Not*worthy: A Story of Sex and Introspection

The schoolhouse, normally abuzz with action, looks abandoned. There are no foals on its playgrounds or chasing each other in its field. No flag flies from an empty pole. Its tall windows are dark, blocked by curtains. Trotting by, it seems entirely empty.

I know better.

I climb a few white steps and stand under the canopy. I knock. There’s no secret knock here; I know she’ll come to see who’s there.

The sun is rising in the sky. The canopy’s shadow creeps down the door. I knock again.

Cheerilee opens it moments later. For just a moment, she wears the smile of a curious teacher. As soon as our eyes meet, that smile drops to an exasperated gape.

“Noteworthy?” Cheerilee asks in a hushed voice. She peeks around me. Very few ponies are in sight, and none of them are paying attention to us. “What are you doing here?”

I shrug. “I thought I’d come see my favorite teacher.”

Cheerilee’s eyelids droop halfway down her eyes. “Oh, yes, of course, ha ha.” She moves to close the door. “I’m sorry, Noteworthy, I’m very busy. Now’s not a good time.”

I stop the door with an extended hoof. “Cheerilee. I’m sorry for barging in. I’m not here for… anything special.” I smile gently. “I’m just having a weird day. Is there anything I can do to help?”

Cheerilee’s eyes narrow. They scan me, up and down and up again. “I could use a hoof,” she says. “Just… no funny business, okay?” She steps aside and lets me in. “I’m not in the mood.”

“I understand,” I say.

She shuts and locks the door behind me, and we trot into her classroom side by side.

“What are you up to now?” I ask, eyeing the room’s many decorations. “Looks ambitious.”

“Ha! Yes, well…” Cheerilee continues to her desk where she resumes cutting something out of a large piece of silver construction paper. “I do love my students.”

“I know,” I say. On a whim, I wink.

Cheerilee slams her hooves on the desk with a groan. “Please, Noteworthy, not today. You were never a student of mine.”

“Eehhh…” I tilt my head back and forth.

She finally breaks. She giggles. I watch her ears move with the laughter. It’s one of my favorite things about her.

“Oh, stop it.” She waves a hoof at me. Her entire mood is different in one instant. We’re friends.

“Sorry. What can I do?” I look at the materials spread on and around her desk.

“I need to hang these stars in constellation patterns around the room,” says Cheerilee, pointing to various corners of her large classroom. “I want the Ursas over there ― the front of the room will be north, see? ― so Capricorn goes over there…”

For an hour, I help her. I hold a ladder steady, or else arrange the stars myself. She directs me in everything. Her voice is so effortlessly cheerful. Every time I look down from the ladder, I see her staring at my flank. She tries to look away quick enough for me not to notice.

We hang Draco and Orion. The stars stick to the wall with tape. Some of them hang from the ceiling by different lengths of string, spinning lazily in perfect patterns.

“This is really impressive, Cheerilee,” I say when Scorpius is finished.

“Thank you,” she says with a smile. “It took a long time. And, honestly, I’m glad you dropped by. This would have been a pain all on my own.”

“We’re done, then?” I ask.

“Almost! Aquila’s next, uhh… somewhere over there.” She jabs a hoof at a wall, checking her desk for specifics. “And then you can go. Thanks for stopping by.”

“You won’t leave with me?” I squint a bit. “Nopony would think twice about us leaving the schoolhouse together. They have no idea.”

“Hmmm. Thank Celestia.” She shot me a coy look and returned to her star map. “No, I’ll stay here for a while longer. I have lots of homework to grade.”

“Why not grade it at home?” I ask. “I can walk you there.”

“Please stop.” Cheerilee swallows dryly. “You know very well why I can’t do work at home.”

“Ah, right.” I nod. “Sorry. I forgot.”

“My sister is so annoying,” Cheerilee whines, closing her eyes in anger. “She’s loud and disrespectful and infinitely distracting.”

“I thought she was leaving after a month?”

“That was the plan!” Cheerilee guffawed. “But it’s nearly half a year now and she’s still just bumming on my couch. Why doesn’t she just get a clue?”

“Why don’t you just ask her to leave?”

Cheerilee grimaced. “I wish I could, Noteworthy. I’m afraid that, in real life… I-I’m not very aggressive.”

“In real life.” I laugh. “I get it.”

“You ought to.” She shakes her head at herself, though she’s smiling. “You’re the only one that ought to.”

“I know you’re trying not to talk about it,” I say in a low voice, “but I have to say, Cheerilee: that night with you was the best I’ve ever had.”

Cheerilee bites her lip. She blows air through her snout. For just a moment, I’m afraid I’ve gone too far, that I’ve really upset her.

But then a smile pulls at the corner of her beautiful mouth, and without raising her head she looks at me with those soft green eyes. “Which one?” she asks.

I smile back. “All of them,” I say. “But especially the night we had here.”

“Ugh.” Cheerilee turns away, laughing softly to herself. “That’s so embarrassing.”

“It was fun. You had a blast.”

“So did you, I hope.”

“I did.” I took a step closer to her desk and whispered, “Do you still have it here?”

Cheerilee whipped around with an exasperated expression. “What!? No! Heavens no, Noteworthy. Goodness, you think I’d keep that here? Where my students could find it?”

“They wouldn’t know what it was!” I said.

She raised her eyebrows. “You’d be surprised. I often am.” She shuddered. “The things I hear some kids say at recess…”

“We’re all pervs on the inside,” I tease.

“I’m not a perv, Noteworthy,” she said. She paused. “And neither are you.”

“Thanks,” I say. “I hope not.”

“You’re very sweet.” She looked up at our work. The room was dim, and the silver stars shone all over the walls. “You didn’t have to do this. It was very nice of you to help.”

“I like spending time with you, Cheerilee,” I say. “You’re beautiful.”

She coughed loudly. “Whoa. Don’t you mean ‘nice to be around’ or something?”

I shake my head. “That’s true, but it’s not what I meant. You really are beautiful.”

Her entire snout turned a redder shade of burgundy. “Well. That’s certainly forthright.”

“You don’t hear it enough,” I say, touching her on the nose, “judging by your reaction.”

She lifted a back hoof, but didn’t step away. She let me run my hoof along the bridge of her snout. She closed her eyes.

With a sudden harumph, she turned away. “Not today, Noteworthy,” she said breathlessly. “I told you, I’m not in the mood.”

“I wasn’t, either,” I say, “until I saw you staring at my butt.”

“Guh! Excuse me?”

I smirk. “I saw you watching me on the ladder. What, have you never noticed there are two quavers in my Cutie Mark before?”

Cheerilee’s jaw juts forward. She shakes her head slowly.

I raise one hoof above my head. “Teacher? If each quaver has two notes, how many notes are on my flank in total?”

“That’s something the teacher would say, not the student,” Cheerilee snaps. Her irises shrink and she drops her face onto her desk. “Sweet Celestia, what am I saying?”

“Teacher! Something’s happening to my body.” I offer an innocent expression. “Please, can you help me understand what’s wrong?”

“I’m such a freak,” Cheerilee grumbles. “I’m such a disgusting freak.”

“You’re not a freak,” I said, touching her shoulder. “You’re my favorite teacher.”

She slowly raises her head and faces me. Our muzzles are inches apart. I can feel her breath on my lips; her mouth is hanging barely open. We move even closer. There are no other sounds but her trembling breath. My ears feel hot, and I watch her stare at my mouth for a long time.

“You’re making me tingle all over, teacher,” I whisper.

“Nngh. Fine.” Cheerilee rears up onto her hind legs, grabs me between the ears with one hoof, and shoves my face into her crotch.

“Mmff!” I pretend not to know what to do. “Teacher!” I say.

Cheerilee bends over to whisper in my ear, “Safe word same as last time?”

I nod. My snout rubs against the outside of her vagina. She breathes like she’s just gotten into cold water. She reaches her forehooves back, still standing, and steadies herself on the desktop. I use my lips and tongue to play with her privates.

“You’re doing great down there,” she says in an uneven growl.

“But I don’t know what to do, Teacher,” I say into her folds.

She moans. The first hints of moisture join my searching tongue.

“You’re a natural,” Cheerilee grunts. “Go faster. Do it faster.”

I speed up, licking up and down between erratic kisses.

Cheerilee kicks open a drawer in her desk and reaches for something within. I see its shape out of the corner of my eye, stuffed between two full manila folders.

“I knew it,” I mumble into her pussy.

“No talking in class!” Cheerilee shouts, slapping my head between my ears.

I whimper and continue my feast. There’s something I love about eating out a mare.

“Yes! That’s it, right there. Nibble on that some more.” Cheerilee is breathing quickly. “That’s called the clitoris, Noteworthy. Do you know what the clitoris is?”

I shake my head.

“Oohh! It’s the center of my pleasure.” She strokes my head. “You want to make Teacher happy, don’t you?”

I nod.

“Good. Turn around.”

I open my eyes wide and look up at her pathetically. “What?”

“Turn around, damn it!” She grabs me under the jaw and throws me to one side.

I topple to the ground, then scramble to my hooves. “T-Teacher, what are you doing?”

Cheerilee loops it around her waist. It buckles behind her, tucks between her legs, and cups over her groin. Its most obvious feature is a long, dark green rod. Just the sight of it makes my insides hot.

“Oh no…” I wheeze. “Teacher! Teacher, please!”

“Quiet!” she barks. She angles herself behind me, reaches over my back, and pushes my head toward the floor. “You’ve been a very bad student.”

“I-I have?” I stammer.

“Disrupting the class―” Cheerilee lifts my tail and rubs the tip of her rubber shaft between my plot cheeks. “―pulling the fillies’ manes―” She squeezes the rubber with a grunt, and a line of lubricant squirts under my tail. “―calling me names behind my back!” In torturously slow movements, Cheerilee uses the fake penis to spread the lubricant around my anus.

“No, Teacher, please! I-I didn’t mean any of it!” I sob; I choke on my own gasps. “Please, please, I’ll be good! Don’t do it, Teacher!”

“You’ve already made your choice, Noteworthy.” Cheerilee’s voice has changed completely. “I’m gonna teach you how to grow up and finally be a stallion.”

I bend my neck to look in her eyes. She looks angry, excited, and fierce. I gulp. I try hard not to smile.

“Augh!” Cheerilee thrusts forward. The thick rubber pushes an inch into my colon.

I shriek and turn my head to the ground, slamming my forehead into the floor. “Ow! Ow ow ow ow!”

“Shut up!” Cheerilee pulls out completely, then rockets her hips forward again with a “Grrr!” She’s standing on her hind hooves, holding herself up with one hoof on my ass, pulling my tail skyward with the other.

“Gosh freakin’...” I clench my teeth as the rubber slides deeper. I like Cheerilee―I really do―and seeing her let loose like this really turns me on. On the other hoof, I am not into butt stuff, and the pain of her strap on is almost unbearable. Still, something about it feels good, and my penis stiffens as she moves in and out of me.

“Oh yeah, oh yeah…” Cheerilee grunts. I hold in a chuckle. She’s so adorable, but I don’t want to ruin her fun. “Take it, Noteworthy. You deserve this.”

My desire to laugh fades immediately, replaced by a shiver deep below my sternum. “I deserve this…” I repeat quietly. This is why I came here.

She’s taking it slow. I’m grateful. Cheerilee breathes hard while she gyrates back and forth, loosening my asshole in preparation of what’s to come. I already know her game; I know what she likes. Soon enough that rubber rod will be nothing but a dark green blur. I swallow hard and say it again: “I deserve this.”

“That’s right. Take it.” She leans into me. “Take it all.”

“Ooooo! Ow! Ow ow ow!” I wince. “Orange peels! Orange peels!”

Cheerilee pulls out instantly. Her voice rises to its regular pitch. “I’m sorry! Was that too much?”

“It’s okay,” I say. My voice is even higher pitched than hers for a moment. “I’m okay. Give me a second and you can go back in.”

She nods. “I’m sorry―”

“Don’t be. It’s okay. Just… hold on.” I take several deep breaths. I close my eyes. I imagine a different face behind me… but that only hurts worse. I eject that face from my head like a clay pigeon and search my imagination for another solution.

Finally, I get a weird idea. I laugh a little.

“You ready?” Cheerilee whispers, already pressing the dildo to my pulsing anus.

“Yeah.” I nod, eyes shut tight. “Yeah, do it.”

“You really do deserve this, Noteworthy,” she says, her voice resuming a lower tone while she mashes the rubber back into my colon. “You’re such a bad, bad pony.”

I pull my head back. “Yes! Yes, I’ve been simply terrible! Take me hard, Cheerilee!”

“Raaaugh!” Instantly, she revs up the speed. She doesn’t go all the way in, but she yanks and thrusts the lubricated rubber in and out of my body like a steaming piston.

I feel my skin ripping slightly, but I don’t complain. I make a lot of noise. I pretend my coat is white, and that locks of violet hair are bouncing around my face. “Yes! Yes! Yes! Oh! I deserve this! Give it to me! Aaahhh, more! Harder!”

Rarity has asked me on numerous occasions for anal sex. I always deny her. There’s something about it that makes me very uncomfortable.

“Yes! I love it! I love it in my ass! Harder, Cheerilee! Faster, Teacher, Faster!”

It helps to have a vivid imagination in moments like these.

“Gaaaahh!” Cheerilee is absolutely roaring. It’s invigorating.

“Oh my… oh my! Oh sweet Celestia! I’m gonna cum!” My eyes fly open. I’m Noteworthy, and I’m cumming. “I’m cumming!”

My rock hard penis spews its load onto the classroom floor. It shoots down in long, fast streams, splashing between my hind hooves.

“Ooohh-ho-ho-ho!” My eyes are twitching. My ears are pressed flat against my head. “Oh wow oh wow oh wow oh my gosh oh my gosh oh wow…”

It feels amazing. The ejaculation stops, but the orgasm lasts while Cheerilee continues to pound my ass. For a moment I want more, and then the chemicals fade from my brain and my blood and I’m suddenly screaming, “ORANGE PEELS!”

Cheerilee complies immediately. She pulls out and stumbles backward, collapsing onto her haunches. She’s sweating from her brow, breathing hard, eyes unfocused.

I roll to one side to avoid my own cum and land hard on my ribs. It doesn’t hurt nearly as much as my anus does. I grit my teeth and breathe slowly. The worst of the pain passes soon enough.

“I’m… sorry… if that… was too much…” Cheerilee pants, pressing her hooves into her temples.

I manage and smile and shake my head on the ground. “No. It was great, Cheerilee.” I hiss from a bout of pain. “It was exactly what I needed.”

“Yeah… me, too.” Cheerilee’s smile is wide and genuine. “Ahh! My goodness, Noteworthy. You can really take it.”

I chuckled and struggled to my hooves. I backed up and sat upright next to Cheerilee. I leaned my head on her shoulder and smelled the sweetness of her mane. “It hurt a lot,” I admit.

“Too much?”

I shook my head. “No. You didn’t hurt me. I would do it again.”

She laughed and rested her head on top of mine. “Someday, Noteworthy. Not soon, but… someday.”

“Would you ever want to switch places?” I ask.

She sighs. “I don’t think so. Would you?”

“No.” I nuzzle her neck. “I was just wondering. I don’t want you to hold back.”

“I don’t. That’s exactly what’s… so fun about this, I think.” She hums as I kiss her neck a few times. “You make me feel like I can do whatever I want. Without shame.”

“Good. That’s exactly my intent.”

She puts a hoof around me. “You’re a good pony, Noteworthy.”

I frown. “Don’t ruin it.”

She laughs, and I pretend to laugh along.