Is this for something like the variable-extension cylinder somebody asked about in the pneumatics forum? Or is it something else?
Anyways, from what I can understand, you want to press a button and then have two events occur with some time between them, right? If so, take a look at CogCode2k2, available at my website,
http://www.robbayer.com/software.html. Last year, we had a system where you pushed a button on the joystick, the robot stopped for a second, the gear shifted for a second, and then the robot started moving again. With some minor modifications you can probably make it work for your application as it is the same basic concept. If you need help with the mods, email/PM me.