A Harsh and Troubled Romance

by Jest

Rating: mature
Tags: My Little Pony: Friendship is Magic, Romance, Sex, Ms. Harshwhinny, Troubleshoes, Slice of Life
Length: 10430

Trouble Shoes is drinking away his trouble when a mare with hunger in her eyes sees her next conquest in the large, lonely stallion.

Trouble Shoes never was good with mares, or stallions for that matter. If it wasnt his luck it was his size that scared him off. Though he may have finally gotten a job in the rodeo his problems are far from over. At least untill a proffessional mare with an eye for males like him comes into his life.

Fetish warning:size difference, tig ol crotch bitties, cervical penetration, impregnation,
cum inflation, stomach bulge and one very shitty set of floor boards

Now edited by the lovely pahnazd

commission for DyoKyo! If you want your own commission lemme know (source will be up in a minute) Watch out there are some very minor errors, if you find any lemme know via PM or comment.

Comic can be found on derpi, 1714914, 1714913, 1714912, and 1714911.

Published 2017-09-15 02:20:06 UTC
Last updated 2017-09-15 02:20:06 UTC

Conquest

The bar was quiet this time of day, nopony really wanted a drink at noon save for the drunks, and those unfortunate few with with sorrows heavy enough to warrant a liquid lunch. One such unfortunate soul sat at the end of the bar, cursing his luck while wallowing in… whatever ponies wallow in, which, in his case, was probably sweat, mud and self pity.

Sure, he had money now, a decent job where he was liked and his unique ‘talent’ was useful, but being a rodeo clown certainly didn't get the mares quite like a rodeo star did. At that rather morose thought he looked down at the bar before him, yearning for a drink. He would have ordered a drink already, but he knew how that was going to turn out after the first time he made the mistake of ordering a drink this early.

Trouble Shoes just sighed and laid his head down on the bar, silently wondering what he had done to deserve such a terrible fate. He must have been terribly unkind to puppies in a former life, or maybe he had unknowingly cursed in Celestia's presence and this was his penance.

His frown deepened when the bartender noticed him and smiled. This wasn't going to end well.

“Hey there big fella, watcha having?” The cheery, yellow bartender with two mugs for a cutie mark asked while walking over with a huge friendly smile plastered on her face.

Trouble Shoes allowed himself to think that maybe this time would be different, this mare was cheerier than the last bartender, and a unicorn to boot! No holding a glass in shaky hooves this time.

“Whiskey, on the rocks.” The stallion replied, hope creeping into his voice.

“One whiskey on the rocks coming right up!” The bartender grinned and pulled a bottle off the shelf while her magic grabbed a glass and added a liberal amount of ice to it. Once the glass was filled with the copper colored alcohol she gently began levitating it over to the stallion on the far side of the bar.

“Wha-!”

Only to hit her hoof on a loose floor board and launch the drink through the air, where the drink came to rest all over Trouble Shoes’ face… ho wasn't the least bit surprised by this particular change of events. At least the glass hadn't hit him this time.

The bartender quickly scrambled to her hooves and ran over to him. “I’m so sorry sir, I don't know how that happened. Please, accept another drink on the house!”

Trouble Shoes merely frowned. “I'd like a cloth first.”

“Oh, ah, absolutely. One moment!” the mare spun around and disappeared into the kitchen.

Meanwhile, the stallion picked the ice cubes out of his hat and did his best to clean his face with his hoof, which was no easy task.

Maybe I should just leave. Knowing my luck, she is gonna end up throwing the cloth in my face as well. He thought glumly, standing up from his stoolquickly making his way to the saloon door.

Halfway to the exit he heard the bathroom door swing open hard enough to slam against the wall. Arching a curious eyebrow, the stallion turned to see what the commotion was, only to see a very happy stallion stumble out into the bar with a blissful expression on his face.

His wide, dopey smile didn't diminish in the slightest when the door slammed shut behind him. He just stumbled his way towards the exit and vanished into the street without a word.

Trouble Shoes chuckled and moved to follow him, only to catch a glimpse of a second pony leaving the stallions’ bathroom, this one a little smaller and a whole lot more feminine.

The second pony stood a little shorter than the stallion from a moment ago and had a finely combed mane that was short, neat, and screamed professional. She wore a pink scarf around her neck and purple suit with a white undershirt. Large gold earrings with some kind of pink gem set in the center hung from her ears. Her coat was a soft brown that complimented her wheat colored mane and tail perfectly.

Trouble Shoes tripped over his own legs, his eyes staying on the mare while his hooves walked on without his guidance, sending him sprawling to the cold floor and landing firmly on his butt.

Meanwhile, the mare was busy running a hoof through her hair, straightening a few errant strands that strayed from her otherwise perfect mane. With that done she belched loudly and straightened her posture, taking the momentary break in her professional demeanor in stride as if nothing had happened. She licked her lips as an afterthought, cleaning off some kind of white liquid that marred her stark red lipstick. With that done she looked around the room.

Her eyes carefully ran over Trouble Shoes’ body and the stallion got the distinct impression he was being carefully scrutinized. When her eyes moved down they grew wide, and oddly predatory.

Trouble shoes followed her gaze and looked down only to instantly blush from embarrassment and move his hooves to cover his shame, which stood tall and proud from his crotch at half mast. Apparently it found the mare as attractive as Trouble Shoes’ rational mind did.

The mare, meanwhile, just licked her lips and did her best sultry walk to the now stammering stallion, who was trying to stand up while simultaneously hiding his frankly monstrous cock.

The few patrons around at such an hour either gawked openly or quietly excused themselves and their partner to relieve a sudden pressure, nopony overly concerned by the display.

The mare quickly closed the distance to the stammering stallion, all the while walking in a way that showed off all her generous curves and naked desire. Her hips swaying and her stance wide, tail swishing back and forth, giving anypony looking an occasional glance at her dripping slit and large breasts that hung beneath her legs.

Trouble Shoes had tried not to look and be gentlemanly, but he happened to glance between the mare's legs as he was struggling to stand, catching a clear look of the powerful assets she had on full display.

The stallion gulped, his cock twitched and the mare smirked.

“Like what you see, big boy?” She asked in a low, sultry tone.

Trouble Shoes merely nodded, the image of those huge breasts seared into his mind. The public nudity wouldn't really be anything to shake a stick at, but it was the sheer fact of her size that had made Trouble stop and stare. She wasn't the biggest he had ever seenm but she was close. Trouble Shoes could only assume she had gone through more than a few exercises to ensure they didn't have the sag a mare of her endowment usually had.

The mare smiled at that and extended her hoof. “My name is Ms. Harshwhinny, but you can call me whatever you want.”

Trouble Shoes extended his hoof without thinking, revealing his now quite hard cock for all to see.

Ms. Harshwhinny’s smile grew and she shook his hoof with a strength he didn't think the earth pony had in her, only realizing half way through that he had revealed himself accidently and broke the shake in order to re-cover himself.

With a blush he responded. “Trouble Shoes, nice to meetcha.”

“Quite. I don't suppose there is a Mrs. Shoes, is there?”

Trouble shoes shook his head. “Nope.”

The mare’s smile grew even larger and she took a small step forward, giving Trouble a whiff of her perfume. It was a subtle smell that reminded him of freshly harvested peaches. Nice, but not aromatic or overpowering; perfectly professional.

The mare gestured to a nearby table. “Can I buy you a drink Mr. Shoes? A whiskey, perhaps?”

Trouble stood quickly, hoping to expose himself for only a moment before he was in a standing position, which didn't help much as he was so large and she so small that she was granted an easy view of everything he had to offer. Realizing his error, Trouble quickly made his way over to the table and away from the stares of curious customers and a bartender that was doing her best to look away while fanning herself.

Ms. Harshwhinny followed him after ordering both of them a drink and knocking the bartender out of her stupor.

“I'll take that as a yes.” the mare giggled, sending a shiver of excitement down Trouble Shoes’ spine.

“Err, yup. Sorry about that, and thank you Ms. Harshwhinny. A mare’s never bought me a drink before. I was a bit embarrassed.” Trouble blushed and looked away, a little self-conscious he had let that slip.

Harshwhinny didn't seem to care though. “That’s a shame, as they are missing out on a huge opportunity.”

Trouble Shoes cocked his head. Was she hitting on him? Normally he would think this was some kind of accident or she wanted to laugh at him, but the way she walked, talked and had bought him a drink spoke that she was genuine.

He couldn't mess this up, this could be his chance! With his jaw firmly set he smiled as kindly as he could and opened his mouth to speak, only to be interrupted by the bartender. “One Whiskey on the rocks, and a paralyzer for the ladyyyyyyyy-”

The bartender’s hoof slipped on something and though she held tightly onto the whiskey, trying not to get a repeat of last time, she didn't have the skill to hold on to both drinks and sent the other one flying at Harshwhinny, covering her very proffessional jacket in booze.

Trouble Shoes groaned at the sight; another possibility ruined because his bad luck. He sighed and started to get up, only to be surprised when he looked into her eyes only to see an intense lust burn within instead of the annoyance he assumed would be there.

“I'm so sorry, ma'am. I can't believe that happened again! Please give me a moment and I will make you another on the house.”

“That won't be necessary, miss.”

“But-”

“Right now, I must get out of this shirt. Save that drink for later.” All of a sudden the lust that burned in her eyes disappeared and she stood up from her chair. “Mr. Trouble Shoes, would you mind accompanying me back to my room? I need to change, and maybe we can have a drink there.”

“I'm really sorry miss. I don't know what's wrong with me today.” The bartender’s face drooped and Trouble felt guilt rise in his stomach; It wasn't her fault his luck had made this happen.

Ms. Harshwhinny quickly assuaged the bartender’s fears and picked up her chin with a gentle hoof. “Don't worry about it, dear. A little bad luck is nothing to cry over.”

Then she turned and walked towards the stairs, casting a glance over her shoulder at the stunned stallion. “Coming, Mr, Shoes?”

The stallion quickly got up to his hooves and moved to follow, quickly catching up to the smaller pony just as she reached the top of the first flight of stairs, granting the stallion an unfettered view of the mare’s now dripping, gaping slit and huge breasts. He nearly tripped up the stairs, too busy thinking about what he just saw, which made the mare stop and turn to him and giggle.

Trouble Shoes gulped and quickly followed after the mare. I think i'm in love.

Walking to Ms. Harshwhinny’s room didn't take long, but to Trouble Shoes it felt like an instant. The mare walking before him knew where his gaze lay and used that information to her advantage, swaying her hips just enough to send her generous flanks swaying along with her breasts. When they reached the door, Trouble nearly ran fast first into the mare’s exposed cunt but stopped at the last second.

Harshwhinny looked back and smiled, dropping her keys. “Oops, one second, cutie.”

Before Trouble could look away, the mare bent right over and moved her tail aside to give him a perfect, unfettered view of her wet, gaping cunt.

The stallion’s mouth opened and closed as if to speak but nothing came out. He almost felt like a compliment would be appropriate, or an apology for being so close, but he was transfixed.

Then, like that, she stood back up and his perfect view was gone, replaced by one of a neatly combed tail. Within seconds the door was open and Trouble followed Harshwhinny inside without thinking.

Once inside, the gravity of the situation hit him and he sighed. She would regret this night and possibly hurt herself if he didn't put a stop to it.

The mare in question was not privy to his inner turmoil and flicked her tail as she walked from the small bedroom to the equally small bathroom. “One second, cutie. I gotta freshen up.”

“Hold on a second, miss Harshwhinny. I have something I have to tell you.” Trouble said glumly, knowing what was going to happen next.

The mare stopped and turned, lifting an inquisitive eyebrow. “What is it?”

The stallion gulped. “We can't do... you know… it. I’m too big, I’ve hurt every mare and a stallion or two that's tried. I don't want to see nice gal like you hurt like that.”

The stallion sighed and turned towards the door, only to be stopped when he heard the mare laugh. Turning quickly, he looked back at her a little confused. She stood there with a smirk on her face and fire in her eyes. “Honey, you’re big, but you aren't much bigger than my last colt friend... err, dragonfriend.” She shook her head dismissively, walked up to Trouble and planted a light kiss on his lips. “Trust me when I can say I can handle you. Now sit down and get comfortable, I will take just a second.”

Without waiting to see if Trouble sat down, the mare turned to the bathroom and sauntered towards the door, Stopping for a second and throwing a look over her shoulder, their eyes met and, for a second, the mare understood the depth of his indecision. She threw him a smirk and spread her legs wide, tossing aside her tail and letting Trouble get a clear view of everything she had to offer. Trouble’s mouth flopped open, for a second he could have sworn he saw all the way to the mare’s cervix. Sure, he had gotten a few glimpses, but never a perfect angle like this. She was positively gaping and they hadn't even done anything yet. The stallion’s erection shot up and nearly slapped him in the chin. Seeing that her stallion was now ready to go and had no lingering doubt, Harshwhinny turned and entered the bathroom, closing the door behind her, leaving Trouble to his thoughts. A mare that had dated a dragon... wow. And she sure looked…. accommodating enough for him to finally enjoy himself.

The large, stallion flopped down onto the bed, the rusted springs creaking as his weight settled fully. “I wonder how big that dragon was… I can't believe I am bigger.” His cheeks lit up at the thought and a strange sense of pride welled within him.

After a minute his excitement had gotten the better of him and he sat at the edge of the bed, positively bouncing with anticipation. This was it, the first time he could really have sex like a normal stallion! And she was incredibly attractive to boot.

Just as the stallion’s excitement was about to turn into impatience, the door opened and revealed a now nude Harshwhinny. Trouble Shoes gawked; he wasn't sure how but she was even more attractive without clothes or jewelry.

The mare noticed his stare. “Like what you see, stud?” Trouble merely nodded, not trusting his ability to say anything that didn't sound incredibly stupid. The mare shivered, revelling in Trouble Shoes’ unabashed lust. “I love the way you look at me. I bet you are thinking of fucking me right now, aren't you?”

Trouble Shoes nodded dumbly, holding his mouth shut. “Why don't you come over here and fulfill your fantasy? I’m wet...” The mare turned slowly, raising her rump and dropping the front half of her body to the dirty wooden floor. “... and so very ready for you.”

Trouble shoes shook his head. This was real, this was happening! He couldn't screw it up! With a start he got to his hooves and scrambled off the bed, all the while staring in slack jawed awe at the mare who moved her hips in long slow circles, her tail swishing back and forth, teasing the stallion with a brief view of what he longed for.

Trouble stopped, gathered his wits and walked over with a determined gait, all the while flexing and showing off his considerable muscle structure.

“Oh wow, you are quite the stud. I can't wait to feel you inside me.” The mare winked and licked her lips.

Trouble grinned and walked over her, his huge body easily covering the smaller mare completely. He contemplated stopping and maybe taking a taste, but they both wanted this. There was no point in foreplay when they were both this hot and bothered. He lowered his back half and tried to angle his cock properly, but found he was a little too far back. With a growl of annoyance he took a step forward, only to trip at the last second, sending himself sprawling on the ground.

His cock slipped inside something warm, soft, and oh so very tight. In Trouble’s frantic attempts to stand back up he managed to wedge himself in the last few inches, his heavy balls resting against something warm and soft. A low, throaty moan from below him eased Trouble’s panic and he looked down at Harshwhinny. What he saw made him excited and confused in equal measure. The mare’s tongue had lolled out of her mouth and onto the cold wooden floor, her eyes were rolled back in her head and a moan slithered out of her mouth.

This was it, the feeling he craved, the ecstasy that was foreign until this very moment. He was bottomed out, and she was unharmed and loving it. If every facet of his very being wasn't entirely focused on her he would have pinched himself to see if he was dreaming.

He dared not tempt fate however and instead opened his lips and asked a question he desperately hoped she said no to. “Should I stop?”

The mare shook her head a little and came out of her cock filled coma just long enough to fix him with a hard stare. “No. It hurts so fucking good. I want to feel you fuck me within an inch of my limit and then throw me screaming over the other side.”

The stallion found the statement strange but could not deny that it was the single hottest thing anypony had ever said to him, and he could do nothing but oblige the mare’s desires.

With an eagerness that surprised even himself, he picked himself up off the ground just enough for a better angle, dragging the helpless mare which had seduced him. Using his massive cock, he lifted her up and to her knees where she could prostrate herself properly in front of the new object of her devotion.

With a grunt, the stallion threw his hips forward, putting every last throbbing inch he had back inside the mare he had claimed. Another moan slipped forth from her lips and traveled across the unwashed floors.

Feeling slowly returned to her nethers with it a stab of pain. She had always dated the biggest, most virile individuals she could and when she couldn't date them, a fling usually sufficed. She held a certain sense of pride at the fact that most stallions could slide into her without trouble and still love every second of the ride she put them through.

Now… Now she knew that time had come and gome. This stud, this beast had ruined her utterly for anything not the same or bigger than him. There was no way around it, her muscles felt loose, her cervix hanging open, admitting the massive intruder without a hint of resistance.

His hips pulled back, dragging the mare backwards across the ground as her body clung to his cock like it was a life line. Her hooves scraped across the ground and she tried to resist getting dragged around like an oversized cocksock, But by the time her hooves found purchase, her stud had thrown his hips forward once more, slamming back inside her with such force that his balls slapped into her tits with enough force that her moan rose a few octaves, quickly devolving into a heated, throaty growl.

Trouble Shoes was in heaven. He'd never had anyone able to take him so completely, and the fact that she loved every single second of the brutal stretching made this easily the best lay of not only his entire life, but even his dreams. Why, if he wasn't so busy fucking the everloving shit out of this slut, he would have pinched himself to see if he was dreaming.

That brief moment he spent not paying complete attention to the mare impaled on his cock was unfortunately all his bad luck needed to act up. His hoof slipped just as he was pushing forward, sending his entire body moving forward too quickly. His back hooves tried to find purchase but the weight on his cock carried him forward over his stumbling hooves and sending him sprawling to the ground.

The frantic clatter of hooves was stopped short as the pile of ponies hit the ground, the large stallion not able to help as he plowed the mare into the floorboards loud enough to sound like somepony had tipped over a dresser.

“Wow, what’s...” Harshwhinny tried to ask but suddenly found her face meeting the floor far more intimately than she had initially desired.

“I am so sorry! I didn't mean to do that, are you alright?” Trouble Shoes stopped moving, not wanting to add to the problem.

A low throaty moan that carried more ecstasy than Trouble Shoes thought possible to convey put his fear to rest as the mare beneath him writhed in the midst of a sudden orgasm. At first, Trouble wasn't even sure that was what was happening, but when he felt the already well lubricated hole wrapped around his cock suddenly tighten even more than it already was, he knew she was enjoying every second of it.

Not needing further prompting, Trouble got to his knees, allowing himself enough room to thrust but not enough to let the tiny mare any room to move, which suited her just fine as she made no attempt, merely lying there limp with all four limbs splayed out in every direction. She didn't even bother to lift her head from the floor, merely resting her chin on the ground as her stud continued to use her limp body as they both wanted.

The room quickly filled up with the sounds of their passion and the heat of their bodies again, turning the cold quiet room to one filled with the smell and sound of debauchery. For minutes they lay there, the huge stallion plowing the smaller mare impaled on his cock across the ground, each powerful thrust smacking his balls against her tits and squishing her between him and the ground.

A sort of understanding was reached within those few minutes; the mare would squirm a little if it was a little too rough and Trouble Shoes would slow when he wasn't sure, waiting for the mare to push back against him and assure him that she was still alright. Within those few minutes they were fucking like they had been for years, which sent both ponies’ hearts a flutter.

Until a sudden harsh knock on the door drew them out of their lust. The stallion reacted first, stopping his thrusts and turning his attention to the door, much to the now annoyed Harshwhinny’s dismay.

“Ignore them and they will go away. Now, hurry up and fuck -” Three more hard knocks on the door made Harshwhinny stop and groan in annoyance. “Fine. Be there in a second!”

As the mare moved to stand, the stallion got up and gently began pulling his cock from the mare’s destroyed hole. After a tense second where it didn't quite seem as though the medial ring wouldn't come out, the mare stumbled forward, Trouble’s thick cock slipping out of her with an audible slurp and a small river of pre.

Ms. Harshwhinny stopped and took a breath, recovering from the sudden feeling of emptiness that filled her. Three more hard knocks on the door made her attention shift and her annoyance build.

“I'll be right there!” Grumbling curses under her breath, the mare stumbled over to the door, her legs giving off tiny jabs of what felt like electricity as they woke back up.

Throwing open the door in a huff, Harshwhinny wasn't exactly overly concerned with her appearance, her annoyance overcoming that. Trouble at least had enough forethought to duck away from the door and hide behind the bed so nopony saw him or his unmentionables.

The mare probably should have given her appearance a little more thought as the guard stallion standing at the door nearly fainted at the sight. The usually reserved and professional mare he had seen a few times was replaced by one covered in bruises and scrapes, smelling of sweat, blood and something else the stallion decided not to dwell on.

“Are you alright, Ms. Harshwhinny? We received a noise complaint a few minutes ago and…” The stallion stopped, watching the mare as she licked a small spot of blood from her lip.

“Is that all?” She asked curtly, wiping a stray strand of wet hair from her view. “I was right in the middle of someone.”

“I, er, are you sure nothing is wrong?” The stallion asked, trying to lean into the room to see if she was perhaps being held against her will.

The mare just grunted in annoyance. “That depends, how big is your dick?”

“I, uh, beg your pardon?” The stallion asked, taking a step back without thinking, the hungry look in the mare’s eyes unnerving him more than he cared to admit.

“Your dick, how big is it?” The mare rolled her eyes and stood up on her hind legs, using her forehooves eighteen inches apart. “This big?”

The stallion’s eyes shrunk and he began backpedaling. “Well... I... you see, it's not the size that-” And just like that the door was kicked closed by an annoyed mare, right in his face no less. Sending the confused and emasculated guard falling to his butt. “What the hell just happened?” The guard looked back and forth down the hall before just shrugging to himself. “Fuck this, I need a drink.”

Back in the room, Harshwhinny blew hard through her right nostril, dislodging a build up of blood. “Now, where were we?”

Trouble peeked out from the other side of the bed, not sure if he should leave his hiding place despite the fact that it hardly hid his enormous frame anyway. “Were you really going to invite him in if he was big?”

Harshwhinny just snorted in amusement and flopped onto the bed. “Pfft, that shrimp dick could never compete with you. I was just making sure he wouldn't bother us again. Now, get up here and fuck me already.”

Trouble stopped for a moment, slightly unsure. His still raging erection however decided to throb, giving him all the prompting he needed to climb back on the bed. His weight made the bed creak and the old springs shriek, making both ponies cover their ears in annoyance.

“Eesh, lay down stud, it's my turn on top.”

The stallion didn't even hesitate to flop down on his back, the bed groaning in protest at the sudden shift in weight. Now that he was right where she wanted him, the mare slipped in between the stallion’s legs, relishing the strange feeling of smallness that came with being dwarfed by the large stallion’s bulk.

She stopped and moved back down, almost forgetting something she had wanted to do since the very moment she had first met the stallion. She clambered back down the stallion and took his massive set of balls in both hooves, salivating at the sheer heft of them. They were huge, incredibly heavy and for tonight they were all hers. She couldn't resist the siren song any longer, buried her face into the huge orbs and inhaled deeply, letting the smell of his musk wash over her and make a surge of heat radiate from her loins.

Her tongue slipped out of her mouth and she absentmindedly ran it across the huge orbs. Her lips were barely able to slip around the massive organs, she had to give up and continue to worship the massive pair of pure masculinity in whatever way she could, until finally the heat burning within her rose to a fever pitch and she couldn't resist the call any longer. Quickly getting up, she clambered up the stallion and began moving his massive endowment to its target.

The mare stopped to enjoy the feeling the large cock of her mate resting between her thighs, held tight and already aligned for when the mare wanted it. Trouble hadn't given much thought to the situation he had found himself in once things had begun to get heated, but now that he had a moment to himself he couldn't help but feel as though he was being used… which was just fine by him now that he thought about it. The feeling of not being in control was an utterly alien one for the large stallion, never having a mate that was adventurous or brave enough to mount him, and the new territory was exhilarating for him.

The territory would only get newer when the mare used her thighs to line up his cock, only to shift a little too far forward and push the bed over a small lip in the uneven floorboards. That sent the mare sprawling backward off the ledge no one knew it was on. messing up her perfect alignment and sending the cock into somewhere much, much tighter.
“Wha-eeeee!” After the incident one nearby resident will comment saying she heard a mare screaming from within the room, however the truth was a little different... and a lot funnier.

“Ow, holy shit that hurts almost as much as your cock up my ass. How in Equestria did you hit that high note? I think only dogs could hear the end of that one.” Harshwhinny merely grunted and rolled her hips, pulling herself up slightly only to fail in removing the cock from her ass, her hole clenching down on it like a vise.

Meanwhile, the stallion now felt like a rat in a trap wasn't even listening, too busy silently screaming as it felt like his stallionhood was in a less than metaphorical vise. After several agonizing seconds the pain slowly lessened until it became a dull throb, his silently screaming mouth slowly closing as he regained feeling in his nethers surprisingly quickly.

The mare raised an eyebrow and looked down at him quizzically. “Alright, stud?” The stallion merely eeped and nodded his head, drawing a smirk from the mare. “Well, if you’re done screaming, I am gonna move. That sudden penetration was… hot.” The last word came out as a breathy half moan of ecstasy.

This mare is nuts. Trouble thought to himself, then quickly added an addendum. I love her.

Her movements at first were slow and methodical, the sudden penetration had almost been complete, but in truth there were a few inches outside, meaning it was slow going as she relaxed her muscles with practiced ease. Within a minute of slow, gentle rocking, pleasure slowly began to seep back into Trouble’s mind and the aching his cock was replaced with a more needful, less painful kind.

Now relaxed and ready, the mare leaned her weight back on her hooves and bit her lip, easing the massive cock inside her into unfamiliar and unpenetrated area. Both ponies moaned as the pleasurable feeling of stretching assaulted them both. The mare’s hole stretching to accommodate the massive invader that had speared itself inside and so beautifully ruined an otherwise perfect hole, ensuring only it and one similar would only ever be able to receive pleasure from it.

The mare rocked her hips back and forth, shifting her weight from her front to her back hooves, easing more and more cock inside her and savoring the feeling of her body being stretched to suit the demands of her massive mate.

Her teeth bit into her lips, drawing a thin line of blood which she ignored. She was almost there and the suspense was killing her. One last backwards thrust was all it took, and when her flanks met his crotch, both ponies gasped suddenly.

“You are one amazing mare, you know?” Trouble blurted.

“You aren't so shabby yourself, stud. Can't say I’ve had a bigger cock before in my entire life, and that's quite the accomplishment.”

“R-really?” Trouble asked, a sense of pride welling up inside himself.

“Of course. You damn near punched my stomach with your cock on that last one.”

“Oh, um, sorry about that.” Trouble responded sheepishly, rubbing the back of his neck awkwardly.

“It was really hot.”

Trouble Shoes just shook his head; this mare was something else, that was for sure. Then, as if reading his mind, the mare wiggled her hips and let out a long sigh, enjoying the tantalizing feeling of her body being stretched to its limits by Trouble Shoes’ enormous cock.

The stallion got the unspoken message and moved his hooves up to grip the mare’s sides as she shifted her weight around in order to get into the perfect position. The mare’s hips surged forwards suddenly, making the stallion grip his partner tighter. The empty feeling left behind by the huge intruder was annoying but the promise of what came next made it all worth it.

Just as Trouble Shoes feared she was going to pull all the way off she smirked and suddenly threw her weight backwards. Her weight and surprising amount of muscle sending her all the way back until their flanks met with a hard smack. Both ponies moaned as the feeling of penetration/fullness came thundering back.

With her partner now onboard to her little strategy, things went even smoother next thrust, her body flying forwards until he almost slid out of her gaping hole only to pound back again and again. Both parties slowly worked into a rhythm, going faster and faster as they seemed to synchronize.

Within minutes they had reached nearly a manic pace, their moans the only sound other than their bodies crashing together in a cacophony of lust and debauchery; their pace slowing and speeding up as they learned the subtle signals that only lovers knew.

Trouble mainly took a backseat to his partner’s overwhelming desire, her unbridled lust taking the reins and refusing to let go, which he didn't mind in the slightest. There was something incredibly arousing about the fact that she wanted him so desperately that it bordered on need.

And need him she did. Harshwhinny had always been a size queen, never settling down for a real relationship and instead enjoying ‘friends’ all over Equestria that would help satiate her desires and, as time passed, her appetite grew until she met him. Now? Well, now she wasn't sure if she could go back to a smaller cock; he was simply the best.

Her own inner musings were interrupted when he grunted quite peculiarly; it was a deep, satisfied grunt that she knew was about to signal the end of their little fun. She moved fast, picking her hips up quickly and walking forwards until his cock slipped out of her gaping, ruined asshole with an audible pop followed by a small trickle of pre that fell out of her hole.

“What? Why did you stop?”

“You were about to cum, weren’t you?” Harshwhinny said in a harsh and disapproving tone.

“Err, yeah, I thought that's what y’all wanted.”

The mare leaned down and booped the stallion on the nose, dispelling some of the tension. “You have to tell your partner when you’re going to cum. Besides, I want to feel you drop your huge steaming load in my pussy.”

The stallion gulped. “Wouldn't that get you pregnant? I don't know if i'm ready to be a dad…”

The mare merely snorted dismissively. “Oh, I wouldn't worry about that; this old field is as barren as the desert. Now then, let's quit stalling so you can fill me up.” As the mare moved back into position she looked down into her stallion’s eyes. “I can't wait to feel your hot load inside me, stud. I am going to walk around for the rest of the day with a saunter in my hips, feeling your cum swirl around inside me and slowly leak out of the hole you ruined.”

“You are one kinky mare.”

That brought a smile to Harshwhinny face. “You know it, stud.”

Without waiting further, the mare lined up the stallion’s cock and gently slipped inside her now stretched and welcoming hole. Both ponies let out a slow moan as the stallion slipped back inside her, the feeling of fullness and utter completeness that came with the act robbing them of the ability to think or do anything other than revel in the pleasure of it.

It took only a few seconds for his fat cock to slip back inside, the earlier brutal pounding her pussy received being more than enough to keep it stretched until now. Though to Harshwhinny it was slightly bittersweet, as the brutal ass fucking she had received only moments ago had left one of her holes so terribly empty. She made a note to make sure her stud fucked her ass as hard as he had her pussy before she sent him on his way.

His medial ring, though still as large as it was the first time, slipped in easily, though Harshwhinny still had to give a slight thrust to ensure it slipped inside without a fuss. His flared head slipped inside her cervix without so much as slowing down, the barrier already distended and open after the brutal fucking she had received earlier. Though Trouble Shoes hardly noticed when his head slipped inside the deepest recesses of her body, she sure did, letting out a low moan of pleasure as she felt her very womb be filled by her monstrous partner. With a wet thump their hips met once more, prompting Trouble Shoes to stop and look down.

His mare was absentmindedly stroking a bulge in her stomach with her hoof, tracing its outline and moaning quietly to herself. Just as Trouble Shoes was about to ask what was going on, he felt it. The distant sensation of something small running across his flared head, just as Harshwhinny ran a gentle hoof over the tip of the bulge.

“Is that me?” The stallion asked in disbelief. Sure, he knew he was big, but the bulge was almost up to the mare’s ribcage!

She merely nodded. “It is.” the mare shuddered suddenly, mashing their hips together in a desperate act to feel him even deeper inside herself. But she could go no further, the cock rubbing against the deepest reaches and satisfying an itch Harshwhinny had been trying to scratch for years.

She let out a deep moan as she felt a now familiar sensation of utter contentment wash over her. It didn't last long though and her lust quickly bubbled back to the surface, throwing her back into the tempest-tossed waves of pleasure and desire.

Trouble Shoes didn't have to wait long for his partner to begin to move and within seconds the near frantic pace they had only a minute ago was reached once more. Their bodies coming together almost instinctively at this point as they reacted to the other’s feelings of intense need.

Though there was a small part of the stallion’s mind that hesitated at the idea of cumming inside her, he was forced to admit that the idea was hot as hell and there was no way he could pull out anyway. Even then there was a small part of him that worried; he had always had large ejaculations, to the point that even his stallion friend of many years had dumped him over fears that his stomach would explode. What had Flash Sentry said? Something about guard insurance not covering a burst stomach?

Oh well, it didn't matter anymore, if she was confident that would be good enough for him. Besides, she was a mare that could handle this type of stuff… right?

Due in part to his own inner turmoil, it took a little longer for him to reach orgasm, which was completely fine by her as she never wanted to get off this perfectly shaped cock for the rest of her life.

All good things must come to an end, and this, sadly, was no exception. Though her thrusts slowed and their bodies touched less and less, his orgasm was still slowly bubbling to the surface.

“I gotta warn ya, I cum alot. You sure you can take it all? I can finish outside if you want.”

The mare merely snorted in amusement. “Stud, I’ve taken more loads in one night than you've probably squeezed out in a month. I think I can handle this.”

Her confidence, though infectious, didn't quite persuade Trouble Shoes from worrying, though it did clear him of some of his guilt. With a shrug, the stallion pulled his mare closer, not wanting to spend the last few precious seconds before he came in a slow and distant pace.

He wanted her close, he needed to be rough and she was more than willing to oblige him. Her body was pulled close, fitting into the space between his legs like a puzzle piece, her muzzle just barely able to reach up to his in order to place a kiss on her stallion’s lips.

With her interlocked just as he wanted, the stallion gripped the mare with both hooves and really fucked her, regretfully having to break the kiss in order to truly plow her as he desired. The mare cried out and let her limbs fall slack, her legs barely able to touch the bed from her perch atop his barrel.

The stallion’s grip coupled with the complete loss of control was ecstasy to Harshwhinny who came and came for what felt like forever. Each wave of pleasure crashing against her mind until her mouth hung open and her tongue lolled out, too far gone to bother about what unprofessional and frankly embarrassing expression she was no doubt making. It didn't matter, nothing mattered but him. Or at least that's what she thought until she felt him stop moving.

Then a new sensation assaulted and captivated her; the huge cock head suddenly pounded into her womb with one final resounding thump, before growing larger and larger until she thought she might split in two. Before it stopped she heard something as terrifying as it was arousing.

A sloshing gurgle met her ears and confusion ran through her mind. Was that his balls? She had no time to think as the first surge of cum was already exploding through the cock inside her and into her womb with an intensity that made her cry out in a mixture of shock and joy.

When he had entered her she had loved it, when he had taken the reins and fucked her she had grown addicted, but the second she felt his cum slam into her womb and her body almost instantly begin to bloat as it was forced to deal with wave after wave of cum, she knew there was no going back.

The stallion grunted and gripped his mare tighter, one hoof guiding her muzzle to his and forcing the goofy expression from her face and their lips together. Their kiss was rough, the two ponies coming together with an intensity that frightened them both. They longed for each other and it showed. The mare wasn't quite as enthusiastic to start, but after the first few waves of cum slammed into her body she seemed to overcome the assault of pleasure and returned with the vigour of a mare half her age.

On and on they kissed, until they had both long since come down from their respective orgasms and been left a breathless mess of pleasure. Eventually they parted, neither wanting to but both having to admit that they needed a moment to catch their breath. The moment they parted they were allowed a view that startled them both.

“Sweet Celestia.” The stallion muttered.

“I think this might be the fullest I've been in a long time.” The mare muttered, patting her cum filled womb that had grown until it stretched against her skin and made her look about ready to pop with twins.

“Does it hurt?” The stallion added, a worry in his eye.

The mare merely laughed. “Quite the contrary, this is the most satisfied I've ever been in my entire life.” The mare looked away suddenly, a quiver coming to her lips. “Do you mind if I get down for a second? I really want to taste you.”

The stallion’s limbs remained rigid for a second before loosening up enough to allow the mare to squeeze out of his grasp. The awkward climb off his thick shaft was made somewhat difficult as she had to walk forwards, over the stallion's head and off the side of the bed due to its sheer size. Slowing when his medial ring popped out of her abused cunt and finally one last time when his still semi hard head slipped out of her hole with an audible slurp, followed by a short gush of cum that spilled out of her and onto Trouble Shoes’ stomach.

“Sorry about that, stud.” The mare stuffed a hoof into her cunt while she leaned over and extracted a rather impressively sized plug that she swiftly stuffed into her overfull cunt.

She hardly even seemed to notice as the huge piece of enchanted plastic slipped inside her and filled her hole perfectly, merely grunting at the sensation. She brought her hoof to her lips after that, never taking her eyes off Trouble’s as she thoroughly cleaned her hoof and swallowed the copious amounts of cum that had covered it so completely.

With that done she moved to the stallion’s stomach, where he lay unmoving since she dismounted, his quickly softening cock laying half limp on his belly. “Here, let mommy clean that up for you.”

Before the stallion could say anything, she had leaned down and began licking up any stray cum that marred his coat. Quickly swallowing every last drop she could get in her mouth, only tasting it for a moment before her desire to have his cum inside her overrode her curiosity.

With his stomach clean, she picked up his still impressive cock with in a hoof, eyeing up the titanic appendage. It was mottled with a tone that was several shades lighter than his coat, making the word cute spring to Harshwhinny’s mind even though that hardly fit with such a massive hole-destroying cock like his.

Wiping the silly thought from her head she dove down and wrapped her lips around the cum coated head, her mouth barely able to even reach around the huge organ despite the fact it had shrunk significantly from the time it was lodged inside her womb, pumping her full of spunk.

The mare moaned around the cock inside her mouth and she quickly worked her tongue across every surface, slurping up every last drop until she could find no more of his delicious cum. Keeping the ball of cum she had saved so far, she pulled her lips from the cock and worked her way down the side, cleaning every inch of the penis she could, saving every last drop until her cheeks bulged and her stomach yearned to be filled. After a few more passes and another quick stop to suckle Trouble’s head once more she moved back a few inches, eying her work.

His cock was completely clean and clear of any trace of cum. “Err, thanks. You gonna swallow all that or what?” The stallion asked, cocking his head and looking at her bulging cheeks with amusement.

The mare merely rolled her eyes while she rolled his cum around in her mouth, savoring the flavor. As predicted, he had a distinct earthy tone to his cum that she liked. It wasn't overpowering, nor was it the only distinct flavor for it meshed well with a soft sweet undertone that Ms. Harshwhinny had to admit suited him perfectly.

With her curiosity satisfied, she looked the stallion in the eye and swallowed audibly, gulping down every last drop of cum in her mouth in one swift movement. Trouble Shoes’ mouth hung open as he watched his load travel down her throat and disappear into her belly.

“That was hot.” he remarked.

Harshwhinny smacked her lips and ran her tongue across her teeth, tasting the last vestiges of his seed. “Thanks, stud. Don't suppose you’re up for round two yet, huh?”

The stallion shrugged and eyed his now flaccid cock. “In a minute, probably.”

“Alright, stud, I am gonna grab some water in the meantime. You want any?” The stallion shook his head.

Turning towards the bathroom, the stallion was afforded a generous view of the mare’s backside, which he took full advantage of. Her holes had been utterly ruined, and though there was a hint of guilt in the stallion’s mind, the majority of his thoughts were ones of pride. He had done that, he had ruined her for any other stallion and made both her ass and pussy hang open, dripping a thin line of cum from both holes that was only mostly stopped by the plug stuffed in her pussy.

His cock twitched and started to grow as he stared at the slowly retreating mare, growing by the second until, by the time she had turned around with glass of water in hoof, he was completely erect. Downing her drink quickly, the mare trotted back over to the bed, swaying her hips all the while.

“Thanks for waiting, stud. It seems like you’re ready for round two now. So, tell me...” She leans in, whispering seductively in Trouble’s ear. “... how do you want me?”

The stallion pondered it and came up with too many ideas. In the end he knew that his night was just beginning, and he merely shrugged and chose the first one to come to mind. Many hours and many, many orgasms later, the pair lay on the now wet bed, ignoring the disgusting state of their sleeping arrangements they drew close.

Together they wrapped their legs around the other, the mare’s head falling beside the stallion’s, nuzzling him softly while she relished the feeling of fullness. The feelings of smallness and security bringing a joy she hadn't felt in a long time, all the while Trouble Shoes thanked his lucky stars and for the first time in his life, thanked his rotten luck.

Trouble Shoes sighed and leaned on the post next to where the other rodeo clowns gathered around and waited for the show to end. The day hadn't been especially, hard but with its completion came the realization that he hadn't seen Ms. Harshwhinny among the crowd. The thought alone was enough to bring a pang of heartache to the lonely stallion who sighed, ignoring the other clowns as they talked idly about what they were going to do with their weekend.

Thoughts of the day after that perfect night came unbidden to his mind, remembering the hours spent in a tangle of limbs with the pony he had hoped would stay long enough for him to tell her how he felt. But it wasn't meant to be, and in the morning she was gone, leaving behind only the scent of their love from the night before and a note. It was short, sweet and to the point, simply saying “I am sorry but I can't settle down, there is too much out there left to experience and so much left to do. But one day I promise to come back and take care of my sexy stud, even if only for a day.”

The memory was bittersweet, and at times he cursed the strand of hope she had dangled before him, but even when he was at his loneliest he couldn't give up on her, not yet.

The stallion shook his head and looked out at the last bit of the show, hoping to distract himself from his melancholy. In the distance, a pig wrangling competition was about to be won by a scrappy young colt from Canterlot. But that's not what interested him, he only had eyes for one mare. With grim reluctance he began scanning the audience for the mare that had stolen his heart and vanished into the night. He knew the act was futile but, he had spent a few minutes at the end of every show over the last few months looking for her, and he wasn't about to stop now.

He noticed the usual groups of people; a small collection of fillies and colts spread out close to the action with a teacher watching over them like a hawk, few drunks a little higher up on the stand were stumbling around the beer vendor. After that the ponies in the stand seemed to blend together into one great pastel coloured mush.

The stallion sighed once more, vaguely aware of the fact that the action on the field was dying down, meaning the competition had come to a close and a winner had been found. Which didn't matter to him one single iota.

With his eyes coming close to the end of the row of stands to his right a lump slowly grew in his throat. She ain't here, figures. He sighed and scanned the last few faces in the stands only to stop and slip from his post.

Quickly he surged back to his hooves and looked back over at the last row of seats where a very familiar pony sat, smiling gently down on the stallion. Trouble shoes blinked twice and looked back, vaguely aware he should at least wave or something, but a loud voice suddenly grabbed his attention.

“-AND THAT'S IT FOR THE OAK BLUFF RODEO! DON'T WORRY NOW, WE’LL BE BACK NEXT YEAR! YEEHAW!”

The crowd began to move and Trouble realized that his attention had wavered, temporarily losing sight of the mare. He swung back to where she was sitting only to see the hustle and bustle of ponies disembarking from their seats and making their way away from the show and back to their homes.

He hopped up from his post and desperately searched the crowd of ponies to no avail. Cursing silently, he continued to watch the crowd for any sign of her, ignoring the looks of confusion from his fellow clowns.

After a few minutes the seats emptied and any chance he had of finding her vanished with them. He sighed and hung his head in defeat, trudging down towards his dressing room next to the bathrooms.

So despondent was the stallion that he hardly even noticed the presence of another individual next to his dressing room.

“Hey there, stud.”

Trouble’s eyes shot open and in an instant his foul mood was washed away, replaced with confusion and hope. Nopony had called him that since… her.

Casually leaning on the wall next to his dressing room was the mysterious Ms. Harshwhinny that had entered and left his life all those months ago and taken something important with her.

“Ms. Harshwhinny? Is that really you?”

The mare smiled and pushed off the wall, grunting as her full weight settled on her hooves. “In the flesh. Sorry about not getting back to you again, work got busy and, well, one thing led to another..” The mare looked off into the distance and winced, hoping her excuse sounded slightly less shitty to him than it did to her.

Trouble Shoes took a step back, one eyebrow rising as he appraised the slightly larger mare. “Have you put on weight or…”

“That's what I thought at first as well, but judging from the look on your face, I think you already know what happened.”

The stallion stumbled forward, eying the huge bulge in the mare’s stomach with amazement. She looked ready to pop already, but it hadnt been long enough for that unless there was somepony else. But she said he was the only one she had for awhile, which would mean...

“Is it twins?”

“The doctor said no, but I'm not so sure I believe him. I got a little bit more time to go before I pop and I'm already huge.” The mare said with a giggle, swishing her tail back and forth, allowing the stallion to get a real good look.

Trouble Shoes gulped, her stomach had not been the only thing to grow, which would explain why her gait had become a little less coordinated than it was before. Between her legs, nearly squished between her stomach and her legs were the biggest pair of tits Trouble Shoes had ever seen. They hung low, but due to their sheer size it didn't look off, and though Trouble thought it might have been his mind playing tricks on him he was pretty sure he saw a little dribble of milk falling from one of her nipples.

With great reluctance, the stallion tore his eyes away and walked back around in order to look her in the eye. “But I thought you said you were barren. How did this happen?”

The mare merely shrugged, an act that was slightly more difficult than one might think. “I don't have the foggiest. Who would have thought that a virile stallion such as yourself could knock up even an infertile old mare such as myself? But with the amount you stuffed inside me I'm not surprised.”

The mare grinned mischievously at the stallion’s blushing and edged closer to the door. “So, stud, up for round two?”

“I just had a question if you don't mind.” The mare’s smirk fled her face and she looked down, afraid of where this conversation was going to go.

“I guess I owe you that, fire away.”

“What made up your mind to come back?” Trouble gently picked up the mare’s chin and forced their eyes to meet. The pain and guilt found within those violet orbs nearly made him melt, but needed to know.

“I didn't think I could settle down, but after all my flings, I never felt that connection I had with you and despite what I tried to convince myself you were the best lay of my whole life. After I stopped making excuses and really thought about it, I couldn't deny you were the one for me. Knocking up an old barren mare seemed like the perfect sign.” The mare smiled weakly. “Can you ever forgive a foolish mare?”

Trouble Shoes had never been good with words, he got tongue tied too easily and rarely knew what to say. So when the time came to assuage the worries of his love he found no words that would convey his feelings. Instead he did what he had wanted to do from the very moment he first saw her. He leaned in and, with a smile on his face, kissed her gently.

He leaned forward deepening the kiss only to trip and and suddenly end up on his back. “Just my- oof!”

The mare wasted no time and leaped onto the stallion. “Just your luck.” She whispered black, leaning in close, going in for another kiss only to stop when her belly bumped into his stomach.

The pair stopped and looked down at the enormous belly getting in the way of another steamy make out session. “Maybe we should get back to wagon if you were still up for another round?”

The mare pulled herself off the stallion and helped him up. “Of course. If you’re worried about the baby, don't be.” She took a step closer and planted a light kiss on his lips. “And if you’re worried about me still wanting you then I'll have you know I would have taken you right here on the ground if the little ones hadn't gotten in the way.”

The stallion gulped. “My wagon is this way, unless you got another hotel room we can wreck?” He smirked, drawing a chuckle from the mare.

“Not this time, I thought I would see your place and see how much room it has.”

Trouble shoes smiled, leading them towards his wagon. “It doesn't have much, maybe enough for just me and you.”

Harshwhinny smiled back and walked alongside the large stallion. “It sounds perfect.”

Author's Note

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This update is supported by.

DIOKYO

(Huge thank you!)

Tanis

Makani