After-School Special

by Cypriot

Rating: mature
Tags: Cheerilee, Applejack, My Little Pony: Friendship is Magic, Romance, Original Character, Sex
Length: 3711

Cheerilee loves helping out a pony however she can. This day would be no different, except... she's in over her head. Maybe somepony can help her.

Cheerilee loves helping out a pony however she can. This day would be no different, except... she's in over her head. Maybe somepony can help her.

Published 2013-02-23 18:10:01 UTC
Last updated 2013-02-23 18:10:01 UTC

After-School Special

I love that look of discovery on my students’ faces, when something’s really sunk in, and I know everything’s changed for her, forever. I love it.

After gazing at the stick-figure watercolours hung up on the bulletin board to dry, I lean my broom back in the corner. All my pencils are neatly in their cup. All the desks are straight in their rows. Before I even started tidying up, I’d closed the shutters on the schoolhouse windows, and the low sun is making blinding little beads of light through the slats now.

I walk over to the blackboard, grab the pair of erasers, and clap them together hard. I turn away, but it never fails – I can feel that familiar tingle in my nose again. My little high-pitched sneeze rings out in the room’s stillness. Sure, I could avoid that if I wanted to, but… I guess it’s my little ritual – I like the smell of chalk.

For a minute, I gaze out the door – the one window left unblocked – then take my seat behind my desk and start on the pile of quizzes that need to be graded. Almost there. Maybe I’ll get dinner at a decent hour tonight.

I don’t know how much time has passed. The sun’s sunk enough that it’s behind the trees now, so I jump a bit when I hear a knock at the door. At this angle, I can’t see who it is. ‘Yes? Come in!’

The knob turns slowly, then the door swings in, creaking on its old hinges. Whoever it is stands in the doorway and breathes as if to say something. I can hear hooves shuffling on the doorstep. A scared student? A concerned parent? ‘Yes?’ I repeat.

Finally, an earth pony stallion enters and shuts the door quietly behind him. ‘H-hi, Miss Cheerilee,’ he says, rubbing a hoof down his neck as he stares at the floor. Something looks familiar about him.

‘Can I help you?’ Definitely not a student. But he doesn’t look old enough to be a parent, either. Maybe he’s here for…

‘I was a student of yours several years back. Ledger. Ledger deMane.’ At least he’s looking up a bit now, but he still won’t meet my eyes.

‘Ah, yes. I remember you. Quite the number cruncher, as I recall.’ A bit of small talk never hurts. He’s nervous enough as it is.

‘Yeah.’ A blush overtakes his cheeks as he giggles. ‘I just graduated from accounting school, and I’m going off to work for my uncle’s brokerage in Manehatten. I leave in two days.’

‘I see.’ I keep quiet, letting him work through what he has to say. I can practically see his heart thumping in his chest, and is that a bit of sweat on his forehead? Oh, I’m being awful to him now! My smile is about as far up as he’s willing to look, but it’s had the desired effect – his shoulders relax. ‘What brings you here?’

‘Well, I’ve never really had a fillyfriend’ – pity, he’s not bad-looking – ‘and some of the guys told me…’ He gulps.

‘And they put you up to this?’ I raise an eyebrow and watch him stammer. One more test to grade.

‘N-no,’ he finally spits out. ‘I just wanted to make sure I knew… the right way… to treat…’

I tap a hoof on his nose. ‘Right answer.’ Looking back at his goofy grin, I step back to my desk and flop into the chair. ‘Over here,’ I say, beckoning to him to follow. While I hear those few tentative hoofbeats approach on the worn floorboards, I lean down and rummage through my bottom desk drawer. ‘I know they’re in here somewhere – aha!’ I pull out a pair of rolled-up thigh-high stockings and slide each one on slowly. As his breath catches in his throat, he gulps even harder than before.

I get back up, shove the stack of papers out of the way, slide in between Ledger and the desk, then ease myself back onto its smooth surface. ‘Alright, then. Let’s see what you’ve got.’ For a minute, he just stares down between my legs and doesn’t say anything. ‘What? It’s not like you’ve never seen one before. All us mares walk around naked, after all.’

‘Yeah, but not like…’ He nods quickly, sucks in a breath, and runs his tongue over my snatch. Then a second time. Mmmm. I let my head drop to the desktop and close my eyes lightly. A few more licks, and I can feel that warm sensation spreading up and through my body. Gotta keep my mind focused. He’s a first-timer, after all. It’s not like anything spectacular is going to happen.

I let a low moan escape my mouth and sway my hips a bit. He responds by flicking his tongue faster and pressing his muzzle in harder. Good instincts, Ledger. Follow my lead.

Little by little, a wet trickle is running down over my bum and onto the desk, and I hear him slurping. I can’t help but smile. After all, it’s kind of a source of pride. I can never be sure what anypony might like – what one finds appetising, another might find disgusting – so I regulate my diet carefully to keep the taste neutr—

Nnnnnnnggggg! Ahhh. He’s found the right spot, and my back arches almost on its own. No way he misses that signal. No, he finds my clit again immediately and works his lips over it as I reach down with my forelegs, run them through his mane, and pull his face against me harder. His hot breath spilling from his nostrils, he slips his tongue inside and wriggles it around while the mix of spit and juice runs down his chin. I squeeze my eyes shut harder, sway my hips around faster, but then… he’s stopped. I open my eyes, and he’s finally looking me in the face.

Through his heavy panting, his eyes are screaming the question he can’t ask as he fiddles with his cock. I nod.

He’s on me in an instant, lurching forward and putting his forehooves on the desk. He drives forward a few times, but finally notices my raised eyebrow and half-smile. Try again, Ledger. Things don’t generally line up on their own.

Reaching a hoof down, he guides his cock in, slowly at first, but once it’s slicked up, he buries his full length. I take his hips in my forehooves. ‘Alright, what I want you to do now is—’

He starts pounding relentlessly.

‘Ledger. Ledger, stop,’ I say quietly but firmly, leveling my stare at him. Too late. I can feel him pulsing inside me. Just four thrusts in, and he’s already shot his load.

When he finally manages to stop his shuddering breath, close his mouth, and open his eyes, his gaze jerks down to meet mine, his cheeks bright red and his brow creased. ‘I-I’m… sorry…’

I close my eyes and take a steadying breath. Time to regroup.

‘Shh,’ I say, putting a hoof over his lips as his ears droop. He tries to back away, but I wrap my hind legs around him and draw him back to me. ‘It’s okay. This is your lesson. Stay in. We’ll give it another try in a minute.’ He squints a bit. That’s alright. He’ll understand soon enough. I pull him down onto me and feel his heart thudding against my chest, his cheek against mine.

‘You’re doing fine,’ I whisper into his ear. ‘Give it time.’ My breath must be tickling his ear – it flicks once or twice as I’m speaking. I take it in my mouth and nibble along its soft edge. We stay coupled like that for a good ten or fifteen minutes before I hear his breathing pick back up a little.

Up for round two? I run a hoof up and down his spine, and soon feel him stiffening and swelling inside me again. Yeah. He sure is.

As he draws back and props up on his forehooves, I relax my hind legs to let him. But I keep a hoof against his cheek. ‘Slow.’ He purses his lips and nods.

Back and forth, side to side, I roll my hips at a nice, easy pace as he moves with me, always slow, always controlled. A couple of times, he pulls back too far and pops out, but that’s okay – just something else he needs to learn. Each time, back in, and back at it.

Nice and slow. Mmmm.

I let myself sink into the desktop and breathe along with the rhythm. Once in a while, I catch him trying to speed up, but I apply a little gentle pressure to his shoulder, and he eases up again. He’s got the hang of it. A nice, steady rhythm. Steady. I could close my eyes and forget about the room around me. I’m not bored, just… enjoying myself. Yeah. This is about him, not—

Oooooooh. Mmmmm, he’s found a nipple and is flicking his hoof over it. There’s an – nnnnngg – electric warmth radiating, all over my body, and I let myself writhe around a little faster. Good, Ledger. Mmmm. Still, every few breaths I exhale, I hiss ‘slow’ at him, and he’s listening. He’s got his eyes clenched shut and his mouth hanging open, but each time I say it, I take a peek, and he nods.

It’s dark out now, and I’m definitely going to have a late dinner. Celestia, why am I thinking about that?

I raise my head a bit and look down at his cock sliding in and out… Mmmm. That tingle is back. Just gotta keep my head on straight. Just…

His legs are starting to shake. He’s not going to last much longer. Oh, well. No luck for me. But that’s okay.

Whimpering, he swallows against the dryness in his mouth and looks down at me, his eyes searching for something. Almost there. I nod back.

Ledger keeps the same pace, but shoves forward harder each time now. Harder… harder. His legs are shuddering, his mouth hanging open again, and I grab the edge of the desk to keep myself from sliding back, moaning louder and louder, then finally… he cries out, and I can smell that sharp scent again. He gasps for air, then staggers back a few steps and struggles to stay on his hooves.

A goofy grin on his face, he stands there trembling for a minute until I roll off the desk and walk up to him. ‘You’re going to make somepony a good lover,’ I say, nuzzling his neck. ‘Maybe you should go on home to dinner, though. It’s getting late.’

‘Y-yes’m,’ he stammers, stumbling toward the door. ‘Th-thank you for…’

I love that look of discovery on my student’s face, when something’s really sunk in, and I know everything’s changed for him, forever. I love it.

For a moment, he can’t decide what to do, so I give him a warm smile and hold the door open for him. I hate to seem like I’m rushing him on his way, but there’s really nothing left to do or say.

Back to work. I wipe up the floor, my desk, and myself, then fall back into my chair and take off the stockings, draping them over the open drawer’s edge. Sighing, I slide the next paper off the stack and find my red pencil.

Right, right, wrong, right, right, right, wrong…

Next paper. Next.

How long have I been at this? The stack’s pretty short now, and I might still get some time to read after dinner, before I go to bed.

There’s another knock at the door. I rise to answer it, but Applejack’s already poked her head in.

‘Oh! You are still here. I thought somepony mighta left the light on.’ She nods and tips her hat.

‘No, just working late. Can I help you with something?’ I smile at her. Probably too big. Can she tell? Get a hold of yourself, Cheerilee. She’s just a concerned parent or… Well, yeah, parent. Same thing. But it’s Applejack.

‘Well,’ she says, stepping in and closing the door behind her. ‘Y’see, it’s just… It’s been so long since – I hate to admit that, but I was wonderin’ if you could…’ With a forced smile, she takes off her hat and holds it to her chest.

Twice in one day? I don’t know, but… it’s Applejack.

My smile turns weak as she walks over to my desk. Can she see my eyes wandering? I feel like a foal on Hearth’s Warming Day.

I walk around her, fighting to keep my voice steady. ‘Let’s see what we have, then,’ I say, constructing a playful smirk. Her tail is clamped down hard. I scoop under it with my nose, but she snaps it back down again.

‘Uh… Ain’t you gettin’ a bit personal there?’ she asks, her eyes shooting wide open.

‘Relax. I know what I’m doing.’ I lift her tail again to have a look, and… she’s already hanging wide open. Poor thing came over here already worked up. There’s a trickle of moisture most of the way down her leg, and I give it a sniff.

Apples. Figures. Like I said, I keep my own taste neutral as best I can, so nopony can say they don’t like it. But I love apples.

I start my tongue down where the drip is near her knee and work my way higher, until I’m licking up what sweet, tart juice has already gathered on her glistening lips. Her hat drops to the floor.

‘Nnnnnnh!’ she says as I flick the tip of my tongue over her clit. She braces herself against my desk when I shove my muzzle against her, and she’s not fighting me with her tail anymore. I plunge my tongue in, scooping out all the apple taste I can. In and out, faster, faster… Reaching up to her belly, I search out a nipple and stroke a hoof along it, making her gasp. Seconds later, she arches her back, lets out a long moan, and a muscle spasm is squeezing my tongue.

Already? Wow, I… Well, there’s a warm, wet patch growing between my own legs as well. I mean – it’s Applejack.

She clenches her muscles and shudders two or three more times – I’ve lost count, and I really don’t know how long it’s been, either. I don’t care. I’m just licking and grinning like an idiot because oh, Celestia it’s her and she keeps groaning and… and I can’t take it anymore. I climb onto the desk, roll on my back, and put my twat right in her face. ‘Let’s see what you can do,’ I say, breathless.

Tentative at first, she prods with the tip of her tongue, but then licks slowly with its full breadth, over and over. I can’t even hold my legs up anymore. They’re just hanging limply off the desk, and everything leaves my mind except that warm breath across my stomach, the lingering flavor of apples in my mouth, and that lapping that’s making – almost there… Nnnnnnngggggg. I catch my breath just in time for… Hnnnnnnn. I sigh loudly and roll my eyes back in my head.

Is this really her first…? No, she only said it’d been a long time. Still… None of these ‘students’ have ever made me come before. Well, to be fair, Applejack’s done that plenty of times when I was alone in the bathtub at home, but… this is the real article!

When my eyes come back into focus, I see that Applejack’s taking a breather. I give myself a good minute for my own panting to subside, then I lean forward and tug her on top of me, her warm coat against me and her heartbeat thudding into my chest. Reaching around her hind leg, I run the edge of a hoof through the smooth moisture. She’s breathing heavily, her mouth hanging open, and I wrap my other hoof around the back of her head, turning her muzzle toward me so I can clean my own juices off it. My tongue runs all around it, catching the edge of her mouth a couple of times. I-I’d love to, b-but I can’t… Those soft lips are so inviting, but I never, ever kiss during one of my lessons.

I kiss her hard.

I kiss her hard, and she slides her tongue into my open mouth. My hoof under her tail is flicking as fast as my fractured concentration can manage, and soon her breath comes in spurts as she moans down my throat. Little by little, I feel her hoof tracing its way down my side toward my nipples, and I grimace, bracing myself for the rough, chipped edge I’d expect of a farmer, but… it’s like silk caressing me. I lose myself in that mare rocking back and forth on me, and soon we’re both trembling at the same time. She pulls her mouth away to squeeze her eyes shut and groan and I echo her and I can feel myself building again – almost there—

But she slides off me and plops down on her haunches, her body spent. After my chest heaves a few more times, I make a snap decision and reach down to finish myself off with my hoof while she watches.

I just lie there for what feels like an hour, our panting filling the room. Our. Us. We. I… I like the sound of that. I…

‘Whoa, nelly!’ she cries, and I can’t help but laugh. It’s Applejack. It’s really her. But…

I knew what this was when it started. This is a one-time thing. An arrangement of need. There’s no reason to think that anything lasting will come of it. My face falls. ‘Thank you kindly, Miss Cheerilee, but as I was sayin’ –’ she takes a moment to catch her breath again ‘– it’s been a long time, and I hate to admit it, but… I don’t remember my algebra so well. Apple Bloom’s gettin’ ahead in math, and I’d like to borrow a textbook for her, if you don’t mind.’

I stare at her as my self-delusion shatters around me. I was almost there…

Thanks to my colour, it’s hard to tell when I’m blushing, but the fact that I’m huddled on the floor against my desk with my face buried in my hooves is probably cluing her in. I don’t even remember how I got down here… ‘I’m sorry, Applejack,’ I gush, my forelegs muffling my words. ‘I’m sorry I’m sorry I didn’t…’

‘Hey! It’s alright! It’s okay! Look, I’d have figured that somepony in your… er… position wouldn’t be self-conscious about this.’ She drops the rest of the way to the floor and tries to meet my gaze, but I’m staring at my hooves.

‘Then why were you…?’ I flick a hoof toward her hindquarters, and she follows it, then breaks into a sheepish grin.

‘Oh. That. Yeah, I’d come – I’d walked here straight from Fluttershy’s…’

And the other shoe drops…

Tears are welling up in my eyes, but I’m not going to cry. I’m not going to cry.

Her mouth jerks into a silent ‘oh’, and the little bit of her face I can see out of the edge of my vision goes pale. She dips her head to where she’s almost looking me in the eye. ‘Sugarcube… this was somethin’ different, wasn’t it?’

How do I even answer that? Just thinking about it is wasting concentration I need to keep from bursting into tears. And now I’m not even going to get dinner tonight. I almost laugh.

‘Look. Fluttershy and I ain’t an item in any sense of the word. Just sometimes we need to…’ Applejack slides her hat over from where it’s lain on the floor the whole time and clutches at it. ‘To be honest’ – how can I not trust her when she says that? – ‘I always considered you out o’ my league. Back when we were in school together, everypony wanted to be like you, and now… Apple Bloom thinks so highly of you.’

I manage a small smile. At least it appears I’ll get out of this with my dignity.

‘And I’d have never expected in a million years that you’d ever give me more’n a second look.’ She rubs a hoof up and down the back of her neck, flashes a lopsided smile, and scoots over next to me. ‘I knew what kinda stuff happens here, and… I went along so I could fool myself into thinkin’ I was somethin’ special, somethin’ more’n just a pony you thought needed a bit o’ help.’

‘Not you, Applejack,’ I say quietly. ‘Never you.’

She swallows hard. ‘I-if you’re game – look at me, bein’ the forward one – I’d like to see where this goes.’ Despite her words’ confidence, she’s fidgeting with her hat and casting her eyes around in every direction but mine. ‘Can I see you sometime? Like, on a date?’

‘You don’t have to do this.’ Isn’t that what I’m supposed to say? I can’t imagine there’s actually etiquette…

‘I know I don’t. But I asked anyhow.’ She raises her eyebrows and pricks her ears forward, a faint curl turning up the corners of her mouth. ‘’Cause it’s what I want.’

I reach a hoof toward her shoulder, and she doesn’t shy away, so I hook it around her neck and give her a small hug. ‘I’d love that, Applejack. I’d love that.’ Maybe I can make sense of what just happened over the next couple of days. But I’d better not waste this gift that fate has dropped on me.

‘How about tonight? I was just about to head home and cook a late dinner.’ She studies my face, then breaks into a smile.

I couldn’t wipe this grin off my face if I tried. She just… amazes me. Always. All I have left to do is prove that I’m worthy of her. Easy, right? But I’m almost there. Almost there.