WIP outline for a multi-part delinquent TG (parts 3-5)

So uh... I might've lied a bit about this being just 6 parts. Bear with me on it!

Parts 1 and 2 are here! 

PART 3

Begins with the Boss sprinting across a hill in workout clothes. We get an accompanying flashback for context:

A few days prior, he went up to HQ, shocked to see one of his goons needing first aid after he had unknowingly trespassed into another gang’s territory, subsequently the ass-end of an ass-kicking. After getting in contact with the rival gang leader (with the aide as an intermediary), they get into an argument over turf (a neighborhood of the local town, Kingdom Alley), which got into threats, and now the two are scheduled for a rumble -- just a battle between the two leaders so that nobody else is hurt.

Back to the present workout, the boss finally rests near the rec center. He’s in pretty good shape despite that one thing a few days ago that he’s trying to ignore. He considers heading into the locker room for a shower since he’s all sweaty, but then he notices a group of dudes going in after their workout. He decides he can just shower back at home. (significant!)

Back at his own bathroom, he still feels sticky and weird from the sweat, so he takes his shirt off for a shower... and notices his chest looks really really weird in the mirror. His nipples are big and soft, and there’s what looks like baby fat under em... that wasn’t there before. Is he just seeing wrong? He feels sticky and can’t really tell, so he gropes them by the hand--OH!

They’re really sensitive?! He lets go, but just the air around him is making them remain tingly. He tries to fold his arms around his waist to compressing the feeling without touching the bits, and he can feel his heartbeat... and each time, a heavy pulse grows from his chest, and into his... breasts? Are they growing?!

This is where he starts getting really worried, and where he also starts to realize he’s trying not to be aroused by it. He’s getting really horny and tempted to get himself off even through his confusion, before deciding he NEEDS to take a warm shower -- maybe it’s just because he’s been working out that he can’t think right and is paranoid about his body, it’s probably nothing, right?

Cut to a few frame of him bracing through a hot and steamy shower, not used to water on his new female nipples.

“THIS WAS A MISTAKE!!! THIS FUCKING WATER IS MAKING ME EVEN CRAZIER, WHY THE FUCK DID I DO THAT”

Cut to night again, now he’s getting really crazy in bed, hugging a pillow trying to dampen his horniness but evidently that’s not working.

We get a really weird nonsequitur dream: Boss “wakes up” to the sight of an abstract, near-faceless girl (drawn with a smiling mouth but no eyes, as if she’s an incomplete drawing) in place of a sales attendant with no personal space. He’s stuck in what looks like an abstract clothing store, stripped naked and physically forced to try fitting on various dresses and girls underwear. He tries to escape, but then more and more of them show up, until they once again engulf him...

“A FINE GIRL LIKE YOU DESERVES A PROPER FITTING, LET ME ASSIST YOU.L.”

“Get the fuck off me!”

“GIRLS SHOULDN’T USE LANGUAGE LIKE THAT, MISS!”

“That’s because I’m not a girl, asshole! I’m a GIRL! (winces) Shit, not again...”

“DON’T BE SO TENSE, YOUNG LADY. YOU’RE PERFECTLY CUTE. EXCEPT FOR THIS ONE THING...”

“w-wh-h”

“JUST LET IT HAPPEN...”

“PRINCESS...”

One of the women grips HARD onto his cock, and he immediately feels her not “stroking” it, but almost wrenching it, back and forth. He starts to become overwhelmed with pleasure (his body is subtly turning into his present form with breasts), building up, until finally, SPLAT!

He abruptly wakes back up. He realized that his dream was so vivid that it made him cream his pants and sheets, so he awkwardly has to shimmy out of bed and into the bathroom so he can change himself, give himself a quick rinse...

IT’S REALLY SMALL. He tries touching it... it’s barely big enough to fit in his hand anymore. Realizing his chest is still just as weird... quiet freakout time! But first, he gets his cellphone and quickly makes an urgent call...

“Hello?! I know it’s late, but there’s a change of plan for tomorrow!”

PART 4

The next morning, it’s the day of the rumble. Standing before each other are the rival gang leader and the boss (who despite the last appearance seems to look normal in his usual leather jacket?), surrounded by their collective members. The rival looks to stand about a foot taller with a baseball bat, boss has one of them wooden training swords and visibly looks outmatched, but he’s got determination in his eyes. One of the kids acts as adjudicator.

“Alright, gentlemen. We’re expecting a clean fight, no dirty tricks or savagery. You’re each entitled to a weapon and your fists, nothing more. Whoever goes down first relinquishes control of the Kingdom Alley to the victor. It’s as simple as that. Y’hear? May the best man win.”

Rival: “Well, it’s been nice knowing you, kid. I hate to break a young face, but you asked for it.”

The two raise their weapons, boss angry and determined, rival sly and cocky. They make the charge toward the other! Cut to a battle discretion shot with the SFX of very loud sound effects and the sounds of the audience.

(WHOOSH) “WOAH” (PFFT) “OH MY GOD!” (SMASH POW) “SHIT!” (WHOOSH-(POW CRACK) “WHAT THE FUCK?!” (THUD)

Everyone reacts in shock... the boss won, with the rival clobbered and knocked out on the ground. Boss took a blow to the left arm and clutches it in pain (also busted his knuckles from his knockout punch), but otherwise looks alright and is still standing. Everyone on his side immediately comes to his aid, excited that he won and concerned of his injuries, but he coldly tells them to just move on.

“Boss, that was amazing! We got ourselves new turf!”

“Are you okay? That hit to the side looked painful!”

“It’s fine, guys. ssss... head back to base for now. I’ll be letting her [the aide] fix me up at her place. Go.”

The aide responds with a knowing expression that says the two need to be alone. They’re confused on why, but they then agree to it. Cut to later back at the aide’s own place.

“Parents should be out right now. It’s been a long time since you last came here, hasn’t it? Fun!”

The two had arranged doing the post-fight treatment in private, though she doesn’t learn the reason why until he takes his shirt off and realizes he has bandages wrapped around his chest. Aide is both worried and also kinda confused, but when she asks about it, boss just insists she fix his arm first.

“The other guys shouldn’t see this, just get it done and we can talk about it later.”

“You sure?”

“...yeah.”

As the aide wipes his wound, she takes the moment to apologize. Not for seeing him get hurt, but for teasing him before about the whole princess thing, because she thought it would be just a light joke, but seems to be genuinely bothering him. He tries to deny that he was bothered... though he accepts her apology anyway.

"I just wanna remind you that if you wanna talk, your secrets are safe with me. None of the guys have to know this, and if someone asks, I’ll have your back."

(Boss remains silent)

"But know that you shouldn’t have to feel anxious. Everyone already knows you’re a tough cookie! We all like you just the way you are, boss."

theeeeeen just as she’s telling him this, he feels a weird wince in his chest and under his bandages. Just as she leaves to go get the ice pack, he quietly realizes his boobs are getting sensitive again...

ARE THEY GROWING AGAIN?! NOW?!

He tries to adjust his bandages, but fumbles it because of his arm and undoes them a bit, until uh-oh! she sees him and his bare chest!

Maybe she won’t notice?

“Boss... why do you have tits?”

well shit

PART 5

“Are those... real?”

Boss’ unbandaged chest shows he has boobs now, and his aide has full view of them. He’s frozen, wondering what he could possibly explain with, but then she wordlessly walks up to him in curiosity, and pretty much immediately gropes his boob, much to his horror (and lowkey pleasure).

“Huh... small... but definitely real. And really soft.”

(makes eye contact with her deeply uncomfortable boss)

“OH SHIT, I’m sorry! I hope that wasn’t too weird!”

She immediately starts apologizing and rambling to herself thinking why the hell she just thought that was okay, while the boss reacts with quiet confusion; all of a sudden, the aide is more embarrassed about the whole thing than the boss is. After a bit she calms down and they quietly start discussing again:

“Did you eat something weird? Did you get some kind of condition? Are your hormones out of whack? How long did you have those?”

“Uh... not... very long? I don’t know why... they just kinda showed up one day...”

“Interesting... and they seem really sensitive, too. Jeez, no wonder you’ve been so antsy lately!”

“...uh, yeah.”

Out of genuine concern, she asks if the bandages were really helping, and suggests that since his arm still needs time to heal and he can’t properly do them all, she takes him to her bedroom. What follows is a sorta interweaving of present-day and flashing back to when they were much younger, each paralleling the same house. (each probably with a much different color palette)

///

In the flashback, a preteen girl takes a preteen boy by the hand upstairs. The boy is crying into his free arm. He had just gotten into his first ever fight against a bully, and he was really distraught having punched a kid in the face. The girl is a friend who wants to get him to relax, and wants to show him something she thinks will do the trick.

///

The aide guides him upstairs, which he hadn’t been to in a long time. He’s clutching the ice pack to his arm.

///

In her room, the boy blubbers on that he’s finally had it with being bullied for being shy and quiet; why can’t they just leave him alone and let him be himself? The girl offers him a solution: pretend to be someone else! Who might angry bullies leave alone and ignore? If not a shy boy, why not a shy girl instead? As she heads to her dresser, the boy only reacts with a quick “eh?”

///

She lets him into her room, asks her to wait a bit to get something that she thinks will help from her drawer.

///

The girl presents to him one of her school uniforms. The boy is rather appalled -- “that’s for girls!” And she’s like “Yes, you’re right! I’m gonna make you a girl so cute that no bully will ever lay his hands on you! Now take your clothes off!” “GHK--!”

///

She passes him an old sports bra. She preemptively apologizes knowing it must be really embarrassing, but it should compress his chest a bit and should be easy for him to take on and off (it’s probably one of those front-zipper ones that’s not hell on his arm). Boss just takes it wordlessly, but out of a sense of shame (most likely her own), the aide gives him some privacy by hiding in her closet. “Lemme know when you’re done!”

///

The boy slowly creaks out of the closet, having changed into the girl’s uniform, embarrassed but smiling. The dress fits, but the girl thinks he still needs some work, so she proceeds to accessorize him (probably a hairbow, leggings, and her mom’s makeup) while going over details on how to be a girl (thinking of a name he could go with, how to talk, how to shop for clothes, etc.), before finally putting him in front of the mirror. He just sees a cute girl staring back.

///

Boss zips up the bra, realizes it’s probably doing its job (chest feels flatter and isn’t aroused by it), but then sees himself in the mirror. He sees a... startlingly girly figure staring back. A convincingly girly figure, too. He’s confused. He’s both concerned, but in some ways also at peace? And then he realizes all this time, hanging on the back of the door to her room: the dress they originally found at the new house.

///

The boy practices a curtsy as he and the girl go over polite manners (in a very juvenile, obviously inexperienced and cutesy way), and she does his hair. As he’s asked to do a little skirt twirl, he genuinely starts to feel warm and fuzzy at the experience. The girl suddenly hugs him and squees over just how cute he really is. 

He’s warm at first, but the stuff she says about him starts to change his expression from embarrassed realization, to worry, to sorrow again.

(smiling) “You’re a natural at this! You’re so cute and soft... You’ll be so perfect!”

(surprised) “Keep it up, and those bullies will never touch you!”

(anxious) “You’d probably need an actual girls uniform for school, though... we could go shopping together! Oh, we can bring along your big friend -- whatshisface -- and he can be our bodyguard!”

(forlorn) “Agh, we’d need a lot more clothes, there’s so many cute places we can go to... wonder if we could even go to the beach one day...”

(teary-eyed) “Man... I really wish you were a real girl... but the possibilities...”

(KNOCK KNOCK KNOCK)

///

The aide suddenly comes out and sees boss touching the hung-up dress (she heard him zip up and assumed he was done). He’s seized-up, but she’s like “oh, that looks pretty good! Good... flattening, I guess? I mean, I know that should be normal for you, but uh... yeah.” She notices that he’s focusing on the dress again, takes a minute to ponder... then realizes something.

“Man, this must be really familiar to you, huh? Didn’t I once try to uh... put you in a dress as a kid?” Basically, even though this memory had a profound effect on the boss, this is only something the aide vaguely remembers, though she at least has good courtesy to know he might be a little bothered by it. “Oh yeah, I think mom got mad at us for it, hahah.”

He tries to turn away to appear silently disaffected by the dress, but she can tell something’s up. She finally tries to comfort him with her best guess on what his deal is.

“Y-you know, if you actually are interested in it, there’s no shame in taking it out for a spin. The dress, I mean. If you’re really curious about it...

(Boss quietly reacts in blushing shock)

...I called the cousin, she said I could keep it, but like... I can just get back in the closet again for ya and won’t say anything...”

///

“What’s going on here?”

“Oh, hi mom!”

The girl’s mother comes in through the door and surprises the two. The mom is mildly annoyed that she’s fumbling with her makeup, and confused why she invited a new friend without telling her.

“Who is this, anyway? New classmate?”

“Uh... (quietly whispers into mom’s ear)”

“Oh! My mistake, I thought you were really a girl there. Well, glad you’re having fun, nice to meet you... what’s your name?”

“I’M NOT A GIRL!”

The boy angrily storms off with his male clothes past the two, confusing them. He ignores their questions of what’s wrong just so they don’t see him crying again.

///

“--I’m just saying, if you really wanna just give it a shot, and it floats your boat, I’m down with it, kay? You’re the boss.”

(Boss aimlessly stares at the dress, unsure of wtf he’s supposed to even say)

“Although to be honest... I think you actually would make a pretty cute girl, y’know.”

At this point, the Boss has had enough.

“J-JJJ-JUST SHUT UP! ENOUGH OF THIS CRAP, ALRIGHT?!

FOR THE LAST TIME, I’M A G-G-GRHH--!!!!!

fuck it.”

He quickly heads back downstairs as his aide wonders what’s wrong. He apologizes for yelling but just decides to pick up his shirt and jacket and leave, telling her that he’ll see her and the other guys tomorrow, but to forget about everything that just happened before then. She makes no effort to follow him past the door.

“This is complete bullshit! I just hope that tomorrow, I wake up, and this stupid feeling goes away forever...”

To be Continued