Paskharen, don't mean to be argumentative, because it's impossible for a cut person to argue against someone with a foreskin as to how HIS skin reacts when erect. But to your first point, to imply that the skin "doesn't cover the head" for everyone is misleading. We can certainly agree that what you are describing is the nature of a foreskin, but some guys obviously have more skin than others and some have a tighter frenar band than others. The combination of the two, which may not be true in your case, is not necessarily true for others.
Not to make too fine of a point, but there seems to be an abundance of photos on this site alone to demonstrate that full coverage during an erection is not only possible but perhaps even normal for some. I should think the variety of foreskin types is no less abundant than the variety of length, shape, and other features of the penis among the population at large. I have been with a few guys where this was the case, and they were not so tight that I couldn't roll their skin over their glans. I also witnessed more than one fully covered morning woody poking out of flimsy boxers in the Navy when we had to spring out of bed during surprise drills or wake up calls. And of course, some boys and men with phimosis have to deal with this situation on a regular basis.
To clarify what I was talking about in my previous post, the goal I have is to grow my skin until it "loosely" covers my erection, which doesn't really contradict your contention or refute the reality of your particular anatomy. In fact, because I was circumcised at birth, I do not have the natural feature, a frenar band, that would hold it in place as it might for others, and it goes without saying that I will have to hold mine in place manually to know if it is long enough to fully cover my glans. My goal is to have excess coverage to cover it loosely, as opposed to growing just enough to forcefully cover the glans. In fact, if that was the goal then I would be able to do that fairly soon, but I wouldn't have enough to passively cover my glans at rest when flaccid. The two goals go hand in hand, so to speak.
I'm not saying you are wrong in any way, because your anatomy is your own, and that is your experience. I just want to make the counter-point to broaden the definition of a covered erect penis and explaining how I plan to judge when I have achieved my own goal in therms of aesthetics.
As to your question about whether an above average cut man usually needs lube to enter a vagina, I would have to say it depends on the size of the penis, or the sensitivity or the tightness of the vagina in question. While my penis is not that long, it is thicker than average and I don't recall having that problem when my partners were aroused and "very wet." I suppose there is a variety of viscosity to consider in women's natural lubricants, just as there is a variety in the pre-cum in men. My experience is somewhat limited in terms of the number of women I've been with frankly, but I have noticed a difference in the feel of their "wetness" from one woman to another. Some are more slippery and others more watery in nature. That's not to say that I haven't ever used lube with a woman, because I have. But when I have it was typically because I initially discovered that she was initially too tight for my girth, or for others, perhaps not as wet as other times for whatever reason. It could be that your mate is more watery than slippery in nature and therefor easier to irritate with friction. You didn't really describe the nature of her wetness. Perhaps her vagina is very sensitive and she simply prefers to have very little friction against her vagina during intercourse, in which case your foreskin equipped penis naturally reduces the amount of friction she would feel since it effectively glides within your skin, more or less in place within her, rather than feeling the kind of friction she would encounter with a tight-skinned cut penis that rubs against her with every thrust.
However, I envy your ability to enter her the way you do with your foreskin forward so that you push through your own skin to enter her. Sounds like something I would enjoy experiencing. But sliding into a warm wet vagina with a cut cock is what most of us here in the U.S. experience as the norm. So it's kinda hard for us to totally relate to your experience. Once I reach my goal, then perhaps I will have a chance to find out for myself.
I look forward to reading how others answer your questions. I hope I haven't offended you in any way by making the counter-point to your argument.