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Hi theritegirl,

You ask a really good question that shows you’re trying to know as much as you can about something that’s new to you.  It sounds like you’re on the right track when it comes to having condoms and lube.  A condom prevents the transmission of some STDs and lubrication is important to use during anal sex because the anus does not lubricate on its own.  It’s also important to have lots of communication between the two of you, and to take things slowly to make sure both of you remain comfortable with what’s going on.  

Some people find that a new sexual behavior is easier when they try things that work up to it.  This doesn’t mean that everything happens all at once – sexual behavior with a partner is about exploring what feels good for BOTH people, and if something doesn’t feel comfortable for you, then it’s a good idea to regroup and discuss what you’re feeling and what your boundaries are.  

People have orgasms in reponse to a wide range of sexual behaviors, including anal sex.  Sexual behavior between two people should be pleasurable for both, not just for one person.  There are several parts of your post that seem to indicate you might be doing this only for him; sexual behavior of any type should not be done for someone else.  It’s just as much about what you want as what your partner wants.  As far as ejaculation goes, again, it’s up to you do decide what feels comfortable for you, and to communicate with him about what you’re feeling.