So my new partner wishes to try anal sex, I just am wary because a) I've never done it before b) I'm sort of scared that it might be painful c) the idea seems kind of dirty to me.
He likes to finger around that area to get me more comfortable with the idea, and while I must say it's not entirely unpleasant, I think there is a huge jump from him rimming with a finger to actually sticking a penis in there.
How can I make myself more comfortable with the idea? Because right now I don't really think I can go through with it.
Then don't. Look at the Golden Posts and the many threads on this topic. I have a Golden Post with most of the medical aspects. Personally, I enjoy anal play especially during cunnilingus, but no penis is going in there. If you do get around to it, use a condom - for his health; urethritis is usually caused by enterobacteria - those that belong in the rectum.
Yup, what she said.
If you want, you can certainly enjoy a tremendouse amount of pleasure from having him finger not only the outside but inside along the sphincter muscles--up to the first or second knuckle. These areas are richly endowed with extremely sensitive nerves that augment the sensations generated from other caresses.
Fingering him has the same effect; moreover, if you massage his prostate, it will be like lighting an afterburner on a jet engine or reving up a turbo on a gasoline engine. It will definitely give a kick to whatever else he is feeling at the moment for other forms of caresses. In addition, massaging the prostate will help bring about an orgasm if one is being somewhat illusive and difficult to trigger.
I'm with Brandye. I want to keep my penis out. I think this is the venue for fingers and dildos, only.
There can be some discomfort or localized pain if penetration is not done with care and plenty of lubrication. Before inserting a toy, a well lubricated finger should spread the lube around so that if either of you do insert a finger or toy, it won't rub against dry tissue. It goes without saying that the toy should also be well lubricated. You never want to chafe the skin. If you do have discomfort, STOP, and add more lube to the affected area.
Slowly and gently press, the finger or toy into the opening. Never shove, jab, or poke. The person on the receiving end should make a conscious effort to relax the sphincters. If this is difficult, then bear down. Another benefit of inserting a finger, first, is to condition the muscles into accepting something going in backwards.
Anal intercourse is all about getting his rocks off. Fingering and stroking the outside of the anus and inside passageway with a finger or toy is all about his or her pleasure. A finger can do much more to excite a person than a penis.