Chapter One

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Author's Note: Fair Warning! This story is very very smutty! Normally, this wouldn't be a problem, for me at least...but it's written about Seymour Skinner and Superintendent Chalmers from the Simpsons...That said, this IS a joke that I took very seriously. Feel free to replace the characters with your OTP.




Finally, Seymour was alone. Most of the teachers were either in their rooms or had gone home, there were no after-school sports today, and Willie hadn't started his rounds yet. The perfect opportunity for some alone time. Seymour exhaled out of his mouth, closed his blinds, and turned to sit down in his chair.


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Seymour panted, his trousers puddled on the floor under his desk and his tie tossed over his shoulder. He had put one leg on his swiveling chair and spread the other for easier access. He was palming himself through his briefs, recreating an image of a particularly satisfying porn video which depicted a little brunette twink getting pounded over a desk by an older bear. It was a boss/employee scenario- the twink asked for a raise and the boss decided to make him work for it. Seymour came twice to that video, once because of the sheer smut of it, and the second because later that night Seymour became aroused again by replacing the twink employee with himself and the boss with a certain older superintendent.


Sure, Seymour had a bit of a crush on Superintendent Chalmers. So what? It's not like Seymour expected anything to happen. He wasn't desperate. He just wanted the superintendent to push him up against a wall and fuck him silly, that's all. Oh, hey, that's a good image. Putting that one in the bank.

Outside of his head, Seymour had stripped off his briefs and was stroking his cock slowly, one hand up his shirt and circling the pebbled flesh of his nipple. He moaned out loud, figuring no one would hear him. He was alone, after all. His mind drifted over different memories of the superintendent. He imagined how the superintendent would look in a t-shirt, biceps filing the sleeves. Or, even better, no shirt at all. No pants, standing in his underwear. Seymour guessed he was a boxers kind of guy. Goodness. What about Superintendent Chalmers, with a hard-on, in his boxers? Seymour could almost feel the superintendent's cock filling up his mouth, fucking his throat, keeping him from breathing. Oh god. Seymour stuck his fingers in his mouth (which didn't help his already ragged breathing), testing his gag reflex, feeling the wet warmth. His hand sped up and he was bucking into his hand, moaning with his fingers still in his mouth.

"Fuck. Fuck fuck fuck- oh gosh oh god-" Seymour hadn't felt this worked-up in a while. His mother's house prevented him from ever getting anything but a quick jack in the shower, but here and now he could moan almost as loud as he wanted and not have to worry about anybody bothering him. "Mmmph- oh gOD yesyesyes-" Superintendent Chalmers (the one in his head) had bent Seymour over and was stretching him with his fingers, brushing his prostate ever so slightly. Accordingly, the real Seymour was using his slicked-up fingers to replicate was the superintendent was doing to him. Seymour moaned each time he got all the way in to his knuckles, which was every time. He didn't hear the click of his doorknob turning.

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⏰ Last updated: Apr 16, 2019 ⏰

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