You spent a long time with Cheerilee

Saturday, December 17th

Cheerilee’s House, Evening

>Cheerilee answers the door when you knock.
>”Good evening, Anonymous. Come on in.”
>You enter her cozy little abode and sit down on her couch, now free of loafing sisters.
>She has a seat next to you and immediately snuggles right up against you with a warm hug.
>”Thanks for helping me out last week. Things have been a lot better between me and Berry.”
“I’m glad to hear that, Cheerilee. Looks like she’s not here today, huh?”
>”She’s been respecting my space and staying at home. Her husband is pretty strict about how much she can drink there because he doesn’t want her drunk around the foals, and she respects that rule. That’s actually part of the reason why she spent so much time at my place.”
“So has she been keeping her drinking under control?”
>”She has. Now that she understands her habit a little better, it’s easier for her to identify it and keep it under control. We’re all keeping an eye on her for now, but I think she cares about me more than she cares about getting drunk. So I’m not too worried.”
“That sounds really great, Cheerilee.”
>”It is. It really is. It feels like I finally have my sister back. And I love being with you. It makes me feel… youthful. The way I used to feel, back when I was the kind of rebel that wouldn’t listen to what anypony told her to do.”
>”Heh, then again… I guess I was still trying to rebel just a little bit. Holding on to that silly old grudge against my parents like that. I feel like I’ll be able to have a lot closer of a relationship with my family than before. I realize how important they are to me now. In fact, I might even take Berry up on her offer.”
“You want to move in with her?”
>”I admit… it’ll be a bit of a step down in terms of privacy or independence. But I want to be part of my family again. Pina and Pinch still call me Miss Cheerilee like everypony else, even outside of school. But I think I’m going to try to leave “Miss” Cheerilee in the classroom from now on."
>”I won’t let my life pass me by any longer. I’m going to start making more time for myself. And the ones I love.” she says, looking into your eyes warmly.
>You smile back and stroke her mane.
>There’s a bit of silence as she just smiles at you knowingly.
“... oh! Uh, I love you too!”
>Cheerilee giggles, “This isn’t a quiz, silly. I can already tell you love me.”
>She kisses you sweetly on the lips and smiles. “Care for a glass of wine?”
“That sounds lovely. You’ll have one too of course, right?”
>”Of course.”
>Cheerilee grabs a bottle and two glasses, pouring you a bit of the sweetly fragrant crimson wine.
>”Oh! Before I forget, I… have something else for you.”
“Something else?”
>”Hold out your hand, please.”
>You do as she says.
>She places something small into it, and as she takes her hoof away, you find a shiny little gold star sticker.
>”It… might seem a little juvenile, but I assure you that I have notoriously rigorous standards for what gets a gold star.”
“In that case, I’m honored.”
>Cheerilee grins, “I knew you’d get it. But this is my way of saying thank you. This gold star… means I’m completely amazed by your performance. I never thought I’d be able to turn my life around like this. And I have you to thank for it.”
>Cheerilee holds her glass up for you.
>You hold yours up to hers and gently clink it.
“Cheers.”
>”Cheers.” she replies warmly.
>You sat by the fire with Cheerilee for a while, sipping your wine together, running your fingers through her soft mane, and letting her cuddle up close nice and close to you.
>With the teacher’s head on your chest, and her foreleg resting over your thigh, it’s hard not to start feeling a little toasty after a couple glasses.
>As she rubs her head against her chest, her elbow slips up your thigh and brushes your hardening member.
>She looks down and gasps quickly. “Oh! I’m so sorry!”
>Cheerilee suddenly dives down inbetween your legs!
“W-whaa!”
>”Here, I’ll help you get them off!”
>The mare rapidly undoes the button of your slacks with her mouth and pulls the zipper down.
>She puts her mouth at the rim of your boxers and yanks them down, letting your stiff cock spring free and smack her lightly on the nose!
>”Ah!”
“Wha- wait wait wait, slow down for a sec! What are you doing?”
>”I was getting your pants off, because I saw you were getting hard. Doesn’t that… hurt?” She looks up at you hesitantly.
“Haha, nah, it doesn’t really hurt.”
>Cheerilee chuckles nervously. “Heheh… sorry. I guess I just thought… nevermind.”
>You tousle her mane gently. “Don’t worry about it.”
>A light redness comes to her cheeks as she glances over at your freed member.
>”Well… it’s out now. Mind if I…?” she trails off hopefully.
“Whatever you want to do.”
>Cheerilee smiles up at you, then turns her attention back to your crotch.
>She reaches with her hooves and spreads your legs apart to get a better view.
>The mare touches her hoof to your stiffness, gently pushing it back and moving it around, giving you a couple stray glances to make sure she isn’t hurting you.
>She carefully places her other hoof under your balls, lifting the sack and looking it over.
>”I see… so it’s all external?”
“Yeah, it just kinda hangs out.”
>”That’s really interesting…” Cheerilee says, leaning in curiously.
>Your eager marefriend touches her nose to the tip of your knob and gives it a light sniff that makes you shiver.
>”Mm…” she vocalizes in approval, moving her hooves up to the sides of your shaft, pressing them together gently.
>She angles them so the tips of her hooves are up near your rim, while the softer inner parts rest gently along the length.
>The curious teacher rubs along your shaft with a gentle pressure, squeezing it between her hooves, watching it intently.
>”How’s this?”
“It’s good… you can go a little faster.”
>At your encouragement, Cheerilee’s hooves speed up, firmly but gently jerking you off .
>She looks entertained by the sight of your manhood, squeezing, stretching, and twitching in her grasp.
>You hear her breaths become heavier, watching it intently as pleasure builds up inside you.
>Without thinking, you start running your fingers through her mane, stroking her on the back of the neck.
>”It feels good?”
>You nod.
“Feels really good. Getting a little close though…”
>”Can you do it more than once?”
>Cheerilee stares up at you coyly. “I want to see you cum…”
>Hearing those words while she eagerly milks your cock in her hooves makes your face flush with warmth.
“When you put it like that… I think I can keep going.”
>She looks pleased by your answer, turning her attention back to your throbbing dick, slipping her hooves along it faster and faster.
>You grip the back of her neck, stroking it to urge her onward, rubbing harder and faster when you feel your pleasure building.
>She reads you like a book, stimulating your sensitive shaft faster and faster, sending blissful sensations racing through you.
“Gonna cum…” You whisper in warning before inhaling deeply.
>Cheerilee leans back just as gobs of white erupt in thick pulses from your tip, spilling out sloppily, spurting onto cheerilee’s chest and cheek, then leaking out down your shaft.
>You let out a deep, satisfied breath.
“That was great…”
>”Fun for me too.” Cheerilee tells you as her hoof wipes off a pearly-white bead from her cheek.
>She casts a quick glance at you before closing her eyes and lapping it up from her dark fuschia hoof.
>”A little messy… but not too bad. Human boyfriends are a lot of fun.”
“Heh, yeah? Well there’s more where that came from.”
>”Mm, I bet there is… and we’ve got all night for it.”
“So what do you say, think we should take this to your bedroom?”
>She looks back over her shoulder. “Well… my bed’s actually a little small for you.”
>”So since we already made a bit of a mess… might as well go all the way, right?”
>You shrug and start pulling your shirt over your head.
“Might as well.”
>Cheerilee helps out by pulling your pants all the way off, letting them sit on the floor while you toss your shirt onto the pile.
>Now fully exposed, you watch as Cheerilee looks over your body with a satisfied smile.
>As you sit back, she climbs up to you on the couch, and puts her forelegs over your shoulders, meeting you face to face.
>You feel her tail gently tickling your sack as it sways side to side in anticipation.
>The teacher leans in to give you a deep kiss, pressing her finely furred chest to your firmly muscled torso.
>You stroke down her back with your palms, exploring her warm mouth with your tongue in a passionate embrace.
>She separates from you with a wet smack of her lips, and starts to slide her rump down, meeting your hardness with her soft groin as she gingerly positions you at the dripping crevice of her folds.
>The warmth of her nether lips kissing your tip sends a shudder through your body.
>”Good to go?”
>You nod and slide your hands down to her sides.
>She takes a breath and spreads out her hind legs, letting her hips drop down against you.
>Your head breaches her velvety folds effortlessly, sliding deeply into your marefriend as she lets out a shuddering breath.
>”O-oh my gosh… I needed this so bad.”
>Her walls throb, squeezing your dick and sucking it in deeper as her pleasantly warm mare pussy winks around you.
>You grab her by the flanks to hold her steady as you begin thrusting into her, drawing yourself halfway back and slamming your hips together hard in a steady rhythm.
>Cheerilee’s forelegs squeeze your shoulders tightly, pulling her close enough to let you feel her racing heartbeat.
>As you fuck the mare close and hard, you extend your thumbs to her flank and press them into the daisy patterns on her flank.
>”Oooh!” She moans sharply, her pussy squeezing down hard in a sudden rush of pleasure.
>Pleasure builds inside you as your thickness pistons her dripping cunt, and you start a pattern of teasing her sensitive markings, rubbing in slow circles on one side, then suddenly pressing down hard on the other, crossing wires in her brain and causing her eyes to roll back in blind pleasure.
>”Oh… oh my gosh faster please faster!”
>You eagerly oblige her begging, quickly pumping your shaft in and out of her sopping wet pussy as her warm chest presses against you hard.
>As you pound away, her needy walls cling around you with every thrust, filling you with growing bursts of pleasure as her breaths grow quick and short, her bliss beginning to reach its peak.
>”Inside…” is all she can breathlessly moan, driving her flank down in time with your thrusts to help you fuck her as deeply as you possibly can.
>Your hips hammer into her uncontrollably, bringing your ecstasy higher and higher…
>”Ah! Ahhh! AHHHH!” She cries out, throbbing around you and splashing thick droplets of marecum onto your crotch!
>Her box clamps you like a vice, greedily drawing you in and milking your cock in waves until you can’t hold back an eruption of ecstasy, spilling hot spurts of seed deep into her body!
>Your body tenses up as you spray her walls down with sticky whiteness over and over until her softness stops pulsing around you, giving you both a moment to rest.
>Cheerilee’s emerald eyes gaze lustfully at you through her mane, frizzy and unkempt from the force of your passionate lovemaking, letting out warm breaths against your neck as her mouth hangs open.
>”That was just… sublime…”
“You’re incredible, Cheerilee.”
>Cheerilee moans softly as she nuzzles your sweating chest. “Mmm… so are you. I just want to stay like this all night.”
“I wouldn’t stop you.”
>Cheerilee laughs lightly. “Cute, but we really should clean up at least a little bit.”
>”But… it isn’t a school night.”
>She snuggles the side of her face against your welcoming chest.
>”So maybe... a little longer wouldn’t hurt.”
“Yeah… maybe a little longer.”
>You stayed close to each other for quite a while longer...