You get the tables turned on you in a way you didn't expect

When you first met Valerie this Monday, it was lust at first sight. Even though you'd just had two sexy schoolgirls squeeze every drop of cum out of you in quick succession before you first met her, if she'd offered to be your personal cock-sleeve, you think you would've gladly thrown away considerations of your bet and spent the whole week making up for lost time and giving her criminally-neglected pussy some much-needed stretching.

It feels like an appropriate way to cap off your visit to have her warm lips embracing your dangling orbs, giving them a thorough washing with her slippery tongue.

"Oh, that's a nice start, Mrs. Glidden..." you purr. "I, mm, see that you're not quite ready to slip your fingers up the pink side-road behind, let alone the rear alley. But since this is your first time handling a nice hard dick in so long, it's best you focus on that. And my sack full of sassy treats, of course."

"Mmmffuhhh... guhhhh..." you hear awkward gulps and moans from between your thighs as Valerie takes both of your balls all the way into her mouth and starts applying some pleasant suction. Her tongue washes over every inch of the mottled, sensitive skin while her fingers tighten around your shaft. Her free hand pulls open one of the drawers in her desk and starts fumbling around in it.

"What do you think you're doing, you naughty overgrown daddy's girl? You're not going back on your beliefs and trying to find a spare condom, are you? Surely you realize there's no way I'll allow that." you say in a sassy tone, grabbing her shoulder as you keep one leg propped up on her desk. "You don't wanna end up in Hell alongside me, do you? That would defeat the whole purpose of punishment and torment and such. Breeding you over and over again for eternity is more like my idea of paradise."

"Mwah... mwah... mwah..." You hear cute little smacking sounds as Valerie's lips plant a series of affectionate kisses on the sacrilegious orbs that have caused such havoc in her school... like two spherical demonic portals, through which legions of sinful futa sperm have possessed the pure, unsullied wombs of students she was responsible for protecting.

"Ooooh yes." you moan. "You're better at this than any of the girls I've run into here. They're really all quite naive and innocent. I mean, not the virginal kind of innocent," you say with a sarcastic edge, "but they really are a lot more sheltered than most college students would be. None of them tried deep throat, none of them were up for a three-way... I didn't get so much as one offer to do anal, even by the ones who didn't have a condom and trusted me when I promised to pull out."

"Unnnhhhh~" Mrs. Glidden lets out a lusty groan as she pulls back slightly, unbuttoning the front of her suit jacket and exposing her impressive breasts, covered in a lacy black bra. "You vile, treacherous beast..." she murmurs as she yanks off your skirt and tosses it aside.

"Yeah," you say, "it's a sin to tell a lie, isn't it? But wouldn't it be a greater sin to engage in sodomy? C'mon, use that sharp tongue of yours and show me how grateful you are."

It's a heavenly sensation as the beautiful dean's mouth admits your hard cock. Unlike her students she's not incapable of taking it all the way. You feel the head of your beast pushing against the tightness at the back of her throat... but she keeps going. The soft gagging 'Gluk, gluk, gluk' sound she makes as she goes so deep that your cock bulges out her throat is as musical to your ears as a heavenly choir.

"Careful now. After watching Patrice stealthing that mischievous brace-faced blackmailer in the computer lab, I'm on a hair trigger. You wouldn't want my sacred sperm to perish in your stomach acid, would you? Don't they all have souls, or something?" you say with a wicked smirk.

"Captain Taffers..." Mrs. Glidden says, noticing that your shaft left a smudge on her glasses and pulling them off to toss them on the desk with disdain, "your reckoning is coming sooner than you might think..."

Before you can clap back with a comment of your own the door suddenly slides open behind you, making you stumble with surprise. "AH! Hey, this is a private meeting-!" you protest. Forgetting that you're bottomless now, when you whirl around, your hard, saliva-covered cock points straight at the newcomer.

And that newcomer is indeed a sight worthy of a good, stiff erection. It's Professor Hochmann from earlier - the only woman you've seen here who could rival that buff lacrosse player Yolanda in the boob department. The blonde history teacher's immense cleavage is heaving up and down with each breath she takes as if begging you to slide your cock in there for a good tit-fuck... but she is breathing heavily not out of lust, but rage. Incandescent fury is radiating from the bespectacled blonde MILF's eyes.

"CAPTAIN!" she snarls at you through gritted teeth. "I knew it. I KNEW it! You've preyed upon the assistant dean's well-known weaknesses to corrupt my beloved institution and my students!"

You frown, betrayed. "Valerie!" you whine. "Tattling on me to your own subordinates as an excuse to wriggle out of your rightful duties? I expected better from you! I mean, nobody expects someone like ME to be honest, but I thought you were different!"

"I didn't tell her to come here! Ilsa," she says to the blonde professor, "can't you see I'm... occupied in a delicate form of discipline? Get out of here! I'll explain everything later!"

But the stacked professor stays where she is. You turn back around to face her. "Professor Hochmann," you say, "I won't lie and tell you that I haven't fucked a few of your students. But Mrs. Glidden here didn't have anything to do with that. Ludmilla and the other students from your lecture came to me on their own. And don't go blaming the X-rated content in my little historical documentary for their behavior either. I've been around the galaxy and, trust me, all those girls knew what they were doing. Even if a few of them had never seen real futa fucking before, they've got to learn some time, right? Think of it as a bonus biology lesson..."

"This isn't about that, depraved though it may be!" Professor Ilsa Hochmann says. "Abusing my trust to show uncensored, unsimulated hard-core pornography in my lecture hall is one thing."

"But," she says, closing in on you menacingly, "I just went through the notes in the end credits of your," she makes some very sarcastic air quotes with her fingers, "'documentary re-enactment'... and I see that the source you cited for this supposed 'history' was fucking 'Milkipedia.org'!"

Before you can react, she lunches forward and grabs you by the neck, tightening her hands and **** off your air supply! For a woman in her late 40s with a desk job, Professor Hochmann is surprisingly strong. "DID YOU HONESTLY THINK I WOULD LET YOU GET AWAY WITH PRESENTING INFORMATION FROM A GOD DAMN CROWD-SOURCED ENCYCLOPEDIA IN MY INSTITUTION OF LEARNING, YOU EMPTY-HEADED WHORE?! 'VISITING PROFESSOR', MY ASS! YOU DON'T EVEN HAVE AN ASSOCIATES DEGREE! YOU ILLITERATE FUCKING PARASITE!"

She's not loosening her grip. Rather, she's tightening it. And with how much of your body's blood supply had been diverted to keep your cock rock-hard, you have that much less to spare. It's starting to seem like you might be going to Hell sooner rather than later as the enraged professor shakes you back and forth like a rag doll.

"Please stop, Ilsa." Valerie says calmly. "I know that you tend towards the cruder methods of corporal punishment. But this is no mere naive first-year student who doesn't know any better. This is a grown woman - asterisk behind the word woman, of course - in her thirties who has no excuse for such shameless behavior, whether that be manipulating good-hearted young women into sinful trysts or corrupting the academy's intellectual integrity. I was just about to administer a far more suitable punishment. And since you're here, you can assist in case she gets uncooperative."

You try to be low key about taking a much-needed deep breath after Professor Hochmann takes her hands off your neck. "Ack. Ahem. Is that a kink of yours, Mrs. Hochmann? Mm, you know, the one time a guy I was with started **** me in bed, I freaked out and called station security on him. But maybe I was too hasty. If you wanna try it in private, we've got a whole weekend, and I could stay in port a few days longer~"

"Focus on me, Captain Taffers." Valerie says in her stern, confident voice, finishing taking her suit jacket off and sliding off her enticing pencil skirt, leaving her standing there in just her lacy black lingerie and stockings. "As I recall you were quite insistent that neither you nor I leave this room until we had, and I quote, 'freaky hard-core sex'?"

"Awooooo." you give an excited little yelp and turn back towards Valerie, stroking your spit-slicked shaft with one hand. "How could I forget? And don't worry about compromising that 'ethic' you are so proud of, either. I can promise you there'll be no pulling out."

"There certainly won't be." Valerie sways her enticing rump seductively as she goes over to a bookcase. Curiously, she moves a lot of the books aside and opens a hidden panel.

"Uh... what are you doing?" you ask curiously. "We don't need any lube, Val. I'll take care of that." you stick your tongue lasciviously between your index and middle finger to emphasize your intentions.

"Oh, I can smell that you won't need any lube from here, you degenerate futa." Valerie says, a hint of excitement entering her calm voice again. "Even over the unholy musk of your sinful, unnatural cock, I can tell you're dripping."

You are confused. Wait, what? It had crossed your mind earlier that Mrs. Glidden might potentially be a futa herself, but, when she took her skirt off, you were able to see that she didn't have any surprises tucked away down in those sexy panties of hers. "Uh..."

Before you can wonder too much, Mrs. Glidden turns back around. And the sight makes you gulp nervously.

In Valerie's hands is the BIGGEST strap-on dildo you've ever seen in your life. Rather than being a realistic, natural creation of synthskin and smart-rubber, it is a pitiless, gleaming, chrome-finished monster covered in rows of bumps. It puts you in mind of a the codpiece a knight from ancient times might have on his suit of armor.

"Let me introduce you to 'The Grand Crusader'." Valerie says proudly as she firmly affixes the intimidating sex toy to her hips. "Every inch of it crafted by hand and blessed by the High Cardinal of Great Charity herself, just two steps below the Holy Mother in the hierarchy. In all five years that I have been in charge of safeguarding the morals of St. Vivians' Academy, I have never had just cause to wield such a great and terrible weapon. To do so is, of course, a sin in and of itself, which will take me many months to find forgiveness for."

Your mouth is hanging open, and you laugh nervously. "Th-that's why you're so hellbent on catching the hidden futa in your student body! You wanted an excuse to use THAT thing on her, since you don't consider her a 'real' female, so it wouldn't be a mortal sin or whatever. You dirty, naughty bitch!"

Valerie starts stroking 'The Grand Crusader' with her hand, and it whirs to live, starting to vibrate intensely. It's a much deeper pitch than any other vibrating sex toy you've ever heard - it sounds more like a plasma engine manifold, a deep, rich thrumming rather than a high-pitched buzzing sound. The enraged Professor Hochmann is left speechless, staring in mute horror.

"It's too late for you to escape your penance entirely, Captain. You do know what they say about 'sparing the rod', hmm? But I seek to emulate God in mercy as well as firmness. I will spare you the latter portion of your penance and settle for just giving you a thorough reaming, if you confess your crimes and dishonesty, and give me the name and face of the impostor before she can ruin my beloved academy's reputation forever."

"W-wait a second! Did you forget that I have a recording of that muscle-bound lacrosse player beating the shit out of a poor, innocent man just because he gave her a baby-making creampie? Or, or that one of the girls on your track team was whoring herself out to the janitor? Or that the futa who's supposed to be in charge of security let a student get away with illicitly recording porn videos in exchange for pussy? You can't try and deny it either if I make it public! Odds are, at least one of those thee young ladies is going to be swinging around a baby bump in a few months. And... imagine how much trouble you'd be in if I brag about how many schoolgirls I knocked up this week with my unnatural futa cock? I don't know the final tally yet but 'more than one for every day of the week' is something the scandal-chasing gossip websites could sink their teeth into, don't you think?" in spite of yourself you realize your voice has been getting shrill and ****.

"I'm not concerned. You'll have quite a few very good reasons to stay quiet about all that by the time we're finished here." Valerie says, licking her sensuous lips. "Now bend over, you bad girl."

"You heard the assistant dean." Professor Hochmann's voice has a note of cruel vindication as she seizes your wrists and drags you forward over the desk, leaving your shapely, pale legs kicking helplessly over the edge, and painfully pinning your stiff cock against the hard wood of the desk.

"Hold on, let's talk about thi-AHHHHH!" Valerie doesn't give you long at all to wallow in dread or anticipation, as you feel a warm, hard, vibrating pressure between your ass cheeks. It slides over your puckered asshole and down to the excited slit beneath. Your pussy hasn't gotten nearly as much action as the other half of your equipment this week, just a single, quick, mediocre standing-doggy fuck on the first day to keep a teacher distracted long enough for you to dump a fertile load in the nerdy blonde he'd been giving private tutoring. But it seems like Mrs. Glidden is going to make up for that lost time and then some.

"AHHHH!" a shrill cry escapes your lips as the bumpy, vibrating shaft pries your flower open. It has none of the flexibility or compressibility of a real cock. You've never been penetrated like this before. Hard, mechanical, and unrelenting. Your eyes widen as it glides deeper into you, each row of bumps stimulating your labial lips.

"S-stop! It's not going to fit!" you protest. But that just brings a harsh spank on your exposed ass cheek from Mrs. Glidden's hand. "Ilsa? I can tell Ms. Amanda is going to be troublesome. Do me a favor and keep her mouth occupied, would you?" Valerie asks politely.

"My pleasure." the buxom blonde MILF says in a throaty voice as she steps out of her own pencil skirt. Not even bothering to remove her white panties, she shoves her whole crotch in your face and fills your nostrils with the scent of her musk as she starts roughly grinding it against your face. Your attempts to protest only result in your lips getting a mouthful of her fragrant undergarments... and soon, between your saliva and her excitement, that fabric is getting damp enough that you can feel her cuntlips against your face as she grinds against you relentlessly.

And speaking of relentless, Mrs. Glidden turns out to have been correct. You didn't think it possible, but you feel the soft skin of her thighs pressing tightly against your own, as her hips squeeze and compress your gorgeous ass. You feel like if she was to move just a little bit deeper, that thrumming, vibrating dildo would be touching the back of your teeth. The vibrations are so powerful that you're sure you can feel them reverberating all the way to your fingertips. An excruciating mix of pleasure and pain leaves you at such a loss for words that even if not for Professor Hochmann holding you in place, you'd be able to say nothing.

Just as Valerie is starting to back out, she thrusts all the way to the hilt again, stretching your pussy around the warm, hard tool. "YES!" she shouts. "I want you to think of all the students you defiled, Captain! Confess to each and every one of them by name! God is listening!"

"Aunnhhh! Unh! I, I..." your voice quavers as Valerie starts to piston her hips back and forth, "I didn't get all of their names..." you mumble around the pussy filling your field of vision.

"SINNER! PERVERT!" A series of sharp slaps fills the office as Valerie starts hammering away at your quivering cunt with forceful thrusts. "Beg for mercy!"

"Mmfffcccyy, mffffccyyyyyy!" you try to moan, which only succeeds in pulling the underwear to the side and giving you a full taste of the buxom blonde history professor's snatch.

"Not until you've earned it, slut!" Valerie shrieks in ecstasy as she grips your ass painfully hard with both hands, spreading you as wide as possible. She goes so deep you can feel her own sex. This isn't the first time that you've felt a warm pair of labial lips trickling hot juice over the surface of your balls. You've been feeling that several times a day every day for the past week. But this is the first time you've felt it while YOU were the one getting filled up. And.. damn. It IS turning you on. You'd always dreamed about getting to fill up Claire's pussy after you win this bet, to make that proud rival of yours submit to you. But now you wonder... if it might not be more fun the other way around? Having this unnatural artificial abomination pounding your box sore is only making you crave the real thing even more.

After what seems like hours and after you make Ilsa cum with your tongue, you can hear Valerie panting heavily, and feel her sweat mingling with her own where her hips are grinding against your ass. She's finally slowing down.

"Have I... have I learned my lesson...?" you ask.

"Oh, goodness no." Valerie says in a mocking tone of voice. "Your journey to... *huff*... repentance has scarcely even begun. If you cannot demonstrate true contrition in the next few days, that repentance will take you many years. Decades, actually. This will not even be the first step. The first *huff* step alone will take you many months. About nine of them, give or take a few weeks."

"...huh?" you ask, blinking your bleary eyes.

"I think the Grand Crusader is just about ready to deliver its heavy load of judgment unto you, Amanda." Valerie leans down to whisper in your ear. "Surely you don't think it is just a toy for empty, carnal pleasure, do you? Did you really think I would keep such a thing, if it didn't have a higher purpose?"

"Oh shit...!" you gasp, quite out of breath yourself. "No, no, no, no!"

"Ohhh yes." Valerie says delightedly. "Don't you think it was a terrible shame that my husband was cruelly taken before he could give me more than a single child? I had always thought so. He was the kindest, most pious, most wonderful man who ever lived. So of course, I had to keep a part of him with me. Or to be more precise, several million parts of him, left over from the first time we decided to start a family."

"WHAT THE FUCK?!" you gasp out in a ragged voice, looking over your shoulder at Mrs. Glidden's gorgeous half-naked body pressed against your backside. "You mean..." your voice cracks, "there's a dead guy's jizz in that thing?? What the hell is wrong with you? Get that thing out of me you psycho bitch! Out, pull it out!"

But just as you are crying out, you hear a 'heavenly choir' that you realize isn't your imagination. Specifically, the devotional '~Ahhhhhhhh~' music is coming from behind you... and it's heavily muffled, as you can hear it inside your body.

"Halleluiah!" Valerie cries out triumphantly.