1. A term in the Furry/Yiff community relating to the "Sonic the Hedgehog" character Miles "Tails" Prower, and placing one's penis in the cleft between his twin tails in order to achieve sexual gratification.
2. Placing's a face between an in between an individual's buttcheeks and blowing a raspberry, as per the traditional "motorboat"
3. Running the tongue along the ass crack.
2. Placing's a face between an in between an individual's buttcheeks and blowing a raspberry, as per the traditional "motorboat"
3. Running the tongue along the ass crack.
1. "I'm not into "tailboating," I'm a Knuckles fan.
2. "I totally 'tailboated' Mr. Hornsby, my math teacher. Now I'm up to a C+."
3. "I walked in on my roommate trying to tailboat himself."
2. "I totally 'tailboated' Mr. Hornsby, my math teacher. Now I'm up to a C+."
3. "I walked in on my roommate trying to tailboat himself."
by BlokeTheHedgehog March 14, 2017
When you take a shit and it leaves a little stain. The entire "boat"(poop) leaves but a little tail of shit left over
"Dude! I just took a massive shit and it left a tailboat in the toliet. I'm hoping this toliet paper will wipe it away."
by Smicky January 09, 2016