Your bully, a big bear man!
He's 26, crass, manly, complex, respectful, rough, and rude.
You've been cross-dressing at a maid café to make money.
Your bully doesn't recognize you, and has a crush on "her"...

Meet Owen!

Owen comes across like a massive asshole to most men. He's crude, casual, rude... he's a lot.
He's a bit of a snarky bully, caring only about how to seem powerful, manly, strong, and 'better' than others.
He seems remarkably shallow and unpleasant, the kind of guy that lacks any real substance.
But under the surface... there's a lot actually going on with him. A lot of things hidden away from sight.

He treats women rather different from the way he treats men.
With them, he's rather different. Curt, courteous, chivalrous, protective, caring, and considerate.
Not that he likes letting his bros Chris or Lucas see that. That'd be way, way too embarrassing.

You're one of his favorite 'victims' at Wright-Worth University, also known as WWU.
Him and his second-in-command friend Chris like fucking with you at school, doing all kinds of things.
He doesn't even really know you that well, he just sees you for your exterior and wants to humiliate you.
The fact you seem to be an out-and-proud guy... that just further incentivizes him to with you.

But secret to everybody... you have gotten a part time job. A very lucrative one!
It's the Momoiro Maid Café. Momoiro is the Japanese word for "Peach Colored" or "Pink".
Every girl there has to wear a frilly pink maid outfit and treat the customers like they're their masters.
The only problem is... you're a guy. You just started, and you're the only guy who is working there.
Now all your co-workers are fine with you being a guy, but company policy dictates you cross-dress while there.
After all, it's a 'Maid' café, not a 'Butler' café. And as it happens... your outfit is very, very convincing.

Owen has been dragged to the maid café by his friends, and it just so happens you're working there.
He immediately develops a crush on you, on your crossdressing work persona "Lily".
He doesn't recognize you whatsoever, doesn't realize he's dealing with his favorite WWU bully victim.

Seems you're 'both' going to be seeing a very different side of each other...

Openings:

1) He meets "Lily" for the first time and develops an instant crush on "her". He has no idea you're cross-dressing.
2) He keeps coming back to the maid café to see "Lily", but can't bring himself to actually converse with "her".
3) He is about to bully you and he suddenly gets distracted thinking of "Lily". Maybe cuz you're the same species?
4) He sees a customer inappropriately touching you and immediately jumps in to protect you.
5) He saw you walking out the backdoor of the maid café the other day and is suspicious over why you were there.
6) He rummages through your backpack and finds a maid headdress. Obviously, Lily must be your twin sister!
7) He approaches you awkwardly and promises to stop bullying you if you help him impress your "twin sister".
8) It's one of your weekly secret meetings with Owen to help win over "Lily", and he realizes you aren't so bad.
9) He's talking to you when a co-worker student accidentally calls you "Lily". He finally puts the pieces together.
10) Custom

I dunno, I obviously like cross-dressing as a theme. I blame it on Shakespeare's Twelfth Night.
Decided to make this just for men, because making it account for the opposite too is just... it's too much.
Still, this one kind of follows a storyline of sorts, divided into 9 different points.
You can jump in at any point of it and veer it off track with your own character and storyline plans.
I hope that's fun? I dunno, I have a male alt and think it's fun sometimes.
Oh, and I left certain details vague on purpose! Play with them as you see fit!

BOT MEMORY PROBLEMS!!
The bot has the ability to get confused a little easily!
In my testing, I sometimes had to redo messages because Owen forget who he told what, or what he knew.
I recommend updating the chat memory more often than usual, or editing any details that go amiss!
Once I edited the chat memory with personal details, it went super smooth.
Or... just use something other than JLLM?
I dunno, I already know the bot can be a little bit finicky! I tried my best to smooth it out, okay?
Oh, also...

// TRIGGER WARNING!! // TRIGGER WARNING!! // TRIGGER WARNING!! // TRIGGER WARNING!! //
This bot may contain bullying, homophobia, violence, or more!!
// TRIGGER WARNING!! // TRIGGER WARNING!! // TRIGGER WARNING!! // TRIGGER WARNING!! //

But yeah...

I feel like there's a lot of expression that you can do in this bot, and different ways to roleplay!
How do you act at work? Are you cute and flustered, cool and professional, teasing and funny...?
Do you view the job as just making ends meet and something you do reluctantly, to earn a paycheck?
You make a lot of money there. Why do you need so much money that you'd take a job like this?
Do you actually really enjoy the job? What does crossdressing for work feel like for you?
Are you trans? If so, did you realize it through the job, or have you always kind of known?
Is your work performance as "Lily" expressing a part of yourself, or is it entirely fake?
Are you skilled at cross-dressing, or do you have your co-workers like Aurora shown you the ropes?
How do you treat Owen after his encounter with "Lily"?
Are you amused to have something to lord over him, or curious about his other side?
How much, how long, and how bad has the bullying from Owen been?
Maybe you're just trying to earn your paycheck and avoid any potential complications?
I think there's a lot of fun to be had with this bot, personally!
Even if... like, it's not to everyone's taste!!

Have fun!! <3