Anonymous asked:

PLEASE WRITE MORE WINGMAN!TAILS. I NEED IT. (modern or Boom universe i dont really mind)

cutegirlmayra answered:

you have NO IDEA how much I love Tails. And I have a huge HEADCANON that he thinks Amy and Sonic would be a fine couple in his book, but he just hopes Sonic and her will be happy together, that's all he cares about, is their happiness.

Wingman Tails tho… I always have this idea that he would be helping Amy more than Sonic… not only cause she would be kinda… 'forceful' with getting any helpful information out about Sonic, but also because he would feel if he could 'teach' Amy the proper way of winning someone over, it could alleviate stress on Sonic, who ends up scolding him and telling him not to change anybody for him.

So, that's where this story stemmed from. This is also regular canon.

Tails was working along in his shop one day when all of a sudden someone knocked on the door. As he answered it he noticed Amy who was acting 'a little to friendly' as he realized she was trying to figure out a way to get Tails to tell her what Sonic would want in a woman. "Is it attractiveness? Cause I think I got 'cute' pretty much down… what about ability? Cause I can keep up! Oh, Tails, come on! If you won't tell me…" she summoned her hammer.

Fearing for his life, Tails complies, and hopes Sonic doesn't learn about this and think he's betraying him. He begins to teach Amy, 'self control' among other things that will help her be more 'appropriate' when addressing or seeing Sonic.

"Okay, now, I'm Sonic." Tails was wearing a Sonic suit, which made Amy giggle and hold her hand over her mouth, trying not to be rude. "Come on, Amy! You said this would help!"

"I didn't think you meant it!" she burst out laughing.

"Ugh… I'm serious here. Now, do you want him to notice you more or not?" Tails folded his arms, frowning.

"Alright! Alright… hehe, teach me, oh great best friend of Sonic the Hedgehog." she bowed, jokingly, but he got the idea that she was gonna listen.

"Okay, I'm gonna leave the room, and come in, acting like Sonic. You do as I have instructed, and I'll grade you at the end of how well you did."

"Wait… grades?"

"Yes." Tails stated, nodding his head. "And there's a test and three quizes on where his favorite chilidog stands are."

"WHAT!?"

"Hey, you're the one who signed up for this seminar, not me." Tails put his hands up, as if not to blame, as he walked out and dashed back in. "Ah! Smell that freedom filled air!" he tried to act like Sonic, strutting his way in as Amy burst out laughing again. "Ah, Amy! How are-Eee!" He suddenly looked like he was about to dash away, but Amy got up quickly and curtsied.

"Why Sonic! It's a pleasure to see you today!"

"..Huh?" Tails acted a surprised Sonic, and slowly moved his foot down from dashing off. "…Nice to see you too. Huh, that's weird, she's not tackling me. I think I'll stay a little longer, now that my personal space hasn't been violated, so I can feel more comfortable around her." Tails winked as Amy winked back.

"Did you have a fun adventure? Or perhaps you were just racing around? I'd love to hear it sometime! Oh! but on your own time, of course." Amy politely stated.

"Ha! You want to hear my heroic tales! Alright! How about… over some chilidogs?"

"Sure thing!"

"You pass! S rank! Good job, Amy! Now for the real deal." Tails got out of his Sonic suit, but realized it was stuck. "U-…Uh-oh.."

"W-wait.. the r-real thing?!" Amy grew nervous. "What if I forget something? Or lose control? Or-"

"…Why is Tails in a suit that looks like me?" Sonic had snuck his way into Tails's workshop, as he slowly chewed a half eaten chilidog. "I don't remember halloween being moved." he stated, and looked to Amy. "Care to explain?"

Tails decided to not worry about the suit and just motioned for Amy to try something.

She grew nervous, but did so, holding her hands behind her back as to not hug him or anything. "H-how a-a-ar-are you?" she spoke, but the whole time, she was freaking out, having the uncontrollable desire to embrace him.

Sonic looked unphased, taking another bite out of his chilidog and stepping more toward her, testing the limits of what appeared to be 'Tails's training' "I'm fine." he stated, and suddenly rubbed some chili off his face, licking his finger seductively, as Amy fell over in response.

"Tails, tsk, tsk. You should feel ashamed."

"I can explain! She held me at hammer-point!"

"I feel woozy~…" Amy's face is flushed out in red.

"And I call you my best friend. Do best friends tell my other best friends how to act around me?"

"She just wanted to be loved! She was jealous how we always hang out and you and her don't. She wanted to 'normal' enough for you to hang with."

"…Amy." Sonic turned to Amy, as she still lay on the ground, but she tilted her head up to him, cutely doing so.

"Y-yes?" she whimpered out.

He smirked, realizing he had the advantage over her and knelt down, leaning down over her face. "You never have to be anything more than you who you are." he spoke honestly, as she smiled.

"Really?"

"Yeah." he winked.

"Oh Son-"

"-But I like Tails better." He got up and walked away, eating the rest of his chilidog as he waved goodbye to Tails.

Amy had her arms extended out, ready to embrace him before she froze and her eyes widened. She suddenly burst out in rage toward Tails as Tails flipped out, still having the Sonic suit on, and hollered for Sonic to save and forgive him.

How'd you like it? :D