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Tags
+-SH safe2183266 +-SH screencap296509 +-SH applejack201347 +-SH discord37659 +-SH fluttershy259652 +-SH pinkie pie256930 +-SH rarity218345 +-SH spike92651 +-SH draconequus20454 +-SH dragon85978 +-SH earth pony507996 +-SH pegasus500321 +-SH pony1611952 +-SH unicorn541903 +-SH g42039217 +-SH the summer sun setback1220 +-SH cheerleader discord9 +-SH cheerleader outfit1630 +-SH crossdressing12277 +-SH winged spike10184 +-SH wings225176
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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.