Cheerilee took in a deep, quivering breath as she looked over her leaving class. Full grown fillies and colts she had known since they were small were passing her by, and all she could do was smile. Each one hurt though, as she knew what she did today was not only wrong, but cowardly. It should be her whose body was to meet the hands of one never supposed to touch it, not… Cheerilee, this is the best you can have. Just enjoy what you’ll get here, and you’ll be fine. It’ll be all you need. It took all of Cheerilee’s will not to let the tear that formed in her eye at the last thought to fall.

Meanwhile, in her peripherals, she could watch Silver Spoon take a final, deep breath in, before walking over to Button’s desk. Cheerilee had heard Sweetie talking to him just a moment ago about video games, and hanging out that night, and the older mare hoped he might still act on those plans, even after what her and Silver had planned.

Sweetie Belle pouted at whatever Silver Spoon was telling her, and she hoped that the young, grey mare wasn’t messing up her own plan. She shut her eyes, her fingers wrapping around her knees as she realized what that also meant. Just relax, Cheerilee. So long as you aren’t the one touching him, it’s fine.

“So, what’s up, Cheerilee?”

A shiver of hot arousal rolled through Cheerilee’s body, and it took every ounce of her will to look up to the cheerful voice that had spoken to her. There she saw the same old stupid grin shining orange eyes, but now… now they belonged to a real stallion. A stallion making a difference, catching the attention of mares, building a herd I should join. Cheerilee clenched her hands again as the thought rolled through, but couldn’t dismiss it properly, not with Button right there. “Well, yes, but first, Silver Spoon, can you please lock the door?”

The gray mare’s cheeks flared up with crimson hues as she nodded, and Cheerilee could see Button nervously fidget. He had good reason to, as even Cheerilee could tell that out of all the mares he had started hanging out with, Silver Spoon was not the one he expected to find alone time with. Or her, for that matter. “So, this morning, Silver Spoon decided to talk to me about a rather… special worry of hers. It’s concerning the matter of the mares you are growing ever closer to.”

Now it was Button’s turn to blush, and to grab his arm in the cute way he did when he got nervous. Cheerilee prayed that he could not smell the drop she felt sliding between her folds. “They are pretty amazing, but,” he paused, turning to Silver Spoon, “I thought you were finally willing to trust me with them, even Diamond Tiara.”

Silver Spoon let out a small harumph as she looked to the side, the tassels on her jacket bouncing slightly with the motion. “I have conceded that whatever they feel for you is real, and that… and that you’re not a bad colt. Today isn’t about being good or bad though.”

Button’s brow furrowed even more as he turned back to Cheerilee, who was still smiling at the two, even as sweat was collecting on her brow. “Then, what is it about?”

Cheerilee took in a deep breath, her hands slowly opening the drawer just underneath her desk. There sat a six inch ruler, usually meant to be loaned out, but she suspected that it would be burning by the end of the day. “Well, while we have covered such topics in the past, with so many of my pupils being under your care and growing closer to you-”

“I-It’s only two, really. At least, I think it is.”

Cheerilee gripped the ruler harder as another wave of need pushed its way through her body. How could one attract so many, while still being so innocent? “Silver Spoon says three, as where Diamond Tiara goes, she will follow, even with you.” She waited to let the grey mare nod, even if the younger pony would not look at either of them now. “In that vein though, she wants to make sure that the one who ends up with her friend is tr-treated right.”

Button frowned at that, his brows furrowing ever deeper as he stepped closer to Silver Spoon. “I thought we were done with this! I don’t plan ooooo-”

Cheerilee slid the ruler underneath her skirt, soon feeling the rough touch of it’s wooden edge against her underwear as she watched what was to happen begin. The stunned word from Button was also freezing Silver Spoon from continuing her plan from this morning, so instead she was just standing there, her jacket undone, and her well endowed breasts completely bare to Button now. After a long, painful ten seconds of waiting, Cheerilee heard the words that doomed her that day.

“I want to make sure you treat Diamond right… sexually, too.”

Button’s head looked like it almost lit on fire with how fast it became completely red. “Wh-what? E-even if I thought this was right, sh-shouldn’t we do this in private, instead of, you know, in front of…” He became quiet, staring at Cheerilee, who was using every ounce of her will to give him a small, confident smile, even as the ruler between her thighs was pulling her underwear away from her slit.

Silver Spoon shook her head as she stepped closer and grabbed ahold of Button’s hand. “No… we shouldn’t. I’m still new to all of this myself, and,” she stopped for a moment, blinking to try and stop, and failed to stop, a tear from falling down her cheek, “and I need to somehow have leverage on you, so that when I do get some experience, it’s even slightly as I dreamed it would be.”

Cheerilee felt her heart go out to the young mare as the two ponies stared at each other for a few moments. While this morning had been the first time her suspicions had ever been confirmed that the gray mare had feelings for her leader, she had always suspected it. She was not there to judge relationships, or mend broken hearts. That was Silver’s job. She was there to teach, and as Button pulled Silver Spoon in close, and their lips met, Cheerilee softly said, so as not to startle, “Perfect, Button. A firm embrace like that makes sure your mare knows you’re there for her.”

Neither broke the embrace because of her words, which gave her much needed time to get herself better prepared for what was to come. She slid a hand beneath her skirt, her fingers at quick work to get her underwear entirely out of the way. She wanted free access to her honey pot, even if moaning would possibly ruin everything. She had to though, as she was already wet, and Button hadn’t even begun touching Silver.

Once the two finally separated, both of their faces bright red, Cheerilee whispered to Button, “Now, look to her breasts. While all mares have sensitive bosoms, us with larger sets call them our weaknesses. Be gentle at first, with pets, squeezes, and then work on her nipples. Understand?”

Button nodded, though his trembling body betrayed his nervousness to his teacher. Fortunately, as his fingertips sank slightly into Silver’s supple flesh, and she let out a squeak from the gentle rubbing she was beginning to get, Cheerilee could try to mimic Button’s hands. She knew it couldn’t be the same. Her hands knew where to go on her chest. What buttons she would want pressed. His clumsy fingers would be far more exciting as her anticipation would grow, waiting for him to find the best spots to dig into.

A gasp from Silver Spoon snapped her out of her day dreaming, and she looked up to seeing Button giving her another kiss. His hands were far more impressive, as his thumbs kneaded into and massaged the gray mare’s darker gray areolas, and the rest of his fingers hooked around the large mounds, squeezing them tight, but also shifting so as to allow the palms to grind against the sensitive flesh. Cheerilee had to dig her nails into the wood of the desk to make sure she didn’t leap up and take Silver’s place, but instead barely got out, “Th-that’s an interesting technique you have there, Button.”

Button came away from Silver’s lips as she let out a long, lewd moan, and his face was almost as red as Big Macintosh’s. “We-well, when I thought about working on her nipples, I realized that they looked like analogs sticks, and, well, tried something? Is it wrong?”

Silver’s eyes snapped open, and she looked almost like she was in a panic as she blurted out, “No!” Her hands then slammed over her mouth as her eyes went wide. “I… I mean, I-I like it.”

Cheerilee’s hands had slammed back into her lap as the two started to notice their surroundings again, and she forced herself to breathe out calmly, despite sinking the first inch of the ruler into her drenched pussy. “Well, if you think he has that down well, why d-don’t we move lower?”

Silver Spoon now matched Button’s intensity of blush, while the poor colt started to have steam rise from his head. Cheerilee swallowed hard, making sure to keep it to only the tip that was going in and out of her. “D-don’t worry. We’ll keep it to just hands, if that makes you any more comfortable. However,” she swallowed hard, her own head having issues formulating the next words, “B-Button, you need to undress as well.”

“What?”

Both of them looked at her as if she were insane, which she probably was, but she wasn’t going to admit that. At least, not now. “Seeing as this is also uncomfortable for Button, while also being deeply arousing, I will not have you leaving him pent up and in pain. Understand, Silver Spoon?”

The gray mare gripped her arm with the other, making her already pronounced chest even more on display as she looked away. She still managed to hiss out, “I suppose I should make sure Dia is getting the best,” despite the quivering of her body.

Cheerilee nodded, before glancing to Button, who looked positively robotic. She let another inch slide in, but forced herself to keep her composure as she turned back to Silver, who already had her skirt and underwear on the floor, and was stepping out of them rather unceremoniously. “Silver, why don’t you help Button get changed?”

Silver’s eyes widened even more, but with the fact that Button really did seem to be completely out of it. She even waved her hand in front of his face for a moment, but he didn’t react. She glanced back to Cheerilee, who was now at about the four inch mark, now just waiting to see just how big Button was.

With the sound of a button popping, and the colt reacting a few moments too late, Silver got the chance to simply pull his pants and boxers down in one go. Both gasped as the rock hard, throbbing cock came out, and stood at full attention. Button tried to mumble something, but it came out as pure gibberish. Silver looked slightly worried, like he might be too big, while Cheerilee went to the five inch mark. He was impressive, but he wasn’t the biggest in town, and she was admittedly unsure if that was a good or bad thing.

“S-sorry if it’s weird… or bad… or…” Button nervously scratched at his head, his eyes looking straight to the floor as his member continued to tremble in the open air. He let out a small groan as Silver ran a finger along it, and Cheerilee found it almost endearing how nervous the usually rude mare was.

She had to keep this going, especially as her wrist worked like mad to try to please the insatiable fire between her legs. She slowly pointed towards the front row of seats and squeezed out, “It’s perfectly fine, B-Button. But, for you two to be able to please each other, I suggest you sit there, and open your legs up. Th-that way, I can keep t-teaching.”

The two nodded, and Cheerilee almost began to cry as they lifted themselves onto the desks. Silver was bright red as Button put a hand on her thigh, and her hands stayed between her thighs. A glance to Cheerilee seemed to remind her of what she was supposed to be doing, and moved her hands away from the wettened folds that were on full display. Button swallowed hard enough for even Cheerilee to hear, and the teacher said, “Button, put your hand on the edge of those pink rings. As for you, S-Silver, simply place your hand on Button’s rod.”

The two nodded very slowly as their hands moved to their positions. Cheerilee sank in the sixth inch and let out the smallest of mewls as the two began without instructions. Of course, when two hormonal, young adults were as aroused as they were, instincts began to take over. She tried to instruct, tried to teach, but as Button’s finger slipped into Silver’s honeypot, and Silver began to curl her fingers around Button’s throbbing member, it simply became too much for her.

The two didn’t even notice as Cheerilee ran out, their eyes locked on one another. Each new movement and touch brought another shiver to their young bodies, and with how close they were, despite the two barely doing much of anything to the other, it wasn’t long before one of them broke.

It was Button, who shut his eyes, and cried out. It reminded him a lot of the visit from Eris, and her wet lips around his cock. This time though, he knew the wetness was from a far more private place, one that nopony had touched before, and it was with a mare he knew. And, as his cum sprayed against the floor from his release, he realized that it was a mare he knew painfully little about.

Silver’s eyes widened as he came. Not only could she not believe what had happened, or the fact that she was absolutely adoring the touch of a stupid, no class gamer, but it was also due to the two fingers within her sinking deep, and his palm pressed down upon her nethers. The smooth flesh of his hand let out a smack, especially against a small node right at the top of her pussy.

She slammed a hand over her mouth, letting out a muffled scream as she finally could not contain her arousal any longer. It was not simply a wave that she had felt at home, masturbating to thoughts of her and Dia together, but like a tsunami. Like a dam she had made a hundred times over broke, and the resulting disaster was almost painful. But it felt so good.

As the two sat there, panting, the smell of their arousal drenching the room, Silver briefly said, “Y-you should probably go.” She didn’t really want him to continue seeing her like this. It was beyond embarrassing, and it made her think confusing thoughts about the stupid idiot. Button didn’t leave though, probably because he was a stupid idiot, and instead wrapped his arms around Silver.

“Thank you. I-I know this must have taken a lot for you to do, and I swear I will try everything I can to keep my end of our deal. You mean too much to Diamond Tiara for me not to, and…” He pushed her away slightly, and mustered the best smile he could as exhaustion began sweeping through his stressed body. “And you mean a lot to me too.”

While Silver was feeling butterflies that scared the daylights out of her, Cheerilee could feel a tear roll down her face as she looked in from the doorway. She had tried just running away, just taking care of herself, but with the ruler clamped between her folds still, she knew that wouldn’t happen. She wanted too much to be in those arms of his, and her horror was almost being beaten by that desire.

She walked away from the happy couple, trying to dry her eyes as she swore never to be alone with Button again, because if she did, she would never be able to hold herself back.

Author's Note

The real magic here: None of this happened due to a wish. This happened due to Silver seeing what was to come, and the characters going on as they saw they needed to. The wish that was done was actually the one suggested: Making sure Button will have someone there for the reading of the will, which is now two days away, or chapter after the next one.

Edit: And by the comment by Ebony about getting Cheerilee into the herd, and this is one step closer to that.