“Look, you can tell them that if they don’t want to end up fucked over when the merger happens, they’ll take a few more minutes with their heads out of their asses and actually think before I come there myself and rip them apart myself. Now, if you have to call me again before tomorrow, consider yourself fired!” Diamond Tiara slammed her phone shut and sighed. It had been a long week for her with the company takeover that was happening, but she had promised herself tonight. A day to be with an old… acquaintance. It’s better than being alone, I suppose.

Still, she did think it was odd for her old teacher to call her. Cheerilee had always seemed to dislike her, or at least think poorly of how she acted, so to call her on Hearts and Hooves Day was the last thing she had expected. “Come on Dia, you know better than to think such things. She probably just wants to catch up.”

Opening the room though, she felt a small tightness in her chest and loins as she saw her old teacher in what could only be considered as lingerie. A small wrap around her breasts, and a loincloth was all that covered her titillating body. Diamond swallowed hard before turning around on a dime. “I’m sorry, wrong room.”

“No, it’s not Diamond. Just like it wasn’t for that one time you got detention in sixth grade. Your embarrassment was cute then too.”

Diamond felt her face flush at the memory of her first detention and stepped forward, clenching the door frame. “I’m sorry, but what have you done with Cheerilee, as such a person who looks like yourself cannot be her.”

Cheerilee raised an eyebrow as she shifted her leg to the side. Her spot on the table gave Diamond a clear view of her cootch, and Cheerilee smiled as the pink mare turned away. “Do you remember chemistry and teaching safety? Specifically after the incident where Boom talked about chemical mixes.”

The pink mare bit into her cheek. Cheerilee had had to listen to almost fifty different ‘fun’ ways to cause a small accident. The day after, just to make sure they all were safe, she had herself lit on fire, with a magical barrier provided by Twilight being all that protected her. None of them knew about the barrier though. To say the least, it had the desired impact. Just like this might if she’s being weird and preachy.

Stepping back into the room, Diamond crossed her arms and finally stared at Cheerilee, though only at her eyes instead of…Don’t even think about it Dia. “Okay Cheerilee. I came here with the apparently idiotic hope that you wanted to connect with me and put the past behind us. If you’re just here to bitch at me though, I’m not having it. Not now.”

Cheerilee shook her head as she stood up. “I’m simply reminding you of a basic lesson.”

“What? How to make my father have a heart attack?”

Cheerilee shook her head. “When was the last time you calmed down? Just, sat down and didn’t have to think about anything?”

“I spent lunch with Silver a week ago.”

“And how did you possibly want that lunch to finish?”

Diamond tried to keep her fire down, but no matter how stoic she kept her face, the reddening of her cheeks gave her away. Cheerilee stepped closer and put a hand against Diamond’s face. “Did you really want it with her though, or simply because you were repressed? Needed some… relief?”

A quick shake of her head switched the arousal back to the stoked fire that was normally within her. “I don’t even know why you would think I think about such things. I don’t have the time for relationships or anything so basic as carnal desires.” She caught her breath as Cheerilee took a long stride and was now dangerously close to rubbing against her body. One small touch on the front of her short, tight skirt got Diamond to look down and her mouth dried up. “Wha-what are you–”

Cheerilee kept one finger on Diamond’s lips. “Just getting your attention. Unlike others, you need to continue to think. Think about whether or not you want to lose the greatest years of your life to anger, work, and,” tapping the skirt again, “fear.”

Diamond backpedaled fast, but soon found herself tripping over a desk and crashing to the ground. Cheerilee leaned over her and held a hand out to her. Diamond watched as her teacher’s barely restrained breasts swung in front of her face. She licked her lips as a small bit of pink showed itself, but then turned away. “No.”

Cheerilee got onto her knees and put a hand on her student’s leg. “If I was going to judge you, would I be dressed like this? Like a young, teenage hooker? I dressed like this to remind you that you need to have a side, well, maybe not quite like this, but one without that pole up your rump. Now please, at least talk to me.”

Diamond shook her head. “No. Just… just go. I have work I should get back to.”

“Look me in the eyes and say that.”

She looked up and stared into Cheerilee’s green eyes. They didn’t waver, they didn’t shake, they merely continued to watch. Continued to care. Just as always. Diamond rubbed at her eyes. “You don’t get it. I’m supposed to be perfect, and all I am is a freak.”

Cheerilee nuzzled against Diamond’s cheek. “Have you ever even shown it to another pony outside of your family? Had someone see it and scream?”

Diamond opened her mouth, but then closed it. She had no answer, and she laid back with a sigh. “I… I’m not sure if I want you to look at it though.”

Cheerilee started to rub the slight bulge she could see with her palm. “Hoping to save it for the one you like? Because if so, I would love to hear when you planned to do so.”

The sarcasm stung just as much as it always had, and a tear ran down her face as soft, white fur crossed into her mind. Fur she would never have beneath her throbbing– “Gah!” She looked down, only to see that Cheerilee’s hand had disappeared beneath Diamond’s skirt. “What are you, nng, doing?”

“I know you, just as I know my other students. Without a push, you won’t get anything done. Not with this.”

Diamond Tiara swallowed hard as she felt Cheerilee’s hand gently run along her member. Each inch that she caressed sent shivers of repressed arousal shooting through Diamond. It was the first time another pony had touched her this way, and already she was adoring it

Cheerilee noticed the tears coming down her student’s face and frowned before she leaned forward. With the large meatstick still firmly in her right hand, she gently kissed one of the drops away from Diamond’s cheeks. “Please, forget about her tonight. You’ll hate all of this in the morning and be at square one if you can’t enjoy yourself, so please, try. For me.”

Diamond looked back into those radiant eyes that were over her and took a deep breath in as the first drop of precum escaped her tip. “Ye-yes, Cheer–” Her teacher’s finger cut her off, and she simply nodded. She knew Cheerilee was right, and no matter how disgusting it was, she was finally willing to learn how to use her curse.

Cheerilee laid Diamond down onto the ground before pecking her cheek. The draft in the room caused her pert nipples to rub through the thin wrap on her chest, and she let them grind against Diamond’s fluffier body as she made her way down. With each button her mouth met, she flicked her tongue around it and popped the plastic circle loose, allowing Diamond’s own large, perky breasts to peak out. Just as Cheerilee rested her head on the mare’s waist, she reached up and pushed one hand underneath the lacy pink bra, squeezing the mound underneath. “This needs to come off.”

Diamond Tiara bit into her cheek as shivers ran down her spine. “I… I think I’m good. Revealing… it, is going to be hard enough as it is. I don’t need to show off everything.”

Cheerilee smiled slightly as she started to rub the mound. As her hand stretched the bra, the other mound moved in time with her hand, being forced to and fro just like its twin. “You know, I can see why you want it like this. Your excuse was cute though.”

The friction between her nipple and the stressed fabric continued to send shivers down her body and she felt herself starting to heat up. Cheerilee’s hand was merciless as it took full advantage of her mistake. Her nipple was firmly clenched in between two of her teacher’s fingers and was pulled being firmly pulled and pushed, with each motion stretching, tearing, and grinding the fabric against her. All while a loose grip was kept around her shaking and quivering shaft. “Chee-Cheerr, I… I’m not going to be able to take much more.”

Cheerilee simply smiled as her right hand started to move again. Slowly, the tender fingers ran along the throbbing mass that was hidden beneath the skirt. With each pump, more precum escaped the tip, precum Cheerilee pressed against her palm, before sliding her digits back along her length so as to wet the shaft. The wet smacking sound of the the hand against Diamond was only beat by the young mare’s sweet moans as her pleasure grew by the second.

Diamond Tiara tried. She didn’t want to cum, not when she was still in her suit, not while she was in front of Cheerilee. It felt so good though as the fingers rubbed her down, and that naughty palm that constantly was driving her insane almost brought her to tears. One more glance down at Cheerilee’s lust filled eyes was the final push. Those eyes that demanded her cum.

Diamond’s cock throbbed and pulsed as finally all that had been pent up got to burst free. Thick ropes of cum shot out from the large member, each coating more and more of her skirt. Cheerilee hummed to herself as she slowly pumped the last bits of cum from her student before pulling her drenched hand out from beneath the soiled fabric. She ran her tongue along her hand, her eyes dead on Diamond’s. “Give me your skirt.”

Diamond’s mind was numb as she hooked her fingers into her underwear and skirt’s hems and handed the brown fabric to Cheerilee, who brought it to her face and sniffed into it. The teacher’s rump came high into the air as she rubbed her face and the skirt onto the ground, humming to herself to emphasize just how much she adored the smell. She tucked some of the soaked threads into her mouth and moaned as she tasted the cum through it, shaking her hips.

Diamond sat speechless as she got to watch the person who had made her school days a hassle at times, act as if she were a cock addicted whore. How fi… No. She’s just doing this for me... right? Diamond shrugged off the second option, as the idea that her teacher would degrade herself like this for her sake brought a tear to her eye. The sentiment quickly passed though as Cheerilee’s tail flicked to the side.

Cheerilee heard the exclamation and smiled to herself as she lowered one hand to her exposed crotch. Her tail flicked to the side, moving the short skirt she wore out of the way so Diamond could get a real look at her hot, dripping arousal. Two fingers came around her crotch and started to slowly, deeply, stroke into it. After a few moments of simply enjoying the site, Diamond realized just what she was doing. She was signalling for her to come there.

Cheerilee’s scent filled Diamond’s nose as she crawled on the ground and came within centimeters of Cheerilee’s pussy. The smell caused her to shiver, and the lick she gave the trembling folds did taste sweet. It wasn’t what she wanted though. She had never been the type to simply please others, and she didn’t plan to make this the first time she did so.

The older mare jumped slightly as she felt Diamond rubbing her rear with her cock. With each moment, the cock grew stiffer as it slid between the nice, tight rump. For a few moments, Diamond bit into her lip as she considered plugging that small, puckered hole she kept glimpsing, but quickly decided against it. She would be a real stallion tonight, no matter how stupid that meant she was.

Shudders ran through both of them as the hard prick touched Cheerilee’s entrance. For a second, Diamond thought about not doing it. She was already coming to accept the curse between her legs, so maybe she could wait for the one she wanted. Wait for her sweet Sweetie– “Gah!”

Cheerilee had decided her student needed another push and Diamond found herself half within her teacher because the older mare had pushed herself up. Her resolve now steeled and the pleasure already almost getting her to cum as the hot folds surrounded her, Diamond pushed her teacher back down, hilting the heated mare.

Cheerilee found her tits grinding against not only tight fabric that only truly covered her nipples, but also the floor, and it got rivers to start running down her legs as each thrust filled her. Diamond on the other hand, was not dealing with it so well, wanting this to last, just like Cheerilee, but feeling like she was about to burst, just like her tits from the constraints of her bra. Each thrust brought her to the brink, and tears started coming to her eyes, wishing she could do better. Not be the only one pleased tonight.

“D-don’t worry, I’m right there too Dia.”

Diamond’s eyes flew open as Sweetie Belle’s voice filled her ears and she found herself unable to control herself. She slammed forward one last time and both mares let out loud screams. Sweetie’s body shook as thick, hot semen filled her and started to surge out. Each smaller thrust from Diamond forced more in, and both her legs and Sweetie’s thighs ended up covered in her white gift.

Sweetie slowly crawled off the thick member that slightly throbbed as her folds tugged on it, before she weakly pushed herself over. She smiled at the mare she loved and held her arms open, her voluptuous chest now fully exposed. Diamond didn’t hesitate before she dove into the inviting bosom. The two shared one, long kiss before they collapsed, happy to be in one another’s arms.

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Author's Note

Apologies for how long this took to come out. It has actually been done for a while, but do to problems with my editor and me being busy, it ended up slipping under the radar to actually get published. We only have two more chapters left though, and I hope you enjoyed this one!