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Not exactly…after all, it’s not Twiley who’s brushing her feathery wing against her side, but Pinkie. The main part of whether something tickles or not is down to simply whether you know where exactly the tickling sensation is going to take place. With Pinkie controlling her wing, it probably would tickle. :D
Actually, it looks like Pinkie’s using the feather from Twilight’s to tickle her side. Pinkie’s only able to make it work because of her reality-warping powers.
Normally it’d be like trying to tickle someone with their own hand.