No Good Deed Unrewarded

by TheWingman

Rating: mature
Tags: Profanity, Alternate Universe, Human, Principal Cinch, Original Character, Comedy, Other, Equestria Girls, Porn, Sex
Length: 3842

What was supposed to be a walk on the beach, Jet Set has a rather unexpected encounter with someone from school. But, he never knew how it'll go down.

Jet Set, he was one of Crystal Prep Academy's model students. Though slightly nervous, he manages to get by with good grades. While on a walk along the beach, he bumps into his principal, Abacus Cinch. Though running into her didn't surprise him, what follows after would rock his world.

Contains: Sex between student and principal, a hungry MILF

Takes place two months before Chapter Two of Dr. MILFlove.

Cover art by the legendary Zelc-Face.

Published 2018-11-27 20:40:01 UTC
Last updated 2018-11-27 20:40:01 UTC

A Reward Well Earned

Author's Note

Well, you were wondering what I've been up to in regards to my Dr. MILFlove series. Well, apart from this and another spin-off I've paused work on, I've been writing an outline for an expansion of the series storyline. I do appreciate your patience and don't fret. Spoiled Rich/Milk's chapter is coming within two weeks, estimated. Anyways, I hope you all have fun reading this.

A Reward Well Earned

“Ahhh, never get tired of the scent of salt water.” Said Jet Set. Taking walks on the beach was one of the things he truly enjoys. It was a destressor for him after each week at Crystal Prep. But because he is due to graduate within two months, it won’t bother him as much. As much as he wanted to take a dip in the ocean, he wasn’t dressed for it. For now, he just wanted a walk.

As he roamed along the sandy path with the sun beaming down on him, thirst soon set in as sweat dripped from his brow. From his previous walks, there was a stand that sold ice cold drinks. Shifting his stride, he headed towards the stand… only for a peculiar sight to distract him. Walking toward a small rock wall nearby, his eyes focused on a sight that made his jaw go slack.

“What the fuck?”

There, emerging from the waters and clad in a bikini, was CPA’s very own Principal Abacus Cinch. Ever noticeable from her hair of varying shades of magenta and her stern expression, it was a rarity to see her at the beach enjoying herself, let alone in a rather good looking two piece swimsuit. But most of all, she had a nice looking body, perfect tits and ass ratio. The very sight of which made Jet’s cock grow hard in his shorts.

“Why in the hell is my principal so hot?!” He thought to himself as he looked on at her beautiful yet powerful form. As strict as he came to know her as, Jet Set had to admit she has it going on. Jet continued to ogle his principal from a distance until her gaze turned to his direction. With a split second, he ducked behind the rocks, hoping she didn’t notice him. Looking down his shorts, he saw that he was nearly erect.

As he focused on getting it under control, he felt a set of fingers grip his ear, wincing from the pain as he was dragged to the other side. Opening his eyes, he found himself face to face with the last person he wanted to see.

“Mr. Jet Set,” Snarled Cinch, with noticeable anger. “What do you think you were doing spying on me?” His heart filled with dread. There he was, face to face with the woman he certainly didn’t want to piss off. Yet, his hard on returned with a vengeance. It was a mix of fear and arousal; He didn’t know which to focus on. Just as he was about to speak, her fingers closed his lips tight. “Nah ah ah, Mr. Jet Set. As far as I’m concerned, you’re in a lot of trouble. Next week, I’ll have a talk with you and your parents to decide your punishment.”

Soon, fear overtook Jet Set as he closed his eyes and prepared for the worst. He was so close to graduation and now all his efforts were destined for the drain. But then, a snicker was heard which soon evolved into laughter. For a moment, Jet’s fear was replaced by confusion. Never before had he seen Principal Cinch laugh.

“Oh my goodness,” Cinch laughed. “You should’ve seen the look on your face!”

“What?!” Stammered Jet as he tried to process what was happening. “Seriously, What is going on? One second, you were going to punish and now you’re laughing?”

“Oh come now, just because I’m a strict principal doesn’t mean I’m without humor.”

“Well, at least I should be relieved you weren’t gonna bust me over something so minor as a stare.” With a mental breath of fresh air, Jet calmed his nerves. Though she was still in a skimpy bikini, it wasn’t what worried him the most. For now, his mood was stable. “May I ask what you’re doing here?”

“Well, I own some beach front property that I inherited from my grandfather.” Answered Cinch as she stretched her legs. “Every once in a good while, I like to come down here and have some time to myself. I would assume you came down here for a walk. Is that correct?”

“Yes,” Nodded Jet Set. “but I was on my way to a drink stand. The sun is making me parched.” Cinch looked at the senior student before her. Throughout Jet’s career at Crystal Prep, his efforts caught the notice of Cinch. Knowing he was due to graduate, she thought to reward him for his efforts. The conditions she desired have been met and the time to enact her plans had arrived. Even though what she envisioned was wrong, she simply didn’t care.

“You know what, why don’t you save your money and come with me?” Beckoned Cinch as she started toward her beach home. “I have plenty of drinks at my place.”

“What?” Jet Set blurted with bewilderment. “Wh-Why?”

“Well, I want to give you an option that doesn’t cost you a penny. Now, follow me please.” Thirsty and sweaty, Jet Set shrugged his shoulders and followed his half-naked principal to her house. It was like an old style home, with a few touches of tudor aesthetics, quite avant garde yet conservative at the same time. Even the interior had the same mix of decor. A couple of old vases, devices and paintings were amongst a modern setup of a flat screen, electric stove, and a smart fridge.

“Please, take a seat.” Said Cinch. “I’ll be with you shortly.” Jet, however, didn’t sit down. His eyes were too fixed on a peculiar photo above the fireplace. Upon closer inspection, it was a younger Cinch… and another girl that was even younger. She looked very familiar. And soon enough, the pieces came into place.

“So, you’re Sunny Flare’s mom?” Asked Jet with amusement.

“Correct.” Cinch replied, entering the room with a tray of drinks. “I wouldn’t doubt that the physical similarities gave you the hint.”

“It did make me suspect as much but she never mentioned it at all. Why?” Cinch sat on the couch, crossing her legs and beckoning Jet over.

“Well, if your daughter goes to the same school you work at, you would do well to avoid preferential treatment. It’s not to say that I allow students to give her a hard time. She even made it into the Shadowbolts on her own. I couldn’t be any more proud of her.”

“Well, you’ve certainly raised her right.” Jet then took a big gulp of his drink, sighing in relief and cooled off. “Oh god , this really hit the spot. Thanks.”

“Why, you’re welcome.” Cinch scooted closer to Jet, making him increasingly nervous. “So, how does it feel to graduate soon?”

“W-Well, I-It feels great. Going to g-go to c-college for a theater program.”

“Hmmm, interesting. Writing plays or or acting?”

“A little of both?” It was incredibly odd. His principal was acting friendlier than usual, even bordering a bit on lust. It began to creep him out. Briefly breaking out of his spell, Jet Set asked his question. “Okay, why did you really bring me here?” Amused, Cinch drew a sly smile and laid back.

“Well, since you’ve asked, alright then. As you know, I’m a strict principal that values hard work. That’s not to say that I don’t believe such work should go without reward.” Then, Cinch placed a hand on Jet’s thigh and began stroking it. The feeling sent a wave of confused pleasure through his nerves. He wanted to enjoy it but another part him said it was wrong. “You’ve performed admirably in your career. I feel as though I should reward you for all your hard work. You’re about to graduate and I know just what to give you.”

“What if we get… We could get into trouble!” Slightly annoyed at her student’s continued resistance, Cinch cups his face in her hands. He began to slightly hyperventilate, knowing what was about to happen. Slowly, Cinch’s face grew closer and closer to his.

“Don’t worry about that.” She moaned. “I’ve made sure that no one but us will know. But, I could tell that you’re wanting this as much as I do.” Her eyes drifted down to his shorts to see his erection, still throbbing with excitement unbound. “Now, let’s do away with the delays and get to it, shall we?”

Jet set had no time to react when the soft rose lips of Cinch made contact with his, even more so when she forced her tongue into his mouth without warning. The sudden jolt of pleasure made him surrender to his lust as he wrapped his arms around his horny principal. She was good and she made it feel great.

“Holy shit!” Jet gasped as the kiss was broken. “That was incredible!” His remarks, however, earned an unamused smile from Cinch.

“Ordinarily, I would advise you to watch that tongue of yours.” She sighed,brushing away a lock of hair. “Since this is an informal meeting, I’ll let it slide just this once.” Jet nodded in agreement as Cinch got off the couch. Her gaze shifted downwards towards towards Jet’s Crotch to a sight she finds amusing. “Hmmm, looks like someone’s in there, wanting to be set free. Take them off, if you will.”

Knowing of his erection, the discomfort of his shaft being constricted by his clothing had set in. Having already made out with his principal, Jet decided to forego any resistance and oblige her request. After kicking off his shoes, his shorts and underwear soon followed, allowing his throbbing member to spring free. Needless to say, Cinch was quite surprised at his size.

“My goodness,” She gasped. “you certainly are gifted.” The sight of his cock gave Cinch a tingling sensation in her nethers, followed by a developing wetness. She imagined how good something of that size would feel inside her. But, she wanted to make him feel good first. “Now, Mr. Jet, allow me to show you a woman in her natural form.”

Reaching behind her back and with a click, her top fell softly down, exposing her ample E-Cup breasts for Jet’s pleasure. Then, off came her panties. Not a sign of pubic hair could be seen on her nether region. There, she stood completely naked, leaving Jet Set stunned and wide eyed with hunger. His cock throbbed as Cinch sat between his open legs, staring it down.

“Here,” Said Cinch, grabbing her arousal soaked panties and putting them to Jet’s nose. “Keep inhaling this. I’m about to, as they say ‘Rock your world’.”

Diving head first, Cinch began sucking on Jet’s cock. Her soft velvety lips made it feel all the more better. It was something Jet had never experienced before and he enjoyed every bit of it. Taking a whiff of his principal’s panties, his nose was beset by a musky scent, a byproduct of her arousal. The very scent heightened his arousal in return, amplifying the feeling of the blowjob. His back arched and he let out a hearty moan. It was as if he was seeing heaven for the first time.

“Oh god,” Jet moaned as his balls tightened, growing closer and closer to orgasm. “I’m going to explode!” Cinch didn’t stop sucking. On the contrary, she quickened her pace at which she did it. It further flooded Jet’s mind with lustful bliss. Then, his cock throbbed and quivered as it erupted with its load. As his mind became lost in the bliss, he felt a sucking motion on his rod. It didn’t take him much to realize that she swallowed his entire load.

“Wow, so pent up, aren’t you?” Said Cinch as she hopped onto the couch. Jet only nodded in agreement to her amusement. “My my, you’ve never had much time for fun.”

“Been focusing hard on my studies, ma’am.” He replied. “Especially since this year.” Cinch admired a dedicated student when she sees one. Even then, she recognizes when anyone needs a brake. Her students were no exception. Her eyes glance down towards his member, flaccid and spent. Cinch knew he would like to fuck her at some point and needed to revitalize his stamina. With a silent nod, she knew exactly what to do.

“Well, a good student like you deserves a good reward.” Cinch moaned laying against the armrest spread eagle. “Go ahead, do with my body as you will.” Jet couldn’t believe it. His principal, THE principal of his school that just gave him a blowjob, had just allowed him to use her body. Only in pictures did Jet Set see women so lewd. Now, it was his chance to experience the pleasures of the flesh.

Without even a nod, Jet climbed on top of his principal, resting his body on hers before locking his lips with hers. Any worry has been replaced by an abundance of confidence. His member touching Cinch’s vulva cranked his sex drive to levels alien to him. Holding her body close, he ground his cock against her crotch. With every pass, every second of contact, his desire only grew higher as his cock hardened once more. But for him, he’s the one to repay any favor.

Slowly, Jet set ran his tongue down her neck, between her breasts, a few laps around her navel before arriving at her groin. But, he didn’t immediately go diving for her vulva. Seeing as she nearly scared him to death earlier, it was payback time. He brushed his tongue past her vulva, scraping it within her inner thighs. Judging by how twitchy it made her, Jet surmised he found her tickle spot. With her moans and sighs as fuel, he lapped his tongue on her thighs, taking care to leave her pussy untouched, even his smallest of breaths. He wanted Cinch to want it, he wanted her to beg.

“Oh god, please! Please stop teasing me! Eat me like dessert!” That was all the signal Jet needed. Encompassing her nether lips in his mouth, he let his tongue unleash its assault. Moan after moan, yelp after yelp, he kept on going with the occasional nibble on her clit. The pleasure drew Cinch wild, causing her hold Jet’s head close. She squirmed and writhed with sexual bliss, arching her back as she screamed, unable to formulate a coherent word. Even as he slipped his tongue inside, it only drove her further towards her orgasm.

With a few great screams, Cinch couldn’t take it anymore as her own orgasm exploded. The rush of her ladycum blasted into Jet Set’s mouth. He did his best to lap up as much of it as he could. Though, a little bit of it got on his chin. Once Cinch’s grip loosened, Jet broke away to get a breath of fresh air.

“My word,” Breathed Cinch, reeling from her orgasm. “I’ve never felt that good in years! Why?!”

“Well, you nearly scared me to death earlier.” Jet Set replied. “Plus, it was fun to hear you beg.”

“Oh, you’re terrible, student.” Seeing his shaft hard once more, Cinch knew the time for the main event was now. “Now, it’s time for the final part. I want you to put that cock of yours inside my pussy. No need to worry about me getting pregnant. I’m on birth control.”

There it was, the moment that would come sooner or later for Jet. His heart pounded as he climbed back on her. Using one hand, he positioned his cock until he felt it brush against her labia. Slowly but surely, he eased his shaft into her moist cave. The fleshy walls began to constrict snuggly around it. He gasped as if he were out of breath. The warm wetness blew his mind halfway across world.

“So, how does it feel now that you’re a man?” Those words rang through Jet’s mind. His virginity was gone, claimed by his principal. He stared into her eyes, heart pounding from his emotions going in all places. All that mattered to him as he gave Cinch a passionate kiss was pounding away at her flower. Thrusting in and out, Jet’s adrenaline and testosterone increased exponentially; each thrust eliciting a moan. Breaking the kiss, he moved his hands to her breasts, even latching his mouth on one. The nibbling and suckling feeling on her sensitive nipples made Cinch lose her mind even more. Combined with the earlier teasing, she was closer than she thought.

“OH GOD! I SORELY NEEDED THIS!” Cinch screamed. I’M SO CLOSE! DON’T STOP! WHATEVER YOU DO, DON’T STOP!”

She was right. Her inner walls constricted further and further around Jet’s cock. The tighter it got, the more force and speed he had to exert. It was exhausting yet pleasurable for him to the point where grunts started leaving his lips. They were both in bliss, soon to be fueled by the throes of orgasm.

With a loud wail, Cinch’s orgasm was the first to be unleashed. Her inner walls clenched upon the still pumping shaft inside, making it all the more sensitive. A gush of ladycum soaked the couch and his crotch, providing only a little bit of lubricant. However, Jet wasn’t ready to cum just yet. He kept thrusting as if his life depended on it, eventually becoming lost in the bliss of coitus.

Eventually, his cock couldn’t take anymore and let loose ropes upon ropes of his cum. Even then, he wouldn’t stop. He started thrusting without the support of his arms, using only his legs to keep balance. Pumping and pumping, he kept going until every last drop of his load was gone from his balls. Cinch could only look on in exhaustion at the senior student pounding her cunt like mad. Then, his body began to feel light and his vision went to black as he fell back on the couch with the world fading around him.

Jet’s eyes began to slowly open as he found himself on some bed in a room. His head felt foggy and his legs were a tad bit like jello. Strangely enough, he was completely clothed, shoes and all. As he wondered what happened, the door opened and through it came Cinch, holding a glass of water.

“Ah, you’re awake.” Mused Cinch. “You’ve worn yourself out quite a bit.”

“Wha… What happened?” Jet moaned as he sat up. Cinch handed him the water which he guzzled down.

“Well, you were out for an hour. After I gained my bearings, I got you cleaned up and dressed.” Cinch saw him give a face that spelled ‘WTF’. “And before you start freaking out, no. I would never stoop to that level of depravity.”

“Well, though it’s weird, I thank you for that.” He got up and stretched his legs. Though a bit wobbly, he was able to walk. “So, how did I do?”

“You did great.” Cinch replied, “Though you were a bit rough around the edges, I suppose it’s to be expected since it was your first time.” As the last two words echoed through his mind, he began to panic about one thing: his crush, Upper Crust. He was going to visit her later and ask her to go to prom with him. With his virginity gone, his first time with her will never be. Cinch noticed his distress and grew concerned. “Is there something wrong?”

“Well,” Jet sighed. “I plan on taking my crush, Upper Crust, out to prom next week. If she wants me to go over to her place afterwards, I-I already gave my virginity to you! Oh shit!”

“Let me tell you something, Mr. Jet Set.” Cinch replied, putting a hand on his shoulder. “Whether or not you have your virginity at this point is moot. In my experience, what a woman truly values in that regard is a man who is sexually experienced. You have some experience from our earlier engagement. No need to fret about it. In the event she does want to… you know, you’ll be ready.”

Hearing those words from his principal stirred something in Jet Set. He couldn’t tell what it was but Cinch knew very well what it was: confidence with a twist of ego. He accomplished what he hoped to to before graduation, even if it wasn’t with whom his heart desired. If anything, he could at least give Upper Crust an experience she’ll never forget, virginity intact or not.

“You’re right, Ms. Cinch.” Said Jet as he began making for the living room. “It probably will be a non issue.” Turning around, Jet gave Cinch a hug. “Thank you.” Just then, Jet felt Cinch reach into his pockets and place something. Reaching in, he saw that it was three condoms.

“What?” A puzzled Jet asked. “What for?”

“I have some advice: Wrap it before you tap it.” She said with a sigh. “I was young and foolish during my college years. After one dance, me and my boyfriend at the time went to his place. One thing led to another and that’s how my dear Sunny Flare came to be. Though I was able to get by, it wasn’t without… difficulties.”

“What difficulties?”

“That is a story for another time, student.” Cinch gave Jet a pat on the back before walking him out the door. “Go on, go ask Upper Crust.”

With a confidence fueled nod, Jet walked off, leaving the beach behind. In the span of nearly two hours, he managed to lose his virginity, courtesy of Principal Cinch. As far as things were concerned, things were looking good for him that day. In the midst of his stride, his phone started buzzing. Unlocking it, it was his friend Calculus Crunch.

“Hello?” He answered

“Yo Jet, Where are you?” Calculus answered. “Me and Ignacio are at Smoothie Island. You coming?”

“Yeah, I’m on my way. Is Upper Crust still working there?”

“Yeah, it’s still her shift. If you hurry, you might be able to ask her. Don’t worry, we’ll back ya up.”

“Oh, that won’t be needed.”

“What? Are you sure? You sound unusually chill.”

“Well, let’s just say that my walk on the beach cleared my mind a bit.”

“Riiight. Well, we’ll see ya when you get here.”

“Alrighty, see you then.” Jet hung up the call and continued on his course. Though there was a slight bit of nervousness in his heart, it was negligible. All that mattered to him was finally being able to ask his crush to the dance of the school year. He was more excited than ever and all was right in the world for him.

“Oh fortune, my name is Jet Set!”