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Dudley Dursley and the Diabolical Do-Over (Harry Potter)

In which Dudley Dursley is given a chance to go back and have his way with the wizarding world. Of course he's going to take it.

CambrianBeckett · Derivados de obras
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42 Chs

Chapter 41

Most people would say that being summoned to the Headmaster's Office just after the Opening Feast was a bad sign. After all, what could you possibly have done wrong to get sent there so quickly? Perhaps getting caught having sex on the Hogwarts Express?

… Needless to say, Dudley Dursley was not most people. As he sits in the Headmaster's Office across from Hogwarts' brand new Headmistress, he can't help the smile that keeps pushing its way onto his face, causing the corners of his mouth to quirk up in amusement. At the same time, he also can't help but raise an eyebrow as his smile is matched by the woman sitting on the other side of the desk.

"Headmistress… Umbridge. You should have told me the good news."

Tiffany Umbridge giggles in response, shrugging in a way that makes her chest bounce as she leans back in her chair. Except, unlike other witches, the beautiful blonde KNOWs she's doing it and is in fact doing it on purpose and to great effect too.

"Ah, but then I wouldn't have gotten to see the look on your face earlier when you saw me sitting up at the Head Table~"

Her teasing is honestly fairly well-earned. The look on Dudley's face HAD more than likely been a sight to behold when he'd first laid eyes on Tiffany up there where Ariana had once been sat. Of all the people he could have pictured taking Ariana Dumbledore's place, Tiffany Umbridge hadn't made the list. But then, that was her entire vibe, wasn't it? She was never quite what he was expecting.

For a moment, Dudley considers letting her know that she's only sitting there because of him. No one else is aware of the specifics behind Ariana's retirement. Only he knows of the part he played in making the woman step down at long last. In a way, Tiffany truly owes him for his part in opening the way for her. But… theirs isn't that kind of relationship.

There are a lot of women in this second chance of his that are beholden to him in some way, shape, or form. Women he practically owns, each in their own way. Tiffany Umbridge is not one of them. The blonde is different, Dudley is man enough to admit. She's different and he likes that about her. Sure, he COULD find a way to make her just as much his property as all of the others, but that would be boring and quite… repetitive in the end.

Still, his curiosity had to be sated.

"How did you pull it off? No offense, but you can't be the most qualified candidate for the role. Not by a long shot."

Tiffany grins at that, a saccharine grin that makes even Dudley squirm a little bit in his seat.

"Qualified? Since when has the issue of qualifications been a real component of choosing the next Hogwarts Headmaster, Dudley? After all, just look at my predecessor. The woman might not have looked a day over forty, but she was undeniably senile. And yet, they let her continue as Headmistress for decades past her expiration date."

That was… fair. But also, Tiffany was deflecting. Dudley just raises an eyebrow at her and waits patiently, which she acknowledges with a simple nod before giggling some more.

"House Umbridge has served certain elements loyally for hundreds of years, Dudley. My Aunt Dolores… well, she might be content staying in her lane and working on trying to get her petty grievances through at the Ministry, but I'm much more ambitious than her. I'm the most ambitious Umbridge in a long time. And seeing as my family knows where all of the bodies are buried, on account of that centuries of loyal service…"

She trails off then, not spelling it out… but then, she doesn't have to. Dudley immediately picks up on what she's putting down.

"Ah."

"Yes, quite."

They exchange a knowing look, even as Dudley makes a note to himself to watch Tiffany's back. He might not know the details, but it sure sounded like she'd gone ahead and blackmailed a bunch of very pompous officials in order to get this position. And if she'd blackmailed the wrong sort of people with the information she apparently had access to, they might try to end her.

That said, Tiffany was her own witch. Technically she was older than him, though when you counted both of Dudley's lives together, he had age on her. However, his first life had been spent in the mundane world, so in terms of magical experience, Tiffany still had him beat, one might argue. But in terms of life experience? Dudley felt like he held the advantage there. His first life had been quite cutthroat after all, even if it was magicless.

Still, he wasn't going to say anything. He didn't have to let Tiffany know she might have ruffled some feathers and pissed off the wrong wizard. She was a smart cookie, and he'd just silently make sure he had her back, no matter what.

Meanwhile, Tiffany looks around the office for a moment before looking at him with a twinkle in her eyes.

"Shall we break this place in, Mister Dursley?"

Dudley raises an eyebrow and looks around as well. Normally, he'd raise a concern about the numerous portraits that fill the Headmaster's Office. However, at the moment… every last one of them is in a magical sleep, effectively put in stasis. The whole lot of them, including even Headmistress Ariana Dumbledore's newly painted portrait, are in their frames, their heads slumped over, and their eyes shut.

They won't see or hear anything, and so Dudley has no problem with rising from his chair and giving Tiffany a grin.

"Well Headmistress… who am I to decline such a generous offer?"

The blonde witch lets out another giggle as she strides around the length of the desk to meet him. By the time she's arrived, Dudley already has his arms open and is more than happy to gather her up in a hug, pulling her in close as she places her hands on his cheeks and kisses him soundly. Meanwhile, HIS hands go down to her shapely ass. The new Hogwarts Headmistress is a modern witch for the modern era. She's dressed in a pink pencil skirt and a pink suit jacket, with a white blouse on underneath.

Dudley likes the ensemble. He likes it a lot, especially for how her pencil skirt hugs her ass and her heels lift said ass right into his hands. Groping and squeezing her buttocks for a while, he only finally lets go when she starts to work open his robes and pull them off of him. Only then does Dudley reach up and begin doing the same with her suit jacket, getting it off of her so he can start unbuttoning her blouse.

It's surprising, because in his old life Dudley thinks he would have hated Tiffany Umbridge. He'd hated all women save for his mother by the end of that first timeline. Mostly because none of them gave him the time of day. But… deep down inside, Dudley could acknowledge the truth. The fact that he wasn't worth their time. He wasn't worth much of anything at all in his past life.

That didn't mean he hadn't enjoyed stealing Harry's magic of course. Nor did it mean he hadn't enjoyed ruining Hermione Granger, or making sure Lily never regained her entire mind. He'd gone ahead and stolen Harry's life, there was no denying it. But then he'd gone several steps further. He'd improved upon Harry's life. He'd made it HIS life. Truly, Dudley Dursley had come into his own not just as a wizard, but also as a man.

The man he was today was fascinated by a woman like Tiffany Umbridge. They were birds of a feather, the two of them. And he couldn't get enough of it. The blouse comes off around the same time his shirt does, and as Dudley is working open Tiffany's bra, she's running her hands down his chest and towards his belt buckle with clear intent.

There's not a trace of the fatso that Dudley had once been. Ever since coming back in time, he's made a concentrated effort to avoid ever being that fat tub of lard again. This wasn't just his chance to get back at his cousin after all. It was a second chance at life, and Dudley… Dudley had worked hard to make the most of it.

As such, the torso that Tiffany runs her arms down, while not so cut as to be a six-pack or anything like that, certainly isn't as flabby as most wizards probably would be. Dudley's hands, as they pull her bra apart and lift it off of her pale breasts, are filled with a physical strength that most wizards lacked as well. As Tiffany pulls his cock out from the confines of his pants and Dudley tosses the bra away before leaning in to sup at her breasts, suckling on her nipples, he feels quite confident in his body.

Which is good, because the new Hogwarts Headmistress is certainly confident in hers. Tiffany moans, thrusting her chest into his hands and mouth even as she strokes his cock to full mast, making sure he's properly erect as she tilts her head back and lets her eyes drift shut. For a handful of moments, that's all the two of them do. But eventually, the build-up is just too much, and Dudley needs to… he needs to be inside of her, right then and there.

With a growl, his hands drop down to Tiffany's waist, finding the hidden zipper of her pink pencil skirt in record time. He yanks the garment off of her, and then yanks her up off the ground. Setting her down on the edge of her own dress, he continues to feast upon the Headmistress' tits, paying extra special attention to her teats. Meanwhile, she spreads her legs apart and slips her panties to the side with one hand as she gives his cock a tug and directs him to her slit with the other.

She's wet enough that Dudley doesn't even hesitate to slide right into her. Punching into Tiffany Umbridge's cunt, he grunts into her mouth even as he holds her by her hips. His fingers dig into her pale flesh, and the beautiful blonde moans as she wraps her legs around his waist, locking her ankles together behind his back.

His cock throbs inside of her, pulsating with need, and Dudley grunts into one of her nipples as he starts to thrust almost immediately, barely even bothering to settle in for. Tiffany, for her part, meets him thrust for thrust. Her hips rise as he pistons in and out of her, and her hands go to his shoulders, clinging to them.

Eventually, Dudley's mouth comes away from Tiffany's breasts. He looks up into her eyes instead, his forehead ending up pressed against her forehead. If not for his plans… he would marry this woman. He could see himself enjoying life with her. They were birds of a feather, and he knew beyond a shadow of a doubt that she would not just gladly, but gleefully take part in the sort of ethically black antics that Dudley got up to on a regular basis.

Alas, he'd already decided he was marrying Fleur Delacour. He was going to make that veela bitch his wife and he was going to have fun doing it too. But then, maybe that was perfectly fine. After all, marriage was, especially in the Wizarding World, something of a lopsided affair. Out in the muggle world, women were getting more and more rights by the year. But in the Wizarding World, things were still as they were in ancient times. Most of the time, the woman was sold to the man by her father… it was just dressed up a lot more nicely these days.

In that regard, claiming Fleur as his wife just made sense. Dudley would dominate their relationship. Fleur would be his woman in all the ways that counted, and when it came to how their marriage operated, he knew that 'wife' would be synonymous with 'sex pet'. Turning Tiffany into a sex pet would just be a waste of the blonde's potential.

Fleur might be his wife… but Dudley saw Tiffany as a partner. A partner in bed. A partner in business. A partner in crime. She could be it all for him, and instead of a lopsided marriage, they could have a relationship of equals. He liked that. He liked that a lot.

As he fucks Tiffany soundly atop her desk, Dudley looks into her blue eyes and grins. As she grins back at him, he likes to think he sees in her gaze an understanding. Like she knew at least a little of what he was thinking, and agreed with every last word. Of course, he wasn't going to bring it up now and ask her while they were fucking. That would be quite gauche to be sure.

Instead, he continues fucking the blonde, grunting as she moans, groaning as she mewls. Her pussy walls flex around his cock and she cums for him a couple of times as he fucks her there. Until finally, he can hold back no longer and with a grunt, he creampies her right there on her desk. He fills her up with his seed, trusting her to be able to handle the mess. After all, they'd already had THAT conversation.

The both of them enjoy a few moments of bliss as they come down from their respective orgasms, and then he pulls out of her and falls back into his chair with a grunt. What surprises him is when Tiffany follows, the Hogwarts Headmistress dropping to her knees right between his legs and taking him in her mouth.

Her big blue eyes stare up at him as she uses both hands AND her mouth to clean him off, sucking him and slurping him dry until all the mess that's left on his cock is spit from her tongue instead of their combined sexual fluids. Then, she keeps going. She continues blowing him until Dudley is rock hard again, not that difficult of a task when he's a young man with an incredibly healthy libido.

Once he's fully erect once more, Tiffany pulls off of his cock with a pop and gives him a salacious grin as she licks her lips and rises to her feet before promptly climbing into his lap and impaling herself upon him without a second's hesitation. As she slides down his length, she thrusts her chest into his face and Dudley slides his hands along her ass as it becomes abundantly clear that they are just getting started.

This was certainly going to be an interesting year for both him and Hogwarts. That was for sure.

-x-X-x-

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