Most of the people who are responding must be secretly wishing your relationship fails. The reality is, if you love the guy, I mean really love him, you are going to have to try this for him. Sometimes you have to do things you dont enjoy doing for the sake of love.
Most of these people responding are not in love, and probably have never been in love. When you love somebody you will do anything for them ( within reason ). His request is certainly not out of line.
If you end up taking the advice of the people on this forum and "never do anything you dont want to do" you will surely never have a lasting loving relationship, and you will probably regret it when you are old and dying alone.
In short, as you have had lots of advice, NEVER do anything you don't want to do. You need to work on your self esteem, and work on your strength to be firm about it, because it simply sounds like you are way to vulnerable, thus he only sees that, and that's the only reason he keeps mentioning it. It's not that he doesn't care about you, it's that you aren't being firm in what you want, you are still in the mindset that you should please him, when in all truth, you shouldn't care about that. Anal sex is not the only way he can be satisfied, and it's not going to be the end of his world, and certainly, won't be a reason for him to leave you, those are your own fears you need to work on.
If a man desires a B.J. maybe he should first perform one. If a man desires anal sex maybe he should be penetrated there himself - maybe he needs to see how difficult these feats can somethimes be.
But seriously, You should not be pressured to do anything that brings You discomfort - physically OR emotionally. If this is a deal breaker for him maybe You should consider why he would end a relationship over anal sex. That doesn't sound particularly loving, sensitive or affectionate. You should not have to compromise Your feelings for fear of losing this relationship.
Youve got every right to deny him that. No means no-end of the story. Furthermore, if this guy is that loving and affectionate, why would he insist on something that you have clearly said no too???
Bottom line is....no means no! End of the discussion. If he cant deal with that, dont compromise your feelings/body for a guy who isnt considerate of your feelings/body.
Coming in after all of this great advice. I agree that a heart to heart is necessary here. You've tried it, your not into it, and end of story. No sense pretending you love it or doing it just for him as that isn't going to really build intimacy for the two of you. He'll either say -------- "hey, I'd like you to enjoy our sex life" or "hey, love ya but love the anal and am off to find some". It really is that simple. Sometimes we are compatible with someone sexually and sometimes we aren't. And when we aren't, I'd always suggest not to go further with the relationship. Good luck
Chatty, I think this relationship is doomed. This isn't just a guy who's curious about anal sex, this is what he prefers obviously. He's not willing to give it up.
When you say you don't want to do this, it's uncomfortable for you, do you mean you've tried it and found it to be uncomfortable/painful/whatever? What does he say when you say well I HAVE tried it and I don't like it?
I don't see this relationship lasting. When you're dating you find people who are "matches" and people who aren't.
It seems that primarily he wants anal sex, and you don't, so this is a no fault break up. You two aren't a match.
I would be this blunt with him, and accept his blunt answer:
"The answer is no on anal. No. No amount of begging and wheedling and telling me I like something I don't is going to change anything, the answer is no. Is that a deal breaker because we shouldn't waste any more time in this relationship together if we're still arguing about this". And then just proceed from there.