Cover art by tailchana
Sonic had a problem. Okay well, Sonic had many problems, but this one was particularly annoying. He was supposed to like Amy. I mean, like like her.
But he didn't.
Sonic had been trying to get with Amy for years, more accurately he was trying to convince himself to get with her. But no matter how many times he told himself that she was pretty, no matter how hard he tried to stare at her boobs, he just couldn't force himself to find her attractive…
That's where Tails came in!
"You want me to what?" Tails asked, staring at Sonic in confusion.
"I want you to roleplay as Amy so I can work up the courage to ask her out!" Sonic explained, smiling as if it were a completely normal request.
Tails blinked once. He blinked twice. Then he burst out into laughter, guffawing and hugging his stomach.
"What's so funny!?" Sonic asked, crossing his arms.
"You want me to roleplay as Amy!?" Tails wheezed.
"Well, yeah! Look dude, I need to ask her out! I've been trying for years, but I just can't work up the courage."
"Wait, I thought you didn't like Amy like that?" Tails asked, wiping a tear from his eye.
Sonic gaped. "Why do you think that?" he asked.
Tails looked thoughtful. "Because you always run away from her? Because you never show up to dates with her? Because you literally shove her away when she gets near you?"
Sonic cringed. "Oh. Was it really that Obvious?" he shook his head rapidly, then glared. "Look, I just need you to do this one thing for me! I do stuff for you all the time, so what's the big deal?"
Tails held up his hands defensively. "It's not, really. But why do you think roleplaying with me will help you become more confident around Amy?"
"Cus you're my best friend and I've seen this kinda thing work in movies!" Sonic said.
He clasped his hands together before his chest, pleading and whimpering.
Tails chuckled, then stood.
"Alright, just hold on one sec," he said, before turning and entering his bedroom upstairs.
Sonic was left sitting on the plush orange couch for a moment, then his ears perked as Tails made his way back down the stairs.
"Okay, what was so important that–" Sonic froze, his mouth fell agape and his eyes bulged.
Tails came down the stairs wearing a red dress and boots just like Amy's, complete with a headband and everything.
"T-Tails!?" Sonic asked, his heart beating faster.
"Not Tails, I'm Amy for today!" Tails said, at least his voice was the same.
"Why do you even have that!?" Sonic asked, hopping off the couch and taking a few steps back.
"Some questions are better left unanswered," Tails said, smiling brightly. "So, Sonic, you wanna go on a date?"
Sonic blushed, then gulped. "Uhh… Sure thing, Amy. But uh, are you sure you're comfortable going out like that?" he asked, scratching his head.
"Yeah, it's fine. I don't really care what other people think," Tails said, his cheeks tinting pink.
"Oh-Okay then…" Sonic said, staring at the ground bashfully.
A moment passed, then Tails piped up. "So, where do ya wanna go?"
Sonic sucked in a breath,then exhaled slowly. This was his idea after all.
"Let's go to the park first, then we can go to the carnival and then out to dinner?" Sonic suggested, peeking at Tails from the corner of his eye.
"That sounds lovely, let's go!" Tails said, as cheerful as ever.
Sonic gulped, then looked at Tails again. He wasn't sure why his heart was beating so fast, maybe it was an instinctual reaction to Amy's get-up? But it felt different this time…
Sonic quickly swept Tails off his feet, holding him bridal style. Tails eeped, then the two were out the door in a flash.