Everything was normal at Canterlot High School. Classes for the day had just ended, students were walking out of their classrooms, their shoulders slumped with fatigue, saddened at the fact that it was only Thursday, and they had to wake up early once again tomorrow. Freshmen were hurrying off to their after school practices, while the JV and Varsity players were piling in their cars to grab an early dinner before their practices started.

Teachers were tidying up their classrooms and grading tests, while the office faculty were thumbing through all the school’s paperwork. One man sat in a chair opposite of the secretary’s desk, waiting to hear those words he’d heard so many times before. His ears reflexively twitched in annoyance as he heard a familiar, authoritative voice emanate from the behind an ajar door marked ‘Vice Principal.’

“Send him in, Cadence.” The voice called to the beautiful and youthful secretary across from the man, but before she could even open her mouth to speak, he rudely snapped at her as he headed into Luna’s office.

“I heard her, sweet-cheeks. I don’t need you to guide me to her like a toddler.” Cadence simply smiled bittersweetly at him before resuming her work at her desk. Upon seeing who had walked into her office, Luna sighed heavily and rolled her eyes. As if she didn’t know it was him just by his gruff voice and ungentlemanly demeanor alone.

“Superintendent Sombra.” She spat out. “I’m sorry, but Celestia is home sick today. If you want to discuss something with her, you’ll have to-”

“I didn’t come to talk to your sister, woman.” He sneered. “It’s you I was looking for.”

Luna scoffed before taking off her glasses and tucking them into the collar of the blouse under her dark blue blazer. “Very well, what do you want?”

He smirked evilly before explaining himself, circling Luna in her desk slowly as he did, his piercing stare going through her and his arms folded behind his back as he did so. “Well, as you know, Canterlot High School has been getting all the funding it could ever need for the past three years since I was elected superintendent.” He chuckled darkly before continuing, “However, I currently see no reason to continue the funding-”

“No!” Luna stood from her chair, slamming her hands on her desk as she did so. “You can’t do that! We’ve been nothing but supportive of your service as our superintendent, there’s no reason for you to stop our funding!” That was a complete lie; she hated the superintendent. Sombra’s demeanor thoroughly creeped her out every time he visited the office, and his entitled attitude disgusted her just as much as his perverted stares did.

Sombra responded with a scowl, annoyed at being interrupted. He cleared his throat and continued, giving Luna a cold stare as he circled her desk in a more intimidating posture. “I would agree with you, but remember that your sister and I have quite the history.”

Luna’s eyes filled with anger as she recalled the memory. Celestia and Sombra had dated before either of them held position in the school district, and he had beat Celestia after she refused to put out for him. She almost began shaking with anger; she resented Sombra. On top of being a total pig to her sister, he now tries to womanize every female in the high school’s office whenever he visits before meeting with Celestia, only to ask her to sleep with him again. Though he always threatens her with her job, Celestia always finds a workaround, knowing more than enough information about Sombra to uproot him from his position. Luna, however, was not so lucky as to know as much about her superintendent. After exploring her thoughts for a few moments, her eyes widened as she realised why Sombra chose to meet with her instead of waiting for Celestia to be available. “Sombra… You can’t be serious!”

A deep chuckle emanated from deep inside his throat. “Oh, but I am. You see, Luna, Principal Celestia has not been as… supportive of my campaign as you claim to be, and she has refused to change her views on my position as superintendent. I’m afraid that If you don’t want me to send a request for her removal, and if you want CHS to continue to receive the funding it needs to be the clean, prestigious school it has always been, I’ll need a little… Incentive.”

Luna dug deep into her thoughts, trying to plot some way to get out of doing what Sombra was implying. Suddenly a lightbulb came on in her head before she gave him a confident grin. “How’s this for incentive: Continue to fund us, and I won’t dig out the old newspaper article explaining why you were kicked out of office from your old school district. It’s a little pathetic to embezzle money from a continuation school’s treasury, don’t you think?”

Sombra didn’t try in the slightest to contain his laughter. “Oh, how naive. Luna, if you even try to show that document to any of my superiors, you’ll look like a complete fool. I’ve had all documentation of that event wiped from public record; you have the only remaining copy of that document…” Slowly he walked towards a filing cabinet in the corner of her office. “Oh, what’s this?” He pulled the document in question from a folder and slowly tore it in half, laughing lowly as he did so.

Luna mentally cursed as her fists tightened. She thought harder, deeper, begging her conscience to find something, anything, to dig her out of the pit Sombra had thrown her into. “You won’t get away with something like this. I’ll contact the authorities!” She threatened, now beginning to panic a little.

“And who will believe you when you say that I bribed you? I’ve got a document back in my office with your signature on it that makes the whole topic of this conversation a completely legal matter. As far as the authorities are concerned, you signed a document, and then I left. Face it, Luna: you’ve lost. You can’t win, and you’ll never win as long as I’m in office. And judging by how much praise the district’s been getting since I took office, I’ll be here for a long time.”

Luna sighed as she admitted defeat. “What do you want, Sombra?”

Sombra slowly made his way to her door before locking it. “I think you know, Luna. Be a good little sister and carry Celestia’s burdens. Still, It’s hard to believe she wouldn’t put out. Such a shame, too; with a body like that-”

“Say another word about Tia and you won’t leave this office alive.” Luna threatened, her eyes now slitted in protective anger.

Sombra held his hands up in mock surrender. “Fine. No more about your sister. Now, where were we?” He asked before he began to disrobe, removing his dress jacket and tie before untucking his shirt.

I can’t believe I’m doing this. Luna thought to herself as she also began to strip down. Soon, both of their clothes were in a heap on the ground, and Sombra was stroking his sizable manhood, which was now lewdly sticking out from his abdomen, a proud seven inches in length. Luna knelt down in front of the superintendent, a look of pure disgust and anger on her face. “Don’t think for a second that this will ever happen again. Understand?”

Sombra put his right hand over his heart, while he stuck his other arm in the air at a right angle, copying the exact same pose he had made while being sworn into his position as superintendent. “You have my word.” He then gave her a grotesquely perverted smile. Luna stared back at him, her anger piercing into the evil of his dark irises. She then slowly wrapped her hands around his engorged member and began stroking it at a tantalizingly slow pace. His cock lurched at the attention, not that he hadn’t had a woman recently, but simply at the fact that no secretary he’d bedded with his false charm and good looks had a body like Luna. The big wigs had decided to assign exclusively flat-chested and narrow-hipped secretaries to the district office. Yes, he’d bedded a woman every night for the past month, but none compared to the plump posteriors and large racks which Celestia and Luna possessed. His cock lurched again as a stream of precum leaked from its swelled head.

Luna’s nose wrinkled in disgust as she jerked Sombra’s cock faster, desperately trying to expedite the process as much as possible. Sensing her intentions, Sombra reached down and firmly grasped her wrists before speaking. “Go slowly. We wouldn’t want this wonderful exchange to end prematurely, now would we?”

“You’re disgusting.” Luna shot back at the superintendent as she took half of his cock into her mouth, hoping that a blowjob would get him off faster. Sure enough, her talented mouth had Sombra groaning in a matter of minutes. He placed a heavy palm against the back of her skull and pushed her nose into his groin. She deepthroated his cock to the hilt with ease, and began flexing her neck, eliciting a gasp from Sombra as her throat muscles massaged his cock. Sombra’s disgustingly strong sense of pride took over as he realized that Luna had reduced him to a shadow of his regular self.

Refusing to be controlled by a mere Vice Principal, he roughly gripped a fistful of her hair, and began pulling and pushing her on his cock before he began to fuck her throat, not bothering to let her come up for air, he watched evilly as mascara-stained tears began to pour down her cheeks. Her face turned a flush red after about a minute of the brutal facefucking, her oxygen supply quickly becoming urgently low. Luna began waving her arms in panic, slapping Sombra’s thighs in an attempt to signal that she couldn’t breathe. Sombra laughed as her face began to turn blue, and continued to shove his cock down her windpipe repeatedly, not discouraged in the slightest.

Luna’s motions began to slow as her vision slowly blurred. After another thirty seconds, her arms fell to her sides and her eyes rolled into her skull. Sombra simply grunted in arousal as he now began to shove his cock down an unconscious Luna’s throat. Sombra gave a sick grin before he spoke to himself. “Took me long enough. Just how I like them.” He then began to lewdly fuck Luna’s face. Her throat still making gagging sounds, saliva now running from the sides of her mouth. Sombra’s thrusting only increased in intensity until he felt cum boil up from his balls. He pulled his cock from her face and began jerking off in urgency, his dick pointed straight at her face.

After about thirty seconds Luna’s eyes slowly opened as she regained consciousness, gasping for air only to have her eye splattered with a hot rope of Sombra’s cum. As she remembered what was happening she opened her mouth and sealed her lips around Sombra’s twitching cock, swallowing the rest of his seed so that none of it got on the floor. She stared hatefully into Sombra’s eyes the whole time, and he merely shot back a cocky smile as her fired load after load of semen down her throat. When he finished, Luna quickly withdrew her mouth from his dick and began to gather her clothes off the floor when Sombra simply laughed and put an arm around her waist to stop her, his cock still noticeably erect. “You think we’re done already? I’ve got another round in me, Luna. Get me off one more time, and then we’re done.”

Luna lowered her head as the shame of what she was about to do hit her. Dropping her clothes to the floor, she walked slowly to her desk and bent over it, propping herself up on her elbows as she presenting her sex to Sombra. Seeing the confident look in his eye, she spoke before he had a chance to approach her. “Not so fast, Sombra. I’m not gonna risk bearing a child from you. If you’re gonna fuck me, you’re only getting my ass.” Though it seemed an absurd thing to be formal about, she said this in her authoritative voice which she usually used when addressing students.

Sombra simply nodded, his characteristic smirk ever-present on his face. “Fair enough.” He said before lining up his manhood with her asshole. Not caring to be gentle after Luna giving him so much attitude, he gave a hard thrust, sinking the entirety of his length into her anal cavity in a mere second. Luna cried out in pain and held herself low to the desk, white-knuckling the edge of it with her hands as Sombra fucked her ass relentlessly. He grabbed one of her plump ass cheeks in each hand as he drilled into her, each thrust drawing a cry of pain and unwanted pleasure from Luna. As much as she hated to admit it, Sombra was a damn good lay, and she couldn’t deny the warm ball of pleasure that was quickly growing inside of her.

As he continued to drill her ass into oblivion, her head swam with pleasure as she lost perception of time. After what felt like an eternity, her sex began to wink and contract with each thrust into her ass, an orgasm now quickly beginning to build inside of her.

Sombra’s breaths became labored as Luna’s tight asshole was pushing his cock to it’s limit, slightly more sensitive than usual, having already came only minutes ago. He pounded into her faster now, and Luna could sense the urgency in his motions the both grunted as their orgasms peaked simultaneously, Sobra filling Luna’s ass with cum, while Luna’s pussy splashed her orgasm against his muscled thighs. Both of them collapsed after their euphoria subsided, panting heavily as they found the strength in their wobbly legs to get up and dress themselves.

As Luna was buttoning up her blouse, Sombra approached her with that usual perverted look on his face, tightening his necktie as he spoke. “Well, I suppose I should thank you for putting your sister’s affairs in order for her. As promised, such a transaction will not occur again; however, my regular visits will not cease.”

“Very well. And I expect that you will not bother my sister with such a request as you have posed with me?” She arched an eyebrow as she asked, trying and succeeding to look as businesslike as possible.

“Of course.” Sombra nodded as he turned on his heel and headed for the door. “Have a nice weekend, Luna. I shall be back for my usual weekly meeting with your faculty next Wednesday.”

Luna said nothing as she sat back down at her desk, fixing the papers that had been pulled out of order while she was getting pounded into the desk. Her cheeks flushed red as she thought about the undeniable pleasure she felt when Sombra climaxed inside of her. She shook her head free of the thought as she quickly put everything in order and stood to leave the office. As she was walking out from behind her desk, she glanced at the clock only for her eyes to open wide in shock as she realized that Sombra had been fucking her ass for the better half of two hours. She then began rushing to her car as she realized she was supposed to be home over an hour ago. Her cheeks turned redder than ever as she felt Sombra’s seed swish around inside of her belly and ass with each step towards her car.

When Luna arrived home, she made her way up to Celestia’s room and greeted her with a smile. “Hey, Tia. Feeling better?”

Celestia smiled tiredly as she sipped from a cup of tea. “Hi, LuLu. I’m feeling great actually! I think I’m good to return to CHS tomorrow. Oh, speaking of, how’d it go today?”

Luna thought to herself for a moment before she gave an exhausted sigh. The more she thought about her fling with Sombra, the less she minded it. Though it was a one time thing, the stresses managing the whole school for a day were relieved after her escapade with the superintendent. She gave her sister a warm smile before she spoke. “It was great. We had visit from the superintendent, but I took care of him. I managed to talk him out of that deal he keeps trying to push on you. I don’t think he’ll be bothering us anymore.”

Tia had a look of pure surprise on her face. “Really? I bet he was pretty anal about that. huh?”

“You have no idea.”

Author's Notes:

Pardon the horribly bad pun at the end. I hope you guys enjoyed this one, hopefully the next addition to this story won't take as long as this one did. As always, be sure to give this story a thumbs up if you enjoyed it.

Deuces, guys!