Not only couldn't she manage to put the first one on, she couldn't even get the second one out of the foil, which begs the question, if she is so unused to condoms does she usually do bareback?
She also tried to put the first one on while I was only semi hard, and failed, so I told her I had a large size condom in my wallet because I am a bit thicker than average, and she asked, in all seriousness "Oh, does it get bigger when it gets hard?"
Really, I swear to God I am not making that up, a supposedly experienced WG actually asked me that!