Recently, my son has begun asking me to play Dungeons and Dragons with him. He's six now, and remembers a bit of free-form play we did on our morning commute to the kindergarten two years ago. He suffered from a lack of linguistic ability then (one drawback of raising a multi-lingual child is that development in each language is slower at first compared to a monolingual child).
Anyway, now his English is closer to native speaker level (give him a couple more years), and he's more cognitively developed. When we free-formed two years ago, he would make interesting choices (fight the dragon, run away from the skeleton, things like that...hey, skeletons are scary!). It was refreshing to me to see his actions/reactions through fresh eyes, without the baggage of nearly thirty years as an RPG gamer that I have.
Last year, he didn't like the free-form improv, but did enjoy pulling out my old Dragon Strike board game and moving his piece around the board (usually the Wizard), pretending to fight monsters with my wife and I as companions. He also loved playing Pixel Dungeon (a free Rogue-like) on my smart phone.
Anyway, in the past week or two, he's been asking nearly every morning to play that improv style game again, along with nights and weekends. A few months back we tried playing some actual D&D by the rules, with dice and maps and everything. He enjoyed it, and this current round of free-form play started with his new character, the Fighter Stinky-Feet, avenging his previous character, John Jacob Bibbybobby, who died fighting a bone golem (and who had avenged his first character, Wizard the Stinky-Feet).
His new character has managed to recruit some allies (knight, sorceress, thief, and Sloth) by releasing them from magic mirrors, find the pirate treasure of One Eyed Willy, battle goblins/orcs/hobgoblins (and run away once the alarm was sounded and his group was outnumbered), explore a mummy's pyramid, raid an ogre's castle, put a ghost's spirit to rest in a haunted tower, sailed to the Ghost Kingdom to rescue Bibbybobby's spirit, and more! He's made it to Level 5 by now! (Level advancement is at the hands of the arbitrary and capricious DM, of course.)
While he's apt to suddenly declare his character to have certain abilities ("I speak Egyptian, so I say to the mummy...") or items, for the most part he's using clever ideas to deal with challenges and traps, although he usually just battles against the monsters.
We use rock-scissors-paper as a resolution mechanic, by the way.
Tonight, he wanted to go to the Dragon Mountain. I described the mountain with five caves, each the home to one of the standard D&D chromatic dragons. The green dragon was his first target, but it surprised him, and after breathing poison gas (and losing the rock-scissors-paper), he found himself nearly dead. He decided to try talking. The dragon demanded his treasure and magic sword, which he surrendered in exchange for his life.
Undaunted, he went back to the blue dragon's cave, but gnomes allied with the dragon convinced him not to fight it. His third attempt was the black dragon's cave, and due to some unlucky "rolls" his knight companion died to acid breath. He and his other companions escaped.
He handled the setbacks well. "Dad, if Stinky-Feet dies, I will make a new character." That's the spirit! During dinner, he then managed to defeat a Man-Bat (like from Batman comics), and just before his shower a giant (buy building a giant punching machine and getting the giant drunk before the punch).
In addition, I've been making up these dungeons and adventures for him on the fly. Several of them might make good one-page dungeons, or at least interesting locations in a sandbox game. As I say in the title of this post, i should write them down! And by posting this, I'll at least hopefully have enough down here to spark my memory when I finally get around to it.