1. Clean Your Pipe - It's vital to ensure your pipe is free of any previous ashes or condensation for a previous smoke. Run a pipe cleaner through the stem and then blow on the stem to ensure nothing is blocking the air passage to the bowl. I would highly suggest you turn the bowl away from your face otherwise you'll end up with a face full of dottle (ashes and unburned tobacco).
2. Prepare the Tobacco - Remove the approximate amount of tobacco you'll need to fill the bowl and place it on a napkin. Make sure the tobacco is free of any clumps and that the moisture level of the tobacco isn't to wet. If it is let it sit out for a couple of minutes while you take in the fresh air of the evening.3. Filling the Bowl - Loosely fill the bowl with tobacco. At anytime while filling DO NOT press down on the tobacco with your thumb or fingers. Also don't pinch the tobacco so tightly that you create clumps which you got rid of in step 2. Now with your handy tamper tool press the tobacco down until its springy. The bowl should probably be around half to 3/4 of the way full. Remember the tobacco should be springy not rock hard. Take a test draw from the stem. Is there any resistance? If so dump out the tobacco or stir it up with your pick and start over. Otherwise fill the bowl back up and tamp it down again. Take another test draw. Again there should be little to no resistance. If there is more resistance the breathing through a drinking straw, dump or stir the tobacco and start over. If the tobacco still isn't even with the top of the bowl add more tobacco and tamp it down so that it's now even with the top. Another test draw should yield only a little resistance.
The True Light - After the false light the tobacco may not be at the same level - the top of the bowl. Use your tamper to lightly compress the tobacco back to the top of the bowl. Be extra careful here, this is where many beginners make their biggest mistake. Relight the match and again apply it to the tobacco in a circular motion. Again a series of shallow puffs will be necessary to stoke the flame. If done properly the tobacco should not unravel or puff up like it did during the false light. Not its time to enjoy your pipe!
If your pipe goes out while between puffs don't worry. That's perfectly normal. Just relight as you did in the True Light step above. Many pipe smokers will relight at least once during a smoke. You may find the pipe getting a little juicy as you smoke. To avoid this try keeping your mouth as dry as possible. You may want to consider running a pipe cleaner down the stem to clear it out. Let the pipe cleaner sit for a moment and withdraw. Whatever you do, don't take the stem off the pipe while it's still hot, as this will eventually cause the stem to get loose or even break. If at any time your pipe starts to taste nasty, stop. Pipe smoking is always supposed to be pleasant and there's no reason why it shouldn't always be so. This is most likely caused by smoking to fast or the pipe not being properly broken in.