When someone is tired of only seeing words online and wants to see the person behind the computer.
Stud88: "Hey girl, I'd like to take this chat up a notch..."
SexyWon: "Oh yeah, what did you have in mind?"
Stud88: "I want to see what's behind that keyboard... Let's stop typing and start skyping!"
SexyWon: "Ooohhh baby, let's!"
Masturbating, jacking off. a term used at military academies since theres not much female companionship and normally college students don't Skype with their grandparents.
Steve: Where's Joe been all this time?
Chuck: I don't know, probably Skyping with Grandma.
Steve: Wouldn't surprise me