquiry, Has anyone ever actually had an orgasm while getting fucked in the ass? Because I have not and like I earlier Anal and I have a love hate relationship. So any advice would be greatly appreciated and used, because I kind of would like to know if an orgasm during anal would make it a lot more plesaurable in more ways than one.