I think people have run with this before but... How do you think things would have played out, had Hiccup freed Toothless, but the Night Fury hadn't been crippled and could fly perfectly fine? (These deviations are addicting; thanks for doing all of them! :D)
I think Toothless might have roared in Hiccup’s face and, instead of bounding into the forest, flown off, back into the sky.
Going with the “mind control” theory, he might have taken pause in his flight back to the nest and realize—hedidn’t have to go back. I think he would spend the day flying around, regaining his senses thinking back on all that happened.
He could fly back to his home but… the rage he felt for being enslaved by the Death would fester, and his curiosity towards the human hatchling that freed him—physically and mentally—would grow. Rage and curiosity. That’s what’s kept him around Berk.
So when Hiccup goes back to his ruined bola, contemplating “So why didn’t you?”, Toothless is waiting for him. Watching from the trees. The hair on the back of Hiccup’s neck raises, he looks around. He eventually spots the dark mass high in the boughs. He shrieks and scrambles away. Toothless follows Hiccup, gliding from tree-branch to tree-branch, as the boy sprints back to Berk.
Toothless cuts Hiccup off just before he can make it out of the forest and into the safety of his Viking-saturated village.
For real, I was on the way of doing that last gif compilation when this happened. I had just finished the cropping and had started putting everything together when bam! All the Toms fell into the same frame.
I laughed for so long that I felt that this needed to be shared.