Never do anything you aren't comfortable with! Even for a new boyfriend. If you think it is painful, then don't do it. Really. If he's a guy who is into it an doesn't care that it hurts you, then he's a crummy lover and maybe not worth your effort. For real. You honestly may never like it. Some women do but a lot don't as well. Don't force yourself to do it to please. good luck
Anal after only three months of dating? And he asks for it often enough that you say "every time he asks me about anal sex"? Anal is usually something longer-term couples try after a few years of a satisfactory sex life, to spice things up and have some variety, or it's something desperate teen boys are willing to settle for because their girlfriends are freaked out about getting pregnant. Is this a relationship where you two are crazy about each other and get a huge kick out of just being together? If so, usually just plain old missionary is really delightful, in the early stages. If a relatively new guy in my life were to ask for anal a lot, I'd think that either he wants unprotected sex, or he's getting kind of bored with the whole relationship and so wants to get more stuff in the bedroom because there's nothing else there for him, or maybe that he's into feeling like the dominant man over the submissive woman, or maybe that he's actually closet gay. (I know this might sound far-fetched, but someone I dated briefly years ago was only into anal and I accidentally found out that that one of my friends who dated him later had the same experience with him, and then many years later, he came out as gay.)
Anyway, I would not be pleased if I thought any of those reasons were why my boyfriend was continually requesting anal. A guy should be wearing protection in this day and age, even if his girlfriend is on the Pill, for her sake as well as his. He should not be bored three months into a relationship, or using the girl for her body. He should not be someone who gets a secret thrill out of doing something to someone else that is possibly painful or might make her feel a bit degraded [if it did]. And if he's closet gay, well, depending on where you live he should explore the honest option of coming out. I could see this guy, if the two of you have been in love for a long time and have gotten great joy out of just walking down the street together or standing in line at the grocery store, saying "Honey, let's try some new positions," and letting things evolve from there. But so early? I just get the uncomfortable feeling he is not thinking of you.
Anal sex is a very intimate experience, something that a 3 month old relationship shouldnt even be thinking about. I worry that this would be just bragging rights for him. Also there is a protocol for anal sex. It is either anal or vaginal sex, not both as you run the risk of infection if not done properly.
All right I don't think the lenght of your relationship has anything to do with how you progress trough it - sexually. As with sex some people do it on a first date, some people wait a year. It is different from a person to person, and the same goes with anal sex.
If your boyfriend said he wants you to just try it and if you don't like it he can stop- you can do it, but here I agree with other commentors: the chance of you liking it almost none. The first time will be painfull and uncomfortable, and may make you never want to try it again. I wanted to do this for my husband, however I never got to liking it. Majority of women never does, but there are some that do. If you come to like it from that first tryout (which is pretty unlikely) good for both of you.
What, however, bothers me is if he is being too pushy. Men like anal sex, on average, but if that is soooo much on his mind that he brings it up constantly it would (for me at least) cause an opposite reaction and make me not wanna do it cause no one wants to feel forced to do whatever, let alone invasive sexual act.
If done right anal can be very pleasurable. Take it slow, and this seems like a gentle and patient enough guy... if you like him and would like to enjoy a couple orgasms go for it