I found a question similiar to mine on another site, it's basically the same problems, maybe this will help you guys understand better...
"Even with a full erection, I have a lot of "play" in my foreskin, and can pull it up to cover the head. In fact, during sex, the foreskin tends to naturally partially cover the head anyway, regardless of insertion method.
When discussing uncircumcised guys and condoms, the instructions always say "pull the foreskin back when putting on the condom", and indeed, this feels like the most natural way to do it. But then during sex, the condom and outer skin move up, leaving much of the bottom portion of the penis exposed, and, lacking a solid "anchor", the condom may even be pulled off.
I have heard mention of, and tried, pulling the foreskin up to cover the head, and then applying the condom over that. This anchors the condom securely, but introduces new problems: It's in direct conflict with the instructions, sensation is substantially reduced, and there is now a possibility of "poking through" the condom--I heard anecdotal evidence of this actually happening somewhere on the web.
A third option I discovered is to acquire a very long condom, several inches longer than the measured penis length, and then apply with the foreskin pulled back, roll halfway down, push the foreskin up, then continue to unroll, effectively covering all skin with a layer of rubber. The problem here is that after there is sufficient lubrication inside the condom to separate the skin and the rubber at the head, you end up with several inches of condom dangling off the end, which doesn't seem terribly safe, even though the bottom is securely anchored. Also, since the latex is less pliable than the skin, there can be some degree of "bunching up" of the rubber.
None of these options seems to make a whole lot of sense in the end; I get the feeling that most guys are having far less trouble with their condoms than I.
Any of this sounds familiar? What are your experiences? "
