First Flight takes place a few years before Sonic the Comic's main continuity begins. Tails' peaceful stroll through the Nameless Zone is ruined one day by the resident bully, Witless Chris and his gormless sidekick, Scratchy. Witless calls Tails a variety of rude names, and labels his extra tail as useless. As the despondent Tails beats a hasty retreat, Witless' bragging to Scratchy about fighting bears is noticed by Sergeant Claw and Captain Tooth, who are hiding nearby and have decided that Witless is a perfect contender for their Arena of Doom. While Claw reckons that Witless is lying, he thinks he'll still give the crowd a good show, and soon the bats have captured Witless. Tails has noticed, and wants to save Witless, because 'even a moron deserves help'. Unfortunately, Tails stumbles off a cliff, and plummets down, his tails whirling. He quickly realises he can fly, and soon attacks the bats, freeing Witless, but can't catch the bully in time to stop him falling into a muddy creek (but may have let him land there on purpose). Tails pulls the apologetic Witless out of the mud, and is set to start making his own stories from here on out.
- Tails' revelation about being able to fly is convenient, to say the least.
- The Nameless Zone seems to be a lot brighter and leafier than in its other appearances, much resembling the greener Zones of Mobius.
- Witless' remark of 'battling six bears each morning before breakfast' is similar to the Queen of Hearts' statement of 'sometimes I've believed as many as six impossible things before breakfast' in Alice in Wonderland.