I have always had extremely tight foreskin which, before I started stretching, could barely retract enough to make my penis head visible (while erect). The progress has been great so far but It is not quite stretched enough, but I am hoping it will soon be fully retractable. Recently I have began to wonder whether, once my foreskin is fully retractable, it will retract by itself. Could someone who has been through this process please help me out?

Foreskins are like people. They come in all shapes, sizes and forms. They also react differently with different men. There is no way to predict how yours will behave after stretching.

The thing is, since your foreskin is tight, your erections in the past (including the persistent and frequent ones you have whilst asleep at night) have rather than stretching your foreskin wider, instead stretched it all the longer so that because it is now easily long enough to cover your erect penis, it is likely to do so even when it is loose enough to retract.

Please do not take this as a problem of any sort, it is in fact, anything but. If you are anticipating intercourse, you tend to exude "pre-come" (pre-ejaculatory secretion) which builds up under the foreskin. This means that when you actually proceed to insert your penis into your partner's vagina, as the foreskin is pushed back, the collected "pre-come" lubricates insertion, particularly if she is not adequately prepared and thereby, wet.

A long foreskin - as long as it retracts readily - is not a problem. it will retract on each forward thrust and very effectively provides a "cover" at the vulva which minimises loss of lubrication. Lubrication is an essential aspect of virtually all sexual practices.

Really, the only reason to expect the foreskin to retract on erection, is the frequency with which circumcised penes are portrayed, though there is a strong trend currently for intact ones to be the more common. (Possibly due to material emanating from Russia and outlying states!)