Cheerilee's Special Valentine's Day Class

Snails stepped into the darkened room. It held many memories for him. Memories of long chats with Snips about pollen and bees and of talking about how awesome it would be to one day clear out all the glue in Cheerilee’s cabinet for their enjoyment. It also held bad ones though, like the day Snails found out Silver Spoon didn’t like him or what everyone actually thought of him. Tonight, those memories were laid to the side, though, his mind too distracted by a mare he knew quite well, who stood behind a silver dining cart in the candle light.

“Hello Snails. Did you receive my valentine?”

He nodded at Cheerilee, the note clenched in his hands as sweat dripped down his brow. His teacher had never dressed like this before, nor had a sultry lilt to her speech. A short black dress clung to her body and let her smooth, magenta legs be shown to all. Snails actually currently found more comfort in them then her large bosom that was trying to come out of the top of the fabric. Not that they weren’t quite tempting to stare at, but that only caused him to force his gaze even harder upon the ground.

A small tisking sound entered his ears as her hoof steps came closer and closer. Cheerilee pushed herself up on to the balls of her feet and blew against Snail’s neck. The tall stallion shivered and he immediately gave her his full attention. “Is that any way to greet your love? Even you should know better.”

Snails swallowed hard and twisted the note. “But, um, you’re my old teacher, no–nott my love.” A small pulse of shame went through him as her eyes drooped. “No-not that you don’t, um, look very… pretty?”

Cheerilee’s face came below his and he could feel her body only an inch away from his. “So cute, just as always. As for the problem, for tonight, simply consider me both. A teacher, and a lover. Someone to help my students now that they are eighteen and adults learn the intricacies of romance and dating.” She wrapped her arms around his slightly muscled body. “I chose to ask you because I knew you would need the most help.”

“Wha-what do you mean?” Snail’s mouth felt like a desert, as he almost could look down her dress. Those beautiful green eyes drew in his attention. The slight shimmer of the firelight in her pupil, and something deeper. Sadness? He leaned in closer to get a better look. “Cheerilee?”

She shook her head, breaking the gaze and then grabbing his hand. “Please, call me Cheer. Now come along my beloved. I prepared a special meal just for the two of us and there is much for me to teach you before tonight is over seeing as, like most stallions, you know nothing about how to treat a mare, I would think.”

Snail’s stumbled as she suddenly pulled on his arm. Once at the small, candle lit table, she gestured for him to act first. “What do you do now for a lady?”

He bit into his lip and flexed his fingers before glancing back to Cheerilee. “Um… tell them they’re pretty?”

She giggled. “No, but that wouldn’t be bad when you first see your mare or when you two are seated. However, the first thing you should do is pull out the chair for her, make sure she knows you are a gentleman.”

Snails nodded fervently before speeding to the right side chair and pulling it from the white cloth. Cheerilee sat upon the warmed wood and gestured for him to sit. He cursed to himself for being just as stilted in his motions as he had been whenever he had to walk to the front of the classroom all of those years before. This was so weird and new and he didn’t want to mess up, so he was focusing too much on making his movements correct, which only made them seem even more incorrect. It was a habit he had never been able to shake and only made him feel even more nervous in front of such a pretty mare.

Cheerilee grabbed the top to her platter and revealed a heart shaped salad with thick olive dressing over it. Snails did the same and then looked up because of Cheerilee clicking her tongue. “Yes?”

“Next question is what you should do to start the conversation. What would you start a first date with?”

Snails picked up his fork and then grinned. “Thank you for cooking.”

A slight giggle met his ears. “A wonderful answer, though unexpected. For that, a small reward.” She leaned in closer and Snails felt himself lean in expectantly. “I’m not wearing any underwear.”

She sat back as Snails turned bright red and stammered out, “Well, um, they look, er, quite nice without it?” He started to twitch as Cheerilee watched him and then shook her head.

“Your first compliment really shouldn’t be about my bosom, though I suppose that is my fault. Girls like to be told they’re pretty, sexy, even cute sometimes, but usually about something a little less obvious. Now Snails, I know when you really try you can have some marvelous insight, so please, give me your all.”

The light flickered into his vision as he spent a moment attempting to focus. Snails felt his attention waver, wanting so badly to look back to her chest. His teacher had always been a marvel for the colts to admire, but the thought of her unsupported. Wait. He looked up with a large smile that caused Cheerilee to chuckle. “I love… you. How you are. I’ve always admired the fact that you didn’t ever need anyone and yet could still bear your heart and self to anyone who needed you. It really pulled me through on some of the tougher days.”

Snap.

Snails glanced at the now broken metal fork that Cheerilee held. “Cheeril-?”

She shook her head and looked back at Snails. “That… that was beautiful Snails. An answer truly worthy of a reward.” Cheerilee hooked her thumbs beneath her dress straps and pulled them off her shoulders. Snails eyes grew wide as the fabric was set free and her chest sat there exposed. “Remember, it’s not polite to stare.”

His eyes immediately went to his food and he licked his lips, tasting blood. He couldn’t really worry about the bloody nose or heat resonating off of his face as he tried to think of anything else. The gentle curvature of her breasts wouldn’t leave though. Snails wanted so badly to feel what he could only guess were soft mountains of wonders, but she had been his teacher! He lazily popped in a bite of salad and tried to use the taste and sound to drown out his young libido.

“Is it good?” She breathed a sigh as Snails nodded, but did not look up. “I believe now is time for our advanced lesson as I fear you may not be able to enjoy my more… regular lessons. A mistake on my part for giving such large distractions I suppose.”

The scraping of her chair and the giggle that filled the air almost made his heart stop as he sat there, stock still. Snails didn’t even breath as her hooves sounded off quietly against the wooden floor. A warmth came against him as two slender arms curled over his chest. Something soft pressed against the back of his skull and he felt his crotch twitch with need. Her breath came against his ear just before her teeth. “Cheeril-Cheer?”

The arms around him tightened and her breath came in sweet against Snail’s ear. ‘What do you think your biggest problem is?”

He opened his mouth before closing it immediately. So many options had filled his mind and a tear came to his face. He didn’t like being made to think about the topic and instinctively wrapped a hand over the comforting grip upon him. This was returned by a small stream of wind against his neck before her lips kissed the back of his ear.

Cheerilee almost didn’t breath as she gave him the answer. “You are timid, innocent. While admirable in a colt, you are eighteen. Certain things are expected, like you showing more interest, or being bolder. So please, when a woman exposes herself, despite what she says, enjoy them. It is a gift to the one they love, just as every hug and kiss is.” She ran her tongue gently against the ridge of his ear before nuzzling the top of his head. “Will you give me a gift back?”

It took him a moment to figure out what she could mean and swallowed hard. Snails could have stopped her. Their relationship would already be changed by this though, and it was a change he liked, if he were honest. A slight push against the chair brought him up and he bent his neck back. Cheerilee met him halfway and brought her lips against his for a light peck.

The arms against him moved away for a moment as Cheerilee brought herself around and sat into his lap. His whole body felt warm as he looked upon her. One hand was brave enough to follow his gaze, tracing over her soft stomach, her tender thigh, and then hesitating below her plump breasts. “You look amazing.”

Cheerilee nuzzled against him. “Thank you. You’re too kind to this old mare.” Her eyes glanced down as her thigh was poked by a rather large needle. “I’m happy to know they aren’t just words though. Now, remember how I said you were too timid? Prove me wrong.”

Her body stayed pressed against his. Heat radiated off of her bare limbs and her plump breasts pressed tight against his chest. Snail’s first thought was to touch her, and only for a moment did he stop those thoughts before allowing his hands to wrap around and touch her rump. It was nice and firm, providing a good place to grip. This made pulling her in for a kiss extremely easy as he enjoyed her sensual thighs.

Snails almost regretted kissing her from the moment it began. The older mare met his passion in equal amounts, if not immediately exceeding it. He also found out what a wonderful experience it could be as his tongue became coiled with hers. Their hot kiss seemed to last an eternity as his was pulled, twisted, and even tickled. Her slimy coil finally vacated him as he panted against the chair and stared at the ceiling. She licked her lips, taking in the fine line of drool from the stallion.

“Wha-wha-what was that?”

A small giggle escaped Cheerilee. “Just a kiss. Trust me, from eighteen to my age, you’ll know a lot more, and a lot better. I’ll even prove it to you, if you need it.”

Snails looked into the distance, still stuck in complete bliss and bewilderment. “That sounds amazing.”

Cheerilee leaned in again for a light kiss this time. “That’s what I thought you would say.” She put one hand on his chest. “Now, be a good boy and let me see that nice chest of yours. I’ll take care of the pants soon enough.”

Snails swallowed hard at that but nodded furiously as the heat on his face increased. His hands fumbled for a moment as he gripped the shirt and then started to pull it over his head. He stopped midway from Cheerilee’s hands rubbing his abs and her tongue coming between his pecs. The shiver that started then only increased as she licked, kissed, and suckled on his tough, sculpted abs.

Cheerilee backed away as she got to his jeans and looked up into Snail’s face. His shivering stopped cold as she took the button holding them together into her mouth. No. She can’t be. That isn’t– Snail’s jaw lost control as she came away with his pants undone and a low “Uh,” came from the him.

Soft hands came against his underwear and Cheerilee sat on her legs between his. “Snails, I need you to calm down. I know you’re bewildered, but just relax. I know what I’m doing and you have nothing to fear. Tonight is about being with each other without fear. With that in mind, will you relax? For me?”

He stared into the her soft green eyes and felt comfort wrap around him. It honestly amazed Snails. Cheerilee was bare naked, about to do Celestia knows what to his penis, and yet he could still find that calming, caring wave through him that always came with her smile and beautiful eyes. He leaned back in the chair and let out a long sigh, trying to calm down.

This attempt failed when the pressing of his underwear left his crotch and he smacked Cheerilee with the large, girthy member. She blinked a few times before licking her lips. “Well Snails, for anyone who thinks you haven’t grown up, I have some bad news for them.”

Snails covered his face as his throbbing cock twitched in the air. “Please Cheeri– Cheer, this is embarrassing enoAah!” He jumped a little in his chair as the tip of her tongue lapped up the small bit of clear precum on his tip. His hips tried to buck upwards as she kissed the tender space, but soon found the space vacated while Cheerilee continued her nuzzling along his shaft.

Her tongue ran along the pulsing veins as grunts of pleasure escaped Snails. Thi-this is nothing like by myself. This… this is amazing, like Trixie’s magic show mixed with a triple fudge sundae. The thought caused his balls to clench and he found a hand firmly clamped on his crotch in response. “Nng.”

Cheerilee gave an apologetic kiss onto the base of his shaft. “I’m sorry, but you need to learn to wait. A stallion can’t go on forever, so you need to try to hold back so the mare may get off. Think you can do that for me?”

Snails nodded and immediately found it rewarded by Cheerilee popping one of his balls into her mouth. The thorough enclosing of the sensitive part almost made him break down, but resisting the primal urge was well worth the continued moans from his lover.

She smiled and pulled gently on the morsel in her mouth. Her lips soon moved away from the base, slowly kissing and suckling the shaft on her way up. Each moment brought another twitch of not only Snail’s member, but also of his hips. By the time she got back to the tip, the poor colt was shaking and panting like he had run a five mile marathon. “Thank you for being patient. For this next part though, don’t hold back. Give me all of my dessert.”

Snails didn’t quite know what she meant at first. This quickly changed as her ruby lips opened slowly, but only just enough to keep a steady pressure against the shaft. The stimulation became almost painful as she slowly drifted lower and lower, her lip creeping over each new centimeter and bringing it into her tantalizing and slimy grip. His eyes rolled back as he gave into the last command from his teacher and his hips met her halfway. A small yelp came from Cheerilee as her throat was filled with her special treat for the night.

Snails felt his dam break in almost an instant as her throat had become a vice grip for him. Shivers ran down him as well and a loud groan escaped his lips as he found his pleasure being allowed to peak. A small tightening was all that came as a warning for Cheerilee. Her throat pulsed once, twice, three times before she finally pulled away and cum filled the air before landing over her face. Snails tried to mumble an apology, but couldn’t with how exhausted he felt.

Cheerilee took one finger and collected one of the loose strands of sticky liquid that covered her face and slowly sucked on it. “I am quite impressed with the amount. I did not expect to be treated that well.” She gave a small giggle and Snails felt his own mood lighten at the joke.

It’s still my teacher. My good humored, well meaning, teacher. Snail’s comforting memory faltered as she tried to stand but failed, causing her to fall back with her legs spread open. There in front of him was a glistening pink slit that shared its sheening liquid with two tender, inner thighs. His mouth slowly came open as a slight blush came over Cheerilee’s face. “Pe-perhaps you can help me to the bed?”

He nodded numbly and slipped down to her. After carefully picking Cheerilee up, the two walked over to the bed and Snails laid her back down, but this time on to the bed. Her hand caressed his face and then gently pulled him towards her. Their lips met for a brief moment before Cheerilee stretched herself out. “Please Snails, touch me.”

Snails didn’t even hesitate this time as his lips came rushing against hers. Her tongue only slightly played with him. He didn’t mind though. She had put up with a lot already and he guessed it was his turn now. His hands decided to attempt to make sure of this fact by coming down to her chest and gripping them gently. A slight moan escaped his old teacher and he came away. “I-is that good?”

“Ye-yes. If you really want to hear me moan though, maybe you should try licking them?” His mind stopped for a moment before a gentle force on the back of his head brought him into the soft pillows that covered her chest. The fingers ran through his hair as he nuzzled into them, his hands firmly digging into the mounds. “Don’t lose this innocence. It’s too cute.”

A blush came across Snails face and he decided to try to prove her wrong. A small gasp came from Cheerilee as his tongue came across her stiff nipple. His mouth soon enclosed the teat and he started to suck gently upon it. One hand came over her other breasts and started to move it back and forth. Cheerilee shuddered and bit into her lip as his rough tongue ran back and forth along her tit.

Snails buried his face further into the soft fur just as a sweet taste touched his tongue. He immediately sucked on the breast without a second thought, only much harder than before. The effort was received by an ecstatic yelp from Cheerilee and another burst of sweet, creamy liquid running down Snails’ throat.

Cheerilee writhed against him as his grip became stronger upon the other breast. His arm around her back pulled her up so as to have easier access to the milk while the other moved away and pressed firmly next to the bed for support. Snails’ cock soon was coming back up as his throat pulsed up and down. Cheerilee’s mouth opened as she panted and pushed against his head. It took a lot, but finally she pried him away.

“Wha-what is wrong?”

“I… I just thought you might want to feel what it’s like to get a mare to clamp down on you full force, and trust me, there is no better time than right, now.”

Snails was actually slightly intimidated by the almost predatorial tone, but soon she was back to panting and leaning against his chest. He smiled and only then realized just how hard up he was with a pained groan. He laid her down and gently spread her lovely thighs. Staring into the glistening crotch, his only thought could be about just how pretty it looked in the candle light.

She had her head back and seemed surprised when his face came up to hers. “Wh–what is it Snails?”

He swallowed hard as his legs spread apart and his cock started to slide against the entrance to her pussy. “I… I just wanted to let you know that I love you Cheerilee, and that I’m really happy to be losing this to you.”

She was quiet for a few long moments before she looked back at him with tears in her eyes. “I… I love you too Snails. Now please, don’t tease me anymore.”

Snails was all too willing to oblige. One moment his large cock was quavering in the open air, the next, it thrust into her halfway and caused her to gasp. He let out his own grunt and felt his arms waver. She felt unbelievable, wrapped around him, and all he wanted was more. His shaft was soon retreating back out of her, dragging her sensitive folds with it.

The next thrust found Cheerilee screaming on the bed and caused Snails to pause as he worried for her safety. The panting smile and thin line of drool on her face dismissed the worries, thought that bit of drool was far too tantalizing for him to ignore. He came in for a kiss at the same time as his hips slid back. This time Cheerilee’s hips bucked back in a desperate attempt to keep him there, but simply couldn’t, leaving her waiting expectantly for the next thrust as her tongue weakly played with his.

Snails kept the kiss going as he finally found a rhythm. Each surge forward would bring a loud yelp from Cheerilee and rivulets of liquid spread against their chests. Each drag back came accompanied by a long, sensual moan from deep in her throat that almost drove Snails insane with sensation when mixed with the clingy nethers that simply would not let him go.

The kiss finally broke with Snails gasping for air. He soon put his face into her neck, snuggling into the warm fur and feeling her stiff nipples grinding against his own chest. A small whisper was in his ear, Cheerilee trying to tell him something. Whatever it was though was lost amongst desperate pants and long moans.

Snails thrust one more time and felt Cheerilee tense beneath him. Her tight fit suddenly became a vice that caused him to freeze as well as she let out a primal scream. A strong current of something passed over Snail’s member, allowing him to pull it out once more despite the vacuum suction it had . She shuddered for a few more thrusts before it was Snails’ turn to let out a final, primal bellow.

He shoved his cock forward as he sucked on her neck, trying not to bite in as his body tensed. His crotch tightened and he shook. Soon he felt his hot semen fill her and felt her folds tighten around him one last time as he finished. Snails panted a few more times, before collapsing to the side and staring at the ceiling.

A soft hand caressed his chest and he got to take in the spectacle that was Cheerilee. Her chest, along with his, was covered in white, creamy milk. More white liquid spilled from her crotch and he swallowed hard. Unable to say anything though, he could only lay his head back. The words, “Sleep well. You earned it, and an A plus in mare satisfaction,” lulled him quickly to sleep.

Cheerilee smiled down upon him and kissed his forehead while tears welled into her eyes. “Yes, yes, I do love you, but it can only ever be for tonight.” She then laid down against him and fell asleep, sad, but also satisfied.

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