As part of my experiments in aerial refueling with KAS I put two airplanes up at the same time, it was actually really simple and the only stipulation is that they have to stay within the 2.25km of each other (you can of course increase that with mods). Basically you launch one plane, drive/fly it off the side of the runway, then switch back to space center to launch another plane. Now you have two planes sitting near each other. Throttle one up, pitch up and engage ASAS (throttle back if exceeding 2.25 km is a factor), then quickly switch to the other plane with "[" or "]". I know it doesn't make sense, but I've never had trouble switching between throttled up planes in the atmosphere. From there you quickly throttle up and race to catch up with the other plane. As long as you're within 2.25 km you can do whatever you want. Sadly my aviation pioneers were unable to refuel one plane from another, as the refueling boom proved unstable and impossible to intercept at speeds slow enough to allow docking and preclude explosions.