I think the key to this is wanting it for yourself and not for your other half and then being relaxed when you do it. Most amazing orgasms can happen that way and then you will want it all of the time. :)
I agree with BlankeMaus on this one.
I would say keep trying, Ive had anal sex a former girlfriend and she didnt like it much at the beginning, but after some time i cought her spontaniously moaning loudly, practise is the thing.
I'd recommend a few smaller anal toys, try with a finger to begin with perhabs and gently massage till you feel ready to enter yourself, and massage yourself till you find the spot. Find a sex toy long enough to hit this spot and fall in love with anal.
Best advice: DO NOT RUSH IT, take time, if you dont feel comfortable around it, you will not get any sexual pleasure either. Good luck :)