Yeah I agree with what aimee just said - there are some important concepts that persist. What you can click on in Windows 3.1 is basically the same as what you can click on on MacOS or Win 7 or any Linux interface. When you start using websites, the same concepts naturally persist, even though they don't really need to -- you still have a "menu" bar, dropdowns, etc that replicate what the OS is doing.
When my parents use a computer, they have literally no idea what they can click on and what they can't click on. It's completely alien to them, that this rounded thing here with "next" on it is called a "button" and you can click on it, but the word that says "installing program" is a "label" that you can't click on. They literally just see a flat canvas of colours and words, without any of the contours that define what "stands out" as something we more experienced users identify as "things I can click on". They would look at the word "quick reply" just above and to the left of this box that I'm typing in now, and click on that, wait 15 seconds, then wonder why on Earth nothing is happening. It's not intuitive for them to see those as just a "label", but this box here as a "text box" that I can type into.
Our generation is growing up having to develop new intuitions that are entirely separate to our evolved intuitions regarding the physical world. Other domestic technological breakthroughs in our parents' or grandparents' time, such as the internal combustion engine or washing machines, depended on physical interactions and could be understood by appealing to our innate physical intuition. I know that the chair I'm sitting on is different to the carpet it's standing on (and I'd know this with one eye shut or in a painting). I intuitively know that a bird flying is "alive" whereas a rock getting flung from a tree is "not alive". But without practice, I wouldn't intuitively know that the little things that say "quote" and "multi" to the bottom right of each post are "buttons" whereas the thing that says "Quick Reply" above this box I'm typing in is "not a button". You generate a new set of intuitions from practising with computers, just like with everything else. And the earlier you start, the more practice you get, and the more intuitive it becomes.
Probably the only other breakthrough in the field of technology that we had to develop a new set of intuitions for was electricity: it's not intuitive that rotating this magnet with wires wrapped around it can make that bit of metal over there start to glow. We now all know that a circuit must be complete, or what it means to be "grounded", and our parents understand this as well as we do (mostly). With plumbing or carpentry, you can just see how things work, without knowing any new concepts beyond a basic intuition about the physical world. But with things like electricity, computers, and cooking, it's hard to see cause and effect. It's easy to see that water goes down this thing here, spins that twirly thing, which turns that handle and grinds the corn. But it's much harder to see that if I wind more wires around the magnet, the bit of metal glows brighter, or if I click on this button here, I'll close that "window" (whatever that means), or if I mix all this crap together and put it in the oven for an hour, it'll turn into a pie. F-ing ovens: how do they work?!
@Illram: Yeah, obviously, moving from DOS to Windows is a huge jump, because one is a CLI and the other is a GUI. But almost nothing has changed between Windows 95 and Windows 7 - that's 15 years of near-identical user experiences! I dare say, someone in 1993 using Windows 3.1 could jump straight to Windows 7 without much fuss.