There is some implication here that we are not quite "on the same wavelength" in this discussion.
I gather that your problem is this: You
can slip your foreskin back to completely reveal the glans (head of the penis). This is quite easy when flaccid (soft), and when you get erect, it often pulls itself back anyway. I gather you are complaining that it is somehow difficult to pull it forward again to cover the head when erect and perhaps even when flaccid.
What puzzles me is exactly why this should be a problem, particularly why this might prove embarrassing when you are with a ladyfriend - what is it that you
expect it to do that it is not doing at present?
Now whether the tightness is a problem making it difficult to retract, or whether it is a problem pulling it forward afterwards, you presumably need to have it stretch wider. The
manoeuvre Jim references is certainly the way to do this stretch, it should be emphasised that the important details are that you have the foreskin
forward (which will be easier if you do
not have an erection at that point), that you get the fingers
fully inside the foreskin so that they are "hooked" inside the tight area and that you are pulling the fingers
apart rather than away from the body.
Which fingers does not matter, people who start with a
tight foreskin need to use the little fingers first. On the other hand(!), the middle fingers are probably the largest and easiest to use. Getting more fingers in is great, and what the diagram does not show is that you would generally be able to rest the fingers of opposite hands against each other to more comfortably "lever" them apart rather than using your arms to pull on them.
Please do clarify just what your problems were in the first place to see if we have missed anything.