I have been working on the balloon test -- trying not to release early. Sometimes it seems to leak before even half of the head
area is filled up; I'll keep working on that in addition to stretching.
It sounds like you're right about me needing to get my fingers in deeper... maybe. I've never had a problem with my fingers slipping out, but I have experienced a dryness which causes my fingers to stick to the inside of my foreskin which hurts a bit when I remove my fingers. I have read about others here experiencing the same thing.
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.
You're right; I was feeling overly optimistic, I guess.
I have uploaded a group of pictures -- in one image: here
-- which show where I think the tight ring may be. It seems somewhat far back to me, but maybe it's not as strange as I imagine. I'm also interested to know if the pale color of the band as seen in the two images on the right is indicative of a yeast infection or something else. One last note regarding the top left image: I can't pull the skin away at the point shown by the arrow, but I can on either side by pinching a fold of skin.