1} Cannot retract at all, even when flaccid. May not even be able to see the tip of the glans and urethral meatus at all.
2} Can retract - with difficulty - when flaccid, but not a hope when erect.
3} Can just
retract when erect, but the foreskin gets "caught" behind the glans (in that little "groove" called the "sulcus") and is too uncomfortable for sexual activity in the main.
4} Can retract easily over an erection, completely comfortable. "Extras" are that the foreskin moves back and forth over the glans easily, and possibly even retracts by itself on erection.
So the situations described here are commonly and perhaps evenly distributed over these first three descriptions. You have put
yourself in the second - but only just.
, on average at least, the earlier the classification, the longer it will take to achieve number four, and perhaps the more you might wish to speed up the process by using a stretching device and/ or the betamethasone ointment.
only has meaning if you do something really foolish - which is to say, leave
your foreskin retracted when it is already too tight. This is entirely under your control, so it is not going to happen unless you choose
to permit it - such as be choosing to get drunk, as is often the cause. Otherwise, you just pull it forward again.
"Too much foreskin" is an absurdity - like saying your tongue is too long or your arms are too long.
Discomfort when not using a condom is due to lack of lubrication; which indicates nothing less than poor sexual technique (failing to understand the need - or how - to have the young lady fully "wet" before penetration).
To remedy the tight foreskin - you need to do the exercises we describe here
(including that for the frænulum), not just retract your foreskin. You need to keep
stretching until you are ever so slightly looser than you need, so that the tendency of the skin to "spring" back - which is as it should be - is allowed for.
Sensitivity is not an issue (except of course, as you correctly describe it will
be too sensitive if your foreskin is too tight) - you really
need to understand the importance of lubrication.