Not if you're fast about it.
"Oh! Is... that supposed to happen? Would you like me to pull it out of your tail?"
Luna
Peeking inside of a dragon's mouth seemed like a risky endeavor.
"I fink i almosh god it!" He mumbles around his tail, then suddenly yelps pain.
The tail is yanked out of his mouth, with a tooth embedded inside of the tip.
"Owowow.... finally. That tooth has been loose forever!"