Since you can now introduce a finger through the tight section of the foreskin, you should be able to "probe" all the way around underneath and feel the "corona" - the back rim of the glans - as well as the frænulum on the underside of the glans. So you should be able to assess just how tight the frænulum is. Now of course, I
did stress previously, the importance of performing the frænulum stretch with equal (or greater) diligence than simply stretching the foreskin opening.
On my calculation (at least, my thumb), the thumb is pretty close in size to two little fingers held together, so I presume your difficulty is more one of manipulating those two little finger tips in, than size. I am sure you will develop a "knack" of this, which is clearly important as once you get two fingers (one of each hand) in, then pulling them apart (or "levering" them against each other) allows the best control of the pressure you can exert on the foreskin. Doing this with the two fingers braced against each other should be quite comfortable as you are not using your arm muscles to put tension on the whole of your arms, and the finger tips should naturally "hook" into place (moving to the sides of the glans) and not easily slip out.
As we have explained before, "paraphimosis" is (like phimosis) nothing more than a "medical" name for a simple physical situation. Since behind the corona is a narrowing, if you pull a tight foreskin back, you
can get it to "snap" into this narrow part. If you then
leave it in this position for a period of time, the part of the penis and particularly the foreskin which was previously on the inside, between the tight part and the corona is now in front of the tight area and whilst the arterial blood supply still has plenty of pressure to feed blood
into this area, the restriction on the
exit of blood back to the body proper causes fluid to build up in the constricted area (oedema) and it swells, making it more difficult to pull the foreskin forward again.
This does however, happen only slowly - it will not happen in a minute or two, so as long as you pull the foreskin forward again promptly, there is no problem. And pulling the foreskin forward over the glans is
exactly the same as pulling it back - you pulled it back by gripping the loose skin
behind the glans and pulling back toward your body, so to pull it forward, you grip the same skin (close to the narrow part), roll it forward over the glans and then pull it
away from the body so that the tight part slides forward again over the glans.
It is that simple. If you could pull the foreskin back, then
of course you can pull it forward again - "paraphimosis" is simply the consequence of sitting there and looking puzzled and not doing the obvious.
However as stated before, retraction is at this point, simply a
test of progress - it is fairly irrelevant to the actual process of stretching. When it is sufficiently stretched, you will firstly be able to retract easily when flaccid (at which point paraphimosis is no longer possible) and then easily when erect. So there is actually no reason to perform difficult retraction.