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the ones that wear my makeup, get jealous of my shoes

Summary:

He chatters idly with the other two as Amy continues getting ready. She’s really going the full nine yards for this date, and Sonic has to say he has a begrudging respect for it. Doing everything she can not only to impress her date, but also to give herself confidence.
That’s what it is, he realises. It’s not for anyone else, it’s for her. To make her feel pretty, to make her feel special.
Sonic watches her go through a clearly memorised routine. Colour on her eyelids, darkening the edges of her eyes, putting whatever-that’s-called on her lashes, and topping it all off with a sheen of gloss on her lips.
“Amy.” Sonic’s mouth moves before his brain can catch up, too fast for his own good, as always. “Can you do mine?”

Sonic is adamantly against putting effort into his appearance for this double date. Shadow won't care even if he does, so what's the point?

...This leather jacket Amy gave him is admittedly really cool, though. Plus, her makeup looks stunning.

Written for Sonic Pride Week 2025 Day 2, based on the alternate prompt: Dress-Up

[Title from BOYS by flowerovlove]

Work Text:

Sonic's jaw hits the floor the moment he steps into the room, pure shock widening his eyes.

He’s only taken aback for a moment before his brows furrow in outrage instead, followed by a strained, half-choked noise escaping his throat involuntarily. Within just another second, his surprise is replaced by rage.

"You told me we'd leave as soon as I arrived, you're not even ready!" he cries, wincing internally at how petulant he sounds even to his own ears.

Amy is standing before her mirror, holding up several outfit options, clearly deliberating. Not dressed up, no make-up on, and not in the slightest bit ready for them to go.

She doesn't even deign to look over her shoulder at him when she speaks.

"I lied," Amy says lightly. She does turn to face him then, gaze narrowing into something wickedly sharp. "I knew you'd come not ready to my standards, so I allowed time for me to make you look at least halfway decent."

Sonic tries to scoff, but the lack of air in his lungs leads to another strangled sound escaping him.

"Okay, first off, I’m clearly a catch,” he boasts, sporting a confidence he doesn’t entirely feel.

Amy’s eyebrows shoot skywards at his words, but she declines to comment.

“Secondly, why are they here?" he adds, gesturing wildly to Knuckles and Tails, who he missed in his initial scan of the room. They’re sitting on the floor, the former looking thoroughly bored while the latter’s eyes ping between him and Amy, tracking whoever is speaking like it’s a tennis match.

"Moral support!" Tails chimes in, despite the question not being directed at him.

Sonic turns to Knuckles to corroborate the story, but they just look slightly dumbstruck before slowly shrugging at him.

"Amy told me to come," they offer weakly.

"They're here to help us with outfit choices and hype us up," Amy announces finally, before turning around to deliberate over her outfits once more. "Oh, and Knuckles will stop you if you try to run from this. I bribed them, so don’t even think about trying anything."

At her words, Knuckles gets up and marches over to stand by the door, blocking the exit entirely with their large frame.

"Seriously?" Sonic asks, but internally kicks himself for not having some kind of escape plan. In hindsight, he should’ve seen some kind of stunt like this coming, and there's no way he's going to get past Knuckles. That thought is only confirmed when he tries to walk towards them, only for them to bodily push him away, without even breaking a sweat.

Sonic considers running, but that would just defeat the entire reason he’s even here. It would be pointless, a waste of time and energy.

Fine, he thinks, I’ll go along with Amy, but not without being dragged, kicking and screaming.

Tails, clearly oblivious to the mood in the room, offers Sonic a double thumbs up, echoing his earlier words, "Like I said, moral support!"

"It’s your fault you fell for this,” Amy informs him smugly. “You never check the group chat. Knuckles, which skirt should I wear?" she asks suddenly, detouring the conversation whilst whipping her head around to stare at them.

Their brows scrunch up as they consider the two options she holds up for their inspection - a shorter, darker skirt and a longer, ruffled one. Knuckles points to the second option.

"Thanks!" Amy beams, before turning to face Sonic and sighing dramatically. "You look no different than normal, and this is supposed to be a date. You didn’t even wear clothes, as usual!"

"Yeah, but Shadow won't notice. Or care," Sonic argues, already thoroughly regretting his choice to go on a double date with him and Amy and her new girlfriend. He should've known she would make it all too complicated in a bid to impress her.

"Yes, but I will notice," Amy replies with a haughty sniff. "Try these," she adds, throwing a bundle of clothing right at his face. Once he finishes spluttering and extracting them off his face, she adds, "There are no trousers in there, but you'd really look better with them on. Just for one night?"

"Yeah, that's never happening," Sonic snorts, beginning to sort through the clothes.

A fear is beginning to grip at his insides, like a fist clutching his stomach and squeezing it tight. An irrational fear, but a fear nonetheless - that these clothes will be feminine (he is, of course, aware that clothes don't technically have a gender, but some certainly scream female to him). These clothes could bring dysphoria crashing down upon him, relentless torrents of it, and there’s no scarier thought to him than that.

He knows Amy wouldn't do it on purpose, of course he does. That doesn't make the fist go away, though - it only tightens at the thought that, if these are feminine, he'll have to pretend it's all okay. Put on a brave face, and act entirely unaffected.

Another thought blooms in his brain. A tiny thought, but one that speaks volumes to him, bouncing frantically around his skull. 

What if Shadow sees him like this, and sees through him? He’s never opened up about his gender; being able to pass means he doesn’t have to, not anymore. He’s not ready to come out on his own terms, let alone someone else’s.

When he looks at the clothes properly, though, the fist loosens. Not entirely letting go, but relaxing significantly, because all of these pieces are either surprisingly neutral, or slightly masculine.

One piece, however, stands out to him instantly. It's a leather jacket in a shade of muted red, with pins littered all over it.

Maybe she’ll only have to drag me kicking, he thinks. Screaming doesn’t seem so necessary anymore.

"Sick," he breathes.

"How did I know you'd pick that?" Amy groans. "I want us to at least be coordinating, that choice is going to make everything so much harder."

Despite her evident disappointment, she doesn’t try to make him change his mind. She accepts his choice without question, which Sonic is immensely grateful for.

He does tune her out, though, to focus on the jacket, on slowly pulling it on. It feels just as restrictive as any clothes do, reminding him once more why he never wears them. Yet, the act of wearing it feels freeing somehow. Despite it being Amy's, it undoubtedly fits him, and not just physically. It feels like him as a person, like something he’d wear.

"You look so cool!" Tails gushes, pushing himself up and coming to stand at Sonic's side. Sonic grins in response, holding out his fist for Tails to bump it, which he does without hesitation.

“I do,” he agrees.

“Your ego shall be your downfall if you are not careful,” Knuckles cuts in with a frown. They don’t scold further, though, so Sonic knows they don’t really mean it.

He chatters idly with the other two as Amy continues getting ready. She’s really going the full nine yards for this date, and Sonic has to say he has a begrudging respect for it. Doing everything she can not only to impress her date, but also to give herself confidence.

That’s what it is, he realises. It’s not for anyone else, it’s for her. To make her feel pretty, to make her feel special.

Sonic watches her go through a clearly memorised routine. Colour on her eyelids, darkening the edges of her eyes, putting whatever-that’s-called on her lashes, and topping it all off with a sheen of gloss on her lips.

Another thought pops into Sonic’s brain. Maybe Amy won’t need to drag me. Maybe I’ll go willingly.

“Amy.” Sonic’s mouth moves before his brain can catch up, too fast for his own good, as always. “Can you do mine?”

She blinks. “Your… makeup?”

Then she grins sharply. Wickedly, almost.

“Not too feminine,” Sonic protests as she begins to grab at her materials, looking as if she’s on a warpath.

“Of course,” she replies, as if it’s the most obvious thing in the world.

Perhaps it is.

Amy clearly keeps it minimal, for it barely takes any time at all. She has to keep badgering him to keep still as he fidgets beneath the tickling of the brush, but in the end they both endure it.

“There,” she says finally with a satisfied grin, holding up a mirror before his face.

Sonic’s heart, previously racing in his chest, begins to flutter instead. Calming down, but still doing backflips in his chest at the sight.

He doesn’t look feminine at all. She’s lined his eyes, but it looks sharp. Everything else is minimal, just a slight enhancing of his features. Only masculine, only him.

“I love it,” he breathes, meeting her eyes. They seem to sparkle knowingly.

“See? Wasn’t it worth coming here early, if only to feel more confident?” she pesters.

Sonic’s face falls. “Well, maybe, but you still lied to me!”

Amy rolls her eyes, getting to her feet. “Whatever, it’s actually time to go now.”

Sonic makes a point of stomping ahead of her, only pausing as Tails and Knuckles wish them both luck.

He only ends up pretending to be mad for about five minutes. He can’t deny the swelling of his heart within his chest, the sheer confidence he feels, like a shiny new armour encasing him, protecting him entirely.

Armour, or in this case, clothes and some makeup.

Sonic doesn’t thank her verbally; Knuckles was right that his ego is way too huge. But he does fall into step beside her, and offer her a small smile.

She looks smug whilst returning it, yet he’s grateful for the response all the same.

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