Lift a 20-foot extension ladder up onto the top of the first story of your house. Use a regular extension ladder to reach the top of the first story.
Set up the 20-foot extension ladder on the roof of the first story if the eaves are recessed so far back that a tall ladder can't reach them from the ground. Use leg stabilizers to support the ladder and protect the roof. Adjust the levels on the legs so they are even. Ensure that the top of the ladder is at least 3 feet above the part it rests on.
Find an assistant to support the ladder while you climb up. Climb up the ladder carrying your painting supplies. Make several trips if necessary.
Paint the eaves using a quality exterior paint, while standing below the top three rungs of the ladder. Standing any higher causes you to lose stability.