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Dating the Teacher

By Tankris
Created: 30th August 2022 06:42:11 PM
2nd December 2022 12:13:35 AM

  1. You sneaked a peek at your watch for a few seconds. The bread sticks were getting cold and your glass was nearly empty. “Did...did she get cold hooves?” You muttered as your finger spun around the rim of your glass. As you pick it up to drain the last bit of soda into your mouth, you hear the front door open and spot her peeking into the restaurant. Her eyes meet yours and you see her cheeks darken to a deep red.
  2.  
  3. Miss Cheerilee was her name. A sweet mare who taught the local school kids for a living. She brushed a mulberry lock of hair from her eyes and offered a big smile as she walked over to your table. Her notable bust gently wobbled with every step and the sway of her motherly hips almost made you break into a sweat. Her attire was a simple button up blouse and a knee length skirt, yet it did little to hide the sweet rump or her soft belly. “Sorry I'm late. A teacher's work is never done, you know.” Her eyes scan the entire restaurant before taking a drink of water. “I'm sorry if I made you wait...I haven't been on a date in so long...”
  4.  
  5. You reach over the table and give her hand a quick squeeze. “Don't be nervous. All you need to do is have some fun while out to dinner. I think if you can manage being a teacher, this should be easy!” Your kind words brighten up her smile and she visibly relaxes. Her posture slouches ever so slightly, allowing a tiny sliver of chubby belly to peek out from under her shirt.
  6.  
  7. “So, tell me about working as a school teacher. Everyone always says teaching is easy, but I have my doubts.” Her eyes light up as you finish off your soda. “The children are a blessing but can sometimes be little devils in disguise. I wouldn't trade it for the world, though.” She giggles as the waitress approaches your table. “Decided on your order yet?”
  8.  
  9. Cheerilee peeks through the menu and sighs. “Just a light salad for me. No dressing, please.” You offer a questioning glance at her before speaking up. “That doesn't sound very fun. It's a night out, live a little and order something GOOD! I'll take a big slice of lasagna with a side salad.” Cheerilee bites her lip in worry as her eyes flicker down to the cute, chubby belly poking from her shirt. “I...um....” She stutters before letting out a defeated sigh. “How about...a plate of chicken parmesan and pasta along with that salad?” Her stomach rumbles in agreement, turning her face a deep red.
  10.  
  11. As the waitress walks away, Cheerilee places her face in her hands. “Gosh....You must think I'm a pig.” Your eyebrow raises in curiosity as she sits up straight. “I....I was late tonight because I had nothing to wear. The children are so sweet with their gifts and offer me so much candy.” Her eyes look back down as she gestures towards her chubby body. “It would crush their hearts if I didn't accept it and eat it...so I've gotten....gotten....fat.”
  12.  
  13. You quickly reach over and place your hands on hers. “Cheerilee, you are a BEAUTIFUL mare. Why else do you think I would have asked you out if I didn't think so?” Her eyes look away from you for a second before returning to your gaze. “I don't care if you're chubby. I think it makes you look cute.” Her embarrassment spreads across her face once more as you flatter her. “I'd even go on to say it makes you look SEXY.” You offer her a wink and a smile, noticing her breathing has quickened ever so slightly.
  14.  
  15. “You....you mean all that?” She asks. You look around for a second, then dive under the table. Cheerilee stiffens as she feels your lips pressed against the small sliver of purple belly peeking out from under her shirt. You hop back into place to see your date looking at you with a hint of concern and confusion. “Weh...well...I suppose if you think I look good...” Cheerilee smiles as she leans back into her chair. A little bit more of her belly oozes out of her shirt, attracting your attention instantly.
  16.  
  17. “Here you go! One lasagna platter and one chicken parmesan. Hope you two enjoy!” The waitress refilled your glasses and left you to your meal. You waited and watched as Cheerilee stared at her plate. “This...this is a HUGE serving!” She whimpered before looking over towards you. “I'd...LOVE to see you eat it all.” It's your turn to blush and squirm as her eyes widen at your claim.
  18.  
  19. Slowly, she cuts through a massive piece of moist chicken and places it in her mouth. Cheerilee chews slowly, savoring her meal before swallowing and taking another bite. Your fork dances around and misses your food, all attention focused on your date. She swirls up a bit of pasta and gulps it down before patting her slightly stuffed tummy. “This place is amazing! Such big portions and everything is so tasty. How's your lasagna?” She giggles, noting you haven't even touched your food.
  20.  
  21. “Oh..um...” You stutter before taking a big bite of your lasagna. The cheeky mare giggles as she resumes her meal. A bit of sauce smears on her cheeks as she eats, making you twitch under the table. Each bite is slower than the last as your date begins to struggle to finish the heavy serving of pasta on her plate. Cheerilee moans as she reclines in her seat, her not so small tummy bumping into the table. “Oh...oh Celestia...that was a lot...” She mutters as she begins to rub her belly.
  22.  
  23. Your eyes can't focus anywhere else but her gut. Oh, how much you would love to massage it for her. “Check, please.” You beg the waitress as she boxes up your uneaten lasagna. “Help me up? I think I seriously overdid it.” Cheerilee huffs as she daintily wipes off the pasta sauce from her face and tries her best to lean forward. You grip her hand and pull her up, shuddering as she presses her stuffed, bloated tummy into your stomach. Her hand grips yours and forces it down towards her plump, round rump as she giggles to herself. “I need all the support I can get. You made me eat all that food, you know.”
  24.  
  25. You stand in front of her house in the moonlight as she unlocks her front door. “I...I had a really nice time tonight.” She smiles as she leans in close, pressing her body against you once more. “I'd like to see you again soon. Call me, you hunky stud.” Cheerliee kisses you on the cheek and uses the opportunity to steal your lasagna right from your hands. “I think I'll hold onto this for you. In case I need a midnight snack.” She winks as she heads inside, rocking her plump hips and wide, jiggling booty through her door.
  26.  
  27. It's been a week since your first date and you've been sure to pamper Cheerilee in your absence. Constant flowers and candies at the schoolhouse, thick, fattening meals sent right to her door every night. You awaited at the local buffet in excitement for your second date, eager to see how she looked. A nearby clock chimed the late hour, signaling the beginning of your sexy stuffing session. You hear hoof steps approaching the corner along with some very labored panting. Your date finally arrives and your jaw hits the floor hard.
  28.  
  29. Her once soft, plump body was gone. In it's place was a jiggling, obese ocean of fat that never seemed to stop wobbling and quivering. Cheerilee seemed stuffed into her already huge looking clothing. A blouse that barely covered any of her massive cleavage and a skirt that showed off her flowing hips, giant rear and plump, thick thighs. She wiped a bit of sweat from her face and smiled at you. “Hey, handsome. Looking for me?”
  30.  
  31. The staff looked at Cheerilee with a weary eye as she waddled to your table. You had to fight back a grin as you noticed a few workers topping off the buffet even at such a late hour. Cheerilee's stomach growled with desire as the clashing smells teased her nose. “It all smells so good...and I haven't eaten anything all day. My poor tummy is just so hungry.” She gave her stomach a quick jiggle, straining the buttons of her blouse as she bounced and wobbled about.
  32.  
  33. Several plates of food were piled in front of her with an entire pitcher of soda to boot. Her tummy lets out another angry rumble as she begins stuffing herself. Her hands instantly fly towards the greasy barbeque and she digs in, smearing the sauce all over her face. You both suppress a shudder as she licks her lips in delight. “It was awful sweet of you to send me all those gifts, you know. I've been snacking and eating non stop because of you.” A greasy hand reaches up and gropes her breasts through her blouse, staining her shirt with an obvious hand print.
  34.  
  35. The buttons on her blouse whine and creak as she continues stuffing herself silly. More and more fat seems to droop over her chair as Cheerilee scoops up a cheesy serving of macaroni and shovels it into her mouth. Her overstuffed belly peeks out between the gaps of her blouse as it rises up to expose her navel. The fat mare giggles as she spots your erection threatening to tear out of your pants as you return with another few plates of food. “Excited? I know I am. Hand over that plate of pork chops.”
  36.  
  37. Empty plates were stacked up by the dozen as Cheerilee ate and ate, stuffing herself with more food that you had ever seen. Pork, beef, cheesy fries, fried chicken....anything and everything was crammed into her mouth and smeared all over her cheeks. The staff was barely keeping up with her pace, refilling the buffet constantly while trying to keep your table clean. Cheerilee moaned as she felt her stomach squish against the table. “I'm....I've still got room...I...I know I do...” She struggled as she tried to force another drumstick in her mouth.
  38.  
  39. Her navel peeked from under her blouse and her belly was set to rip apart the entire top. Her skirt dug into her soft hips as her rear and thighs were spilling and sagging over her chair. Cheerilee huffed and groaned as her gurgling belly tried its best to digest her mighty meal. “It's okay...you don't have to eat anymore just for me. You're so sexy already, baby.” You moaned, leaning in for a kiss. The smeared remains of her binging met your tongue, making the kiss messy and wet.
  40.  
  41. Cheerilee moaned before pushing you away and belching right into your face. You stared at her for a second or two before leaning down and burying your face into her exposed cleavage. “I...am gonna fuck you...SO HARD.” You mumbled into her soft flesh. Her chair gave a tiny creak of agony before snapping filled the air. Her quaking, over ripe body tore through the legs of the chair with her impossible weight, turning it into splinters. The unamused staff stared at your indecency while you continued to smother yourself in her overflowing rolls and fat.
  42.  
  43. Your hands sunk deep into Cheerilee's soft body as you eased her to your home. Every step made her body quake from her double chin, to her plump tits, her massive belly, huge ass and thick thighs. Her hips rocked and swayed as her booty dominated her frame, giving her the perfect pear shape even with so much food in her rounded tummy. Every grope of her chunky, doughy rump brought a lewd moan to her lips. “You naughty boy...feeling me up in public. You can't even wait till you undress me in bed, can you?” She teased as she bounced her hips into you.
  44.  
  45. Cheerilee was kissing and groping you right outside your door, leaving you to fumble with your lock blind. As soon as the key was turned, she pushed you through the door and dragged you along. “Bedroom. Where is your bedroom?” She begged and panted. Sweat was seeping into her blouse, further ruining her delicate attire. Cheerilee sighed in relief as she waddled into your bedroom and nearly slammed herself on top of your mattress.
  46.  
  47. Her clothing was peeled off her sweaty body piece by piece. Cheerilee sighed in relief as her thick, flabby body was finally free from her constrictive clothes. She rolled onto her tummy, pressing her flabby tits and sagging belly against your mattress. “So, is there something in your pants you wanna give me? Or are you gonna make me beg for it?” Your clothing flew to the floor as you dove towards her perfect body.
  48.  
  49. With speed you would have never imagined, Cheerilee pulled herself up, only to smash herself into you. Her warm, inviting belly smothered your crotch while her tits squished into your face. “Nah-uh. You're MY prize for tonight. I think I earned that nice, thick cock all to myself for being a good eater, don't you?” Her dirty talk only served to make you harder as you poked into one of her flabby, sweaty rolls.
  50.  
  51. “C'mon, then. You wanted to worship my body? Let's see that mouth and hands go to work!” She allowed your hands to slip free while she forced a fat nipple into your mouth. Moans and whimpers filled the air as you suckled her tit and sunk your hands deep into her doughy rump. “You...you asked me out on that first date...because of my big, bountiful booty, didn't you?” You moan in approval as you swatted her rump, forcing it to jiggle and bounce in your hands.
  52.  
  53. “You pervert. You fiend. Fattening me up and getting me all worked up like this.” Cheerilee moaned as she began grinding her body against yours. Her breasts smothered your face and blocked out the light as her tummy pressed harder against your cock. “Don't you dare cum. I wont be satisfied if you cum just to my belly.” Cheerilee teased as she pulled herself back up onto her legs. She gave you a squeeze with her meaty thighs before spinning around.
  54.  
  55. Her ass was inches from your face and yet so far. Oh how you longed to give each cheek a kiss before burying your face deep inside her butt crack. “Your cock is so twitchy and eager. Should I give you what you want? Or do I give myself what I want?” She teased before sliding herself away from your face and closer to your crotch. Her wet, needy sex pressed into your cock, making you both moan and shiver in delight. “I....take me...take all you want from me.” You moaned as you reached out and dug your fingers into her butt cheeks.
  56.  
  57. “Good. I'm hungry for one final thing tonight.” Cheerilee licked her lips as she inched herself up. Her thighs wobbled with the effort of pushing up her body, leaving her panting and sweaty as she hovered over your cock. Unable to hold herself up, Cheerilee plopped herself on top of you, moaning and shuddering as your cock filled up her tight, warm pussy.
  58.  
  59. “Oh YES...I've been craving this all week. Give it to me!” She moaned as she rocked her hips back and forth. Her big, fat ass clapped with every movement, making your hands slip and slide along her coat as sweat dripped from her body like a river. Her tired body forced itself up, just to crash back down on your crotch. The room was filled with lewd, wet slapping of sweaty skin clapping and bouncing as Cheerilee tried her best to keep a good pace.
  60.  
  61. “I...I can't” She panted out with ragged breath. “I'm so big and fat and out of shape because of you.” She moaned as you bucked your hips upwards and crashed into her massive rear. Her whole body wobbled for a few seconds until you pushed up once more. “Yeeessssss...fuck me...fuck me hard and make me jiggle.” Cheerilee begged as you picked up your pace.
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  63. Her ass never stopped jiggling and bouncing, clapping hard against your chest as you fucked her silly. Cheerilee shuddered and moaned harder and harder, her pussy clamping down and making it difficult to keep pumping. You pulled your hands up and struggled to find a good grip on her massive, sweaty hips and pulled her down hard. Even with so much resistance, you forced yourself deeper and deeper into her greedy pussy until you couldn't thrust any longer
  64.  
  65. With a roar, you pumped your cock as deep as you could and fired your cum deep inside her. Cheerilee moaned and screamed as she was brought to climax, making her whole body jiggle and wobble as hard as you've ever seen. Her body rose and deflated with every desperate gasp of air as you helped ease her to the bed. She leaned in close and immediately peppered your face with kisses. “That...that was amazing.” She smiled, pulling you close
  66.  
  67. Your arms wrapped around each other in a gentle hug. The teacher moaned in delight as you gently snuggled and jiggled her body around. “Mmmm. My big strong date. Keeping me full and satisfied.” Cheerilee cooed as she rubbed her thick thighs together. Her face went scarlet as she felt your hands groping her rear. “Should...should we cuddle like this or do you wanna be...the big spoon?”
  68.  
  69. You both giggled before she slowly rotated herself around, allowing you to grope her belly and breasts while your cock snuggled between her soft, bountiful butt. “Oh my...this is so lewd.” Cheerilee whimpered as she allowed your hands to roam all over her body. “I kinda like it.” She whispered as she pushed herself against you. You could already feel yourself hardening for another round and from the sweet moans coming from Cheerilee, you bet she would be MORE than willing to ride you once more.
  70.  
  71.  
  72. BONUS
  73.  
  74. “I haven't worn this in years...” Cheerilee giggled as she stepped into the bedroom. Your eyes lit up as she watched her outfit struggle to just keep her decent. A tiny top barely covered her tits, allowing her areole and nipples peek over the tops of her cups. Her massive belly was free to wobble and bounce as her shirt could barely server as a bra for the plump mare. A skirt so tiny and frail, it was torn just to fit along her plump hips. It didn't even cover her privates, leaving a pair of too tight panties to thread through her butt crack and right through her pussy.
  75.  
  76. “Do you like it? I WAS one of the best cheerleaders in my high school.” She smiled as she raised her pom poms into the air. The ribbon in her hair bounced along with every other flabby part of her body, making you moan in delight. “Well? Gonna show off one of those amazing cheers?” You teased. Cheerilee smiled as she kicked up a leg, flashing her pussy at you while forcing her entire body to jiggle and bounce against itself.
  77.  
  78. “Who's the best mare in town? I AM!” She shouted, pumping her arms up and sending her tits jumping. “Who's the hottest stud in town? YOU ARE!” She cheered, popping out her rump and giving it a healthy shake. “Who demolishes all the buffets? I DO!” Another hop sent her breasts flying out of her top, forcing them to bounce and jiggle free in plain sight.
  79.  
  80. Sweat dripped from her head and from her body, soaking into the outfit and saturating it. She gave one final kick that tore through her skirt and forced it to flutter to the ground. Her body was heaving as she struggled to catch her breath. “How...how...was that?” She asked. You stood up and pressed yourself against her, kissing her deeply while allowing your hard cock to grind against her. “Bed....bed now!” You demanded, not even bothering to strip her of her remaining clothing before mounting her fatty rump.

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