Chapter 1: Homework for Pinkie Pie
Author's Note
Fetishes: Nonconsensual, Sperm Swallowing, Vaginal Sex, Greasy Sex, Shemale on Female Sex
Chapter 1: Homework for Pinkie Pie
Twilight Sparkle's horn glowed as she pulled new books down from the shelf laying them out on her desk two at a time. She closed the book she was currently studying, a rare discourse on mental magic, and moved her hands across its cover one last time before setting it aside to make room for the two new ones. Some ponies might have found the task difficult, but she was determined to craft a new spell for Celestia. Something along the lines of her want it, need it spell. Something not as blunt. Something more subtle.
Twilight's studies were interrupted by a loud, excited rapping at her front door. She opened the top half with a flick of her horn. Pinkie Pie fell forward as the door opened, tumbling over the waist-high hurdle of the door's lower half and coming to a rest on her head, ass in the air.
"TWILIGHT!" she screamed, her voice shrill and excited.
"Yes, Pinkie?" asked Twilight, eyes rolling as she clopped over to help her friend right herself.
Once Pinkie was upright she asked, "Guess who got invited to go on the most stupendous, super duper, awesome trip to Canterlot?" From the wide grin on her face, the answer was clear.
"Was it you by any chance?" asked Twilight, smiling and dusting off Pinkie's shoulders.
"YESSS, YESS, how did you know? Did someone tell you? It's supposed to be a secret. I mean, it is a secret. Or it was a secret, but I guess it's still a secret if you don't tell anypony."
Twilight trotted back to her books, "Princess Celestia has commissioned me for a special spell. Maybe this has something to do with it, but if it's supposed to be a SECRET, Pinkie, then you shouldn't be telling me about it!" She looked over her shoulder to check for Spike, but he was still upstairs snoozing late into the day. "But I suppose you've already spilled most of the beans to me. I won't share your secret with anypony if you give me all the juicy details."
Pinkie bounced in place, springy on her hooves, and nearly touching the ceiling with her hands. Pinkie seemed to defy gravity unlike any other pony in Ponyville. "Aweeessommmeee, but you gotta Pinkie Pie swear with me."
Twilight let out an exasperated sigh. Pinkie could be insufferable sometimes, but at least she meant well. Twilight went through the motions, even jamming her curled up fist into her eye. "...stick a cupcake in my eye. Pinkie, why does your swear even involve this. It makes no sense!"
Pinkie just smiled as she removed her own balled up fist from her eye socket. It didn't hurt, but she had once given herself a black eye during an especially exciting Pinkie Pie swear. "It makes total sense Twilight. It's like, uh, you know, a test! You gotta pass it. And I'll know if you don't. So, like, Celestia told me she needed some help trying out some new training techniques for mares. Said I'd be her very first volunteer. I'm super excited to help, and it never hurts to help, right?"
Twilight snickered as she sat down on the pillow she used for a chair, "Well I don't know if that's one hundred percent accurate Pinkie, sometimes it can hurt to help! What with all the encounters we've had to face over the past couple of years I've gotten my share of bruises. Did Celestia give you any more details than that? Sounds a little vague."
Pinkie shook her head, long mane brushing along her shoulders as she did, "She just said it was really important, and that I'd be part of something that would affect all of Equestria. I mean, I know I'm special, but soon I'll be super-special. Maybbeee I'll be a PRINCESSS!" she squealed at the top of her lungs, stamping her hooves. "Or it could be super boring and lame like the Gala, but that's not very exciting, so I'm just gonna assume it's gonna be awesome."
Twilight smiled, "I'm very happy for you Pinkie. I'm sure you'll have a great time. Do you know how long you'll be gone? And do you need someone to take care of Gummy? I hope you've made a list of everything to do before you go. It's very important to stay organized."
Pinkie bounced in place, "Celestia said I could be there anywhere from a few days to a few months. I guess it depends on how well the training goes. Maybe when I come back I'll have super powers. Or know magic! I could be the first earth pony with magic. Wouldn't that be awesome??? But, um, Guppy's staying with Fluttershy, and I've got everything packed already. Candy, party supplies, rubber chickens, more candy, and, uh, lots of other stuff."
Twilight stood up, looking down at her books, "Thanks for coming over Pinkie, I'm glad you told me, even if it was a secret. I promise not to tell anypony else, but you have to remember to write if Celestia needs you for longer than a week. Even if it is just party invites and glitter pen." she winked, gave Pinkie's muzzle a friendly nuzzle, and then bit her lower lip, "But I'm going to have to ask you to leave. I really need to get back to my research that new spell. Celestia said she'd need it sooner rather than later."
Pinkie stopped bouncing, if only for a moment, to nuzzle Twilight right back, "Thanks Twilight, I'll make sure to bring lots of cool stuff back from Canterlot, and write when I can. Byeeeee!"
With that Twilight returned to her studies, and Pinkie returned home to put the finishing touches on her packing. After stuffing one last collection of deflated party balloons into her already overflowing suitcase, Pinkie trotted to the Friendship Express, luggage in tow. Soon enough she was on the train, heading straight to Canterlot which was about a day's trip away. Pinkie felt right at home with the gentle rocking of the train and the chatter of the passengers. To Pinkie, a train ride was akin to a low-grade party. She moved from passenger to passenger introducing herself along the way and making bubbly chatter. Most ponies knew of Pinkie pie from her involvement in the defending Equestria as one of the Elements of Harmony, so not only was it easy to make friends, but it also wasn't strange when, after departing from the main carriage to head back to her room, she ran into someone who already knew her name.
Tala Tearjerker had dirty blonde hair with highlights of lighter colors both in her mane and in her tail. Her eyes were a dark blue, and she stood just under six feet tall. Her dress was a rich red and made of a single piece of fabric. A deep cut circle showed off Tala's heavy cleavage without threatening any real nudity. Two slits along the sides of the dress ran from just below Tala's hip and exposed her long white legs. The dress was provocative for day wear. Surely Tala would turn heads. Rarity would most definitely have approved. The mare smiled as Pinkie approached her cabin, "Pinkie Pie I presume? Celestia sent me ahead as an escort to make sure that you made it to Canterlot. I meant to catch you on the platform, but I lost you in the shuffle."
Pinkie Pie giggled. "How'd you know it was me, huh? Was it my bubbling personality? Or maybe my extra-floofy mane?" She pushed hers up for effect, letting it spill back down over her shoulders.
Tala just smiled, "You're neon pink, and stand out like a sore thumb. Honestly I didn't even need a proper description to spot you." She tapped on the clouded glass to Pinkie's compartment, "I hope you don't mind me imposing on you for some space. Celestia sent me packing with a ticket for coach." She sighed dramatically. "Free travel is just one of the perks of being a servant of the government, but they only provide the cheapest accommodations. My name is Tala by the way, Tala Tearjerker. I make mares cry."
Pinkie nodded, "Of course you can! And we can talk. Celestia hasn't told me much. I was really hoping, like, uh, you could let me know more" she leaned in really close "unless, it's too super-secret to even talk about on the train? I mean, I totally haven't told anypony, and I never would."
Tala opened the door for them, leading Pinkie into her own compartment. It was spacious, with a double bunk bed along the left wall, and a place to sit on the right. The space between the walls gave a pony enough room to stretch fully without feeling cramped. "Well, Pinkie, I'm mostly here as a guide," Tala explained, ushering the pink pony inside, and locking the door behind them. Tala looked out through the glass to make sure nobody was on the other side before pulling down the blinder for the window. The glass was already opaque, but she wanted complete privacy. "To make sure you arrive on time, and in good shape for your lessons. Celestia will give you the full explanation when you arrive. I really wouldn't want to speak for her in that capacity." She took a seat next to Pinkie, stretching an arm out over the back of the cushioned couch, and settling it across Pinkie's shoulders.
Pinkie wriggled excitedly into her seat, tail flickering over the leather of the cushion. Being in the compartment with Tala felt top secret and very special. Pinkie could imagine that she was she was a spy smuggling herself into a foreign land to help save all of Equestria. "That's okay! I understand. The other mares usually don't explain stuff to me either. They always just expect me to know! Like, how this one tim-."
Tala smiled, interrupting Pinkie with a finger to the pink pony's lips. "There is one thing I can tell you about the lessons Pinkie, and that's that they're sexual in nature. I know that sounds a little strange, but stay with me here." Pinkie giggled, blushing a little, and wrinkling up her nose at the word, "Sexu-" she squeaked before Tala shhhed her one more time, "And while I'm not qualified to give the lessons myself, I have a little prep work for you, something you'll need to finish off before we get to Canterlot. It'll help open you up for new lessons." She reached across herself, taking Pinke's left hand with her own, and settling it on something between her legs. Pinkie felt something thick, and heavy, pulsing slightly with each beat of Tala's heart. Tala's eyes were calm, and placid, while Pinkie's opened wide in surprise.
Pinkie's hand squeezed down around the thickness that she felt. The mare was no innocent, but shemales, mares with pricks instead of pussies, were not common. She hadn't even seen one before now. As Tala's heart thudded a little harder, the thickness between Pinkie's delicate fingers grew. "Oh, jeeze, you're a special-pony." she said, her voice low, her hand trembling a little. "I've never been with a special-pony. Is this my homework?" she asked, the blush fading from her cheek. She bit her lower lip, running her fingers along the length of Tala's shemale horse cock, feeling the bulge of the medial ring, and flared tip. "Are we gonna, uh, like, do it?"
Tala snuggled in a bit closer to Pinkie, letting her legs fall apart and giving the pure mare easier access. The dress did little to hide Tala's endowment, outlining her stallionhood as it draped across its thickness. "No quite, Pinkie. When mares do it with stallions, there's a choice right? Sometimes they do it, sometimes they don't. Well this is an important bit of prework for your lessons, and if you're interested in helping Celestia, which I know you are, then you don't have a choice. So we're not really going to do it, Pinkie." Tala explained carefully, gently pulling the single strip of fabric lying between her legs to the side, revealing the long, pink length of her glistening cock. Tala's shaft bobbed upwards, and Pinkie's hand pulled away for a moment as if the thing might bite her, before Tala gently guided it back, clasping her digits around Pinkie's own, moving her wrist in a slow stroke back and forth to get the pink pony used to the idea of her size and girth. "We're not going to do it because I'm going to rape you." She stood up, shuffling over in front of Pinkie while her prick bobbed in mid air, thick and hard enough to stay level with the ground and keep her dress pulled out of the way. The musk of her naked maleness filled the room, and precum pearled from the tip of her oily prick.
Pinkie's blush returned when Tala said the word rape. That couldn't be right could it. Rape wasn't a good thing, and Tala was here on a mission from Celestia. Something clashed in her mind, but Pinkie resolved to see things Tala's way. She must be doing this for the right reasons, after all. Pinke's hand jogged along Tala's cock a moment more before the mare stood, and with the fleshy thing facing her, bobbing, she nodded, "Oh, oh okay! I guess that makes sense. I haven't been raped before, though, so could you like, uh, go nice and slow? You're kind a big stallion, er, mare, er, pony." She giggled a little bit, and reached down, digging into her open suitcase and pulling out a balloon. Ever the party pony, Pinkie had had to improve before and she knew just what to fetch, "Could you put this on, Tala? If you're gonna rape me I don't want to get pregnant."
Tala looked down at Pinkie with hungry eyes. The mare's bosom wasn't as large as Tala's, but with all those extra sweets she snacked on at the candy store, they had an extra layer of heft that the other mares didn't. Pinkie's ass had a similar softness to it that kept her cheeks thick and jiggling. Tala's gaze drifted to the makeshift condom, and for a tense moment she waited considering. Pinkie felt a chill of fear run up her spine. Was Tala going to fuck her without a condom? Was she going to get pregnant? But with a late smile, Tala took the balloon from Pinkie's hand, and worked it down the long, pink length of her cock. "Of course, Pinkie. Don't want you carrying foals you can't handle." It didn't fit all the way over her shaft like a proper rubber would have, but it would provide a moderate amount of protection. With her prick covered Tala knelt between Pinkie's thighs and ran her hands up the mare's short skirt pushing it over the top of her thighs. "These are very pretty Pinkie Pie. Pink and blue. A little clashy, but still nice." Tala ran her hand down the front of Pinkie's panties, feeling her through them. "Let's get these off you, and then we can get down to your homework, okay?"
Pinkie smiled when Tala took the condom. The tension went out of her like the air out of a party balloon. She noticeably relaxed, smiling wider at Tala's compliment to her panties. "Thanks! Rarity made these for me. She's really good at that sort of thing. They could use more streamers, but she wouldn't add them," she hrrumpfed, and then arched her back a little while grinding herself up against Tala's open palm. She rocked firmly against Tala's touch, gyrating her hips back and forth, lifting up off the couch a little as Tala palmed her cunt. "Oh-o-oh-okay, sure thing Tala." She shifted upwards, lifting her ass completely off of the leather seat, and pulled her panties down her thighs. The soft lace clung to her sticky cunny, pulling from her plump, engorged lips so that the center of panties came away last.
Tala helped Pinkie with the next step, lifting those panties up, drawing Pinkie's legs into the air as well. She didn't remove them completely though. Instead she left them in place around Pinkie's ankles. The poor mare couldn't help but feel even more exposed with the panties around her ankles making it difficult for her to move her legs. If she needed to escape it would be difficult at best. Tala lowered herself into position, grasping the base of her monster cock, and squeezed it, which filled the tip of the balloon with salty precum. Tala nestled her flare up against Pinkie's naked pussy while using one hand to keep Pinkie's legs straight up in the air which mashed them up against Pinkie's tits and kept her pinned against the seat. "Rarity does have an excellent eye for fashion. I'll have to mention that to Celestia." she rocked firmly, brushing her rubber coated flared across the lips of Pinkie's vulva. "I'm going to rape you now, Pinkie. Just try to relax, okay? I can't promise it'll feel good, but that's how hard work is, it doesn't always feel good." And with that, Tala leaned forward, and bore her weight down on Pinkie's tight little puss, the broad flare of her shaft overwhelming the mare's soft slit, and grinding on it harshly.
Pinkie's hands spread out to either side of her body to provide stability by openhandedly grasping the couch. Her nails dug into the smooth leather as Tala's cock brushed against her naked slit, "Oh, oh geeze, you're realllly big Tala. Are you sure you can fit? M-m-m-maybe I could just let you rape my hand!" she offered, before throwing her head back in a squeal of pain, hands clenching hard, as Tala' prick found purchase. It wasn't much, as Pinkie was very tight, but Tala knew just what to do. She was a practiced rapist and she put her skills to good use, sinking her cock deeper, pumping her hips in short little strokes so that Pinkie's pussy radiated waves of agony mixed with tiny bursts of pleasure as Tala's cock hammered into her a few inches at a time. In and out, in and out, Pinkie's cunny spread wider and wider, opening up for Tala. Pinkie cried out a second time when Tala's medial ring nestled up against her cuntlips. Tears wet the edges of Pinkie's eyes, "Ahh, ahhh, it hurts, it hurts pretty bad, Tala. Are-aa-a-aare you sure we gotta do this?"
Tala widened her stance to make it easier to get pressure on Pinkie's exposed pussy. Her hips moved slowly, but with purpose, practiced movements that pushed Pinkie's tight little cunny wider, allowing her balloon clad cock to dig deeper inside. Each time she hunched her hips forward she sunk a little deeper, forcing Pinkie to accept her party-balloon-clad package. "Oh yes, yes we do. Celestia gave me very specific instructions on when and how to rape you, Pinkie. We're getting there. You just got a foot more to go, and then I can cum, but not before I hilt, okay? It's really important I be inside allll the way." She leaned down, brushing her tits against the back of Pinkie's legs rolling her hips in sharp bucks, and pushing her medial ring right on in, "Almost there, Pinkie, hang on for me. It's okay if you gotta cry or sob, but if you need to scream, just lemme know." And with that, Tala pushed even deeper. The balloon covered part of her shaft disappeared completely into Pinkie's pussy, and her big balls finally clapped against Pinkie's upturned ass. Tala's balls were naked and glistening with sweat. They left behind gossamer stands of sexual grease as they peeled away after each thrust.
Pinkie's body arched up off the cushions, and her arms supported her as she tried to squirm away from Tala's deep penetration. Pinkie tried to pull back to give the stretched out tunnel of her sex some relief, but Tala set two hands on her shoulders and planted her firmly back down into the seat, which helped her sink a few more inches of glossy pony prick into Pinkie's tensing maresex. Pinkie's lips trembled and she lets out a hot, heavy sob with tears streaking her cheeks in wet rivers of pain. Her cunny tightened each time Tala pushed inside which just made the pain worse. Pinkie begged so sweetly, "P-p-p-p-pleassee stop, T-t-tala! It reallly hurts!" But Tala was undeterred, her hips moving at a steady pace. Pinkie's sobs got louder, and a scream caught in her throat when Tala's fat, balloon covered flare mashed up against her cervix. Her throat contracted as she swallowed the cry of pain, but then another one arose moments later.
But Tala was right there, hand clasped over Pinkie's mouth, drowning out her scream into her palm, muffling it so that no one else could hear. Sure it was part of Pinkie's lesson, but the other ponies wouldn't understand, not yet at least, and things had to be kept confidential. Tala panted hard as she sank in the last few inches. Her sheath rim mashed up against Pinkie's abused cuntlips, spreading her vulva all the way open, while her balls stuck to Pinkie's upturned ass, jelling against her chubby rear. "Here we go, Pinkie. Gonna, nggh, gonna nut." she hunched her hips forward, not really thrusting, just grinding against Pinkie's sex, as if she could bore deeper by doing so. Her cock stirred around in the poor pony girl while Pinkie's hands moved off the couch and squeezed at Tala's hips, pushing this way and that in a frantic effort to dislodge the big shemale cock probing the depths of her sex. However, it was far too late for any kind of resistance. Tala's sack pulled upwards, her shaft swelled, and as her prick bulged with waves of semen, her nuts tensed with each squirt. Her sperm didn't wash right up into Pinkie's womb as would have been proper, but instead filled out the balloon, expanding it into Pinkie's pussy, and sending plenty of her orgasm rushing back out around Tala's prick.
Pinkie's nails scraped along Tala's thighs as her cunny was violated by the hot sperm of the shemale stud. Pinkie expanded her compact form by pushing backwards on Tala with her legs in order to give her belly room to grow as the thick waves of shemale sperm rushed up into her. She gasped into Tala's hand and then went lax. The worst of the ordeal was over, and getting cummed into was a rather passive activity. She slumped back into the couch, legs framing Tala's face as the shemale crooned in pleasure. Her pussy squeezed out of pure reflex, drawing the juices in the balloon deeper, and bulging it in her gut. She worried about the sheer size of Tala's load, but the balloon held, and Pinkie mumbled through Tala's hand, "I bont sceem agun, pomuss!"
Tala relaxed atop her charge and reached up to pull Pinkie's panties the rest of the way off. Tala discarded Pinkie's panties with a flick of her wrist. With the deed done she no longer needed the makeshift hobble. Tala settled in, sweaty frame pressed against Pinkie's own, to let the heavy tension drain from her sack. The special treatments she had been getting were making her antsy, and the only way to scratch the itch was to dump her load. There were plenty of ways to achieve that, but squirting it into a mare was always the most satisfying. She'd feel the relief of a well drained sack for the next day. "I know you won't Pinkie, you're a real trooper." she unclasped her hand around Pinkie's mouth, and leaned in, brushing her white muzzle in close nuzzling affectionately after giving Pinkie her first bit of homework. Tala's dick pulsed and shot out the last of her juices, sack sagging back down.
Pinkie worked her jaw, and smiled up at Tala. It was a reserved thing, a little shy, especially for Pinkie Pie. "Did I do okay? I've never been raped before today. I hope I passed and everything! It hurt pretty bad at the end, and, uh, the middle too, and the beginning. Well, pretty much the entire time! You're bigger than Big Mac." she said, giving Tala's exposed flank a squeeze on either side.
Tala just smiled, and kissed Pinkie's lips, her cock starting to soften inside of the mare's well stretched cunt. "You did fine, Pinkie. You're an A+ student. I'm sure Celestia will enjoy teaching you as much as I have." She slowly pulled back, wincing at the sensations of her sensitive flare dragging along the inside of Pinkie's twitching cunt. Tala stepped back slowly and pulled her glistening pink prick from Pinkie's twat which burbled as semen spilled backwards along her cock. The thick stuff emptied from the back channel of the balloon covering her prick, but Tala squeezed it at the neck, stopping the flow. She pulled completely free with a flourish, cock bobbing upwards, and then sagging back down at the sheer weight of all her sperm trapped at the tip of the inflated balloon. "We're going to have to do something with this, Pinkie. I'm not used to wearing any kind of protection. Especially not with a mare." Tala's words sounded sharp, as if angry that her prick was covered by anything at all, but it was only a moment, a fleeting glimpse of a razor's edge, and Pinkie didn't seem to notice.
Pinkie moaned softly as Tala's prick emerged from her cunt. It actually felt good, like exercising a sore leg. Sure it hurt a little, but nothing like the insertion. She could almost get off on the sensation of her cunny closing back up, and when Tala's prick finally sloughed free of her snatch, Pinkie felt a certain emptiness inside. The sensation of loss only lasted for a few moment, but it was powerful. Pinkie sat backwards on the couch and wiped away the tears from her eyes. "Well I can show you what I always do when there's leftovers." Pinkie's voice was crisp and chipper despite the redness of her tearful eyes, and the pain of the recent rape.
Tala pinched the balloon off the end of her cock, letting it weigh heavily in her hand. Her prick, finally softened, began to retreat back into its sheath. Though Tala's spongy cock flesh was still wet with sexual fluids she didn't seem to mind at all, pulling her dress back into place with her free hand and just letting things sort themselves out. She handed Pinkie the balloon pinched at the neck. The balloon was swollen heavy enough that the PARTY HARDY! text on it was clearly visible. "Please, Pinkie. I'd love to see what you know. I'll make sure to tell Celestia, so that she can know where you're starting at."
Pinkie took the balloon in both hands. In one hand she pinched the balloon's neck, and in the other she palmed its weight from below. "Applejack taught me this one. She's always saying waste not, want not." Pinkie tipped the balloon towards her mouth, and opened her lips. She grinned before relaxing her grip around the neck of the balloon, and letting the thick, hot, shemale sperm roll down her tongue. Pinkie held her tongue outwards to form a channel for the sperm which slowly rolled down the back of her throat. She just let it go, gulping on occasion when the buildup in her mouth became too much, and swallowed all of Tala's spunk till the balloon deflated to the point where she could hold it. Then she squeezed the party balloon from the base and rolled her digits up its length, squishing out the last of Tala's sperm right into her mouth. "Kind of tastes like plastic. Really salty plastic!".
Tala grinning as Pinkie sucked her sperm from the balloon. It was an exquisite display, and Tala's cock thudded a little harder for it, before finally surrendering to the softness of a post coital bliss. "That's very nice Pinkie. I'm glad that you know just what to do with a heavy load." Tala sat back down next to Pinkie, and handed the mare her panties. "I'll be sleeping here tonight, Pinkie. You can pick the bunk you'd like." she winked with a smile. "Try to get some sleep. Tomorrow's going to be a long day."
