WIP outline for a multi-part delinquent TG (parts 1-2)

Tentatively titled "Who Is The Boss?", I did a note-form treatment and started fleshing it out for Patron consumption... and it's pretty big. I may need to split this among a few posts; this contains 2 parts, I think there are 6 parts total.

tl;dr: the leader of a delinquent gang suddenly finds himself turning into a “princess” physically and mentally (for what may or may not be supernatural reasons), tries to hide it, things get weird for him and his gang as he transitions, but it all works out.

PART 1:

Story begins with a local gang of Japanese-style rabble-rousers, with their leader, simply known as "The Boss". Thinking he’s kinda bishie, probably bleach blonde and already a little cute, but probably also has a scar to let everyone know he means business. Wearing a large leather coat. Actually, he might just look like this guy I previously drew (but maybe a liiiiitle older? also a scar)

He and his crew have just recently commandeered a big old rural townhouse, making it their new base and general hangout. While rummaging through to see if the previous occupants left anything behind, Boss discovers a closet still had a handful of clothes for a young woman, including a dress about his size, as well as hints of other girly paraphernalia like a vanity, leading to a bit where he sees himself “wearing” the dress.

“How the hell does someone just leave a whole-ass dress behind? Especially when it’s so... (turns to sees himself holding it over his body) ...pretty?”

(DOOR SLAMS OPEN) “Hey, boss!”

Suddenly in comes bursting the only girl of the gang, "The Aide", the general adviser/researcher/affectionate brains. Boss is a little embarrassed thinking he was caught doing something undignified, but she doesn’t give him any thought, she’s just like “Huh, they must’ve forgot these clothes while moving. Oh well.” She’s come to invite him to take a look at the backyard; there’s something there.

There’s a small side building that they think might be some kinda tea room, with a lock on the door. But upon snapping the lock off and opening the doors, they realize it’s actually some kinda shrine, probably set up long, long ago. It features illustrations of an ancient royal girl, and etchings.

“In loving memory of our maiden”
“The land has and forever shall be led by its princess”
“may her decree bring peace and love to all”

“Guess you’ll be filling in for her, eh boss?”

“Psh, shut up.”

After that, boss and the rest spend the day moving their stuff into the base.

Cut to later at night back at his apartment, Boss has a dream where he shows up at a royal gala in a badass suit, making his grand entrance to all as he’s celebrated... up until someone compliments his lovely dress... to which he looks down and realizes (SHIT THE FUCK?!), he’s wearing the dress he saw earlier! No nononono there must be some kinda mistake! It was just an accident, he’s not a princess, she’s a princess!!!

wait... what

(grabbing her face and mouth in embarrassment) “No, not a princess, I’m a PRINCESS! I am a... pretty princess... what the fuck’s happening?!

(thinks it out a bit) “This is a dream! Right, I’m just having a nightmare, haha... none of this is real, I’m still me haha, and I’m still--”

A PRINCESS

His dream is suddenly intruded by a vision of a girl... the princess whose face he saw on the shrine earlier. She’s talking to him... engulfing him, letting him feel something really strange down to his core.

“The land has and forever shall be led by its princess... are you not a leader? Are you not a maiden at heart? Are peace and love not what you seek?

“Maiden? What the hell are you talking about, I’m--”

(looks down and realizes his naked body... with breasts, a flat crotch, and long hair. A girl’s body. HIS OWN body.)

“You are perfect. Our princess has returned!”

Boss screams awake, shocked at what the hell his mind just did to itself. He feels his chest and down his pants... still all there... it really was just a dream...

...

...cut to a lingering shot back at the shrine, as it sits in darkness.

PART 2:

A few days or so later during the afternoon, the gang’s all accustomed to their new HQ. Of note are "The Deputy" (a really big, shirtless, but softspoken and kinda ditzy enforcer) and a couple of other goons just chillin’ out in the main hall. The Boss quietly enters the front door and walks past them up the stairs without them noticing.

The boys are just casually dumping some backstory, explaining how they got a hold of this HQ: boss claims he won it from a fistfight duel against another gang leader, though none of them can verify that. They start talking about the boss himself, how they got together in the first place, running parallel to the boss heading to the closet upstairs to see if anything’s still there.

In the backstory, deputy knew the boss when he was younger. He started out in school really quiet and friendless, and often got picked on. Deputy became his one good friend for a while and would protect him (he was big back then too!) but this gave boss the confidence to try and defend himself. He wanted to prove he was tough and learned to fight, to a point that he did get in trouble and was seen as genuinely scary... which is when he started also trying to make more friends. He became close to his current aide, started networking with other lowlives, and sure enough they all met up and became a gang.

They all agree that the boss is has been on the more “quiet” side of tough, a strong leader, and a surprisingly nice guy, but he’s also seemed like he was always unsettled by something, and he's always lowkey stressed and antsy.

“Maybe he’s just like that?”

“Maybe he did something we don’t know of? Did he deal drugs? Set off a bomb? Get a gun and shoot someone?”

“Naah, I know him enough that he’s not THAT hardcore. Honestly, I don’t think he’s nervous with something that he DID, but something that he IS. Or maybe, what he ISN’T.”

There isn’t anything in the closet anymore, and boss reacts with a blank glare.

He comes downstairs and only then do the boys notice him.

“Either way, he’s gonna kick someone’s ass for it.”

(DOOR SLAM)

“Oh shit, hey boss! Didn’t see you come in, how’s it going?”

“Did you guys clean out the rooms? Where’s the stuff that isn’t ours?”

“Oh, ask Glasses, she took care of it, I think she’s in the back.”

In the backyard, boss meets the aide again, and she’s probably doing something innocuous like pruning a hedge; dialogue casually reveals that the house was actually from her extended family who just moved out (confirming the fistfight story was fake) and so she’s maintaining it for them. He asks her if she threw everything out; she threw trash out, but stuff she thinks her cousins left behind accidentally she brought back home, might donate to charity if they don’t want it.

“Oh... yeah, that’s cool.”

(side-eye smirk) “You’re thinking about the dress, aren’t ya?”

“HUH? W-NO.

“Don’t worry, I’ll let you know if my cousins wanted to keep it or not.”

Boss quietly strolls by the shrine again, concernedly looking at the engraving. Aide comes by teasing him for being so focused on it, then explains she did some research on the shrine: the area used to be held by a princess (probably not anyone’s known ancestor), and this house used to be a summer getaway. The house saw better days generations ago back when the figure was still actively venerated, but previous caretakers thought her spirit still resided on the grounds. Not necessarily “haunting” it, but it was still “hers”.

Aide teases him again with the “you’ve been playing close attention to this princess, huh? So responsible of you, boss.” This time he’s a lot more annoyed.

“Will you stop it?! I’m still your boss, AND I’m still a GIRL, and I don’t have time for this princess shit!

“...I beg your pardon?”

“What?”

“What did you say?”

“Huh? I said I’m still a girl, an-”

(realizes what he’s saying, immediately puts hands over his mouth)

“UHH F-FORGET IT!” (runs off back into the house, as the aide looks on in genuine confusion)

Boss barrels into the house, colliding with his deputy (probably carrying drinks for the other dudes lol). “What happened, boss? Looks like you saw a ghost!” “Shut up, everything’s fine! Move it! Thanks!”

He ducks into the bathroom and splashes himself with water at the sink. Looking at himself in the mirror, he tries sounding out the words and realizing he can’t control the words coming out…

“I am a… g… g…iiii… a gi...”

Knock on the door, it’s the deputy again, and he’s sounding really concerned.

“You doing alright? What happened?”

“Uh...” (leans to the side to flush the toilet) “Had spicy food earlier today, no big deal! Just give me a moment!”

“Oh. Sorry to bother ya, boss. Take your time.”

He sits down in concern, realizing something’s gone really wrong. Is something happening to him?

Later that night, he sleeps in his bed. No dream, but he’s very restless and sweaty because of thoughts racing through his head. He’s also not fully covered by a blanket which gives a nice close-up on his chest. Breasts are already beginning to (not quite “grow” yet), but soften and perk up. Without waking up, he still feels something tingly and warm in his chest... and something in between his legs...

TBC...