Thank you for asking your query at DoctorSpring.
What you are having is a tight foreskin or mild phimosis. This is pretty common among young males. Unless it is troubling you somehow you can just ignore the issue. So what happened during the above mentioned episode is a vaso vagal syncope due to Vagal stimulation - which again is a normal physiological response and nothing to be worried of. When you retract the foreskin the penis got compressed causing pain and stimulation of the parasympathetic nervous system (a type nerves). This has caused the fainting / syncope.
Bottom line, nothing to worry as of now. If getting repeated episodes you may need evaluation.
Hope this helps
PLease feel free to ask followups / clarifications.
Patient replied :
Maybe it's just from my angle, but it seems to me like where the the bottom ridge of the head is, is far down on the shaft. I guess what I'm trying to say is the head looks rather small when the foreskin covers it, but it got (atleast double) the size when it was all the way uncovered. I'm just worried that if I get it all the way behind the head that it will get stuck. Is this also normal?
Yea, when you pull the skin back the head enlarges. This is because of the blockage of the blood circulation by the constricting ring of foreskin. This can be risky at times. (called paraphymosis). You can apply a steroid cream like Betamethasone in consult with your Doctor. This is not exactly abnormal, but a normal variant. If persisting you may require to undergo a minor procedure to release the tightness.
Hope this helps