>You are Anon
>Years ago, you ended up in Equestria by pressing Esc to exit full screen mode
>Since then, you've built a circle of friends, a career and a family here
>That last one was the cause of the letter you were holding
>Written by Ms. Cheerilee, it asked if you could meet her after school tomorrow
>Just a routine teacher-to-parent talk, nothing to worry about
>Sounded fine
>You didn't really care for the finer details of Equestrian education, but the few times you'd seen Cheerilee she was very nice and welcoming
>She seemed like a friendly pony and a good teacher

>It's afternoon now
>You put away the newspaper and take a look at the clock whilst sipping your coffee
>Half past three, time to head towards the school house
>Luckily it's a relatively short walk, around ten minutes from your house
>Once you get there, you knock on the wooden door
>"Come in!" you hear that familiar, comforting voice from inside
>Promptly, you swing the door open and step inside
>Cheerilee's sitting behind her desk in a rather comfortable looking chair
>"Hello Mr. Anon, good to have you here. Please, have a seat."
>You do as you're asked and take place across Cheerilee
>She leans forward to extend her hoof to you, which looks like it's taking a good amount of effort
>Her chair creaks loudly as she does so
>You shake her hoof, but it's difficult to maintain eye contact
>Her shoulder is covered in thick layers of fat
>And indeed, she seems to have acquired two more chins since the last time you met her

>"Would you perhaps like some coffee, Mr. Anon?"
>Shit, that silence was probably a bit too long
>Gotta keep your focus
"Sure, thank you."
>"Maybe some cake too, to go with it?"
>Cheerilee gestures over to an opened box, containing a half-eaten cake
"Yes please, that looks delicious."
>"Oh trust me, it is", the teacher says, followed by a warm, good-natured laugh
>For some reason, you don't doubt her statement for a second
"So how have things been here?" you ask
>"It's been great, thank you for asking! All students have been doing very well, and I've really gotten a connection with the class."
>She beams with that happy expression of hers
"That doesn't surprise me. With a lovely teacher like yourself, even the most annoying of kids would calm down and pay attention."
>Maybe that one came out a bit too cheesy
>Cheerilee blushes and thanks you for the compliment, then moves on
>You talk to her about what kind of subject material will be talked about in the coming few months
>The conversation itself is rather uninteresting, but the purple mare's enthousiasm and the cheer in her voice keep you paying close attention
>Not to forget the way you scan her voluptuous body whenever she gestures with her hooves

>After a while, you have the opportunity to ask her some questions
>Because you don't know how high school et cetera works here, you ask Cheerilee about it, and she's happy to explain
>It really gets worth the effort when she stands up and sketches some of the different levels of education out on the chalkboard
>Her belly hangs against her hindlegs when she leans forward in order to visualize her words
>Her hips, too, are comfortably sized
>You can only imagine how she'd look during gymnastics class

>Sadly, the school system in Equestria isn't grossly overcomplicated like it was in some countries on Earth
>After just a minute or two, Cheerilee's scribbled everything down, ans she returns to her chair
>Again, her seat lets out a noise that would leave you to question it's quality, if not for the size of the pony lounging in it
>The teacher cuts herself a second slice of cake, and another one a few minutes later
>She's chewing most of the time when you talk to her

>As the conversation goes on, you completely lose yourself in admiring the purple mare's overweight figure
>It is for this reason that you have a nasty shock when a cleaner peeks his head around the door, asking if you and Cheerilee could please clear the classroom
>The mare turns to you, and asks whether you know enough or want to continue the conversation at her house
>You decide that you want to know a lot more about Cheerilee and choose the latter
>Together, you pack her stuff and get ready to leave the building
>Like the true gentleman you are, you pick up her bag and carry it for her
>The fat pony puts a hoof on your back and leans into you in a token of gratitude
>Five minutes later, you both arrive at a small cottage that's as friendly and nice-looking as its resident
>After making coffee, Cheerilee comes back from her kitchen with a plate full of donuts to share
>She places it down on the table and hoofs you one, then takes one for herself and leans back onto her couch
>"I hope you won't mind if I get comfortable?" she asks
"By all means, go ahead. It's your home, after all."
>She laughs, and lays herself down onto the couch, her belly spilling over to rest on the cushion in front of her
>She then continues to enjoy her coffee and snack
>The view is nothing short of breathtaking
>Her hindlegs lay crossed, giving away a peek of the pony's massive flank
>Once again, it's quite the achievement that you manage to look her in the eyes

>It doesn't take long before your talk is about your personal lives instead of that boring old school system
>Cheerilee talks about what she likes doing in her spare time, and unsurprisingly, eating out with friends and baking all kinds of goods are on the list
>She steadily eats through her donut in the meantime
>Before long, her sugary confection is finished
>The teacher looks at her empty hoof in a mock sadness
>"Eh, Anon, could you please hand me another donut? It seems I've run out" she says, followed by a smile
>You laugh, and get up to take another donut from the plate
>You decide to grab one covered in chocolate sprinkles, which looks absolutely delightful
>And it seems you're not the only one who thought so
>"Oh, Anon, I was hoping you'd take that one. Chocolate donuts have to be my favorite."
>You sit on the front edge of the couch and give Cheerilee her food
>Then, you put your hand on her belly, and when no complaints follow, start slowly rubbing across the expansive form of her chub
>"Mmmmhhh..." the gluttony mare moans quietly when she takes a bite
>You extend your rubs to include the pony's giant flank, and carefully reach around a few times to grope her ass
>This continues until this donut, too, has disappeared from Cheerilee's hoof
>The mare's eyes are half-lidded as she licks her lips, collecting the last bits on chocolate in an incredibly sensual way
>She puts her hoof on your leg and lets it travel up to your side
>This is the moment
>You lean into her embrace, and kiss her
>She smells sweet, like sugar and frosting

>Before you even dare to think about it, the pony's tongue comes pushing between your lips
>The taste of chocolate comes with it, and you welcome it into your mouth
>Cheerilee starts rubbing your back with her hoof, and you do the same, starting at her shoulder
>Slowly, you work your way down her side, your hand curving with her round and squishy body
>The feeling of her super soft and warm fat turns you on immensely
>You repeatedly pinch her doughy layers of fat carefully
>Once you can't reach any further down her legs, you slowly start turning inwards
>Your passionate kissing continues as you do so, which you take as a sign of approval
>Your fingers caress the chub on the inside of her large thigh
>Eventually, you reach her nether regions, which are steaming hot
>You feel Cheerilee gasp when you touch her clit
>Gently, you rub it, then move on to the obese pony's marehood
>Your hand slides between her fat lower lips, and it's engulfed in her warm fluids
>After some more teasing, you bend three fingers and shove them inside her
>And holy shit is she wet
>Not to be outdone, Cheerilee starts caressing your crotch
>Her hips begin to slowly rock back and forth, pushing her body into your hand

>You break the kiss, and start moving down her massive body, kissing every inch of it as you go
>Once you end up between her legs, you put your hands on either flank and lean in to tease her clit with your tongue
>Stimulated by her juices running over your chin, you lick it in all possible directions
>Sometimes you suck lightly on it, other times you circle around it multiple times before touching it again
>Moving down, your entire face is covered in hot fluids from the obese mare
>She moans quite loudly as you eat her out, putting pressure on every last fleshy bit of her vagina
>But all good things must come to an end, in this case to make place for other good things
>You unzip your pants and pull them down, along with your shorts
>Your dick finally has the space to stand fully erect
>Cheerilee leans forward, and carefully licks the tip of your boner
>Slowly but surely, she works her way down before she starts sucking it
>Then, she suddenly takes all of it in her mouth, without a single problem
>The sudden warmth is incredibly pleasing
>She starts bobbing her head back and fourth, blowing you with all her passion

>You return to playing with Cheerilee's clit once more, and it's clear that this is greatly appreciated
>Finally, you pull away from her mouth, and position yourself between her hindlegs once more
>You drag your cock down from her belly over to her pussy, and slowly insert yourself
>The mare was even softer on the inside than on the outside
>Her hot cunt was tight yet impossibly soft
>It wrapped itself around your dick perfectly
>You gently start thrusting back and forth, causing Cheerilee's belly to sway back and forth with the rest of her beautifully plump body
>Once you pick up some speed, the many excess layers of fat located all over her body jiggle and bounce whenever you ram yourself into her
>The lovely, overweight pony's breath goes from loud, to heavy, to continuous moaning and gasping
>You slam into her fat pussy over and over, hilting your entire length into its soft folds time and time again
>When you start coming close to your peak, Cheerilee cums, and washes your enitre crotch in her sticky mare cum
>"Anoooooonnnnnn...~" she moans
>You speed up one last time, racing towards the point of no return
>You can feel it coming closer
>You look at her firm thighs, her round hips and her squishy belly, all of them shaking back and forth heavily from your pounding
>When you feel you're ready, you slam into her soft pussy, and blow your load deep inside of her