[DVDBear]

There is plenty of info, here and elsewhere on how to approach anal sex. Read up, be informed and go slow. The most important thing is if it hurts, STOP. I assume from your post you intend to top. If that's the case you've got a responsibility to pay very close attention to the signals your getting from him as to comfort level. Lube is incredibly important, as is tons of slow anal massage to get him to relax. But if you insert one or two fingers cut your nails and file them beforehand, or use a latex glove or condom over the fingers. Sharp or jagged nails are a no-no.

Oh, and one more thing . . . . I can understand you're both very anxious about this encounter, but knock off the booze! Not only does it inhibit your ability to make wise choices it can mask the level of pain the bottom is having. It really doesn't mix with this activity.