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Tags
+-SH safe2185393 +-SH screencap296763 +-SH applejack201530 +-SH discord37674 +-SH fluttershy259880 +-SH pinkie pie257150 +-SH rarity218512 +-SH spike92704 +-SH draconequus20478 +-SH dragon86115 +-SH earth pony509154 +-SH pegasus501344 +-SH pony1614532 +-SH unicorn543108 +-SH g42041745 +-SH the summer sun setback1221 +-SH cheerleader discord9 +-SH cheerleader outfit1631 +-SH crossdressing12288 +-SH winged spike10199 +-SH wings225804
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Yes
At least Big Macintosh makes a better crossdresser and did once in canon.
I wonder when it is Spike’s turn, or even better, Sandbar’s turn, Sunburst’s turn, Shining Armor’s turn.