I think you need to get your fingers fully inside the foreskin so that they lie beside the glans on either side. This for two reasons; so that you know you have identified and are putting the pressure on the tight area, and also so that by "hooking" them in, it is easier to apply the pressure for extended periods without them slipping out.
This of course applies equally to using a stretching device - the inner flange of the device must be fully through the narrow part and alongside the glans.
Because of those regular and frequent erections that you have been having every night since birth (and before), the foreskin over the glans is already stretched to accommodate it in the erect state even though the glans is never as firm as the shaft of the penis. There is therefore, always the space next to the glans (at least when flaccid, but because of the regular stretching, there will be plenty of elasticity to allow extra space when erect also) for your fingers to enter, though you really do need to fully evaluate by the "balloon test" that this part of the foreskin has separated back to the sulcus.
Again, I have to reject the notion that this matter is in any way responsible for your prospects or lack thereof in finding a young lady. It really is quite irrelevant.
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