Any experienced painter will tell you that the real secret to a successful paint job is in the preparation of the surface to be painted. Proper preparation not only will enhance the visual appeal of the surface, but will greatly improve the longevity of the product and its surface.
Preparation is especially important in this case, because the material (siding and decking) has never been sealed or otherwise protected. Decks, siding and all exterior wood surfaces become discolored from dirt and weathering.
Where should you begin? Start with a visit to your local paint store. Most major paint suppliers will have pressure-washing equipment available for rent by the day. You will need to use this pressure washer attached to your garden hose to remove all debris and dirt from the surface.
You will also want to hand clean bad areas with a bleaching solution. The paint supplier will be able to recommend a specific product designed to meet your individual needs. Most of these cleaning products can be applied with a stiff bristle brush and a sponge. Make sure to follow the manufacture's instructions, and always wear protective clothing, eye protection, and rubber gloves.
Once you have completed the cleaning step and the surface has been permitted to dry for a day or two, then you can apply the new finish. You will need to decide whether you want a clear finish or something with some color. Again your paint supplier will be able to offer some help in this area. Generally, you should look for an oil-based penetrating stain that not only will enhance the natural appeal of the wood, but extend its life as well.