Ok, I read this as a kid, so, about 1985 or so would be the latest it might have been printed; the copies of IASFM (Isaac Asimov's Science Fiction Magazine), however, were from a Yard Sale, and could have been any age.
The first story has two characters (teens, as I recall, but, since I was one, I may be misremembering), one of whom seems to be the servant or something similar to the other. They are on a planet where everything is idyllic, but only because technology is creating an artificial utopia. (The farmers work every day, but at night the machines undo the work so they have it to do the next day.)
One of the two characters confronts the person who set it up, who was once in the same category of Dystopia enforcing whatever that he is now.
The second story is several years later, and our main character has gained some degree of autonomy, as I recall, but that's about all I remember of it, other that some conflict between him and the character from the first story.
Not much to go on, but I remember being really fascinated by it. Any IASFM readers out there remember this one? I THINK one if not both of the stories were cover stories.