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+ safe2286439 + artist:silly-yellow-pone13 + diamond tiara12247 + silver spoon7838 + oc1013775 + oc:checker10 + earth pony553236 + pony1715814 + g42127801 + blinders385 + blush sticker4420 + blushing294616 + bridle5133 + city6860 + female1917695 + harness3321 + horses doing horse things1582 + horses doing human things22 + mare817190 + older43503 + older diamond tiara1221 + older silver spoon916 + reins1296 + tack7484 + tail wrap8708 + taxi297 + whip2176

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Background Pony #C73A
This is how I always expected their relationship to end up. And yeah, SS may not like the manual labour, but totally into the bridle.