The only part of her job that Cheerilee truly despised was conducting parent-teacher conferences. Nothing irked her more than spending an entire day pouring her heart into teaching the fillies and colts of Ponyville, only to have to stay after class and be berated by self-righteous mothers who always held the belief that their daughters were ‘nothing short of perfection.’ They even had the gall to blame her for their foal’s poor grades, as if she had the authority to force any of her students to retain their lessons until test time. Back when Cheerilee had just started as the new Ponyville teacher, she had almost resigned in her first year after a particularly long afternoon filled with acid-tongued parents. Even after all of this, she still came in the next morning and taught her lesson, smiling wide at her pupils as if nothing could get her down.
She was similarly smiling on this spring day as she finished closing the curtains to the schoolhouse windows. The illumination from the building’s lanterns cast yellow light everywhere, making it feel much later than it actually was. Cheerilee walked between the neat rows of desks in the center of the room, picking up a pencil or discarded sheet of paper and placing it back into its respective desk. She always desired to have the school looking as presentable as possible for conferences, and every bit of the room definitely appeared pristine. Cheerilee nodded her head as she scanned her domain, finally deciding that it was worthy of an A+.
Conferences were usually set up by a note from one of her student’s parents asking when she would be available to meet with them. This would invariably lead to her having to cancel dinner plans or some date she had set up with her friends, and further along lead to her once again questioning her career choice, though very rarely in a serious manner.
Today’s conference was different though. Cheerilee had specifically sent an urgent note home with a student asking for a meeting, which she could only remember doing once or twice before. She was really looking forward to having the conference as well. It was the only discussion she would have to conduct for the day, but she was hoping that it might take up a good portion of her afternoon.
Cheerilee had finally stopped nitpicking about the classroom, electing to be seated on the stool behind her desk. She had a number of papers laid out before her, but facing the opposite direction, so that they could easily be viewed from the opposite side. She pulled out one of the drawers, and looked inside at the essays she had assigned for homework the night previous. She knew that she really should be devoting her time to grading them, but some things in life were more important than promptly returning papers. Cheerilee closed the drawer with a sigh, before resting her head on her desk.
She had been nurturing the idea of this scenario in her mind for a few months, and there couldn’t have been a more perfect day for her than this one. Dealing with the needs of foals as they grew and matured was rewarding, but it reminded Cheerilee of her own needs, which had been severely neglected as of late. It didn’t help that it was the time of year where she (along with every other mare in town) was searching for a colt to be with as if Celestia would banish her to the moon if she didn’t. And she had no desire to take care of that herself like she had to last year.
Cheerilee was confident in her plans, and yet she still felt a bit of nervous anticipation growing in her stomach as the specified meeting time drew nearer. Things of this nature always had a way of going wrong, which could prove problematic seeing as she was abusing her position for personal gain. She chewed her lip anxiously as another minute ticked by, then another. Any second now she would have to put on her game face. She took a few deep breaths before donning her ever-present smile and running a hoof through her mane, trying to make sure that it had mostly stayed in place over the course of the day. She had begun to move her tongue over her teeth to assure that she didn’t have any cucumber from lunch still tagging along in her mouth, when a quick series of knocks sounded on the schoolhouse door. Cheerilee exhaled and cleared her throat.
“Come in,” she called, her bright tone still present in her voice. The door to the room swung outward, allowing the brilliant mid-afternoon light to splash in to the relatively dim room. A stallion took a few tentative steps into the schoolhouse, before turning to face the teacher.
“Good afternoon, Miss Cheerilee,” Big Macintosh drawled, taking a moment to close the door behind him. He turned and walked towards the desk at the front of the room.
“And a good afternoon to you as well, Big Mac,” Cheerilee answered. “Why don’t you take a seat so we can begin the conference?” She was a little surprised to see Big Macintosh look around for a few seconds, but not sit down. She tried to figure out the problem, before her cheeks grew a little redder. “Oh, I forgot to put a seat out for you,” she said with a nervous laugh. “Here, just wait one moment,” she said, getting to her hooves. She grabbed the closest stool and moved it in front of her own desk.
“Thank you kindly,” Big Macintosh said as he smiled at Cheerilee. He sat down as she returned to her stool, likewise being seated. There was only a second of silence before she began to speak again.
“Well, Big Mac, I’ve called this conference with you because you’re the only adult on the farm besides Granny Smith while Applejack’s away on her annual trip to Appleoosa,” she stated simply, recalling the lines she had practiced mentally. “Now, I’d like to talk to you about Apple Bloom’s grades. While they’re not terrible, by any means, there’s certainly room for improvement,” Cheerilee said in her singsong voice.
“Well Ah’m mighty sorry about that,” Big Macintosh replied. His voice had dropped a little, and his eyes seemed to be trained on the floor. “She hasn’t said much about school lately, ta’ be honest.” Cheerilee was hardly paying attention to what he said. She was looking at Big Macintosh intently, having not seen the stallion in a number of weeks. She saw that he was still wearing his yoke, which almost made her giggle a little. After another moment, she realized that it was her turn to speak.
“Well, yes, that’s understandable. I do feel like she’s trying her hardest, but she just may not be grasping the course material,” she explained. Big Macintosh looked back up at her, his green eyes meeting hers. “And...” she trailed off, losing her thoughts as she looked at his freckles. What was it that she found so attractive about those? “And, I believe it might benefit her to do some at-home studying, maybe a little beyond what she does currently.” Cheerilee was amazed she had been able to make it through the sentence without forgetting what she was saying again. This was all starting to sound like a bad idea to her. She couldn’t keep up the façade much longer without giving away her plans outright.
“Ah think she could spend some more time studying too,” Big Macintosh agreed, nodding his head. His auburn mane bounced a little as he did so, giving Cheerilee another thing to fixate on. He seemed supremely attractive to her. He always had been in a way, ever since they were in school together, but their escapades on Hearts and Hooves day had brought that fact to the forefront of her mind. Hadn’t this been what she had been craving for days? She was finally alone with Big Macintosh, albeit under extremely flimsy pretenses. Why was it so hard for her to follow her mental plan?
“That’s very good to hear. It’s important that a family is involved in their foal’s education,” Cheerilee began. She started to get her mind ready for the next stage of her endeavor. “You know, it’s really funny actually, because Apple Bloom does seem to pay attention when I’m teaching,” she continued. “Why, a few classes ago we were discussing how your brain makes you feel all sorts of emotions, like fear, sadness,” she paused and dropped her voice almost imperceptibly, “love.”
“That does sound mighty interesting,” Big Macintosh replied, adjusting himself to be a little more comfortable in the seat. Cheerilee frowned.
“It does, doesn’t it?” she questioned, laughing anxiously. Her back leg was twitching a bit as she tried to settle herself on her stool. Cheerilee hadn’t caught the scent of Big Macintosh until right then, and she was quickly losing a battle with her self-control. The stallion gave off an aura of apples, mixed with the smell of sweat and earth. He probably hasn’t even bathed today she thought internally, her heart jumping a bit. It took every ounce of willpower within the mare to keep herself from simply pouncing over the desk.
“Is there anythin’ else that ya’ think would help her?” Big Macintosh asked, a look of genuine interest on his face. “Ah’d hate to see her do poorly in school like me or sis did.” Normally Cheerilee would have taken time to correct his grammar, but she feared she wouldn’t be able to string coherent thoughts together soon anyway, so she bit her tongue.
“Well, there are a few specific areas that she seems to be struggling in more than others,” she finally answered. “For instance,” she pushed one of the papers on the desk towards Big Macintosh, “she received a 50 on her last biology test,” Cheerilee said, emphasizing Apple Bloom’s grade. “Now, very few ponies get F’s in my class. You can see why that’s a problem, right?” She hated the fact that she was lying to one of her friends, but she quickly pushed the thought away to avoid feeling too guilty.
“Why, that isn’t even a passin’ grade!” Big Macintosh said, his volume increasing. He furrowed his brow. “Miss Cheerilee, Ah can’t believe Apple Bloom did so badly. Is there a way she could take the test again or somethin’? Ah promise Ah’ll make sure she studies for it,” he beseeched. His eyes were locked on hers, and Cheerilee could feel warmth spreading between her back legs. She had to make her move soon.
“Well I think we might be able to work something out,” she said, her voice audibly quavering.
“What do ya’ have in mind?” Big Macintosh asked evenly, his face softening. Cheerilee’s heart was pounding out of her chest. She wasn’t thinking straight; she could lose her job for this. It’d be worth it. She leaned over her desk, her muscles acting on their own. She was inches away from Big Macintosh, who now sported a somewhat bewildered expression. His musk was overwhelming.
“Mate with me, right here.”
Cheerilee watched as the stallion’s eyes widened in surprise. Silence hung in the air, and all she could think was shit. She was stepping way out of her professional boundaries with this; was sex so important that she was willing to take advantage of Big Macintosh? Of course it’s that important you mule! Now hurry up, you’re losing him, a voice inside the mare cried.
“Miss Cheerilee, Ah’m not sure Ah-” Big Macintosh began before he was trapped in a kiss. Cheerilee had closed her eyes and plunged muzzle-first towards her prey, not caring about how much resistance she might meet, so she was a little surprised to find almost none at all. Big Macintosh had let out a little surprised noise when their lips had met, but he didn’t seem to mind the move so much. At least he wasn’t showing it.
A moment later, their mouths were open, though neither was sure exactly which pony had initiated the change. Tongues met and greeted each other like long-lost friends, each running along the length of the other before meeting in an embrace. Cheerilee thought about how the the tongue was the strongest muscle of the body, and Big Macintosh’s certainly felt powerful as it explored the inside of her cheeks. She couldn't remember the last time she had made out with a stallion, actually recalling that her last kiss had come from a thoroughly plastered Lyra at a Summer Sun Celebration party. Cheerilee wasn’t sure if she and Big Macintosh were doing this ‘correctly,’ but it felt heavenly, and that was what matter to her. She could feel the heat growing near her flank, now joined by the sensation of wetness.
Big Macintosh leaned further into the kiss, moving his arms to be around Cheerilee’s head. She shivered a little as he ran a hoof through her striped pink mane, and even gave a sort of excited whimper when he pulled her in tighter. She could feel the sexual tension that had been between the two of them for years manifesting itself, until she finally had to pull away from the stallion to get some air back in her lungs. Big Macintosh was panting as well, and once again the two ponies locked eyes. Cheerilee saw that her partner’s face had gone redder than it normally was, yet he appeared genuinely enamored as opposed to shocked. Could Big Macintosh have been going through the same mental gymnastics she had?
Cheerilee took a few more shallow breaths while running her eyes over the stallion’s muscular form. She figured she must be grinning stupidly, but her demeanor changed as she glanced near Big Macintosh’s midsection. Over the course of the past few minutes, the stallion’s cock had unsheathed, gradually growing until becoming fully erect. It was now proudly tucked into his chest where she could easily view it. Cheerilee was sure her mouth was hanging open, it being her turn to be in disbelief.
I’ve never wanted anything more in my entire life, she thought as she imagined Big Macintosh mounting her. She was surprised he wasn’t dizzy from the change in blood flow. Hind legs tingling with anticipation, Cheerilee got to her hooves, and the stallion did the same. He was smirking a bit at the mare’s reaction. She was at a loss for words, but she knew she had to take the initiative, believing that Big Macintosh would still be a little too shy to lead.
“Why, uh, don’t you take a seat on my desk?” Cheerilee suggested, her tone a little lower and more subdued than usual. Big Macintosh nodded before putting his front hooves onto her desk and swinging his rump around to sit on it. His stallionhood was now prominently sticking towards Cheerilee, inviting her forward. Who was she to decline?
She took a cautious step towards him, not exactly sure how to proceed at this point. Big Macintosh’s penis was only a little below mouth level for her, so she could reach it without having to maneuver too much. She looked up at him, seeing an encouraging smile. Cheerilee smiled as well, before taking the last step forward. She tilted her head slightly and let her tongue meet the base of the stallion’s cock, dragging it slowly up until finally flicking the tip with it. Big Macintosh let out a little pleased noise as he leaned back, eliciting a smile from Cheerilee. He was putty in her hooves. Invigorated now, she opened her mouth and slid it over the head. She created a little suction, and then proceeded to push her head forward, accepting more of the shaft as she moved her lips further along it.
The scent of being so close to Big Macintosh while he was unsheathed was bliss for Cheerilee. She began to feel the warmth of a trickle of her own juices running down her hind leg. She couldn’t recall ever being so aroused. She continued to fellate the stallion, wrapping her tongue around his penis and gently caressing it as her mouth ran back and forth along its length. Big Macintosh had put one of his hooves on the back of her head, urging her to try to reach the base. Cheerilee narrowed her eyes, determined, and strained her neck as she pushed an inch further and met Big Macintosh’s groin with her muzzle. He let out a long moan of pleasure, one of his hind legs kicking slightly from its position on the teacher’s desk.
She began to bob her head at a quicker rate, causing the stallion’s breath to come in quicker gasps as her mane bounced up and down. Cheerilee thought she might be imagining it, but she could swear that Big Macintosh tasted faintly of apples along with the expected saltiness. She was considering this thought when she felt two powerful hooves force her head once again into the groin of Big Macintosh. She struggled to breathe, the stallion actually obstructing her air flow a bit. She coughed, which eventually led the pair of hooves to be removed from the back of her head.
“Oh, Ah’m real sorry, Cheerilee. Ah...” Big Macintosh trailed off, looking mortified as the deep purple mare continued to cough. “Ah don’t know what got into me.” Cheerilee waved a hoof at him as she finally regained her breath, though she was still taking in large gulps of air.
“No... it’s ok... Big Macintosh,” she said between breaths, assuring her partner with a genuine look in her eyes. She put on another smile and narrowed her eyes as she moved her head back to his genitals, electing to playfully nibble on his balls before rolling her tongue over them. She then raised her head back up to look at his. “But, do you think maybe we could, well you know, get to it?” she asked playfully. Big Macintosh nodded, smiling as he hopped off of the desk. The fire burning between Cheerilee’s thighs was searing now, knowing what was soon to come.
She stepped into position in front of the desk, the nervous tension that had been in her since morning growing stronger. She placed her arms on the surface in front of her, before scooting forward and laying her chest down as well. Her hind legs twitched involuntarily as she raised her tail, swishing it side to side as an invitation. She felt cool air meet her warm and throbbing flesh, sending a shudder through the mare and causing her to flex her vagina involuntarily.
The anticipation was killing her as she lay there, her tail up and exposing herself to the stallion behind her. The noise of wood meeting the floor sounded as she figured Big Macintosh had taken off his yoke. She let out a small rush of breath when she felt a hulking figure descend over hers, watching as a pair of hooves joined hers on the desk. She could feel each of his breaths as his lungs expanded and contracted on her back. Cheerilee heard a few hoof steps as Big Macintosh brought his back legs closer, and her body begged for the next move to be made.
Without warning, the stallion began to slide his cock into the radiant warmth between Cheerilee’s thighs. She moaned, louder than before, as her knees locked up and her hind legs flexed to their fullest capacity. The entry was effortless, as the mixture of the mare’s saliva and her own fluids provided more than ample lubrication. There was a small, slick sound as Big Macintosh continued to push further in, and Cheerilee could feel the farmer’s pulse through the walls of her pussy as he penetrated further than any other colt she had been with. Her sensitive muscles were crying out in ecstasy as the stallion’s thighs met her flank. She almost thought she could feel him pressing into her stomach with the tip of his cock, but she waved the notion off.
Cheerilee continued to writhe as Big Macintosh drew back slightly, causing her stimulation to feel almost like small crackles of electricity. She let out another little whimper as her partner withdrew further, until only the very end of his shaft remained inside her. She felt him move his front hooves so that one was now on each side of her stomach, and then perceived Big Macintosh squeezing her tighter until he brought his hips forward and powerfully drove far into the recesses of Cheerilee. She let out a scream of pure enjoyment and pleasure before digging her muzzle into one of her front hooves and locking her teeth on it. She had to make sure not to make too much noise and attract attention. She hadn’t even locked the door to prevent somepony from accidentally stumbling in on the two of them.
The air became punctuated with the light noise of skin meeting skin as Big Macintosh began to increase the speed of his strokes. Cheerilee couldn’t help but think that the Cutie Mark Crusaders had been right to try to set the two of them up, seeing how well they fit together and how truly perfect this moment was. She swished her tail back and forth against Big Macintosh, causing the stallion’s grip on her to tighten as he continued to plow her like the carrot field during Winter Wrap-Up.
Cheerilee let out a muffled moan as she felt her mane being gripped by a set of teeth. Big Macintosh pulled, not hard, but enough to raise the mare’s head and prevent her from muting her own blissed-out vocalizations. The previously quiet schoolhouse was now echoing with the pants and cries of Cheerilee as her dripping sex was pounded over and over again. Her mind was combining the feelings of stimulation and joy into a new and wholly enthralling sensation for the mare. She felt a bit of drool falling over her lips as she was pushed forward and back, and her mouth was beginning to form a perfect ‘o’.
Big Macintosh slammed into Cheerilee’s flank, he too reaching a physical and emotional zenith. He had shut his eyes at some point, and was gasping heavily as he bucked his hips. The mane in his mouth tasted like sweet roses, and scent the couple was generating began to overtake him. He could feel the mare beneath him taking in quick breaths of air, and he was beginning to feel a faint tingling sensation building within him. The mare’s warm hole pulsated slightly around his cock, the soft walls sliding effortlessly against it as he thrust.
Cheerilee had lost any ability to control her body, giving herself to the stallion fully. She knew she wouldn’t last much longer if he kept this up. Her back hooves began to grow numb, and soon she was just a moment away from the orgasm her body craved. Big Macintosh pushed mightily into Cheerilee’s exposed orifice, finally eliciting a drawn out cry from her. She felt every nerve ending in her body crackle as her muscles expanded and contracted in discordant harmony. She was totally numb to the world around her as her back legs began to slip out from under her, leaving the mare propped up only by the stallion still buried deep inside her.
Big Macintosh continued to hold her up as he felt warm fluid gush over his penis and onto his groin. He spit out Cheerilee's mane and laid his head over her shoulder. The Stallion pushed as far as he could into the half-conscious mare, his own body feeling a wave of cool pleasure spread over it. He was holding his breath as he felt his cock flexing and releasing, discharging more cum than he thought was possible into Cheerilee.
The two ponies remained in that position, totally relaxed and free from thought or worry. Cheerilee was resting face-down on the desk in front of her, beaming broadly and catching her breath as she felt the hot fluid that the stallion had left in her settle. Big Macintosh had his head almost next to hers, wearing a smile and also trying to get his breathing under control. A few seconds passed before he raised his head slightly and nuzzled the side of Cheerilee’s face. He then took a few shaky steps backward, finally pulling out of the mare with an audible pop. Big Macintosh put his front hooves down as well and tried to stand normally, though his legs were being completely uncooperative.
Cheerilee could feel the mixture of semen and her own juices oozing from her still-open vagina. A bit dripped off of her and fell to the ground, the subtle sound of it being the only thing shattering the silence of the schoolroom. She woozily backed up and put her hooves on the floor, her eyes half-lidded as she turned to gaze at Big Macintosh. He was grinning back at her, more earnestly than she’d ever seen. The two stepped towards each other, meeting in a loving kiss for a few seconds before pulling away to stare at the other’s eyes.
“This can’t be the last time we do this,” Cheerilee said, her heart rate finally approaching a normal pace. Her tone was at less than its normal level of buoyancy, but it still sounded unmistakably like her.
“Nope,” Big Macintosh answered, lowering his neck and shimmying back into his discarded yoke. Cheerilee laughed a little as he did so, thinking about how tense she had been earlier. Everything had gone perfectly, and she was divinely happy to be standing there with Big Macintosh, the two of them both having connected on the deepest of levels.
“Do you promise you’ll try to see me again? This isn’t going to be another Hearts and Hooves day, right?” she asked, half in jest and half in sincerity.
“Ah promise,” Big Macintosh said as he leaned forward to plant another kiss on the mare. The two ponies each nuzzled the other’s snout, sending Cheerilee’s heart soaring. Both took a step back after a moment, as pleased as they could ever imagine being. “And, well, thanks for takin’ care of Apple Bloom’s grade an’ all; it means a lot ta’ me,” Big Macintosh admitted. Cheerilee’s cheeks reddened as she dropped her head.
“Oh, um, don’t mention it,” she replied, having forgotten the afternoon’s premise.
“Ah need ta’ get back ta’ the farm before Granny gets too worried,” Big Macintosh said, sounding as if he’d really rather stay. “Maybe Ah’ll come by your house next Tuesday, around seven?” he asked, crossing his hooves nervously.
“I’d love that,” Cheerilee responded, her tone regaining its characteristic bounce. Big Macintosh nodded and gave the mare one final kiss before turning around and exiting the schoolhouse into the orange hue of the late afternoon.
Cheerilee let out a content sigh and turned to look back at her desk, which was spotted with drips of various fluids. She then looked around at the similar liquids on the floor, which she was still adding to. Just another thing to clean up, she thought, knowing that she wouldn’t have traded the afternoon’s exchange for anything. It doesn’t really matter though;
I’ve got a special somepony now.
