Cheerilee's Special Valentine's Day Class

You walk into the classroom and immediately feel an almost predatory gaze upon you. You turn to face the person in the room, only to see Ponyville’s school teacher awaiting him. Or, at least, you hope it is the school teacher. The low cut, white blouse she wears has her nipples almost poking through the thin fabric, but your eyes soon leave them as her hands run down her body. The magenta digits drag your attention to her round thighs that are hugged by a small, gray skirt. In the position she is, on her desk, legs wide open, it hides nothing.

You take a step back and swallow the saliva that has filled your mouth. “Mi-Miss Cheerilee?”

She shakes her head and beckons you over with a golden envelope that she grabbed from her desk. “Please, while we are like this, call me Cheer. It’s what my friends in high school called me.”

Your feet force you forwards, but only a little bit. “Ma-may I know what is going on?”

Cheerilee glances down and bites into her lip. “Well, where to start? I suppose I need to teach you a bit about myself before we begin the main lesson then. Tell me, especially like this,” she hops down from the desk and immediately bends back over it, giving you a great view of her rump, though her tail still blocks her back door, “how old do you think I am?”

Your brain short circuits for a moment. There were definitely quite a few lovelies in town, but you hadn’t gotten a good look at any of them in the few months since you moved. At least, not like this. “Twenty-three?”

A small giggle escaped her lips. “No. How I wish that were the truth, but no. I turned forty this year, and yes, I know I wear it well. But that also means more than twenty Valentine’s days without a special somepony and seeing so many other ponies go without.” She turned back to you with a determined glint in her eye. “I’m done with that.”

She walked towards you, quickly taking away the safe space that kept you from the seductress. “I am done watching all of these ponies be so lonely, so afraid, so ashamed. So now, I will fix that. I will be their Valentine and I will teach them and drive them forward like no one else will. I will teach, I will fulfill fantasies, but above all else, I will fuck.” She grabs ahold of your crotch, causing you to jump. “What do you say?

The hardening of your cock tells you you want it, and the lustful bedroom eyes from the pink mare tell you she is willing. Her lips clasp upon yours and you hold each other in a passionate embrace. Her wet tongue fills your mouth and pleasure courses through your body as the experienced intruder shows its skills. In an attempt to not fall behind, you lower one hand from her back and pull down the shroud of a skirt she had been wearing.

A shudder runs through the body that is pressed against yours, as the fingers you sent to explore find a ripe hole for the plundering. Your lips move from hers and onto the soft flesh and fur of her neck as further moans escape her. Meanwhile, your fingers are being firmly clung to by the tight hole you have found, and each squirming of the two digits is responded by a pant or whine from Cheerilee.

She rips her blouse off, allowing your lips full access to her heavy bosom. Your free hand runs along one of the perky tits while your lips gently kiss and graze the other. Her tit is sweet in your mouth as you put suction on the vulnerable nub. A gasp escapes her lips and soon she is undoing the button that keeps your jeans on. Her hand immediately grasps your firm cock and this time a groan escapes your throat.

She smiles at the thick member between your legs and pushes you away slightly. For a moment you resist, wanting to continue to ravage the heavenly mounds on her chest. However, the beginning of silky, soft strokes against your rock hard dick immediately makes you obey and back away.

Cheerilee’s body stays firmly against yours as she comes down and you finally get a chance to inspect your two fingers. A cold sweat breaks out on your skin as you stare at the sticky digits. Were you just in her ass?

You do not have long to ponder though as a long lick runs along your shaft before being completed by a kiss on the tip. You let out a long groan as Cheerilee’s tongue slurps up the precum starting to edge out. She doesn’t go down though. Instead, she raises even higher and soon your manhood is entirely enveloped by her bosom, minus your tip, which is continuing to be licked playfully.

You shake as her breasts start to rub fervently against your crotch. Each squeeze, turn, and push only brings you deeper into her magenta clouds. The twitching of your cock only seems to drive Cheerilee’s lust as her mouth becomes a vacuum upon your tip, eagerly sucking on it with full strength.

A final spasm and your walls burst. A surge of tension releases from you and your eyes roll back as finally spew your load into her eager mouth. Thick ropes of cum cause Cheerliee’s cheeks to bulge, and her throat spasms once, twice, three times before she turns away and starts to cough. Your cum comes out in one last spurt, the white cream accenting her face and breasts. “I-I’m sorry.”

She takes one finger and smiles before wiping some semen from her bosom and taking a long time to lick the finger clean. Your eyes are locked upon the sexy sight and only tears away when she stands. She giggles slightly. “Don’t be ashamed. In fact, it was quite tasty. Now, if your fingers were any indicator, there was one more place you wished to learn about before tonight was over?”

Your brow furrows as the haze of passion from before clouds your memory. The sight of Cheerilee bending over her desk brings your attention to the slightly open asshole when her tail flicks away from it. “Ch-Cheer?”

“As I said before, I’m done with people being sad, lonely, or unfulfilled today. So please, use me as you want.”

Only a moment is spent considering the proposition before you walk over. Your arms wrap around the beautiful mare and for a moment, it is nice. Simply a gentle embrace by two lovers as they prepare for the next step. Cheerliee breaths, “Thank you,” and her tail swishes against your groin. You let out a small moan as you straighten.

You consider whether or not to simply put it in, but decide to savor first. Cheerilee gives out a heated moan as your shaft runs along the crack in her firm rear. Your cock grows from only half awake to full attention almost immediately and you bend over once more with her. You grip the edge to the table as the tip of your dick pushes against her rump and take in a deep breath.

Cheerilee tenses as you push, each moment applying more pressure to her rump. After about a minute, you finally spread her puckered hole just enough to force your tip in. It immediately closes around your cock and a loud groan escapes your lips as you freeze. Cheerilee looks back at you with a soft, sweet smile and for a moment you feel like you’re back in school and not trying to get balls deep in her ass.

One of her hands comes around and presses itself against on your chest. “Don’t worry honey. This is your first time in the rear, right?” She watches as you nod and then smiles once more. “Don’t overthink it. Take it like you would a virgin pussy. Slowly go in and then listen to the mare. So in other words, for me, get all the way in and then do as you please, please.”

A chill runs up your spine at the last phrase and you slowly start to rock your hips. Her own rear slowly moves to help grind your cock further and further into her. Each inch brings another surge of pleasure as her ass tries to bring you deeper. It is a tightness you have never experienced before.

Smack

You glance down to see your dick fully consumed and Cheerilee panting against the table. A rise in your pride comes with her next moan and her hips attempt to drive you in even deeper. A short breath calms your nerves and steadies your entrapped member. You pull out almost entirely from her, grip the desk, and thrust.

“Gaahmmm.” Cheerilee’s arched her back at the sudden filling of her backdoor. She shivered and shook as you slowly ground your way back out, getting ready again. “Please, more.”

The hungry growl from the magenta mare is more then enough to get you to smack your balls against her heavenly hips again. Your body quakes at feeling her wrap tight around you again. Each moment of pulling out takes a large amount of focus, as even the most minor slip causes the tightness to attempt to drag you back in.

Cheerilee soon picks up on your rhythm, and you find the tables turned when she’ll push back against the desk and thrust you back into her. The first time gets you to grunt, the second one almost gets you to cum. You almost go back out when Cheerilee’s panting smile warns you of the danger. “Okay, you want to play it like that Cheer?”

“You know I do.”

You wrap your arms around her, gripping into her large breasts and pulling her to an upright position. For a moment, you simply savor it and kiss her. Her tongue only loosely coils around yours as her moans shake both of your throats. You would swear you are in heaven, with her rear firmly clamped around your cock and your fingers digging deeply into her soft mountains.

Cheerilee separates from the kiss, only to then whine against your neck. “Please. Finish me off.”

You nuzzle back and whisper, “Yes.” One hand stays upon her ample bust while the other snakes down. She jumps at the touch on her crotch, but then lets out a long moan from the three fingers that dig into it. You gently pull her away from your cock, almost taking yourself out. The grip isn’t the easiest with the fluid that is starting to crawl to your arm, but the fervent response from Cheerilee is more than worth the work.

Your fingers quickly leave her insides and switch to cupping her nethers and pushing. A surprised yelp comes from Cheerilee before a primal scream as you slam back into her, your arm providing even more force. The shaking against you warns you of her imminent climax, and you only just stop yourself from getting to the finish line.

Your fingers dig in deep one more time. Her rear almost tries to resist as she is dragged away one more time. The only thing keeping the hot school teacher upright at this point is your firm grip on her breast. You give it one more squeeze for luck before pushing right back in.

You let out a final groan of pleasure as her eyes almost roll back into her skull, as she utters a silent yell of pleasure. Her ass threatens to squeeze your cock off as a stream of liquid escapes her nethers. Your escape is aided by the thick torrent of cum you let loose into her rear. She lets out a final moan from the feeling of being filled to the brim with your warm, hot semen before her knees finally give out and she collapses to the ground. You soon follow, the amorous actions of the night catching up.

Cheerilee rolls over you and gives you one last, long, deep kiss. She comes away and nuzzles against your chest while her whole body warms you on top. A slight whisper enters your ear. “Thank you for letting me be your valentine. A plus, Ryuku.”