I enjoy having my cock squeezed, mainly when I'm cumming. I like to be held with a firm grip (with maybe a little pulsing) until I finish cumming. I can cum without it, though.
I have heard of this before. I think it's because of not much sensitivity in the penis. I've heard this can happen as a result of circumcision, or can be brought on by too much "rough treatment" of the penis (like during masturbation). Fortunately, if it's the latter, the effect is temporary and you can regain the sensitivity.
Unfortunately, if it's from a circumcision that leaves little, if any, loose skin, I don't think much can be done. This is why, if I ever have sons, they are NOT going to be circumcised, unless they decide to have it done after they're grown up. Sorry, I didn't mean to wander into another topic!