Rainbow Rocks 10th Anniversary - Let's celebrate the 10th anniversary of Rainbow Rocks with an art event! Here
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PwnyPony
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@The Smiling Pony  
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.
The Smiling Pony
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Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
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( ͠° ͟ʖ ͡° )
@Background Pony #9866  
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.
Background Pony #AD07
Could you imagine what a chore it would be to thread your tail through those kinds of panties? If we had tails Apple would already have invented panties with magnet connectors.