Chapters The bell rang, signaling the beginning of a new day at the Ponyville School. The sky was blue and the air was crisp and pleasant. The autumn leaves were turning all shades of brown, tinging the trees with their specific brand of bronzed beauty. It was almost as if Van Foal, the famous pony artist prodigy, had taken his brush and painted a picture of absolute gentility across the landscape. The clouds were few and far between, and they held their puffy shape quite well. Not a gray cloud dotted the sky, and the foals who now marched into school were very thankful for this fact.
There was one underlying issue that betrayed their inner sense of wonder as they settled at their desks that day: a test. This wasn’t just any test. It was a test in the skills of arithmetic, something which nopony, with the exception of maybe Princess Twilight, enjoyed. The fillies and colts moaned in disgust as Cheerilee trotted to the front of the classroom, announced the exam, and began distributing it. Nothing could have ruined this absolutely perfect autumn day more than a proctored piece of paper that eschewed fun in favor of targeting the one subject that they hated.
“Ugh…” Apple Bloom said, seated next to her best friends, Sweetie Belle and Scootaloo, “did y’all study fer this exam?”
They both nodded, and the young country pony pounded her head on the desk in a superb demonstration of reactionary exaggeration. She knew that she had not studied as much as she should have, but instead spent the evening trying to figure out what the noises were that came from her big brother and big sister-in-law’s bedroom. It sounded like their bed was thumping against the wall, followed by various groans and grunts.
“Yeah, I studied,” Sweetie Belle said, “in between bouts of Rarity’s drama.”
“Drama?” Scootaloo asked.
“Yep. Ra Ra asked her to create the costumes for her upcoming Equestrian tour, and she’s scared that she won’t be finished on time. So, she spent a lot of time on her special ‘crying couch’”
“Is she close to bein’ done?” Apple Bloom asked.
“Yeah,” Sweetie responded, “she’s really close. She just won’t admit it.”
“Okay, my little ponies,” Cheerilee said, breaking into their small conversation, “the tests have been handed out. You may begin…now.”
Silence fell over the classroom as each foal began getting to work. Their facial features went through a mixture of happiness, disgust, sadness, and pain as each new problem made itself known. Cheerilee had made it a pastime of hers to watch these changes, and she had to stifle giggles whenever one of her students finally broke through the barrier and resolved the issue at hoof. They would nearly jump for joy, then remember where they were and what they were doing, and put a damper on their emotions.
But there was another reason she paid attention to her students so closely, and it was the biggest secret she had. Cheerilee was a closet fillyphile. She loved the small female ponies who came to see her each day, with their bright eyes and small, happy smiles. She had a soft spot in her heart for each one, and considered them all very attractive. But one pony out of them all had completely swept her away with both her brain and her beauty. That pony…was Sweetie Belle. With her bright green eyes, beautifully perfect mane, and amazing way of understanding the curriculum, Cheerilee had fallen head over hooves in love.
Cheerilee’s love of fillies had been difficult to grasp, and even now, she was wrestling with her feelings. Some part of her knew that it was wrong to think of young ponies in such a way, and that she should be out trying to find a stallion her age. But all the same, every time she saw Sweetie Belle, her heart pounded out of her chest. She had even taken to watching her student play with the other ponies, hoping that an inadvertent flick of the tail might open the door to viewing Sweetie’s most carefully guarded treasure.
I know what I want, she thought as her eyes drifted slowly over Sweetie’s small body, no…I know what I NEED. Ugh! But it’s so wrong! She’s my student! I’m her teacher! The maintained relationship between the master and the pupil needs to be kept professional! That’s what they taught us at the university!
Her stomach tied itself in knots as she continued staring daggers at the unsuspecting filly. Her mouth went dry as she felt her vaginal glands begin leaking. Her mind went to a very dirty spot, and began imagining the filly tied to her desk and at her mercy. She would dominate Sweetie until the poor pony fell unconscious from exhaustion, and then she would gingerly remove the restraints and transport her home for some much needed rest. She could come up with some excuse to give Rarity for why her sister was so tired, but she needed to experience this. She had to love Sweetie Belle. Her heart would not stop quivering until she had done so.
The rest of the day passed quickly, and the bell rang. Happy squeals followed this event as the foals all scrambled to be the first one out of the door. Cheerilee reminded them of their field trip the following day to the Ponyville Museum, and the pizza party that would happen afterward. The young ponies all reacted with excitement at the news and they seemed to hurry out of the room even faster. Cheerilee knew that her time to be with Sweetie Belle was short, so she called her over to the desk and prepared to bare her soul.
“Yes, Ms. Cheerilee?” Sweetie asked.
“Please, sit down,” Cheerilee said sweetly.
The filly did so, plopping her soft, wonderful rump on the wooden stool opposite her teacher. Cheerilee’s eyes maneuvered right and left, attempting to get a better view of Sweetie’s backside. “Um…is everything alright?” The young pony asked, “you seem distracted.”
“Who, me? Uh, no, no, I’m not distracted,” Cheerilee said as sweat began beading on her forehead, “I’m just…very happy to have you here.”
“So, I didn’t do anything wrong?”
Cheerilee shook her head. “Quite the opposite, actually. I’ve called you over here, because you’ve done something right.”
“I have?”
Cheerilee nodded. “Indeed, you have, my dear little Sweetie Belle.”
With those words, the teacher got up and trotted around to sit beside her pupil. Sweetie’s green eyes betrayed a mixture of emotions that Cheerilee couldn’t quite read. She could tell that there was confusion, but it was undermined by a thick layer of curiosity. There also seemed to be a bit of uncertainty, and it was all brewing into a soup of doubt.
“Um…Ms. Cheerilee?”
“Sh…” Cheerilee said as she ran her hoof along Sweetie’s mane. The feeling of her soft strands of hair was almost too much for the closet fillyphile. “It’s okay, Sweetie. I just want you to know something.”
“What’s that?”
“As much as I love all you little ponies, I think you’re my favorite out of the whole class.”
“Your favorite?”
“Yes, my dear. I’m…in love with you.”
“In love with me?!” Sweetie asked as she instinctively moved away from her teacher. This pony that she trusted and admired as one of her closest friends had turned into something that she wasn’t sure she liked. She suddenly became afraid of what would happen next, and the one mare she would normally turn to for comfort in these times was the one causing them. She cowered a little bit and quivered, but Cheerilee wrapped her up in one of the warmest embraces she’d ever felt.
“Don’t be afraid, my dear,” Cheerilee said, “I’m not going to do anything to harm you.”
“You…you won’t?” Sweetie asked.
“Of course not,” her teacher responded, smiling, “I only want to make you the happiest filly in all Equestria. I know it’s…unorthodox, but I need to be honest with you and with myself. I’ve been tossing and turning at night because I kept these feelings repressed. But now that I’ve come out and been open with you, I feel so much better!”
Sweetie backed up a bit and gave her teacher a look that was somewhere between soft and hard. In that grey area, Cheerilee found herself falling in love even further. She loved it when Sweetie didn’t quite grasp a concept, because that meant that she got to open her young friend’s eyes even further. She intended to open them all the way once they got back to her home. She could tell that, even now, Sweetie was beginning to comprehend the depth of her feelings and respond to them. The young pony’s eyelids began shutting, and she cuddled deeper into her teacher.
“Ms. Cheerilee,” Sweetie whispered, “I just…don’t quite understand. I’m only a filly, and not a special one, either.”
“Now, darling, that’s not true. You’re very special to a whole lot of ponies, and especially to me.”
“But why?” Sweetie asked as she suddenly pulled away from the embrace and turned to look out a nearby window. “Why me? Why didn’t you fall in love with one of the other fillies? What do you see in me?”
Cheerilee took a moment to ponder her response. Her love for this young pony would not allow her to be so blunt with her as to overwhelm her, but she also wanted to be completely straightforward. This was the pony she wanted to love forever, that she wanted to mate with. She knew that some part of these yearnings was dastardly and wicked, but she didn’t care. She wanted to be happy, and she wanted to make Sweetie Belle happy.
“I fell in love with you because you were always the first in class to greet me, and the last to bid me farewell. You’re always trying to discover new things, and I guess the teacher part of me is quite taken with that. You’re a wonderful friend, and an excellent student. That, and your…physical acumen is quite impressive. Frankly, you’re beautiful!”
“Beautiful?”
“Yes, Sweetie Belle!” Cheerilee exclaimed as she maneuvered her way beside her student once again. She gently latched onto Sweetie’s face with a hoof and pulled it towards her, attempting to delve into the depths of her green gaze. It was pale, yet absolutely breathtaking in its sheer subtlety. It could be difficult to tell what the filly was thinking from the look in her eyes, adding to the mystery that Cheerilee wanted so very much to unravel.
But Sweetie yanked her face away. “You can’t love me,” she said blatantly, “I’m your student, and you’re my teacher. We need to remain friends, at the most.”
The words tore into Cheerilee’s heart, but she pressed on. “Sweetie, please,” she said, “listen to me. We’ve transcended the plane of teacher and student and turned into something more.”
“We have?” Sweetie asked, turning back to face her mentor.
“Yes, my love, we have,” Cheerilee said, “and we must be willing to act on it. There’s nothing in this world I want more than you. I am a fillyphile, but I’m a fillyphile who’s fallen in love. Now I don’t want anything romantic from anypony else. Please, Sweetie Belle. Come home with me and spend the night. I cannot stand another evening of being alone.”
Sweetie was shocked at the outright promiscuity being put on display, and she thought about sending for the local authorities. Then she remembered that what Cheerilee was doing was not against any kind of Celestial law, so that plan went flying out the window. It was common knowledge that a colt or filly’s first sexual or romantic experience was often with a parent or trusted friend, because they would not be harmed by them. In this circumstance, Cheerilee was the trusted friend. Sweetie knew that her teacher would never touch her without permission, and she also knew that the dark pink mare lived to make foals happy. I just never realized that the happiness was so…personal, she thought.
“Ms. Cheerilee-“
“No, dear,” Cheerilee said in a voice that was as smooth as silk, “no more formalities. Please, just call me by my first name.”
“Okay, Cheerilee,” Sweetie said, “have you ever…been with a filly before?”
Cheerilee’s eyes looked at the ground and then back at Sweetie. “Once,” she confessed, “I had relations with a pony around your age. Her name was Smooth Swirl, and she was amazing. I was in college when I discovered my illicit emotions regarding fillies, and I got sent to Canterlot Elementary to do my student hours. When I met Smooth, my heart pounded out of my chest and I immediately asked her out. To my great surprise, she agreed, and the night was capped off by an hours long session of sexual gratification. That was how I knew I loved fillies. Nothing drove me like you young mares did.”
Sweetie smiled. “It sounds like you and Smooth had an amazing experience.”
“We did, indeed, Sweetie Belle. But she’s in the past, and I’m trying to solidify the future. Sweetie Belle, will you come home with me? I need somepony tonight.”
“Well…” Sweetie said as she tried to make her decision. On the one hoof, going home with her teacher meant a night of pleasure, and she knew that she needed it. Her habitual masturbation had tapered off in the last few weeks, and her small vagina was crying out for somepony to touch it. But on the other hoof, her night of carnal relations could lead to trouble with Rarity. “I just don’t know,” she said.
“If you’re worried about your big sissy,” Cheerilee cooed, “I’ve got an excuse for you. Since she trusts me, I’ll just tell her you came over for help on your homework.”
Sweetie smiled. “You know, Cheerilee,” she said, “you have a way with words. The fact is, I’ve often…well…pleasured myself to your picture. I’ve thought you were pretty for a long time, but today sealed it. You truly are the best thing that's ever happened to me, and I cannot deny my own feelings any longer. I…love you too, my teacher.”
Author's Note
Hey, everyone! Hope you're enjoying the story so far! I promise that the sex is coming in the next chapter or two. I wanted to make this more of a romantic story instead of just a straight up clopfic, and I wanted to give Cheerilee and Sweetie some context. So, the steamier stuff got put on hold until the later chapters. Thanks again for reading!
The kiss was a magical experience for both the older and the younger. It was almost symbolic, representing the joining of one generation to the next. As soon as Sweetie reciprocated Cheerilee’s love, their lips met, sparking the next chapter in their lives. The love that screamed from the gesture was so thick, one could almost feel it tightening its hold. In a way, they felt a giant, disembodied hoof pushing them closer together. The magnetism they shared was real, and they were experiencing every single amazing facet of it.
After a moment, they needed to break apart for air, but their eyes never left each other. They were each entranced by their new lover, though some sense of guilt ran through them. After all, this was a mare loving a filly. It just didn’t seem right, though it felt so. Their smiles soon chased any sense of doubt away, and they wordlessly left the classroom and headed towards Rarity’s boutique. As they trotted along, nopony took any notice of them. Sweetie and Cheerilee were seen together in public all the time. But nopony could have known what had just occurred, and the new relationship they now enjoyed.
After giving Cheerilee’s excuse to Rarity, they headed for the teacher’s home. Sweetie Belle was intensely excited, as she knew that something wonderful was coming. She had seen enough of her sister’s secret pornographic films to realize what was going on, and she wanted every single part of it. The writing was on the wall, with Cheerilee as the scribe. Sweetie tried to steal glances at her teacher’s vagina as her tail swished from side to side. But the older mare caught on to her young lover’s game, and managed to maneuver her tail over her jewel.
“Aw…” Sweetie said when Cheerilee did so.
The fillyphile chuckled. “You’ll get it when we get home,” she said softly.
It didn’t take them long to reach Cheerilee’s cottage. It was a simple, two-story house, with everything normal of the many similar homes that lined Ponyville’s cobblestone avenues. It had a spacious living area, a sizable kitchen, and a master bedroom and bathroom upstairs. There was also a guest room and a small bathroom to go with it. It seemed to be a nice place, and Sweetie took to it like a fish to water. She settled on the couch, looking up at Cheerilee with a rather cute, pouting expression.
Cheerilee knew exactly what the filly wanted, but she wasn’t willing to give just yet. So, she sat down and cuddled her new lover. After gently kissing her forehead, she said, “not now, baby. You’ll get to experience it in a few minutes.”
The teacher loved teasing her student, but she was dealing with her own impatience. She had managed to sneak a peek at Sweetie’s rather lush backside, and her body quivered with excitement. She truly loved this little pony, and she wanted to ensure that her filly was the happiest filly in all of Equestria. But things had to fall in line in a certain way. Just stick to the plan, Cheerilee, she told herself, you’ll get that filly’s pussy in time.
She quietly got up and began preparing them some dinner, but in a heavily sexualized manner. This time, she made sure her tail was not blocking her young filly friend’s view. Sweetie, for her part, took to staring at her teacher’s pussy like it was the last thing on Earth. She wanted to gallop over and touch it, but she was scared that it would be crossing some boundary. So she stayed put, happily toying with her own small vagina. Soon enough, she began leaking fluids and moaning. Her hoof made small circles around the lips, before finally finding its way inside. She had never had so much fun masturbating before, and her pumps became harder. Cheerilee’s flower had blossomed, and she was happy to help pollinate it.
“Oh…oh…oh!” She moaned as her small hoof continued its work, “Cheerilee, I can see everything!”
Cheerilee smiled to herself as she continued her cooking. “You like watching me make dinner?”
“Uh-huh!” Sweetie practically shouted as she felt her climax coming. “Oh…Cheerilee…I…I’m gonna…I…OH!”
Her body could take no more, and her vaginal lips spouted out volley after volley of beautifully transparent liquid. She took the opportunity to clean herself up a bit, and then got up and trotted over to where her teacher was setting their food on the table. Her breathing was rapid, but a loving hoof to her chest managed to relax her. “Holy fucking Celestia,” Sweetie breathed.
Cheerilee chuckled as she pulled Sweetie’s chair out for her. “It’s fun, isn’t it?”
“Yeah!” Sweetie said as she sat down.
Her teacher quickly joined her at the opposite side of the table, and the two began devouring the rather delicious quesadillas that she had made. They sat in silence for a while before Sweetie opened her small mouth. “Was that…okay?” She asked, referring to the earlier incidents of pleasure.
“Of course, love,” Cheerilee said, “I wanted you to do that. That’s why I purposely kept my tail out of the way. After dinner is when the true fun begins, though…”
Sweetie didn’t say anything, but her body language became even more enthused than before. She nearly leapt from the table in sheer joy. Her teacher, the mare that meant more to her than anything else in the world, was going to have sex with her. She would finally understand what Rarity constantly bragged to her friends about when she thought nopony was listening. Damn you, sis, Sweetie silently cursed, I’m gonna be all grown up by the time this evening is over. When Cheerilee takes my virginity, I’ll finally have something to brag to my friends about. You’re not the only slut in the family…
After dinner, the two lovers went upstairs and mentally prepared for the inevitable. For Cheerilee, it was easy, as it would be a repeat experience. She had already slept with one filly, and she was well versed in the art of making a young pony happy. She knew that Sweetie would be very sensitive in a lot of areas that older mares weren’t, so she made an internal note to target those places. Tonight is the night we fulfill everything that we were meant to be, she told herself, once Sweetie Belle is lying on her back, I’ll finally break through every barrier left between us.
For Sweetie Belle, it was a little more difficult. She was definitely in love, but she didn’t quite know what to expect. Sure, she had seen sex performed before, but that was between a mare and a stallion. Rarity did not keep lesbian porn in her secret stash, so she had never witnessed such things. She didn’t know if her new lover would be gentle or rough. She also didn’t know how penetration would be achieved. But she knew one thing: she wanted this to happen. She needed this to happen.
“Are you ready, darling?” Cheerilee asked sensually.
“I was born ready,” Sweetie said.
“Very well, get onto your back, spread your legs, and I’ll begin.”
Cheerilee began by softly sniffing at her young lover’s most sensitive area. Her reasons for doing so were twofold: one, so that she might breathe in the intoxicating heat that Sweetie was involuntarily releasing, and two, so that her warm breath might excite the young pony. Sweetie’s moans were soft and gentle, and they came with every single exhale of her new lover’s nose. She was headed for some kind of sexual Valhalla, and Cheerilee wanted to push her ever so slightly towards the edge.
Her sniffs soon turned into gentle, teasing licks. She flashed her tongue around Sweetie’s vagina over and over again, turning it into her personal plaything. Her hooves came up and wrapped themselves over Sweetie’s lower chest, tenderly rubbing her fur. The filly’s moans became ginger, and she gave her teacher a very loving look. Every single time Cheerilee’s tongue swiped around her private area, she felt a new sensation. It wasn’t just the magnificent pleasure that flooded through her body, but also a wondrous feeling of love and devotion. This wasn’t simple sex, it was truly an affair of love, and Cheerilee was an absolute professional when it came to such things.
“Cheerilee…” Sweetie said softly as her teacher continued to tease her. She would run her tongue around the filly’s pussy lips for one lap, and then focus on her vulva and clitoris. Then, she would repeat the pattern. She knew that her young lover wanted more, but she also wanted to teach her that this kind of love was a slow, methodical process. She wanted Sweetie to experience every single aspect of what they had committed themselves to. She didn’t say anything, and she wasn’t stereotypical when it came to matters of bedtime manners. She didn’t scream or curse at the filly. She simply focused on what mattered most: her love for Sweetie Belle.
It drove her tongue through the aforementioned pattern over and over again. She loved hearing the gentle cries that came from the filly’s small mouth. Her wordless love was translating beautifully, and both mares were experiencing the height of passion. Fireworks exploded in Sweetie’s head with every swipe that Cheerilee made, and her moans gradually intensified. But even through their increase in volume, they still carried that element of love and gratitude befitting of such an experience. Frankly, Cheerilee’s smooth tongue was pouring gasoline onto Sweetie’s incredibly potent fire, and the filly was happy to let the proceedings burn as they would.
Soon, Cheerilee felt her lover’s climax begin to build and she stopped her oral maneuvers. She bent her head up and smiled at Sweetie, licking the last of her sweet juices off her face. She hummed in a suggestive manner, but remained purposely dumb. She wanted to create an atmosphere where Sweetie would be comfortable, before she began the traditional profanity filled squealing. She crept over the small body beneath her and took Sweetie’s mouth in her own. Their tongues danced a tango of beautiful similarity as their moans overtook them. Their eyes were completely shut, yet they felt wide open. They knew that they lay in the forelegs of somepony who understood everything about them. All their sorrow, love, happiness, anger, and pain were now shared.
When they broke, Sweetie looked up at somepony who, just twenty-four hours prior, had merely been her teacher. “Cheerilee,” she said, “I…can’t believe we’re doing this. But I don’t wanna stop. Please…make love to me.”
“I will, darling,” Cheerilee said.
She began by placing her pussy right above Sweetie’s. After an encouraging nod from the filly, she began gently rubbing their sensitive parts together. Sweetie’s cries of pleasure were absolutely magnificent to the ear, and Cheerilee found that her hips moved faster and faster every time her student squealed. Her voice was as sweet as honey, yet as sharp as the jagged cliffs that lined the Hoofalayan Mountains. It begged the dark pink mare for more, and she gladly gave. She considered herself a generous pony in bed, and she crouched down and began thrusting even faster.
“Oh! Oh! Cheerilee! Fuck me!” Sweetie cried, “I love you so much, baby! Oh, please! More! More! More!”
Pleasure beyond pleasure screamed its way through the filly’s veins as her beloved teacher continued her work. She was in a trance, completely intrigued by the mare above her. They alternated between kissing and screaming as Sweetie began instinctively bucking her lower half to match Cheerilee. Through all of this, her teacher remained purposely stricken with regards to words. Oh, she wanted to curse. She wanted to scream at the filly, and release all the amazing feelings that assaulted her mind. But she stuck to her modus operandi, and began pounding Sweetie’s small body with reckless, yet wordless, abandon.
“OH! OH!” Sweetie screamed as she finally reached the top of the sexual mountain, “OH, YES, CHEERILEE! THAT’S IT! RIGHT THERE! FUCK ME, YOU BITCH! OH! OH! YES! YES! OH! MORE! OH, CHEERILEEEEEEEEEEEEEEEEEEEEEE!”
With that squeal, a torrent of fluids rushed out of Sweetie’s tiny vagina, coating both of their lower halves. Exhausted from the relentless session, Cheerilee collapsed beside her young lover. Their pants were thick and filled with fatigue, yet it was a happy fatigue. It betrayed their love for each other and for the actions to which they had both committed so much. To be frank, it was the most amazing experience either mare had ever had. It was at this point that Cheerilee decided to break her dumb streak.
“I take it, you enjoyed that?” She asked between pants.
“Oh, Cheerilee, baby,” Sweetie said breathlessly, “it was so amazing! I just…had no idea that literal sex felt that good!”
“You seem to be well versed in the art,” Cheerilee said, “tell me, where did you learn all this?”
Sweetie blushed heavily, but decided to be open. “My sister has a secret collection of pony porn stashed away at our house. She doesn’t know it, but I know exactly where it is. One time, I peeked through the door and saw her masturbating to one of the films. She was crying out, and at first, I thought she was in trouble. But then I looked over and saw the two ponies having sex on TV. It was a mare and a stallion, and they both caused a reaction in me. I knew I wanted somepony to shove something inside me someday. I wanted to do something to a mare someday as well. I guess, that was when it started. Today was the ultimate fulfillment of a dream…and I have you to thank for it, my love.”
Cheerilee smiled, near tears at the compliment, and bent over to kiss her young lover on the cheek. “It was my pleasure, baby,” she said, “you know I want nothing more than to make you happy. But now, I need something…from you.”
“What’s that?”
Cheerilee suddenly reached a hoof under the bed and rolled out a toy. When she brought it up and laid it on the sheets between them, she swore that Sweetie began salivating. It was a medium size plastic penis, and it was one of the best sellers from the catalogue that Cheerilee discreetly subscribed to. She had played with it before, and it had brought her to one of the most glorious orgasms she had ever experienced. But now that she had a filly to love, she wanted nothing more than for Sweetie to ravage her vagina with it.
“I need you to shove one end of this into your pussy, and then mount me…”
To be continued…
Sweetie had no small reservations about putting the toy in such a sensitive spot. Even though a part of her was throbbing and wanted to go through with it, some sense of nervousness held her back. She had already exposed her most private organs to her teacher, and had them touched and caressed in ways that she never thought possible. It would only be right for her to return the sexual favor. But all the same, she had never actually been penetrated before. She had seen it on camera, but had never experienced it. So to say that the quivering she now experienced was from excitement would be more than mildly deceptive.
“I…I just don’t know,” she said.
Cheerilee noticed the worry painting her beloved’s face and turned to face her. “It’s okay, Sweetie Belle. All you have to do is just gently put it inside you, and then put the other end inside me. It’ll feel amazing, I promise!”
“But…doesn’t the first time…hurt?” Sweetie asked. She had seen a film once where the stallion took the mare’s virginity, and she couldn’t stomach the screaming. She knew that the rest of the experience was very pleasurable, but she didn’t like the idea of having to suffer in order to feel it. Her nerves became even more uncontrollable, and she felt tears begin brimming. She wanted so much to make Cheerilee happy, and she felt unable to do so.
Her marefriend saw the sadness evident in her face and pulled her into a gentle hug. She let Sweetie cry for a moment, before softly kissing her cheek. She slowly sat back, without releasing the nervous filly, and looked her in the eye. “Sweetie, baby, listen to me. I love you, no matter what. If you’re too nervous to go through with this, that’s fine. We can wait.”
“No,” Sweetie said as she pulled out of the hug, “I want this. But…I just don’t want the pain that goes with it.”
“I understand,” Cheerilee said compassionately, “because I remember when a stallion first slept with me. It hurt for a few seconds, but then the sheer ecstasy took over and I rode him to oblivion. There’s nothing wrong with a little pain to get to a lot of pleasure, darling. But, like I said, I’m willing to wait if you want to.”
Sweetie shook her small head. She knew that this would seal her love for her teacher forever, and she felt that she was only a few hoof steps away from it. She was just a little wary of taking them. But then Cheerilee, who had been backing her all along, suddenly threw her weight under the young pony, and she was able to face the prospect without fear. She felt all of her doubt wash away in the beautiful green eyes that cast their love down at her.
“Would you like some help?” Cheerilee asked.
Sweetie nodded, and her teacher maneuvered one end of the toy into an upright position. She then instructed her student, as gently as if she were teaching her a regular lesson, to squat her rump over the tip. Once this was done, she moved her hooves up over Sweetie’s flanks, and gently lowered her onto the plastic penis. Sweetie howled in agony as she felt it push ever deeper into her body, breaking her hymen and ensuring that her naiveté was destroyed forever. Her rump quivered as her vaginal muscles finally managed to take control of the toy, leaving one end poking outward.
Cheerilee narrowed her eyes and gently began to suck on the toy. To her delight, she found that Sweetie’s hold was ever so loose, and she began working the toy back and forth. Each new oral thrust elicited a deeper moan from the filly, and Cheerilee was happy to administer more. It wasn’t loose enough to where the toy tumbled out, but it was just so to where it could pleasure Sweetie. Soon enough, though, Cheerilee felt an urge bloom from her own flower, and she stopped her small blowjob. She bent upwards to kiss Sweetie, before turning around and asking her to proceed with the mounting.
Sweetie, having been exposed to this kind of thing via her sister’s secret stash, immediately clambered on top of her teacher. She attempted to move around so that her partner would be comfortable with the mating, but no matter what she tried, she’d always stick an errant hoof here or a misplaced joint there. She felt terrible, but her teacher gently encouraged her until she finally managed to find the right position. She lifted her rump, nodded at Cheerilee, and then pushed her way inside.
Cheerilee howled at the explosion of pleasure that laced her body. It ran its way up her spine and practically melted her mind. She knew that it was destiny for her and the beautiful filly to be together, and their first sexual session was fulfilling all of that. As Sweetie began slowly thrusting back and forth, the dark pink mare saw stars in front of her eyes. She hadn’t been with a filly since Smooth Swirl, and she had forgotten just how amazing they could be in bed. Sweetie’s muscles worked their way into a frenzy, and soon the two mares were moaning right alongside each other.
“Oh…oh…Cheerilee,” Sweetie groaned as she thrust, “this feels so good! I think it’s going deeper every time I pump!”
“It is, Sweetie,” Cheerilee panted, “that’s what makes it such a great toy! Oh! Oh! Oh! You’re pounding so deep! Come on, sweetheart! Come on, my love! Keep fucking me! Oh…yes! I needed this so badly!”
Their cries went unnoticed by the rest of Ponyville, which wandered by completely oblivious to the beautiful scene of love between a teacher and a student. Had they known, their reactions would have been mixed, as some ponies found that making love to foals was odd and weird, while others found that it was a beautiful way to show affection. Even Princess Celestia herself had an opinion, telling everypony that ponies had a choice in love, and some chose to love foals. Cheerilee was one of those ponies, even though the EEA had strict rules forbidding such interactions.
But those rules did not apply in this bedroom at this moment in time. The filly and the mare seemed frozen within some kind of self-contained continuum. It was a world where they were the only two ponies who existed, and their shared vaginal intercourse was the ultimate prize. They had exposed themselves to each other, body and soul, and they knew they could never recant their feelings. As Sweetie’s thrusts became harder, and their cries became louder, their love somehow grew.
“Oh! Cheerilee! I feel like I’m gonna explode all over this cock!” Sweetie cried.
“Yes! Fucking cum for me, baby!” Cheerilee howled back at her lover, “please, baby! Shoot your Celestia damned love juices all over that big toy! Oh, baby! OH! OH! OH! OH! FUCK! FUCK! FUCK! OH! YES! OH!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!”
“AHHHHHHHHHHHHHHHHHH!!!!!!!!!!!” Sweetie screamed.
Their conjoined orgasm was a magnificent thing to behold, and the two mares collapsed in exhaustion afterwards. Cheerilee managed, somehow, to pull down the covers and they cuddled underneath them. Their pants were rapid, and their sweat stained the sheets, but they were each incredibly satisfied. They knew that they would never betray the newfound love they felt, and their actions that evening had solidified it.
“Sweetie,” Cheerilee said as she buried her face in the filly’s shoulder, “you’re fantastic.”
“You’re not so bad, yourself,” Sweetie managed to get out as she instinctively ground her body against her teacher’s.
“Please, baby,” Cheerilee said, “stay with me forever. Be my mate, even in secret.”
“I will, my love,” Sweetie responded, kissing her teacher tenderly, “I promise I will.”
