use warnings;
use strict;

my $line = qq{Test #1 'Show me Waynes world','Jennys Basketball shoes'\n};
print "< $line";
$line =~ s/(['"]).+?(['"])/$1SSS$2/g;
print "> $line";

$line = qq{Test #2 'Show me Wayne\\'s world','Jenny\\'s Basketball shoes'\n};
print "< $line";
$line =~ s/(['"]) (?: (?! (?<!\\)\1 ) .)+ \1/$1SSS$1/gx;
print "> $line";