I need Pegging advice...

If you are both into it, just let it go naturally. If he's really hot for it, then it is probably going to go well. Just use lots of lube and let him guide you. When he is ready for some deep thrusting he will let you know. In the beginning I found being on top was very pleasant for me because I could control how much I took and how fast and it made it easy for my girl to play with my cock at the same time which makes it even more fun.

Have you done any anal play yet? It's best to start out with other types of anal play in order to get a feel for it (for both of you). Fingers or a handheld small toy are good ways to start. Try to find his prostate and figure out what types of stimulation he likes best.

Once you get a harness and dildo take some time to figure out how to use it on your own. Practice putting it on and thrusting. Pick out several positions to use so you can easily move around and find out which ones work and feel best.

Good advice again, ScottA!

When he's comfortable with anal play, he should be ready for pegging. Start with lots of lube and one finger (or similarly sized toy). When that's 100% comfortable, move up to two fingers. When that's comfortable, scissor the two fingers (or move the toy). After that, he should be ready to receive a modestly sized dildo. GO REALLY SLOW at every step. My wife and I found it came pretty naturally to us.

I suggest that he clean himself thoroughly before anal play. Something like this should work well.

My wife and I prefer the doggy position--but we started with me on my side. It's easier to relax on your side or on your back.

Above all, have fun!