The Head Master

A balding man in his mid 40s jumps out of his desk chair in shock as you kick in his door and drag a half naked student into his office by the asshole. Your disappointment is palpable, but you quickly decide the Headmaster must go around deciding who gets head, rather than administering it. You have a bone to pick with him anyway.

"JESUS CHRIST! Who the fuck are you?!" the man yells, looking around his office for something he can use as a weapon.

"Are you the HEAD MASTER around here?!" You yell, warming up to give him a piece of your mind.

"Y-yes...." The Headmaster stammers, still trying to decide if you're a threat.

"I have been on your campus for more than an hour, I've passed dozens of your students, and not a SINGLE one of them has offered to blow me yet. Not even one! You call this a Hole Academy?! In the BLOW JOB FUCKING UNIVERSE?! What kind of HEAD MASTER are you?!"

The man blinks at you several times then slowly looks down at the letterhead on his stationary. It indeed says Hole Academy exactly where he could swear it used to say Holy Academy. His brain slowly processes that everything you said is true, but can't seem to understand it.

"Sir, I have been working at this Girls Academy for more than 20 years, and I'm pretty sure no one has ever offered to blow me." He finally states back, taking in Maddison's huge tits in the new school uniform for the first time. "Not ever."

"Well, whose fault is that? Aren't you the Head Master? You should be teaching these holes proper manners!" You turn your attention to Maddie, wiggling your middle finger around inside her punitively. "Maddison, isn't there something you should be asking the Headmaster?"

"Oh! Ow! Uh... can I like... You know..." Maddie mumbles, taking the soiled panties out of her mouth. You **** another finger into her asshole to coax her harder. "Ow! Uh, please let me suck your dick, Headmaster!"

"Wow! That was really easy! Is she going to blow me now?" The Headmaster exclaims, already reaching for his zipper.

"Not yet! Not yet! She said the right words, but she has to feel it. A hole must beg to be filled." You begin trying to stretch the teenager's virgin asshole enough to accommodate a third finger. "Try again, hole."

"PLEASE let me suck your dick, Headmaster! AHH! Please! I'll do a really OW! A REALLY GOOD JOB! AHH! Please just let me suck your dick! OW! Please! Please! Please! OW!" Maddie begs at the Headmasters feet, already desperately trying to pull his pants off. The moment she gets his zipper down a massive cock flies out like a spring snake out of a fake can of nuts, hitting her in the face with an audible slap. The Headmaster at least has a schlong worthy of his name, causing you to mentally add an inch or two to your own length, just to be sure you are at least a bit larger.

"Okay, so NOW is she going to blow me?" The Headmaster asks, gesturing to Maddison lapping and sucking at the head of his penis trying to figure out what she's supposed to be doing with it. This is technically her first kiss and she only vaguely knows what a blowjob is, so she mostly tries to make out with his penis in whatever way will convince you to take the fingers out of her asshole.

"Hmm, well she clearly wants to suck your cock, but she hasn't earned the right yet. She hasn't apologized for being a worthless hole and not offering you a blowjob sooner. I would suggest giving her a good cockslap until she learns her place."

The Headmaster gives Maddison a light pat on the cheek with the head of his penis then waits for an apology.

*tmp* "I'm sorry..." She says.

"Sorry for what?"

"For being a... uh... worthless hole...."

You shake your head in disappointment. "Does it sound like she knows she's a worthless hole? Much less feeling sorry about being one..."

*Pap* "I'm sorry for being a worthless hole."

*PAP* "I'm sorry for being a worthless hole."

*Smack* "Uhn! OW! I'm sorry! I'm..."

*SMACK* *SMACK* "GAH! I'M A WORTHLESS HOLE! I'M A WORTHLESS HOLE! Nnnguk...guk...guk...guk..." Maddison screams, taking the Headmaster's cock into her mouth, just to stop him with hitting her with it. She begins bobbing up and down on at least half his length, but stopping at the entrance of her throat.

"Wow! She's almost as good as my wife already!" The Headmaster says, proudly watching his student's rapid improvement. He places his hand on the back of her head and begins getting into it.

You shake your head again. "This type of complacency is how the school got like this in the first place! Don't forget that you're doing her a favor by letting her give you a blowjob. You can't just give her what she wants so easily."

The Headmaster tries to pull his cock out of the teenager's mouth, but she sucks harder and chases him around, so he pulls her back by a rough handful of blonde hair and forces her to let go. She whines.

*Spack* "Mmmnn... I'm sorry for being a worthless hole! GAK...uk...uk..GUun! AH!" *SPACK* "AH! I'm sorry for being a worth...GUK... Worthless h...GUK... Worthless ho...GUK GUK GUK... WORTHLESS HOLE!"

The Headmaster continues to whip Maddison with his huge cock, using his grip on her hair to steady her head as well as to take a few greedy pumps into her mouth while she tries to speak.

*SPACK* "I'm sorry I... GAK... I'm sorry I'm... GAK... I'msorryI'mwor... GAK GUK GUK... " *SPACK* "GAH! I'M SORRY I'M WORTHLE... GUK GUUKkkk" *SPACK* *SPACK* "I'M SORRY I'M WORTHLESS! GUK GUK... I'M SORRY I'M WORTHLESS! GUK I'M SORRY I'M WORTHLESS GUK I'M SORRY I'M WORTHLESS GUK I'M SORRY I'M WORTHLESSSSSsssss... GUUkkkkkkk..."

"Fuuucckkk yyeeaaahhhh..." The Headmaster groans as he reaches new depths in Maddison's tight throat, now taking most of his length on each bob. "She's better than my wife already! Can she blow me now?"

She clearly knows she's worthless and seems very sorry about it, so you nod in approval. "That is good enough I suppose... But the thing about being a teacher is that you need to encourage your students to overcome their perceived limits and do the impossible! Things they never thought they could do on their own!" You line up the head of your cock with Maddison's asshole in a threatening manner, seeing your own larger size for the first time since you spitefully wished yourself to be slightly larger than the Headmaster. It's like holding a bat! You consider shrinking it down later, but luckily you've been stretching out Maddie's rear the entire time she's been apologizing, so it's perfect for what you have planned.

"Maddison, if you don't get the last few inches down your throat in 5 seconds, I'm gonna shove this whole thing up your asshole in one thrust." You pat her asscheeks so she can feel it's massive size. "Ready? GO! 5!"

"GHKKK! GUkkk Gukk guk... GHKKK! Urkkkkkkkk!" Maddison makes unintelligible noises as she immediately begins to panic, trying to **** another inch down, but she is already at her limit.

"4!"

"GHKK! Guk guk guk Guk GUK GUK GUK GHKKKK!" Maddie begins going faster and more forceful with each bob, practically trying to headbutt him to get it down.

"3!"

"GUULLLKKKKKKKkkkkkk...... kaff kaff kaff.... GULLLLKKKKKKK!" She pushes with all her might, trying to put her whole weight on it for as long as she can.

"2!"

"HRMM! NNMM MUUUnnnnnnmmmn! NNOOUU! GKKKKKKKKK!" Maddison tries to plead for more time, since she has managed another two inches through brute ****, but the last inch just won't fit.

"1!"

"HHHHKKKKKKKkkkkkkkiiiiiiiikkkkkkkkkkkkkkkkk........" Maddison lets out a guttural scream around the cock in her throat and gets the last inch down, finally allowing the Headmaster to hilt himself.

Unfortunately, she started screaming thanks to you suddenly cramming the head of your huge cock into her asshole and pushing with all your might, attempting to go balls deep in one go. Her asshole is still too tight, so it's more of a slow sink inside her as she trembles and convulses in pain beneath you. Once you are both hilted in the barely conscious teenager, you resume your conversation while enjoying the spasming of her abused holes wrapped around you.

"I can't believe she took the whole thing in on her first try! I didn't think it was possible!" The Headmaster exclaims as he rolls Maddie's head around his crotch and enjoys the fullness of her throat engulfing his entire length.

"All these holes need is a little encouragement to excel. This one is a fast learner."

"That makes sense, Maddison Koontz here is an honor student. She was accepted to every college she applied to and was slated to be valedictorian this year." He begins casually jerking himself off by dragging her head by the hair while beaming down at her with pride.

"You were gonna send this worthless hole to college without ever giving a blowjob? In Blowjob Universe? How would she ever get into a sorority? Or get a boyfriend? It's completely irresponsible. You call yourself the Head Master? You're barely a Head Amateur."

The Headmaster begins yanking the young blonde up and down his shaft more aggressively, as though to make up for lost time training. "Well what do you think I should do?"

You begin thoughtfully thrusting into Maddie's asshole as you wonder to yourself what would make someone the master of getting head in the blowjob universe. "Well I'd expect you'd at least have gotten sucked off by every girl at this school, just for starters."

Headmaster fucks Maddison's skull harder and harder as he thinks of all the girls enrolled at Hole Academy this year blowing him one by one then stops dead, smashing her nose and holding her down in shock. "Even my daughters?"

You stop your thrusting and look back in even greater shock. "Your daughters aren't blowing you already?! If they aren't learning it at home or at school, how will they learn to be a good fuckholes for their husbands? What have you been teaching them all this time, math?"

Headmaster looks away in shame. He had been teaching them math. He was teaching all of these girls math this whole time. He tries to figure out where he got such a stupid idea. "I thought guys wanted virgins..."

"You mean they're virgins too?!"

"I think almost all the girls at Hole Academy are..."

You pull out of Maddison's asshole and unceremoniously push your filth covered cock into her unused pussy, tearing her hymen just to check if it's there. You slide in easier than you expected, but you feel the undeniable pop of her cherry. You feign disappointment. "This place is in worse shape than I thought."

You mostly did it for fun, planning to switch back to her ass right away, but something about being called worthless has made Maddie soaked. You swear you can feel her working her Kegel muscles around you already. Like her whore instincts kicked in the moment you slid inside and began giving you a massage from shaft to tip. You pound into her fresh hole with renewed vigor.

Headmaster's eyes well up with tears as he begins to feel like a failure, both as a father and as the chief administrator at an all girls school. "You should be the Headmaster of this school, not me...."

You consider running the school from the back office as you continue to thrust into Maddie's freshly deflowered cunt with your disgusting dick. You were hoping for a more hands on approach to the education of your students, not just shuffling paperwork behind the scenes. You try to think of a way to restore Headmaster's confidence in himself, so you can focus on the important things, when suddenly a miracle happens. "Head Master, LOOK!"

"Guk... Guk... Guk..." Maddie was sucking him off. And not just a little, the mad cunt suddenly begins going to town on him like a hole possessed. As though she was studying the Headmaster's weak points the entire time he was using her head like a fleshlight and learning to mimic the movements perfectly. She then begins to bounce on top of you as well, pushing back against you in perfect timing with your pounding thrusts.

Maddison Koontz, honor student and constant overachiever, now understands that being worthless is the same as getting a failing grade at Hole Academy. She needs to be a good fuckhole to succeed at this school. No! She needs to be the BEST fuckhole in school. Anything less than top of the class is unacceptable! She pours her heart and soul into pleasuring your cocks as though she is taking the most difficult test of her life.

You and the Headmaster cannot endure this treatment for very long, especially since you were rather close to orgasm to begin with. Maddie instinctively takes the Headmaster to the hilt as she senses him approaching his limit, using her throat muscles to coax his load directly into her stomach, while simultaneously using the tight inner walls of her pussy to fill her womb with your seed. Even she cannot help but to orgasm herself as she milks the both of you for what feels like several minutes, not stopping until you have filled her worthless holes to the brim like a world class whore. Maddison feels like she has finally found her true purpose in life.

You all collapse in exhaustion.

"You did it, Headmaster! You taught her to be a good fuckhole!" You say triumphantly. Even Maddison seems pleased with herself. She doesn't even flinch when you clean her virginal and anal fluids off of your crotch with her panties and push them back into her mouth for cleaning.

"WE did it!" Headmaster says, "And I couldn't have done it without you! You have to stay and help me reform this school into a proper Hole Academy! I'll implement any rule you want!"