Blackmailing the Teacher

by quiteTricky

Rating: mature
Tags: Cheerilee, Diamond Tiara, My Little Pony: Friendship is Magic, Dark
Length: 4416

Diamond Tiara has had enough of Cheerilee's lack of respect. Her detention was the last straw. With only a camera and a friend, Diamond Tiara is going to teach the teacher her place, and she's going to enjoy it.

I did not write this story. The original author of this story is a friend of mine, and I've gotten his permission to publish it.
Trigger Warnings: foalcon, blackmail, spanking, degradation, humiliation, domination/submission, Diamond Tiara being evil.

Everypony likes Miss Cheerilee. Her students love her, their parents trust her, she is valuable, much loved member of the community. Nopony has anything against her.

Except Diamond Tiara. She is fed up with the blatant lack of respect from the teacher. Who does she think she is? Protecting those stupid blank flanks, telling Diamond Tiara off when she catches her amusing herself. So what if she''s hurting the feelings of the other foals? It's not like they're important.

This detention is the final straw. Diamond Tiara is going to make things right. She is going to teach her 'teacher' respect.

Published 2013-12-27 02:40:07 UTC
Last updated 2013-12-27 02:40:07 UTC

Chapter One

“Miss Cheerilee?”

Cheerilee looked up, staring down at Diamond Tiara. She glanced sidelong at the clock. It was an hour past the end of the school. She looked back to her student and gave her a warm smile.

“Our time is over Diamond Tiara.” She smiled at the filly. To her surprise she wasn’t being glared or pouted at like Diamond Tiara had been doing since her detentions began last week. Cheerilee forced herself not to wince at the memory. The fit the rich filly had thrown when she was given a month of after-school detentions had earned her an additional month.

Diamond Tiara gave her an uncharacteristic smile. “Thank you Miss Cheerilee.” She went back to her desk, gathering her things, without a single backwards glare or grumbled complaint about wasted time.

Cheerilee watched her student, frowning in confusion. Perhaps the reason for all this had started to get through to her? She had despaired in the last week. The fact Diamond Tiara thought her detention was unjustified after she nearly got Scootaloo, Sweetie Belle and Applebloom seriously injured was astonishing and Cheerilee had been in such a fury at the time.

She smiled again when Diamond Tiara turned back to her, the pink filly returning the smile and trotting slowly towards the door. She was happy she was learning but...

“Diamond Tiara, wait a moment please,” Cheerilee called just as the filly reached up to open the door.

The teacher could not see, but a slightly sinister smile came to Diamond Tiara’s face. It became a slightly confused smile by the time she turned around. “Yes Miss Cheerilee?” she asked, cocking her head to the side questioningly.

For a moment Cheerilee was not sure what to say. “I was...wondering if something was wrong. Your attitude is...different.” She did not say ‘better’, although she was certainly thinking it.

“Well...” Diamond Tiara looked at the ground, scuffing the floor uncertainly with her hoof. “Can...can I tell you something? Something secret?”

Cheerilee gave a slow nod. “Of course you can sweetie,” she said, getting up and approaching Diamond Tiara. “If you want to tell me something secret, I promise it will be just between you and me. Teacher’s honor.” She added with a smile.

Diamond Tiara giggled fillyishly and nodded. “Okay, um, can you come a little closer? I don’t want to say it loudly,” she said, looking down again.

The way little fillies thought was sometimes a bit silly, since there was nopony else in the room, but Cheerilee was used to things like that and got closer, leaning down. “You can whisper it right into my ear if you want.”

“Thanks Miss Cheerilee.” Diamond TIara opened her mouth to go on but closed it a second after.

“Go on sweetie, I’m listening.”

Diamond Tiara looked away. “C-can I show you? It might be easier. Just close your eyes. Please Miss Cheerilee, it would mean so much.” She gave her teacher puppy dog eyes and a pout.

Resigning herself to the risk of a prank, Cheerilee closed her eyes. “Okay, just tell me when to open th-mmph?”

Diamond Tiara had waited until the perfect moment before she struck her blinded teacher. Her lips pressed against Cheerilee’s mid-word and she slipped her tongue in. It took a full five seconds for Cheerilee to realize that she was being kissed. One of her filly students was kissing her. Their lips were locked, larger and older, but not old, lips limply manipulated by the younger, smaller mouth. She could taste Diamond Tiara’s lips and tongue, tastes that she was too busy being overwhelmed by to think about. Her eyes popped open in shock, just as Diamond Tiara released the kiss and stepped back.

“Thanks Miss Cheerilee!” she said with a wide smile. Her teacher just blinked, dumbfounded, as the happy filly scurried off. “See you tomorrow.”

By the time she remembered to do something, Diamond Tiara was gone. Cheerilee was frozen, still in her leaning down posture. Slowly, her hoof seemed to move on its own as it approached lips. She felt them numbly, unable and unwilling to believe what just happened actually happened. Her tongue darted out, the taste of her student still on her lips.

The taste was still there, haunting the confused and worried teacher, when she numbly packed her things, promising to find out what was going on tomorrow. Tomorrow, she promised herself, she would have answers.

When she arrived at school the next day, Cheerilee did not look like her usual perfectly groomed self. Nothing was out of place enough for most of the fillies and colts to notice, fortunately. Cheerilee was relieved, but the lack of anything unusual just made her all the more worried. Diamond Tiara did nothing to reflect that she had kissed the mare teaching them sums. She was, in fact, on her best behaviour. Better, even. More than once Cheerilee spotted the ‘Cutie Mark Crusaders’ giving Diamond Tiara and Silver Spoon suspicious looks.

Her late night took its toll on Cheerilee. She had lain in her bed long into the night, her thoughts buzzing with confusion and worry. Had Diamond Tiara developed a crush on her? Was she trying to win her way into Cheerilee’s good books somehow? If she was, why this way? Did her father abuse her? Cheerilee had heard that sort of thing could lead to distorted views on how to show friendliness or affection.

Despite her occasional stutters and pauses, Cheerilee got through the day. She breathed a sigh of relief when the bell rang and her class began to file out, except of course for Diamond Tiara.

And, to her surprise, the Cutie Mark Crusaders. While Silver Spoon all but sprinted out, the three little fillies came up to her desk to ask if she was alright.

“I’m fine,” she told the girls, smiling with her usual warmth and affection. “I just had a rough night, it happens to everypony now and then. Don’t let it bother you, but thank you very much for asking. Now off you go, unless you want to stay for extra lessons.”

They gave her a small giggle, watching them all but flee the classroom. Her giggle died when she realized it was at last just her and Diamond Tiara.

“What do you want me to do today, Miss Cheerilee?” Diamond Tiara asked, looking as innocent as an angel. There was still no sign of what had happened yesterday.

Cheerilee opened her mouth, to say something about the day before, to say...something. She closed her mouth for a few seconds.

“Just...just, uh, do your homework,” she said, shaking her head and staring down at her desk.

She did not look up when Diamond Tiara replied, “Yes Miss Cheerilee.”

An hour passed, Cheerilee staring at her desk and listening to the scribble-scribble of Diamond Tiara’s pencil on paper. She knew she should say something. She had to say something. But every time she tried her courage withered up. She had no idea how this would go. It was totally out of her comfort zone and she had never been taught how to deal with this sort of thing. Cheerilee still knew she had to say something but every time she tried she never got up, or her mouth opened and closed without making a sound.

An hour passed and Cheerilee said nothing. She had homework handed in today to mark but she did not move to get it out. She just stared at her desk, her mind awash in turmoil.

“Miss Cheerilee, its been an hour.”

Diamond Tiara’s polite voice called out, at last bringing the teacher out of her trance. Taking a deep breath Cheerilee nodded. “Y-yes, y-you may go.” Her voice wavered somewhat and she didn’t bother to check the clock. She watched the little pink filly gather her things and walk out. Cheerilee gulped. One last chance, as Diamond Tiara stepped out the door, to say som-

“Ow!”

The pained cry of her student made Cheerilee jump in shock and she moving before she had time to think about it. Diamond Tiara was hunched up in the doorframe, making a whimper.

“Diamond Tiara, are you okay? What happened?” Cheerilee asked worriedly, leaning down to inspect. “I’ll get the first aid k-mmmph!”

For the second time in two days she was cut off by the childish lips pressing against her own. She gasped in shock even as she was kissed. Still, she raised a hoof to push Diamond Tiara away. She settled her front hooves on the young filly’s shoulders and made to push her away. Little pink hooves came up and for a moment Cheerilee was stopped by the unexpected resistance. But she was a grown mare, and Diamond Tiara just a filly, and she began to push her away.

Diamond Tiara pulled away instead. She smiled at her red-faced teacher. “Bye Miss Cheerilee!” She said, her voice sweet as sugar. The flabbergasted teacher had began to take deep breaths to calm herself, but at the same time she realized Diamond Tiara was getting away again. She knew once the filly was gone she would not be able to follow her, embarrassment and confusion freezing her.

“Diamond Tiara, wait just a minute! G-get back here!” Despite her shouted orders the filly took off, galloping away

Cheerilee’s hoof lifted up to her lips, and for the rest of her second, very long night, she found it wandering back as she stared at the ceiling of her bedroom.

The next day she was in an even worst state and yet again Diamond Tiara was acting completely normal! It was infuriating. Her sigh of relief was even greater than the day before and her assurance to the Crusaders that she was fine was a bit more abrupt and dismissive than the day before.

Diamond Tiara started working on her homework again and Cheerilee tried to say something again. She failed. Cheerilee stared at her desk, eyes glued to it. Ten minutes passed in silence again until an annoyed sigh broke it. Cheerilee looked up at the sound, frowning slightly.

“Is something wrong Miss Cheerilee?” Diamond Tiara asked innocently. She had definitely given an annoyed sigh but there was no sign of it.

“I...no, n-nothing is wrong,” the teacher denied, shaking her as she looked around in bewilderment.

“Oh, okay.” Diamond Tiara went back to her homework, a little smirk hidden as she looked down. “I thought you were thinking about when we kissed.”

Cheerilee froze, staring down at Diamond Tiara. “W-what?” she asked in a quivering voice.

The filly looked up and smiled widely. “When we kissed,” she repeated in the sort of slow voice used for very small children and idiots.

“W-When we....” Cheerilee swallowed nervously, licking her dry lips. This was all wrong. She had meant to initiate any discussion about it, not let Diamond Tiara do so.

“Do you need a reminder? Here, I have the picture.” There was a sinister undertone to Diamond Tiara’s voice and her words did not register with Cheerilee until the filly was digging through her saddlebag.

“P-picture?” Her voice rose in anxiety. It must be a joke. There was no way there could be a picture. Nopony else had been there, none of them had seen either kiss.

Diamond Tiara nodded, pulling something from her bag. She got up and approached Cheerilee’s desk with the same self-assured manner of a noblemare in her own mansion. Her smile only grew when she lifted the photograph.

Cheerilee’s heart felt like it stopped for a moment. There it was. There they were, Cheerilee’s eyes ran over her own features, from her closed eyes to her lips meeting the light pink of the filly she seemed to be kissing. The door frame was visible, so the picture must have been taken from within the classroom or from the window. A giggle from Diamond Tiara drew her attention off the photo and she looked with growing horror at the mocking, smug smile now twisting the rich filly’s features.

“I forgot yesterday’s picture, but you can bet it came out just as good as this one did,” Diamond Tiara said, giggling to herself nastily.

Swallowing again Cheerilee finally found her voice. “D-Diamond Tiara, t-that sort of thing is-”

“Totally inappropriate, I know.” Diamond Tiara interrupted, smirking up at her teacher. “A teacher making her youthful charge kiss her? What would the police say?” The question was filled to the brim with implications.

They were not lost on Cheerilee. Not in the slightest. The quiver in her voice grew.

“W-what do you mean?” She asked anyway, fear filling her eyes.

Diamond Tiara scoffed at her, shaking her head. “You really are stupid, aren’t you?” she said bluntly, enjoying the shock and fear in her teacher’s eyes. She smiled. It felt so nice to finally be open like this. “If the police see this picture, I think we both know what’s going to happen. Imagine if they get one of the copies of yesterday’s photo, with you holding my head in place as I try to fight you off.”

Cheerilee’s mouth dropped open. She just stared numbly down at Diamond Tiara. Yes, if the picture had been taken at the right time, it might look like that.

This was unthinkable. Impossible. She had to be dreaming, or this was a joke or...or...

One look at Diamond Tiara’s smug little expression told her quite clearly this was not a joke. She was being blackmailed.

Knowing that and accepting it made her properly calm for the first time in nearly two days. She was being blackmailed. Ever since that first kiss she had been confused and lost, but now she knew where she was and what was going on.

“What do you want? Is this about the detention?” she asked, visibly calming. “Is ending your punishment your price?”

Rather than be off put by her victim’s calmness, Diamond Tiara seemed almost gleeful at the sight of it. That more than anything worried Cheerilee.

“This stupid detention was the last straw, but its about a lot more than that ‘Miss’ Cheerilee. Those stupid blank flanks have been your favorites and you keep protecting them, for one thing. That’s going to change.” Diamond Tiara announced.

Sweat broke out on Cheerilee’s forehead. Maybe this was not going to be so simple and straightforward after all.

“What do you want Diamon-”

“Shut up.”

The sheer audacity of her student actually saying that to her shocked Cheerilee into silence.

“Good. That’s the first thing; from now on, you call me ‘Miss Tiara’ at all times.” Diamond Tiara said it as though her command being obeyed was the obvious path. “And from now on, you do whatever I say or I’ll make sure copies of the photos, copies I have hidden where you could never find them, make their way to the police, who will throw you in jail. Imagine it, everypony in town talking about how you’re a paedophile, guessing at the other abuses you’ve committed. All that love and acceptance, turning to hate and disgust.”

As her student described what would happen, Cheerilee began to shake. Diamond Tiara was serious. She was deadly serious and Cheerilee had no idea how to get out of this.

“P-please, Diamond Tiara, let’s talk-” She tried to negotiate, to reason with the filly only to be interrupted.

“That’s ‘Miss Tiara’ to you!” Diamond Tiara snarled, glaring her teacher into silence. “One more mistake like that and you’re in for punishment of your own.”

Swallowing her fear, and her pride, Cheerilee took a deep breath and tried again. “M-Miss Tiara, I’m sure w-we can talk about this. Y-you don’t understand what you’re doing.” She flushed with humiliation. It was obvious why Diamond TIara had picked that way of being addressed, even the verbal emphasis had been identical to how her students said ‘Miss Cheerilee’.

Diamond Tiara snorted and shook her head. “I knew you were an idiot. No, ‘Cherry’, I understand what I’m doing perfectly. I’m blackmailing you into being my slave, and if you don’t agree to do whatever I say until I release you I’m going to get you thrown in jail and reviled by every pony you know and love for being a disgusting kiddie-fiddler. Or did I miss something?” She asked nastily.

Cheerilee stayed quiet.

“Answer me.” Diamond Tiara’s voice became hard and harsh.

Cheerilee took a deep breath.

“N-no Miss Tiara, you didn’t m-miss anything.”

Diamond Tiara smirked, not even bothering to hide her smug sense of victory. “Good girl. Go lock the door.” She ordered, turning and heading to the window. She glanced back at the stationary mare. “Unless you’d rather go to prison.”

Cheerilee hurried over, locking the door and pulling the blinds down over the glass panel. When she turned around, her student had done that for all except a few of the higher windows. “It’s done.”

“I can see that, stupid.” The filly sneered. “And that’s ‘Miss Tiara’. That’s one strike. Two left, Cherry.”

Pale under her fur as she considered what would happen if she got three strikes, Cheerilee nodded. “Yes Miss Tiara.”

Smirking, Diamond Tiara giggled at the fearful look on her teacher’s face. “At least you can learn. So you’re not a complete idiot. Let’s see if you can earn the loss of that strike. What do you think I’m going to have you do now?”

“Cancel your detention, Miss Tiara?” Cheerilee thought it was a good guess, but the filly just laughed.

“Okay, I guess you are stupid. Of course not, if I do that I won’t have an excuse for us to be alone together. No, your first order is not to punish anypony else with detentions,” Diamond Tiara instructed as she began to rifle through other ponies’ desks. “This is our time together. You’re not going to keep anypony after class either. If you do, every minute we lose I’ll punish you for.”

From the sound of it, Diamond Tiara wasn’t intending to let this go. Cheerilee bit her lip, fighting down her automatic reaction to tell her off for invading the privacy of the other children. She was sweating nervously, unable to stop this situation as it spiraled out of control. What was she supposed to do?

“I didn’t hear a ‘yes Miss Tiara.’”

“S-sorry Miss Tiara.” Cheerilee swallowed. “Yes Miss Tiara, I won’t give out any detentions.” She agreed.

“Good.” It was in Scootaloo’s desk the filly found what she needed. A wooden ping-pong bat, a flat circle with a short grip. “Perfect, I knew the blank flanks tried ping-pong yesterday.” Taking the bat in the mouth, Diamond Tiara hurried towards her teacher with a smirk visible around the grip in her teeth.

Somehow, Cheerilee doubted she wanted to play a game of ping-pong. “W-what’s that for? Miss Tiara.” She added quickly.

“Hmph, I’ll let you off this once.” The filly sneered. “Get over your desk, flank in front of me. This is detention after all, somepony does need to be punished.”

It didn’t take much for Cheerilee to realize what she was going to do, and it made her gulp. She began to comply, but it apparently was not fast enough and she got a solid smack on the flank from the bat.

“Faster!”

“Y-yes Miss Tiara.”

It didn’t really hurt, just sting a little, but what the hit represented made her comply. She put her front on the desk, her flank and rear hooves sticking off.

“Eyes front, Cherry.” A chair scraped along the floor as Diamond Tiara pulled it over. When it stopped, Cheerilee had to fight not to look back and check. She stared at the black board, trying to think of a way out of this.

Her thoughts were cut off by a sharp wooden smack on her flank. Diamond Tiara was a little filly but she was still an earth pony and the hit stung. Cheerilee let out a yelp at the surprise hit, and started to look around.

Smack!

“Eyes front!”

She stopped turning, keeping her eyes on the blackboard. “Y-yes Miss Tiara.”

Smack! “Good girl.”

Cheerilee bit her lip, letting out a whimper as the surprisingly painful spanking continued. She felt tears in her eyes, a flush of embarrassment rising to her cheeks, wincing as another blow landed on her increasingly sore behind. Her tail held up and out of the way, the teacher whimpered as her student spanked her. She had never been so humiliated, but what could she do? Her entire life would fall apart, everypony she loved would hate her for being a paedophile. Each hit sent a little spike of pain through her, worsening with every blow.

Smirking, Diamond Tiara felt an intense rush each time the loud slap of ping-pong paddle on plot filled the classroom. Cheerilee, her ignorant, disrespectful teacher, was just taking it, letting her tan her flank red. She could see it under Cheerliee’s fur, a steadying reddening as the filly took care to make sure she had every inch of her teacher’s rear nice and sore. A sense of power filled Diamond Tiara at the sound of her teacher’s whimpering. She was in charge now, which is just how things should be.

Lowering the paddle at last, Diamond Tiara giggled.

“So, do you know why you needed that spanking?” she asked casually.

After a few seconds recovering from the pain of the spanking, Cheerliee tried to answer. “B-because-

Smack!

“Bad girl!” Diamond Tiara barked. “Raise your hoof when you want to answer a question!”

Lifting her hoof with a whimper, Cheerilee stared forward as she tried to ignore the throbbing pain in her backside.

“Yes, Cherry,” Diamond Tiara said in a sweet imitation of a teacher picking a pupil.

“B-because, Miss Tiara, somepony needs to be punished in d-detention?” Cheerilee said shakily. She held her breath, waiting for another spank.

Diamond Tiara giggled, nodding. “Good girl. I guess even idiots can learn. So, tell me Cherry, do you know what that means is going to happen in every detention you have with me?”

Cheerilee gulped, stiffening as the realisation. That was enough of an answer for Diamond Tiara, who laughed again.

“That’s right! Here’s what is going to happen from now on; every day, after the bell rings and it’s just you and me, you are going to take out an afternoon snack and bring it to me. While I eat, you are going to do my homework and mark it all as A plus. After that, you will pull down the blinds, get back into this position and stay like that until I give you your punishment. How does that sound, Cherry?” Diamond Tiara asked, not even trying to hold back her gloating, smug smirk.

Sniffling weakly, Cheerilee took a moment to answer. She quickly replied, when she felt the paddle lightly tapping her sore rear in warning.

“It...it sounds g-good, Miss Tiara,” she answered, her gaze on the blackboard in front of her, trying not to think about what was happening to her.

“I’m glad you agree. Now get down!” The command was punctuated by the stinging smack of the paddle, jolting Cheerilee to attention. She yelped, getting off her desk and standing before Diamond Tiara, quivering fearfully.

“Y-yes Miss Tiara,” she mumbled, looking down on the filly blackmailing her.

Tiara sneered, “You look pathetic, did you know that? Sniffling and whimpering, honestly, don’t you have any dignity? That was a rhetorical question, dummy.”

Cheerilee lowered the hoof she had raised, blushing in embarrassed. She was just trying not to get caught out.

“Of course you don’t. You don’t have any brains either, or you wouldn’t be in this position,” Diamond Tiara continued. She pointed at one of the closed blinds. “Go open those blinds, but just those ones, and then come back.”

Fearful and obedient, Cheerilee hurried over. Her ass burned with each step. Although Diamond Tiara was just a filly, she had been quite thorough and enough spanks had left the mare’s butt cheeks reddened and sore.

“Good girl. Now, sit down,” Diamond Tiara instructed her when she was back, grinning at the squeak of pain that erupted from her teacher as her butt came into contact with the floor. The filly stepped up, manually rearranging Cheerilee’s posture and hooves.

“Be quiet Cherry. There. Now, we’re going to kiss again. Wrap your back legs around me, hold my head close and kiss me,” Diamond Tiara instructed. “Keep kissing me for thirty seconds, no matter what I do, and you better do your best to look and act eager. If you don’t, or you cut it short, I’m going to spank you again.”

Regardless of what the snobby filly might say, Cheerilee was not an idiot. She could tell exactly what this was. Whoever had taken the pictures, she guessed it was Silver Spoon, was going to be taking more. As much as the idea of kissing - making out, in fact - with a filly of Diamond Tiara’s age revolted her, the fact was that she knew she couldn’t say no. She hesitated for a moment, but an impatient growl from her blackmailer ended it.

Drawing Diamond Tiara in, Cheerilee tightened her back legs, her forehooves pulling the filly’s head in and pressing their lips together. She did her best to act like she was enjoying, like she wanted it as she slipped her tongue into Tiara’s mouth. The filly began to push and smack at her. If anyone saw this, it was clear all they would see would be Cheerilee forcing her student to kiss her despite the obvious resistance. Diamond Tiara, it appeared, was trying and failing to fight her off, held in an unwilling embrace. Somewhere in the distance, a camera was recording this, snapping shots of her shameful activities. It was even more ‘evidence’, amassing more and more blackmail.

Cheerilee was smart enough to work this out, and it nearly made her cry. She was digging herself deeper, knowing that if she stopped or hesitated she would be trapped there forever, buried. Her only hope was to keep digging, and hope she could find a way out.

Diamond Tiara was smart enough to work this out, and it nearly made her laugh. She had no intention of giving her new pet up, ever. The filly enjoyed the kiss, her tongue pushing into Cheerilee’s mouth as teacher and student made out.

* Fin Chapter 1 *