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use warnings;
use strict;
...
print "< $line";
$line =~ s/(['"]) (?: (?! (?<!\\)\1 ) .)+ \1/$1SSS$1/gx;
print "> $line";

< Test #1 'Show me Waynes world','Jennys Basketball shoes'
> Test #1 'SSS','SSS'
< Test #2 'Show me Wayne\'s world','Jenny\'s Basketball shoes'
> Test #2 'SSS','SSS'