Bonnie Rockwaller

"Alright, ladies. Gather around. You may not have heard, but I'm going to be the new Cheer Coach here at Middleton. I'm looking forward to getting to know all of you."

Bonnie Rockwaller's eyes widen at the sight of the wealthiest man in all of Middleton standing there, waiting for them all. She quickly whips her head around, wondering if this was Kim's doing, but her rival for the position of Cheer Captain (and also the current Cheer Captain, much to Bonnie's consternation) looks as surprised as the rest of them. Even more so in fact, and she's the only one among then save for Bonnie herself who looks a little annoyed and concerned, even.

"Mr. Lipsky! Is this for real? But you're like, a total big shot in the business world, aren't you?"

That's Marcella, always the most financially minded of the team. Still, she's asking what most of them are thinking at this point, and Bonnie can't help but be a little pleased that she's not having to do the talking. Chuckling, the billionaire standing in front of them nods his head, even as he shrugs.

"Yes, yes. Not to toot my own horn, but I suppose I'm a fairly wealthy man. That said, I'd rather we not focus too much on that…"

"I heard you own Club Banana!"

"I heard you've got a dozen summer homes across the European Countryside!"

"Is it true that you have a jet?"

"Is it true that you have a yacht?!"

CLAP!

The Middleton Cheer Squad jumps at the sound of Mr. Lipsky clapping his hands together sharply in order to silence them, Bonnie included. All of them stare at him, slightly wide-eyed as he gives them all a smile. For the first time, Bonnie notices just how… handsome he is. Which is strange, he's always just been this rich dude (richer than her family, even) who went and married Kim's mom and became her stepdad.

"That's enough, ladies. Let's change things up, shall we? When I'm here, working with you all, I want you to address me as Coach Drakken. Mr. Lipsky and all that comes with that gets left at the door. Yes Kimberly, that includes our relationship as well. Are we clear?"

There's a chorus of 'Yes sirs' from the girls in the room, even Bonnie muttering it under her breath. However, the majority of the slender but curvy brunette's attention is on Kim Possible, watching her go ramrod straight as Coach Drakken addresses her directly, and then actually seeming to relax as he assures her that their relationship of stepfather and stepdaughter will have no bearing on his coaching of the Cheer Squad.

It's… interesting, in Bonnie's opinion. Interesting to see how Coach Drakken acts, despite his 'secret identity' as one of the wealthiest men in the world. Hell, her parents couldn't talk ENOUGH about Mr. Drew Lipsky. The things he was doing in the business world, the inventions his company was putting out in almost every field… he was revolutionizing everything, if her parents were to be believed.

But it seemed like he was looking to get away from it all by coaching the Middleton Cheer Team, and Bonnie… Bonnie figured that was just fine. No, more than fine… maybe there was some way she could use this to her advantage.

With Coach Drakken's introduction out of the way, the girls all get started on practice. Their new Coach doesn't say much as the practice continues, but he's always there, always watching them. Bonnie actually kind of likes it, every time his eyes go to her. It's like she can feel his attention… and his attention feels good. On the flip side, he doesn't spend the entire practice staring at only her. His attention is divided between all of the girls on the Cheer Team, to Bonnie's growing chagrin. Even as Kim leads them through their routine, Coach Drakken isn't picking favorites.

What if she could convince him to do so though? The thought doesn't come out of nowhere… it's been percolating since he made that remark about not favoring Kim just because he's married to her mom. Kim might be the Cheer Captain right now, but if Bonnie is being honest… she's always wanted to be Cheer Captain. And the only one who's ever stood in her way was one Kimberly Ann Possible.

Maybe Coach Drakken was the key to changing that. Maybe, just maybe, she just needed to get in good with him, make him realize why SHE should be Cheer Captain, and then she could finally toss Kim from her stupid throne. To wipe the smug look from that bitch's face and finally put her in her place… god, it'd be delicious, wouldn't it?

Eventually, practice comes to an end. Coach Drakken didn't actually do much coaching, and yet, neither Bonnie nor the rest of the girls actually mind all that much. He holds the door open for them and compliments each of them on a different part of their form as they leave, putting big smiles on each and every one of them as they head for the girls' locker room.

To Bonnie, he tells her that her splits are phenomenal, and she can't help but beam, deciding then and there to put her plan into action. Stopping, having already made sure she would be the last one out, Bonnie turns to Coach Drakken and bats her eyelashes prettily.

"Actually, sir… I was hoping that I could talk to you in private, really quick. If you don't mind?"

Raising an eyebrow, damn was he handsome, the new Coach shrugs and nods, closing the door of the auditorium behind them and walking back inside with Bonnie at his heels. Sitting down in the bleachers, he looks to her.

"Bonnie, wasn't it? What can your Coach do for you?"

Licking her lips, Bonnie nods as she steps closer to him, her hands clasped behind her back and her chest jutted out as she twists this way and that with a smile on her face.

"Yes sir, Bonnie Rockwaller, sir! I was hoping to talk to you about the position of Cheer Captain!"

Lifting his other eyebrow, Coach Drakken hums as he crosses his arms over his chest. Bonnie's immediate impression of them is that they're a little scrawny… but then she blinks and realizes she was mistaken. His biceps are big and strong, just like the rest of Coach Drakken's handsome physique.

"Is that so? What about it? From what I understand, isn't the Cheer Captain position awarded through a democratic process?"

That's true, and Bonnie has been working hard to slowly make inroads with the rest of the team. They all elected Kim because she was the best or something, because she was a famous crimefighter… but given enough time, Bonnie had been sure that she would be able to convince a majority of the other cheerleaders to dethrone Kim for being consistently tardy and tired because of her world-saving side gig.

But, what if she didn't have to convince all of those other girls to back her up for the position? What if she just had to convince one person… the person seated right in front of her.

"That's true, sir… but we also didn't have a Cheer Coach until today either. So, the way I see it… it's a new dawn for the Middleton Cheer Squad! Why not a new Cheer Captain, to go with our new Cheer Coach, right?"

Bonnie grins and bats her eyelashes, but Coach Drakken isn't so much as phased by her cutesy act, she can immediately tell. He chuckles instead, like he finds her attempts amusing, and it rankles something fierce, even as she hangs off of every word of his response.

"So, you think that you deserve to be Cheer Captain over Kimberly? I have to wonder… what do you bring to the table that she can't offer the team?"

He says 'the team', but what Bonnie hears in that moment is 'me'. Its then and there that Bonnie knows what she HAS to do. Smirking, she hops up onto the first bleacher step… and does the splits, spreading her legs perfectly until her panty-clad cunt and ass are pressing into the bench. Coach Drakken is still sat right in front of her, but now Bonnie is eye level with his crotch as she glances up at him, grinning impishly.

"Allow me to show you, sir. After all, actions speak louder than words~"

The handsome older man doesn't say a word, which Bonnie takes as tacit approval of what she's planning on doing. She can't deny it… she's already a little wet, and her mouth is watering as she reaches for Coach Drakken's shorts and pulls them down in the front, yanking them out of the way so his cock can flop out from within it's confines. His member is half-hard and nearly hits her in the face, but rather than being disgusted at him for undeniably perving on them during practice, Bonnie is just more turned on.

She's also egotistical enough to think his arousal is all for her and no one else. After all, she IS the seductive one. Reaching out, Bonnie grabs hold of Coach Drakken's cock with both hands, and without further ado, leans forward and puts him in her mouth. Her eyes dart up to make sure he's enjoying what she's doing, even as she swirls her tongue around his cockhead, sucking as best she can.

… Despite being the seductive one, it's actually her first time giving head. But she's practiced with fruit before just in case she needed to really impress a guy at a party. So, she knows well enough how to suck cock, and she puts every ounce of faux experience she has from sucking bananas and cucumbers into sucking Coach Drakken's dick.

He doesn't groan in abject pleasure or toss his head back or anything that Bonnie is hoping for, but he does reach out and place a hand atop her head, smiling down at her.

"Interesting. Show me more, Ms. Rockwaller."

Eager to impress, eager to please, and most of all eager to earn that Cheer Captain position by ANY means necessary, Bonnie begins to bob up and down on the Coach's cock with all her might and speed. She might not have any true experience, but she makes up for it with enthusiasm and an eagerness to please. Sucking and slurping at the cock in front of her, Bonnie doesn't see a single damn thing wrong with what they're doing. Coach Drakken is just so handsome, after all, and she really, really wants to impress him.

As such, when he abruptly pushes her head back and cums all over her face, Bonnie doesn't complain. When he yanks her up out of the splits, turns her around, and brusquely orders her to lock her knees together and bend over, she doesn't complain then either.

She's already a little sweaty still from practice, truth be told. Maybe she should have gone and taken a shower before she tried to seduce her Cheer Coach… but if Coach Drakken is upset by her grunginess, he doesn't comment on it, even as he flips up the back of her skirt, pulls down her purple panties, and grabs hold of her jutting behind as Bonnie perches there on the bleacher bench, her hands on her knees and her knees locked together.

When he stands up and places his cockhead against her pussy lips, it strikes Bonnie that she's about to lose her virginity, right then and there, in the middle of the auditorium. Coach Drakken is going to fuck her, and for what? The Cheer Captain position? For a moment, Bonnie considers calling the whole thing off. She even has her mouth open, about to tell Coach Drakken it isn't worth it… and then he's inside of her.

A sharp squeal leaves Bonnie's lips as he takes her virginity. There's no hymen to break, due to Bonnie ripping it during horseback riding when she was younger, but it's still her first dick by far, and fuck if it hurts just a little to have something so big and thick and throbbing rampaging its way into her cunt. The young woman shudders as Coach Drakken fills her with his cock… and then he pulls out, only to do it again.

… The second time doesn't hurt at all, frankly, and is nothing like the first. When he thrusts in that second time, Bonnie's eyes widen and her mouth drops open, not in pain, but in pleasure. The third thrust is the same, and then the fourth, and the fifth… and she quickly loses track as she squeaks and squeals, as she mewls and moans.

Coach Drakken is fucking her, and it's too late to back out now… but honestly, now that he's inside of her, Bonnie isn't sure she wants to anymore. It feels so good, now that the initial pain is gone. He's fucking her and it's rather humiliating and embarrassing, and anyone could walk in on them any moment… but it's happening, and Bonnie honestly wouldn't have it any other way.

When the Coach reaches around and flips up her top to grab at her tits, groping and squeezing them, Bonnie lets out a wanton moan in response, shuddering in his grasp.

"You like that, don't you Ms. Rockwaller?"

Bonnie hastily nods, whimpering all the while, her pussy walls clenching down around his cock.

"That's what I thought. You're a naughty one, Ms. Rockwaller… very naughty indeed."

And then Coach Drakken begins speeding up, and Bonnie's eyes go wide again before rolling back in her head completely, the young woman cumming on her Coach's cock right then and there. It's the first time Bonnie has ever orgasms from a man's touch before, but it's certainly not the last. Coach Drakken puts her through her paces, that's for sure, and by the time he's done with her, by the time he pulls out and ruins her uniform and covers her body in his jizz, Bonnie has lost track of how many times she's cum.

He coats her in his cum, just like he did her face, but Bonnie, as humiliating and embarrassing as that is, can't find it in herself to be angry with him. It feels too good, like he's marked her as his property, for Bonnie to mind all that much. Besides, it's Coach Drakken… if anyone deserves to be allowed to do whatever he wants, it's him, right?

Still, Bonnie is nothing but single-minded when it comes to pursuing what she wants…

"D-Does this mean I'm… I'm Cheer Captain now?"

"No."

Coach Drakken's immediate, concise response shatters Bonnie's world as she stares at him with wide eyes, covered in his cum. He smiles back at her pityingly.

"Ms. Rockwaller… if you think this is enough for you to become Cheer Captain, you're not as intelligent as I had thought you to be. Was I wrong about your intelligence?"

Bonnie is quick to shake her head, eyes still wide.

"N-No sir!"

"Then I imagine you'll find a way to keep impressing me, until you can finally secure the job. Won't you?"

"Y-Yes sir!"

"Good girl… dismissed."

Bonnie leaves the auditorium, humiliated but hopeful. She just… she just has to find a way to convince Coach Drakken of her worthiness. He liked fucking her well enough… but she alone wouldn't cut it, Bonnie could see that now.

No matter. One way or another, she would convince him. No matter what she had to do, Bonnie would do it.

-x-X-x-

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