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Yeah, that’s what I meant. Like, well, a ponytail =p
Or you could fold the tail push the folded end through then stick your finger between the fold and pull the tail should come out through.
I imagine hairs would catch on the edge of the hole and make the tail frizzy if you tried to put it straight through the hole.
Not very hard, I think. Put panties on, pull tail through hole. You wouldn’t “thread it” by putting the tip of the tail through first, and I’d imagine anything but some high-up formal wear and armour would be flexible enough to stretch a bit while pulling through.