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No one could call Tails dumb or stupid, despite his age, but they did call him unobservant, especially when he begins tinkering on a new invention. Which, is partially true. Most of his focus goes to the projects, but he never stops listening, observing, gathering information. He can't stop really, it just comes to him naturally. It came in handy though, everyone lowers their guard around him, letting secrets slip accidentally, gossiping just within ear shot, acting different. He always saw.
As such, when Sonic began crushing on Amy, he knew, maybe even before Sonic did. He knows Sonic, every part of him, and is intuned to his normal antics. So when he began staring just seconds too long, he caught it. He saw how protective he'd become over her, always planting himself between Amy and their enemies. He kept close to her as well, hovering nearby on walks, staying as close as he could during fights, sleeping beside her on their many adventures. Not with her, there's always a respectable distance between them, but Tails can see it closing slowly.
He also knew when they started dating, in the middle of fall, but he kept quiet, acting surprised when they finally announced. He'd seen their shared looks, the lingering contact like a too long pat on the back or a loving shoulder bump. The extra note of worry when either got injured. They couldn't hide anything from him. The one time he was surprised was when Sonic took him aside one day, whispering about some super secret project. His mind went to the usual suspects, a new weapon, upgrades to Tornado, something equally stupid, but fun. Turns out, it was a marriage ring.
He'd blinked at Sonic, a little lost for words, but then he catches his thoughts and they immediately begin planning. Unfortunately, the Hedgehog was horrific at any sort of inventing, but he instructed Tails on everything as he made the rings. Two solid gold bands, each embedded with a diamond of the other's color, it took them nearly five months to make them, most of it was spent finding the right gems and enough gold. Then they had to measure Amy's finger without setting her off, which was way harder then it should've been, only then they could finally start constructing them. Sonic was torn between having some sort of etching, or not, but eventually decided to keep it simple, but elegant.
Tails helped him plan everything. Where Sonic would ask, when, making sure nothing bothered them as they went on their scenic adventure. He watched them, couldn't help himself, practically vibrating with anticipation as Sonic got down on one knee. Amy squealed, crashing into him with a resounding yes. They both tumbled to the ground, laughing. Tails smiled at them, but when a shout rings out, he takes off. Nothing was going to ruin this, nothing.
He was apart of the wedding plan by both parties. For Sonic, he helped him with locations, guests, and budget. With Amy, they talked decoration, attire, and food. It wasn't extravagant, a simple forest wedding surrounded by friends and family, but it was beautiful. The aisle was littered by flowers petals, padding her soft paws against the harsh ground. It lead to a wooden arch covered in vines and dangling flowers, Sonic, with Tails right beside him, both in their best. Cream and Cheese walk Amy down the aisle, each on one side of her, and even Tails lost his breath that day. She was dawned in a soft pink gown, intricate lace crawling up her skirt and arms, flowers of all kinds sewn into the hems, making a waterfall pattern down her side. She holds roses, reds, pinks, and spots of blue, in her hands.
Tails couldn't stop himself from crying as they exchanged their vows, discreetly trying to wipe them away as they kiss. Everyone cheers, sending birds scattering to the sky as the celebrations begin. The reception is deafening, everyone laughing, dancing, singing, talking, there's no end to the sounds. He stay focused on Sonic and Amy, keeping an extra eye on Cream and Cheese as they dance together. The food is lavish, plenty, and hearty. Seemingly never ending fruit bowls, meats of all kinds, a plethora of soups that Amy refused to budge on, and, of course, chili dogs that never stopped.
The celebrating went all night, only stopping when the sun's first rays began to brighten the horizon. After that, Sonic moved in with Amy, and things went mostly back to normal. Eggman still attacked, they still argued, and Tails was still stuck playing mediator. He didn't mind honestly, they'll always make up. Then Amy started acting different, and he noticed. How her nose would wrinkle at breakfast, she even refused to eat a few times. He'd caught her rubbing her chest, as if it was sore, and saw how her emotions were unusually heightened, even for her. Naturally, Tails saw the writing on the wall, but he still cheered when Sonic and Amy announced their pregnancy.
It'd been winter when they announced, calling everyone to their home with promises of warm soup and hot chocolate, how could they say no? So, they trudged through snowy Green Hills, and after enjoying Amy's homemade potato soup, Sonic got all their attentions. He stood, hand in Amy's as she stands beside him, and Tails catches on instantly, placing his bowl down. They share a look of joy and anticipation, before shouting at the same time. She's pregnant. Everyone cheered, gathering around to congratulate them and discuss the news. Sonic pulled him into a shoulder hug.
Months passed, and Amy grew bigger. Like, maybe too big honestly. The last month, she was forced on bed rest, much to her dismay, and Tails kept her company most of time as Sonic fought off Eggman. He made her atrocious sandwiches, just thinking about them makes him shiver, helped her waddle to the bathroom and the living room. He even tried to help her knitting, but that only ended in disaster. She'd patted him on the knee comfortingly, lying nicely about how good his hat was, but Tails knows when he's made a bad product. She still has that hat, framed on their bedroom wall, right next to their photo right after the birth.
The birth was nerve wracking for everyone, Sonic refused to stay still. Thankfully, they let him in the delivery room, leaving Tails, Knuckles, and their closet friends right outside. It took all day and night, Cheese and Cream had slept tucked against him, and, a little embarrassing, he'd fallen asleep while leaning against Knuckles. He was startled awake by yelling, a moment of silence, and then a baby cries and everyone rejoices. He hugged Cream so tightly, he almost missed the extra shouting. Everyone goes quiet again, glancing nervously from one another.
Another baby wail, a different one, and someone shouts twins. Big spins him around and Tails laughed as the begin celebrating again. They calm down half an hour later, when Sonic comes out, smiling from ear to ear. His hands land on his shoulders, squeezing, and asking him to come meet his nieces. Nieces. Tails spins the word around his head as he follows his brother, trying to remember everything he knows about newborns while also trying not to jump and shout because he was an uncle, of two! Amy looked worn out, almost drained of color, but she's smiling, cradling two bundles to her chest.
Slowly, Tails comes over, suddenly too aware of everything. How germy he must be, how it reeks of blood both new and stale, Amy's strong breathing, and the cooing of babies. Sonic takes one of them, eyes so full of love, and shows Tails how to properly hold Poppy. Poppy. Tails had no idea what names they chose, but as she's placed gently in his arms, he decides that it's perfect. She's so tiny, eyes closed shut, and Tails feels himself shaking. She's a light blue, much lighter than Sonic's signature colors, but she has Amy's nose, her lips, the curve of her eyes. She also has Sonic's cheeks, his dimples. Tails couldn't stop looking at her.
Then the other baby gurgled and he's shocked back into himself. He hands Poppy back to Sonic and takes his other niece, Dash as Sonic decided, from Amy. She's almost an exact copy of Amy. The same shade of pink, the same face, though her quills are longer like Sonic's. She's smaller than Poppy, almost swallowed by the yellow blanket. He smiled softly at her, committing everything to memory. His nieces were perfect, healthy, and strong. He'd never felt so happy before.