But of an ego boost when you have to tell her that the condom is too small, and yes it has happened to me. Usually gets a very positive reaction.
But you're right about the stretching it to get it on. Perfect technique is to use her mouth of course and make it part of the experience rather than a necessary evil. Had a couple of girls who say they don't like the feel of them and asked me to put it on my self. Bit like going into Kwik Fit and fitting your own tyres!!