Uploaded by Background Pony #BECC
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safe2164891 artist:matchstickman416 granny smith6089 anthro357449 g42017173 arm wrestling220 board184 breasts388334 busty granny smith131 clothes630290 digital art29235 drunk5976 eyes closed138074 female1792389 granny smash44 male547289 mare734825 muscles18877 shirt40005 smiling393955 stallion194032 young granny smith812 younger22721

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Background Pony #8456
Maybe she lost to Grand Pear? Although, tbh, I’d rather see her kick his flank.
 
Maybe she lost to Apple Rose?