Oh, i can answer that question! Lots of foreplay (not just anal foreplay)- make sure she's screamin hot for you. Lots of fingering around the anus, rubbing it gently, that sort of thing. COMMUNICATION during the ENTIRE "finger near anus" time is very important, because if she says something hurts or is uncomfortable you must STOP. You can hurt some stuff majorly back there! Now, when it comes to actually putting your penis inside her, take a dollop of lube, put it right on her anus (having her bend over doggystyle is what works best for me), rub it around the anus and a little bit inside. Take another dollop of lube (about... coffee bean sized, too much isn't good, too little isn't good) put it on your penis, and rub it allll over- head, shaft, everything. Then, press the head of your penis against her anus.
It's important that during this time you TALK a lot about what's going on- she needs to be relaxed- I *love* rubbing my clit and my tits at this time, it takes the edge off of the initial insertion. GO SLOW. Listen to what she's saying and what she's not saying- is she pressing her body against you, or pulling it away? Once you get the head of your penis inside you're pretty much past the most difficult part. From there, just go slow, letting her take the reins as far as how fast you should slide in and out- always making sure you listen to her feedback. And throwing in a couple of "Oh, baby, your ass feels so good I want to take you to a nice romantic dinner this weekend to thank you for this" doesn't hurt either!
There's also a slew of books on the subject of anal play- I really like the Good Vibrations website - check out their
Sex Guide Books - there's lots of books on anal play as well as other fun stuff.
Also, I highly recommend
The Guide To Getting It ON! by Paul Johannes. Best sexuallity book I've EVER read, covers everything, is fun and witty and has some *great* illustrations.
