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i'll pine away forever more for ash davis in drag

Summary:

based on a tiktok from @aintsoluckypuppy ( https://www.tiktok.com/@aintsoluckypuppy/video/7554124182720728327 )
title taken from andrew in drag by the magnetic fields

ash loses a bet, and has to let corey and alex doll him up. tony barges in on the scene, and falls head over regretful heels.

Notes:

hallo everynyan. dont remember when i started this but i finished it at like 9:15 pm 9/26/25

again thank u to @aintsoluckypuppy on tiktok for giving me this idea, i was already writing a beardjacket andrew in drag so expect that later. i guess.

Work Text:

Today had to be THE worst day for Tony. He could hardly find anyone around the safe house aside from Mark, and he had an itching feeling under his skin that something was being kept from him. Or maybe the itching was the annoying rub of some bandages on his abdomen, placed there because of a Russian Mobster getting the better of him with some knife or broken glass bottle or some shit like that. Not that it matters, the dude’s head’s stomped in for all he can care. 

He absentmindedly scratches at his side, over the bandages, wincing at the slight tinge his muscles give him from being sore. He grumbles to himself over the eerie silence of the area, winding up finding Mark again, who’s busy cleaning off the weapons. 

“Tony,” Mark greets, without looking up from his weapon cleaning. Tony would act surprised, but even he could hear his own boots on the floor from a mile away. 

“Mark,” Tony greets back. He leans on the door frame, tensing, and then shifting slightly to relieve pressure off of hidden sore spots on his body. Once he’s repositioned himself, he crosses his arms, trying to seem a shred less irritated than he currently most likely appeared to be. If it worked, it was beyond him. “D’y'know where everyone else is at? The place is too damn quiet, and I wanna make sure they all didn’t get their heads blown off or something.” 

If Mark picked up on the underlying tone of caring in regards to the other Fans, he made no comment. He offered a hum in response, before verbally replying. “I think they’re off in one of the lesser used bedroom-turned-storage room? Last I heard it was Corey and Alex dragging Ash to there. Something about a dare, or a bet. Either way, that’s where you’ll find them.” 

Tony huffs and stands back up, uncrossing his arms. “Thanks,” he simply replies, Mark humming a response. He turns on his heels, and heads over to the room Mark mentioned, mentally simmering what Mark had said. 

‘Something about a dare, or a bet’...? The fuck could that be about?

As he furrows his brows in thought, he hears the other three behind a closed door. With little care for what could possibly be on the other side– sue him, before this he had no idea where the three were– he’s greeted with an interesting sight.

And his stomach doing a small flip. 

He’s greeted with Ash sitting down in a chair, both Corey and Alex humming and hawing over his appearance– his wig, makeup, and outfit– with Ash taking first notice of Tony's sudden appearance.

“Jesus, Tony, knock damnit!” Ash shouts, covering his face with his hands. Both Corey and Alex turn around, spotting Tony. 

“Tony! How do you feel about Ash’s new look?” Corey walks over, leaning her elbow on Tony’s shoulder, despite the height difference between them. 

“Ash, move your hands, I’m not finished-” Alex gently scolds, Ash dropping his hands in his lap in defeat, before she turns to look at Tony and Corey. 

“Ash lost a bet, so now he’s gotta let us doll him up! Yeah, what’re your thoughts on his look?” 

Tony feels like his feet are made of lead. Scratch that, his entire body feels like lead, and his feet feel like tungsten. He’s stuck looking at Ash, who’s currently donning a brown wig, heels that are absolutely Alex’s, and a dress that’s a half-size too large for him, probably Alex’s too, with a shirt stuffed down to fill up the bust of the shirt. 

He feels like he’s head over heels for Ash. 

Head over heels for Ash in drag. 

He forces words over his tongue, making some comment about Ash looks “fuckin’ silly,” and a question about the bet, desperately trying to mask his infatuation for the man in drag sat not but three feet from him. 

Corey and Alex talking sound more like background noise than anything, though he desperately tries to hang onto what’s being said. He keeps glancing back at Ash, every glance catching a new glimpse of something new. 

The way that his makeup accentuates his eyes. How the dress seems to fit him, even if it’s nothing he’d wear. The wig framing his face almost perfectly. How the color of everything fit him practically perfectly

He comes back to reality with Ash’s hand snapping in front of his eyes, before it gives a wave. 

“Helloooo…? Earth to Tony, Earth to Tony?” Ash cuts through the static, making Tony very strongly aware of the way his heart’s beating too fast for this to be normal, and how utterly stupid he must look in this moment. 

He’s most definitely having romantic feelings for one of his compatriots-in-arms, someone he’s fought next to and nearly died by several times, being hit with them like a brick thrown to the skull by seeing this man in drag. A man who is most certainly not interested in him, and never will be, hell he’s probably straight-

“Tony, dude, seriously. You good??” Corey appears in front of him, both Alex and Ash hovering behind her, a gentle hand set on his shoulder. 

Tony blinks a couple times, shaking his head slightly and grounding himself in the present. 
“Yeah, yeah. Yeah. Sorry. Lost in thought,” he hoarsely replies, and the expression Corey gives him is indicative that she can tell there’s something more, but not to push. 

Alex seemed to pick up on Tony’s underlying message, and changed the topic. “Don’t ogle for too long, we still gotta show Mark. I think Ash’s about ready, yeah?” She asks Corey, who gives a nod and a smile. “You wanna come with?” She asks Tony, who shakes his head and makes some comment about needing to go to the bathroom.

The three of them head off to go show Mark the result of the lost bet, while Tony immediately booking it to the nearest bathroom. He shuts the door, locking it, then turns to face the mirror. He white-knuckle grips the porcelain, the cool temperature doing little to soothe the fire of shame under his skin. 

He stares down at the metal faucet, seeing a warped reflection of himself staring back up at him.

He couldn’t possibly like Ash. He couldn’t have realized it when the man was dressed up in a wig and his sister’s clothes. What bothers him deeply is if he wanted a chick, he’d just date Alex. But he feels nothing for her, nothing romantic. What about Ash in drag is making his metaphorical tail wag? It’s not like he does like the man, Tony’s probably just confused!

He looks up and glares at himself in the mirror, noticing the flush of his skin. The beating of his heart loud in his eardrums, and the stupid fucking thoughts of Ash in the wig and heels, looping in his mind. He grips the sink harder as his brain helpfully presents him image after image of Ash all dolled up, each one causing Tony to get very slightly more flushed and flushed, before his brain decides to present him with the concept of the two kissing. And that’s when his thread snaps. 

He mindlessly swings at the mirror, punching it with enough force to break it, pulling his fist away and ignoring the sting of his knuckles in favor of staring at his now-broken reflection, a shattered version of himself staring back at him. 

He unlocks the bathroom door and walks out, bee-lining straight to a private room, but not before catching a glimpse of Ash, their eyes meeting, a look of almost-pity on Ash’s face. 

Tony glares down at the floor as he feels his heart skip a beat at the mere shred of an idea of Ash caring about him. 

He was stupidly head over heels for Ash in drag. A woman he’ll never meet again. 

He didn’t leave the room for the rest of the day.