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2.
A euphemism for anal sex. Usually used amongst furries and dragons.
I once tailboned a bitch, and she cried.

Excessive tailboning can lead to anal seepage.
by thedragon120 March 24, 2010
 
1.
The point of the tailbone is to really hurt when you fall, as a reminder to be more co-ordinated.
*Falls down*

Ow, my tailbone really hurts.
by Bryce Roney October 04, 2007