I watched his mom dying as Usopp had to lie to her that his deadbeat dad would return to see her one last time in an effort to cheer her up. And when that didn't work he kept making up lies until she quietly passed away.
Usopp was constantly mocked by the rest of the town for the lying habit he picked up after his mothers death. All he ever wanted was the attention of a parental figure but no one in the tiny island town wanted anything to do with him. Until one fateful morning he gathered the courage to go to the giant mansion of the town's wealthiest family and spread his lies there.
After he sneaked up into their garden and met a lonely girl on a swing. She had bright blond hair like the sun itself landed on her hair; she had hazel eyes like that of the many trees in the forest surrounding the island. But one thing was missing from the ensemble: she had a big frown all across her face. One of her bodyguards mindlessly pushed her on the swing as she sat there motionlessly not reacting in any way.
A couple minutes went by as usopp hid in the garden not wanting to be heard. When he figured out the coast was clear he got out of his hiding spot but was instantly noticed by the strange girl.
"Who are you?" She asked in a monotone voice. "I'm the great pirate Usopp and I came here to spread my stories throughout the village!!" Usopp immediately Improvised a makeshift answer 'I'm probably going to get kicked out again' he thought in his mind. She starts shaking slightly, probably stiffing a laugh inside but still asked "Really?".
'She bought it' Usopp rejoiced in his mind, completely oblivious to the situation. "Of course, I have sailed the grand line from start to finish and I wanted to share my discoveries with the people of this town".
"Well Usopp, I'm Kaya Maple, nice to meet you" the girl responded with a shining smile across her face.
They talked until dawn with Usopp making up a lot of interesting locations and tales for the girl. Like a tale of Giants soaring high in the sky fighting hordes of house sized ants, and an island under the sea. Most of these ideas were pulled from the many books that Usopp's father left for him. And Kaya always asked questions about the lore and history of the tales and every time Usopp improvised new paths that shook up the story while still keeping the idea intact.
When suddenly a man with hair like sheep wool asked Kaya to go back inside.
"We will meet again next week!!!" Usopp shouted to her, having finally found a friend. The next memories were of Usopp training with his slingshot in the forest based on his "Omega Ultra Pirate plan", him meeting with Kaya every week and him coming up with all sorts of wacky gadgets.
"WhaT WiLL You Do ? ¡ ! ¿" asked the strange voice of the demon from earlier. And suddenly the memories switched from a normal view to a birdseye one, like I was switching to watching an event play out instead of a memorie . And I started seeing a much older Usopp meeting a strange man in a straw hat, a green haired swordsman with three swords and a ginger haired girl. And then suddenly the scene changes to the four of them on a pirate ship with a weird symbol reminiscent of the one I saw on the collosal wheel. A blond man in a black tuxedo with spiral eye brows now joined the squad as they sailed in a calm sea.
I watched as the straw hatted man stretched his arm from the quarter deck of the ship into the main mast quickly launching himself towards the sheep figurehead of the ship. I peered into the captain's cabin of the ship and saw the ginger girl drawing maps with the blond man fluttering around her with various beverages and desserts. Saw Usopp in a different room makeshifting all sorts of contraptions for his slingshot before going outside to the quarter deck that's full of different sets of weights. And then I saw the green swordsman picking up a barbell with weights the size of himself on both sides and him squatting it while sweating only a little.
And then it hit me, from the strange rubber man to the insanely strong swordsman and all the seas and places I haven't heard of. I finally realized I wasn't on earth anymore. "YoU HaVe AlWaYs YeRNeD FoR AdVeNTuRe" I hear inside my mind "To Be MoRe" and then the memories enveloped me once more.