Anon has noticed something very odd with the ponies of Equestria, or at least with the mares of this fantastical world of magical talking equines that have distinctly alluring bodily features that, while on paper seem strange for an equine to have, are actually quite tempting. For example while the ponies of this world on measure are three feet in height while on all fours, and have rather stout short bodies, the mares have quite luscious round flanks that look so soft to grope.
Aside from their flanks mare’s also have quite unique genitals, with their sphincter looking like any equines back on earth, but their marehoods look like a cross between an equines and a humans, being fairly famine yet also quite plump. It’s actually quite amazing that Anon doesn’t see more stallions with raging boners around Ponyville, since their able to get full on shows just being walking around, or even standing behind mares while waiting in lines. Not to say he hasn’t seen stallions with full erections, but with their short and stout bodies, a stallions cock is actually quite small. At first he thought they’d be huge, at least as long as their whole barrel, but with ponies being so short and stout in their overall bodily builds, if stallions did have massive earth horse cocks they’d quite literally skewer any mare they try to fuck. With their full lengths piercing through the mares pussies, womb, and right into their stomach lining.
But going back to mares and what Anon has finally noticed, after observing them, they all seem to have varying degrees of teat sizes. Like woman with different breast sizes back on earth, which seems a little odd. Especially for a quadrupedal creature. Since ponies walk around, unless you’re a pegasus and you can just fly, having any mammary glands bigger than the flattest of A-cup size mounds, would be rather uncomfortable to walk around with. After all the mare’s back legs would constantly squish and rub their mounds together, and against their legs that it would probably get VERY uncomfortable for a mare to walk for more than a minute, before their teats start to feel sore and raw from the constant back and forth rubbing.
And yet, Anon is currently sitting at a table at Sugarcube Corner pony watching, and seeing mares with varying teat sizes walk around without being burden or hindered. Granted most of the more larger teat sized mares walked with a strange gate, some having their back legs spread out a bit more than usual, and lifting them up higher than would be necessary. Of course the ones that don’t seem at all affected with having larger teat sizes were the pegasi, as Anon has noted before they can just fly around without having their back legs clamp down on their mounds, but they do leave their fun bags more exposed. All another pony has to do is just look up, and get a full view of not just marehood and tail hole, but breasts as well. Yet while watching ponies trot, gallop, prance, or fly by, another thought came to Anon’s mind as he finishes his box of donuts.
‘I wonder how a mare’s teats would feel?’ Anon mentally contemplated to himself as he takes a bite of a glazed ring donut. ‘Would they feel like a human woman’s breast, or would they feel different?’
Now Anon has been stranded in Equestria for nearly half a year now, due to a rampant chaos spirit causing mischief, for that amount of time Anon has pretty much accepted his fate of being stranded on this strange planet. As the two most powerful, and oldest, ponies who govern this nation of Equestria can’t find or re-create the anomaly to send him home. So Anon has started to weigh several options in his mind, one of which was connected to his pony watching of mares, could he actually get into a relationship with a pony? The mares are cute and charming in their own mixed way, and of course Anon has amply gotten over the whole weirdness and embarrassment of seeing pony private parts, but could he actually hook up with a mare, and be willing to get down and dirty if his equine partners needs arise? These lines of thought have crossed his mind, and he has admitted to having some mature dreams about him going down on a mare.
“Hey Anon!” a familiar southern twang voice snapped Anon out of his private train of thought, and when he turned to face said pony that called out his name Anon spotted one of his more closer friends among the ponies.
“Hey Applejack.” Anon greeted courteously while absentmindedly waving the hand that still held the half-eaten glaze donut. “What’s up?”
“I need yer help with something, private.” The mare said rather bashfully as Anon noticed a hint of red blemishing her cheeks, and looking a little, nervous.
“So could you come down to the farm with me right now?”
“Sure. If you think I can help.” Anon chipped as he took another bite of his donut.
“Thanks Ah really appreciate it.” the farmer pony said with gracious gratitude. “Come on, follow me.”
While Applejack turned on her hooves and began to trot off, Anon stuffed the rest of his donut into his mouth and grabbed the box of donuts before hopping over the railing of the confectionary’s patio railing, and chased after the fast trotting mare. As Anon chases after Applejack his eyes automatically drifted to the ponies hindquarters, which happens all the time when he falls behind a mare, now normally this would get him a stern look and remark of being a pervert. But ponies values on their nudity and having their, exposed or rear ends ogled, differ from humans. So Anon keeps his eyes flicking between the road he and Applejack are walking on, and looking to the orange mare’s shapely rump, her tail hole and marehood that occasionally get blocked by Applejack’s swaying tail, and the farmers impressive size teats. Which if compared to a human woman’s are close to being a D-cup.
“So AJ, what is it that you need my help with?” Anon asked as he tears his eyes off the farmers hind end, and sped up to be side by side with the pony.
“It’s something that happens every now and then, and when it does come up it’s a real challenge for me to do.” Applejack responded, still displaying the bashful look on her face as she spoke.
“Huh. Must be a real challenge if your asking someone for help, your usually a self-reliant go getter.” Anon praised as he saw that the Sweet Apple Acers was coming into view.
“Well this is one of those things that Ah’m not to proficient in taking care of.” The farm pony admitted a dash of humility in her tone of voice.
“But Anon—” Applejack said before she skid to a stop before the duo even approached the front gate to the farm.
“Ah’m asking you in confidence and understanding that this won’t get weird. Yer the only one Ah could think of to help me because you got them hands of yers.” Anon glanced down at his free hand before looking back to Applejack as she continued.
“So when Ah fully explain what Ah need yer help with you gotta promise that this won’t get weird. Promise?”
“Aye-aye ma’am.” Anon stated with a salute.
“Ah’m serious Anon!”
“Okay, okay! I promise that whatever this is, I won’t make it weird, or get weirded out by this.” Anon said with honesty and seriousness, which brought a small smile to Applejack’s still slightly redden face.
“Thanks.”
The mare then continued to trot to the farm, with Anon following in behind her. Entering the farmers front yard, Applejack guided Anon to the barn in the back of the homestead, but as they made their way to the barn Anon noticed that he hasn’t seen any other members of the Apple Family. Though figuring with it being the afternoon, Big Mac was probably out in the orchard, Apple Bloom was still in school, and as for Granny Smith she was probably fast asleep. reaching the barn Applejack slid the main doors open and ushered Anon inside, and once he entered said building Applejack closed the door and strangely locked the latch on the doors so no one could open them from the outside.
Once the doors were closed, Anon watched as Applejack trotted past him and headed to the back of the barn, where she gestured him to follow as she goes behind a large stack of haybales, so Anon followed the mare to where she wandered off and found her standing amongst a number of buckets, and a few towels on a nearby rack. There was also what looked like an elevated little platform standing off to the side.
“Anon, Ah need your help with milking.” Applejack said with more nervousness in her voice as she looks up to the young man.
“You mean with the cows?” Anon asked as he scratched the back of his head. “Not sure why you needed my help with that when you—”
“No. It ain’t the cows that need a milking.” Applejack quickly said, before she started to trot up onto the elevated platform, before looking back at Anon with a serious look.
“Ah’m the one that needs a milking.” Anon just stood there as what Applejack just said to him start to mingle.
“…you want me to milk you?” Anon eventually repeated after a minute of silence. Applejack just responded with a simple nod. “Okay I might need some context here AJ. Why do you need to be milked?”
“Well it’s a bit a long story. But ever since Ah turned eighteen Ah’ve been producing milk a couple times every year since then, and every time those times comes around Ah have trouble in tapping myself out.” Applejack then looked to her teats as she continues to speak.
“But Ah’m not exactly good at milking myself, as hooves aren’t exactly good at handling such delicate things. And if Ah don’t tap myself out it becomes quite painful.”
“I see.” Anon said as he placed his box of donuts on a nearby haybale. “But can’t you get a milking machine, or something like that?”
“Those things cost a foreleg and hindquarters to purchase, and that’s if they have ones made for pony usage. Not only that, but there a total pain to put together unless you have magic.” Applejack said before looking back at Anon.
“That’s why Ah’m asking you for help Anon. Whenever somepony needs help with something, you’ve volunteered with helping, heck, you’ve become the towns handyman, and repair pony. So Ah figured you’d be able to help me out here.” Anon seemed a bit bewildered as he gave a slightly flustered look.
“Well I suppose I could help you out here, but…” Anon then glanced at Applejack’s teats before looking to the mare herself. “Are sure you want me to basically grope and fondle you, this seems—”
“You promised that you wouldn’t make this weird.”
“And I won’t. But this seems like something you should ask someone your more, closer with.”
“Well Ah can’t really ask any pony in my family to help me with this, and it would be too embarrassing for me to ask any of mah friends.”
“So you feel totally complacent with me basically groping you till you gush milk out.” Anon asked flatly.
“When you put it like that, yeah. But Ah figured that you wouldn’t mind, since you don’t seem interested in ponies in that way.” Applejack admitted as she stood there, fidgeting a little as she looked to be having second thoughts as she and Anon talk on. But her fidgeting stopped as she lurched a little.
“Applejack! Are you alright?” Anon asked worriedly as he took a step closer to the mare.
“Ah’m fine but, Ah’m reaching my limit.” Applejack grunted painfully as she tries to stand back up straight.
“Anon please help me out here, if you don’t then I’d just be laying here in the barn and slowly leak out what I got over the rest of the day.”
“…well I guess I got no choice.” Anon said before looking to a nearby stool and placing it next to the elevated platform, as well as placing a bucket underneath where Applejack’s teats were positioned.
“Alright, let’s get this over with.”
Rubbing his hands together to get them warmed up Anon careful wrapped his hands at the tip of Applejack’s teats, and with a simple tug two streams of milk erupted from the orange ponies nipples, splishing and splashing around in the bucket before settling down. Anon continued to pull and tug on Applejack’s teats, feeling their rather supple yet firm texture along with the very light coating of fuzz, before feeling his pinkie and thumb grace over the erect hard nipple. But as Anon continues to fill the bucket of milk, he was trying to ignore the rather pleasurable moaning and groaning that Applejack was making, especially her little gasps when Anon pinches her nipples by accident.
“Wow Anon, your pretty good at this.” Applejack moaned as another spurt of milk fills the bucket.
“It’s really not that difficult, but this is a little bit strange. Cause I didn’t think that I’d be milking one of my friends.” that’s when a thought came to Anon as he tugged on AJ’s mounds and caused two more streams of milk to shoot out.
“By the way, what do you do with your milk anyway?”
“Well when I first started to produce Ah just poured it down the sink, but over time Ah thought that would be wasteful but Ah didn’t know what to do with it. so Ah actually took it to hospital and see if it was safe to drink.”
“Wait! You drink your own milk?”
“Yeah. Ah also sell it to other ponies.” Applejack said plainly before another moan escaped her. “Doctor said that mah milk is just like the milk we get from the cows, and that it’s safe to use.”
‘And she’s asked me to not make this weird, when she’s admitting to using her own breast—er—teat milk as a food source. As well as selling it to other ponies…’ Anon mentally jargoned before casting a glance at the already full bucket. ‘But…’
“We need a new bucket Anon, this one is already full, and Ah still feel stuffed up.” Anon shifted his attention from the full bucket, to replacing it with one of the other ones, and continued to milk his friend and listening to the mare continue to moan in pleasure as he fondles and gropes her mounds, to free her of her aching burden.
~~~~~
Roughly after a full hour after starting the task asked of him, Anon was able to fully drain Applejack of her fullness. Which the mare was overly grateful for as she laid off to the side, her large mounds nestled between her legs as she rested. While Applejack rested off to the side, chest slightly heaving as she panted with a flushed face, Anon stat up against one of the haybales munching away on another glaze donut while looking at the five filled buckets of milk with curiosity.
“Thanks again for doing this fer me Anon, Ah really do appreciate it.” Applejack said through labored breathes as if she just went through a marathon gallop.
“No problem AJ, but I’m not quite sure if I’ll be up to do this again.” Anon admitted as he looked to the mare.
“It was getting really hard to focus on milking you without remembering that I was groping you up, making you lactate.” Anon stated as his face started to turn a shade of red, while also feeling himself getting a little stiff down below. “Also hearing you moan as I milk you really made it hard to focus, same goes when I started to hear some ‘squelching’ sounds from your back end while clenching and rubbing your hind legs.”
“It wasn’t like Ah was doing it on purpose!” Applejack quickly defended as she sat up, her teats jiggle and wobbling as she did so.
“Ah never felt that way when Ah did it mah self. It just felt really good when you were doing it, and Ah, well…” the mare then started to fidget a little before Anon noticed that her eyes were looking down at his lower region.
“And it looked like you were feeling the same way.” Anon could just feel where Applejack was looking, and moved one of his legs to block the view.
“Doesn’t help when you were letting out rather sexy moans.” The two sat in awkward silence for a bit before Anon heard Applejack scooch her way over to him.
“Well in any case Ah still need to give ya a reward fer helping me out, and since the both of us are a bit randy right now…” Applejack then placed a hoof on Anon’s leg that was blocking his crotch, and gently moved it to the side. “We could have a little romp.”
“Whoa now! You wanna have sex, with me? now?!”
“Why not. Your clearly turned on, and well you already know how Ah am.” Applejack said before placing the hoof on his leg onto his bulge.
‘I keep forgetting these ponies have drastically different views on sex with people.’ Anon mentally bantered as he felt Applejack slowly rotating her hoof around his bulge. But as he continued to let the farmer rub away at him another weird thought came to him, a thought that tied back a thought he had early before this whole milking business. Could Anon get aroused by a mare, and could he get intimate with one?
‘Guess there’s no other way to find out then right now.” Taking a deep breath Anon calmed his nerves before looking down at the eager farm pony.
“If you want to have a romp Applejack, then I’m down for it.”
“Really!” Applejack said with honest shock in her voice, to which Anon just nodded her head. “Wow, Ah rarely get colts, er, males that actually want to have a go around with me.”
“Really?” Anon asked confusedly. “Why?”
“Well most colts and stallions aren’t exactly fans of the more, muscular type of mares like me and Dash, something about how are muscles would be uncomfortable to feel during sex.”
“That’s ridiculous.” Anon stated as he placed the donut he was eating back in the box. “I’ve had sex with a woman who had a lot of muscle, but it never felt like I was having sex with any rough or jagged.”
“So then you really do want to have a go at it with me?” Anon just nodded his head as he started to undo his belt, and unzipped his pants to allow his clothed bulge to bud out from the seam. Applejack laid a bit closer to Anon’s crotch, and immediately started to nuzzle her snout into his bulge, making Anon feel himself getting stiffer.
A few more seconds of feeling the mare shoving and nuzzling his crotch, Anon gently pushed Applejack back before moving to slide his boxers off his member, which sprang up and actually smacked Applejack on her nose. Then without missing a beat Applejack started lick and lap at Anon’s length, causing the young man to shutter as he feels the wet muscle lavish his throbbing erection. But then Anon started to moan as he feels Applejack go from simply licking his length, to swallowing it whole into her warm moist mouth and started to bob her head, sliding his length across her tongue as it wriggles around him. Before Applejack really got into ministrations Anon started to slide his jeans, and boxers off without disrupting Applejack’s flow. Once Anon was freed of his jeans and boxers Applejack really got into giving Anon a blow job, but Anon wasn’t going to just sit there and get sucked off, so he grabbed the sides of the mare’s head and started to thrust in contrast to the farmers bobbing, causing the mare to start moaning and groaning again which actually started to cause Anon’s cock to vibrate in her mouth.
“AJ hold on a second.”
“Wat?” the mare muffled as she looked up to Anon as she stops her head bobbing.
Anon then slide off to the side a bit, and laid down flatly on the floor, which Applejack immediately understood what the young man intended, and while still keeping Anon’s length buried in her mouth moved her body over the young man’s body. Where she positioned her hindquarters over his head, with her teats practically covering his eyes. Now that the mare was in her new position Applejack went back to giving Anon a blow job, while Anon started to fondle Applejack’s teats as he starts sucking on both her nipples, causing the mare to moan even louder, and actually getting some squirts of milk for his efforts.
The milk was like any other milk that he had, sweet, light, and a lit bit on the warm side, but there was something else about it. Strangely enough Applejack’s milk had a slight citrus taste to it, not exactly apple flavored, but something close to it. After gulping away at the farmers leftover load of milk, Anon then brushed the hefty mounds aside before starting to lap at Applejack’s already moisten folds, and feeling her quivering clit brush against his tongue as he laps away at her. As Anon was eating away at Applejack’s folds, his tongue sliding inside her wriggling and clenching inner walls, and messaging her firm yet supple flanks, Anon felt Applejack speed up her head bobbing and really started to lavish his shaft with her tongue, as if she was trying to bring Anon to climax. Yet it was Applejack that climaxed first, spraying her feminine juices all over Anon’s face, while also having feeling some of the farmers excess milk squirt against his arms, while Applejack was forced to remove herself from Anon’s shaft as she let out a guttural moan.
“Quite the hair trigger you got there AJ.” Anon mused as he fiddle around with the mares folds with his fingers, even pinching her clit between his fingers to extend her climax.
“Oh don’t you worry Anon, Ah ain’t done with you yet. Not until I get some of your gooey essence inside me, one way or another.” then in a one quick movement, Applejack re-positioned herself over Anon this time face-to-face, while placing her wet snatch down right top of his lubricated length before gyrating her hips.
“Normally mares don’t let colts or stallions cum inside their marehoods, on account of not wanting to risk pregnancy, but Ah doubt you could get me knocked up.” Applejack then stood up on all fours before using trying to position Anon’s tip at the entrance of her marehood.
“So you’ll get to go into a place most stallion’s will never to go, unless they want to sire a foal or two.”
Then Applejack started to lower herself down, inserting inch after inch of Anon’s cock inside her. As for Anon, the more of his length was being pushed into the mare, the more he could feel her hungry walls clench and grasp at him, before he was completely enveloped in Applejack’s tight yet burning depths. The farmer then started to ride Anon’s length like a cowgirl riding a bull, and to Anon’s surprise yet again Applejack’s marehood felt incredible, and felt like any other woman that he’s had sex with before being spirited away to Equestria. Though feeling the ponies more plump folds was certainly an interesting difference, it was also a nice difference feeling Applejack large teats slap against his stomach with every bounce, and having little spurts of milk squirt out onto his midriff and chest. But Anon wasn’t just going to let this mare ride him for free, and after grasping the side of her waist Anon started to thrust up into Applejack every time she brought her hips down.
“So Anon, how does it feel?” Applejack panted as meet Anon’s thrusts with each of her bounces.
“Feels pretty good. But how does, THIS, feel!”
Anon then pulled his hands off of Applejack’s hips, and started to pinch down on the mare’s nipples, and then tugging at them every time the farmer’s hips came down. This just caused Applejack to moan even louder, and causing what little remnants of her milk storage to finally tap fully out. Soon enough Applejack ceased her bounces, and just sat on Anon’s lap as he tugged at her mounds, but the tugging also stopped before he started to thrust up into Applejack again. And with every thrust he made Anon felt the tip of his member poke and jab at the orange mares cervix, which seemed to really make Applejack cry out in pleasure as she lurched back a bit.
Feeling his inevitable release coming ever closer, Anon surprised Applejack by carefully rotating the both of them to the side, before positioning himself on top of the mare, and went back into thrusting heavily into the mare while she was pinned under. Then in one finally thrust Anon buried as much of himself as he could into Applejack’s depths, pressing the tip of her shaft against the mare’s cervix and fire rope after rope of his load into the mares womb, causing Applejack to actually whinny out in pleasure as she climaxes once again. Several seconds of unloading his backed up cum into Applejack, causing her belly to actually bloat a little, Anon and Applejack collapsed onto their side.
“Dang Anon, you really had a lot stored up, huh big guy?” Applejack panted as looked over her shoulder at Anon.
“Well considering I haven’t had sex ever since I was brought here, and haven’t any alone time to really rub one out, can you really blame me for being so backed up?” Anon jokingly said as he rubs a hand over Applejack’s cutie mare, before sliding said hand down to one of her teats and began messaging it.
“But I take it you liked our little romp around in the literal hay?”
“Yer damn right I did.” Applejack said before scooching out of Anon’s grasp, causing the young man’s shaft to slide out her with a trial white hot sticky cum trailing behind her. the mare then turned around again took Anon’s length inside her mouth, where she sucked and lapped away any lingering cum, which caused Anon to shutter and moan at the feeling as he was really sensitive right now.
“A little salty, yet kind of sweet. Not bad.” Applejack commented. “Speaking of which, how did you like my milk?”
“Creamy and somehow tangy.” Anon remarked as Applejack then laid her head against his stomach.
“Say Anon if your willing, Ah got a proposition fer ya.” Applejack asked with a smile while her tail wagged about.
“Let me guess. Your wondering if I’ll help milk you again whenever you start to feel full again, and maybe have another romp in the hay afterwards?” the mare just chuckled as she scooted closer to Anon.
“So does that mean ya’ll accept?”
“If your willing to spot me a few bottle of your milk?” the mare then leaned in and give Anon a chastised peck on the nose.
“Consider it a deal mister.”
With the milking, and romping, concluded Anon and Applejack decide to rest up a little bit, as they really worked themselves up. and as the duo rested they shared Anon’s remaining box of donuts, while discussing the finer details of their arrangement, with Applejack informing on the typical time laps that she’ll need to be milked. Thirty to forty minutes later the pair have finished off the donuts, and have rested up enough the two friends stood up and started to prepare to store Applejack’s five buckets of milk. After Anon had put his boxers and jeans back on. Once the buckets of milk were carefully poured into a two creates of empty bottles, the duo hauled the crates over to the farm house where they started to store the milk filled bottles into a special storage unit, and once the bottles were put away the two friends then went their separate aways, as Applejack was now free to return to bucking apples. So as Applejack bid Anon farewell, until the next time they meet up, Anon responded in kind, and made his way back to Ponyville.
